Homesinorlando.forsale Search Results

$570,000

One or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake Killarney, this impeccably remodeled two-story residence offers a rare opportunity to enjoy waterfront living with unmatched convenience. Just steps from Hillstone, Trader Joe’s, and Winter Park Village, this 2-bedroom, 2.5-bathroom home is the perfect blend of modern sophistication and timeless charm. Inside, you’ll find a beautifully designed open-concept kitchen ideal for entertaining, two spacious primary suites—each with its own spa-inspired en-suite bathroom—and a bonus office space with sweeping lake views that make working from home feel like a retreat. From top to bottom, every detail has been thoughtfully curated for both comfort and style. Step outside to your private covered patio and soak in postcard-worthy sunsets, or head down to the dock for a quiet moment by the water. The community offers a serene lakeside pool, very low HOA fees, and a laid-back lifestyle just minutes from some of Winter Park’s best shopping and dining. Come discover a one-of-a-kind home where lakefront tranquility meets urban convenience—this is Winter Park's best kept secret.

2 Beds ⋅ 3 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake Killarney, this impeccably remodeled two-story residence offers a rare opportunity to enjoy waterfront living with unmatched convenience. Just steps from Hillstone, Trader Joe’s, and Winter Park Village, this 2-bedroom, 2.5-bathroom home is the perfect blend of modern sophistication and timeless charm. Inside, you’ll find a beautifully designed open-concept kitchen ideal for entertaining, two spacious primary suites—each with its own spa-inspired en-suite bathroom—and a bonus office space with sweeping lake views that make working from home feel like a retreat. From top to bottom, every detail has been thoughtfully curated for both comfort and style. Step outside to your private covered patio and soak in postcard-worthy sunsets, or head down to the dock for a quiet moment by the water. The community offers a serene lakeside pool, very low HOA fees, and a laid-back lifestyle just minutes from some of Winter Park’s best shopping and dining. Come discover a one-of-a-kind home where lakefront tranquility meets urban convenience—this is Winter Park's best kept secret.

640 Killarney Bay Court Unit 4, Winter Park

$2,440,000

One lucky Buyer's gain is this Seller's bittersweet goodbye. A job relocation has these homeowners leaving behind a home they absolutely love, and now, you can make 1700 Palm Ave. yours! Modern sophistication and everyday functionality come together seamlessly in this exceptional Winter Park residence. With 3,770 square feet of thoughtfully designed living space, this 4-bedroom, 4.1-bath home offers a fantastic floorplan featuring a first-floor primary suite, private office, and a striking two-story great room filled with soft natural light from the south-facing backyard. Upstairs, a generous loft/bonus room accompanies three en-suite bedrooms, including a second suite designed as an alternate primary, complete with a private balcony, dual walk-in closets, and a dedicated water closet. The smart three-way split bedroom configuration enhances privacy and flexibility, while the first-floor primary suite features two large walk-in closets and a stackable washer and dryer for added convenience. The open-concept layout flows effortlessly to the covered lanai, complete with electronic roll-down screens, two beverage refrigerators, and a gas grill—overlooking a sleek saltwater pool framed by gray and white marble pavers. Tall sliding glass doors stack to create a seamless indoor-outdoor living experience, perfect for entertaining. Lush, mature podocarpus hedges and Japanese blueberry trees line the perimeter, offering a private and polished backdrop. The chef’s kitchen is outfitted with top-of-the-line Viking appliances, a gas cooktop, quartz countertops, and a walk-in pantry. A spacious island with a beverage fridge and generous storage complements the adjacent dining area, which comfortably seats eight, with room to expand for larger gatherings. Custom electronic roller shades add privacy and a clean, modern aesthetic, electronic/rechargeable blinds throughout the first floor and matching manual blinds upstairs. Wide-plank oak floors extend throughout the main level and up the architectural floating staircase. The oversized garage is equally well-appointed, featuring two storage closets and a built-in rack system. Ideally located just minutes from Winter Park’s renowned shops and dining on Park Avenue. The home is zoned for top-rated WP schools, including Winter Park High, Maitland Middle, and Lakemont Elementary. Looking to join a tennis league or spend afternoons on the golf course? This home is surrounded by both public and private clubs for social and athletic enjoyment. 1700 Palm Ave. delivers fabulous living in one of Central Florida’s most coveted neighborhoods.

4 Beds ⋅ 5 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

One lucky Buyer's gain is this Seller's bittersweet goodbye. A job relocation has these homeowners leaving behind a home they absolutely love, and now, you can make 1700 Palm Ave. yours! Modern sophistication and everyday functionality come together seamlessly in this exceptional Winter Park residence. With 3,770 square feet of thoughtfully designed living space, this 4-bedroom, 4.1-bath home offers a fantastic floorplan featuring a first-floor primary suite, private office, and a striking two-story great room filled with soft natural light from the south-facing backyard. Upstairs, a generous loft/bonus room accompanies three en-suite bedrooms, including a second suite designed as an alternate primary, complete with a private balcony, dual walk-in closets, and a dedicated water closet. The smart three-way split bedroom configuration enhances privacy and flexibility, while the first-floor primary suite features two large walk-in closets and a stackable washer and dryer for added convenience. The open-concept layout flows effortlessly to the covered lanai, complete with electronic roll-down screens, two beverage refrigerators, and a gas grill—overlooking a sleek saltwater pool framed by gray and white marble pavers. Tall sliding glass doors stack to create a seamless indoor-outdoor living experience, perfect for entertaining. Lush, mature podocarpus hedges and Japanese blueberry trees line the perimeter, offering a private and polished backdrop. The chef’s kitchen is outfitted with top-of-the-line Viking appliances, a gas cooktop, quartz countertops, and a walk-in pantry. A spacious island with a beverage fridge and generous storage complements the adjacent dining area, which comfortably seats eight, with room to expand for larger gatherings. Custom electronic roller shades add privacy and a clean, modern aesthetic, electronic/rechargeable blinds throughout the first floor and matching manual blinds upstairs. Wide-plank oak floors extend throughout the main level and up the architectural floating staircase. The oversized garage is equally well-appointed, featuring two storage closets and a built-in rack system. Ideally located just minutes from Winter Park’s renowned shops and dining on Park Avenue. The home is zoned for top-rated WP schools, including Winter Park High, Maitland Middle, and Lakemont Elementary. Looking to join a tennis league or spend afternoons on the golf course? This home is surrounded by both public and private clubs for social and athletic enjoyment. 1700 Palm Ave. delivers fabulous living in one of Central Florida’s most coveted neighborhoods.

1700 Palm Avenue, Winter Park

$175,000

Under contract-accepting backup offers. This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.

2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.

2500 Lee Road Unit 208, Winter Park

$792,500

Nestled within the tranquil confines of the Virginia Heights neighborhood lies a truly exceptional property that blends luxury, practicality, and location. Boasting three bedrooms and two and a half bathrooms, this residence offers a refined living experience with exclusive access to a private lakefront park—a serene retreat for relaxing or enjoying nature. Recently updated with brand-new luxury vinyl plank flooring throughout, the interior exudes sophistication, from the chef’s kitchen with custom wood cabinetry, granite countertops, and a walk-in butler’s pantry to the thoughtfully designed living spaces illuminated by designer lighting and anchored by an elegant spiral staircase with decorative wrought iron. Residents will appreciate the convenience of walking to the Winter Park Tennis Center, Park Avenue, Azalea Playground Park, and the vibrant Orange Avenue shops and dining. The home also features a private south-facing screened atrium ideal for entertaining or quiet mornings, as well as a spacious rooftop terrace with a heated and cooled bonus room offering endless flexibility. Tucked away from the street for added privacy, the building has recently undergone significant upgrades including a fresh exterior paint job and a brand-new roof. Casa Jardin also provides easy access to Lake Virginia, with amenities like paddle board and kayak storage racks that enhance the active Winter Park lifestyle. This home is a rare opportunity to enjoy elegance, convenience, and tranquility all in one coveted location.

3 Beds ⋅ 3 Baths ⋅ Casa Jardin Condo SubDv. ⋅ 32789 Zip Code

Nestled within the tranquil confines of the Virginia Heights neighborhood lies a truly exceptional property that blends luxury, practicality, and location. Boasting three bedrooms and two and a half bathrooms, this residence offers a refined living experience with exclusive access to a private lakefront park—a serene retreat for relaxing or enjoying nature. Recently updated with brand-new luxury vinyl plank flooring throughout, the interior exudes sophistication, from the chef’s kitchen with custom wood cabinetry, granite countertops, and a walk-in butler’s pantry to the thoughtfully designed living spaces illuminated by designer lighting and anchored by an elegant spiral staircase with decorative wrought iron. Residents will appreciate the convenience of walking to the Winter Park Tennis Center, Park Avenue, Azalea Playground Park, and the vibrant Orange Avenue shops and dining. The home also features a private south-facing screened atrium ideal for entertaining or quiet mornings, as well as a spacious rooftop terrace with a heated and cooled bonus room offering endless flexibility. Tucked away from the street for added privacy, the building has recently undergone significant upgrades including a fresh exterior paint job and a brand-new roof. Casa Jardin also provides easy access to Lake Virginia, with amenities like paddle board and kayak storage racks that enhance the active Winter Park lifestyle. This home is a rare opportunity to enjoy elegance, convenience, and tranquility all in one coveted location.

1276 S Pennsylvania Avenue Unit 12, Winter Park

$2,625,000

Step into luxury with this stunning three-story townhouse featuring an elevator and abundant natural light. A breathtaking staircase elegantly wraps around a magnificent chandelier, creating a striking focal point from the first floor to the third. The first floor boasts a chef's kitchen with high-end cabinets, top-of-the-line appliances, and premium flooring. The second floor offers four elegant main suites, each designed for comfort and privacy. The third floor is home to the impressive main suite, located next to the rooftop terrace, which includes a gazebo and jacuzzi. This home is equipped with an internal vacuum system and a state-of-the-art Pelican water filtration system for ultimate convenience and water quality. A charming backyard garden, a two-car garage, and a prime location within walking distance to top restaurants, parks, and farmer's market complete this exquisite property- ideal for stylish buyers seeking a vibrant lifestyle.

4 Beds ⋅ 6 Baths ⋅ Virginia & Morse Brownstones SubDv. ⋅ 32789 Zip Code

Step into luxury with this stunning three-story townhouse featuring an elevator and abundant natural light. A breathtaking staircase elegantly wraps around a magnificent chandelier, creating a striking focal point from the first floor to the third. The first floor boasts a chef's kitchen with high-end cabinets, top-of-the-line appliances, and premium flooring. The second floor offers four elegant main suites, each designed for comfort and privacy. The third floor is home to the impressive main suite, located next to the rooftop terrace, which includes a gazebo and jacuzzi. This home is equipped with an internal vacuum system and a state-of-the-art Pelican water filtration system for ultimate convenience and water quality. A charming backyard garden, a two-car garage, and a prime location within walking distance to top restaurants, parks, and farmer's market complete this exquisite property- ideal for stylish buyers seeking a vibrant lifestyle.

141 N Virginia Avenue, Winter Park

$3,600,000

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler’s pantry—ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout.

4 Beds ⋅ 4 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler’s pantry—ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout.

851 Georgia Avenue, Winter Park

$362,500

Priced to sell!! Motivated Seller. Outstanding structural integrity, no big assessments ahead! Whispering Waters passed its structural integrity inspection and reserves study with flying colors—earning compliments for the quality and care of the buildings. This is a very well-managed community, and the $1,054 monthly HOA covers nearly everything, including electricity! The only exception is cable and internet, making this an incredible value with true peace of mind. Tucked away just two blocks from Park Avenue, this one bedroom, one bathroom corner unit places you in the heart of downtown Winter Park—steps from acclaimed restaurants, charming shops, and the iconic boat tour on Lake Osceola. Situated on the second floor of Building 6 with convenient elevator access, this light filled condo has brand new carpet in the living areas and bedroom, creating a fresh and cozy feel. The kitchen features granite countertops, a built-in oven, glass cooktop, stainless steel refrigerator, and recently painted blue, solid wood cabinetry that adds a fun pop of color to the space. A dedicated dining area is located just off the kitchen and includes sliding glass doors that open to a small private balcony overlooking Morse Blvd—perfect for enjoying your morning coffee. Off the living room, an enclosed sunroom offers bonus living space with abundant natural light, motorized custom blinds, and upgraded windows for improved energy efficiency and sound insulation. The oversized bedroom offers space for a sitting area and features motorized shades for added comfort and privacy. A convenient door allows you to close off the bedroom —ideal for when guests are visiting and need access to the bathroom without entering the bedroom. The unit also comes with one assigned parking space in the garage, additional storage, and the peace of mind that HOA covers electric, water, sewer, trash, building insurance, pool maintenance, landscaping, and on-site management. Whispering Waters is a lakefront community on beautiful Lake Osceola, with water access available to residents—bring your kayak, soak in the serene views, or enjoy a sunset by the water. Whether you're seeking a full-time residence or a part-time getaway, this home offers effortless, low-maintenance living—just lock and leave. Bonus: Since the current owner is under 55, the next buyer can be too (only 85% of residents need to meet the 55+ age requirement). Call today to schedule your private showing!

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Priced to sell!! Motivated Seller. Outstanding structural integrity, no big assessments ahead! Whispering Waters passed its structural integrity inspection and reserves study with flying colors—earning compliments for the quality and care of the buildings. This is a very well-managed community, and the $1,054 monthly HOA covers nearly everything, including electricity! The only exception is cable and internet, making this an incredible value with true peace of mind. Tucked away just two blocks from Park Avenue, this one bedroom, one bathroom corner unit places you in the heart of downtown Winter Park—steps from acclaimed restaurants, charming shops, and the iconic boat tour on Lake Osceola. Situated on the second floor of Building 6 with convenient elevator access, this light filled condo has brand new carpet in the living areas and bedroom, creating a fresh and cozy feel. The kitchen features granite countertops, a built-in oven, glass cooktop, stainless steel refrigerator, and recently painted blue, solid wood cabinetry that adds a fun pop of color to the space. A dedicated dining area is located just off the kitchen and includes sliding glass doors that open to a small private balcony overlooking Morse Blvd—perfect for enjoying your morning coffee. Off the living room, an enclosed sunroom offers bonus living space with abundant natural light, motorized custom blinds, and upgraded windows for improved energy efficiency and sound insulation. The oversized bedroom offers space for a sitting area and features motorized shades for added comfort and privacy. A convenient door allows you to close off the bedroom —ideal for when guests are visiting and need access to the bathroom without entering the bedroom. The unit also comes with one assigned parking space in the garage, additional storage, and the peace of mind that HOA covers electric, water, sewer, trash, building insurance, pool maintenance, landscaping, and on-site management. Whispering Waters is a lakefront community on beautiful Lake Osceola, with water access available to residents—bring your kayak, soak in the serene views, or enjoy a sunset by the water. Whether you're seeking a full-time residence or a part-time getaway, this home offers effortless, low-maintenance living—just lock and leave. Bonus: Since the current owner is under 55, the next buyer can be too (only 85% of residents need to meet the 55+ age requirement). Call today to schedule your private showing!

311 E Morse Boulevard Unit 6-7, Winter Park

$602,500

This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic charm and modern convenience in a highly desirable location. The open floor plan is warm and inviting, with stylish finishes and thoughtful updates that make it truly move-in ready. Each bedroom features its own ensuite bath and a spacious walk-in closet, with both upstairs suites offering the flexibility to serve as a primary retreat. Recent improvements include a brand new hot water heater, new refrigerator, an added mini-split in the garage for enhanced comfort, a water softener system, and a recently replaced A/C. The fenced backyard has been upgraded to turf for easy maintenance, complemented by a private deck—perfect for relaxing or entertaining. Two balconies, including one with a view of the Rollins College baseball field, provide additional peaceful retreats. The attached two-car garage offers both convenience and extra security. Located within walking distance of Park Avenue, Rollins College, and Hannibal Square, this home provides easy access to shopping, dining, and entertainment while maintaining a quiet and private feel. A rare opportunity in an unbeatable location—don’t miss it!

3 Beds ⋅ 3 Baths ⋅ Arbors/Aragon SubDv. ⋅ 32789 Zip Code

This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic charm and modern convenience in a highly desirable location. The open floor plan is warm and inviting, with stylish finishes and thoughtful updates that make it truly move-in ready. Each bedroom features its own ensuite bath and a spacious walk-in closet, with both upstairs suites offering the flexibility to serve as a primary retreat. Recent improvements include a brand new hot water heater, new refrigerator, an added mini-split in the garage for enhanced comfort, a water softener system, and a recently replaced A/C. The fenced backyard has been upgraded to turf for easy maintenance, complemented by a private deck—perfect for relaxing or entertaining. Two balconies, including one with a view of the Rollins College baseball field, provide additional peaceful retreats. The attached two-car garage offers both convenience and extra security. Located within walking distance of Park Avenue, Rollins College, and Hannibal Square, this home provides easy access to shopping, dining, and entertainment while maintaining a quiet and private feel. A rare opportunity in an unbeatable location—don’t miss it!

777 S Denning Drive Unit B, Winter Park

$2,800,000

Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthouse residence, perfectly positioned in the charming brick-lined streets of Winter Park. While nestled in the heart of the city's vibrant dining, shopping, and cultural scene, this exclusive retreat offers unparalleled tranquility and seclusion. Designed for those who appreciate sophistication, this secured building boasts lavish amenities that extend your living space beyond the walls of your penthouse. Host guests in the elegant resident lounge, complete with a bar for entertaining, marvel at rocket launches from the spectacular rooftop terrace, or take advantage of the private conference room, ideal for high-level meetings or remote work. Stay active in the state-of-the-art exercise room, offering convenience and wellness steps from your front door. With private, secured covered parking and concierge-level service, every detail has been designed to elevate your lifestyle. Inside, refined elegance meets cutting-edge technology—custom millwork, exquisite tile work, and smart-home automation blend seamlessly with high-end video conferencing capabilities. Expansive living spaces, soaring ceilings, and generous room sizes create an inviting atmosphere, while every bedroom features a spa-like ensuite and a private balcony to take in the beauty of Winter Park. Enjoy world-class restaurants, boutique shopping, and lively events at the park, all just steps from your front door. With the nearby train station providing effortless access to Orlando and even Miami, your next adventure is always within reach. This penthouse is a rare opportunity—luxury, location, and lifestyle converge in perfect harmony. Schedule your private tour today!

3 Beds ⋅ 4 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code

Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthouse residence, perfectly positioned in the charming brick-lined streets of Winter Park. While nestled in the heart of the city's vibrant dining, shopping, and cultural scene, this exclusive retreat offers unparalleled tranquility and seclusion. Designed for those who appreciate sophistication, this secured building boasts lavish amenities that extend your living space beyond the walls of your penthouse. Host guests in the elegant resident lounge, complete with a bar for entertaining, marvel at rocket launches from the spectacular rooftop terrace, or take advantage of the private conference room, ideal for high-level meetings or remote work. Stay active in the state-of-the-art exercise room, offering convenience and wellness steps from your front door. With private, secured covered parking and concierge-level service, every detail has been designed to elevate your lifestyle. Inside, refined elegance meets cutting-edge technology—custom millwork, exquisite tile work, and smart-home automation blend seamlessly with high-end video conferencing capabilities. Expansive living spaces, soaring ceilings, and generous room sizes create an inviting atmosphere, while every bedroom features a spa-like ensuite and a private balcony to take in the beauty of Winter Park. Enjoy world-class restaurants, boutique shopping, and lively events at the park, all just steps from your front door. With the nearby train station providing effortless access to Orlando and even Miami, your next adventure is always within reach. This penthouse is a rare opportunity—luxury, location, and lifestyle converge in perfect harmony. Schedule your private tour today!

315 E New England Avenue Unit 30, Winter Park

$5,400,000

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

5 Beds ⋅ 9 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

1400 Alabama Drive, Winter Park

$4,273,211

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in main house plus detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform TWELVE kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry, and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here, with a sculptural installation of galvanized steel surrounding a crepe myrtle, accompanied by a matching bike rack. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool and spa, while a custom cedar hot tub blends into the landscape. A wood-clad pergola shelters the outdoor kitchen, featuring a Röshults system with a professional-grade grill, sink and storage. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

4 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in main house plus detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform TWELVE kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry, and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here, with a sculptural installation of galvanized steel surrounding a crepe myrtle, accompanied by a matching bike rack. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool and spa, while a custom cedar hot tub blends into the landscape. A wood-clad pergola shelters the outdoor kitchen, featuring a Röshults system with a professional-grade grill, sink and storage. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park

$480,000

NO HOA! Beautifully Remodeled Home with Expansive Garden in Winter Park Welcome to this charming and fully remodeled two-story, 3-bedroom, 3-bathroom home nestled in the heart of Winter Park. Offering a blend of modern upgrades and historic charm, this property is surrounded by a vibrant community with easy access to top destinations. Prime Location: 5 minutes to Whole Foods and Trader Joe’s 8 minutes to Downtown Orlando via I-4 (Exits 87 & 88) Surrounded by Winter Park’s historic charm Private library with an excellent book collection Weekly Farmers’ Market just minutes away Extensively Renovated in 2019: New Roof, New Windows, New A/C New Electrical Wiring & Plumbing New Driveway & Fully Fenced Yard with Entry Gate New Porch & Open-Concept Kitchen Versatile Living Space: This single-family home offers flexible living arrangements and can also function as a duplex: Downstairs: 1 bed, 1 bath, spacious living room with modern kitchen combo Upstairs: 2 beds, 2 baths, large family room, and a covered porch with scenic views Outdoor space on the porch for entertaining All permits are available on the Orange County Property Permit website for complete peace of mind. Don't miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location! Contact us today for a private showing.

3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

NO HOA! Beautifully Remodeled Home with Expansive Garden in Winter Park Welcome to this charming and fully remodeled two-story, 3-bedroom, 3-bathroom home nestled in the heart of Winter Park. Offering a blend of modern upgrades and historic charm, this property is surrounded by a vibrant community with easy access to top destinations. Prime Location: 5 minutes to Whole Foods and Trader Joe’s 8 minutes to Downtown Orlando via I-4 (Exits 87 & 88) Surrounded by Winter Park’s historic charm Private library with an excellent book collection Weekly Farmers’ Market just minutes away Extensively Renovated in 2019: New Roof, New Windows, New A/C New Electrical Wiring & Plumbing New Driveway & Fully Fenced Yard with Entry Gate New Porch & Open-Concept Kitchen Versatile Living Space: This single-family home offers flexible living arrangements and can also function as a duplex: Downstairs: 1 bed, 1 bath, spacious living room with modern kitchen combo Upstairs: 2 beds, 2 baths, large family room, and a covered porch with scenic views Outdoor space on the porch for entertaining All permits are available on the Orange County Property Permit website for complete peace of mind. Don't miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location! Contact us today for a private showing.

423 Ololu Drive, Winter Park

$1,877,500

Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads you to its impressive facade. The home has been thoughtfully updated with fresh interior and exterior paint, along with the addition of three new HVAC systems, ensuring modern comfort throughout. Boasting over 4,000 square feet of living space, the home features five generously sized bedrooms, including a second-floor Primary Suite that offers both luxury and privacy. The suite is complete with a private sitting area, a terrace overlooking the lushly landscaped grounds, and a spa-like bath with dual sinks, jetted tub, and a walk-in shower. A spacious walk-in closet provides ample storage space and custom built-ins. In addition to the three bedrooms, the second-floor features a spearate bonus room that is perfect for a private office, or could be converted to an in-law/guest suite, adding versatile living space to the property. The chef’s kitchen is a culinary dream, featuring solid wood 42” cabinetry, elegant granite countertops and a new subway tile backsplash. Adding to the Kitchen's functionality and sophistication are Copper prep and main sinks, Wolf Natural Gas Range, dual dishwashers, under counter ice maker and a walk-in pantry, A separate casual dining space and an island/breakfast bar seamlessly open into the family room, creating an ideal setting for everyday living and entertaining. Off the Kitchen and family room is a full guest bathroom with built in desk area and a multifunctional game room that could convert to a 6th bedroom. Outside, the private oasis is designed for both relaxation and entertainment. A resort-style pool with tranquil fountains serves as the centerpiece, while a beautifully crafted Spanish styled privacy wall, accented with lighting and peaceful bamboo, offers a serene atmosphere. Enjoy the cooler evening relaxing around the piped natural gas fire pit. Enjoy the expansive Cabana area includes a summer kitchen, as well as dedicated seating and dining areas, all overlooking the pool and lush landscaping. With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods.

5 Beds ⋅ 6 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads you to its impressive facade. The home has been thoughtfully updated with fresh interior and exterior paint, along with the addition of three new HVAC systems, ensuring modern comfort throughout. Boasting over 4,000 square feet of living space, the home features five generously sized bedrooms, including a second-floor Primary Suite that offers both luxury and privacy. The suite is complete with a private sitting area, a terrace overlooking the lushly landscaped grounds, and a spa-like bath with dual sinks, jetted tub, and a walk-in shower. A spacious walk-in closet provides ample storage space and custom built-ins. In addition to the three bedrooms, the second-floor features a spearate bonus room that is perfect for a private office, or could be converted to an in-law/guest suite, adding versatile living space to the property. The chef’s kitchen is a culinary dream, featuring solid wood 42” cabinetry, elegant granite countertops and a new subway tile backsplash. Adding to the Kitchen's functionality and sophistication are Copper prep and main sinks, Wolf Natural Gas Range, dual dishwashers, under counter ice maker and a walk-in pantry, A separate casual dining space and an island/breakfast bar seamlessly open into the family room, creating an ideal setting for everyday living and entertaining. Off the Kitchen and family room is a full guest bathroom with built in desk area and a multifunctional game room that could convert to a 6th bedroom. Outside, the private oasis is designed for both relaxation and entertainment. A resort-style pool with tranquil fountains serves as the centerpiece, while a beautifully crafted Spanish styled privacy wall, accented with lighting and peaceful bamboo, offers a serene atmosphere. Enjoy the cooler evening relaxing around the piped natural gas fire pit. Enjoy the expansive Cabana area includes a summer kitchen, as well as dedicated seating and dining areas, all overlooking the pool and lush landscaping. With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods.

1446 Berkshire Avenue, Winter Park

$224,999

Under contract-accepting backup offers. Virtually Staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool & Clubhouse overlooking Lake Killarney. You will love Paddle Boarding, Kayaking and Boating just steps from your door. Beautifully updated 2-bedroom, 2-bathroom condo located on the shores of Lake Killarney in highly desirable Winter Park. This immaculate home offers tranquil lakeside living and unbeatable convenience, minutes from Trader Joe’s, Park Avenue, Rollins College, and Downtown Orlando. The condo is upgraded throughout with New AC & Water Heater, New Interior Paint, New Lighting, New Ceiling Fans & Window Blinds, Updated Door Hardware, Primary Bathroom Renovation featuring new tile, modern vanity, and LED mirror, Upgraded Exterior Doors & Windows. Open-concept kitchen with wood cabinetry, granite countertops, a built-in wine rack, and breakfast bar, flows into the spacious living area and private balcony. Enjoy two private patio spaces front and rear, overlooking the courtyard, perfect for relaxing and entertaining. With only one neighbor to the side and one below, this unit offers enhanced privacy. Split-Bedroom Design, Two large bedrooms, each with walk-in closets. Primary suite includes a private exterior entrance and a fully renovated bathroom with walk-in shower. Second bathroom includes a tub/shower combo and tile flooring. Enhance your life living minutes from Park Avenue (shopping, dining, events), Rollins College (3 miles), Winter Park Village, I4 for easy commuting, Downtown Orlando, Orlando International Airport, Disney, and Universal (20–30 mins). Low HOA Includes Water & Trash, Cable & Internet, Lake Access & Dock, Pool & Clubhouse, and Designated Parking.

2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Condominium Association, Inc. SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Virtually Staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool & Clubhouse overlooking Lake Killarney. You will love Paddle Boarding, Kayaking and Boating just steps from your door. Beautifully updated 2-bedroom, 2-bathroom condo located on the shores of Lake Killarney in highly desirable Winter Park. This immaculate home offers tranquil lakeside living and unbeatable convenience, minutes from Trader Joe’s, Park Avenue, Rollins College, and Downtown Orlando. The condo is upgraded throughout with New AC & Water Heater, New Interior Paint, New Lighting, New Ceiling Fans & Window Blinds, Updated Door Hardware, Primary Bathroom Renovation featuring new tile, modern vanity, and LED mirror, Upgraded Exterior Doors & Windows. Open-concept kitchen with wood cabinetry, granite countertops, a built-in wine rack, and breakfast bar, flows into the spacious living area and private balcony. Enjoy two private patio spaces front and rear, overlooking the courtyard, perfect for relaxing and entertaining. With only one neighbor to the side and one below, this unit offers enhanced privacy. Split-Bedroom Design, Two large bedrooms, each with walk-in closets. Primary suite includes a private exterior entrance and a fully renovated bathroom with walk-in shower. Second bathroom includes a tub/shower combo and tile flooring. Enhance your life living minutes from Park Avenue (shopping, dining, events), Rollins College (3 miles), Winter Park Village, I4 for easy commuting, Downtown Orlando, Orlando International Airport, Disney, and Universal (20–30 mins). Low HOA Includes Water & Trash, Cable & Internet, Lake Access & Dock, Pool & Clubhouse, and Designated Parking.

2500 Lee Road Unit 202, Winter Park

$230,000

Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on Community deck! Private Boat Ramp on this Skiable Lake, limited Boat parking on property. 2 Bedroom 2 Bath second floor Unit has been meticulously maintained by Winter Resident. Furniture purchased in 2020. Many Updates to Unit include new windows and window treatments, 2024 new Hot Water Heater, Baths redone in 2018-2019, New Appliances within last 5 years. Spacious Room Sizes, Private Balcony. Perfect location! Easy walk to Shopping, Restaurants, Movie Theater, close to Park Avenue and Farmers Market, minutes to I-4. One of Winter Park's best kept secrets! Don't miss this opportunity to view and own in this lovely community!

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on Community deck! Private Boat Ramp on this Skiable Lake, limited Boat parking on property. 2 Bedroom 2 Bath second floor Unit has been meticulously maintained by Winter Resident. Furniture purchased in 2020. Many Updates to Unit include new windows and window treatments, 2024 new Hot Water Heater, Baths redone in 2018-2019, New Appliances within last 5 years. Spacious Room Sizes, Private Balcony. Perfect location! Easy walk to Shopping, Restaurants, Movie Theater, close to Park Avenue and Farmers Market, minutes to I-4. One of Winter Park's best kept secrets! Don't miss this opportunity to view and own in this lovely community!

1500 Gay Road Unit 10C, Winter Park

$1,950,000

Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area. This modern Mediterranean-inspired residence seamlessly blends timeless elegance with contemporary luxury, offering an exceptional living experience with high-end finishes, thoughtfully designed spaces, and unmatched attention to detail. Step inside to whitewashed oak wood and travertine flooring, setting the tone for a warm and sophisticated ambiance. The open floor plan begins with a private front office, ideal for remote work, and a guest suite with a full bath—perfect for visitors or multi-generational living. The first-floor primary suite serves as a private retreat, featuring direct access to the patio for a peaceful outdoor escape. The spa-like en-suite bathroom boasts dual vanities, a walk-in shower, and a freestanding soaking tub, while the custom-built walk-in closet offers elegant storage solutions. Thoughtful details, like built-in wiring for a wall-mounted TV, enhance both convenience and luxury. At the heart of the home is the gourmet kitchen, designed to impress with a solid walnut breakfast bar, quartzite, Carrara, and travertine countertops, Grohe faucets, and custom pullout/swivel cabinetry. A hidden pantry blends seamlessly into the custom cabinetry, while top-tier Thermador gas appliances, including a 42” refrigerator, make cooking a breeze. Flowing effortlessly into the family room and private courtyard, this space is perfect for entertaining. Upstairs, you'll find stunning Venetian plaster walls and a modern glass stair railing leading to a versatile loft space. Three additional bedrooms are located on this level, each featuring custom-built walk-in closets for optimal organization. One of the upstairs bedrooms includes a private en-suite, while the bonus loft opens to a covered balcony through elegant French doors, providing a tranquil indoor-outdoor retreat. Plush new carpeting in the bedrooms enhances the comfort and style of the upper level. Designed for seamless outdoor living, this home features a custom-built gas fire pit, summer kitchen, and outdoor grill, making it perfect for year-round entertaining. The expansive upstairs balcony offers additional entertainment space, large enough for a ping pong table, outdoor lounge, or media area. A two-car rear side-entry garage, connected to the main house by a charming esplanade walkway, offers both privacy and convenience while enhancing the home’s architectural beauty. The freshly painted exterior adds to the home’s pristine appeal, making it truly move-in ready. Located within one of Winter Park’s most desired school districts, this home is zoned for Audubon K-8 and Winter Park High School. Plus, you’re just minutes from East End Market and Park Avenue, with the area's finest dining, shopping, and cultural attractions. This is more than a home—it’s an expression of refined living and timeless design. Schedule your private tour today!

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

Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area. This modern Mediterranean-inspired residence seamlessly blends timeless elegance with contemporary luxury, offering an exceptional living experience with high-end finishes, thoughtfully designed spaces, and unmatched attention to detail. Step inside to whitewashed oak wood and travertine flooring, setting the tone for a warm and sophisticated ambiance. The open floor plan begins with a private front office, ideal for remote work, and a guest suite with a full bath—perfect for visitors or multi-generational living. The first-floor primary suite serves as a private retreat, featuring direct access to the patio for a peaceful outdoor escape. The spa-like en-suite bathroom boasts dual vanities, a walk-in shower, and a freestanding soaking tub, while the custom-built walk-in closet offers elegant storage solutions. Thoughtful details, like built-in wiring for a wall-mounted TV, enhance both convenience and luxury. At the heart of the home is the gourmet kitchen, designed to impress with a solid walnut breakfast bar, quartzite, Carrara, and travertine countertops, Grohe faucets, and custom pullout/swivel cabinetry. A hidden pantry blends seamlessly into the custom cabinetry, while top-tier Thermador gas appliances, including a 42” refrigerator, make cooking a breeze. Flowing effortlessly into the family room and private courtyard, this space is perfect for entertaining. Upstairs, you'll find stunning Venetian plaster walls and a modern glass stair railing leading to a versatile loft space. Three additional bedrooms are located on this level, each featuring custom-built walk-in closets for optimal organization. One of the upstairs bedrooms includes a private en-suite, while the bonus loft opens to a covered balcony through elegant French doors, providing a tranquil indoor-outdoor retreat. Plush new carpeting in the bedrooms enhances the comfort and style of the upper level. Designed for seamless outdoor living, this home features a custom-built gas fire pit, summer kitchen, and outdoor grill, making it perfect for year-round entertaining. The expansive upstairs balcony offers additional entertainment space, large enough for a ping pong table, outdoor lounge, or media area. A two-car rear side-entry garage, connected to the main house by a charming esplanade walkway, offers both privacy and convenience while enhancing the home’s architectural beauty. The freshly painted exterior adds to the home’s pristine appeal, making it truly move-in ready. Located within one of Winter Park’s most desired school districts, this home is zoned for Audubon K-8 and Winter Park High School. Plus, you’re just minutes from East End Market and Park Avenue, with the area's finest dining, shopping, and cultural attractions. This is more than a home—it’s an expression of refined living and timeless design. Schedule your private tour today!

141 Oakwood Way, Winter Park

$1,131,000

Easy condominium living in the Douglas Grand in downtown Winter Park this exclusive complex is beautifully constructed and maintained. This one-level corner unit features a split bedroom plan and is on the top floor of building to enjoy sweeping views of downtown Orlando and Rollins Chapel. Floor plan includes three bedrooms, three baths, with two private balconies from bedrooms, all in the desirable quadrant of Park Avenue. On the Virginia side of the complex, it is incredibly quiet, with a fully gated parking garage providing security. A short distance from the vibrant Park Avenue shopping and dining district, as well as Hannibal Square, every convenience is at your doorstep. Step inside to discover the 2,615-square-foot open floor plan with beautiful finishes, gorgeous wood floors with custom details throughout. Entertain with ease in the expansive gourmet kitchen, seamlessly connected to the dining and living areas. The kitchen features top-of-the-line appliances from Sub-Zero, Wolf and Bosch, custom 42-inch cabinetry, granite counters, task lighting and a closet pantry. Bar seating allows you to enjoy your guests when entertaining and overlooking the living space. Two primary bedrooms with en-suite baths feature updated dual vanities, separate showers and indulgent soaking tubs. A third bedroom or office offers versatility and functionality. Elevate your lifestyle with a host of modern amenities, including updated light fixtures and fans, new doors to outside balconies, renovated baths, fresh paint, plantation shutters that add an extra touch of elegance, and spacious walk-in closets that provide ample storage in every bedroom. Enjoy the added convenience of two deeded parking spaces in the gated attached garage, complete with direct access to the fourth floor. This unit is a short distance from the access door for the garage, making daily functions easy. Every aspect of luxury living has been meticulously curated for your enjoyment. Indulge in the unparalleled convenience of strolling to nearby restaurants, coffee shops and boutiques. Rollins College is nearby, as well as fabulous events in Central Park and the bustling farmers market. Don’t miss your chance to experience the pinnacle of urban sophistication at the Douglas Grand.

3 Beds ⋅ 3 Baths ⋅ Douglas Grand SubDv. ⋅ 32789 Zip Code

Easy condominium living in the Douglas Grand in downtown Winter Park this exclusive complex is beautifully constructed and maintained. This one-level corner unit features a split bedroom plan and is on the top floor of building to enjoy sweeping views of downtown Orlando and Rollins Chapel. Floor plan includes three bedrooms, three baths, with two private balconies from bedrooms, all in the desirable quadrant of Park Avenue. On the Virginia side of the complex, it is incredibly quiet, with a fully gated parking garage providing security. A short distance from the vibrant Park Avenue shopping and dining district, as well as Hannibal Square, every convenience is at your doorstep. Step inside to discover the 2,615-square-foot open floor plan with beautiful finishes, gorgeous wood floors with custom details throughout. Entertain with ease in the expansive gourmet kitchen, seamlessly connected to the dining and living areas. The kitchen features top-of-the-line appliances from Sub-Zero, Wolf and Bosch, custom 42-inch cabinetry, granite counters, task lighting and a closet pantry. Bar seating allows you to enjoy your guests when entertaining and overlooking the living space. Two primary bedrooms with en-suite baths feature updated dual vanities, separate showers and indulgent soaking tubs. A third bedroom or office offers versatility and functionality. Elevate your lifestyle with a host of modern amenities, including updated light fixtures and fans, new doors to outside balconies, renovated baths, fresh paint, plantation shutters that add an extra touch of elegance, and spacious walk-in closets that provide ample storage in every bedroom. Enjoy the added convenience of two deeded parking spaces in the gated attached garage, complete with direct access to the fourth floor. This unit is a short distance from the access door for the garage, making daily functions easy. Every aspect of luxury living has been meticulously curated for your enjoyment. Indulge in the unparalleled convenience of strolling to nearby restaurants, coffee shops and boutiques. Rollins College is nearby, as well as fabulous events in Central Park and the bustling farmers market. Don’t miss your chance to experience the pinnacle of urban sophistication at the Douglas Grand.

100 S Virginia Avenue Unit 401, Winter Park

$995,000

Custom-Built Home with Unique Features in a Prime Winter Park Location! Discover this extraordinary 5-bedroom, 4-bathroom custom-built home spanning 3,270sqft of thoughtfully designed living space, where innovation meets comfort. This residence is a masterpiece of modern construction, offering cutting-edge safety features, exceptional energy efficiency, and a coveted location near everything you need. From the moment you step inside, you’ll notice the attention to detail, with 6 Solartubes flooding the home with natural light to reduce energy usage and hurricane-proof windows providing unmatched storm protection. Built with ICF (Insulated Concrete Form), this home is hurricane-proof, energy-efficient, pest-resistant, and whisper-quiet, ensuring a safe and serene environment. The metal roof, coupled with a lightning protection system, adds durability and safety, while 4 Ring security cameras and home automation—including smart switches, blinds, and a Nest 3-zone system—deliver convenience and peace of mind. With a Green Home Energy Certificate, this eco-friendly residence boasts astonishingly low electricity bills of just $100-$150 per month for the entire house. Beyond the main living space, the home offers incredible versatility with an ADU (Accessory Dwelling Unit) that has a private entrance, its own full kitchen, washer, and dryer. This additional living space is perfect for rental income, guest accommodations, or multigenerational living. A separate shed provides even more storage options. Outdoors, enjoy breathtaking views from the 2nd and 3rd level balconies, an elevated lot for added safety against flooding, and the freedom of no HOA restrictions. Conveniently located, this home is just 2 minutes from I-4 for seamless commuting and 5 minutes from top grocery destinations like Publix, Trader Joe’s, and Whole Foods. Whether you’re searching for a luxurious forever home or a smart investment opportunity, this property is a rare blend of eco-friendly living, advanced technology, and timeless comfort. Don’t miss your chance to own this property!

5 Beds ⋅ 4 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Custom-Built Home with Unique Features in a Prime Winter Park Location! Discover this extraordinary 5-bedroom, 4-bathroom custom-built home spanning 3,270sqft of thoughtfully designed living space, where innovation meets comfort. This residence is a masterpiece of modern construction, offering cutting-edge safety features, exceptional energy efficiency, and a coveted location near everything you need. From the moment you step inside, you’ll notice the attention to detail, with 6 Solartubes flooding the home with natural light to reduce energy usage and hurricane-proof windows providing unmatched storm protection. Built with ICF (Insulated Concrete Form), this home is hurricane-proof, energy-efficient, pest-resistant, and whisper-quiet, ensuring a safe and serene environment. The metal roof, coupled with a lightning protection system, adds durability and safety, while 4 Ring security cameras and home automation—including smart switches, blinds, and a Nest 3-zone system—deliver convenience and peace of mind. With a Green Home Energy Certificate, this eco-friendly residence boasts astonishingly low electricity bills of just $100-$150 per month for the entire house. Beyond the main living space, the home offers incredible versatility with an ADU (Accessory Dwelling Unit) that has a private entrance, its own full kitchen, washer, and dryer. This additional living space is perfect for rental income, guest accommodations, or multigenerational living. A separate shed provides even more storage options. Outdoors, enjoy breathtaking views from the 2nd and 3rd level balconies, an elevated lot for added safety against flooding, and the freedom of no HOA restrictions. Conveniently located, this home is just 2 minutes from I-4 for seamless commuting and 5 minutes from top grocery destinations like Publix, Trader Joe’s, and Whole Foods. Whether you’re searching for a luxurious forever home or a smart investment opportunity, this property is a rare blend of eco-friendly living, advanced technology, and timeless comfort. Don’t miss your chance to own this property!

1975 Biscayne Drive, Winter Park

$2,599,000

Nestled in the exclusive, sought-after cul-de-sac of Via Tuscany Oaks, this estate offers a rare opportunity to own a premier piece of Winter Park real estate. Situated among only six other distinguished homes and surrounded by a meticulously landscaped central park, this property perfectly blends privacy, elegance, and an unmatched location. The chef’s kitchen is a masterpiece of both design and functionality, featuring custom copper sinks, exquisite marble countertops, and custom cabinetry—an ideal space for both intimate meals and large gatherings. Step outside to find an entertainer’s dream: a custom-built summer kitchen complete with a grill, wet bar, refrigerator, and kegerator. This outdoor space is designed for luxury living, with a pool bath, putting green, and outdoor shower, creating the perfect atmosphere for both relaxation and entertainment. The first-floor Master Suite is a true sanctuary, offering a serene retreat with a spacious spa-like bath that includes a steam shower, vaulted ceilings, and dual walk-in closets—providing both comfort and luxury. Upstairs, four additional bedrooms, two full baths, and a balcony overlooking the central park offer an abundance of space and tranquility, with a perfect balance of privacy and scenic views. Located just steps from the Winter Park Racquet Club and only a short stroll to the renowned Park Avenue, this home places you in the heart of everything Winter Park has to offer—award-winning dining, shopping, and cultural experiences.

5 Beds ⋅ 5 Baths ⋅ Via Tuscany Oaks 47/75 SubDv. ⋅ 32789 Zip Code

Nestled in the exclusive, sought-after cul-de-sac of Via Tuscany Oaks, this estate offers a rare opportunity to own a premier piece of Winter Park real estate. Situated among only six other distinguished homes and surrounded by a meticulously landscaped central park, this property perfectly blends privacy, elegance, and an unmatched location. The chef’s kitchen is a masterpiece of both design and functionality, featuring custom copper sinks, exquisite marble countertops, and custom cabinetry—an ideal space for both intimate meals and large gatherings. Step outside to find an entertainer’s dream: a custom-built summer kitchen complete with a grill, wet bar, refrigerator, and kegerator. This outdoor space is designed for luxury living, with a pool bath, putting green, and outdoor shower, creating the perfect atmosphere for both relaxation and entertainment. The first-floor Master Suite is a true sanctuary, offering a serene retreat with a spacious spa-like bath that includes a steam shower, vaulted ceilings, and dual walk-in closets—providing both comfort and luxury. Upstairs, four additional bedrooms, two full baths, and a balcony overlooking the central park offer an abundance of space and tranquility, with a perfect balance of privacy and scenic views. Located just steps from the Winter Park Racquet Club and only a short stroll to the renowned Park Avenue, this home places you in the heart of everything Winter Park has to offer—award-winning dining, shopping, and cultural experiences.

1000 Via Tuscany Oaks Way, Winter Park

$2,325,000

Welcome to this charming one owner home nestled on the shores of Lake Knowles in the heart of Winter Park, located in one of the most sought-after neighborhoods. This home truly has it all and is just steps from Winter Park Racquet Club and minutes to Winter Park’s Interlachen Country Club as well as coveted Park Avenue, that features many restaurants and shops. This 4-bedroom, 3.5 bath pool home has amazing curb appeal with incredible landscaping as well as unique features throughout that will make you never want to leave. From the minute you park, the car to the first step inside, this home will have you wanting to come back for more. As you walk inside, the foyer immediately informs you of the quality of the home. The family room opens into the kitchen and is the perfect place to entertain family or friends. The kitchen has incredible views of Lake Knowles, and kitchen cabinets have been freshly painted. The fireplace in the family room is surrounded by built-in cabinets which provide ample storage. The French doors that lead out to the pool area provide a tremendous amount of natural light. The downstairs is finished off by an office, an additional sitting room, a dining room and a half bath. Located upstairs, 2 bedrooms share a bathroom and have doors that lead out to the covered patio. The owner’s retreat features a fireplace, crown molding, a large walk-in closet and a large master bathroom. Now that we saved one of the best parts for last let’s make our way outside! The back porch overlooks the serene pool and the screen enclosure is perfect for keeping those pesky bugs away. The rear hedge provides wonderful privacy from rear neighbors. Don’t miss the opportunity to have incredible sunsets from your very own private balcony - call today to set up your private showing.

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Welcome to this charming one owner home nestled on the shores of Lake Knowles in the heart of Winter Park, located in one of the most sought-after neighborhoods. This home truly has it all and is just steps from Winter Park Racquet Club and minutes to Winter Park’s Interlachen Country Club as well as coveted Park Avenue, that features many restaurants and shops. This 4-bedroom, 3.5 bath pool home has amazing curb appeal with incredible landscaping as well as unique features throughout that will make you never want to leave. From the minute you park, the car to the first step inside, this home will have you wanting to come back for more. As you walk inside, the foyer immediately informs you of the quality of the home. The family room opens into the kitchen and is the perfect place to entertain family or friends. The kitchen has incredible views of Lake Knowles, and kitchen cabinets have been freshly painted. The fireplace in the family room is surrounded by built-in cabinets which provide ample storage. The French doors that lead out to the pool area provide a tremendous amount of natural light. The downstairs is finished off by an office, an additional sitting room, a dining room and a half bath. Located upstairs, 2 bedrooms share a bathroom and have doors that lead out to the covered patio. The owner’s retreat features a fireplace, crown molding, a large walk-in closet and a large master bathroom. Now that we saved one of the best parts for last let’s make our way outside! The back porch overlooks the serene pool and the screen enclosure is perfect for keeping those pesky bugs away. The rear hedge provides wonderful privacy from rear neighbors. Don’t miss the opportunity to have incredible sunsets from your very own private balcony - call today to set up your private showing.

1522 Lake Knowles Circle, Winter Park

$2,300,000

Stunning New Construction Pool Home – Available Now! Completed in 2024, this exquisite 5-bedroom, 4-bathroom home with an office and bonus room offers a perfect blend of luxury, comfort, and functionality. Available for immediate move-in, this exceptional residence features high-end finishes and is designed for modern living. As you step inside, you're greeted by soaring ceilings and rich hardwood floors that flow seamlessly throughout the home—no carpeting here! The spacious master suite is conveniently located on the first floor, offering a serene retreat complete with a spa-like bath and a custom walk-in closet. A second bedroom on the first floor is ideal for guests, providing them with a private and comfortable space. Upstairs, you'll find three generously sized bedrooms, two full baths, and a large bonus room—perfect for a media room, play area, or home gym. Plus, there's a huge walk-in storage room lined with shelves, offering an abundance of organizational space. For those who love to entertain, the formal dining room features an impressive walk-in wine room, adding a touch of sophistication. The gourmet kitchen is a chef's dream, boasting top-of-the-line appliances, a spacious island with ample seating, and plenty of cabinetry for storage. An adjacent fully equipped summer kitchen with gas appliances and phantom screens ensures seamless indoor-outdoor living. Additional highlights include custom plantation shutters throughout, a heated spa/pool combo for year-round enjoyment, and an oversized two-car garage with plenty of storage options. This home has it all—luxury, convenience, and modern design, all in a prime location. Don't miss the opportunity to make this dream home yours today! Contact us for a private tour and more information!

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

Stunning New Construction Pool Home – Available Now! Completed in 2024, this exquisite 5-bedroom, 4-bathroom home with an office and bonus room offers a perfect blend of luxury, comfort, and functionality. Available for immediate move-in, this exceptional residence features high-end finishes and is designed for modern living. As you step inside, you're greeted by soaring ceilings and rich hardwood floors that flow seamlessly throughout the home—no carpeting here! The spacious master suite is conveniently located on the first floor, offering a serene retreat complete with a spa-like bath and a custom walk-in closet. A second bedroom on the first floor is ideal for guests, providing them with a private and comfortable space. Upstairs, you'll find three generously sized bedrooms, two full baths, and a large bonus room—perfect for a media room, play area, or home gym. Plus, there's a huge walk-in storage room lined with shelves, offering an abundance of organizational space. For those who love to entertain, the formal dining room features an impressive walk-in wine room, adding a touch of sophistication. The gourmet kitchen is a chef's dream, boasting top-of-the-line appliances, a spacious island with ample seating, and plenty of cabinetry for storage. An adjacent fully equipped summer kitchen with gas appliances and phantom screens ensures seamless indoor-outdoor living. Additional highlights include custom plantation shutters throughout, a heated spa/pool combo for year-round enjoyment, and an oversized two-car garage with plenty of storage options. This home has it all—luxury, convenience, and modern design, all in a prime location. Don't miss the opportunity to make this dream home yours today! Contact us for a private tour and more information!

2172 Temple Drive, Winter Park

$5,400,000

*Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is priced to sell quickly. Walk in with instant equity in this once in a lifetime lake home. Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers the perfect blend of luxury and tranquility. With 4 bedrooms, 3.5 baths, and a generous 4,725 sq ft of living space, this home is an Aurora and Parade of Homes Grand Winner and boasts 130 ft of lakefront frontage on the serene Lake Virginia. As you approach this stunning property, you'll find it situated on a quiet cul-de-sac, ensuring peace and privacy. Step into the backyard oasis, where a lanai with a gas fireplace invites you to unwind and enjoy Florida's beautiful weather. Relax in the hot tub or take a dip in the pool equipped with an Ultraviolet System which ensures the healthiest pool water possible, complete with an outdoor shower. The outdoor home lighting creates an enchanting ambiance, while the boat dock with a covered electronic boat lift offers easy access to water adventures. Experience breathtaking sunrises and sunsets over Rollins and Knowles Chapel from your own piece of paradise. The first floor of this home is designed for both comfort and style. Anderson doors and windows fill the space with natural light, highlighting the wood floors and architectural details like coffered ceilings with wood beams in the open family room. The master suite serves as a private retreat, featuring a spa bathroom, custom closets, and ample storage. Two additional bedrooms, a bathroom, and a half bath provide versatility and convenience. The kitchen is a chef's delight, boasting Caesarstone concrete countertops, a copper hood range, top-of-the-line Subzero and Viking appliances, walk-in pantry. A walk-in bar and wine room enhance the home's functionality, while a Pelican whole house water filtration system and a Kangen Leveluk water purifier ensure the highest quality water. The second floor is perfect for entertaining, offering a spacious area with a bonus room, bar, kitchenette, and an additional bedroom with an en-suite bath. This versatile space is ideal for hosting guests or creating a personal retreat. The city of Winter Park has approved plans to add an enclosed 385 square feet to the second floor, providing potential for additional space. Don't miss the opportunity to own this extraordinary lakefront home in one of Winter Park's most sought-after neighborhoods. Experience luxury living at its finest with unparalleled lakefront views, exceptional amenities and convenience to all the restaurants and shopping that Winter Park has to offer.

4 Beds ⋅ 4 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

*Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is priced to sell quickly. Walk in with instant equity in this once in a lifetime lake home. Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers the perfect blend of luxury and tranquility. With 4 bedrooms, 3.5 baths, and a generous 4,725 sq ft of living space, this home is an Aurora and Parade of Homes Grand Winner and boasts 130 ft of lakefront frontage on the serene Lake Virginia. As you approach this stunning property, you'll find it situated on a quiet cul-de-sac, ensuring peace and privacy. Step into the backyard oasis, where a lanai with a gas fireplace invites you to unwind and enjoy Florida's beautiful weather. Relax in the hot tub or take a dip in the pool equipped with an Ultraviolet System which ensures the healthiest pool water possible, complete with an outdoor shower. The outdoor home lighting creates an enchanting ambiance, while the boat dock with a covered electronic boat lift offers easy access to water adventures. Experience breathtaking sunrises and sunsets over Rollins and Knowles Chapel from your own piece of paradise. The first floor of this home is designed for both comfort and style. Anderson doors and windows fill the space with natural light, highlighting the wood floors and architectural details like coffered ceilings with wood beams in the open family room. The master suite serves as a private retreat, featuring a spa bathroom, custom closets, and ample storage. Two additional bedrooms, a bathroom, and a half bath provide versatility and convenience. The kitchen is a chef's delight, boasting Caesarstone concrete countertops, a copper hood range, top-of-the-line Subzero and Viking appliances, walk-in pantry. A walk-in bar and wine room enhance the home's functionality, while a Pelican whole house water filtration system and a Kangen Leveluk water purifier ensure the highest quality water. The second floor is perfect for entertaining, offering a spacious area with a bonus room, bar, kitchenette, and an additional bedroom with an en-suite bath. This versatile space is ideal for hosting guests or creating a personal retreat. The city of Winter Park has approved plans to add an enclosed 385 square feet to the second floor, providing potential for additional space. Don't miss the opportunity to own this extraordinary lakefront home in one of Winter Park's most sought-after neighborhoods. Experience luxury living at its finest with unparalleled lakefront views, exceptional amenities and convenience to all the restaurants and shopping that Winter Park has to offer.

541 Virginia Drive, Winter Park

$615,000

Welcome to this elegant three-story townhouse in the heart of Winter Park! Step through French doors into a welcoming foyer leading to a bright and open living room, seamlessly connected to the dining area. Adorned with crown molding and charming Spanish tile, this space is bathed in natural light from sliding glass doors that open to a private outdoor patio. The kitchen features white cabinets, stainless steel appliances, a pantry, and a cozy eat-in nook. A convenient half bath completes the main floor. The second floor opens with a wonderful family room featuring a fireplace and French doors that lead to a picturesque balcony overlooking the street. Two generously sized bedrooms, one with custom built-ins, share a spacious bathroom, and there’s also an indoor laundry closet for added convenience. The third-floor primary retreat is a sanctuary, with a large bathroom boasting travertine details, a jetted tub, a separate shower, dual sinks, and a large walk-in closet. The oversized bedroom is bright and airy, with French doors that open to a private balcony. A dedicated office with built-in furniture completes the third floor. This home is as functional as it is beautiful, featuring a metal lifetime roof - installed 12 years ago, whole-house replumbing in 2022, and premium new carpeting with the thickest padding installed throughout the home in 2022. Additional updates include a new water heater and irrigation system added in 2023. A two-car carport and an unbeatable location short distance to Rollins College and the iconic dining and shopping of Park Avenue complete the package. Experience the best of Winter Park living! Motivated Seller all reasonable offers will be considered.

3 Beds ⋅ 3 Baths ⋅ Trotter Rep SubDv. ⋅ 32789 Zip Code

Welcome to this elegant three-story townhouse in the heart of Winter Park! Step through French doors into a welcoming foyer leading to a bright and open living room, seamlessly connected to the dining area. Adorned with crown molding and charming Spanish tile, this space is bathed in natural light from sliding glass doors that open to a private outdoor patio. The kitchen features white cabinets, stainless steel appliances, a pantry, and a cozy eat-in nook. A convenient half bath completes the main floor. The second floor opens with a wonderful family room featuring a fireplace and French doors that lead to a picturesque balcony overlooking the street. Two generously sized bedrooms, one with custom built-ins, share a spacious bathroom, and there’s also an indoor laundry closet for added convenience. The third-floor primary retreat is a sanctuary, with a large bathroom boasting travertine details, a jetted tub, a separate shower, dual sinks, and a large walk-in closet. The oversized bedroom is bright and airy, with French doors that open to a private balcony. A dedicated office with built-in furniture completes the third floor. This home is as functional as it is beautiful, featuring a metal lifetime roof - installed 12 years ago, whole-house replumbing in 2022, and premium new carpeting with the thickest padding installed throughout the home in 2022. Additional updates include a new water heater and irrigation system added in 2023. A two-car carport and an unbeatable location short distance to Rollins College and the iconic dining and shopping of Park Avenue complete the package. Experience the best of Winter Park living! Motivated Seller all reasonable offers will be considered.

735 Maryland Avenue, Winter Park

$329,900

Location, Location, Location! Lakefront complex - STUDIO APARTMENT downtown Winter Park with a BOAT SLIP! Stroll a block or two to Park Avenue and take in the magnificent galleries, museums, restaurants/cafes, boutiques, etc. You can also walk to the Sunrail (commuter train) and Amtrak Station; Farmer's Market, Rollins College and the Alfond Inn from this mostly 55+ community. Whispering Waters condo complex is directly on the shores of Lake Osceola and is a neighbor to the Winter Park Scenic Boat Ride venue. This cute corner studio apartment has an abundance of plantation shutters and is extremely light and bright. There is NOT A TRUE BEDROOM IN THIS STUDIO, but an open area with two twin beds. The Unit #15 in Bldg 7 is on the third floor where you can use the nearby elevator behind the outside stairwell that is closest to the pool. There are not many condos with boat slips on the Chain-of-Lakes but this unit comes with a highly sought after COVERED BOAT SLIP (#14)! What fun you can have exploring the beautiful, serene waters on the Chain-of-Lakes. Take in the lovely view of Lake Osceola and the community pool from your living area / enclosed balcony area. Receive mail and packages delivered directly to your front door. Park your car in the gated garage below as deeded parking space #31 comes with this condo. Also in the garage is a storage cabinet that goes with this unit. From the third floor in Bldg 7, you can go directly to the secure parking garage with a special key/slot within the elevator. The manager's office is in the garage not far from the laundry machines. Condo fee includes: electricity; water and gas; plus exterior maintenance, pool, manager, reserves, exterior insurance; grounds maintenance; trash removal. There is a club room/marina room near the lake (by the 19 covered boat slips) that could be considered a recreational bldg. Come enjoy the lifestyle Winter Park has to offer!

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Location, Location, Location! Lakefront complex - STUDIO APARTMENT downtown Winter Park with a BOAT SLIP! Stroll a block or two to Park Avenue and take in the magnificent galleries, museums, restaurants/cafes, boutiques, etc. You can also walk to the Sunrail (commuter train) and Amtrak Station; Farmer's Market, Rollins College and the Alfond Inn from this mostly 55+ community. Whispering Waters condo complex is directly on the shores of Lake Osceola and is a neighbor to the Winter Park Scenic Boat Ride venue. This cute corner studio apartment has an abundance of plantation shutters and is extremely light and bright. There is NOT A TRUE BEDROOM IN THIS STUDIO, but an open area with two twin beds. The Unit #15 in Bldg 7 is on the third floor where you can use the nearby elevator behind the outside stairwell that is closest to the pool. There are not many condos with boat slips on the Chain-of-Lakes but this unit comes with a highly sought after COVERED BOAT SLIP (#14)! What fun you can have exploring the beautiful, serene waters on the Chain-of-Lakes. Take in the lovely view of Lake Osceola and the community pool from your living area / enclosed balcony area. Receive mail and packages delivered directly to your front door. Park your car in the gated garage below as deeded parking space #31 comes with this condo. Also in the garage is a storage cabinet that goes with this unit. From the third floor in Bldg 7, you can go directly to the secure parking garage with a special key/slot within the elevator. The manager's office is in the garage not far from the laundry machines. Condo fee includes: electricity; water and gas; plus exterior maintenance, pool, manager, reserves, exterior insurance; grounds maintenance; trash removal. There is a club room/marina room near the lake (by the 19 covered boat slips) that could be considered a recreational bldg. Come enjoy the lifestyle Winter Park has to offer!

311 E Morse Boulevard Unit 7-15, Winter Park

$1,650,000

Rare opportunity to own this exclusive 2 bedrooms / 2 bathrooms condominium within the highly sought after Villa Siena. Nestled in the heart of quaint downtown Winter Park, Fl this meticulously maintained, 2nd floor, condo has been elegantly updated. Interior features include a split plan floorplan, travertine flooring, bright kitchen with quartz countertops, Sub-Zero refrigerator and Wolf gas stove, breakfast bar, dining area with custom built-in bar and wine refrigerator, crown molding within the living room, primary suite and guest bedroom offer tray ceilings, recessed lighting, walk-in closets, and french doors that lead out onto private balconies overlooking the tree lined brick street and award winning Alfond Inn and Spa, new primary bathroom with dual sinks, separate tub and shower and Toto toilet, spacious utility room with cabinetry and wash sink. Villa Siena offers secured underground parking, Club room with bar and outdoor sitting area great for entertaining guests, fitness center, roof top terrace, conference room, guest parking, and an onsite property manager to assist with Resident needs. Steps to the charming Park Avenue shopping District known for it’s celebrated restaurants, boutique stores, Central Park, 9 hole golf course, museums, train station, and Rollins College. Welcome Home! Video Tour: https://youtu.be/AMDbRupc4GM

2 Beds ⋅ 2 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code

Rare opportunity to own this exclusive 2 bedrooms / 2 bathrooms condominium within the highly sought after Villa Siena. Nestled in the heart of quaint downtown Winter Park, Fl this meticulously maintained, 2nd floor, condo has been elegantly updated. Interior features include a split plan floorplan, travertine flooring, bright kitchen with quartz countertops, Sub-Zero refrigerator and Wolf gas stove, breakfast bar, dining area with custom built-in bar and wine refrigerator, crown molding within the living room, primary suite and guest bedroom offer tray ceilings, recessed lighting, walk-in closets, and french doors that lead out onto private balconies overlooking the tree lined brick street and award winning Alfond Inn and Spa, new primary bathroom with dual sinks, separate tub and shower and Toto toilet, spacious utility room with cabinetry and wash sink. Villa Siena offers secured underground parking, Club room with bar and outdoor sitting area great for entertaining guests, fitness center, roof top terrace, conference room, guest parking, and an onsite property manager to assist with Resident needs. Steps to the charming Park Avenue shopping District known for it’s celebrated restaurants, boutique stores, Central Park, 9 hole golf course, museums, train station, and Rollins College. Welcome Home! Video Tour: https://youtu.be/AMDbRupc4GM

315 E New England Avenue Unit 9, Winter Park

$1,895,000

Welcome to an extraordinary custom-built pool home that beautifully harmonizes contemporary elegance with traditional charm. This stunning residence is a true masterpiece, showcasing top-tier details and finishes that elevate it to a league of its own. Upon entering, you are greeted by exquisite new white oak wood flooring that flows gracefully throughout the home. The grand foyer opens into a living room, highlighting a breathtaking two-story ceiling that reaches 20 feet. The dining area is equally impressive, featuring elegant built-ins and under-counter wine and beverage refrigerators, perfect for hosting dinner parties and celebrations. At the heart of this home lies a stunning new chef-inspired kitchen designed for culinary enthusiasts and family gatherings alike. Equipped with a state-of-the-art Monogram appliance package, this kitchen boasts a commercial-grade gas range with six burners and dual dishwashers for optimal efficiency. A built-in microwave conveniently situated in the island, along with custom cabinetry and luxurious thick porcelain countertops, elevates the space further. The expansive center island invites creativity and connection, making it the ideal backdrop for memorable meals. Adjacent to the kitchen, the open family room features a cozy corner gas fireplace and three sets of French doors that seamlessly connect the indoor space to the covered and screened lanai, where you can unwind and enjoy serene views of the sparkling saltwater pool. Step outside to discover your private oasis, perfect for entertaining. The outdoor living area includes a fully equipped summer kitchen featuring a Wolf grill, concrete counters, a sink, and an under-counter fridge. A charming outdoor pool bath with a shower adds convenience. Back inside, connecting the kitchen to the spacious two-car garage with 14-foot ceilings, you'll find a well-appointed mudroom complete with laundry facilities, newly added storage cabinetry, a walk-in pantry, and a double wash basin, ensuring both functionality and organization. Ascend the wide, oversized staircase to the second level, where you'll discover two generously sized secondary bedrooms complemented by a newly updated hall bath. The sprawling primary suite is a true retreat, featuring two large walk-in closets and a luxurious spa bath equipped with a cast iron clawfoot tub, a bidet, and a seamless glass shower. This suite also includes a serene and secluded nook, perfect for creating a peaceful office space or nursery. The suite also boasts easy access to a screened balcony. Additionally, the home features a private first-floor guest suite with an ensuite bath, perfect for hosting friends or family. Every inch of this residence reflects exceptional craftsmanship, from the tasteful custom cabinetry to the elegant wood trim. The atmosphere exudes grandeur and comfort, enhanced by 11-foot ceilings and oversized baseboards. Nestled in a tranquil corner of the backyard, the air-conditioned shed serves as the perfect sanctuary for a gym or yoga studio, offering a peaceful bonus space that everyone will adore. The backyard showcases low-maintenance turf along with energy-efficient, drought-tolerant landscaping that beautifully enhances the home's overall appeal. Enjoy a stunning outdoor space that requires minimal upkeep while remaining environmentally friendly! Conveniently located just minutes away from the vibrant shops and restaurants and within the highly sought-after Winter Park school district.

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

Welcome to an extraordinary custom-built pool home that beautifully harmonizes contemporary elegance with traditional charm. This stunning residence is a true masterpiece, showcasing top-tier details and finishes that elevate it to a league of its own. Upon entering, you are greeted by exquisite new white oak wood flooring that flows gracefully throughout the home. The grand foyer opens into a living room, highlighting a breathtaking two-story ceiling that reaches 20 feet. The dining area is equally impressive, featuring elegant built-ins and under-counter wine and beverage refrigerators, perfect for hosting dinner parties and celebrations. At the heart of this home lies a stunning new chef-inspired kitchen designed for culinary enthusiasts and family gatherings alike. Equipped with a state-of-the-art Monogram appliance package, this kitchen boasts a commercial-grade gas range with six burners and dual dishwashers for optimal efficiency. A built-in microwave conveniently situated in the island, along with custom cabinetry and luxurious thick porcelain countertops, elevates the space further. The expansive center island invites creativity and connection, making it the ideal backdrop for memorable meals. Adjacent to the kitchen, the open family room features a cozy corner gas fireplace and three sets of French doors that seamlessly connect the indoor space to the covered and screened lanai, where you can unwind and enjoy serene views of the sparkling saltwater pool. Step outside to discover your private oasis, perfect for entertaining. The outdoor living area includes a fully equipped summer kitchen featuring a Wolf grill, concrete counters, a sink, and an under-counter fridge. A charming outdoor pool bath with a shower adds convenience. Back inside, connecting the kitchen to the spacious two-car garage with 14-foot ceilings, you'll find a well-appointed mudroom complete with laundry facilities, newly added storage cabinetry, a walk-in pantry, and a double wash basin, ensuring both functionality and organization. Ascend the wide, oversized staircase to the second level, where you'll discover two generously sized secondary bedrooms complemented by a newly updated hall bath. The sprawling primary suite is a true retreat, featuring two large walk-in closets and a luxurious spa bath equipped with a cast iron clawfoot tub, a bidet, and a seamless glass shower. This suite also includes a serene and secluded nook, perfect for creating a peaceful office space or nursery. The suite also boasts easy access to a screened balcony. Additionally, the home features a private first-floor guest suite with an ensuite bath, perfect for hosting friends or family. Every inch of this residence reflects exceptional craftsmanship, from the tasteful custom cabinetry to the elegant wood trim. The atmosphere exudes grandeur and comfort, enhanced by 11-foot ceilings and oversized baseboards. Nestled in a tranquil corner of the backyard, the air-conditioned shed serves as the perfect sanctuary for a gym or yoga studio, offering a peaceful bonus space that everyone will adore. The backyard showcases low-maintenance turf along with energy-efficient, drought-tolerant landscaping that beautifully enhances the home's overall appeal. Enjoy a stunning outdoor space that requires minimal upkeep while remaining environmentally friendly! Conveniently located just minutes away from the vibrant shops and restaurants and within the highly sought-after Winter Park school district.

2612 Parkland Drive, Winter Park

$4,430,000

New Home Nestled in the esteemed The Vias area and near the WPRC. Situated on a secluded street, it occupies an approximately 0.58-acre lot with an expansive backyard landscape that is truly captivating. This exquisite home encompasses five bedrooms and six-and-a-half bathrooms with a four-car garage. An indomitable presence is seen in its immense and grand pivoting iron door which directs you to a double-height foyer and great room separated by a glass-railing catwalk. The property boasts exclusive features like a formal dining room endowed with a glass-encased wine display as well as an intimate den/office safeguarded by private entrance doors. The airy master bedroom is adorned with sliding doors that open up to reveal a private lanai overlooking the pool area; one cannot overlook its distinctively vast his-and-hers walk-in closets complemented by a spa-like luxurious bathroom suite. A state-of-the-art kitchen featuring gold Calacatta Quartz countertops/backsplash matched alongside an oversized walk-in pantry, creating everyday usability flanked with indulgence! Two separate upper and lower level laundry rooms serve this expansive open floor plan a win-win situation for convenience! Adding exceptional charm to this stunning home is a family room equipped with zero corner sliding doors opening up towards the summer kitchen leading onto a large covered patio encased in travertine pavers-- making it your personal haven for enhancing entertainment moods. Venturing upstairs via an elegant Quartz staircase leads you to an additional four en-suite bedrooms (each with walk-in closets). Complementing your leisure needs flawlessly are a comfy lounge space and fun-filled game room with a wet bar setup; creating a direct pathway onto a sprawling balcony exhibiting glass railings overlooking backyards - commanding mesmerizing views of your saltwater gas-heated pool and cozy gas firepit with a seating area for social gatherings! A dedicated full-bath pool with a steam shower. Home gets fully enveloped using high-quality materials fashioned from Large Porcelain format tiles, European tiles, Travertine pavers, and Swiss-origin WPL catering to its strength quotient. Tor uniquely detailed outlook, the property also offers a detached additional building that has been thoughtfully renovated to deliver an extra 600 sq ft of living space - not part of the main house size calculation (6475 sq ft). With 1 bedroom, 1 full bath, a fully functional kitchen surrounded by a living area, and a covered/tiled porch; it makes for a rare addition delivering discernible usefulness. Think creativity! Convert it into a guest house, in-law suite, gym space, professional office setup, or even a hobby room - multiple endless usage options make its possession a valued choice! The home is available now and move-in ready! Get one step closer to owning the realization of your dream dwelling experience!

5 Beds ⋅ 7 Baths ⋅ Tuscania SubDv. ⋅ 32789 Zip Code

New Home Nestled in the esteemed The Vias area and near the WPRC. Situated on a secluded street, it occupies an approximately 0.58-acre lot with an expansive backyard landscape that is truly captivating. This exquisite home encompasses five bedrooms and six-and-a-half bathrooms with a four-car garage. An indomitable presence is seen in its immense and grand pivoting iron door which directs you to a double-height foyer and great room separated by a glass-railing catwalk. The property boasts exclusive features like a formal dining room endowed with a glass-encased wine display as well as an intimate den/office safeguarded by private entrance doors. The airy master bedroom is adorned with sliding doors that open up to reveal a private lanai overlooking the pool area; one cannot overlook its distinctively vast his-and-hers walk-in closets complemented by a spa-like luxurious bathroom suite. A state-of-the-art kitchen featuring gold Calacatta Quartz countertops/backsplash matched alongside an oversized walk-in pantry, creating everyday usability flanked with indulgence! Two separate upper and lower level laundry rooms serve this expansive open floor plan a win-win situation for convenience! Adding exceptional charm to this stunning home is a family room equipped with zero corner sliding doors opening up towards the summer kitchen leading onto a large covered patio encased in travertine pavers-- making it your personal haven for enhancing entertainment moods. Venturing upstairs via an elegant Quartz staircase leads you to an additional four en-suite bedrooms (each with walk-in closets). Complementing your leisure needs flawlessly are a comfy lounge space and fun-filled game room with a wet bar setup; creating a direct pathway onto a sprawling balcony exhibiting glass railings overlooking backyards - commanding mesmerizing views of your saltwater gas-heated pool and cozy gas firepit with a seating area for social gatherings! A dedicated full-bath pool with a steam shower. Home gets fully enveloped using high-quality materials fashioned from Large Porcelain format tiles, European tiles, Travertine pavers, and Swiss-origin WPL catering to its strength quotient. Tor uniquely detailed outlook, the property also offers a detached additional building that has been thoughtfully renovated to deliver an extra 600 sq ft of living space - not part of the main house size calculation (6475 sq ft). With 1 bedroom, 1 full bath, a fully functional kitchen surrounded by a living area, and a covered/tiled porch; it makes for a rare addition delivering discernible usefulness. Think creativity! Convert it into a guest house, in-law suite, gym space, professional office setup, or even a hobby room - multiple endless usage options make its possession a valued choice! The home is available now and move-in ready! Get one step closer to owning the realization of your dream dwelling experience!

2161 Sharon Road, Winter Park

$950,000

**Stunning Winter Park Home Near Rollins College, Park Ave & Lake Virginia** Located in historic Winter Park, this exceptional 3-bedroom, 2.5-bathroom home offers the perfect blend of modern luxury and classic charm. Just minutes from Rollins College, the upscale dining and shopping of Park Avenue, and the serene beauty of Lake Virginia, this home is ideally situated in a vibrant yet peaceful neighborhood. **Private Backyard Oasis** Step outside to your own private retreat. The fully fenced-in yard features a free-form pool, a large deck, and a pergola, offering a perfect space for outdoor relaxation and entertaining. Whether you’re enjoying a quiet afternoon by the pool or hosting guests, this backyard provides an ideal setting for any occasion. **Interior Features for Comfortable Living** Inside, the home boasts a spacious and functional layout. The chef’s kitchen is equipped with high-end appliances, custom cabinetry, and ample counter space, perfect for preparing meals and entertaining. The open-concept living and dining areas create a seamless flow throughout the home. The oversized primary bedroom is a serene escape, featuring a luxurious en-suite bathroom with a soaking tub, separate walk-in shower, and elegant finishes. The massive walk-in closet offers plenty of storage space for all your needs. **Modern Updates for Peace of Mind** This home is move-in ready, with a brand-new A/C system, new A/C ducts, and a newer roof, ensuring long-term comfort and reliability. **Ample Parking & Storage** With a 2-car garage and multiple driveways accommodating up to 12 cars, parking is never a concern. Additionally, a side gate allows access to a secured side yard that can store up to 2 more cars, adding extra convenience and protection. **Top-Rated Schools & Prime Location** Located in a highly-rated school district, this home offers access to excellent educational opportunities. It’s also ideally positioned for easy access to major highways, making downtown Orlando and surrounding areas easily reachable while maintaining the tranquility of Winter Park. **Development Potential** Sitting on a large 12,000-square-foot lot, this property presents a prime opportunity for future development. Whether you’re looking to build your dream home or invest in a high-demand Winter Park location, this lot offers significant potential. --- With its prime location, stylish updates, and ample outdoor space, this home is a rare find. Don’t miss your chance to own a piece of Winter Park—schedule a private tour today!

3 Beds ⋅ 3 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

**Stunning Winter Park Home Near Rollins College, Park Ave & Lake Virginia** Located in historic Winter Park, this exceptional 3-bedroom, 2.5-bathroom home offers the perfect blend of modern luxury and classic charm. Just minutes from Rollins College, the upscale dining and shopping of Park Avenue, and the serene beauty of Lake Virginia, this home is ideally situated in a vibrant yet peaceful neighborhood. **Private Backyard Oasis** Step outside to your own private retreat. The fully fenced-in yard features a free-form pool, a large deck, and a pergola, offering a perfect space for outdoor relaxation and entertaining. Whether you’re enjoying a quiet afternoon by the pool or hosting guests, this backyard provides an ideal setting for any occasion. **Interior Features for Comfortable Living** Inside, the home boasts a spacious and functional layout. The chef’s kitchen is equipped with high-end appliances, custom cabinetry, and ample counter space, perfect for preparing meals and entertaining. The open-concept living and dining areas create a seamless flow throughout the home. The oversized primary bedroom is a serene escape, featuring a luxurious en-suite bathroom with a soaking tub, separate walk-in shower, and elegant finishes. The massive walk-in closet offers plenty of storage space for all your needs. **Modern Updates for Peace of Mind** This home is move-in ready, with a brand-new A/C system, new A/C ducts, and a newer roof, ensuring long-term comfort and reliability. **Ample Parking & Storage** With a 2-car garage and multiple driveways accommodating up to 12 cars, parking is never a concern. Additionally, a side gate allows access to a secured side yard that can store up to 2 more cars, adding extra convenience and protection. **Top-Rated Schools & Prime Location** Located in a highly-rated school district, this home offers access to excellent educational opportunities. It’s also ideally positioned for easy access to major highways, making downtown Orlando and surrounding areas easily reachable while maintaining the tranquility of Winter Park. **Development Potential** Sitting on a large 12,000-square-foot lot, this property presents a prime opportunity for future development. Whether you’re looking to build your dream home or invest in a high-demand Winter Park location, this lot offers significant potential. --- With its prime location, stylish updates, and ample outdoor space, this home is a rare find. Don’t miss your chance to own a piece of Winter Park—schedule a private tour today!

241 W Lake Sue Avenue, Winter Park

$195,000

One or more photo(s) has been virtually staged. Welcome to your next chapter of lakeside living! This charming one-bedroom, one-bathroom condo offers a perfect blend of tranquility and convenience in the heart of Winter Park. Step inside to discover a thoughtfully designed space where comfort meets style. The open-concept living area welcomes you with beautiful engineered wood floors, creating a seamless flow between the living room and kitchen. Natural light streams through the windows, highlighting the warm and inviting atmosphere throughout.Your private bedroom retreat features a generously sized closet, making storage a breeze. The well-appointed bathroom complements the living space perfectly. What truly sets this home apart is its privileged location near Lake Killarney, a stunning 239-acre spring-fed lake that serves as your backyard oasis. As a resident, you'll enjoy exclusive access to on-site boat slips, a launch, and an updated dock. Take a peaceful stroll along the 60-foot walkway leading to a covered gazebo - the perfect spot for your morning coffee or evening sunset views. The community amenities include a lakefront pool and clubhouse, while the meticulously maintained grounds showcase lush Florida landscaping. Located just moments from Winter Park Village, you'll find fantastic shopping, dining, and entertainment options right around the corner. Experience the joy of maintenance-free living while being connected to nature and urban conveniences. This hidden gem won't last long!

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Welcome to your next chapter of lakeside living! This charming one-bedroom, one-bathroom condo offers a perfect blend of tranquility and convenience in the heart of Winter Park. Step inside to discover a thoughtfully designed space where comfort meets style. The open-concept living area welcomes you with beautiful engineered wood floors, creating a seamless flow between the living room and kitchen. Natural light streams through the windows, highlighting the warm and inviting atmosphere throughout.Your private bedroom retreat features a generously sized closet, making storage a breeze. The well-appointed bathroom complements the living space perfectly. What truly sets this home apart is its privileged location near Lake Killarney, a stunning 239-acre spring-fed lake that serves as your backyard oasis. As a resident, you'll enjoy exclusive access to on-site boat slips, a launch, and an updated dock. Take a peaceful stroll along the 60-foot walkway leading to a covered gazebo - the perfect spot for your morning coffee or evening sunset views. The community amenities include a lakefront pool and clubhouse, while the meticulously maintained grounds showcase lush Florida landscaping. Located just moments from Winter Park Village, you'll find fantastic shopping, dining, and entertainment options right around the corner. Experience the joy of maintenance-free living while being connected to nature and urban conveniences. This hidden gem won't last long!

2500 Lee Road Unit 243, Winter Park

$1,125,000

Welcome to this exquisite Mediterranean-inspired home located in the heart of Winter Park, Florida. This residence offers luxurious living spaces and modern amenities both inside and out, complemented with a detached mother-in-law suite, all nestled on a beautifully landscaped private community with a sprawling park right in your backyard. Upon entering, you'll immediately be impressed by the spacious and open floor plan, featuring elegant finishes, new flooring throughout, and an abundance of natural light. The chef’s kitchen is designed for both functionality and style, with high-end appliances, ample counter space, and a large island that opens up to the living and dining areas. The perfect layout for entertaining and everyday living. Each of the four bedrooms is generously sized, with the primary suite offering a private retreat complete with an ensuite bathroom and an oversized walk-in closet. With four full bathrooms and an additional half bath, there is plenty of space for everyone. A standout feature of this home is the detached mother-in-law suite located above the garage. This private and fully equipped living space provides ultimate flexibility, whether used for guests, a home office, or multi-generational living. Located just minutes from Winter Park Village and the vibrant Park Avenue, you'll enjoy the convenience of boutique shopping, fine dining, and cultural attractions just a short drive away. This home is move-in ready. Built with meticulous attention to detail, offering comfort, privacy, and a prime Winter Park location.

4 Beds ⋅ 5 Baths ⋅ Hamilton Place SubDv. ⋅ 32789 Zip Code

Welcome to this exquisite Mediterranean-inspired home located in the heart of Winter Park, Florida. This residence offers luxurious living spaces and modern amenities both inside and out, complemented with a detached mother-in-law suite, all nestled on a beautifully landscaped private community with a sprawling park right in your backyard. Upon entering, you'll immediately be impressed by the spacious and open floor plan, featuring elegant finishes, new flooring throughout, and an abundance of natural light. The chef’s kitchen is designed for both functionality and style, with high-end appliances, ample counter space, and a large island that opens up to the living and dining areas. The perfect layout for entertaining and everyday living. Each of the four bedrooms is generously sized, with the primary suite offering a private retreat complete with an ensuite bathroom and an oversized walk-in closet. With four full bathrooms and an additional half bath, there is plenty of space for everyone. A standout feature of this home is the detached mother-in-law suite located above the garage. This private and fully equipped living space provides ultimate flexibility, whether used for guests, a home office, or multi-generational living. Located just minutes from Winter Park Village and the vibrant Park Avenue, you'll enjoy the convenience of boutique shopping, fine dining, and cultural attractions just a short drive away. This home is move-in ready. Built with meticulous attention to detail, offering comfort, privacy, and a prime Winter Park location.

805 Hamilton Place Court, Winter Park