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$1,749,000
5 Beds ⋅ 4 Baths ⋅ Sharon Place SubDv. ⋅ 32789 Zip Code
Tucked away near the end of a peaceful cul-de-sac, 1225 Sharon Place offers space, privacy, and a location that's hard to beat, just two blocks from the Winter Park Racquet Club. This single-story home sits on nearly 16,000 square feet of land and has 5 bedrooms, 3 full bathrooms, and a half bath. The split floor plan puts the primary suite on its own side of the house, away from the other bedrooms, so everyone gets more privacy. Two-zone air conditioning keeps each area comfortable and helps with efficiency. The large covered patio overlooks the screened pool enclosure. It's a natural place to dine outdoors, host friends, or relax in the shade year-round. A two-car garage adds storage and convenience. The same owners have loved this home for 30 years, and it's the first time it's been on the market in decades. Homes this close to the Racquet Club with this much land don't come up often. Schedule your showing today.

1225 Sharon Place, Winter Park

$479,900
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Don’t miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, conveniently located just minutes from AdventHealth, Park Avenue, Downtown Orlando, and I-4. This spacious two-story home features a flexible layout with a two-car garage, remodeled bathrooms, and plenty of living space. The first floor offers a large bedroom, a beautifully remodeled full bathroom, a laundry area and access to the enclosed/screened patio and backyard. Upstairs, you’ll find an open kitchen with stainless steel appliances, a dining area, and a spacious living room. The second floor also features two bedrooms, including the primary bedroom with a remodeled bathroom. Wood flooring and carpet are featured throughout the home. Additional improvements include a roof approximately 5 years old, completely refreshed landscaping and outside power washed. Sliding doors off the kitchen and dining area lead to a new outdoor deck, creating an ideal space for outdoor dining, entertaining, and enjoying the Florida lifestyle. The convenient location provides easy access to major roads, shopping, dining, entertainment, and all that Winter Park and Downtown Orlando have to offer. This home offers a great combination of location, space, and recent updates. Schedule your showing today!

1660 Orange Avenue, Winter Park

$780,000
5 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Set on a quarter-acre lot on a tree-lined street in Winter Park Pines, this 5-bedroom, 3-bath pool home offers 2,194 sq ft of single-story living with room for everyone. The split floor plan places a spacious primary suite on its own side of the home, with a walk-in closet and French doors that open directly to the covered patio. The four guest bedrooms are generously sized, and one pair shares a Jack-and-Jill bath. The kitchen has a breakfast bar, a pantry, and views of the pool. It opens to a family room anchored by a wood-burning fireplace and a built-in desk. The formal living and dining rooms, crown molding, and three sets of French doors bring in natural light and a connection to the outdoors. Outside, the large covered, insulated patio overlooks a sparkling pool and a fenced backyard with real yard space. There is no mandatory HOA, and the oversized 2-car garage includes workshop space. You're minutes from Winter Park Pines Golf Club, Aloma Ave shopping, and Park Avenue. Zoned for Winter Park High.

739 Roughbeard Road, Winter Park

$429,900
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates Sec 5 SubDv. ⋅ 32792 Zip Code
Welcome home to this charming Winter Park residence located in the desirable 32792 zip code. Nestled on a quiet street at 2818 Ambergate Road, this inviting property offers the perfect blend of comfort, style, and everyday convenience. Step inside to discover a bright, open floor plan featuring original Terrazzo, generous living spaces, natural light, and a warm atmosphere ideal for both relaxing and entertaining. Newer roof 2023. The private backyard provides a wonderful outdoor oasis for weekend gatherings or peaceful morning coffee. Situated just minutes from top-rated schools, local parks, bustling shopping centers, and vibrant downtown Winter Park, this move-in-ready home puts the best of Central Florida right at your doorstep. Don't miss this exceptional opportunity - Schedule your private showing today!

2818 Ambergate Road, Winter Park

$585,000
4 Beds ⋅ 3 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code
Welcome home 8113 Lazy Bear Lane! This beautifully maintained 4-bedroom, 2.5-bathroom home in the gated Enclave at Aloma community, where newer construction, thoughtful upgrades, and an unbeatable Winter Park-area location come together. Newer, energy-efficient homes in this area are hard to find—and this one checks all the boxes! Inside, you’ll find a spacious, move-in-ready floor plan featuring newer luxury vinyl flooring, a neutral interior, a dedicated home office/playroom, and an additional bonus room offering flexible space for work, hobbies, guests, or recreation. The upgraded kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, granite countertops, a center island, and an upgraded stainless steel appliance package. Upstairs, the generously sized primary suite offers a private retreat with a large walk-in closet complete with a custom California Closet system. The primary bathroom features dual vanities with his-and-her sinks and a large walk-in shower. The thoughtfully designed second-floor layout centers around a large bonus room, with three additional bedrooms, a secondary bathroom, and a convenient laundry room arranged around this versatile space—creating a functional and flexible living area for the whole household. Step outside to enjoy the large screened-in back porch overlooking a fenced yard with lush landscaping—perfect for relaxing, entertaining, or enjoying Florida’s year-round outdoor lifestyle. A newer shed provides valuable additional storage. Tucked away off Bear Gully Road, Enclave at Aloma is a gated community of just 127 homes, offering a peaceful neighborhood setting while keeping you close to everything. Enjoy convenient proximity to Trinity Preparatory School, Oviedo on the Park, Red Bug Lake Park, Rollins College, downtown Winter Park, and UCF. Easy access to SR 417 makes commuting to downtown Orlando, the area’s international airports, and Central Florida’s world-famous theme parks a breeze. With its desirable location, flexible living spaces, modern upgrades, energy-efficient newer construction, and beautifully landscaped outdoor space, this Winter Park-area home is an opportunity you won’t want to miss!

8113 Lazy Bear Lane, Winter Park

$2,089,000
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concepts, this Louisiana-inspired 4-bedroom, 4-bath home pairs classic double-gallery porches with 3,479 sq ft of open, light-filled living in Winter Park's established Charmont neighborhood. Inside, rich hardwood floors, tray ceilings, crown molding and walls of French doors set the tone. The formal living and dining rooms open to a spacious great room and a chef's kitchen with an oversized granite island seating six, statement pendant lighting, stainless steel appliances, double wall ovens, abundant cabinetry, a walk-in pantry and a separate coffee/beverage bar with wine fridge. The main-level primary suite is a true retreat with a tray ceiling, French doors to the covered lanai, a custom walk-in closet and a spa bath with a freestanding soaking tub, dual vanities and a frameless glass shower. Upstairs, a large loft offers flexible space for a media room, gym or home office, with French doors to the second-story porch, along with generously sized secondary bedrooms. Step outside to your private backyard oasis: a covered lanai with outdoor kitchen, bar seating and ceiling fans overlooks the paver pool deck, sparkling pool with raised spa and fire bowls, all framed by mature landscaping and privacy fencing. Additional highlights include a laundry room with sink and cabinetry, a two-car garage and a paver driveway. Just half a mile from Audubon Park K-8, with Lake Baldwin Park, Mead Botanical Garden, East End Market, Baldwin Park Village and downtown Winter Park's shops and restaurants all close by, and about 4 miles to downtown Orlando.

1951 Winter Park Road, Winter Park

$1,890,000
4 Beds ⋅ 4 Baths ⋅ Parklando 03 SubDv. ⋅ 32789 Zip Code
PRICED BELOW APPRAISED VALUE | FULLY REMODELED WINTER PARK POOL HOME Pre-approval or proof of funds required in advance of showing. A rare opportunity to own more than 3,300 square feet of fully remodeled living space in Winter Park’s 32789 zip code, zoned for the highly sought-after Audubon Park School K–8 and Winter Park High School; all at a price below appraised value. Welcome to 2614 Parkland Drive, a completely reimagined luxury residence where sophisticated interiors meet resort-style Florida living. Extensively remodeled in late 2022 and topped with a brand-new architectural barrel tile roof, this home combines timeless character with modern finishes and major system upgrades. Inside, solid light-oak flooring, custom railings, and an open-concept layout create a warm, elevated feel throughout. The chef’s kitchen anchors the main living space with quartz countertops, full-height designer tile, abundant cabinetry, and a layout designed equally well for entertaining and everyday living. Step outside and the home transforms into a private resort. The custom heated pool and spa are finished in striking Caribbean-blue tile and surrounded by dramatic waterfalls, dual natural-gas fire features, porcelain privacy walls, and a built-in grill—creating an exceptional setting for entertaining or unwinding at home. The first-floor primary suite opens directly to the outdoor oasis. Upstairs, three oversized bedrooms are joined by a spacious loft and private patio; offering flexible space for family, guests, an office, or additional entertaining. Additional features include a brand-new barrel tile roof, dual tankless water heaters, central vacuum, natural-gas appliances, and extensive updates throughout. With more than 3,300 SF, a luxury pool and spa, extensive renovations, highly desirable school zoning, and a 32789 address, this home represents an exceptional opportunity in the Winter Park market. Luxury. Location. Lifestyle. And priced below appraised value.

2614 Parkland Drive, Winter Park

$227,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Villas Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. Beautiful Winter Park Condo with Vaulted Ceilings & Private Fenced Patio! Come home to this beautiful and spacious condo featuring vaulted ceilings, abundant natural light, and an open split floor plan designed for comfortable Florida living. The home features 18" tile flooring, neutral paint, ceiling fans, recessed lighting, blinds, a dry bar, and decorative glass-tile accents throughout. The centrally located kitchen comes fully equipped with a smooth-top range, refrigerator, dishwasher, and built-in microwave, making it perfect for everyday living and entertaining. The spacious upstairs primary bedroom offers privacy and includes a walk-in closet, ceiling fan, and private bathroom with attractive decorative details. Step outside and enjoy your own private fenced patio oasis, complete with tile flooring and additional storage—an ideal space for relaxing or entertaining. One of the highlights of this home is the abundance of storage space throughout. The community offers excellent amenities, including a swimming pool, clubhouse, tennis court, and basketball court. Conveniently located near Full Sail University, shopping, restaurants, golf, and everything Winter Park is. Schedule your showing today and make this beautiful Winter Park condo your next home!

602 Trinidad Court Unit 602, Winter Park

$1,599,000
4 Beds ⋅ 4 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code
Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

533 Country Club Drive, Winter Park

$1,250,000
3 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE UNIQUE OPPORTUNITIES: Option 1 — $1,250,000 115' x 65' property + 65' lakefront lot. Option 2 — $1,450,000 155' x 65' property + 65' lakefront lot. Option 3 — $2,250,000 155' x 95' property + 95' lakefront lot. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park

$2,095,000
4 Beds ⋅ 4 Baths ⋅ Lake Virgina Shores SubDv. ⋅ 32789 Zip Code
Welcome to the Timberlane Shores area, one of Winter Park's most desirable and established neighborhoods. This beautifully updated home sits on over a third of an acre with deeded access to Lake Virginia. Impeccably maintained, the 4-bedroom, 4-bath home offers 3,776 square feet of heated living space, including an office and sunroom. Inside, a welcoming foyer opens to a traditional floor plan with large formal living and dining rooms on either side. Straight ahead, the spacious family room with fireplace flows into the kitchen, where new quartz countertops and backsplash, upgraded appliances, and gorgeous travertine floors make this a true chef's kitchen. Beyond the kitchen, a light and bright sunroom looks out over the inviting pool and patio with outdoor kitchen. The downstairs office could easily be converted to a first-floor bedroom with an adjacent full bath. Upstairs, you'll find a large primary suite and three additional bedrooms. One of the home's most inviting features is the expansive upper balcony stretching the length of the house and overlooking the pool, perfect for entertaining or enjoying a quiet evening outdoors. Recent updates include a newly renovated kitchen, 2017 roof, and newly reimagined landscaping. Zoned for Audubon Park K-8 and Winter Park High School, and close to Winter Park's historic restaurant and shopping district, this is the perfect location to enjoy everything the area has to offer.

555 E Lake Sue Avenue, Winter Park

$1,095,000
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining. The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen to dining to living, anchored by a fireplace made for slow evenings, and new engineered hardwood flooring runs throughout the entire house. All 3.5 baths are completely redone with marble floors, designer tile, and brass fixtures, including a first floor half bath with wall paneling and a one of a kind vanity that stops people mid tour. This remodel went beyond the pretty parts. A brand new roof covers the entire house and detached garage, all outlets and switches were replaced throughout, and the plumbing was redone for the kitchen and all bathrooms. The water heater is new, and the laundry room has a new stacked washer and dryer too. You move in and live, nothing to fix, nothing to update. Upstairs and down, every bedroom is spacious and has custom built in closet systems, and the stairway shows off custom oak newels and handrails with black metal balusters. Outside, the charm continues with a herringbone brick-tile front porch, balconies and back porch made for morning coffee, fresh paint inside and out, new landscaping, a new paver driveway, and a detached two car garage with a newly stained concrete floor. This is not a quick flip. Every finish was chosen with intention, and every detail was completed with care. 4 bedrooms, 3.5 baths, 2,135 sq ft of living space on a 7,151 sq ft lot, in one of Winter Park's most loved pockets. This is a home you will feel from the first moment you walk in.

1517 Harmon Avenue, Winter Park

$2,190,000
4 Beds ⋅ 3 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code
A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning property offers a secluded setting that feels worlds away, while world-class dining and shopping, trails and parks, and the vibrant Village Center of renowned Baldwin Park are just moments from your door. Inside, you'll find luxury finishes and appliances, expansive hurricane-impact windows, all-new HVAC and a whole-house water filtration system, along with double master suites with vaulted ceilings and distinctive architectural details throughout. Step outside, where 158 feet of lakeshore and your private dock invite you to enjoy the water at its best, from boating and waterskiing to beautiful sunrises and sunsets on the water. With approximately 3,400 square feet, four bedrooms, three baths, a detached garage/workshop and no HOA, this is a truly unique offering in one of Winter Park's most desirable locations.

1803 Barker Drive, Winter Park

$299,900
3 Beds ⋅ 2 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code
FULLY FURNISHED and ready for its next owner! This 3-bedroom, 2-bath Winter Park home offers an excellent combination of recent improvements, location, and flexibility. Major updates include a NEW ROOF (2021), FULL HOUSE REPIPE (2025), and NEW FLOORING (2025), giving buyers peace of mind on several important big-ticket items. Situated on an OVERSIZED 0.24-ACRE LOT with NO HOA, the property offers a spacious yard with plenty of room to enjoy the outdoors. Inside, the home features a comfortable and functional layout with an eat-in kitchen, indoor laundry, and inviting living spaces. Even better, the home is being sold FULLY FURNISHED, making it an easy option for a primary residence, second home, or investment property. The location is hard to beat, with convenient access to Full Sail University, Rollins College, UCF, Park Avenue, Baldwin Park, shopping, dining, and major roadways connecting you throughout Central Florida. With NO HOA and short-term rental potential, this property provides flexibility that can be difficult to find in Winter Park. Whether you're looking for a place to call home or an investment opportunity, 5080 Seminole Ave is ready for its next chapter!

5080 Seminole Avenue, Winter Park

$699,000
3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
Welcome to Park West, an exclusive gated community ideally located just moments from the heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bath residence offers a spacious and thoughtfully designed floor plan. The inviting living and dining areas feature an open-concept layout anchored by a traditional decorative fireplace, creating a warm and comfortable setting for both everyday living and entertaining. The generous primary suite offers a private en-suite bath with a walk-in shower and an expansive walk-in closet. The second bedroom is conveniently positioned near the hall bath, which features a tub/shower combination. A dedicated laundry room with built-in shelving and abundant storage adds a level of convenience rarely found in condominium living. Residents of Park West enjoy an array of amenities, including a clubhouse, resort-style swimming pool, and tennis court which also has lines for pickleball, all within a beautifully maintained gated setting. Perhaps the greatest luxury is the location. From Park West, it’s an easy stroll to the boutiques, restaurants, and cultural attractions of Park Avenue, as well as Central Park, world-class museums, the SunRail station, and the Winter Park Golf Course. Offering space, comfort, amenities, and an unbeatable location, this is a wonderful opportunity to own a residence in one of Winter Park’s most desirable communities.

250 Carolina Avenue Unit 202, Winter Park

$474,900
3 Beds ⋅ 2 Baths ⋅ Winter Park Forest SubDv. ⋅ 32792 Zip Code
Realtor partners, give your buyers the opportunity to secure 3334 Young Street, Winter Park, FL 32792. This fully renovated, block-construction, three-bedroom, two-bathroom home with a two-car garage is currently the only property of its kind available within a half-mile radius. Competing homes are outdated, smaller, and fewer bedrooms, or lack a garage. The comprehensive renovation includes an opened and redesigned kitchen, brand-new flooring throughout, two completely renovated bathrooms, a new 2026 air-conditioning system, new windows, fresh interior and exterior paint, and much more. The list of improvements is so extensive that detailing every upgrade could fill two pages—this home truly must be seen to appreciate the quality and scope of the renovation. Contact me directly for sold comparables, additional due-diligence information supporting the property’s value, or to schedule a private showing.

3334 Young Street, Winter Park

$925,000
4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 2nd Add SubDv. ⋅ 32792 Zip Code
Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021 and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020 and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024. The garage is air-cooled. Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional, conveniently situated in a wonderful community with Cady Way pool and Cady Way trail, which spans 7.2 miles and connects to the Seminole Trail outdoor recreation. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

2572 Fifeshire Drive, Winter Park

$3,495,000
5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
Timeless elegance meets effortless modern living in this exceptional five-bedroom, 5.5-bath residence in Park Grove, one of Winter Park's most coveted neighborhoods. Designed for gracious living and sophisticated entertaining, the home features formal living and dining spaces alongside an expansive open-concept family room and gourmet kitchen. The first floor offers a serene primary suite, a private guest suite and a dedicated office, while the second level provides three generously sized guest suites, a versatile bonus room and a second laundry room. Retractable accordion doors extend the living space outdoors, creating a seamless connection between the sophisticated interiors and outdoor living areas. Outside you will find retractable screens along the porch area along with a putting green conveniently located beside the pool. Rich hardwood floors, custom trim and molding and exceptional interior finishes add warmth and refinement throughout. The gourmet kitchen is beautifully appointed with solid wood cabinetry, quartz countertops and premium appliances. Ideally situated in Park Grove, this distinguished residence offers the rare combination of privacy, luxury and navigability, just moments from Park Avenue, the Winter Park Village and the Winter Park Golf course.

662 Granville Drive, Winter Park

$5,500,000
5 Beds ⋅ 7 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. PRE-CONSTRUCTION: Introducing an exceptional new construction residence by Nautilus Homes, ideally positioned in the heart of Winter Park near Lake Osceola, with convenient side access from Via Bella. This remarkable five-bedroom, full bath and two half bath residence brings together Organic Modern architecture with Contemporary West influences, combining clean architectural lines with natural stone, warm wood elements, expansive glass, and organic textures throughout. Step through the entrance into a dramatic grand foyer, where expansive glass and architectural floating stairs immediately introduce the home's modern design. Natural materials and thoughtfully selected organic elements transition seamlessly from the exterior into the interior, creating warmth and continuity throughout the residence. Beyond the foyer, the home opens into an impressive great room, where expansive glass fills the space with natural light and creates a strong connection to the outdoor living areas. A sleek linear electric fireplace serves as an architectural focal point, complementing the clean lines and warm organic materials found throughout the home. At the heart of the residence is a thoughtfully designed chef's kitchen featuring top-of-the-line appliances sub Zero and Wolf and a dramatic double-island configuration, providing exceptional space for preparation, casual dining, and entertaining. Just beyond the kitchen, a thoughtfully designed combination mudroom and pantry provides additional storage and everyday functionality while maintaining the home's clean, luxurious aesthetic. An impressive wine storage wall adds another distinctive element to the main entertaining spaces. The primary suite is designed as a private retreat, complete with the added convenience of a dedicated laundry room positioned just off the primary suite. An extensive architectural lighting package and integrated smart-home technology further enhance the home's combination of luxury, functionality, and modern living. A dedicated entertainment room provides an additional space for gathering and relaxing, while the second floor offers additional bedroom accommodations and a versatile bonus room, ideal for a media lounge, game room, home office, or secondary entertainment space. The home's indoor living spaces transition naturally to one of its signature features—an impressive 42-foot-long lanai designed for year-round Florida living. Anchored by a gas fireplace, this expansive covered outdoor space creates an exceptional setting for entertaining, dining with automatic drop screens for relaxing while extending the home's Organic Modern design into the outdoors. Completing the residence with a perfect size pool/spa with ample yard space. A three-car garage configuration, including a separate detached one car garage. Depending on final dimensions and equipment specifications, the detached one-car garage may potentially accommodate a vehicle lift for additional automobile storage, creating an attractive feature for the automotive enthusiast or collector. Winter Park is renowned for its upscale retail, high-end dining, and vibrant culinary community, offering an exceptional blend of luxury and lifestyle. Just minutes away, enjoy the boutiques, restaurants, cafés, and charm of Park Avenue, along with convenient access to two nearby golf courses, making this an ideal location for experiencing the best of Winter Park living.

1166 Palmer Avenue, Winter Park

$675,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully harmonizes timeless architectural soul with stylized contemporary updates. Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood. Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror. Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod. Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed. All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando.

2215 Woodcrest Drive, Winter Park

$850,000
3 Beds ⋅ 3 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code
Welcome to this beautiful Winter Park home where a flagstone, ivy-lined entry sets the tone for the inviting spaces found within. Tucked away on a private .21-acre lot, this 3-bedroom, 3-bathroom home offers 2,488 square feet of thoughtfully designed living space with vaulted ceilings, multiple living areas, and an effortless flow that makes everyday living and entertaining feel natural. From the moment you arrive, the lush new landscaping and charming entry create a warm first impression, while the spacious interior offers plenty of room for family and friends to gather, relax, and enjoy time together. Inside, the home's multiple living areas provide exceptional flexibility, creating inviting spaces for entertaining, casual gatherings, or simply relaxing with family. The kitchen serves as a natural gathering point, featuring white shaker cabinetry, granite countertops, brand-new stainless-steel appliances, a convenient coffee/wine bar, and a breakfast bar with seating for four. Whether hosting friends for dinner or enjoying a quiet morning together, the layout offers space for every occasion. The primary suite, thoughtfully added in 2017, is a private retreat designed for both comfort and relaxation. A dedicated sitting room or office provides additional flexibility, while the spacious walk-in closet offers abundant storage. The expansive ensuite bathroom delivers a true spa-like experience, featuring a large tiled shower with multiple shower heads and a frameless glass enclosure, creating a luxurious place to unwind at the end of the day. A dual vanity with elegant marble countertops and a separate water closet complete this serene retreat. A secondary bedroom with its own ensuite bathroom provides additional comfort and privacy for guests or family members. All bathrooms have been updated, and the bedrooms feature brand-new carpet, while recessed lighting and ceiling fans throughout add to the home's comfort. Step outside to enjoy the privacy of the fully fenced backyard, with fencing replaced in 2025, a brand-new deck, and beautiful new landscaping. The outdoor space offers another inviting setting for relaxing, entertaining, or enjoying Florida's year-round lifestyle. Beyond the home, the location places you just steps from Brookshire Elementary and close to the Cady Way pool, playground, beach volleyball, tennis and pickleball courts, Cady Way Trail, and Winter Park Pines Golf Course. You'll also enjoy convenient access to UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center, with Orlando International Airport approximately 25 minutes away. With its welcoming entry, versatile living spaces, spa-inspired primary retreat, private setting, and exceptional Winter Park location, this home offers an ideal backdrop for gathering, relaxing, and making memories with family and friends. ROOF(S) - Main - 2022, Family Room - 2019, Primary Suite - 2017 HVAC - 2021 MINI-SPLIT - 2026

2345 Brookshire Avenue, Winter Park

$134,900
2 Beds ⋅ 2 Baths ⋅ Whisperwood SubDv. ⋅ 32792 Zip Code
Welcome to 7302 Swallow Run! This beautiful, move-in ready 2-bedroom, 2-bathroom condo offers the highly sought-after first-floor location and a prime setting directly across from both community pools. Nestled within the desirable Whisperwood community in Winter Park, this single-story condo features a wonderful split-bedroom floor plan and an open living concept with plenty of space to relax and entertain. Enjoy the convenience of NO CARPET throughout the home, along with a spacious living area that opens to a private balcony—perfect for enjoying your morning coffee or unwinding at the end of the day. The beautiful kitchen features gorgeous cabinetry, ample counter space, plenty of storage, and a full suite of appliances, all overlooking the open living area. A convenient breakfast bar provides additional seating, making everyday living and entertaining a breeze. The unit also includes a stackable washer and dryer for added convenience. Whisperwood is a quiet, welcoming condominium community with friendly neighbors and plenty to enjoy. Residents can take advantage of the community amenities and beautifully maintained grounds, all included in the affordable HOA fee. This particular unit enjoys an especially desirable location directly across from both community pools, a beautiful pond, and the community mailboxes. Beyond the community, you’ll enjoy all that the charming city of Winter Park has to offer. Located just three miles north of downtown Orlando, Winter Park is celebrated for its strong sense of community, beautiful parks, scenic chain of lakes, elegant homes, brick-lined streets, and mature tree canopy. The city offers an exceptional blend of historic charm and modern conveniences, with an array of shopping and dining destinations, museums, cultural attractions, and the renowned Rollins College. Conveniently located near Full Sail University and just a few miles from Rollins College, this home also provides easy access to major roadways including SR 408, SR 417, and SR 436. Come see 7302 Swallow Run and experience the convenience, charm, and lifestyle that make Winter Park such a wonderful place to call home!

7302 Swallow Run Unit 7302, Winter Park

$1,579,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Under Construction. UNDER CONSTRUCTION | LUXURY NEW BUILD | Presented by LUIH Luxury Homes Welcome to 2417 Chantilly Avenue, an exceptional luxury new construction residence in beautiful Winter Park, Florida, where sophisticated design, elevated finishes, and effortless indoor-outdoor living come together. This stunning 4-bedroom, 3.5-bath home features an expansive open-concept floor plan enhanced by upgraded luxury finishes and engineered hardwood flooring throughout. At the heart of the home, the chef-inspired kitchen is designed to impress with premium Thermador appliances, an oversized island, beautiful cabinetry, generous prep space, and a seamless connection to the main living and entertaining areas. The first-floor primary suite offers a private retreat with direct access to the backyard and pool, creating a tranquil connection to the home's outdoor spaces. Step outside and discover your own private oasis. The beautifully designed backyard features a sparkling pool and summer kitchen, providing the perfect setting for entertaining, dining al fresco, or simply relaxing in the Florida sunshine. With 4 bedrooms, 3.5 baths, sophisticated finishes, an open and inviting layout, and exceptional indoor-outdoor living, 2417 Chantilly Avenue delivers the elevated lifestyle today's luxury buyer is looking for—all in one of Winter Park's most desirable locations.

2417 Chantilly Avenue, Winter Park

$895,000
4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 4th Add SubDv. ⋅ 32792 Zip Code
Virtually Staged. Fully renovated from top to bottom, this 4-bedroom, 3-bathroom pool home sits on a 9,915-square-foot lot in Winter Park's Brookshire Heights, one of the area's most established and tree-lined pockets. The kitchen has been completely rebuilt with new cabinetry, new appliances, and new finishes, and that same attention carries through the rest of the house — new flooring throughout, new windows, new water heater, and fresh paint inside and out. The two systems that matter most to a buyer's peace of mind are both new for 2025: a new roof and a new AC system, so there's no guessing what's left to replace. Outside, the pool has been fully resurfaced, giving it a clean, ready-for-summer finish, and the fenced backyard offers space to entertain or just enjoy Florida's outdoor living. A 2-car garage pairs with an extra-large driveway, giving this home more parking flexibility than most on the street. The washer and dryer convey with the sale. Brookshire Heights is zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School, and the location puts you minutes from Cady Way Trail, Park Avenue's shops and restaurants, Rollins College, and Winter Park Pines Golf Club, just a few streets away. It's a neighborhood known for quiet, walkable streets and mature landscaping, close enough to downtown Winter Park to feel connected without the noise. Every major update on this home has already been made — what's left is simply moving in

618 Blairshire Circle, Winter Park

$960,000
2 Beds ⋅ 1 Baths ⋅ Ethel Park SubDv. ⋅ 32789 Zip Code
An outstanding opportunity to acquire a generously sized homesite in the highly desirable City of Winter Park area. Measuring approximately 75' x 154', this 11,555-square-foot lot offers excellent potential for a custom luxury residence. This property is being offered for its land value, presenting an ideal opportunity for a builder, developer, investor, or buyer looking to create a custom home tailored to today's luxury lifestyle. The Winter Park area hosts a remarkable collection of luxury homes, custom estates, and continued new development, making this an attractive location for those seeking to build in an established and highly desirable market. With its generous lot dimensions and surrounding luxury development, this property provides an excellent canvas for your next custom-home project.

447 N Phelps Avenue, Winter Park

$450,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 16 SubDv. ⋅ 32792 Zip Code
VIRTUALLY STAGED! EXCEPTIONAL POOL HOME IN EASTBROOK! Welcome to Conifer Avenue, where pride of ownership, and an unbeatable Winter Park-area location come together beautifully. This impressive pool home offers an outstanding opportunity to own a well-maintained residence in the highly sought-after Eastbrook community. This FOUR BEDROOM 2 Bath home offers almost 2200 square feet! Split bedroom plan PLUS 21 x 12 office/bonus room; formal living, dining & family rooms;2024 NEW HVAC-POOL PUMP 2025-ROOF 2019-zoned for excellent Seminole County Schools! Oversized 20 x 22 two car garage with additional storage space. Extras include: updated windows; all appliances including washer & dryer; quaint front porch. Call for your private showing! Step outside and discover your own private retreat! Multiple sets of sliding glass doors open to the large screened-in lanai, sparkling swimming pool, and expansive pool deck, creating an exceptional indoor-outdoor living and entertaining space. The nearly quarter-acre lot is fully fenced, offering plenty of room for pets, play, gardening, and outdoor enjoyment. The oversized two-car garage provides generous parking and an abundance of storage options. This is truly an entertainer's dream home—whether you're hosting friends around the pool, enjoying a quiet evening outdoors, or simply relaxing in your own private backyard oasis. And then there's the LOCATION! LOCATION! LOCATION! Convenient access to I-4 and SR 417 makes traveling throughout Central Florida a breeze, with easy access toward Orlando's attractions, Disney, the beaches, shopping, dining, and entertainment. Enjoy being close to the charm of Historic Downtown Winter Park and Park Avenue, including its fabulous restaurants, boutique shopping, cultural attractions, and popular weekly Farmers Market. SunRail is also conveniently nearby, providing another great transportation option throughout Central Florida.

2301 Conifer Avenue, Winter Park

$234,900
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated kitchen with White shaker cabinets, granite counters complete with all the appliances including washer and dryer. Formal dining room and family room with vaulted ceilings, skylights, along with a wet bar and cabinetry complimented by a centerpiece wood burning fireplace. Master bedroom features hardwood flooring along with updated vanity with granite counters along with a separate tub and shower. Secondary bedroom has laminate flooring along with updated vanity and granite countertops. Ceramic tile throughout the rest of the home as there is no carpet. French doors leading out to the oversized screen enclosed covered patio overlooking lush landscaping with no direct rear neighbor.  2 assigned parking spaces directly in front of the unit.There is also a small courtyard just outside the kitchen. Community features a recently remodeled pool, clubhouse and tennis courts. Winter Park location benefits include easy access to Full Sail University, UCF, Valencia College, Park Avenue filled with famous restaurants and boutique shopping.

2383 Sun Valley Circle Unit 2383, Winter Park

$789,000
4 Beds ⋅ 3 Baths ⋅ Sherbrooke SubDv. ⋅ 32792 Zip Code
Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car garage, all in a convenient location within walking distance of Winter Park High School. 10 minutes to Full Sail University, Rollins College, or Downtown Winter Park. Step inside to find generous living and family spaces filled with natural light, beautiful hardwood flooring, and a flexible layout designed for both everyday living and entertaining. The upgraded kitchen features granite countertops, abundant wood cabinetry, stainless steel appliances, recessed lighting, a center island, and a breakfast bar overlooking the family room. The spacious primary suite features new vinyl flooring and an updated en-suite bathroom with dual vanities and a large walk-in shower. Three additional bedrooms provide plenty of flexibility for guests, home office space, or other needs. An additional full bathroom, half bath, and dedicated laundry room complete the interior. French doors lead to the screened patio, offering a comfortable space for outdoor dining and relaxing. Beyond the patio is an exceptionally large backyard surrounded by mature trees and landscaping, with plenty of room for gardening, recreation, entertaining, or creating your own outdoor retreat. Major improvements include a ROOF REPLACED IN 2022 and A/C REPLACED IN 2022, giving the next owner added peace of mind. With its upgraded kitchen and bathrooms, spacious floor plan, beautiful flooring, huge backyard, screened patio, two-car garage, and recently replaced major systems, this Winter Park home offers an outstanding combination of space, comfort, and location. Schedule your private showing today and discover everything this home has to offer!

2410 Sherbrooke Road, Winter Park