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$775,000

Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious, designer-selected finishes throughout. Step inside to discover a beautifully appointed interior featuring high-end touches. The kitchen is a true showpiece, boasting custom wood cabinetry with artistic wood detailing, granite countertops, full counter-to-cabinet backsplashes, and top-tier appliances including a Wolf cooktop and oven, Fisher & Paykel dishwasher, Liebherr wine cooler, and Sub-Zero refrigerator. The expansive kitchen island comfortably seats four, with a sleek, integrated extension that effortlessly accommodates up to seven—perfect for entertaining in style. The open-concept living area flows seamlessly to a spacious private balcony, offering tranquil views of the heated pool, putting green, lush landscaping, and the shimmering waters of Lake Osceola—ideal for a morning coffee or year-round entertaining. The primary suite is a serene retreat, featuring blackout blinds, a Sleep Number smart bed with dual temperature controls, and custom floor-to-ceiling built-ins with integrated lighting, display shelving, and a dedicated vanity area. Additional built-in cabinetry lines the hallway leading to the en-suite bathroom, providing ample space for jewelry, shoes, and wardrobe essentials. The second bedroom is designed for versatility, with a wall-to-wall built-in home office setup overlooking a beautiful resort-style view, along with its own matching floor-to-ceiling built-ins for display and storage. Both bathrooms have been tastefully reimagined with new vanities, granite countertops, upgraded shower enclosures and hardware, and stylish lighting and mirrors. The primary bath includes additional custom built-ins for optimal storage and organization. Throughout the home, fresh paint and luxury vinyl flooring create a clean, modern aesthetic. Additional features include an in-unit washer and dryer tucked behind a custom wood door, a built-in safe, and a new A/C unit installed in 2024. The residence also includes a deeded covered-parking space and a private storage unit. The Cloisters community offers a wealth of amenities, including an onsite property manager, ample guest parking, elevators, a heated pool, onsite laundry facilities, a putting green, private lake access, a dock, and boat slips available via resident lottery. Residents also enjoy two fitness centers with one dry sauna and a recently updated clubhouse with a full kitchen and bath—ideal for private gatherings. Just a short stroll from the boutiques, restaurants, and cultural attractions of Park Avenue, and Rollins College, this fully renovated, turnkey residence presents a rare opportunity to enjoy the ultimate blend of location, luxury, and lifestyle. Realtor/owner is a licensed Florida real estate broker.

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

Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious, designer-selected finishes throughout. Step inside to discover a beautifully appointed interior featuring high-end touches. The kitchen is a true showpiece, boasting custom wood cabinetry with artistic wood detailing, granite countertops, full counter-to-cabinet backsplashes, and top-tier appliances including a Wolf cooktop and oven, Fisher & Paykel dishwasher, Liebherr wine cooler, and Sub-Zero refrigerator. The expansive kitchen island comfortably seats four, with a sleek, integrated extension that effortlessly accommodates up to seven—perfect for entertaining in style. The open-concept living area flows seamlessly to a spacious private balcony, offering tranquil views of the heated pool, putting green, lush landscaping, and the shimmering waters of Lake Osceola—ideal for a morning coffee or year-round entertaining. The primary suite is a serene retreat, featuring blackout blinds, a Sleep Number smart bed with dual temperature controls, and custom floor-to-ceiling built-ins with integrated lighting, display shelving, and a dedicated vanity area. Additional built-in cabinetry lines the hallway leading to the en-suite bathroom, providing ample space for jewelry, shoes, and wardrobe essentials. The second bedroom is designed for versatility, with a wall-to-wall built-in home office setup overlooking a beautiful resort-style view, along with its own matching floor-to-ceiling built-ins for display and storage. Both bathrooms have been tastefully reimagined with new vanities, granite countertops, upgraded shower enclosures and hardware, and stylish lighting and mirrors. The primary bath includes additional custom built-ins for optimal storage and organization. Throughout the home, fresh paint and luxury vinyl flooring create a clean, modern aesthetic. Additional features include an in-unit washer and dryer tucked behind a custom wood door, a built-in safe, and a new A/C unit installed in 2024. The residence also includes a deeded covered-parking space and a private storage unit. The Cloisters community offers a wealth of amenities, including an onsite property manager, ample guest parking, elevators, a heated pool, onsite laundry facilities, a putting green, private lake access, a dock, and boat slips available via resident lottery. Residents also enjoy two fitness centers with one dry sauna and a recently updated clubhouse with a full kitchen and bath—ideal for private gatherings. Just a short stroll from the boutiques, restaurants, and cultural attractions of Park Avenue, and Rollins College, this fully renovated, turnkey residence presents a rare opportunity to enjoy the ultimate blend of location, luxury, and lifestyle. Realtor/owner is a licensed Florida real estate broker.

100 S Interlachen Avenue Unit 204D, Winter Park

$3,350,000

Welcome to 641 Virginia Drive, a rare and remarkable lakefront property located in the highly sought-after Timberlane Shores neighborhood of Winter Park. This expansive .48-acre lot offers approximately 100 feet of frontage on Lake Virginia, one of the most desirable lakes on the prestigious Winter Park Chain of Lakes. The existing 4-bedroom, 3-bath home features 3,223 square feet of living space and showcases Country French architectural charm, offering an ideal opportunity to renovate and enhance its timeless appeal—or build new and design a custom estate that takes full advantage of this exceptional lakefront setting. Whether modernizing the current layout or crafting an architectural masterpiece from the ground up, this property offers limitless potential. The home enjoys northern lakefront exposure, providing breathtaking views to the northeast of Winter Park’s protected Genius Preserve and to the west of the iconic Rollins College shoreline, creating a picturesque backdrop with year-round natural beauty and unforgettable sunsets. Significant recent improvements have already been made, including a new roof installed in 2023 with 50-year composite cedar shake shingles, offering the charm of natural materials with enhanced durability. In addition, the dock was redecked in 2023, making this waterfront ready for immediate enjoyment. A rare enclosed boathouse and private dock offer direct access to Lake Virginia and the entire Winter Park Chain of Lakes—ideal for boating, paddleboarding, and lakeside entertaining. Few properties in Winter Park feature this level of water access and historic charm on such a prime stretch of shoreline. Set among multimillion-dollar estates and located just minutes from Park Avenue’s renowned shopping and dining, Rollins College, the Winter Park Golf Course, and a variety of cultural amenities, this property provides the perfect balance of privacy and accessibility. Zoned for top-rated Audubon Park K-8 and Winter Park High School, it offers an ideal location for those seeking the best in lifestyle and education. Whether you're seeking a peaceful lakefront retreat, a renovation opportunity with character, or the perfect site to build your dream home, 641 Virginia Drive offers a once-in-a-generation opportunity in one of Central Florida’s most distinguished communities.

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

Welcome to 641 Virginia Drive, a rare and remarkable lakefront property located in the highly sought-after Timberlane Shores neighborhood of Winter Park. This expansive .48-acre lot offers approximately 100 feet of frontage on Lake Virginia, one of the most desirable lakes on the prestigious Winter Park Chain of Lakes. The existing 4-bedroom, 3-bath home features 3,223 square feet of living space and showcases Country French architectural charm, offering an ideal opportunity to renovate and enhance its timeless appeal—or build new and design a custom estate that takes full advantage of this exceptional lakefront setting. Whether modernizing the current layout or crafting an architectural masterpiece from the ground up, this property offers limitless potential. The home enjoys northern lakefront exposure, providing breathtaking views to the northeast of Winter Park’s protected Genius Preserve and to the west of the iconic Rollins College shoreline, creating a picturesque backdrop with year-round natural beauty and unforgettable sunsets. Significant recent improvements have already been made, including a new roof installed in 2023 with 50-year composite cedar shake shingles, offering the charm of natural materials with enhanced durability. In addition, the dock was redecked in 2023, making this waterfront ready for immediate enjoyment. A rare enclosed boathouse and private dock offer direct access to Lake Virginia and the entire Winter Park Chain of Lakes—ideal for boating, paddleboarding, and lakeside entertaining. Few properties in Winter Park feature this level of water access and historic charm on such a prime stretch of shoreline. Set among multimillion-dollar estates and located just minutes from Park Avenue’s renowned shopping and dining, Rollins College, the Winter Park Golf Course, and a variety of cultural amenities, this property provides the perfect balance of privacy and accessibility. Zoned for top-rated Audubon Park K-8 and Winter Park High School, it offers an ideal location for those seeking the best in lifestyle and education. Whether you're seeking a peaceful lakefront retreat, a renovation opportunity with character, or the perfect site to build your dream home, 641 Virginia Drive offers a once-in-a-generation opportunity in one of Central Florida’s most distinguished communities.

641 Virginia Drive, Winter Park

$750,000

Location, location, location! Whether you're ready to build your dream home or simply want to enjoy life in Central Florida’s most prestigious neighborhood at an unbeatable value, this delightful mid-century 2-bedroom, 2-bathroom home offers endless possibilities. Lot size is approximately 130 ft X 78 ft. Perfectly positioned just minutes from Park Avenue, Rollins College, and Lake Osceola, this home places you at the center of luxury Winter Park living—enjoy boutique shopping, fine dining, scenic strolls, or morning paddle boarding just steps from your door. Inside, you'll find a bright and open floor plan filled with natural light and timeless charm. A front den/office with white tile flooring and timeless tongue and groove ceiling offers you space that is not only stylish but functional—ideal for working from home or relaxing with a book. The open living/dining area features stylish wood flooring, large windows, and a ceiling fan for year-round comfort. This unique layout offers 2 primary suites offering plenty of privacy. Head to the fully fenced back yard and concrete patio which provides a private retreat for entertaining or relaxing outdoors. You will find yourself in the heart of it all with close proximity shops, restaurants, schools, universities and major airports. An added hidden bonus is your access to Lake Osceola through 2 parks and walkway ramp, where you can enjoy a beautiful sunset or paddle board/kayak ride. With vintage character, and incredible location with lake access at the end of the street, this Winter Park gem is not to be missed!

2 Beds ⋅ 2 Baths ⋅ Osceola Summit SubDv. ⋅ 32789 Zip Code

Location, location, location! Whether you're ready to build your dream home or simply want to enjoy life in Central Florida’s most prestigious neighborhood at an unbeatable value, this delightful mid-century 2-bedroom, 2-bathroom home offers endless possibilities. Lot size is approximately 130 ft X 78 ft. Perfectly positioned just minutes from Park Avenue, Rollins College, and Lake Osceola, this home places you at the center of luxury Winter Park living—enjoy boutique shopping, fine dining, scenic strolls, or morning paddle boarding just steps from your door. Inside, you'll find a bright and open floor plan filled with natural light and timeless charm. A front den/office with white tile flooring and timeless tongue and groove ceiling offers you space that is not only stylish but functional—ideal for working from home or relaxing with a book. The open living/dining area features stylish wood flooring, large windows, and a ceiling fan for year-round comfort. This unique layout offers 2 primary suites offering plenty of privacy. Head to the fully fenced back yard and concrete patio which provides a private retreat for entertaining or relaxing outdoors. You will find yourself in the heart of it all with close proximity shops, restaurants, schools, universities and major airports. An added hidden bonus is your access to Lake Osceola through 2 parks and walkway ramp, where you can enjoy a beautiful sunset or paddle board/kayak ride. With vintage character, and incredible location with lake access at the end of the street, this Winter Park gem is not to be missed!

311 Cortland Avenue, Winter Park

$1,785,000

This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered lanai. This home has a warm and welcoming atmosphere perfect for entertaining family & friends. The gourmet kitchen features an induction cook top, built in convection & microwave oven, stainless steel refrigerator, vented stainless steel hood system, wine refrigerator, bar station, and pantry. It also has custom designed kitchen cabinetry with abundant storage and pull out shelving plus a big island with designer pendant lights and eat in area for a large table and chairs. The laundry room next to the master bedroom has cabinetry and a sink. Adjacent to the living room is a room that could be used as a office or workout room AND a big multi functional room with half bathroom also overlooking the pool area. Sliders from the living room and the multi functional room are pocket sliders which really open up the home in cooler weather ! The huge master suite also opens to the pool and has his and hers walk in closets with built in custom closet organizers and the master bathroom has dual sinks, whirlpool garden tub, and big walk in shower. In addition, there are two guest bedrooms that share a hall bathroom. The backyard is fenced and very private and peaceful with a gravel walkway with low voltage lighting that leads to an arbor with a swing for an outdoor gathering or reflection. Other upgrades includes Plantation shutters, motorized shades on sliding doors, whole house built in audio system, and security system. Roof was installed in 2019 and new pool pump. Steps away is Phelps Park with playground, tennis and pickleball courts and the YMCA is nearby. Park Avenue and Downtown Winter Park with plenty of fine dining and upscale shopping options are a bike ride away or short drive !

3 Beds ⋅ 3 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code

This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered lanai. This home has a warm and welcoming atmosphere perfect for entertaining family & friends. The gourmet kitchen features an induction cook top, built in convection & microwave oven, stainless steel refrigerator, vented stainless steel hood system, wine refrigerator, bar station, and pantry. It also has custom designed kitchen cabinetry with abundant storage and pull out shelving plus a big island with designer pendant lights and eat in area for a large table and chairs. The laundry room next to the master bedroom has cabinetry and a sink. Adjacent to the living room is a room that could be used as a office or workout room AND a big multi functional room with half bathroom also overlooking the pool area. Sliders from the living room and the multi functional room are pocket sliders which really open up the home in cooler weather ! The huge master suite also opens to the pool and has his and hers walk in closets with built in custom closet organizers and the master bathroom has dual sinks, whirlpool garden tub, and big walk in shower. In addition, there are two guest bedrooms that share a hall bathroom. The backyard is fenced and very private and peaceful with a gravel walkway with low voltage lighting that leads to an arbor with a swing for an outdoor gathering or reflection. Other upgrades includes Plantation shutters, motorized shades on sliding doors, whole house built in audio system, and security system. Roof was installed in 2019 and new pool pump. Steps away is Phelps Park with playground, tennis and pickleball courts and the YMCA is nearby. Park Avenue and Downtown Winter Park with plenty of fine dining and upscale shopping options are a bike ride away or short drive !

1640 Mayfield Avenue, Winter Park

$1,800,000

Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-family home offering over 4,100 SF of living space. Ideally located on a tree-lined street with Winter Park’s signature brick roads, this home sits in one of the area’s most sought-after neighborhoods. Just minutes from the Winter Park Racquet Club in the Vias, Park Avenue shops and dining, YMCA, top hospitals, and excellent public and private schools, it offers the best of Winter Park living. A charming front porch leads into a thoughtfully designed interior that blends classic style with modern functionality. To the right of the foyer is a private office with built-in shelving and glass pocket door, while the left opens to a formal dining room with a tray ceiling, chandelier, and ambient lighting. The spacious living room features a gas fireplace, beamed ceiling, crown molding, and built-in shelving, with French doors that open to the screened lanai for seamless indoor-outdoor living. The chef’s kitchen offers ample cabinetry, expansive countertops, a center island with secondary sink, walk-in pantry, and a breakfast nook with more French doors to the lanai. On the main floor, the primary suite includes a spa-inspired bath with double vanities, garden tub, and multiple closets. A guest suite also on the first floor includes a private bath, beverage fridge, and coffee station. A full laundry room and butler’s pantry with wine fridge complete the first level. Upstairs features a large loft with built-in cabinetry, under-cabinet lighting, and a beverage fridge. A built-in desk and cabinets line the hallway for study or work space. Two bedrooms share a Jack and Jill bath, and a third has access to a nearby full bath. A second laundry room, currently used as an office, adds flexibility. Step outside to a private backyard oasis with a screened lanai, sparkling pool, outdoor kitchen, mature landscaping, and full pool bathroom. With a new roof (2023), commercial grade water heater (2022), fresh exterior paint (2024) and many upgrades, this home offers turnkey living in one of Winter Park’s finest communities.

5 Beds ⋅ 6 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-family home offering over 4,100 SF of living space. Ideally located on a tree-lined street with Winter Park’s signature brick roads, this home sits in one of the area’s most sought-after neighborhoods. Just minutes from the Winter Park Racquet Club in the Vias, Park Avenue shops and dining, YMCA, top hospitals, and excellent public and private schools, it offers the best of Winter Park living. A charming front porch leads into a thoughtfully designed interior that blends classic style with modern functionality. To the right of the foyer is a private office with built-in shelving and glass pocket door, while the left opens to a formal dining room with a tray ceiling, chandelier, and ambient lighting. The spacious living room features a gas fireplace, beamed ceiling, crown molding, and built-in shelving, with French doors that open to the screened lanai for seamless indoor-outdoor living. The chef’s kitchen offers ample cabinetry, expansive countertops, a center island with secondary sink, walk-in pantry, and a breakfast nook with more French doors to the lanai. On the main floor, the primary suite includes a spa-inspired bath with double vanities, garden tub, and multiple closets. A guest suite also on the first floor includes a private bath, beverage fridge, and coffee station. A full laundry room and butler’s pantry with wine fridge complete the first level. Upstairs features a large loft with built-in cabinetry, under-cabinet lighting, and a beverage fridge. A built-in desk and cabinets line the hallway for study or work space. Two bedrooms share a Jack and Jill bath, and a third has access to a nearby full bath. A second laundry room, currently used as an office, adds flexibility. Step outside to a private backyard oasis with a screened lanai, sparkling pool, outdoor kitchen, mature landscaping, and full pool bathroom. With a new roof (2023), commercial grade water heater (2022), fresh exterior paint (2024) and many upgrades, this home offers turnkey living in one of Winter Park’s finest communities.

1355 Hibiscus Avenue, Winter Park

$2,288,215

A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light-filled great room w/ expansive lake-facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full-height backsplash. Sleek, dark wood, high-gloss cabinetry conceals a panel-ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under-cabinet lighting, geometric black-&-white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in-ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the home—overlooking the lake & appointed w/ custom built-ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron-patterned hardwood floors & tailored sisal carpets. The main level includes two en-suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique-style closets & a spa-quality bath w/ a custom vanity, dual undermount sinks, lucite-&-metal hardware, black quartz counters & full-height mirrors w/ integrated lighting. A glass-enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black-&-white subway tile, gold sunburst mirror & a walk-in frameless glass shower—ideal for guests or extended stays. Upstairs, a third en-suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver-toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wall—complete w/ a tucked-away water closet for added privacy. Additional features include Nest-controlled dual HVAC, 80-gallon stainless water heater w/ booster, Everpure filtration, Jeld-Wen impact-rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slips—all just minutes from Park Avenue.

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

A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light-filled great room w/ expansive lake-facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full-height backsplash. Sleek, dark wood, high-gloss cabinetry conceals a panel-ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under-cabinet lighting, geometric black-&-white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in-ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the home—overlooking the lake & appointed w/ custom built-ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron-patterned hardwood floors & tailored sisal carpets. The main level includes two en-suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique-style closets & a spa-quality bath w/ a custom vanity, dual undermount sinks, lucite-&-metal hardware, black quartz counters & full-height mirrors w/ integrated lighting. A glass-enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black-&-white subway tile, gold sunburst mirror & a walk-in frameless glass shower—ideal for guests or extended stays. Upstairs, a third en-suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver-toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wall—complete w/ a tucked-away water closet for added privacy. Additional features include Nest-controlled dual HVAC, 80-gallon stainless water heater w/ booster, Everpure filtration, Jeld-Wen impact-rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slips—all just minutes from Park Avenue.

1602 Alabama Drive Unit PH404, Winter Park

$1,300,000

**DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON MARKET DUE TO BUYERS FINANCING.** Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave! Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of Lakes, this home defines luxury living. Step through the impressive cut beveled glass double front doors into an interior filled with natural light, featuring hardwood floors, crown molding, recessed lighting, and blinds and Roman shades throughout. Formal living and dining rooms provide an elegant backdrop for entertaining, while the fireplace in the family room adds a cozy touch. Sliding French doors and two sets of large sliders seamlessly extend the living space to the private pool area. A sunroom (added in 2024) with a mini split system offers additional space to relax and unwind. Enjoy modern upgrades including a monitored security system, intercom system, reverse osmosis water filtration, and a water softener system. The gourmet kitchen is a chef’s dream with custom wood cabinetry, wavy tiled backsplash, granite countertops, stainless appliances including a newer refrigerator (2024) and newer dishwasher (2022), a gas stove, and two pantries, including a walk-in pantry. The breakfast nook and breakfast bar with seating for three creates plenty of space for gathering. Retreat to the luxurious primary suite with wood floors, a large walk-in closet, and a spa-like ensuite bathroom featuring double split vanities, a garden soaking tub, a large tiled shower, and a private water closet. Enjoy your own private backyard paradise on a .26-acre lot with a resort-style in-ground pool (2021), waterfall feature, sun shelf, lush landscaping, and irrigation system. An electronic front gate provides peace of mind for security as you're guided to a paved driveway and parking pad with a 2-car garage to complete this exceptional property. All this in a highly sought-after location, just minutes from Park Avenue’s high end shops and fine dining restaurants, Rollins College/Dinky Dock public boat ramp, Winter Park 9 Golf Club, Winter Park Racquet Club, Interlachen Country Club, Winter Park YMCA and WP Phelps Park and playground and so much more! Don’t miss your chance to own a piece of Winter Park’s finest! Schedule your private tour today. (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004)

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

**DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON MARKET DUE TO BUYERS FINANCING.** Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave! Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of Lakes, this home defines luxury living. Step through the impressive cut beveled glass double front doors into an interior filled with natural light, featuring hardwood floors, crown molding, recessed lighting, and blinds and Roman shades throughout. Formal living and dining rooms provide an elegant backdrop for entertaining, while the fireplace in the family room adds a cozy touch. Sliding French doors and two sets of large sliders seamlessly extend the living space to the private pool area. A sunroom (added in 2024) with a mini split system offers additional space to relax and unwind. Enjoy modern upgrades including a monitored security system, intercom system, reverse osmosis water filtration, and a water softener system. The gourmet kitchen is a chef’s dream with custom wood cabinetry, wavy tiled backsplash, granite countertops, stainless appliances including a newer refrigerator (2024) and newer dishwasher (2022), a gas stove, and two pantries, including a walk-in pantry. The breakfast nook and breakfast bar with seating for three creates plenty of space for gathering. Retreat to the luxurious primary suite with wood floors, a large walk-in closet, and a spa-like ensuite bathroom featuring double split vanities, a garden soaking tub, a large tiled shower, and a private water closet. Enjoy your own private backyard paradise on a .26-acre lot with a resort-style in-ground pool (2021), waterfall feature, sun shelf, lush landscaping, and irrigation system. An electronic front gate provides peace of mind for security as you're guided to a paved driveway and parking pad with a 2-car garage to complete this exceptional property. All this in a highly sought-after location, just minutes from Park Avenue’s high end shops and fine dining restaurants, Rollins College/Dinky Dock public boat ramp, Winter Park 9 Golf Club, Winter Park Racquet Club, Interlachen Country Club, Winter Park YMCA and WP Phelps Park and playground and so much more! Don’t miss your chance to own a piece of Winter Park’s finest! Schedule your private tour today. (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004)

1420 Palmer Avenue, Winter Park

$4,750,000

Welcome home to a gated estate on one of the most desired streets in Winter Park, on a half-acre with a separate guesthouse & walk in wine cellar and tasting room, & a short distance to Park Avenue, Kraft Azalea Gardens and Winter Park Racquet Club. Timeless elegance and flawless artistry blend perfectly with modern comfort and function in this one-of-a-kind custom home originally designed for the Mayor of Winter Park in the 1920s. Designed by Slocum Platts Architects, renovated by Clayton Homes and recently modernized and maintained by E2 Homes, this residence has been immaculately cared for and appointed for the most discerning buyer.

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

Welcome home to a gated estate on one of the most desired streets in Winter Park, on a half-acre with a separate guesthouse & walk in wine cellar and tasting room, & a short distance to Park Avenue, Kraft Azalea Gardens and Winter Park Racquet Club. Timeless elegance and flawless artistry blend perfectly with modern comfort and function in this one-of-a-kind custom home originally designed for the Mayor of Winter Park in the 1920s. Designed by Slocum Platts Architects, renovated by Clayton Homes and recently modernized and maintained by E2 Homes, this residence has been immaculately cared for and appointed for the most discerning buyer.

984 Mayfield Avenue, Winter Park

$2,100,000

Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and restaurants of Park Avenue, the residence welcomes with a paver circular drive and a private, gated side entry leading to a detached two-car garage. A brick-clad front porch and mature landscaping frame the formal entry, setting a tone of architectural distinction. Inside, a gallery-style foyer showcases designer wallpaper and salvaged pew rail detailing from a New York City church. The formal living room offers a stately gas fireplace, bespoke built-ins, and a large fixed window framing the lake, ideally suited for a quiet reading nook. The adjacent sunroom, encased in fixed glass, captures the surrounding canopy and lake vistas in all seasons. A generous dining room with custom dry bar, underlit floating shelving, and beverage refrigeration provides an ideal setting for elegant entertaining. The gourmet kitchen is thoughtfully appointed with paneled appliances including refrigerator and freezer columns, refrigerator drawers and a microwave drawer. Additional features include natural gas cooking, double ovens, and a sun-drenched breakfast room opening to the rear terrace and lap pool. A Dutch door entry offers functional access for daily living, while the basement below presents an opportunity for climate-controlled wine storage. The upstairs primary suite exudes comfort and sophistication with its gas fireplace, walk-in closet illuminated by a lake-facing window, a private covered balcony, and a spa-inspired bath with dual vanities, soaking tub, steam shower and private water closet. Two additional guest rooms with a Jack and Jill bath complete the upper level. Extensive renovations include a newer roof, Andersen windows and doors, two HVAC systems, full re-piping and rewiring, fresh paint, lighting, a newly installed pool heater and Hardie board siding—all executed within the last five years. The walk-up attic and pristine basement offer rare additional storage. Refinished hardwood floors throughout provide a consistent, elegant backdrop. This residence is a compelling blend of character, craftsmanship and contemporary living.

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

Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and restaurants of Park Avenue, the residence welcomes with a paver circular drive and a private, gated side entry leading to a detached two-car garage. A brick-clad front porch and mature landscaping frame the formal entry, setting a tone of architectural distinction. Inside, a gallery-style foyer showcases designer wallpaper and salvaged pew rail detailing from a New York City church. The formal living room offers a stately gas fireplace, bespoke built-ins, and a large fixed window framing the lake, ideally suited for a quiet reading nook. The adjacent sunroom, encased in fixed glass, captures the surrounding canopy and lake vistas in all seasons. A generous dining room with custom dry bar, underlit floating shelving, and beverage refrigeration provides an ideal setting for elegant entertaining. The gourmet kitchen is thoughtfully appointed with paneled appliances including refrigerator and freezer columns, refrigerator drawers and a microwave drawer. Additional features include natural gas cooking, double ovens, and a sun-drenched breakfast room opening to the rear terrace and lap pool. A Dutch door entry offers functional access for daily living, while the basement below presents an opportunity for climate-controlled wine storage. The upstairs primary suite exudes comfort and sophistication with its gas fireplace, walk-in closet illuminated by a lake-facing window, a private covered balcony, and a spa-inspired bath with dual vanities, soaking tub, steam shower and private water closet. Two additional guest rooms with a Jack and Jill bath complete the upper level. Extensive renovations include a newer roof, Andersen windows and doors, two HVAC systems, full re-piping and rewiring, fresh paint, lighting, a newly installed pool heater and Hardie board siding—all executed within the last five years. The walk-up attic and pristine basement offer rare additional storage. Refinished hardwood floors throughout provide a consistent, elegant backdrop. This residence is a compelling blend of character, craftsmanship and contemporary living.

104 Cortland Avenue, Winter Park

$234,000

One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Back on Market. Buyer financing fell through. Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen appliances, and a complete interior fresh coat of paint. Central heat/air was also added by the current owner to the screened in patio/balcony, including a closed off air duct to the balcony/patio, should you want to enclose the area. With a partial lake view from the patio, all you have to do to embrace nature is step outside your front door. This unit includes 1 parking space and visitor parking as well. Other amenities include the community pool, which overlooks Lake Killarney, a private loading dock for the boating expert in you, shuffleboard courts, grilling stations, and scenic outdoor seating areas, perfect for picnics, romantic sunsets, and daily meditation. HOA options for boat parking and dedicated kayak storage based upon availability. Located next door to Trader Joe’s and across from Winter Park Village, this condo offers convenient access to premier shopping, dining, and entertainment. Take a boat ride to Hillstone for happy hour or a delicious meal, relax in the pool while watching the sunset, or read a book under one of the park trees. Book your showing today and begin your ultimate lake life living!

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Back on Market. Buyer financing fell through. Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen appliances, and a complete interior fresh coat of paint. Central heat/air was also added by the current owner to the screened in patio/balcony, including a closed off air duct to the balcony/patio, should you want to enclose the area. With a partial lake view from the patio, all you have to do to embrace nature is step outside your front door. This unit includes 1 parking space and visitor parking as well. Other amenities include the community pool, which overlooks Lake Killarney, a private loading dock for the boating expert in you, shuffleboard courts, grilling stations, and scenic outdoor seating areas, perfect for picnics, romantic sunsets, and daily meditation. HOA options for boat parking and dedicated kayak storage based upon availability. Located next door to Trader Joe’s and across from Winter Park Village, this condo offers convenient access to premier shopping, dining, and entertainment. Take a boat ride to Hillstone for happy hour or a delicious meal, relax in the pool while watching the sunset, or read a book under one of the park trees. Book your showing today and begin your ultimate lake life living!

151 N Orlando Avenue Unit 204, Winter Park

$420,000

Your Opportunity is Here! Renovate this duplex and begin renting both sides or live in one and rent the other! Fenced yard, septic tank and large carport.

4 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Your Opportunity is Here! Renovate this duplex and begin renting both sides or live in one and rent the other! Fenced yard, septic tank and large carport.

1618 Indiana Avenue, Winter Park

$780,000

Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet, this haven of light and serenity is designed to accentuate its breathtaking views. The primary suite is a harmonious retreat featuring an en-suite bath, a spacious dressing area with ample closet space, and potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen opens to a generous living and dining area, offering picturesque views of glistening Lake Osceola – perfect for intimate gatherings or quiet evenings at home. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Exclusive amenities such as covered parking with a dedicated space conveniently close to the elevator, enhance the living experience. Additionally, boat docks, a gym, and an elegant community room within the complex provide leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the rare opportunity to own a unit with one of the most desirable water views in The Cloisters. Schedule your private viewing today and discover how this exceptional residence can become your canvas for an extraordinary life.

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

Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet, this haven of light and serenity is designed to accentuate its breathtaking views. The primary suite is a harmonious retreat featuring an en-suite bath, a spacious dressing area with ample closet space, and potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen opens to a generous living and dining area, offering picturesque views of glistening Lake Osceola – perfect for intimate gatherings or quiet evenings at home. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Exclusive amenities such as covered parking with a dedicated space conveniently close to the elevator, enhance the living experience. Additionally, boat docks, a gym, and an elegant community room within the complex provide leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the rare opportunity to own a unit with one of the most desirable water views in The Cloisters. Schedule your private viewing today and discover how this exceptional residence can become your canvas for an extraordinary life.

106 S Interlachen Avenue Unit 317, Winter Park

$2,550,000

1440 Place Picardy, Winter Park, FL Custom-Built Elegance with Timeless Finishes A custom-built residence completed in 2008 that blends classic craftsmanship with luxurious, modern living. From the moment you step inside, the superior millwork, solid hardwood floors, and elegant design details make a lasting impression. The gourmet kitchen is a chef’s dream, featuring marble countertops, an oversized gas range, and premium DCS and Sub-Zero appliances. It opens seamlessly to a warm and inviting living area, complete with custom built-ins and a cozy gas fireplace—perfect for entertaining or quiet evenings at home. The spacious primary suite is located on the main floor and boasts generous walk-in closets and a versatile adjoining room, ideal for a home office, nursery, or private retreat. Upstairs, you'll find three expansive bedrooms, three full bathrooms, and a versatile bonus room—perfect for guests, hobbies, or a playroom. Lovingly maintained, this home received a new roof in 2021 and features high-quality windows and doors throughout, bathing every room in natural light. No detail was overlooked. Step outside to your private, beautifully landscaped backyard, which includes a second gas fireplace and a detached flex room—currently used as a gym, but easily converted into a private office or studio space. The oversized three-car side-entry garage offers abundant storage and includes a Tesla charger—ideal for electric vehicle owners. Nestled on a peaceful street, this home is just minutes from everything Winter Park has to offer and is located within the highly sought-after Dommerich, Maitland, and Winter Park school zones. Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities.

5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

1440 Place Picardy, Winter Park, FL Custom-Built Elegance with Timeless Finishes A custom-built residence completed in 2008 that blends classic craftsmanship with luxurious, modern living. From the moment you step inside, the superior millwork, solid hardwood floors, and elegant design details make a lasting impression. The gourmet kitchen is a chef’s dream, featuring marble countertops, an oversized gas range, and premium DCS and Sub-Zero appliances. It opens seamlessly to a warm and inviting living area, complete with custom built-ins and a cozy gas fireplace—perfect for entertaining or quiet evenings at home. The spacious primary suite is located on the main floor and boasts generous walk-in closets and a versatile adjoining room, ideal for a home office, nursery, or private retreat. Upstairs, you'll find three expansive bedrooms, three full bathrooms, and a versatile bonus room—perfect for guests, hobbies, or a playroom. Lovingly maintained, this home received a new roof in 2021 and features high-quality windows and doors throughout, bathing every room in natural light. No detail was overlooked. Step outside to your private, beautifully landscaped backyard, which includes a second gas fireplace and a detached flex room—currently used as a gym, but easily converted into a private office or studio space. The oversized three-car side-entry garage offers abundant storage and includes a Tesla charger—ideal for electric vehicle owners. Nestled on a peaceful street, this home is just minutes from everything Winter Park has to offer and is located within the highly sought-after Dommerich, Maitland, and Winter Park school zones. Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities.

1400 Place Picardy, Winter Park

$1,635,000

Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 150-foot private drive with gate. Designed with comfortable yet sophisticated living space, this home is perfect for those seeking a serene retreat for both everyday living and entertainment. The heart of the home is the sizable kitchen, boasting a gas stove, high-end appliances, and a truly unique island crafted from reclaimed wood with a solid concrete countertop — a perfect blend of rustic charm and modern design. The primary retreat is conveniently located on the first floor, featuring a spa-like bathroom complete with a soaking tub and a spacious walk-in shower. Upstairs, you'll find two additional ensuite bedrooms with the 4th bedroom that doubles as a home office complete with built-in desk and murphy bed. A generously sized bonus room/living area upstairs provides additional flexibility for a media room, playroom, or home office. Outdoors, the professionally designed and illuminated landscaping sets a warm, welcoming tone which includes a spectacular 12' x 40' salt-filtered heated pool surrounded by a luxurious travertine deck with fire-pit. Close proximity to all the charm and amenities Winter Park has to offer. This exceptional home offers privacy, elegance, and thoughtful design at every turn. Call today for an easy showing!

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

Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 150-foot private drive with gate. Designed with comfortable yet sophisticated living space, this home is perfect for those seeking a serene retreat for both everyday living and entertainment. The heart of the home is the sizable kitchen, boasting a gas stove, high-end appliances, and a truly unique island crafted from reclaimed wood with a solid concrete countertop — a perfect blend of rustic charm and modern design. The primary retreat is conveniently located on the first floor, featuring a spa-like bathroom complete with a soaking tub and a spacious walk-in shower. Upstairs, you'll find two additional ensuite bedrooms with the 4th bedroom that doubles as a home office complete with built-in desk and murphy bed. A generously sized bonus room/living area upstairs provides additional flexibility for a media room, playroom, or home office. Outdoors, the professionally designed and illuminated landscaping sets a warm, welcoming tone which includes a spectacular 12' x 40' salt-filtered heated pool surrounded by a luxurious travertine deck with fire-pit. Close proximity to all the charm and amenities Winter Park has to offer. This exceptional home offers privacy, elegance, and thoughtful design at every turn. Call today for an easy showing!

2402.5 Temple Drive, Winter Park

$1,800,000

Modern living in Central Florida’s desirable Winter Park, this residence offers an elegant balance of refined design, elevated finishes and seamless indoor-outdoor living. Completed in 2021 and impeccably maintained, this two-story home features four generously sized bedrooms, a sun-filled private office, three-and-a-half baths, and an oversized two-car garage, equipped with EV charging, on a quarter acre close to dining, shopping, parks and entertainment. The exterior’s clean architectural profile creates striking curb appeal, while inside, a soaring foyer leads to an open-concept interior appointed with wide-plank hardwood flooring, designer lighting fixtures, custom window treatments, closed-circuit surveillance cameras and a premium integrated surround sound system. The expansive living and dining areas connect effortlessly with a sleek chef’s kitchen featuring professional-grade stainless steel gas appliances, full-height cabinetry and an oversized center island designed for entertaining in the heart of the home. Glass doors at the rear of the house open to a covered lanai and private backyard sanctuary complete with custom pavers, a resort-style graduated-entry pool, mature landscaping and fully fenced, ideal for entertaining or peaceful everyday enjoyment. A grand double-door entry to your first-floor primary suite offers tranquil pool views and a spa-inspired bath with a freestanding soaking tub, zero-entry shower, dual vanities and a custom walk-in closet with integrated storage systems and a private laundry station. Upstairs, three generously sized bedrooms, two elegantly appointed baths, a spacious laundry room and a versatile loft provide privacy and flexibility for guests and the whole family. In Winter Park just moments from A-rated schools, dining, boutiques and including East End Market and Baldwin Park offer additional access to artisan eateries, local shops and parks, this home has it all. Experience the elegance and lifestyle this home offers and reach out today to arrange your private showing.

4 Beds ⋅ 4 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Modern living in Central Florida’s desirable Winter Park, this residence offers an elegant balance of refined design, elevated finishes and seamless indoor-outdoor living. Completed in 2021 and impeccably maintained, this two-story home features four generously sized bedrooms, a sun-filled private office, three-and-a-half baths, and an oversized two-car garage, equipped with EV charging, on a quarter acre close to dining, shopping, parks and entertainment. The exterior’s clean architectural profile creates striking curb appeal, while inside, a soaring foyer leads to an open-concept interior appointed with wide-plank hardwood flooring, designer lighting fixtures, custom window treatments, closed-circuit surveillance cameras and a premium integrated surround sound system. The expansive living and dining areas connect effortlessly with a sleek chef’s kitchen featuring professional-grade stainless steel gas appliances, full-height cabinetry and an oversized center island designed for entertaining in the heart of the home. Glass doors at the rear of the house open to a covered lanai and private backyard sanctuary complete with custom pavers, a resort-style graduated-entry pool, mature landscaping and fully fenced, ideal for entertaining or peaceful everyday enjoyment. A grand double-door entry to your first-floor primary suite offers tranquil pool views and a spa-inspired bath with a freestanding soaking tub, zero-entry shower, dual vanities and a custom walk-in closet with integrated storage systems and a private laundry station. Upstairs, three generously sized bedrooms, two elegantly appointed baths, a spacious laundry room and a versatile loft provide privacy and flexibility for guests and the whole family. In Winter Park just moments from A-rated schools, dining, boutiques and including East End Market and Baldwin Park offer additional access to artisan eateries, local shops and parks, this home has it all. Experience the elegance and lifestyle this home offers and reach out today to arrange your private showing.

2813 Northwood Boulevard, Winter Park

$600,000

Value is in the land.

3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Value is in the land.

1550 Palm Avenue, Winter Park

$645,000

Welcome to 796 McIntyre Avenue, Winter Park, FL 32789. This stunning and serene retreat is the ideal place to call home, perfectly situated on a tree-lined brick street within walking distance to Rollins College and all that Park Avenue has to offer. A charming driveway leads to your two-car garage and private front entrance. Upon entering, you'll be greeted by a bright and airy townhome that will instantly impress. The living room features a wood-burning fireplace, soaring ceilings with high windows, and is surrounded by two peaceful patios, bringing in abundant natural light. The updated kitchen offers modern cabinetry, an open breakfast bar, and a delightful eat-in area that opens to a patio. The formal dining room, currently used as a home office, provides access to the second patio, ideal for al fresco dining. Upstairs, you'll find an AMAZING 23x12 primary bedroom with a spacious 20x8 ensuite bathroom. Two guest suites with a Jack-and-Jill bathroom complete the second floor. The owner has meticulously maintained this lovely home, with new patio decks in 2018, a new HVAC, water heater, washer/dryer in 2019, new ceiling fans and refrigerator in 2020, and a new roof and skylights in 2021. Zoned for Audubon K-8 and Winter Park High School. Welcome home!

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

Welcome to 796 McIntyre Avenue, Winter Park, FL 32789. This stunning and serene retreat is the ideal place to call home, perfectly situated on a tree-lined brick street within walking distance to Rollins College and all that Park Avenue has to offer. A charming driveway leads to your two-car garage and private front entrance. Upon entering, you'll be greeted by a bright and airy townhome that will instantly impress. The living room features a wood-burning fireplace, soaring ceilings with high windows, and is surrounded by two peaceful patios, bringing in abundant natural light. The updated kitchen offers modern cabinetry, an open breakfast bar, and a delightful eat-in area that opens to a patio. The formal dining room, currently used as a home office, provides access to the second patio, ideal for al fresco dining. Upstairs, you'll find an AMAZING 23x12 primary bedroom with a spacious 20x8 ensuite bathroom. Two guest suites with a Jack-and-Jill bathroom complete the second floor. The owner has meticulously maintained this lovely home, with new patio decks in 2018, a new HVAC, water heater, washer/dryer in 2019, new ceiling fans and refrigerator in 2020, and a new roof and skylights in 2021. Zoned for Audubon K-8 and Winter Park High School. Welcome home!

796 Mcintyre Avenue, Winter Park

$1,375,000

This home is a charming and meticulously maintained single-story family home nestled on a quiet street located on an expansive beautifully landscaped lot. As you enter, you're greeted by a private office with French doors to the left, and to the right, a cozy family room featuring a decorative fireplace. The open concept living and dining areas overlook the backyard, creating a perfect flow for gatherings. The kitchen, which also overlooks the backyard, features granite countertops, wood cabinetry, and under cabinetry lighting. The home boasts beautiful bamboo flooring throughout most of the living spaces and it has been thoughtfully designed with crown molding and baseboards throughout. A split floor plan offers privacy with the primary suite located on one side of the home. The stunning master bathroom, remodeled in 2024, features a large soaking tub, dual vanities and a walk-in shower. Enjoy the massive walk-in closet with custom built-ins. The primary retreat boasts vaulted wood plank ceilings and French doors which open to the pool area, creating a true retreat. On the opposite side of the home, you’ll find three additional bedrooms, all with built-in closets. The largest of these bedrooms has an ensuite bath, while the other two share a bath with a tub and shower combo. There is also a convenient half-bath off the family room, perfect for guests. The home sits on a spacious, over quarter acre lot, offering a massive backyard oasis complete with a saltwater pool, spa, and a covered patio area perfect for entertaining. The backyard is an entertainer’s dream with a summer kitchen, bar fridge, sink, and wood plank ceiling over the covered patio. The fully fenced yard offers plenty of space for outdoor activities. Additional updates include a 2021 roof, 2021 a/c for primary bedroom, 2024 a/c for main house and exterior paint in 2022, primary retreat and wing added in 2013. The home is located within a highly sought-after Winter Park neighborhood. It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue.

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

This home is a charming and meticulously maintained single-story family home nestled on a quiet street located on an expansive beautifully landscaped lot. As you enter, you're greeted by a private office with French doors to the left, and to the right, a cozy family room featuring a decorative fireplace. The open concept living and dining areas overlook the backyard, creating a perfect flow for gatherings. The kitchen, which also overlooks the backyard, features granite countertops, wood cabinetry, and under cabinetry lighting. The home boasts beautiful bamboo flooring throughout most of the living spaces and it has been thoughtfully designed with crown molding and baseboards throughout. A split floor plan offers privacy with the primary suite located on one side of the home. The stunning master bathroom, remodeled in 2024, features a large soaking tub, dual vanities and a walk-in shower. Enjoy the massive walk-in closet with custom built-ins. The primary retreat boasts vaulted wood plank ceilings and French doors which open to the pool area, creating a true retreat. On the opposite side of the home, you’ll find three additional bedrooms, all with built-in closets. The largest of these bedrooms has an ensuite bath, while the other two share a bath with a tub and shower combo. There is also a convenient half-bath off the family room, perfect for guests. The home sits on a spacious, over quarter acre lot, offering a massive backyard oasis complete with a saltwater pool, spa, and a covered patio area perfect for entertaining. The backyard is an entertainer’s dream with a summer kitchen, bar fridge, sink, and wood plank ceiling over the covered patio. The fully fenced yard offers plenty of space for outdoor activities. Additional updates include a 2021 roof, 2021 a/c for primary bedroom, 2024 a/c for main house and exterior paint in 2022, primary retreat and wing added in 2013. The home is located within a highly sought-after Winter Park neighborhood. It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue.

1633 Pine Avenue, Winter Park

$550,000

Location, Charm, and Potential! Presenting a rare opportunity to own a home in one of Winter Park's most prestigious zip codes, offering the perfect blend of classic elegance and future potential. This 4-bedroom, 2.5-bathroom pool home is ready for your personal touch and vision. Nestled on a large corner lot in a highly sought-after neighborhood, this home features timeless charm and all the structural bones you need to create your dream living space. As you approach the home via the charming brick-paved walkway, step inside to a welcoming foyer. The spacious formal living room is bright and inviting, showcasing a marble wood-burning fireplace and French doors that lead out to the backyard—perfect for entertaining. Adjacent to the living room, the formal dining room offers ample space for large gatherings and dinner parties. The kitchen provides plenty of storage and potential to become a chef’s paradise, with generous cabinetry and counter space. Overlooking the cozy family room with parquet flooring, the space is ideal for relaxing, watching movies, or enjoying family game night. The bedrooms offer privacy and comfort, with the primary suite serving as a peaceful retreat. The spacious primary bedroom features ample closet space and an ensuite bathroom with double sinks, a private water closet, and a walk-in shower. Additional highlights include hurricane windows installed just five years ago, offering peace of mind and letting natural light flood the space. Timeless terrazzo flooring can be found throughout the home. The backyard is a private oasis, with mature landscaping and a well-maintained pool—perfect for relaxing or entertaining guests. Located just minutes from Winter Park’s renowned Park Avenue, with its upscale shops and dining, this home is an exceptional find. Don’t miss out on the chance to invest in a home with incredible potential in one of Winter Park’s most desirable neighborhoods! ROOF - 3/2025 (brand new!), HVAC 2010, ELECTRICAL - 2022 **WE ARE ACCEPTING ANY AND ALL OFFERS THROUGH 9AM MONDAY APRIL 7, 2025.***

4 Beds ⋅ 3 Baths ⋅ Dommerich Hills Fourth Add SubDv. ⋅ 32789 Zip Code

Location, Charm, and Potential! Presenting a rare opportunity to own a home in one of Winter Park's most prestigious zip codes, offering the perfect blend of classic elegance and future potential. This 4-bedroom, 2.5-bathroom pool home is ready for your personal touch and vision. Nestled on a large corner lot in a highly sought-after neighborhood, this home features timeless charm and all the structural bones you need to create your dream living space. As you approach the home via the charming brick-paved walkway, step inside to a welcoming foyer. The spacious formal living room is bright and inviting, showcasing a marble wood-burning fireplace and French doors that lead out to the backyard—perfect for entertaining. Adjacent to the living room, the formal dining room offers ample space for large gatherings and dinner parties. The kitchen provides plenty of storage and potential to become a chef’s paradise, with generous cabinetry and counter space. Overlooking the cozy family room with parquet flooring, the space is ideal for relaxing, watching movies, or enjoying family game night. The bedrooms offer privacy and comfort, with the primary suite serving as a peaceful retreat. The spacious primary bedroom features ample closet space and an ensuite bathroom with double sinks, a private water closet, and a walk-in shower. Additional highlights include hurricane windows installed just five years ago, offering peace of mind and letting natural light flood the space. Timeless terrazzo flooring can be found throughout the home. The backyard is a private oasis, with mature landscaping and a well-maintained pool—perfect for relaxing or entertaining guests. Located just minutes from Winter Park’s renowned Park Avenue, with its upscale shops and dining, this home is an exceptional find. Don’t miss out on the chance to invest in a home with incredible potential in one of Winter Park’s most desirable neighborhoods! ROOF - 3/2025 (brand new!), HVAC 2010, ELECTRICAL - 2022 **WE ARE ACCEPTING ANY AND ALL OFFERS THROUGH 9AM MONDAY APRIL 7, 2025.***

2906 Rapidan Trail, Winter Park

$540,000

Situated in a prime location, this condominium presents an excellent opportunity for customization and renovation. Sold as-is, this residence offers a spacious layout with ample potential to reimagine its interiors to suit modern living. Positioned within The Cloisters sought-after community, residents enjoy access to desirable amenities and a convenient setting near shopping, dining, and local attractions. A rare chance to transform and tailor a space to individual preferences.

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

Situated in a prime location, this condominium presents an excellent opportunity for customization and renovation. Sold as-is, this residence offers a spacious layout with ample potential to reimagine its interiors to suit modern living. Positioned within The Cloisters sought-after community, residents enjoy access to desirable amenities and a convenient setting near shopping, dining, and local attractions. A rare chance to transform and tailor a space to individual preferences.

100 S Interlachen Avenue Unit 415, 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

$3,550,000

This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful Lake Osceola. Whether you enjoy watersports, boating, or simply relaxing by the water, this property can provide the true joy of lakefront living. The grandfathered boat dock provides a rare opportunity for transformation, perfect for customizing your ideal lakeside retreat. The home boasts breathtaking lake views from the primary retreat, family room, dining room, and Florida room, providing a seamless connection to nature. Upon entering, you're greeted by a spacious living room that flows effortlessly into the family room. Adjacent to the living room is a formal dining room, ideal for entertaining guests. The expansive primary retreat has dual closets. Across from the primary, a generously sized bedroom features its own ensuite bathroom. The kitchen, located off the dining room, also captures stunning views of the lake, making it a delightful space. An additional bedroom with an ensuite bathroom provides privacy and comfort, while a half bath is conveniently located near this bedroom. A second half bathroom is situated in the garage. A recent update includes a new roof installed in 2022. The property spans .61 acres, providing plenty of room for future development. Located on one of Winter Park's most beautiful streets, this home is just a short walk from the charming shops and restaurants of Park Avenue and Rollins College. Experience the best of lakeside living and the vibrant Winter Park community from this stunning property. Opportunity awaits the buyer of this gorgeous property!

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

This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful Lake Osceola. Whether you enjoy watersports, boating, or simply relaxing by the water, this property can provide the true joy of lakefront living. The grandfathered boat dock provides a rare opportunity for transformation, perfect for customizing your ideal lakeside retreat. The home boasts breathtaking lake views from the primary retreat, family room, dining room, and Florida room, providing a seamless connection to nature. Upon entering, you're greeted by a spacious living room that flows effortlessly into the family room. Adjacent to the living room is a formal dining room, ideal for entertaining guests. The expansive primary retreat has dual closets. Across from the primary, a generously sized bedroom features its own ensuite bathroom. The kitchen, located off the dining room, also captures stunning views of the lake, making it a delightful space. An additional bedroom with an ensuite bathroom provides privacy and comfort, while a half bath is conveniently located near this bedroom. A second half bathroom is situated in the garage. A recent update includes a new roof installed in 2022. The property spans .61 acres, providing plenty of room for future development. Located on one of Winter Park's most beautiful streets, this home is just a short walk from the charming shops and restaurants of Park Avenue and Rollins College. Experience the best of lakeside living and the vibrant Winter Park community from this stunning property. Opportunity awaits the buyer of this gorgeous property!

443 Lakewood Drive, Winter Park

$4,500,000

"The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a peninsula with .90 acres and over 440+ feet of lake frontage with unobstructed lake views to the south, west and east. Constructed in 2012, this home features 6,000 living square footage (3,977 on the 1st level / 1,950 on the 2nd level), 4,000 sq. ft. of outdoor space, elevator, infinity pool, boat house and tennis court. Main level offers 35 x 32 great room w/kitchen and dining, a separate dining area, 36 x 20 family room with bar/wine room, 4 bedrooms/ 3.5 baths, laundry room and 4 multi slider panel doors that open to wrap around patio with outdoor kitchen. 2nd floor offers a 2nd laundry room, lofted library, guest bedroom and primary bedroom with suite/lounge/built in wet bar and additional 4 multi slide panel doors that open to a wrap around balcony. Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset.

6 Beds ⋅ 6 Baths ⋅ Killarney Point SubDv. ⋅ 32789 Zip Code

"The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a peninsula with .90 acres and over 440+ feet of lake frontage with unobstructed lake views to the south, west and east. Constructed in 2012, this home features 6,000 living square footage (3,977 on the 1st level / 1,950 on the 2nd level), 4,000 sq. ft. of outdoor space, elevator, infinity pool, boat house and tennis court. Main level offers 35 x 32 great room w/kitchen and dining, a separate dining area, 36 x 20 family room with bar/wine room, 4 bedrooms/ 3.5 baths, laundry room and 4 multi slider panel doors that open to wrap around patio with outdoor kitchen. 2nd floor offers a 2nd laundry room, lofted library, guest bedroom and primary bedroom with suite/lounge/built in wet bar and additional 4 multi slide panel doors that open to a wrap around balcony. Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset.

2118 Lake Drive, Winter Park

$1,516,500

A special opportunity awaits on one of Winter Park’s most sought-after streets, BELOIT AVENUE! This charming 3-bedroom, 2-bathroom home is perfectly positioned just two blocks from the vibrant energy of Park Avenue and steps from the lush greens of the Winter Park 9 Golf Course. Brimming with character and warmth, this jewel box offers over 2,400 square feet of beautifully designed living space. High ceilings, elegant crown molding, and a seamless mix of tile and gleaming hardwood floors in every bedroom create a sense of lightness and luxury. The expansive family room extends off the back of the home, opening effortlessly to a screened-in patio, perfect for enjoying the Florida lifestyle year-round. With an ideal blend of charm, location, and livability, this home is a true treasure in the heart of Winter Park. Enter through the foyer and prepare for seamless indoor/outdoor entertaining, with an inviting living room and dining room, elegantly separated by a gorgeous double-sided gas fireplace, and lined with sliding glass doors that lead to the open, paver patio. The kitchen is complete with stainless steel appliances, a natural-gas cooktop, timeless cabinetry that offers an abundance of storage, and a built-in breakfast bar. You’ll love the ideal split-bedroom floor plan, featuring an oversized primary suite that overlooks the expansive side patio accessible through sliding glass doors. Off the front living room hallway are 2 secondary bedrooms with walk-in closets, and a full bathroom. Wrapped in low-maintenance landscaping with elegant uplighting, all surrounded by concrete privacy walls with gates, this turnkey home is perfect for an active lifestyle. A private alley drive for Beloit homeowners leads to a spacious 2-car garage with built-in cabinets and attic storage. Enjoy a NEW A/C unit (2024), new washer/dryer (2024), and one of the best locations in the City of Winter Park!!

3 Beds ⋅ 2 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code

A special opportunity awaits on one of Winter Park’s most sought-after streets, BELOIT AVENUE! This charming 3-bedroom, 2-bathroom home is perfectly positioned just two blocks from the vibrant energy of Park Avenue and steps from the lush greens of the Winter Park 9 Golf Course. Brimming with character and warmth, this jewel box offers over 2,400 square feet of beautifully designed living space. High ceilings, elegant crown molding, and a seamless mix of tile and gleaming hardwood floors in every bedroom create a sense of lightness and luxury. The expansive family room extends off the back of the home, opening effortlessly to a screened-in patio, perfect for enjoying the Florida lifestyle year-round. With an ideal blend of charm, location, and livability, this home is a true treasure in the heart of Winter Park. Enter through the foyer and prepare for seamless indoor/outdoor entertaining, with an inviting living room and dining room, elegantly separated by a gorgeous double-sided gas fireplace, and lined with sliding glass doors that lead to the open, paver patio. The kitchen is complete with stainless steel appliances, a natural-gas cooktop, timeless cabinetry that offers an abundance of storage, and a built-in breakfast bar. You’ll love the ideal split-bedroom floor plan, featuring an oversized primary suite that overlooks the expansive side patio accessible through sliding glass doors. Off the front living room hallway are 2 secondary bedrooms with walk-in closets, and a full bathroom. Wrapped in low-maintenance landscaping with elegant uplighting, all surrounded by concrete privacy walls with gates, this turnkey home is perfect for an active lifestyle. A private alley drive for Beloit homeowners leads to a spacious 2-car garage with built-in cabinets and attic storage. Enjoy a NEW A/C unit (2024), new washer/dryer (2024), and one of the best locations in the City of Winter Park!!

335 Beloit Avenue, Winter Park

$380,000

Winter Park location with access to Lake Killarney & walking distance to Trader Joes & Winter Park Village. Renovated 2 bedroom 2.5 bath 2 story condo with Pool & lake view amenities. Gorgeous wood floors throughout, Granite counters, Stainless Steele appliances , Soft close cabinets & glass tile backsplash. Inside Laundry room with Washer/Dryer included. Under stair storage. Wood burning Fire place, Bar sink, Ceiling Fans, Both bedrooms have large walk-in closets and the primary has a walk out balcony patio. The Primary bath offers double shower heads & double vanity. Outside Storage closet & Enclosed screen patio. The pool is set with majestic sunset views of the lake where you can fish off the dock or kayak the lake. HOA updates include repaved asphalt parking & exterior paint, dock repainted & pool sealant in 2020. Fees include exterior maintenance, pool, dock & trash.

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

Winter Park location with access to Lake Killarney & walking distance to Trader Joes & Winter Park Village. Renovated 2 bedroom 2.5 bath 2 story condo with Pool & lake view amenities. Gorgeous wood floors throughout, Granite counters, Stainless Steele appliances , Soft close cabinets & glass tile backsplash. Inside Laundry room with Washer/Dryer included. Under stair storage. Wood burning Fire place, Bar sink, Ceiling Fans, Both bedrooms have large walk-in closets and the primary has a walk out balcony patio. The Primary bath offers double shower heads & double vanity. Outside Storage closet & Enclosed screen patio. The pool is set with majestic sunset views of the lake where you can fish off the dock or kayak the lake. HOA updates include repaved asphalt parking & exterior paint, dock repainted & pool sealant in 2020. Fees include exterior maintenance, pool, dock & trash.

350 Killarney Bay Court Unit 5, Winter Park

$685,000

Experience a lifestyle of refined sophistication and effortless tranquility at The Cloisters Condominium, ideally between Park Avenue and the serene shores of Lake Osceola. This exquisitely remodeled residence offers a seamless blend of timeless elegance and thoughtful design. Set on the second floor, this sun-drenched retreat is bathed in natural light from its northeast-facing sunroom, where expansive windows frame picturesque views of the lush gardens and pool, creating an inviting ambiance throughout the living space. Rich wood floors flow gracefully through the open layout, enhancing the home’s warm and sophisticated character. The primary suite is a private haven, featuring custom-built cabinetry and drawers, a dressing area with abundant closet space and a beautifully updated en-suite bath. A dedicated laundry closet with a built-in washer and dryer adds everyday convenience. The second bedroom offers a custom-built office setup and dual access from the hall and living area, providing effortless versatility as a bedroom, sitting room or private study. The Cloisters offers an array of exclusive amenities designed to elevate everyday living. Guest parking is immediately below the unit in the forward parking circle, as well as along Morse Boulevard, ensuring seamless accessibility for visitors. Additional perks include an assigned covered parking space near the elevator, a dock with boat slips available for lease, two well-appointed fitness rooms, and a beautifully redesigned community space featuring a newly remodeled kitchen and bath. Just steps from the vibrant energy of Park Avenue, this exceptional home provides unparalleled access to fine dining, boutique shopping, cultural attractions, fitness centers and the distinguished Rollins College. Every detail has been carefully curated to create an extraordinary living experience in the heart of Winter Park. Seize this rare opportunity to own a desirable residence at The Cloisters, schedule your private tour today and embrace a home where elegance meets effortless living.

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

Experience a lifestyle of refined sophistication and effortless tranquility at The Cloisters Condominium, ideally between Park Avenue and the serene shores of Lake Osceola. This exquisitely remodeled residence offers a seamless blend of timeless elegance and thoughtful design. Set on the second floor, this sun-drenched retreat is bathed in natural light from its northeast-facing sunroom, where expansive windows frame picturesque views of the lush gardens and pool, creating an inviting ambiance throughout the living space. Rich wood floors flow gracefully through the open layout, enhancing the home’s warm and sophisticated character. The primary suite is a private haven, featuring custom-built cabinetry and drawers, a dressing area with abundant closet space and a beautifully updated en-suite bath. A dedicated laundry closet with a built-in washer and dryer adds everyday convenience. The second bedroom offers a custom-built office setup and dual access from the hall and living area, providing effortless versatility as a bedroom, sitting room or private study. The Cloisters offers an array of exclusive amenities designed to elevate everyday living. Guest parking is immediately below the unit in the forward parking circle, as well as along Morse Boulevard, ensuring seamless accessibility for visitors. Additional perks include an assigned covered parking space near the elevator, a dock with boat slips available for lease, two well-appointed fitness rooms, and a beautifully redesigned community space featuring a newly remodeled kitchen and bath. Just steps from the vibrant energy of Park Avenue, this exceptional home provides unparalleled access to fine dining, boutique shopping, cultural attractions, fitness centers and the distinguished Rollins College. Every detail has been carefully curated to create an extraordinary living experience in the heart of Winter Park. Seize this rare opportunity to own a desirable residence at The Cloisters, schedule your private tour today and embrace a home where elegance meets effortless living.

100 S Interlachen Avenue Unit 203, Winter Park

$1,555,000

Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality and charm. This thoughtfully designed home boasts detailed moldings and millwork, wood floors, high ceilings, and beautiful oversized windows throughout. A grand foyer leads to a central gallery with an atrium and a custom-designed bannister, while a unique glass ceiling allows for an abundance of natural light. Perfect for entertaining, the home features a large dining room and a chef's kitchen equipped with professional-style appliances, a walk-in pantry, and a built-in banquette. The spacious family room, complete with a fireplace, has French doors that open to a charming outdoor terrace. The versatile floor plan incorporates both formal spaces and options for a home office, nursery, or music room. The main home includes four bedrooms and three baths. The upstairs primary suite is a luxurious retreat, offering a spa-like bath, an oversized closet with built-ins, and a separate room perfect for an office or nursery. The large secondary bedrooms have walk-in closets and are connected by a Jack and Jill bath. Your guests will appreciate the detached apartment, which offers privacy with a full bath, kitchen, and separate courtyard—ideal as a fifth bedroom. Situated on one of Winter Park’s most charming brick streets in the historic College Quarter, this home is just a short stroll to a private neighborhood dock on Lake Virginia. Walk to Park Avenue’s shops and restaurants, Rollins College, the farmer's market, and the Sunrail station. The home celebrates its Federalist architecture with precise and thoughtful details while seamlessly integrating modern amenities. Additional features include an oversized side-entry two-car garage, a new roof installed in 2022, and many windows replaced in 2020. This property is zoned for top-rated schools, including Audubon K-8 and Winter Park High School. Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure!

4 Beds ⋅ 3 Baths ⋅ College Place Rep SubDv. ⋅ 32789 Zip Code

Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality and charm. This thoughtfully designed home boasts detailed moldings and millwork, wood floors, high ceilings, and beautiful oversized windows throughout. A grand foyer leads to a central gallery with an atrium and a custom-designed bannister, while a unique glass ceiling allows for an abundance of natural light. Perfect for entertaining, the home features a large dining room and a chef's kitchen equipped with professional-style appliances, a walk-in pantry, and a built-in banquette. The spacious family room, complete with a fireplace, has French doors that open to a charming outdoor terrace. The versatile floor plan incorporates both formal spaces and options for a home office, nursery, or music room. The main home includes four bedrooms and three baths. The upstairs primary suite is a luxurious retreat, offering a spa-like bath, an oversized closet with built-ins, and a separate room perfect for an office or nursery. The large secondary bedrooms have walk-in closets and are connected by a Jack and Jill bath. Your guests will appreciate the detached apartment, which offers privacy with a full bath, kitchen, and separate courtyard—ideal as a fifth bedroom. Situated on one of Winter Park’s most charming brick streets in the historic College Quarter, this home is just a short stroll to a private neighborhood dock on Lake Virginia. Walk to Park Avenue’s shops and restaurants, Rollins College, the farmer's market, and the Sunrail station. The home celebrates its Federalist architecture with precise and thoughtful details while seamlessly integrating modern amenities. Additional features include an oversized side-entry two-car garage, a new roof installed in 2022, and many windows replaced in 2020. This property is zoned for top-rated schools, including Audubon K-8 and Winter Park High School. Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure!

817 Antonette Avenue, Winter Park

$1,625,000

Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via’s, this stunning 5-bedroom, 4 full bath, 2 half bath traditional home offers over 4,200 sq. ft. of refined living space. With timeless architectural details, modern upgrades, and an unbeatable location just minutes from Park Avenue’s shops and restaurants, this home is a rare find. Step inside to find newly refinished Brazilian Rosewood floors throughout the main living areas. The formal living room features a wood-burning fireplace and two sets of French doors that open to a covered lanai with a remote-controlled motorized screen, perfect for seamless indoor-outdoor living. The formal dining room sets the stage for elegant entertaining, while the spacious open-concept kitchen overlooks the family room. Designed for the culinary enthusiast, the kitchen boasts an Italian porcelain island, a brand-new Kucht Professional 8-burner gas range/oven, double ovens, and a walk-in pantry. The family room offers another wood-burning fireplace and French doors leading to the screened-in saltwater heated pool, refinished just three years ago with new equipment. The first-floor primary suite is a true retreat, featuring serene pool views, a large walk-in closet with California Closet system, and a spacious en-suite bath. Two additional first-floor bedrooms, each with walk-in closets, provide comfort and convenience. Upstairs, a private bedroom, full bath, and large bonus room offer the perfect space for guests or a secondary living area, with easy access to walk-in attic storage. A two-car attached garage includes built-in storage and a private staircase leading to a guest apartment/bedroom suite complete with a wet bar and full bath—ideal for multi-generational living or an au pair. Outdoor living is at its finest with a covered lanai, new tile flooring, and a remote-controlled motorized screen, plus a poolside half bath and outdoor shower. Situated in a Grade A school district and offering easy access to major roadways, this exquisite home blends elegance, comfort, and prime location. Please see attachments for the full list of improvements.

5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via’s, this stunning 5-bedroom, 4 full bath, 2 half bath traditional home offers over 4,200 sq. ft. of refined living space. With timeless architectural details, modern upgrades, and an unbeatable location just minutes from Park Avenue’s shops and restaurants, this home is a rare find. Step inside to find newly refinished Brazilian Rosewood floors throughout the main living areas. The formal living room features a wood-burning fireplace and two sets of French doors that open to a covered lanai with a remote-controlled motorized screen, perfect for seamless indoor-outdoor living. The formal dining room sets the stage for elegant entertaining, while the spacious open-concept kitchen overlooks the family room. Designed for the culinary enthusiast, the kitchen boasts an Italian porcelain island, a brand-new Kucht Professional 8-burner gas range/oven, double ovens, and a walk-in pantry. The family room offers another wood-burning fireplace and French doors leading to the screened-in saltwater heated pool, refinished just three years ago with new equipment. The first-floor primary suite is a true retreat, featuring serene pool views, a large walk-in closet with California Closet system, and a spacious en-suite bath. Two additional first-floor bedrooms, each with walk-in closets, provide comfort and convenience. Upstairs, a private bedroom, full bath, and large bonus room offer the perfect space for guests or a secondary living area, with easy access to walk-in attic storage. A two-car attached garage includes built-in storage and a private staircase leading to a guest apartment/bedroom suite complete with a wet bar and full bath—ideal for multi-generational living or an au pair. Outdoor living is at its finest with a covered lanai, new tile flooring, and a remote-controlled motorized screen, plus a poolside half bath and outdoor shower. Situated in a Grade A school district and offering easy access to major roadways, this exquisite home blends elegance, comfort, and prime location. Please see attachments for the full list of improvements.

1470 Place Picardy, Winter Park

$1,255,000

An unparalleled opportunity to live in one of Orlando’s most desirable areas and in a truly dream-worthy home! This stunning 4-bedroom, 3-bathroom property, situated on a spacious 0.32-acre lot (13,814 square feet), has been completely remodeled with exceptional attention to detail. It boasts a custom Calacatta surface and brand-new stainless steel appliances, including a sleek glass cooktop, all cabinets come with soft-close drawers. The elegant two-tone cabinetry adds a custom touch that will impress your guests. The heart of the home is bathed in natural light thanks to a large front window in the dining area, creating an inviting atmosphere. Sliding glass doors connect the living space to the outdoor oasis, where you’ll find a spacious pool with a screened enclosure, a beautifully landscaped yard, and a cozy fire pit, perfect for relaxing or entertaining from the comfort of your own home. The dining area also features a convenient coffee bar that enhances functionality. Nestled in one of Winter Park’s most sought-after neighborhoods, this property is just minutes away from exclusive dining and boutique shopping. Zoned for top-rated Audubon K-8 and Winter Park High School, this neighborhood is a true gem, benefiting from its prime location and excellent schools, in an area experiencing rapid transformation.

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

An unparalleled opportunity to live in one of Orlando’s most desirable areas and in a truly dream-worthy home! This stunning 4-bedroom, 3-bathroom property, situated on a spacious 0.32-acre lot (13,814 square feet), has been completely remodeled with exceptional attention to detail. It boasts a custom Calacatta surface and brand-new stainless steel appliances, including a sleek glass cooktop, all cabinets come with soft-close drawers. The elegant two-tone cabinetry adds a custom touch that will impress your guests. The heart of the home is bathed in natural light thanks to a large front window in the dining area, creating an inviting atmosphere. Sliding glass doors connect the living space to the outdoor oasis, where you’ll find a spacious pool with a screened enclosure, a beautifully landscaped yard, and a cozy fire pit, perfect for relaxing or entertaining from the comfort of your own home. The dining area also features a convenient coffee bar that enhances functionality. Nestled in one of Winter Park’s most sought-after neighborhoods, this property is just minutes away from exclusive dining and boutique shopping. Zoned for top-rated Audubon K-8 and Winter Park High School, this neighborhood is a true gem, benefiting from its prime location and excellent schools, in an area experiencing rapid transformation.

2258 E Howard Drive, 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