Homesinorlando.forsale Search Results

$999,000

Under contract-accepting backup offers. Virtually Staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring, recessed lighting, and all new modern fixtures. The entryway features comfortable seating, built in cabinets with an electric fireplace and wine refrigerator. The sleek, updated kitchen offers a gas range, stylish finishes and a functional layout perfect for everyday living and entertaining. Retreat to the spacious primary bedroom with a fabulous ensuite bath, complete with a soaking tub, dual vanities, a large separate shower, and a generous walk-in closet. A split-bedroom floor plan provides added privacy and comfort. The fully fenced backyard offers plenty of room for a pool and includes private parking for a boat on the side of the home. Whether you enjoy the home as it is or choose to build your dream residence, the possibilities are endless. New roof installed in 2022.

3 Beds ⋅ 2 Baths ⋅ Lake Virginia SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Virtually Staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring, recessed lighting, and all new modern fixtures. The entryway features comfortable seating, built in cabinets with an electric fireplace and wine refrigerator. The sleek, updated kitchen offers a gas range, stylish finishes and a functional layout perfect for everyday living and entertaining. Retreat to the spacious primary bedroom with a fabulous ensuite bath, complete with a soaking tub, dual vanities, a large separate shower, and a generous walk-in closet. A split-bedroom floor plan provides added privacy and comfort. The fully fenced backyard offers plenty of room for a pool and includes private parking for a boat on the side of the home. Whether you enjoy the home as it is or choose to build your dream residence, the possibilities are endless. New roof installed in 2022.

1836 Grinnell Terrace, Winter Park

$470,000

Nice 2BR/1Bath plus office/nursery in the heart of Orwin Manor.

2 Beds ⋅ 1 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Nice 2BR/1Bath plus office/nursery in the heart of Orwin Manor.

1564 Cavendish Road, Winter Park

$1,595,000

Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

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

Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park

$2,750,000

Repositioned at $2,850,000, 151 Oakwood Way is one of the strongest newer luxury opportunities under $3M in Winter Park. Built by LunDev Custom Homes in 2023, this 4,129-square-foot residence sits on a quiet brick street in Charmont and offers a private pool, spa, covered lanai, summer kitchen, automatic screens, and a rare under-$700/sf position for newer luxury construction in 32789. Inside, the home features wide-plank wood flooring, high ceilings, quartz surfaces, Thermador appliances, custom built-ins, a wet bar, walk-in closets, and an open kitchen, dining, and living layout filled with natural light. The main living areas connect directly to the outdoor entertaining space, creating the indoor-outdoor flow buyers want in Winter Park. The floor plan includes 4 bedrooms, 4.5 baths, a main-level primary suite, generous secondary spaces, and a large flex room that can function as an office, family room, media room, game room, or future guest suite, with plumbing already in place. Set on a landscaped 0.26-acre lot with no HOA shown publicly, 151 Oakwood offers a compelling combination in 32789: newer LunDev construction, private pool, outdoor kitchen, brick-street setting, and a sub-$3M position close to Winter Park, Baldwin Park, Audubon Park, and Park Avenue.

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

Repositioned at $2,850,000, 151 Oakwood Way is one of the strongest newer luxury opportunities under $3M in Winter Park. Built by LunDev Custom Homes in 2023, this 4,129-square-foot residence sits on a quiet brick street in Charmont and offers a private pool, spa, covered lanai, summer kitchen, automatic screens, and a rare under-$700/sf position for newer luxury construction in 32789. Inside, the home features wide-plank wood flooring, high ceilings, quartz surfaces, Thermador appliances, custom built-ins, a wet bar, walk-in closets, and an open kitchen, dining, and living layout filled with natural light. The main living areas connect directly to the outdoor entertaining space, creating the indoor-outdoor flow buyers want in Winter Park. The floor plan includes 4 bedrooms, 4.5 baths, a main-level primary suite, generous secondary spaces, and a large flex room that can function as an office, family room, media room, game room, or future guest suite, with plumbing already in place. Set on a landscaped 0.26-acre lot with no HOA shown publicly, 151 Oakwood offers a compelling combination in 32789: newer LunDev construction, private pool, outdoor kitchen, brick-street setting, and a sub-$3M position close to Winter Park, Baldwin Park, Audubon Park, and Park Avenue.

151 Oakwood Way, Winter Park

$620,000

Charming Mid-Century Winter Park bungalow with tremendous potential * Not ready to build a new home but would like to have that option someday? This property provides the unique opportunity of being move-in ready and not overvalued for the neighborhood * The majority of the homes on this quiet tree lined street are brand new or recently built. There is value in being one of the only remaining homesites to be rebuilt * Ready to either owner-occupy or lease ($2,095 per month lease just completed) while you take the appropriate amount of time to create your custom plans. Step inside to find beautiful, exposed hardwood floors with timeless warmth and elegance, while the updated kitchen and baths ensure the home is move-in ready for your convenience. The large, fenced backyard offers plenty of room for outdoor living, providing the perfect spot to relax or entertain * The carport features a laundry/storage area, adding even more functionality to the property * House has a durable metal roof, further enhancing its appeal and longevity. For those looking to create a custom masterpiece, the existing structure offers the option for redevelopment, allowing you to build a home that perfectly suits your vision * Owner painted the exterior, replaced the microwave and hot water heater last year * Located just off N Park Avenue and a short distance from Winter Park's main attractions, you'll enjoy proximity to Downtown Winter Park, Winter Park Farmers Market, Whole Foods, Winter Park Village, and Rollins College. Shopping, dining, and entertainment are all just moments away, making this an unbeatable location * Don’t miss the chance to make this rare find your own! Currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School *

2 Beds ⋅ 2 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Charming Mid-Century Winter Park bungalow with tremendous potential * Not ready to build a new home but would like to have that option someday? This property provides the unique opportunity of being move-in ready and not overvalued for the neighborhood * The majority of the homes on this quiet tree lined street are brand new or recently built. There is value in being one of the only remaining homesites to be rebuilt * Ready to either owner-occupy or lease ($2,095 per month lease just completed) while you take the appropriate amount of time to create your custom plans. Step inside to find beautiful, exposed hardwood floors with timeless warmth and elegance, while the updated kitchen and baths ensure the home is move-in ready for your convenience. The large, fenced backyard offers plenty of room for outdoor living, providing the perfect spot to relax or entertain * The carport features a laundry/storage area, adding even more functionality to the property * House has a durable metal roof, further enhancing its appeal and longevity. For those looking to create a custom masterpiece, the existing structure offers the option for redevelopment, allowing you to build a home that perfectly suits your vision * Owner painted the exterior, replaced the microwave and hot water heater last year * Located just off N Park Avenue and a short distance from Winter Park's main attractions, you'll enjoy proximity to Downtown Winter Park, Winter Park Farmers Market, Whole Foods, Winter Park Village, and Rollins College. Shopping, dining, and entertainment are all just moments away, making this an unbeatable location * Don’t miss the chance to make this rare find your own! Currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School *

1137 Oaks Boulevard, Winter Park

$168,500

Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features laminate flooring throughout, creating a modern and cohesive living space. The unit is ideally located close to shopping, dining, and everyday conveniences, making daily living easy and enjoyable. With lake access just steps away, you can take in the serene waterfront setting while still being minutes from everything Winter Park has to offer. Lawn care is included, ensuring a well-maintained and picturesque community year-round. Don’t miss this opportunity to enjoy lakefront living with resort-style amenities in one of Central Florida’s most desirable areas.

1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features laminate flooring throughout, creating a modern and cohesive living space. The unit is ideally located close to shopping, dining, and everyday conveniences, making daily living easy and enjoyable. With lake access just steps away, you can take in the serene waterfront setting while still being minutes from everything Winter Park has to offer. Lawn care is included, ensuring a well-maintained and picturesque community year-round. Don’t miss this opportunity to enjoy lakefront living with resort-style amenities in one of Central Florida’s most desirable areas.

1500 Gay Road Unit 5, Winter Park

$599,900

TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.

3 Beds ⋅ 2 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.

1951 Staunton Avenue, Winter Park

$610,000

Large double lot in the highly desirable Killarney Shores neighborhood of Winter Park. The property has already received county approval to revert to the original platting, subdivide into two 50' x 135' lots. Located just one block from Lake Killarney. This prime location is minutes from Park Avenue, College Park, and I-4, providing both convenience and long-term value. A rare opportunity to build or invest in one of Winter Park’s most sought-after areas.

32789 Zip Code

Large double lot in the highly desirable Killarney Shores neighborhood of Winter Park. The property has already received county approval to revert to the original platting, subdivide into two 50' x 135' lots. Located just one block from Lake Killarney. This prime location is minutes from Park Avenue, College Park, and I-4, providing both convenience and long-term value. A rare opportunity to build or invest in one of Winter Park’s most sought-after areas.

1860 Staunton Avenue, Winter Park

$2,250,000

Boasting a prestigious Park Avenue address, this striking modern architectural residence perfectly balances bold design with spa-like serenity. Set on a beautifully landscaped corner lot, the home embodies the rare combination of privacy and proximity, just a leisurely 25-minute stroll from Park Avenue’s world-class boutiques and dining. Every element of the design has been meticulously curated to evoke a sense of refined tranquility, where clean lines, natural textures, and warm tones create a timeless yet inviting atmosphere. Inside, expansive open concept living spaces are bathed in natural light, showcasing designer lighting, custom millwork, and seamless indoor-outdoor integration. The chef’s kitchen is a true centerpiece, anchored by dramatic quartz countertops, sleek custom cabinetry, and top-tier stainless steel appliances, complemented by a hidden walk-in pantry that enhances both style and function. The main living area opens effortlessly to the pool creating a fluid connection between indoor elegance and alfresco entertaining. The primary suite is a private retreat defined by calm sophistication offering a spa-inspired bath with a massive walk-in shower featuring multiple shower heads, a freestanding soaking tub, dual vanities, and a custom closet that feels like a boutique dressing room. Upstairs, a loft serves as a serene media or lounge area, while three spacious ensuite bedrooms provide comfort and privacy for family and guests. A dedicated home office continues the home’s minimalist aesthetic, fostering focus in a tranquil setting. Outdoors, the property unfolds into a private resort-like sanctuary with a sparkling pool, lush landscaping, and a fully equipped summer kitchen designed for seamless entertainment. A newly added rooftop deck serves as an architectural statement piece, connected by a spiral staircase that descends to the backyard below. The detached gym offers flexibility as a fitness studio, guest suite, game room, or creative workspace. From its sleek modern lines to its spa-like finishes, this home captures the essence of elevated Winter Park Living. A short walk to Winter Park Village and downtown WP puts you right in the middle of everything.

5 Beds ⋅ 5 Baths ⋅ Twin Acres SubDv. ⋅ 32789 Zip Code

Boasting a prestigious Park Avenue address, this striking modern architectural residence perfectly balances bold design with spa-like serenity. Set on a beautifully landscaped corner lot, the home embodies the rare combination of privacy and proximity, just a leisurely 25-minute stroll from Park Avenue’s world-class boutiques and dining. Every element of the design has been meticulously curated to evoke a sense of refined tranquility, where clean lines, natural textures, and warm tones create a timeless yet inviting atmosphere. Inside, expansive open concept living spaces are bathed in natural light, showcasing designer lighting, custom millwork, and seamless indoor-outdoor integration. The chef’s kitchen is a true centerpiece, anchored by dramatic quartz countertops, sleek custom cabinetry, and top-tier stainless steel appliances, complemented by a hidden walk-in pantry that enhances both style and function. The main living area opens effortlessly to the pool creating a fluid connection between indoor elegance and alfresco entertaining. The primary suite is a private retreat defined by calm sophistication offering a spa-inspired bath with a massive walk-in shower featuring multiple shower heads, a freestanding soaking tub, dual vanities, and a custom closet that feels like a boutique dressing room. Upstairs, a loft serves as a serene media or lounge area, while three spacious ensuite bedrooms provide comfort and privacy for family and guests. A dedicated home office continues the home’s minimalist aesthetic, fostering focus in a tranquil setting. Outdoors, the property unfolds into a private resort-like sanctuary with a sparkling pool, lush landscaping, and a fully equipped summer kitchen designed for seamless entertainment. A newly added rooftop deck serves as an architectural statement piece, connected by a spiral staircase that descends to the backyard below. The detached gym offers flexibility as a fitness studio, guest suite, game room, or creative workspace. From its sleek modern lines to its spa-like finishes, this home captures the essence of elevated Winter Park Living. A short walk to Winter Park Village and downtown WP puts you right in the middle of everything.

2015 N Park Avenue, Winter Park

$1,050,000

Welcome to 831 & 833 Huntington Court, a rarely available duplex tucked away on a quiet cul-de-sac in one of Winter Park’s most walkable and desirable locations. Just minutes from Park Avenue, local lakes, dining, shopping, and entertainment, this property offers the perfect blend of privacy, convenience, and long-term value. Both properties are beautifully landscaped and have pavered driveways offering plenty of parking for the residents and their guests. Each thoughtfully designed unit lives like a single-family home. Both sides feature private, fully fenced yards complete with patios ideal for outdoor dining or relaxing, as well as access to a shared saltwater pool. Additional amenities include two storage sheds, one for pool equipment and another for general storage. Inside, each property welcomes you directly into the living room, which flows naturally into the updated kitchen. In addition to the living room, each unit offers a flexible downstairs room that can be used as a sitting area, separate dining space, home office, or additional living area, allowing the home to adapt to a variety of lifestyles. Each unit offers a functional and inviting layout with one bedroom and full bathroom downstairs, and two bedrooms with a full bathroom upstairs. The downstairs features tile flooring throughout, an updated kitchen with granite countertops, stylish backsplash, stainless steel appliances, under-cabinet lighting, and a breakfast bar with overhang seating. Indoor laundry and ample cabinetry are conveniently located near the kitchen, and generous closet space can be found throughout both homes. Upstairs, you’ll find two comfortable bedrooms with newer carpet and a shared bathroom, creating a private and peaceful retreat. Each unit features a front porch with a portico to the one car garage. Lovingly maintained over the years, this duplex offers exceptional privacy, great walkability, and versatile use. It's ideal as a long-term rental investment, or for an owner-occupant looking to live in one unit while enjoying income from the other. It's truly a special opportunity in the heart of Winter Park.

6 Beds ⋅ 4 Baths ⋅ Huntington Court SubDv. ⋅ 32789 Zip Code

Welcome to 831 & 833 Huntington Court, a rarely available duplex tucked away on a quiet cul-de-sac in one of Winter Park’s most walkable and desirable locations. Just minutes from Park Avenue, local lakes, dining, shopping, and entertainment, this property offers the perfect blend of privacy, convenience, and long-term value. Both properties are beautifully landscaped and have pavered driveways offering plenty of parking for the residents and their guests. Each thoughtfully designed unit lives like a single-family home. Both sides feature private, fully fenced yards complete with patios ideal for outdoor dining or relaxing, as well as access to a shared saltwater pool. Additional amenities include two storage sheds, one for pool equipment and another for general storage. Inside, each property welcomes you directly into the living room, which flows naturally into the updated kitchen. In addition to the living room, each unit offers a flexible downstairs room that can be used as a sitting area, separate dining space, home office, or additional living area, allowing the home to adapt to a variety of lifestyles. Each unit offers a functional and inviting layout with one bedroom and full bathroom downstairs, and two bedrooms with a full bathroom upstairs. The downstairs features tile flooring throughout, an updated kitchen with granite countertops, stylish backsplash, stainless steel appliances, under-cabinet lighting, and a breakfast bar with overhang seating. Indoor laundry and ample cabinetry are conveniently located near the kitchen, and generous closet space can be found throughout both homes. Upstairs, you’ll find two comfortable bedrooms with newer carpet and a shared bathroom, creating a private and peaceful retreat. Each unit features a front porch with a portico to the one car garage. Lovingly maintained over the years, this duplex offers exceptional privacy, great walkability, and versatile use. It's ideal as a long-term rental investment, or for an owner-occupant looking to live in one unit while enjoying income from the other. It's truly a special opportunity in the heart of Winter Park.

831/833 Huntington Court, Winter Park

$1,100,000

Perfectly positioned just one street from iconic Park Avenue, this exceptional Winter Park residence is a masterclass in refined luxury and bespoke design. With unobstructed views often lush landscape and lake views from coveted fourth-floor vantage point, this one-of-a-kind pied-'a-terre has been completely transformed by W DESIGNS LTD. into a sophisticated sanctuary with an old-world Ritz Carlton vibe. Every detail has been curated to the highest standard-from the dramatic CALCUTTA GOLD and Harlequin Marble Flooring to the rich Quartzite surfaces and fully customized solid wood cabinetry throughout. The kitchen and baths are adorned with SOLID BRASS hardware and fixtures, including a custom Phylrich faucet, while both bathrooms are enveloped entirely in Marble, creating a true spa-like experience. GOLD LEAF LIGHTING, Exquisite Millwork, Custom paneling, Crown Molding, Solid Wood Beams, Lacquered Doors, and a flawless LEVEL 5 Finish elevate this home to a level rarely seen. No expense has been spared. Set along the coveted Winter Park Chain of Lakes and just a block away from the boutiques and restaurants of exclusive Park Avenue, is this rare offering for the most discerning buyer seeking timeless elegance, location, and exclusivity. This type of real estate does not come on the market often.

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

Perfectly positioned just one street from iconic Park Avenue, this exceptional Winter Park residence is a masterclass in refined luxury and bespoke design. With unobstructed views often lush landscape and lake views from coveted fourth-floor vantage point, this one-of-a-kind pied-'a-terre has been completely transformed by W DESIGNS LTD. into a sophisticated sanctuary with an old-world Ritz Carlton vibe. Every detail has been curated to the highest standard-from the dramatic CALCUTTA GOLD and Harlequin Marble Flooring to the rich Quartzite surfaces and fully customized solid wood cabinetry throughout. The kitchen and baths are adorned with SOLID BRASS hardware and fixtures, including a custom Phylrich faucet, while both bathrooms are enveloped entirely in Marble, creating a true spa-like experience. GOLD LEAF LIGHTING, Exquisite Millwork, Custom paneling, Crown Molding, Solid Wood Beams, Lacquered Doors, and a flawless LEVEL 5 Finish elevate this home to a level rarely seen. No expense has been spared. Set along the coveted Winter Park Chain of Lakes and just a block away from the boutiques and restaurants of exclusive Park Avenue, is this rare offering for the most discerning buyer seeking timeless elegance, location, and exclusivity. This type of real estate does not come on the market often.

100 S Interlachen Avenue Unit 404, Winter Park

$200,000

VACANT LAND

Karolina On Killarney SubDv. ⋅ 32789 Zip Code

VACANT LAND

1821 Killarney Drive, Winter Park

$237,500

DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has been improved with raised Ceilings and expansive Wood Cabinets, Corian Sink and Countertops, Stainless Steel Appliances and expanded Pass-through Opening/Bar to Dining Room. Spacious Living and Dining Rooms with Lakeview. French Doors to Second Bedroom/Office with closets. Master Bedroom with en-suite Bath. Beautiful Cork Floors installed in all Living Areas. Tile in Kitchen and Baths. Ventless Washer and Dryer installed in Unit. Newer Double-Paned Energy-Efficient Windows. Unit has been replumbed. approximately 5 years ago. A/C and Water Heater new in 2025. Electric Panel replaced in 2019. You will love this close-in Winter Park Lakefront Community with all it's amenities, including Boat Ramp, 12 Boat Slips with Docks available for Lease to Owners, Waterfront Gazebo, Pool and. Clubhouse. Close to Shopping, Restaurants, Movie Theaters, Trader Joe's, Downtown Winter Park and Farmer's Market. Easy Access to I-4. Don't miss another Sunset! Call for a Private showing today!

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

DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has been improved with raised Ceilings and expansive Wood Cabinets, Corian Sink and Countertops, Stainless Steel Appliances and expanded Pass-through Opening/Bar to Dining Room. Spacious Living and Dining Rooms with Lakeview. French Doors to Second Bedroom/Office with closets. Master Bedroom with en-suite Bath. Beautiful Cork Floors installed in all Living Areas. Tile in Kitchen and Baths. Ventless Washer and Dryer installed in Unit. Newer Double-Paned Energy-Efficient Windows. Unit has been replumbed. approximately 5 years ago. A/C and Water Heater new in 2025. Electric Panel replaced in 2019. You will love this close-in Winter Park Lakefront Community with all it's amenities, including Boat Ramp, 12 Boat Slips with Docks available for Lease to Owners, Waterfront Gazebo, Pool and. Clubhouse. Close to Shopping, Restaurants, Movie Theaters, Trader Joe's, Downtown Winter Park and Farmer's Market. Easy Access to I-4. Don't miss another Sunset! Call for a Private showing today!

2500 Lee Road Unit 229, Winter Park

$450,000

This Winter Park property offers exceptional potential in one of the most desirable and rapidly evolving areas of Central Florida. Zoned R-3, this parcel opens the door to redevelopment possibilities for builders, investors, or end users looking to create something special. Ideally located just minutes from Park Avenue and within walking distance to Winter Park Village, you’ll enjoy easy access to premier dining, shopping, entertainment, and lifestyle amenities. The property is also conveniently situated near Orlando Avenue, providing quick connectivity to surrounding areas. The existing structure is being sold as-is, and the true value lies in the land, zoning, and prime location. With ongoing redevelopment nearby and strong demand for new construction, this is an ideal opportunity to build a custom residence or explore allowable uses under current zoning (buyer to verify all development potential with the City of Winter Park). Whether you’re a builder, investor, or buyer with vision, this is your chance to secure a property in a high-demand corridor with long-term upside.Cash buyers and builders welcome. No HOA. City water and sewer. 32789 zip code.

2 Beds ⋅ 1 Baths ⋅ Capens Add SubDv. ⋅ 32789 Zip Code

This Winter Park property offers exceptional potential in one of the most desirable and rapidly evolving areas of Central Florida. Zoned R-3, this parcel opens the door to redevelopment possibilities for builders, investors, or end users looking to create something special. Ideally located just minutes from Park Avenue and within walking distance to Winter Park Village, you’ll enjoy easy access to premier dining, shopping, entertainment, and lifestyle amenities. The property is also conveniently situated near Orlando Avenue, providing quick connectivity to surrounding areas. The existing structure is being sold as-is, and the true value lies in the land, zoning, and prime location. With ongoing redevelopment nearby and strong demand for new construction, this is an ideal opportunity to build a custom residence or explore allowable uses under current zoning (buyer to verify all development potential with the City of Winter Park). Whether you’re a builder, investor, or buyer with vision, this is your chance to secure a property in a high-demand corridor with long-term upside.Cash buyers and builders welcome. No HOA. City water and sewer. 32789 zip code.

841 W Swoope Avenue, Winter Park

$475,000

Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is on the main level for guests. Enjoy community amenities including a swimming pool and a waterfront deck just 30 feet away, ideal for soaking in sunsets and lakeside breezes. All of this in an unbeatable location, just minutes from Winter Park Village, Trader Joe’s, Whole Foods, Park Avenue, dining, and shopping, with easy access to major roads for commuting.

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

Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is on the main level for guests. Enjoy community amenities including a swimming pool and a waterfront deck just 30 feet away, ideal for soaking in sunsets and lakeside breezes. All of this in an unbeatable location, just minutes from Winter Park Village, Trader Joe’s, Whole Foods, Park Avenue, dining, and shopping, with easy access to major roads for commuting.

630 Killarney Bay Court Unit 3, Winter Park

$1,380,000

Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.

4 Beds ⋅ 4 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.

1751 Goodrich Avenue, Winter Park

$315,000

Back on Market — Buyer’s financing fell through. This well-maintained Dubsdread District home is ready for its next owner! Previously under contract within 10 days, the property is back on the market due to a change in the buyer’s ability to secure finances — NO fault of the home. Featuring over 1,500 sq ft on a generous .22-acre lot across from the 5th tee at Dubsdread Golf Course, this updated 4-bedroom residence offers a 2023 rear addition, screened porch, and Florida room, along with major system upgrades including a 2020 roof, 2023 tankless water heater, new windows with transferrable warranty (2023), and updated electrical and plumbing. Move-in ready!! This is a rare opportunity to own a golf-adjacent home in one of Winter Park/College Park's most desirable neighborhoods—don’t miss it! — schedule your showing today. Seller welcomes clean, straightforward offers and is motivated to move efficiently.

4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Back on Market — Buyer’s financing fell through. This well-maintained Dubsdread District home is ready for its next owner! Previously under contract within 10 days, the property is back on the market due to a change in the buyer’s ability to secure finances — NO fault of the home. Featuring over 1,500 sq ft on a generous .22-acre lot across from the 5th tee at Dubsdread Golf Course, this updated 4-bedroom residence offers a 2023 rear addition, screened porch, and Florida room, along with major system upgrades including a 2020 roof, 2023 tankless water heater, new windows with transferrable warranty (2023), and updated electrical and plumbing. Move-in ready!! This is a rare opportunity to own a golf-adjacent home in one of Winter Park/College Park's most desirable neighborhoods—don’t miss it! — schedule your showing today. Seller welcomes clean, straightforward offers and is motivated to move efficiently.

2249 Minnesota Avenue, Winter Park

$669,000

Well-maintained and beautifully upgraded, this exceptional home is located in the highly desirable Dubsdread Heights neighborhood of Winter Park. Offering 4 bedrooms and 2.5 baths (with the 4th bedroom downstairs currently used as an office/den), every detail of this residence has been thoughtfully enhanced. Recent major upgrades include a new roof (2024), new HVAC systems (2024/2025), and upgraded flooring throughout. The gourmet open kitchen features solid cabinetry, a tile backsplash, NEW French Door Refrigerator and an oversized island that flows seamlessly into the inviting family room, highlighted by a stunning gas fireplace. Architectural details abound, including framed windows, 8-foot solid core doors, custom crown molding, and a triple set of French doors that enhance the home’s character and charm. The oversized primary suite is a true retreat, featuring a spa-like bath with an extra-large double vanity, walk-in closet, jetted tub, spacious shower with steamer, and a private covered Juliet balcony. A large downstairs office/study/den with French doors offers flexibility for work or additional living space. The pavered driveway leads to a detached, oversized 2-car garage with air conditioning and an insulated garage door. Outdoors, the backyard is a private oasis with brand-new vinyl fencing and a generous covered patio—perfect for relaxing or entertaining. Ideally located near Dubsdread Golf Course and just minutes from I-4, Winter Park, and College Park shopping, dining, and professional services, this home offers luxury, comfort, and convenience in one exceptional package. Fireplace has never been operated nor is a propane tank on site.

4 Beds ⋅ 3 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Well-maintained and beautifully upgraded, this exceptional home is located in the highly desirable Dubsdread Heights neighborhood of Winter Park. Offering 4 bedrooms and 2.5 baths (with the 4th bedroom downstairs currently used as an office/den), every detail of this residence has been thoughtfully enhanced. Recent major upgrades include a new roof (2024), new HVAC systems (2024/2025), and upgraded flooring throughout. The gourmet open kitchen features solid cabinetry, a tile backsplash, NEW French Door Refrigerator and an oversized island that flows seamlessly into the inviting family room, highlighted by a stunning gas fireplace. Architectural details abound, including framed windows, 8-foot solid core doors, custom crown molding, and a triple set of French doors that enhance the home’s character and charm. The oversized primary suite is a true retreat, featuring a spa-like bath with an extra-large double vanity, walk-in closet, jetted tub, spacious shower with steamer, and a private covered Juliet balcony. A large downstairs office/study/den with French doors offers flexibility for work or additional living space. The pavered driveway leads to a detached, oversized 2-car garage with air conditioning and an insulated garage door. Outdoors, the backyard is a private oasis with brand-new vinyl fencing and a generous covered patio—perfect for relaxing or entertaining. Ideally located near Dubsdread Golf Course and just minutes from I-4, Winter Park, and College Park shopping, dining, and professional services, this home offers luxury, comfort, and convenience in one exceptional package. Fireplace has never been operated nor is a propane tank on site.

681 Overspin Drive, Winter Park

$585,000

This move-in-ready condominium checks nearly every box for today’s buyer, offering a lock-and-leave lifestyle in an exceptional Winter Park location. The completely renovated two-bedroom, two-bath residence features high-quality finishes and thoughtful details throughout, including wide-plank white oak flooring and a bright, open-concept living space designed for everyday comfort and entertaining. The chef’s kitchen is stylish and functional, showcasing honed quartzite countertops, custom cabinetry extending to the ceiling, GE Café appliances with hood vent, and a handcrafted Moroccan Zellige tile backsplash. Both the primary suite and guest suite include custom built-in closets and private en-suite baths. Each bath has been fully updated with new vanities, designer tile, glass-enclosed showers and curated fixtures. A screened patio provides an inviting outdoor retreat, overlooking mature oak trees and lush landscaping. The first-floor location allows for easy access to assigned covered parking and an exterior storage unit just near the front door. Recent updates include a new roof (2024), new HVAC system (2023), new water heater (2023), rewired electrical and refreshed exterior paint (2018). An extraordinary setting places this residence just a short distance from Park Avenue and Central Park, the heart of downtown Winter Park. Enjoy a walkable lifestyle where mornings can begin with coffee at a local café, evenings are filled with dining, live music and community gatherings, and weekends are spent strolling the beloved Saturday Farmers’ Market. Central Park is home to cherished traditions including the Winter Park Sidewalk Art Festival, outdoor concerts, movies on the lawn and various holiday parades along Park Avenue, bringing energy and charm to the area throughout the year. Adding to the appeal, the home is also moments from the historic Winter Park 9 Golf Course, established in 1914 and recognized as one of the oldest municipal golf courses in Florida. Whether enjoying a round of golf, an evening walk, or simply taking in the surroundings, this location offers a rare blend of leisure, culture and convenience in one of Central Florida’s sought-after downtown environments.

2 Beds ⋅ 2 Baths ⋅ Andalucia Apts SubDv. ⋅ 32789 Zip Code

This move-in-ready condominium checks nearly every box for today’s buyer, offering a lock-and-leave lifestyle in an exceptional Winter Park location. The completely renovated two-bedroom, two-bath residence features high-quality finishes and thoughtful details throughout, including wide-plank white oak flooring and a bright, open-concept living space designed for everyday comfort and entertaining. The chef’s kitchen is stylish and functional, showcasing honed quartzite countertops, custom cabinetry extending to the ceiling, GE Café appliances with hood vent, and a handcrafted Moroccan Zellige tile backsplash. Both the primary suite and guest suite include custom built-in closets and private en-suite baths. Each bath has been fully updated with new vanities, designer tile, glass-enclosed showers and curated fixtures. A screened patio provides an inviting outdoor retreat, overlooking mature oak trees and lush landscaping. The first-floor location allows for easy access to assigned covered parking and an exterior storage unit just near the front door. Recent updates include a new roof (2024), new HVAC system (2023), new water heater (2023), rewired electrical and refreshed exterior paint (2018). An extraordinary setting places this residence just a short distance from Park Avenue and Central Park, the heart of downtown Winter Park. Enjoy a walkable lifestyle where mornings can begin with coffee at a local café, evenings are filled with dining, live music and community gatherings, and weekends are spent strolling the beloved Saturday Farmers’ Market. Central Park is home to cherished traditions including the Winter Park Sidewalk Art Festival, outdoor concerts, movies on the lawn and various holiday parades along Park Avenue, bringing energy and charm to the area throughout the year. Adding to the appeal, the home is also moments from the historic Winter Park 9 Golf Course, established in 1914 and recognized as one of the oldest municipal golf courses in Florida. Whether enjoying a round of golf, an evening walk, or simply taking in the surroundings, this location offers a rare blend of leisure, culture and convenience in one of Central Florida’s sought-after downtown environments.

535 N Interlachen Avenue Unit 106, Winter Park

$154,000

Stunning 1 bedroom 1 bathroom GROUND FLOOR condo in sought after Lakeside Manor. The spacious and open floor plan has been completely updated and features luxury vinyl floors in main living areas and updated tile in kitchen and bathroom. The kitchen features newer wood cabinets, stone counters and stainless steel appliances and a gorgeous designer backsplash. The condo windows have been updated and also feature custom shutters for a designer touch and privacy. Lakeside Manor is a Lakefront community that offers private access to Lake Killarney a 239 acre spring fed lake, private boat ramp, residents will enjoy access to boat slips (based on availability, charge is $35/month), community pool, guest parking, extra parking $35 if available, community laundry room, outdoor grill and picnic tables. Lakeside Manor is located minutes from Winter Park Village, shopping, dinning and has easy access to Rollings College, UCF, Valencia Downtown Campus, I-4 and Downtown Orlando and Park Ave shopping district.

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

Stunning 1 bedroom 1 bathroom GROUND FLOOR condo in sought after Lakeside Manor. The spacious and open floor plan has been completely updated and features luxury vinyl floors in main living areas and updated tile in kitchen and bathroom. The kitchen features newer wood cabinets, stone counters and stainless steel appliances and a gorgeous designer backsplash. The condo windows have been updated and also feature custom shutters for a designer touch and privacy. Lakeside Manor is a Lakefront community that offers private access to Lake Killarney a 239 acre spring fed lake, private boat ramp, residents will enjoy access to boat slips (based on availability, charge is $35/month), community pool, guest parking, extra parking $35 if available, community laundry room, outdoor grill and picnic tables. Lakeside Manor is located minutes from Winter Park Village, shopping, dinning and has easy access to Rollings College, UCF, Valencia Downtown Campus, I-4 and Downtown Orlando and Park Ave shopping district.

2500 Lee Road Unit 110, Winter Park

$13,000,000

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

6 Beds ⋅ 9 Baths ⋅ --- SubDv. ⋅ 32789 Zip Code

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

2203 Via Tuscany, Winter Park

$640,000

This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a dedicated study. A large screened-in front porch adds to the home’s classic charm and provides the perfect space to relax and unwind. Tucked away in the rear of the property there is both flexibility and income potential: a stylish studio office and a spacious one-bedroom unit complete with its own living area and separate loft. This property is ideal for investors, multi-generational living, or owner-occupants seeking strong rental returns. Located closely to beautiful Lake Killarney and conveniently situated near highways, restaurants, and shopping, this property combines charm, location, and income potential in one exceptional offering.

5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a dedicated study. A large screened-in front porch adds to the home’s classic charm and provides the perfect space to relax and unwind. Tucked away in the rear of the property there is both flexibility and income potential: a stylish studio office and a spacious one-bedroom unit complete with its own living area and separate loft. This property is ideal for investors, multi-generational living, or owner-occupants seeking strong rental returns. Located closely to beautiful Lake Killarney and conveniently situated near highways, restaurants, and shopping, this property combines charm, location, and income potential in one exceptional offering.

352 Cambridge Boulevard, Winter Park

$1,650,000

PRICE IMPROVEMENT! This exceptional custom residence, built by Meridian Homes and designed by Zero Latitude, offers a rare combination of thoughtful architecture, high-end finishes, and modern functionality. Interior design by Lauren Ayers Interiors sets a refined tone throughout, complemented by curated details such as Rifle Paper wallpaper, accent walls, and wide-plank hardwood flooring by Britannia Flooring. The home features five bedrooms, five full baths, and two half baths, including a first-floor primary suite with a spacious walk-in closet and a spa-inspired bathroom showcasing upgraded imported tile and a large walk-in shower. The main level also includes a powder room, laundry room, a private home office with doors, and a guest suite—ideal for multigenerational living or overnight guests. At the center of the home is a chef’s kitchen with an abundance of custom white cabinetry by Monarch Kitchens and Bath, paired with a striking oversized blue island with seating for four plus additional space for a dining table. Premium appliances include a Wolf oven, GE Café double oven/microwave, refrigerator, and beverage fridge, along with a Thermador dishwasher. The kitchen flows seamlessly into the family room, which features an electric fireplace and custom built-ins, creating an inviting space for everyday living and entertaining. Upstairs, three additional bedrooms each offer private baths featuring custom cabinetry, fixtures, and tile, along with generous closet space, plus a versatile bonus area-ideal as a second family room or media space. Outdoor living is equally impressive. A covered rear lanai overlooks a heated saltwater pool and hot tub, complemented by a summer kitchen with a high-end built-in, vented gas grill, sink, and under-counter refrigerator. An outdoor shower and pool-half-bath complete this resort-style setting. Additional highlights include: floor-to-ceiling imported tile in every bathroom, Custom wrought iron stair railings, Custom wood plantation shutters on all windows, an Automatic driveway gate, a Built-in surround sound system, and a “Control4” whole-house smart system with integrated security, as well as a 2-car garage. This meticulously designed home delivers uncompromising quality, comfort, and convenience in a warm, quiet setting, making it ideal for both everyday living and entertaining. Ideally located in the heart of Winter Park, close to the area's top-rated schools, parks, the YMCA, the boutiques and restaurants on Park Ave, and also minutes from Rollins College and downtown Orlando. Do not miss this opportunity to live in this sophisticated, luxurious home. Schedule your private appointment today.

5 Beds ⋅ 7 Baths ⋅ Orange Grove Sub SubDv. ⋅ 32789 Zip Code

PRICE IMPROVEMENT! This exceptional custom residence, built by Meridian Homes and designed by Zero Latitude, offers a rare combination of thoughtful architecture, high-end finishes, and modern functionality. Interior design by Lauren Ayers Interiors sets a refined tone throughout, complemented by curated details such as Rifle Paper wallpaper, accent walls, and wide-plank hardwood flooring by Britannia Flooring. The home features five bedrooms, five full baths, and two half baths, including a first-floor primary suite with a spacious walk-in closet and a spa-inspired bathroom showcasing upgraded imported tile and a large walk-in shower. The main level also includes a powder room, laundry room, a private home office with doors, and a guest suite—ideal for multigenerational living or overnight guests. At the center of the home is a chef’s kitchen with an abundance of custom white cabinetry by Monarch Kitchens and Bath, paired with a striking oversized blue island with seating for four plus additional space for a dining table. Premium appliances include a Wolf oven, GE Café double oven/microwave, refrigerator, and beverage fridge, along with a Thermador dishwasher. The kitchen flows seamlessly into the family room, which features an electric fireplace and custom built-ins, creating an inviting space for everyday living and entertaining. Upstairs, three additional bedrooms each offer private baths featuring custom cabinetry, fixtures, and tile, along with generous closet space, plus a versatile bonus area-ideal as a second family room or media space. Outdoor living is equally impressive. A covered rear lanai overlooks a heated saltwater pool and hot tub, complemented by a summer kitchen with a high-end built-in, vented gas grill, sink, and under-counter refrigerator. An outdoor shower and pool-half-bath complete this resort-style setting. Additional highlights include: floor-to-ceiling imported tile in every bathroom, Custom wrought iron stair railings, Custom wood plantation shutters on all windows, an Automatic driveway gate, a Built-in surround sound system, and a “Control4” whole-house smart system with integrated security, as well as a 2-car garage. This meticulously designed home delivers uncompromising quality, comfort, and convenience in a warm, quiet setting, making it ideal for both everyday living and entertaining. Ideally located in the heart of Winter Park, close to the area's top-rated schools, parks, the YMCA, the boutiques and restaurants on Park Ave, and also minutes from Rollins College and downtown Orlando. Do not miss this opportunity to live in this sophisticated, luxurious home. Schedule your private appointment today.

1861 Taylor Avenue, Winter Park

$237,500

Attention lake enthusiasts! This is your opportunity to enjoy true waterfront living without the cost or maintenance typically associated with it. Located on beautiful Lake Killarney in sought-after Winter Park you will enjoy an array of amenities including a private boat ramp, a large open boat dock where you can feed the fish and turtles, picnic areas, clubhouse and resort style community pool overlooking the water. This rare 2-bedroom, 2-bath residence offers stunning lake views from the living room, bedroom, and private balcony, creating a peaceful retreat you’ll love coming home to. The home features thoughtful upgrades throughout, including a beautifully updated kitchen with upgraded appliances, induction range with air fryer, soft-close cabinetry and drawers, and a large pantry closet. Crown molding and recessed lighting enhance the space and highlight the luxury vinyl plank flooring throughout. Additional improvements include a new A/C system and tankless water heater, helping to keep the home energy efficient. The community also offers two on-site laundry facilities with private storage units for added convenience. Perfectly situated in highly desirable Winter Park, you’re just minutes from shopping, dining, and everyday essentials. This quiet lakeside community is only steps away from your favorite coffee shop or a casual evening drink. Wake up to lake views, unwind on your private balcony, and enjoy the relaxed Winter Park lifestyle you’ve been dreaming of. Opportunities like this are rare—schedule your private showing today and experience Lake Killarney living for yourself.

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

Attention lake enthusiasts! This is your opportunity to enjoy true waterfront living without the cost or maintenance typically associated with it. Located on beautiful Lake Killarney in sought-after Winter Park you will enjoy an array of amenities including a private boat ramp, a large open boat dock where you can feed the fish and turtles, picnic areas, clubhouse and resort style community pool overlooking the water. This rare 2-bedroom, 2-bath residence offers stunning lake views from the living room, bedroom, and private balcony, creating a peaceful retreat you’ll love coming home to. The home features thoughtful upgrades throughout, including a beautifully updated kitchen with upgraded appliances, induction range with air fryer, soft-close cabinetry and drawers, and a large pantry closet. Crown molding and recessed lighting enhance the space and highlight the luxury vinyl plank flooring throughout. Additional improvements include a new A/C system and tankless water heater, helping to keep the home energy efficient. The community also offers two on-site laundry facilities with private storage units for added convenience. Perfectly situated in highly desirable Winter Park, you’re just minutes from shopping, dining, and everyday essentials. This quiet lakeside community is only steps away from your favorite coffee shop or a casual evening drink. Wake up to lake views, unwind on your private balcony, and enjoy the relaxed Winter Park lifestyle you’ve been dreaming of. Opportunities like this are rare—schedule your private showing today and experience Lake Killarney living for yourself.

2500 Lee Road Unit 228, Winter Park

$1,840,000

Motivated Sellers! Priced at $35,000 below recent Appraisal Price on this amazing oversized lot! Walk into this home with equity from the start! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native landscaping that's creates a private and serene retreat where peacocks often roam freely through your yard. The heart of the home is the beautifully designed chef’s kitchen, featuring quartz countertops, a gas range with custom hood, double built-in convection ovens, stainless steel appliances, a wine refrigerator, and a well-appointed butler’s pantry—perfect for entertaining. The light-filled family room is open to the kitchen and showcases a wood-burning fireplace, custom built-ins, and an original brick accent wall that adds warmth and architectural charm. Engineered hardwood flooring and preserved original terrazzo floors run throughout the home, enhancing its quality designer choices but also an inviting feel. The flexible floor plan offers five spacious bedrooms, three full bathrooms, and two half baths, providing ample space for both everyday living and hosting guests. Expect to be impressed by the elegant owner's suite with a sizable walk-in closet and stunning ensuite bathroom featuring dual vanities, beautiful cabinetry with lots of storage and a generously sized soaking tub. Outdoor living is equally impressive, with a resort-style heated pool complete with a sun shelf, an outdoor kitchen with a built-in grill, sand volleyball court and a large deck featuring built-in seating and a fire pit—ideal for gatherings or relaxing evenings under the stars. Zoned for Winter Park’s top-rated schools, this exceptional home is just a five-minute drive to Park Avenue’s renowned shopping and dining, and walking distance to Baldwin Park’s vibrant downtown, offering shops, restaurants, and a Publix. This is a rare opportunity to own a thoughtfully renovated home in one of Winter Park’s most beautiful and sought-after settings. Experience the rare combination of European-inspired luxury, resort-style outdoor living, and an unparalleled Winter Park location. Be sure to watch the video tour and virtual property walkthrough in the attachments. Better yet, schedule a private showing today and discover a home that truly defines elevated Florida living.

5 Beds ⋅ 5 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Motivated Sellers! Priced at $35,000 below recent Appraisal Price on this amazing oversized lot! Walk into this home with equity from the start! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native landscaping that's creates a private and serene retreat where peacocks often roam freely through your yard. The heart of the home is the beautifully designed chef’s kitchen, featuring quartz countertops, a gas range with custom hood, double built-in convection ovens, stainless steel appliances, a wine refrigerator, and a well-appointed butler’s pantry—perfect for entertaining. The light-filled family room is open to the kitchen and showcases a wood-burning fireplace, custom built-ins, and an original brick accent wall that adds warmth and architectural charm. Engineered hardwood flooring and preserved original terrazzo floors run throughout the home, enhancing its quality designer choices but also an inviting feel. The flexible floor plan offers five spacious bedrooms, three full bathrooms, and two half baths, providing ample space for both everyday living and hosting guests. Expect to be impressed by the elegant owner's suite with a sizable walk-in closet and stunning ensuite bathroom featuring dual vanities, beautiful cabinetry with lots of storage and a generously sized soaking tub. Outdoor living is equally impressive, with a resort-style heated pool complete with a sun shelf, an outdoor kitchen with a built-in grill, sand volleyball court and a large deck featuring built-in seating and a fire pit—ideal for gatherings or relaxing evenings under the stars. Zoned for Winter Park’s top-rated schools, this exceptional home is just a five-minute drive to Park Avenue’s renowned shopping and dining, and walking distance to Baldwin Park’s vibrant downtown, offering shops, restaurants, and a Publix. This is a rare opportunity to own a thoughtfully renovated home in one of Winter Park’s most beautiful and sought-after settings. Experience the rare combination of European-inspired luxury, resort-style outdoor living, and an unparalleled Winter Park location. Be sure to watch the video tour and virtual property walkthrough in the attachments. Better yet, schedule a private showing today and discover a home that truly defines elevated Florida living.

640 Arjay Way, Winter Park

$125,000

Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaurants, schools and major roadways. This end unit features a nice open floorplan with lots of natural light. The kitchen is spacious and has lots of cabinet storage and countertop space it overlooks the large living room with sliding glass doors that lead out to the balcony with a treetop view. The primary bedroom is a nice size and has an en-suite bathroom along with a large closet. The other two bedrooms are good sized and share a hallway bathroom. The HOA fee includes CABLE & INTERNET!!! Do not miss your opportunity to own this unit today.

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove/Winter Park SubDv. ⋅ 32789 Zip Code

Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaurants, schools and major roadways. This end unit features a nice open floorplan with lots of natural light. The kitchen is spacious and has lots of cabinet storage and countertop space it overlooks the large living room with sliding glass doors that lead out to the balcony with a treetop view. The primary bedroom is a nice size and has an en-suite bathroom along with a large closet. The other two bedrooms are good sized and share a hallway bathroom. The HOA fee includes CABLE & INTERNET!!! Do not miss your opportunity to own this unit today.

1695 Lee Road Unit B216, Winter Park

$1,750,000

Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops, custom cabinetry, and stainless steel appliances, perfect for both everyday living and entertaining. Step outside to the private lanai, where you can enjoy a summer kitchen, pool, and lushly landscaped backyard, creating an ideal indoor-outdoor lifestyle. From the moment you enter, the home is filled with warm natural light and high-quality finishes throughout, creating a welcoming atmosphere. The primary bedroom is conveniently located on the first floor, offering privacy and comfort along with an inviting, functional layout. The second floor features three additional bedrooms, two bathrooms, and two expansive terraces, perfect for relaxation or entertaining. Located just minutes ( 1.25 Miles ) from Park Avenue Restaurants and shopping district, 15 min from Downtown Orlando, and an array of fine dining, boutique shopping, museums, and local cafés, this exceptional home offers modern luxury in an unbeatable location.

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

Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops, custom cabinetry, and stainless steel appliances, perfect for both everyday living and entertaining. Step outside to the private lanai, where you can enjoy a summer kitchen, pool, and lushly landscaped backyard, creating an ideal indoor-outdoor lifestyle. From the moment you enter, the home is filled with warm natural light and high-quality finishes throughout, creating a welcoming atmosphere. The primary bedroom is conveniently located on the first floor, offering privacy and comfort along with an inviting, functional layout. The second floor features three additional bedrooms, two bathrooms, and two expansive terraces, perfect for relaxation or entertaining. Located just minutes ( 1.25 Miles ) from Park Avenue Restaurants and shopping district, 15 min from Downtown Orlando, and an array of fine dining, boutique shopping, museums, and local cafés, this exceptional home offers modern luxury in an unbeatable location.

1840 Anzle Avenue, Winter Park

$630,000

This lovely updated mid-century modern home is waiting for you to make it your own! The home is located on a large corner lot, boasts three bedrooms two baths, has hand scraped wood laminate floors throughout, with an open spacious living area separated by a small step down that can accommodate your family room or den, the master bedroom en-suite features a modern glass barn door that opens up to your bath complete with marble floors and custom glass shower enclosure. All new appliances in the kitchen, separate laundry room with storage. It has a large fenced in yard to make your own, for entertaining and relaxing! Zoned for Winter Park's A-rated schools including Audubon K-8, and Winter Park High School. It is located directly behind East End Market in Winter Park, with easy access to walk the eclectic Corrine Dr. and discover quaint shops, eateries and coffee houses. Conveniently located a short drive to Baldwin Park, Park Ave, Mills 50, downtown Orlando and a stone's throw from East End Market, this location can't be beat! Roof, Ac/Ductwork, Windows and Plumbing, are all approximately 10 years old. Buyers should verify room sizes.

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

This lovely updated mid-century modern home is waiting for you to make it your own! The home is located on a large corner lot, boasts three bedrooms two baths, has hand scraped wood laminate floors throughout, with an open spacious living area separated by a small step down that can accommodate your family room or den, the master bedroom en-suite features a modern glass barn door that opens up to your bath complete with marble floors and custom glass shower enclosure. All new appliances in the kitchen, separate laundry room with storage. It has a large fenced in yard to make your own, for entertaining and relaxing! Zoned for Winter Park's A-rated schools including Audubon K-8, and Winter Park High School. It is located directly behind East End Market in Winter Park, with easy access to walk the eclectic Corrine Dr. and discover quaint shops, eateries and coffee houses. Conveniently located a short drive to Baldwin Park, Park Ave, Mills 50, downtown Orlando and a stone's throw from East End Market, this location can't be beat! Roof, Ac/Ductwork, Windows and Plumbing, are all approximately 10 years old. Buyers should verify room sizes.

2805 Northwood Boulevard, Winter Park

$955,000

Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins College and zoned for AudubonK-8! This spacious 2,824 SF home features two primary suites—one on each level—ideal for guests or multi-gen living. Gorgeous hardwood liketile floors throughout, high ceilings, crown molding, and two fireplaces add timeless elegance. The chef’s kitchen includes cherry cabinetry, solid-surface counters, stainless steel appliances, and gas range. Upstairs bonus room is perfect for office or den. There are so many recent updatesincluded, but not limited to: roof (2022), water heater (2023), and HVAC (2021) Enjoy the outdoors from the covered deck, or private balcony.Low-maintenance yard with irrigation 1-car garage, upstairs laundry, and and optional HOA that includes access to private Lake Virginia park.Don’t miss this move-in-ready gem in the heart of Winter Park!

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

Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins College and zoned for AudubonK-8! This spacious 2,824 SF home features two primary suites—one on each level—ideal for guests or multi-gen living. Gorgeous hardwood liketile floors throughout, high ceilings, crown molding, and two fireplaces add timeless elegance. The chef’s kitchen includes cherry cabinetry, solid-surface counters, stainless steel appliances, and gas range. Upstairs bonus room is perfect for office or den. There are so many recent updatesincluded, but not limited to: roof (2022), water heater (2023), and HVAC (2021) Enjoy the outdoors from the covered deck, or private balcony.Low-maintenance yard with irrigation 1-car garage, upstairs laundry, and and optional HOA that includes access to private Lake Virginia park.Don’t miss this move-in-ready gem in the heart of Winter Park!

512 Clarendon Avenue, Winter Park

$190,000

This ground-floor condo offers a practical layout with comfortable living spaces and easy accessibility. The unit provides a blank canvas for buyers looking to personalize their home or investment. Enjoy the convenience of being just minutes from Park Avenue, Rollins College, dining, shopping making commuting and everyday errands effortless. The community offers a low-maintenance lifestyle, ideal for first-time buyers, seasonal residents, or investors. Whether you’re looking to settle into Winter Park or add to your portfolio, this condo presents a great opportunity to own in one of Central Florida’s most desirable areas.

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

This ground-floor condo offers a practical layout with comfortable living spaces and easy accessibility. The unit provides a blank canvas for buyers looking to personalize their home or investment. Enjoy the convenience of being just minutes from Park Avenue, Rollins College, dining, shopping making commuting and everyday errands effortless. The community offers a low-maintenance lifestyle, ideal for first-time buyers, seasonal residents, or investors. Whether you’re looking to settle into Winter Park or add to your portfolio, this condo presents a great opportunity to own in one of Central Florida’s most desirable areas.

1250 S Denning Drive Unit 104, Winter Park