Homesinorlando.forsale Search Results

$290,000

Under contract-accepting backup offers. Welcome to this charming ground-floor condo, nestled in the highly sought-after 55+ community of Winter Park Gardens. This TWO-bedroom, TWO-bathroom condo offers a perfect blend of comfort, and stunning picturesque views. The open layout seamlessly connects the kitchen to the living area, and into to the sunroom/Florida room. This space is perfect for enjoying the tranquil views, offering a peaceful ambiance year-round. The spacious bedroom is filled with natural light, creating a bright and inviting atmosphere. This condo is located in a vibrant 55+ community that offers beautifully landscaped grounds with lush landscaping, lighted paths, and scenic pond, a sparkling community pool, and a clubhouse where residents can gather and enjoy social activities. The prime location provides easy access to a variety of amenities and attractions. Just minutes away, you'll find the historic Winter Park district, home to the renowned Park Avenue with its boutique shops, restaurants, and cultural events. The nearby Azalea Tennis Center, Mead Botanical Gardens, and Rollins College offer further enriching experiences. Embrace the serene and active lifestyle this community provides, with the added convenience of being close to Downtown Orlando, Baldwin Park, major highways like 408 and I-4, and the MCO Airport. The assigned parking space is just steps away from your front door with plenty of additional parking for guests. Don't miss the chance to make this delightful condo your own.

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Welcome to this charming ground-floor condo, nestled in the highly sought-after 55+ community of Winter Park Gardens. This TWO-bedroom, TWO-bathroom condo offers a perfect blend of comfort, and stunning picturesque views. The open layout seamlessly connects the kitchen to the living area, and into to the sunroom/Florida room. This space is perfect for enjoying the tranquil views, offering a peaceful ambiance year-round. The spacious bedroom is filled with natural light, creating a bright and inviting atmosphere. This condo is located in a vibrant 55+ community that offers beautifully landscaped grounds with lush landscaping, lighted paths, and scenic pond, a sparkling community pool, and a clubhouse where residents can gather and enjoy social activities. The prime location provides easy access to a variety of amenities and attractions. Just minutes away, you'll find the historic Winter Park district, home to the renowned Park Avenue with its boutique shops, restaurants, and cultural events. The nearby Azalea Tennis Center, Mead Botanical Gardens, and Rollins College offer further enriching experiences. Embrace the serene and active lifestyle this community provides, with the added convenience of being close to Downtown Orlando, Baldwin Park, major highways like 408 and I-4, and the MCO Airport. The assigned parking space is just steps away from your front door with plenty of additional parking for guests. Don't miss the chance to make this delightful condo your own.

700 Melrose Avenue Unit H4, Winter Park

$353,000

Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!

3 Beds ⋅ 2 Baths ⋅ Howell Heights SubDv. ⋅ 32789 Zip Code

Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!

2973 Sanbina Street, Winter Park

$615,000

Virtually Staged. Move-in ready Sylvan Heights Mid-Century Bungalow, with no renovations needed. As you approach, you will notice the wonderfully cared for home with mature landscaping and a unique style. A charming, three-bedroom two-bath home has updated Kitchen and Bathrooms, there is even a large formal dining space with a built-in serving bar and wine fridge. The floors were upgraded with engineered hardwood throughout with tile in both bathrooms. Situated on a larger lot with a fully fenced in backyard that also has a 12x15 brick patio and room to add a swimming pool if desired. Sylvan Heights is one of Winter Park's Primer residential communities, that is close to Advent Health's Winter Park Hospital and top-Rated Rollins College. Just a short bike ride to Park Avenue in Downtown Winter Park with tons of shops and restaurants so you won’t have to go far for fun. Also, just minutes to downtown Orlando, and all of the Central Florida attractions so get the guest room ready for visitors... Sound like a home you would like to see. Schedule a private showing today.

3 Beds ⋅ 2 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

Virtually Staged. Move-in ready Sylvan Heights Mid-Century Bungalow, with no renovations needed. As you approach, you will notice the wonderfully cared for home with mature landscaping and a unique style. A charming, three-bedroom two-bath home has updated Kitchen and Bathrooms, there is even a large formal dining space with a built-in serving bar and wine fridge. The floors were upgraded with engineered hardwood throughout with tile in both bathrooms. Situated on a larger lot with a fully fenced in backyard that also has a 12x15 brick patio and room to add a swimming pool if desired. Sylvan Heights is one of Winter Park's Primer residential communities, that is close to Advent Health's Winter Park Hospital and top-Rated Rollins College. Just a short bike ride to Park Avenue in Downtown Winter Park with tons of shops and restaurants so you won’t have to go far for fun. Also, just minutes to downtown Orlando, and all of the Central Florida attractions so get the guest room ready for visitors... Sound like a home you would like to see. Schedule a private showing today.

1780 Goodrich Avenue, Winter Park

$2,500,000

Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

5 Beds ⋅ 6 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

450 Lakewood Drive, Winter Park

$7,164,000

Set on over half an acre along the shores of Lake Maitland in the heart of the coveted Vias, this exceptional residence by Modish Homes is both a former 2018 Parade of Homes winner and a standout example of Winter Park luxury living. From the moment you enter, a dramatic two-story foyer sets the tone, drawing your eye through to the main living space where a statement wood-burning fireplace anchors the room and expansive glass frames breathtaking views of the water beyond. Every space has been thoughtfully designed to maximize both scale and sightlines, creating an effortless connection between indoors and the natural beauty outside. The home features touches of Walnut floors, detailing and doors, bringing warmth throughout. At the center of the home, the chef’s kitchen is both refined and functional, featuring custom cabinetry, a full suite of Dacor appliances, and an oversized walk-in pantry. A striking wet bar with a glass wine wall adds a layer of sophistication, ideal for entertaining. The dining room is equally impressive, offering panoramic lake views and seamless access to the outdoor living areas. The main-level primary suite is a true private retreat, highlighted by chevron-pattern tile flooring and a spa-inspired bath complete with dual vanities, designer lighting, a freestanding soaking tub, and an expansive walk-in shower. The main level also includes two additional guest suites and a glass-enclosed office, offering both comfort and flexibility. Upstairs, two more bedrooms are complemented by a spacious loft and a large balcony that captures sweeping views of the lake. Designed to rival a private resort, the outdoor living experience is nothing short of exceptional. A fully equipped summer kitchen, resort-style pool and spa, two outdoor showers, and expansive green space create a setting that is both functional and visually stunning. A private viewing dock overlooks the water or reconfigure it to a boat dock, allowing you to fully embrace life on the lake while enjoying views of the iconic Isle of Sicily. Beyond the property, the lifestyle is equally compelling. Additional features include a full Control4 home automation system, sauna, and an expansive double-entry driveway providing ample parking. Located just minutes from the boutiques, dining, and cafés of Park Avenue, and within close proximity to Kraft Azalea Garden and the Winter Park Racquet Ball Club, this home offers the perfect balance of privacy and convenience. This is truly a one-of-a-kind opportunity to own a true showpiece on the Winter Park Chain of Lakes.

5 Beds ⋅ 7 Baths ⋅ Sicilian Shores SubDv. ⋅ 32789 Zip Code

Set on over half an acre along the shores of Lake Maitland in the heart of the coveted Vias, this exceptional residence by Modish Homes is both a former 2018 Parade of Homes winner and a standout example of Winter Park luxury living. From the moment you enter, a dramatic two-story foyer sets the tone, drawing your eye through to the main living space where a statement wood-burning fireplace anchors the room and expansive glass frames breathtaking views of the water beyond. Every space has been thoughtfully designed to maximize both scale and sightlines, creating an effortless connection between indoors and the natural beauty outside. The home features touches of Walnut floors, detailing and doors, bringing warmth throughout. At the center of the home, the chef’s kitchen is both refined and functional, featuring custom cabinetry, a full suite of Dacor appliances, and an oversized walk-in pantry. A striking wet bar with a glass wine wall adds a layer of sophistication, ideal for entertaining. The dining room is equally impressive, offering panoramic lake views and seamless access to the outdoor living areas. The main-level primary suite is a true private retreat, highlighted by chevron-pattern tile flooring and a spa-inspired bath complete with dual vanities, designer lighting, a freestanding soaking tub, and an expansive walk-in shower. The main level also includes two additional guest suites and a glass-enclosed office, offering both comfort and flexibility. Upstairs, two more bedrooms are complemented by a spacious loft and a large balcony that captures sweeping views of the lake. Designed to rival a private resort, the outdoor living experience is nothing short of exceptional. A fully equipped summer kitchen, resort-style pool and spa, two outdoor showers, and expansive green space create a setting that is both functional and visually stunning. A private viewing dock overlooks the water or reconfigure it to a boat dock, allowing you to fully embrace life on the lake while enjoying views of the iconic Isle of Sicily. Beyond the property, the lifestyle is equally compelling. Additional features include a full Control4 home automation system, sauna, and an expansive double-entry driveway providing ample parking. Located just minutes from the boutiques, dining, and cafés of Park Avenue, and within close proximity to Kraft Azalea Garden and the Winter Park Racquet Ball Club, this home offers the perfect balance of privacy and convenience. This is truly a one-of-a-kind opportunity to own a true showpiece on the Winter Park Chain of Lakes.

1821 Pinetree Road, Winter Park

$1,625,000

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

4 Beds ⋅ 2 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

446 Melrose Avenue, Winter Park

$345,000

Welcome to 2889 Rouen Avenue, Fresh exterior paint and move-in-ready 3-bedroom, 2-bath residence offering approximately 1,140 square feet of comfortable living space. This home features a bright and functional layout, well-sized bedrooms, and a large fenced yard with plenty of room to enjoy the outdoors. Brand New water heater. Brand new Roof is underway. Conveniently located near Rollins College, Park Avenue, Full Sail University, shopping, dining, and I-4, and zoned for Dommerich, this property offers an outstanding opportunity in a sought-after location. see private remarks and showing time for direct seller’s contact.

3 Beds ⋅ 2 Baths ⋅ Winter Park Manor SubDv. ⋅ 32789 Zip Code

Welcome to 2889 Rouen Avenue, Fresh exterior paint and move-in-ready 3-bedroom, 2-bath residence offering approximately 1,140 square feet of comfortable living space. This home features a bright and functional layout, well-sized bedrooms, and a large fenced yard with plenty of room to enjoy the outdoors. Brand New water heater. Brand new Roof is underway. Conveniently located near Rollins College, Park Avenue, Full Sail University, shopping, dining, and I-4, and zoned for Dommerich, this property offers an outstanding opportunity in a sought-after location. see private remarks and showing time for direct seller’s contact.

2889 Rouen Avenue, Winter Park

$3,978,550

PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5 luxurious baths, and a dedicated executive office. At the heart of the home, a gourmet chef's kitchen flows seamlessly into a light-filled great room, perfect for grand-scale entertaining. Step outside to your private sanctuary: a brand-new custom pool and a sprawling covered lanai featuring a cozy outdoor fireplace. Situated on a premier corner lot with a brick-lined street, you are just steps away from the Winter Park Racquet Club and minutes from the world-class dining and shopping of Park Avenue. Experience the pinnacle of Winter Park living in a home designed for the most discerning buyer.

4 Beds ⋅ 5 Baths ⋅ Tuscania SubDv. ⋅ 32789 Zip Code

PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5 luxurious baths, and a dedicated executive office. At the heart of the home, a gourmet chef's kitchen flows seamlessly into a light-filled great room, perfect for grand-scale entertaining. Step outside to your private sanctuary: a brand-new custom pool and a sprawling covered lanai featuring a cozy outdoor fireplace. Situated on a premier corner lot with a brick-lined street, you are just steps away from the Winter Park Racquet Club and minutes from the world-class dining and shopping of Park Avenue. Experience the pinnacle of Winter Park living in a home designed for the most discerning buyer.

2020 Via Tuscany, Winter Park

$1,995,000

Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

1398 Grove Terrace, Winter Park

$4,285,000

Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious gourmet kitchen overlooks the main living areas and pool, and is equipped with premium Wolf appliances and a separate chef’s kitchen for added convenience. Enjoy seamless indoor-outdoor living with a covered lanai featuring motorized screens, heaters, and a mosquito misting system. The outdoor space also includes a summer kitchen, gas fire pit, and a pool equipped with a swim jet system that creates a continuous current, effectively transforming it into an endless lap pool. A detached fitness studio with a steam shower provides a private wellness retreat. Additional highlights include custom built-ins, engineered hardwood floors and surround sound throughout. The oversized two-car garage offers epoxy flooring, custom storage, and a dog wash station. Irrigation is supplied by a private well, and the home also features underground utilities and a full security system. The exterior is designed for both beauty and low maintenance, with manicured landscaping and artificial turf that stays lush year-round. With no HOA, added privacy, and exceptional attention to detail throughout, this home offers a rare opportunity to experience luxury living at its finest. This home is conveniently located near the Enzian Theater and less than a mile from Winter Park Village, with top-rated schools nearby, this home combines comfort, style and an unbeatable location. Schedule your private showing today.

4 Beds ⋅ 6 Baths ⋅ Winflor Court Pt Rep SubDv. ⋅ 32789 Zip Code

Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious gourmet kitchen overlooks the main living areas and pool, and is equipped with premium Wolf appliances and a separate chef’s kitchen for added convenience. Enjoy seamless indoor-outdoor living with a covered lanai featuring motorized screens, heaters, and a mosquito misting system. The outdoor space also includes a summer kitchen, gas fire pit, and a pool equipped with a swim jet system that creates a continuous current, effectively transforming it into an endless lap pool. A detached fitness studio with a steam shower provides a private wellness retreat. Additional highlights include custom built-ins, engineered hardwood floors and surround sound throughout. The oversized two-car garage offers epoxy flooring, custom storage, and a dog wash station. Irrigation is supplied by a private well, and the home also features underground utilities and a full security system. The exterior is designed for both beauty and low maintenance, with manicured landscaping and artificial turf that stays lush year-round. With no HOA, added privacy, and exceptional attention to detail throughout, this home offers a rare opportunity to experience luxury living at its finest. This home is conveniently located near the Enzian Theater and less than a mile from Winter Park Village, with top-rated schools nearby, this home combines comfort, style and an unbeatable location. Schedule your private showing today.

1441 Cardinal Court, Winter Park

$920,000

Virtually Staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy that carries throughout the property. An oversized two-car garage and thoughtfully designed exterior set the tone for what awaits inside. Step through the entry and into a light-filled interior where volume ceilings and an open-concept layout create an immediate sense of space and flow. The home is designed to draw your eye outward — through expansive living areas, beyond the enclosed lanai, and into the serene pool and spa, creating a seamless connection between indoor and outdoor living. Every detail has been carefully curated to balance warmth and modern refinement. Rich Brazilian rosewood flooring anchors the main living spaces, while durable quarry tile provides both style and functionality in the kitchen and transitional areas. The kitchen itself has been reimagined with updated cabinetry and modern appliances, offering a clean, sophisticated space that remains highly functional for everyday living and entertaining. The split floor plan provides both comfort and privacy, with a spacious primary suite and well-appointed secondary bedrooms. Both bathrooms have been tastefully updated with contemporary finishes, while additional enhancements throughout the home — including updated lighting, hardware, flooring, and fresh interior touches — contribute to its move-in-ready appeal. Designed for the Florida lifestyle, the home truly comes to life when the expansive sliding glass doors are opened, blending the interior with the screened outdoor living space. The pool and spa become a natural extension of the home — perfect for quiet mornings, entertaining guests, or simply enjoying the year-round sunshine in complete privacy. Located just moments from Lake Mizell, part of the highly sought-after Winter Park Chain of Lakes, the property offers not only a beautiful home, but a lifestyle defined by scenic surroundings, walkability, and timeless charm. 250 Cortland Ave is more than a home — it is a rare opportunity to own a thoughtfully designed residence in one of Winter Park’s most desirable and established neighborhoods.

3 Beds ⋅ 2 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code

Virtually Staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy that carries throughout the property. An oversized two-car garage and thoughtfully designed exterior set the tone for what awaits inside. Step through the entry and into a light-filled interior where volume ceilings and an open-concept layout create an immediate sense of space and flow. The home is designed to draw your eye outward — through expansive living areas, beyond the enclosed lanai, and into the serene pool and spa, creating a seamless connection between indoor and outdoor living. Every detail has been carefully curated to balance warmth and modern refinement. Rich Brazilian rosewood flooring anchors the main living spaces, while durable quarry tile provides both style and functionality in the kitchen and transitional areas. The kitchen itself has been reimagined with updated cabinetry and modern appliances, offering a clean, sophisticated space that remains highly functional for everyday living and entertaining. The split floor plan provides both comfort and privacy, with a spacious primary suite and well-appointed secondary bedrooms. Both bathrooms have been tastefully updated with contemporary finishes, while additional enhancements throughout the home — including updated lighting, hardware, flooring, and fresh interior touches — contribute to its move-in-ready appeal. Designed for the Florida lifestyle, the home truly comes to life when the expansive sliding glass doors are opened, blending the interior with the screened outdoor living space. The pool and spa become a natural extension of the home — perfect for quiet mornings, entertaining guests, or simply enjoying the year-round sunshine in complete privacy. Located just moments from Lake Mizell, part of the highly sought-after Winter Park Chain of Lakes, the property offers not only a beautiful home, but a lifestyle defined by scenic surroundings, walkability, and timeless charm. 250 Cortland Ave is more than a home — it is a rare opportunity to own a thoughtfully designed residence in one of Winter Park’s most desirable and established neighborhoods.

250 Cortland Avenue, Winter Park

$776,533

Amazing location near Park Ave! Completely reimagined and rebuilt from the studs, this exceptional one-story 3-bedroom, 2-bath residence offers the perfect blend of modern luxury and timeless charm in one of Winter Park’s most coveted locations—just a short stroll to the boutiques, dining, and cultural attractions of Park Avenue. Every inch of this home has been thoughtfully renovated in 2026 with no detail overlooked. Enjoy peace of mind with all-new electrical, plumbing, HVAC, windows, and garage door, ensuring efficiency and reliability for years to come. Roof 2021. A beautifully designed paver driveway enhances the home's curb appeal, creating a warm and welcoming first impression. Inside, the open and inviting floor plan is enhanced by premium tile flooring, designer finishes, and an abundance of natural light. The stunning, fully updated kitchen serves as the heart of the home, featuring sleek cabinetry, quartz counters, high-end finishes, and center island with bar seating. The kitchen flows seamlessly into the living and dining spaces—perfect for both everyday living and entertaining. Both bathrooms have been beautifully redesigned with modern fixtures and elegant touches. The spacious first floor primary suite offers a serene retreat with en-suite bath featuring a stunning walk in shower. Enjoy the convenience of the indoor laundry room with extra storage space. Step outside to the screened in back porch to enjoy the Florida lifestyle. Situated in a highly desirable Winter Park neighborhood, this turnkey home combines walkability, luxury upgrades, and an unbeatable location. A rare opportunity to own a like-new home just moments from the very best of Park Avenue living.

3 Beds ⋅ 2 Baths ⋅ Winter Park Oasis SubDv. ⋅ 32789 Zip Code

Amazing location near Park Ave! Completely reimagined and rebuilt from the studs, this exceptional one-story 3-bedroom, 2-bath residence offers the perfect blend of modern luxury and timeless charm in one of Winter Park’s most coveted locations—just a short stroll to the boutiques, dining, and cultural attractions of Park Avenue. Every inch of this home has been thoughtfully renovated in 2026 with no detail overlooked. Enjoy peace of mind with all-new electrical, plumbing, HVAC, windows, and garage door, ensuring efficiency and reliability for years to come. Roof 2021. A beautifully designed paver driveway enhances the home's curb appeal, creating a warm and welcoming first impression. Inside, the open and inviting floor plan is enhanced by premium tile flooring, designer finishes, and an abundance of natural light. The stunning, fully updated kitchen serves as the heart of the home, featuring sleek cabinetry, quartz counters, high-end finishes, and center island with bar seating. The kitchen flows seamlessly into the living and dining spaces—perfect for both everyday living and entertaining. Both bathrooms have been beautifully redesigned with modern fixtures and elegant touches. The spacious first floor primary suite offers a serene retreat with en-suite bath featuring a stunning walk in shower. Enjoy the convenience of the indoor laundry room with extra storage space. Step outside to the screened in back porch to enjoy the Florida lifestyle. Situated in a highly desirable Winter Park neighborhood, this turnkey home combines walkability, luxury upgrades, and an unbeatable location. A rare opportunity to own a like-new home just moments from the very best of Park Avenue living.

781 Northwood Circle, Winter Park

$2,699,000

Under contract-accepting backup offers. Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.

4 Beds ⋅ 6 Baths ⋅ Windsong Lakeside Sec 02 43/71 SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.

1529 Holts Grove Circle, Winter Park

$3,100,000

Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

5 Beds ⋅ 5 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

141 Glenridge Way, Winter Park

$2,490,000

Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot, providing modern functionality, Old World charm, and an unmatched lifestyle. The main residence spans over 3,600+ SF with 4 bedrooms, 4 bathrooms, and an attached 2-car garage. Across the brick driveway is a detached, fully-equipped 700+ SF studio apartment (5th bedroom suite) located above an additional 2-car garage, and an air-conditioned outdoor bar. With two dwellings, a 4-car garage, and an expansive outdoor entertaining space on a ½ acre lot, this home is a true private compound. Notable updates include newer HVAC systems (2020 & 2025), a new tankless gas water heater (2024), a fully renovated laundry room with new LG stackable washer/dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more... Ask for the $400K list of improvements! Enter the main residence to a family room that stretches 30 feet wide, with 12-foot ceilings, a gas fireplace, and multiple French doors lining the rear wall to showcase the brick-paver pool deck and lush, fenced-in backyard oasis, and southern exposure that invites natural light all morning and afternoon. The expansive family room is open to the kitchen, making this home ideal for entertaining. The kitchen perfectly balances charm and function, with a NEW Sub-Zero refrigerator, natural gas Wolf range, 2 Miele dishwashers, a copper-topped island that offers room for prep, serving, or seating, and a spacious dinette area with pool views. Behind the kitchen sits a dining room and adjacent den (currently used as a library/office) for more living/dining flexibility. A side entrance opens to a covered side porch overlooking a generous side yard framed by tall Podocarpus hedges... ideal for pets, a fabulous garden, or future expanded parking. A 1st floor rear bedroom wing presents 3 bedrooms & 3 full baths. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent luxury bathroom renovation with elegant custom finishes including a large glass shower with 3 showerheads, 2 separate vanities, a Toto washlet, and tons of cabinetry for linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while 3 custom walk-in closets create a true dressing room experience, or the perfect opportunity to turn excess space into an office or special hobby room. Designed for entertaining, the outdoor living is equally impressive, with a sprawling lawn surrounding the large saltwater pool and an expansive paver patio for lounging and dining. A covered, air-conditioned bar is designed with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge...all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a natural gas grill, pool bath, and outdoor shower. Above the detached 2-car garage is the studio apartment with a private entry, along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from the vibrant Park Avenue, this distinctive Winter Park compound is a one-of-a-kind property!

5 Beds ⋅ 6 Baths ⋅ Temple Heights SubDv. ⋅ 32789 Zip Code

Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot, providing modern functionality, Old World charm, and an unmatched lifestyle. The main residence spans over 3,600+ SF with 4 bedrooms, 4 bathrooms, and an attached 2-car garage. Across the brick driveway is a detached, fully-equipped 700+ SF studio apartment (5th bedroom suite) located above an additional 2-car garage, and an air-conditioned outdoor bar. With two dwellings, a 4-car garage, and an expansive outdoor entertaining space on a ½ acre lot, this home is a true private compound. Notable updates include newer HVAC systems (2020 & 2025), a new tankless gas water heater (2024), a fully renovated laundry room with new LG stackable washer/dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more... Ask for the $400K list of improvements! Enter the main residence to a family room that stretches 30 feet wide, with 12-foot ceilings, a gas fireplace, and multiple French doors lining the rear wall to showcase the brick-paver pool deck and lush, fenced-in backyard oasis, and southern exposure that invites natural light all morning and afternoon. The expansive family room is open to the kitchen, making this home ideal for entertaining. The kitchen perfectly balances charm and function, with a NEW Sub-Zero refrigerator, natural gas Wolf range, 2 Miele dishwashers, a copper-topped island that offers room for prep, serving, or seating, and a spacious dinette area with pool views. Behind the kitchen sits a dining room and adjacent den (currently used as a library/office) for more living/dining flexibility. A side entrance opens to a covered side porch overlooking a generous side yard framed by tall Podocarpus hedges... ideal for pets, a fabulous garden, or future expanded parking. A 1st floor rear bedroom wing presents 3 bedrooms & 3 full baths. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent luxury bathroom renovation with elegant custom finishes including a large glass shower with 3 showerheads, 2 separate vanities, a Toto washlet, and tons of cabinetry for linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while 3 custom walk-in closets create a true dressing room experience, or the perfect opportunity to turn excess space into an office or special hobby room. Designed for entertaining, the outdoor living is equally impressive, with a sprawling lawn surrounding the large saltwater pool and an expansive paver patio for lounging and dining. A covered, air-conditioned bar is designed with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge...all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a natural gas grill, pool bath, and outdoor shower. Above the detached 2-car garage is the studio apartment with a private entry, along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from the vibrant Park Avenue, this distinctive Winter Park compound is a one-of-a-kind property!

1300 Mayfield Avenue, Winter Park

$3,675,000

JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

5 Beds ⋅ 5 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

150 Dana Way, Winter Park

$3,755,000

Experience the art of luxury living just steps from the boutiques, cafés & celebrated dining of Park Avenue, Winter Park Village, Rollins College & the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle. THIS HOME RECEIVED THE 2025 ARDA GRAND AWARD FOR CUSTOM HOME (built). A thoughtful quad split bedroom layout offers 4 bedrooms & 4.5 baths, including a serene primary suite with Hunter Douglas automated light filtering/light blocking shades. The primary suite includes a spectacular custom walk-in closet featuring an island, 36 drawers, built-in benches, dual hampers, a safe, locking jewelry drawers & display shelving. The ensuite bath provides a spa-like retreat. Additionally, two guest suites also enjoy private ensuite baths & large walk-in closets. The showpiece chef’s kitchen is designed for both culinary mastery & entertaining, featuring Dura Supreme cabinetry, a 60" Wolf dual fuel range with griddle, pot filler, 36" Sub Zero Designer Column refrigerator, Sub Zero freezer drawers, two Bosch dishwashers, Wolf microwave drawer, Revati dual tier 57" sink with custom inserts for colander, cutting board & strainer & dual automatic faucets. Dramatic 15-foot waterfall island with Dekton countertops & matching backsplash. A hidden scullery adds even more function with a French door refrigerator, sink, pantry shelving, Dekton counters & floating LED-lit shelves. The stylish wet bar includes white oak floating shelves with LED lighting, Dekton countertops & backsplash, a glass rinser, Scotsman gourmet ice machine & Thermador refrigerator drawers. Dining room has a climate-controlled wine cellar that holds up to 240 bottles. Enjoy picking lemons, limes & oranges from your own mature trees for juicing or garnishes. The expansive family room impresses with six LED-lit floating shelves, a 60" linear gas fireplace & an extraordinary 52 feet of 10-foot-tall sliding stacking patio doors that create seamless indoor-outdoor flow. Step outside to a resort-style outdoor kitchen & living area, complete with a Dekton waterfall countertop, Perlick refrigerator drawers & kegerator, 48" DCS grill with rotisserie & 2 side burners, pizza oven, Ruvati sink with ice chest, bar-height island seating, three 60" Minka Aire remote control fans, outdoor electric fireplace & retractable screens. The app-controlled pool features water elements, bubblers, two ledge loungers with umbrella holder/end table/ice chest & a 9-seat hot tub. Custom closets are found throughout the home, including the media room with built-in Queen Murphy bed & closet & a dedicated exercise room with closet or potential fifth bedroom. Large office filled with natural sunlight. The laundry room includes custom cabinetry with built-ins for pet bowls & bed & a fold-out ironing board. Additional features include Visual Comfort lighting, Guardian security system, Trane home automation, Quantum Fiber, built-in speakers throughout the main living areas & outdoor kitchen, living room & pool, Emtek hardware, PGT casement windows & 8" white oak hardwood floors. The sellers will also provide a one-year home warranty for added benefit. This home delivers a refined, fun & effortless luxury lifestyle in one of Winter Park’s most coveted locations—where every detail is designed to impress. Finding a one-story, almost-new home on a large lot in Winter Park is like finding a rare gem!

4 Beds ⋅ 5 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Experience the art of luxury living just steps from the boutiques, cafés & celebrated dining of Park Avenue, Winter Park Village, Rollins College & the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle. THIS HOME RECEIVED THE 2025 ARDA GRAND AWARD FOR CUSTOM HOME (built). A thoughtful quad split bedroom layout offers 4 bedrooms & 4.5 baths, including a serene primary suite with Hunter Douglas automated light filtering/light blocking shades. The primary suite includes a spectacular custom walk-in closet featuring an island, 36 drawers, built-in benches, dual hampers, a safe, locking jewelry drawers & display shelving. The ensuite bath provides a spa-like retreat. Additionally, two guest suites also enjoy private ensuite baths & large walk-in closets. The showpiece chef’s kitchen is designed for both culinary mastery & entertaining, featuring Dura Supreme cabinetry, a 60" Wolf dual fuel range with griddle, pot filler, 36" Sub Zero Designer Column refrigerator, Sub Zero freezer drawers, two Bosch dishwashers, Wolf microwave drawer, Revati dual tier 57" sink with custom inserts for colander, cutting board & strainer & dual automatic faucets. Dramatic 15-foot waterfall island with Dekton countertops & matching backsplash. A hidden scullery adds even more function with a French door refrigerator, sink, pantry shelving, Dekton counters & floating LED-lit shelves. The stylish wet bar includes white oak floating shelves with LED lighting, Dekton countertops & backsplash, a glass rinser, Scotsman gourmet ice machine & Thermador refrigerator drawers. Dining room has a climate-controlled wine cellar that holds up to 240 bottles. Enjoy picking lemons, limes & oranges from your own mature trees for juicing or garnishes. The expansive family room impresses with six LED-lit floating shelves, a 60" linear gas fireplace & an extraordinary 52 feet of 10-foot-tall sliding stacking patio doors that create seamless indoor-outdoor flow. Step outside to a resort-style outdoor kitchen & living area, complete with a Dekton waterfall countertop, Perlick refrigerator drawers & kegerator, 48" DCS grill with rotisserie & 2 side burners, pizza oven, Ruvati sink with ice chest, bar-height island seating, three 60" Minka Aire remote control fans, outdoor electric fireplace & retractable screens. The app-controlled pool features water elements, bubblers, two ledge loungers with umbrella holder/end table/ice chest & a 9-seat hot tub. Custom closets are found throughout the home, including the media room with built-in Queen Murphy bed & closet & a dedicated exercise room with closet or potential fifth bedroom. Large office filled with natural sunlight. The laundry room includes custom cabinetry with built-ins for pet bowls & bed & a fold-out ironing board. Additional features include Visual Comfort lighting, Guardian security system, Trane home automation, Quantum Fiber, built-in speakers throughout the main living areas & outdoor kitchen, living room & pool, Emtek hardware, PGT casement windows & 8" white oak hardwood floors. The sellers will also provide a one-year home warranty for added benefit. This home delivers a refined, fun & effortless luxury lifestyle in one of Winter Park’s most coveted locations—where every detail is designed to impress. Finding a one-story, almost-new home on a large lot in Winter Park is like finding a rare gem!

1117 Kenwood Avenue, Winter Park

$1,650,000

Canal Front Oasis on the Winter Park Chain of Lakes! (Seller Financing Available for Qualified Buyers) Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. *The canal allows for full Lake Maitland and Winter Park Chain of Lakes access by powerboat. (Current owners have a 19' outboard they use to pull tubes, ski, wakeboard, quick trips to dog island and entertaining via scenic tours through the Winter Park Chain of Lakes.) Originally built in 1959 and completely renovated in 2022, this two-story retreat combines rustic charm with modern luxury. Step inside to discover an open floor plan anchored by a gas fireplace, open kitchen and dining room, warm custom woodwork, and thoughtful built-ins throughout. The renovation includes new electrical, plumbing, new kitchen and baths, engineered hardwood flooring throughout, amongst many more upgrades. The redesigned layout adds over 1,000 square feet, featuring a spacious first-floor laundry room and an all-new second story with a luxurious primary suite, a guest bedroom (currently used as an office), and a full bathroom. Outdoors, enjoy a new boathouse on a canal and an inviting outdoor living area — perfect for entertaining or unwinding along the peaceful canal that connects directly to Lake Maitland and the renowned Winter Park Chain of Lakes. The rear of the property backs up to a wooded conservation area that provides privacy and tranquility. The current owner received a variance for a future pool, and Orange County previously had no objections to pool installation (new owner would need to reapply). The property sits in one of Central Florida’s most sought-after school zones: Dommerich Elementary, Maitland Middle, and Winter Park High. Families here often bike or walk to school. Enjoy regular walks through scenic streets lined with mature cypress trees, palms, vibrant native vegetation and beautiful homes that line Lake Maitland. With no HOA, residents may optionally join the neighborhood association (approx. $120/year) for access to two lakefront parks and a private boat ramp. From the modern amenities and artful landscaping to the serene waterfront setting, this is truly a one-of-a-kind property that blends nature, comfort, and sophistication in the heart of Winter Park. *Canal boat tour video that showcases the trip from the canal to Lake Maitland is available via the virtual tour link in the listing.

4 Beds ⋅ 3 Baths ⋅ Maitland Shores SubDv. ⋅ 32789 Zip Code

Canal Front Oasis on the Winter Park Chain of Lakes! (Seller Financing Available for Qualified Buyers) Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. *The canal allows for full Lake Maitland and Winter Park Chain of Lakes access by powerboat. (Current owners have a 19' outboard they use to pull tubes, ski, wakeboard, quick trips to dog island and entertaining via scenic tours through the Winter Park Chain of Lakes.) Originally built in 1959 and completely renovated in 2022, this two-story retreat combines rustic charm with modern luxury. Step inside to discover an open floor plan anchored by a gas fireplace, open kitchen and dining room, warm custom woodwork, and thoughtful built-ins throughout. The renovation includes new electrical, plumbing, new kitchen and baths, engineered hardwood flooring throughout, amongst many more upgrades. The redesigned layout adds over 1,000 square feet, featuring a spacious first-floor laundry room and an all-new second story with a luxurious primary suite, a guest bedroom (currently used as an office), and a full bathroom. Outdoors, enjoy a new boathouse on a canal and an inviting outdoor living area — perfect for entertaining or unwinding along the peaceful canal that connects directly to Lake Maitland and the renowned Winter Park Chain of Lakes. The rear of the property backs up to a wooded conservation area that provides privacy and tranquility. The current owner received a variance for a future pool, and Orange County previously had no objections to pool installation (new owner would need to reapply). The property sits in one of Central Florida’s most sought-after school zones: Dommerich Elementary, Maitland Middle, and Winter Park High. Families here often bike or walk to school. Enjoy regular walks through scenic streets lined with mature cypress trees, palms, vibrant native vegetation and beautiful homes that line Lake Maitland. With no HOA, residents may optionally join the neighborhood association (approx. $120/year) for access to two lakefront parks and a private boat ramp. From the modern amenities and artful landscaping to the serene waterfront setting, this is truly a one-of-a-kind property that blends nature, comfort, and sophistication in the heart of Winter Park. *Canal boat tour video that showcases the trip from the canal to Lake Maitland is available via the virtual tour link in the listing.

1016 Howell Branch Road, Winter Park

$595,000

Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an interior laundry room. Zoned for Winter Park schools, minutes from downtown Park Ave., Rollins College and Advent Health Winter Park. Property is a gem perfect for a renovation or an opportunity to build new.

3 Beds ⋅ 2 Baths ⋅ Golfview Heights SubDv. ⋅ 32789 Zip Code

Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an interior laundry room. Zoned for Winter Park schools, minutes from downtown Park Ave., Rollins College and Advent Health Winter Park. Property is a gem perfect for a renovation or an opportunity to build new.

1760 Greenwich Avenue, Winter Park

$994,000

Virtually Staged. NEW CONCRETE CIRCULAR DRIVE AND NEW CONCRETE SIDEWALKS JULY 2026! PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

4 Beds ⋅ 3 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code

Virtually Staged. NEW CONCRETE CIRCULAR DRIVE AND NEW CONCRETE SIDEWALKS JULY 2026! PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

1800 Magnolia Avenue, Winter Park

$865,000

Rare opportunity to own a beautifully upgraded lakefront property on half acre in one of Winter Park's most desirable locations. This homesite offers the perfect setting to enjoy the current residence or build your future dream home! When you step inside you'll find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes. The home boasts new windows that fill the space with natural light and frame serene lake views, as well as a brand new roof and AC offering peace of mind for years to come. Split floor plan with 3 large bedrooms and each has a walk-in closet. Step outside and take in the beautifully landscaped yard, complete with mature trees and plenty of space and privacy. Whether you’re sipping coffee by the water or hosting friends for a sunset BBQ, this home is made for living the good life! Zoned for A rated schools. Situated on a quiet street yet just minutes from Winter Park and Baldwin Park dining, shopping, parks and culture. Call today before it's gone!

3 Beds ⋅ 2 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Rare opportunity to own a beautifully upgraded lakefront property on half acre in one of Winter Park's most desirable locations. This homesite offers the perfect setting to enjoy the current residence or build your future dream home! When you step inside you'll find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes. The home boasts new windows that fill the space with natural light and frame serene lake views, as well as a brand new roof and AC offering peace of mind for years to come. Split floor plan with 3 large bedrooms and each has a walk-in closet. Step outside and take in the beautifully landscaped yard, complete with mature trees and plenty of space and privacy. Whether you’re sipping coffee by the water or hosting friends for a sunset BBQ, this home is made for living the good life! Zoned for A rated schools. Situated on a quiet street yet just minutes from Winter Park and Baldwin Park dining, shopping, parks and culture. Call today before it's gone!

2823 Wright Avenue, Winter Park

$1,500,000

Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park Chain of Lakes. This well-maintained home features a layout with warm and inviting living spaces and abundant natural light. The original front door faces Palmer Avenue, while a later addition created the day-to-day entrance along Old England Avenue. Two separate living areas provide versatility for both relaxing and entertaining, and both the family room and the original living room, currently used as an office, feature wood-burning fireplaces. Just off the family room, a screened porch overlooks the lap pool and backyard, creating an easy connection between indoor and outdoor living. The dining room is lined with built-in bookcases, one of several thoughtful details found throughout the home. The kitchen enjoys views of the backyard and opens to a breakfast area with built-in cabinetry and French doors leading outside. A walk-in pantry adds practical storage. Off the original living room, an enclosed sunroom with original tile and additional built-ins offers a cozy space for reading, working, or unwinding. The primary bedroom opens to the backyard through French doors and includes built-in drawers in addition to closet storage. Its bath features a pedestal sink and clawfoot tub. A second bedroom is located across the home with access to a bathroom off the hallway, providing comfort and privacy for guests or family. Recent updates include a 2014 roof, gas water heater (2022), HVAC systems (2022 and 2023), and updated plumbing and electrical panels. A sprinkler system adds convenience for maintaining the grounds. This is a rare opportunity to build your dream home or enjoy this charming property as-is, ideally located just a couple of blocks from Park Avenue.

2 Beds ⋅ 2 Baths ⋅ Robert Dhu Macdonald Park SubDv. ⋅ 32789 Zip Code

Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park Chain of Lakes. This well-maintained home features a layout with warm and inviting living spaces and abundant natural light. The original front door faces Palmer Avenue, while a later addition created the day-to-day entrance along Old England Avenue. Two separate living areas provide versatility for both relaxing and entertaining, and both the family room and the original living room, currently used as an office, feature wood-burning fireplaces. Just off the family room, a screened porch overlooks the lap pool and backyard, creating an easy connection between indoor and outdoor living. The dining room is lined with built-in bookcases, one of several thoughtful details found throughout the home. The kitchen enjoys views of the backyard and opens to a breakfast area with built-in cabinetry and French doors leading outside. A walk-in pantry adds practical storage. Off the original living room, an enclosed sunroom with original tile and additional built-ins offers a cozy space for reading, working, or unwinding. The primary bedroom opens to the backyard through French doors and includes built-in drawers in addition to closet storage. Its bath features a pedestal sink and clawfoot tub. A second bedroom is located across the home with access to a bathroom off the hallway, providing comfort and privacy for guests or family. Recent updates include a 2014 roof, gas water heater (2022), HVAC systems (2022 and 2023), and updated plumbing and electrical panels. A sprinkler system adds convenience for maintaining the grounds. This is a rare opportunity to build your dream home or enjoy this charming property as-is, ideally located just a couple of blocks from Park Avenue.

246 Palmer Avenue, Winter Park

$3,275,000

This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.

4 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code

This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.

1581 Forest Avenue, Winter Park

$1,688,750

Presenting 1705 Elizabeths Walk for the first time since original construction, an exceptional custom residence located in the highly sought-after Windsong community of Winter Park. Perfectly positioned on a beautifully landscaped .34-acre lot, this elegant 5-bedroom, 5-bathroom estate offers nearly 4,000 square feet of refined living space designed for both comfortable living and sophisticated entertaining. From the moment you enter, you’re greeted by soaring volume ceilings, rich architectural details, and an abundance of natural light that create an inviting and luxurious atmosphere. The thoughtfully designed floor plan features formal living and dining spaces, a spacious family room, upstairs family room and loft, bonus room, and a chef-inspired kitchen with an island, breakfast bar, and large pantry, seamlessly connecting the home’s main gathering areas. The private primary suite on the main level serves as a tranquil retreat, complete with a spa-inspired bathroom featuring dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms provide generous space for family and guests, while flexible living areas allow for a home office, library, or game room. Step outside to enjoy the Florida lifestyle with beautifully landscaped grounds and a huge outdoor living area, complete with an exterior gas fireplace for those chilly winter days, and ideal for relaxing or entertaining. Located within the prestigious Windsong neighborhood, residents enjoy access to community amenities including parks, playgrounds, boat dock and rental, and resort-style pools, all just minutes from Park Avenue’s world-class dining, shopping, and cultural attractions. Zoned for top-rated Winter Park schools, this remarkable home offers the perfect blend of luxury, comfort, and location in one of Central Florida’s most desirable communities.

5 Beds ⋅ 5 Baths ⋅ Windsong Elizabeths Walk SubDv. ⋅ 32789 Zip Code

Presenting 1705 Elizabeths Walk for the first time since original construction, an exceptional custom residence located in the highly sought-after Windsong community of Winter Park. Perfectly positioned on a beautifully landscaped .34-acre lot, this elegant 5-bedroom, 5-bathroom estate offers nearly 4,000 square feet of refined living space designed for both comfortable living and sophisticated entertaining. From the moment you enter, you’re greeted by soaring volume ceilings, rich architectural details, and an abundance of natural light that create an inviting and luxurious atmosphere. The thoughtfully designed floor plan features formal living and dining spaces, a spacious family room, upstairs family room and loft, bonus room, and a chef-inspired kitchen with an island, breakfast bar, and large pantry, seamlessly connecting the home’s main gathering areas. The private primary suite on the main level serves as a tranquil retreat, complete with a spa-inspired bathroom featuring dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms provide generous space for family and guests, while flexible living areas allow for a home office, library, or game room. Step outside to enjoy the Florida lifestyle with beautifully landscaped grounds and a huge outdoor living area, complete with an exterior gas fireplace for those chilly winter days, and ideal for relaxing or entertaining. Located within the prestigious Windsong neighborhood, residents enjoy access to community amenities including parks, playgrounds, boat dock and rental, and resort-style pools, all just minutes from Park Avenue’s world-class dining, shopping, and cultural attractions. Zoned for top-rated Winter Park schools, this remarkable home offers the perfect blend of luxury, comfort, and location in one of Central Florida’s most desirable communities.

1705 Elizabeths Walk, Winter Park

$1,675,000

Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite offers 3,851 square feet of living space, remarkable flexibility, and the kind of charm that simply cannot be replicated. Buyers will also appreciate the peace of mind that comes with major recent updates, including a metal roof installed in 2017, two HVAC units replaced in 2026, a third HVAC unit replaced in 2022, and two water heaters installed in 2025. The pool was resurfaced in 2025, the exterior and interior of the home was painted in 2025, & the house has also been completely re-plumbed! From the moment you arrive, the home makes a lasting impression with its large brick front porch, circular driveway, mature landscaping, detached oversized 2 car garage, and classic architectural presence. Large windows and thoughtfully designed living spaces fill the home with natural light, while hardwood floors, custom built-ins, plantation shutters, fireplaces, and refined traditional details create a warm and inviting feel throughout. This is the perfect blend of classic Winter Park charm and functional modern updates. The floor plan offers both elegance and versatility. In addition to five bedrooms, the home features an office space that can also serve as a formal living room, library, or flex space depending on your needs. The spacious family room is anchored by one of the home’s two wood burning fireplaces and opens beautifully to the outdoor living area, creating an easy flow for both everyday living and entertaining. The kitchen offers granite countertops, custom cabinetry, abundant counter space, a large island, and lots of natural light. It is open, functional, and well positioned at the heart of the home, allowing the next owner to enjoy it as is or make it their own. The primary suite is generously sized, featuring its own fireplace, an oversized bathroom with large walk-in shower, extensive vanity space, and a huge custom closet. One of the most special features of this home is the attached in-law suite, with its own separate entrance while still remaining accessible from the main home. Complete with a living room, bedroom, full bathroom, and kitchenette, this apartment style space offers exceptional flexibility for multigenerational living, live in family, guests, or even potential income producing use. Outside, the screened pool and spa area is a true highlight. Beautifully integrated into the architecture of the home, this private outdoor setting offers a covered lanai, lush tropical landscaping, and a peaceful courtyard style feel that makes it easy to relax, entertain, and enjoy Florida living year-round. The large paver driveway and detached garage create an impressive amount of parking and enhance the home’s unique layout and curb appeal. All of this is located less than 1.5 miles from Rollins College, Park Avenue, downtown Winter Park, public access to the Winter Park Chain of Lakes, and all the dining, shopping, boating, and everyday convenience that make this area so desirable. This is more than just a home. It is a rare chance to enjoy the Winter Park lifestyle in a custom home full of character, flexibility, and lasting value.

5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite offers 3,851 square feet of living space, remarkable flexibility, and the kind of charm that simply cannot be replicated. Buyers will also appreciate the peace of mind that comes with major recent updates, including a metal roof installed in 2017, two HVAC units replaced in 2026, a third HVAC unit replaced in 2022, and two water heaters installed in 2025. The pool was resurfaced in 2025, the exterior and interior of the home was painted in 2025, & the house has also been completely re-plumbed! From the moment you arrive, the home makes a lasting impression with its large brick front porch, circular driveway, mature landscaping, detached oversized 2 car garage, and classic architectural presence. Large windows and thoughtfully designed living spaces fill the home with natural light, while hardwood floors, custom built-ins, plantation shutters, fireplaces, and refined traditional details create a warm and inviting feel throughout. This is the perfect blend of classic Winter Park charm and functional modern updates. The floor plan offers both elegance and versatility. In addition to five bedrooms, the home features an office space that can also serve as a formal living room, library, or flex space depending on your needs. The spacious family room is anchored by one of the home’s two wood burning fireplaces and opens beautifully to the outdoor living area, creating an easy flow for both everyday living and entertaining. The kitchen offers granite countertops, custom cabinetry, abundant counter space, a large island, and lots of natural light. It is open, functional, and well positioned at the heart of the home, allowing the next owner to enjoy it as is or make it their own. The primary suite is generously sized, featuring its own fireplace, an oversized bathroom with large walk-in shower, extensive vanity space, and a huge custom closet. One of the most special features of this home is the attached in-law suite, with its own separate entrance while still remaining accessible from the main home. Complete with a living room, bedroom, full bathroom, and kitchenette, this apartment style space offers exceptional flexibility for multigenerational living, live in family, guests, or even potential income producing use. Outside, the screened pool and spa area is a true highlight. Beautifully integrated into the architecture of the home, this private outdoor setting offers a covered lanai, lush tropical landscaping, and a peaceful courtyard style feel that makes it easy to relax, entertain, and enjoy Florida living year-round. The large paver driveway and detached garage create an impressive amount of parking and enhance the home’s unique layout and curb appeal. All of this is located less than 1.5 miles from Rollins College, Park Avenue, downtown Winter Park, public access to the Winter Park Chain of Lakes, and all the dining, shopping, boating, and everyday convenience that make this area so desirable. This is more than just a home. It is a rare chance to enjoy the Winter Park lifestyle in a custom home full of character, flexibility, and lasting value.

1560 Woodland Avenue, Winter Park

$560,000

Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new windows (2019) a renovated primary bedroom and bath (2019), new septic drainfield (2023), tankless water heater (2019), new refrigerator (2024) and in ground pool converted to saltwater in 2023. A rare opportunity to own a classic Winter Park home in beautiful condition with modern improvements and exceptional outdoor living. Walk to Hunger Street Tacos, Lombardi’s Seafood and Creative Jane Art Studio while being conveniently located near 1-4, College Park and Winter Park. Come see this gem!

3 Beds ⋅ 2 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code

Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new windows (2019) a renovated primary bedroom and bath (2019), new septic drainfield (2023), tankless water heater (2019), new refrigerator (2024) and in ground pool converted to saltwater in 2023. A rare opportunity to own a classic Winter Park home in beautiful condition with modern improvements and exceptional outdoor living. Walk to Hunger Street Tacos, Lombardi’s Seafood and Creative Jane Art Studio while being conveniently located near 1-4, College Park and Winter Park. Come see this gem!

218 Orange Terrace Drive, Winter Park

$2,200,000

Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s exclusive Chain of Lakes-Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, Lake Nina, and Lake Minnehaha. Morning sunrises and golden afternoon sunsets create unforgettable moments to enjoy privately or share with family and friends. Built in 2008, this exceptional home welcomes you with a stunning rotunda accented by stained glass panels, setting the tone for the refined design found throughout. Vaulted recessed ceilings enhance the open floor plan, filling the home with natural light and architectural elegance. Thoughtfully curated details and custom finishes are showcased in every space. Offering approximately 5,051 square feet, the home features four spacious bedrooms, each with its own en suite bathroom. The owner’s suite is a private retreat with picturesque canal views and luxurious built-in features. The spa-inspired owner’s bath includes dual vanities, designer textiles, strategic lighting, expansive walk-in closets, a steam shower with dual stations and multiple shower heads, a Jacuzzi tub, bidet, linen storage,and a private water closet. Designed for effortless entertaining, the gourmet chef’s kitchen is both functional and beautiful. Highlights include an oversized working island, high-top bar seating,Thermador gas range,Thermadore double ovens,Thermadore refrigerator, wine cooler, hidden lighted walk-in pantry and multiple prep areas. The kitchen flows seamlessly into the formal dining room and the expansive great room, which showcases floor-to-ceiling views of the lushly landscaped backyard, paver patio and serene Venetian Canal water view. A stunning library with floor-to-ceiling canal views features a custom gas fireplace and built-in shelving, perfect for displaying books and treasured collections. The first floor features a convenient half bath adjacent to the laundry room, along with a lovely powder room ideal for guests. Upstairs, a striking staircase leads to three additional bedrooms and two bathrooms. One bedroom room has a private en-suite bathroom and the other bedrooms share an adjoining en- suite bath. There are two oversized, versatile gathering spaces complete with a built-in wet bar and beverage refrigerator. A spacious living area overlooks the canal and opens to an upper-level lanai-ideal for outdoor entertaining. This level also includes a home theater and flexible space suitable for an additional bedroom, office, or recreation room. Location is unmatched. Situated in the heart of Winter Park, this home offers easy access to both Winter Park and Maitland amenities. Enjoy Park Avenue dining, shopping, art festivals, farmers markets, outdoor concerts, scenic walking and biking trails, and beautiful green spaces. Zoned for top rated OCPS schools: Dommerich Elementary, Maitland Middle School, and Winter Park High School. This remarkable Winter Park Canal home combines timeless style, exceptional craftsmanship, private dock access, Venetian Canal frontage, and direct connection to the Winter Park Chain of Lakes-all in one of Central Florida’s most sought-after locations.

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s exclusive Chain of Lakes-Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, Lake Nina, and Lake Minnehaha. Morning sunrises and golden afternoon sunsets create unforgettable moments to enjoy privately or share with family and friends. Built in 2008, this exceptional home welcomes you with a stunning rotunda accented by stained glass panels, setting the tone for the refined design found throughout. Vaulted recessed ceilings enhance the open floor plan, filling the home with natural light and architectural elegance. Thoughtfully curated details and custom finishes are showcased in every space. Offering approximately 5,051 square feet, the home features four spacious bedrooms, each with its own en suite bathroom. The owner’s suite is a private retreat with picturesque canal views and luxurious built-in features. The spa-inspired owner’s bath includes dual vanities, designer textiles, strategic lighting, expansive walk-in closets, a steam shower with dual stations and multiple shower heads, a Jacuzzi tub, bidet, linen storage,and a private water closet. Designed for effortless entertaining, the gourmet chef’s kitchen is both functional and beautiful. Highlights include an oversized working island, high-top bar seating,Thermador gas range,Thermadore double ovens,Thermadore refrigerator, wine cooler, hidden lighted walk-in pantry and multiple prep areas. The kitchen flows seamlessly into the formal dining room and the expansive great room, which showcases floor-to-ceiling views of the lushly landscaped backyard, paver patio and serene Venetian Canal water view. A stunning library with floor-to-ceiling canal views features a custom gas fireplace and built-in shelving, perfect for displaying books and treasured collections. The first floor features a convenient half bath adjacent to the laundry room, along with a lovely powder room ideal for guests. Upstairs, a striking staircase leads to three additional bedrooms and two bathrooms. One bedroom room has a private en-suite bathroom and the other bedrooms share an adjoining en- suite bath. There are two oversized, versatile gathering spaces complete with a built-in wet bar and beverage refrigerator. A spacious living area overlooks the canal and opens to an upper-level lanai-ideal for outdoor entertaining. This level also includes a home theater and flexible space suitable for an additional bedroom, office, or recreation room. Location is unmatched. Situated in the heart of Winter Park, this home offers easy access to both Winter Park and Maitland amenities. Enjoy Park Avenue dining, shopping, art festivals, farmers markets, outdoor concerts, scenic walking and biking trails, and beautiful green spaces. Zoned for top rated OCPS schools: Dommerich Elementary, Maitland Middle School, and Winter Park High School. This remarkable Winter Park Canal home combines timeless style, exceptional craftsmanship, private dock access, Venetian Canal frontage, and direct connection to the Winter Park Chain of Lakes-all in one of Central Florida’s most sought-after locations.

2550 Venetian Way, Winter Park

$574,900

Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!

3 Beds ⋅ 2 Baths ⋅ Metzingers Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!

1354 Indiana Avenue, Winter Park

$1,649,000

PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

5 Beds ⋅ 4 Baths ⋅ Parklando #3 SubDv. ⋅ 32789 Zip Code

PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

2501 Winter Park Road, Winter Park

$6,900,000

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

6 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

1260 Alabama Drive, Winter Park