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$689,900
4 Beds ⋅ 3 Baths ⋅ O6426672 MLS
Welcome to this beautifully maintained four-bedroom, three-bathroom home offering over 2,000 square feet of thoughtfully designed living space in desirable Winter Park community. Overlooking the 9th fairway of Winter Park Pines Golf Course, this home offers a picturesque golf course setting and a peaceful backdrop for everyday living. The split-bedroom floor plan provides both privacy and versatility, while the formal living and dining rooms create inviting spaces for entertaining. Light-toned wood and tile flooring flow throughout, complemented by crown molding, recessed lighting, and a wood-burning fireplace that adds warmth and character. The contemporary kitchen features honey-oak cabinetry, granite countertops, stainless steel appliances, a breakfast nook, and a center island with seating for two. The spacious primary suite is privately positioned from the secondary bedrooms and offers a generous walk-in closet and an impressive ensuite bathroom featuring floor-to-ceiling slate tile, an espresso-colored contemporary double vanity with glass vessel sinks, and a walk-in slate tile shower. Ideal for family or guests, a convenient Jack and Jill bathroom serves two bedrooms while the hall bathroom is directly adjacent to the fourth bedroom. A dedicated laundry room/mud room with built in shelving includes the washer and dryer. French doors open to the spacious screened lanai, where the scenic 9th fairway views take center stage. New screening was installed in 2021, creating an ideal setting for morning coffee, al fresco dining, or relaxing while enjoying the beautifully maintained golf course landscape. The quarter-acre lot also features lemon and Japanese blueberry trees, while the two-car garage offers built-in shelving and an updated garage door and mechanicals. Beyond the property, enjoy convenient access to the Cady Way Trail, Cady Way pool, playground, and tennis/pickleball courts, as well as nearby UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center. Orlando International Airport is approximately 20 minutes away. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines comfortable living, desirable amenities, and spectacular golf course views in a sought-after Winter Park location. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2015

943 Fairway Drive, Winter Park
$635,000
3 Beds ⋅ 3 Baths ⋅ O6434796 MLS ⋅ 565 BLDG.
Private, no-through-traffic street in one of Winter Park's most desirable locations. Just a short walk from downtown Winter Park and Park Avenue, this light-filled townhome offers the perfect combination of privacy, space, and convenience. Step inside to soaring ceilings, abundant natural light, and a spacious floor plan designed for comfortable everyday living and entertaining. The first floor features a generous living area, separate dining space, and an updated eat -in kitchen with plenty of cabinetry and workspace. Two private patios—one on each side of the townhome—extend the living space outdoors and provide wonderful spots for morning coffee, dining, entertaining, or simply relaxing. Upstairs, you'll find three generously sized bedrooms with excellent closet space. Thoughtfully designed closet organizers provide exceptional storage, while the spacious primary suite offers a comfortable and private retreat. High ceilings, large windows, abundant storage, and an inviting indoor-outdoor layout give this home a bright and open feel throughout. Meticulously cared for and updated this is an exceptional opportunity to enjoy low-maintenance townhome living without sacrificing space or privacy. Best of all is the location—enjoy the ability to walk to Park Avenue and experience the restaurants, shopping, cafés, parks, events, and charm that make downtown Winter Park one of Central Florida's most sought-after destinations. A rare combination of location, lifestyle, and livability!

565 Huntington Avenue Unit 565, Winter Park
$1,350,000
3 Beds ⋅ 4 Baths ⋅ O6434255 MLS
Welcome to 720 Pansy Ave, a distinctive three-story Winter Park home thoughtfully designed for both everyday living and flexible use. Fully remodeled in 2017, the residence offers a clean, contemporary interior with LVP and tile flooring, recessed lighting, crisp finishes, and an open flow through the main living spaces. The first floor includes a spacious living room, dining area, and a separate office/study/den, providing plenty of room to work, gather, and unwind. At the heart of the home, the modern kitchen features sleek white cabinetry, stainless steel appliances, generous storage, and a wide pass-through that keeps the kitchen connected to the dining and living areas. The first-floor primary suite offers the convenience of main-level living, complete with a walk-in closet and a beautifully finished primary bath featuring a steam shower. Large windows bring natural light into the home, while the neutral finishes create an easy backdrop for a variety of styles. Upstairs, two additional bedrooms are joined by flexible spaces that add to the home’s functionality, including a dedicated storage room on the second floor. Continue to the third level to find an expansive bonus space that can easily serve as a media room, game room, creative studio, home gym, or additional lounge. Practical features include a durable metal roof and a whole-house generator designed to keep the home powered during storms and unexpected outages, providing added comfort and peace of mind. Outside, the private backyard extends the living space with decking, a hot tub, landscaped green space, mature trees, and a gazebo for relaxing or entertaining. The location completes the package, placing you in the heart of the Winter Park lifestyle with convenient access to Park Avenue, known for its boutiques, restaurants, cultural attractions, and community events, as well as nearby Rollins College. Enjoy the character and charm of an established Winter Park neighborhood while remaining close to the shopping, dining, arts, and everyday conveniences that make this area such a desirable place to call home.

720 Pansy Avenue, Winter Park
$149,999
1 Beds ⋅ 1 Baths ⋅ O6434819 MLS ⋅ N/A BLDG.
Beautifully renovated first-floor 1-bedroom, 1-bath condominium in the highly desirable Parkview Village community, conveniently located directly across from Full Sail University on Semoran Blvd. This move-in-ready home features a spacious open-concept layout, an oversized bedroom with a walk-in closet, a dedicated laundry closet with a washer and dryer, and a private screened-in patio overlooking a beautiful mature tree for added privacy and relaxation. The home has been extensively updated with a newer A/C system, a fully renovated kitchen and bathroom, and a complete suite of stainless steel appliances-including the refrigerator, range, microwave, dishwasher, washer, and dryer-all replaced in 2022. Modern features include a preinstalled Nest Wi-fi thermostat, Eufy doorbell/lock, and wall-mounted TV brackets in both the living room and bedroom. Residents enjoy resort-style amenities including a community pool, hot tub, picnic and BBQ area, and a newly built fenced dog park. The location has easy access to Lake Baldwin, Downtown Winter Park, the University of Central Florida, Downtown Orlando, and Orlando International Airport. Major roadways including SR 436, SR 408, and East Colonial Drive are just minutes away, making commuting throughout Central Florida quick and convenient. Whether you're looking for a comfortable primary residence or an investment property, this exceptional condominium is the perfect combination of location, modern updates, and everyday convenience.

3019 Antique Oaks Circle Unit 127, Winter Park
$2,100,000
O6434781 MLS
A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custom dream home while enjoying the privacy and tranquility of one of Central Florida's premier waterfront locations. Spanning nearly 400 acres, Lake Howell is a skiable lake ideal for boating, water skiing, fishing, kayaking, canoeing, paddleboarding, and endless outdoor recreation. With expansive acreage, breathtaking water views, and ample space to create your own private estate, the possibilities are endless. The value is in the land, making this an incredible opportunity for those seeking a premier homesite in a highly desirable location. Don't miss your chance to own one of the area's rare large-acreage lakefront parcels.

1133 Bella Lago Cove, Winter Park
$299,000
3 Beds ⋅ 2 Baths ⋅ O6434684 MLS
Winter Park address with Seminole County taxes, and a new roof already in place from 2023. Three bedrooms, two baths, roughly 1,235 sf of living space in solid concrete block with central air. The 9,000 sf lot is fenced and shaded by mature oaks, with an established chicken coop and a 550 sf carport with workshop space. Flood Zone X, so no lender-required flood insurance. No HOA. No CDD. For an investor, the basis here pencils from day one and cosmetic updates move the rent meaningfully. For an owner-occupant, this is one of the last ways into a Winter Park address at this number. Offered as-is. Seller prefers a quick closing with post-closing occupancy up to 60 days, likely less.

2313 Knoll Street, Winter Park
$529,000
3 Beds ⋅ 2 Baths ⋅ TB8539207 MLS
Updated Winter Park home with 2,047 sq ft of heated/cooled living space, a huge backyard, and NO HOA. This is an owner-updated home—not a flip—with quality improvements completed over the past several years and professionally completed permitted work. Major improvements include a 2021 roof, 2021 whole-house repipe, 2021 exterior stucco and paint, 2020 HVAC, 2023 kitchen remodel, 2023 permitted 400 sq ft heated/cooled sunroom addition, 2024 permitted 20’ x 10’ storage building, and 2025 hurricane-impact windows. The expanded kitchen features granite countertops and backsplash, newer appliances, and a massive storage expansion. The bright 400 sq ft sunroom features wall-to-wall windows, a four-panel sliding glass door, and permanent AC and heat. A separate 200 sq ft tiled screened room provides additional outdoor living space. The property also offers a large backyard with plenty of room to enjoy, entertain, or expand. Located in a desirable Winter Park area with great schools and convenient access to shopping, dining, parks, and major roads. Extensive owner-quality improvements, major systems already updated, permitted additions, and no HOA. Buyer to independently verify all measurements, square footage, permits, schools, and other property information.

1660 Gladiolas Drive, Winter Park
$450,000
4 Beds ⋅ 2 Baths ⋅ O6434614 MLS
The one you’ve been waiting for! This beautifully redesigned home offers 4 bedrooms, 2 bathrooms, and nearly 1,700 square feet of thoughtfully curated living space. Manchester offers both style and peace of mind with major upgrades including a 2026 A/C, 2024 roof, 2026 windows, Brand new privacy fence, 2026 garage door, and 2026 electrical panel. At the heart of the home is a stunning designer kitchen featuring custom wood cabinetry, Taj Mahal countertops, a dedicated coffee bar, and an open layout designed for both entertaining and everyday living. Every space has been intentionally designed to be as functional as it is beautiful, with a split floor plan, custom bathrooms, and ample storage throughout. The private primary suite is thoughtfully positioned on its own side of the home and features a walk-in closet and en-suite bathroom. Situated on an oversized lot, the spacious backyard offers plenty of room for entertaining, playing, and making memories. With beautiful finishes, extensive upgrades, and zoning for A-rated schools, Manchester is one you won’t want to miss. Come see it before it’s gone!

1011 Manchester Circle, Winter Park
$417,500
3 Beds ⋅ 3 Baths ⋅ O6434185 MLS ⋅ 2857 BLDG.
Almost brand new and move in ready CORNER townhome in Winter Park! This beautiful 3 bedroom 2.5 bathroom home with just under 1,800 sq. ft. offers a large 2 car garage, light and bright living spaces, clean and modern designer features, and comes equipped with a full kitchen appliance package and washer/dryer. The first floor offers expansive living spaces with enough room for a dining area and family room. All of which flow seamlessly into the open kitchen. With white cabinets and Quartz counter tops, the kitchen is a show stopper! The entire first level is adorned with tile and offers a half bathroom and access to the covered back porch. Just up the stairs, you will find all of your bedrooms and full bathrooms. The primary bedroom and en suite bathroom are ample in size and also offer a large walk in closet. Both secondary bedrooms are down the hall and share a large full bathroom. The small gated community of townhomes offers a community pool and serene pond. HOA includes cable! Make sure to put this on your must see list!

2857 Clever Lane, Winter Park
$799,000
3 Beds ⋅ 3 Baths ⋅ O6417455 MLS ⋅ Casa Jardin BLDG.
In the heart of Winter Park’s coveted Virginia Heights neighborhood, just moments from the boutiques, dining, and charm of Park Avenue and the green spaces of Seven Oaks Park, this exceptional Mediterranean-inspired end-unit condominium offers an unparalleled blend of elegance, comfort and accessible convenience. Encompassing nearly 2,000 square feet, the residence features three bedrooms, two-and-a-half baths and a thoughtfully designed floor plan that lives like a private home. Bathed in natural light, the interiors are framed by expansive window walls and floor-to-ceiling glass doors that create a bright, airy ambiance throughout. Architectural details including graceful arched passageways, column-lined hallways, and a custom wrought-iron spiral staircase add timeless character and sophistication. Beautifully updated and meticulously maintained, every room reflects a sense of warmth and refinement. The spacious primary retreat is a sanctuary, featuring soaring cathedral ceilings, dual walk-in closets and a spa-inspired bath designed for relaxation. Two additional bedrooms offer versatility for guests, family or a home office. The open-concept living and dining areas are enhanced by travertine and luxury vinyl plank flooring, coffered ceilings, designer lighting, and a beautifully appointed chef’s kitchen complete with solid wood cabinetry, granite countertops, a center island and generous walk-in pantry. French doors open to a freshly painted screened courtyard, creating a private outdoor escape ideal for entertaining or quiet evenings at home. Above, the freshly painted rooftop terrace provides a spectacular setting for alfresco dining, sunset gatherings or simply enjoying Florida’s year-round sunshine. Additional features include a powder bath, plantation shutters, ceiling fans throughout, an oversized two-car garage, and a third-floor walk-in attic offering abundant storage and exciting future expansion possibilities. Residents of Casa Jardin enjoy a beautifully refreshed community, recently enhanced with a new roof, exterior paint and professional landscaping. Ownership also includes exclusive access to Lake Virginia and renowned Winter Park Chain of Lakes through College Point, featuring a private lakefront gathering area along with kayak and paddleboard storage. Ideally near Azalea Lane Recreation Center, the Winter Park Tennis Center, Orange Avenue’s popular restaurants and shops, and top-rated schools, this remarkable residence offers a rare opportunity to enjoy one of Central Florida’s desirable lifestyles.

1278 S Pennsylvania Avenue Unit 13, Winter Park
$3,999,000
5 Beds ⋅ 6 Baths ⋅ O6428414 MLS
Designed to evoke the timeless architecture of Olde Winter Park, this exceptional modern Tudor home features character, craftsmanship, and presence rarely found in today's market. Perfectly positioned on an expansive 0.37-acre homesite in the highly coveted Park Grove neighborhood, the residence offers the rare privilege of walking to Park Avenue while still having immense privacy. A soaring 20-foot foyer creates an unforgettable first impression and immediately establishes the home's sense of grandeur. Beyond the entry, the expansive great room is defined by dramatic exposed wood beams, a sleek electric fireplace, and a custom-built entertainment wall accented with subtle LED underlighting. At the heart of the home, the chef's kitchen is equal parts statement and workspace. Custom cabinetry is paired with a full Thermador appliance suite, including a paneled built-in refrigerator, while striking Taj Mahal quartzite countertops complete the space. Just beyond, an oversized butler's pantry dramatically expands the kitchen's functionality. Outfitted with extensive cabinetry, generous prep space, a secondary refrigerator, sink, and dishwasher, it is designed to support everything from intimate dinners to large-scale entertaining. The adjacent dining room is equally refined, featuring a custom dry bar complete with a built-in wine refrigerator. One of the home's most exceptional attributes is its floor plan. Offering two luxurious primary suites, a rarity in Winter Park, the residence provides remarkable flexibility for multigenerational living or extended guests. Both suites feature custom Idelli closet systems and spa-inspired baths appointed with marble mosaic tile, expansive walk-in showers, freestanding soaking tubs, and dual vanities. Every additional bedroom is designed as a private ensuite with its own walk-in closet. Two guest suites are conveniently located on the main level, while upstairs you'll find a spacious game room, a dedicated study nook for kids, and a second laundry room to complement the main-level laundry. The outdoor living experience is equally impressive. An expansive backyard, rarely found in Winter Park, creates a private setting for everyday living and entertaining alike. A covered lanai with a fully equipped summer kitchen overlooks the resort-style pool and spa, while upgraded landscaping and generous green space complete the grounds. An oversized motor court and a three-car garage with soaring 12-foot ceilings provide an uncommon level of parking and storage for the car enthusiast. Positioned just moments from Park Avenue, Winter Park Village, and Hannibal Square, this is far more than another luxury home. It is a thoughtfully crafted masterpiece that captures the timeless character of Olde Winter Park while delivering the scale, amenities, and craftsmanship expected of a modern home. Opportunities to own a property of this caliber, in a location this desirable, are exceptionally rare. Don't miss out!

1417 Williams Drive, Winter Park
$430,000
3 Beds ⋅ 2 Baths ⋅ O6434420 MLS
MULTIPLE OFFERS. Submit highest and best by 11:00 am 8/20/2026. Winter Park Pines….this 3 bedroom 2 bath pool home is ready for a new owner. The home features a split bedroom plan, formal living and dining room. The family room offers views of the backyard and pool area. Updates…roof 2020 and water heater 2024 and it was re-piped at some point. Great location ..on a “low traffic” street. Community features…Winter Pines Golf course ..at the end of Ranger Blvd. Playground nearby and miles of walking/biking trails on Cady Way trail. Just a few minutes to Park Ave. Publix, Sprouts, Aldi and restaurants nearby. Advent Health Winter Park is a few minutes away. This home needs TLC and is being sold AS-IS. Central AC does not work.

2765 Abbey Road, Winter Park
$775,000
4 Beds ⋅ 4 Baths ⋅ O6434086 MLS
Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park
$419,000
4 Beds ⋅ 2 Baths ⋅ G5115442 MLS
Virtually Staged. Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful 4 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your storage convenience. This beautiful done home was renovated in ,2024 with lot of upgrades and it is situated in desirable winter Park , which is close proximity to shopping, downtown ,highways , airport , universities( U.C.F) etc. No H.O.A fees ,the open concept layout gives this home a sense of comfort , convenience , spaciousness and a pleasant and relaxing ambiance. The home is move in ready and the front yard is ready for your customized landscape.Be the lucky one to own this home.Roof was redone in February/2020.

1842 Puritan Avenue, Winter Park
$860,000
5 Beds ⋅ 4 Baths ⋅ O6434232 MLS
Virtually Staged. Set on nearly an acre in Winter Park, this stately two-story home offers five bedrooms and three and a half bathrooms across more than 3,200 square feet of elegant living space. A dramatic two-story foyer with a sweeping staircase welcomes you into light-filled formal and casual living areas, including a spacious great room anchored by a fireplace. The gourmet island kitchen features rich cabinetry, stainless steel appliances, and generous counter space, flowing effortlessly to the surrounding living and dining spaces finished with wood-look flooring. The expansive primary suite provides a spa-like bath with a soaking tub and a separate glass-enclosed shower, while four additional bedrooms offer ample room for rest or a home office. Outside, a screened, in-ground pool and spa are framed by a paver deck and a large fully fenced yard, complemented by a covered patio and an oversized three-car garage. A rare offering of space and comfort on a generous, secluded lot. Included 100-Day Home Warranty with buyer activation

120 Longbranch Road, Winter Park
$660,000
3 Beds ⋅ 3 Baths ⋅ O6432855 MLS ⋅ 1 BLDG.
Very well maintained townhouse great location in Waterbridge on cul-de-sac near tennis courts. This 2 bedroom/den or 3 bedroom , 3 bathroom with primary upstairs and additional bedroom on main floor is renovated with hardwood floors downstairs, updated recessed lighting throughout, updated plumbing, volume ceilings, great ambient light and windows, barrel tile roof. Kitchen with updated appliances, cabinetry with undermount lighting and granite with courtyard for fountain feature or small table for morning coffee. Open dining living room combination with a fireplace. Primary bathroom has dual sinks, granite counters, bidet and custom tile. Primary Bedroom has gas fireplace. Outdoor living is perfect for entertaining with screened covered atrium with brick paver patio to enjoy Florida breezes. This townhouse has everything. Near restaurants, hospital, schools and downtown Winter Park Towncenter at Baldwin Park. Walk to Blue Jacket Park. Move in ready.

1256 Melissa Court, Winter Park
$1,050,000
2 Beds ⋅ 2 Baths ⋅ O6432808 MLS ⋅ Building 4 BLDG.
Experience effortless Winter Park living in Whispering Waters, a premier 55+ lakefront community beautifully situated along the shores of Lake Osceola and just a short stroll from Park Avenue. Priced below appraised value, this rare third-floor mid-century modern condo offers exceptional value and a truly turnkey lifestyle. Filled with natural light, the thoughtfully designed floor plan features spacious living and dining areas overlooking tranquil waterfall ponds and lush, beautifully maintained grounds. A versatile bonus space provides the perfect setting for a home office, den, or creative retreat. The expansive owners suite is designed for relaxation, featuring a private sitting area, dual closets, direct access to the pool, and a spa-inspired bath complete with a jetted tub. The generously sized secondary bedroom offers a cozy reading nook and dual closets, providing comfort and flexibility for guests. Enjoy effortless, worry-free living with secure underground parking, a deeded parking space, and convenient elevator access. Even better, monthly association dues include electricity, air conditioning, heat, water, sewer, and trash—making everyday living remarkably simple. Step outside your door and enjoy everything that makes Winter Park so special, from the acclaimed shops and restaurants of Park Avenue to Rollins College and Winter Parks historic nine-hole golf course. With its prime lakefront setting, exceptional location, and low-maintenance lifestyle, this is a rare opportunity to own a piece of one of Central Florida’s most desirable communities. Discover the best of Winter Park living at Whispering Waters—schedule your private showing today.

311 E Morse Boulevard Unit 4-5, Winter Park
$739,000
2 Beds ⋅ 2 Baths ⋅ O6433913 MLS ⋅ 250 BLDG.
Discover the ease of Winter Park living in the highly desirable gated community of Park West, ideally located just steps from Park Avenue. From this exceptional location, charming boutiques, sidewalk cafés, award-winning restaurants, and the popular weekly farmers market are all within easy reach—giving you the freedom to leave the car behind and enjoy everything Park Avenue has to offer. This beautifully remodeled second-floor corner residence offers the privacy, comfort, and convenience you've been looking for. The thoughtfully updated kitchen features wood cabinetry and granite countertops, while both bathrooms have been tastefully remodeled. Spacious bedrooms, generous storage, and a comfortable flow throughout the home provide plenty of room for everyday living or welcoming guests. Enjoy the simplicity of a well-maintained community with beautifully landscaped grounds, a sparkling swimming pool, and tennis courts. As a corner unit, this residence also offers enhanced privacy and convenient access into and out of the building—perfect for those seeking a low-maintenance lifestyle or an easy lock-and-leave retreat. With Rollins College and Full Sail University nearby and Park Avenue just moments away, this condo puts the best of Winter Park right at your doorstep. Whether you're looking for a full-time residence, a seasonal escape, or simply a home that allows you to spend less time on maintenance and more time enjoying life, Park West offers an exceptional combination of location, comfort, and convenience.

250 Carolina Avenue Unit 205, Winter Park
$299,000
3 Beds ⋅ 1 Baths ⋅ O6433927 MLS
Virtually Staged. Prime Winter Park Opportunity – Original Terrazzo Floors, Solid Block Construction & Endless Potential Discover an exceptional opportunity to own a classic Winter Park home priced at just $299,000. Situated on a generous 0.20-acre lot, this 3-bedroom, 1-bath concrete block home offers 1,208 square feet of living space and the perfect foundation to create your dream home or next investment. Built in 1960, this home showcases beautiful original terrazzo floors, a timeless feature that has become increasingly desirable and can be restored to complement today's popular mid-century modern and contemporary designs. The functional floor plan, abundant natural light, and solid construction provide the ideal canvas for renovation while preserving the home's authentic character. Major improvements have already been completed, including a roof replacement in 2021 and an HVAC system installed in 2018, allowing the next owner to focus on bringing their personal vision to life. To help buyers visualize the possibilities, one of the listing photos features an AI-generated renovation concept illustrating the home's exciting transformation potential. Location is everything, and this home delivers. Nestled in one of Central Florida's most sought-after communities, you'll enjoy convenient access to Downtown Winter Park, Park Avenue, Baldwin Park, Winter Park Village, Rollins College, AdventHealth, top-rated dining, shopping, parks, and major roadways. Whether you're looking to restore a classic mid-century home, renovate for resale, or customize a home that's uniquely your own, opportunities like this under $300k in Winter Park are becoming increasingly rare. Bring your vision and unlock the incredible potential of this Winter Park gem.

2168 Ridge Drive, Winter Park
$575,000
4 Beds ⋅ 2 Baths ⋅ O6430894 MLS
Modern Ranch Gem on a Corner Lot | 4 Bed | 2 Bath | 2,126 Sq Ft | Screened Pool | No HOA | Winter Park, FL Welcome to this beautiful 4-bedroom, 2-bathroom ranch-style home in Winter Park Estates! Situated on a desirable corner lot with no HOA, this spacious 2,126-square-foot home offers flexibility, comfort, and plenty of room to enjoy Florida living. The inviting floor plan features a huge bonus room, perfect for a media room, home office, playroom, gym, or additional living space. The updated kitchen offers a fresh, modern feel while maintaining a practical layout. Step outside to your screened-in pool and spacious outdoor area, ideal for relaxing, entertaining, and enjoying the Florida sunshine year-round. With four bedrooms, two full bathrooms, a generous bonus room, a corner lot, and no HOA restrictions, this home offers an exceptional combination of space and convenience in Winter Park. You will be close to charming downtown shops, restaurants, parks, and easy access to Orlando amenities, all while enjoying a quiet residential setting. A must-see for buyers looking for a move-in-ready home with room to live, work, and entertain!

2641 Carvell Court, Winter Park
$439,000
3 Beds ⋅ 2 Baths ⋅ O6431278 MLS
Virtually Staged. This is the one!! Welcome home to this beautifully updated 3-bedroom, 2-bath POOL HOME with NO HOA!! RECENT MAJOR IMPROVEMENTS include a durable 2022 metal roof, a 2023 whole-house repipe, a 2023 A/C system, 2023 hot water heater, a 2022 pool filter, and a 2021 pool pump. Additionally the windows were replaced in approximately 2012 and the electric panel was replaced in 2011/2012. Inside, the RENOVATED KITCHEN is literally at the heart of the home and features stainless-steel appliances, granite counters, solid wood soft-close cabinetry and a farmhouse sink looking out to the pool area. Luxury vinyl plank flooring enhances the main living areas and BRAND NEW carpet adds comfort to the bedrooms. Both bathrooms have been UPDATED and the guest bathroom has been fitted with a walk-in accessible Jacuzzi tub. The freshly painted exterior provides attractive curb appeal. Step outside to your FULLY FENCED private backyard and swimming pool...perfect for relaxing, entertaining, and enjoying the Florida lifestyle. A storage shed is also included. Located in Seminole County with a desirable Winter Park address, the home is convenient to shopping, dining, parks, Full Sail University, UCF, SR 417, and Aloma Avenue. It is zoned for TOP RATED Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High School. With major improvements already completed, this inviting pool home is ready for its next owner. Schedule your showing today!!

7640 Village Green Dr, Winter Park
$189,900
2 Beds ⋅ 2 Baths ⋅ O6433680 MLS ⋅ 24 BLDG.
This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens directly to a generous private balcony—perfect for relaxing or unwinding after a long day. Ideally located just 15 minutes or less from UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes from Orlando International Airport. Whether you’re a first-time homebuyer, student, investor, or looking to make your move into Winter Park, this home delivers affordability, convenience, and excellent potential.

7468 Canford Court Unit 24, Winter Park
$499,000
4 Beds ⋅ 2 Baths ⋅ O6433521 MLS
Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a functional kitchen, with a shared laundry room equipped with a washer and dryer for added convenience. Both units include a full bath with updated showers. Enjoy all of Downtown Winter Park, including the shops and restaurants along Park Avenue, Winter Park Village, and an abundance of entertainment and recreational options such as Mead Botanical Garden, Winter Park Tennis Center, Winter Park Golf Course, and much more. The property also offers easy access to major highways and is just minutes from Rollins College. Don't miss this opportunity to own an income-producing property in one of Central Florida's most desirable areas with no HOA. Pictures were taken prior to occupancy.

2183 Crandon Avenue, Winter Park
$770,000
4 Beds ⋅ 3 Baths ⋅ O6426548 MLS
Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sought-after gated community of Hawk’s Crest. This former Meritage model home sits on a premium corner lot just steps from the clubhouse and resort-style amenities, and is one of the few corner homes in the community permitted to have a private fenced backyard. With more than 2,100 square feet of thoughtfully designed, energy-efficient living space, the home showcases an impressive collection of upgrades and finishes selected to highlight the best Hawk’s Crest has to offer. From the moment you enter, high ceilings and an inviting entryway set the tone. As a former model, the home features upgraded interior doors, cabinetry, baseboards, bathroom vanities, and custom details throughout. The expansive kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, granite countertops, double ovens, a walk-in pantry, stainless steel appliances, and a large center island with pendant lighting overlooking the living and dining spaces. The spacious owner’s suite offers a true retreat with an oversized walk-in closet and en-suite bath featuring dual vanities and a walk-in shower. Three additional bedrooms, two full bathrooms, and a generous laundry room with a utility sink and custom built-in drop zone provide plenty of space, storage, and everyday functionality. Outside, the covered lanai opens to a private fenced backyard surrounded by lush landscaping and complete with a fire pit, an ideal setting for entertaining, pets, or simply enjoying the outdoors. Hawk’s Crest residents enjoy an impressive collection of amenities including a resort-style pool, clubhouse, fitness center, splash pad, playgrounds, dog park, virtual guard gate, and access to Lake Howell. Former model home. Rare fenced corner lot. Extensive upgrades. And one of the shortest walks to the clubhouse in the entire community. This is an opportunity that truly stands apart in Hawk’s Crest.

2286 Marsh Sedge Lane, Winter Park
$669,000
2 Beds ⋅ 2 Baths ⋅ O6433393 MLS
LOCATION. LIFESTYLE. TIMELESS WINTER PARK CHARM. Discover an exceptional opportunity in Lake Knowles Terrace, where classic character, effortless comfort, and an enviable location come together beautifully. From the moment you arrive, the home makes an unforgettable first impression with charming curb appeal, elegant walkways, a brick-paver driveway, and a picturesque cobblestone brick road just off Palmer Avenue. Ideally positioned just one block from Lake Knowles and moments from Park Avenue, this residence offers the quintessential Winter Park lifestyle—peaceful, private, and exceptionally convenient. Step through the front door and into a light-filled, thoughtfully designed 2-bedroom, 1.5 bath residence offering approximately 1,100 square feet of comfortable living space. The inviting interior balances timeless charm with tasteful updates, creating a warm setting for both everyday living and entertaining. At the heart of the home, the beautifully updated kitchen features luxurious quartz countertops, stainless-steel appliances, abundant cabinetry, and generous storage, seamlessly opening to the family room. Sunlight pours through the windows, illuminating the space while a classic brick fireplace serves as a striking focal point, creating an inviting ambiance for cozy evenings and memorable gatherings. The home also offers a dedicated dining area and two comfortable bedrooms, complemented by a beautifully updated bathroom with stylish decorative finishes. Impeccably maintained throughout, the residence showcases wood flooring in the wet areas and an overall sense of care and refinement. The living experience continues outdoors, where the distinction between indoor and outdoor living nearly disappears. Step onto the newly constructed deck, pour a glass of wine, and unwind to the peaceful sounds of nature. The spacious homesite provides plenty of room for entertaining, outdoor games, a swing set, gardening, or simply enjoying the tranquility of your private surroundings. A versatile 16' x 11' detached laundry room, game room, or private retreat adds valuable flexibility and could easily serve as a home office, creative studio, fitness space, or ultimate man cave. Notable improvements include a new Trane HVAC system, interior and exterior units with air-duct cleaning, newer water heater, newer tile roof and decking (2021), updated electrical panel (2017), and beautifully maintained flooring. Surrounded by beautiful homes and nestled among tree-lined brick streets, this residence places you within easy reach of Park Avenue's celebrated dining, boutique shopping, cultural attractions, and vibrant charm. Enjoy a morning jog, leisurely bike ride, or golf-cart cruise to Park Avenue—all from a home tucked away in one of Winter Park's most desirable settings. A rare blend of character, comfort, and location—this is Winter Park living at its most inviting.

1409 Sunset Drive, Winter Park
$2,750,000
4 Beds ⋅ 5 Baths ⋅ O6433053 MLS
Virtually Staged. Beautifully updated and thoughtfully designed, this four-bedroom, three-and-one-half-bath residence blends sophisticated interiors, inviting living spaces and an impressive outdoor setting. Gorgeous curb appeal and meticulously maintained landscaping create a welcoming first impression, while extensive recent improvements bring a fresh, refined feel throughout. Just off the entry, a stately office/den with a wood-burning fireplace offers a handsome, versatile space for a home office, library or sitting room, while a formal dining room provides an elegant setting for entertaining. At the heart of the home is the beautifully updated kitchen, featuring new cabinetry and hardware, marble countertops and an expansive center island with generous seating. Luxury appliances include a striking induction range, integrated refrigerator and convenient beverage refrigeration drawer, while a dedicated coffee bar adds function and style. A sunny breakfast nook provides casual dining space, and the kitchen opens seamlessly to the spacious great room, where French doors lead to the covered lanai and fill the interiors with natural light. A cleverly concealed doorway in the kitchen provides access to the garage and a large bonus room above, complete with a custom wet bar and under-counter beverage refrigerator, an exceptional space for entertaining, recreation or media. Privately on the first floor, the primary suite offers direct access to the covered lanai, an ample custom walk-in closet and spa-inspired bath with dual vanities, soaking tub and glass-enclosed shower. A laundry room with custom cabinetry and powder bath with outdoor access complete the main level. Upstairs, a bright and spacious family room accompanies three additional bedrooms. One features a private en-suite bath, while the remaining two share a Jack-and-Jill bath. All closets feature custom organizational systems. Outdoor living is equally impressive. Accessible from the great room and primary suite, the covered lanai overlooks the newly refinished heated saltwater pool and spa, surrounded by new non-slip pool deck pavers. Wi-Fi-enabled pool and spa equipment provides convenient app-based control. Redesigned by Signature Landscape, the backyard features a turf area for loungers, dedicated firepit space and new fence installed in 2023, creating a wonderful setting for outdoor entertaining. A professionally installed Mist and More mosquito misting system adds another level of comfort, while a gas line from the street supplies the pool and firepit. Extensive upgrades include three HVAC systems installed in 2024 and 2025, a new water heater, whole-home water filtration system and Ecobee smart thermostats. The interior and exterior were repainted in 2025, complemented by new flooring, baseboards and crown molding, custom window treatments, wallpaper and carefully selected designer finishes. Interiors by nationally recognized designer Jaime Garnet of WYC Designs create a polished, cohesive aesthetic throughout. Ideally just minutes from downtown Winter Park, the home offers convenient access to exceptional dining, shopping and cultural amenities, along with major roadways for easy connectivity throughout Central Florida. With extensive updates, flexible living spaces, sophisticated interiors and a beautifully redesigned outdoor setting, this exceptional residence is move-in ready.

948 Poinciana Lane, Winter Park
$2,700,000
5 Beds ⋅ 5 Baths ⋅ O6430279 MLS
Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable pocket of Winter Park. A sophisticated modern farmhouse façade creates an impressive first impression, framed by a sweeping double-entry curved driveway that gives the home a commanding yet welcoming presence. Inside, the open-concept design is both polished and remarkably livable. A dedicated home office sits just off the entry, while the expansive main living space is anchored by a statement entertainment wall with an electric fireplace. Pocketing sliders disappear to create a seamless connection to the covered lanai and backyard, extending the home’s entertaining spaces outdoors. At the center of it all, the chef’s kitchen features Taj Mahal countertops, an oversized island, custom cabinetry, and a complete suite of Stainless steel appliances. A generous dining area and large walk-in pantry add to the home’s effortless functionality. One of the floor plan’s greatest advantages is the inclusion of two bedrooms on the main level, a rarity in Winter Park. The primary suite is particularly impressive, offering a true sense of retreat with a spa-inspired bath featuring dual vanities, a freestanding soaking tub, an oversized walk-in shower, and an expansive custom closet with a center island. The additional downstairs bedroom provides flexibility for guests or multigenerational living. Upstairs, three additional generously sized bedrooms are served by two full baths and a dedicated laundry room, along with an air-conditioned bonus room that easily functions as a sixth bedroom, theater, game room, or fitness studio. In all, the home offers five bedrooms, four and a half baths, a private office, and a climate-controlled bonus space, giving families room to spread out without compromise. The backyard was designed to feel like a private resort. A covered lanai and dedicated cabana with a full summer kitchen overlook the large pool and spa, while generous lawn space provides something increasingly difficult to find in newer Winter Park construction. Located minutes from Park Avenue's shops, cafes, and restaurants and close to Advent Health Winter Park, Cady Way Park, and the YMCA, this home offers an exceptional location. For those seeking new construction without compromising on space, location, or lifestyle, this is a Winter Park home that checks the boxes that matter.

648 Worthington Drive, Winter Park
$439,000
3 Beds ⋅ 2 Baths ⋅ O6433345 MLS
Nestled in Winter Park's Lake Bell Terrace neighborhood, this 3 bedroom, 2 bathroom home is located close to everything that makes Winter Park special, Park Avenue's shops and restaurants, Winter Park Village, Mead Botanical Garden, the Winter Park golf course, and more. Inside, an open, light-filled living area flows effortlessly into the kitchen and dining room, with wood and tile flooring throughout. A large bonus room adds flexible space for a home office, playroom, or media room, while the spacious bedrooms and abundant storage make everyday living easy. Outside, a classic front porch invites cozy mornings with coffee, a screened patio provides year-round outdoor living, and the beautiful backyard with additional open patio is perfect for grilling and gathering. A dedicated laundry/utility room and attached 1 car garage complete this Winter Park gem.

1955 Eland Avenue, Winter Park
$799,000
4 Beds ⋅ 3 Baths ⋅ O6432779 MLS
Rare Winter Park Opportunity | City-Approved 4,338 SF Buildable Area | R-2 Zoning | Detached Guest House Just a very short walk to Park Avenue, with restaurants, cafés, wine bars and boutiques within steps in virtually every direction, 950 S. Kentucky Avenue offers an exceptional combination of location, land, flexibility and future potential. Set on a 7,890-square-foot R-2 lot overlooking little Lake Midget and Park, the property allows for 4,338 square feet of buildable area, as approved by the City of Winter Park. The existing property is a charming mid-century residence on a brick-paved, tree-lined street. The block is distinguished by a mix of mature homes and beautiful new custom residences, including several striking modern homes that complement the neighborhood’s established character. The existing 2,155-square-foot home offers four bedrooms and three baths, including a detached one-bedroom, one-bath guest house with cabinetry already in place to complete a kitchenette. The detached guest house adds an unusual degree of versatility, whether used for guests, extended family, a private office or potential rental income. The current home can be enjoyed with some updating and improvements, allowing a new owner to take the time needed to create their ultimate vision. It features hardwood floors and distinctive historic crown molding salvaged from a Winter Park renovation. The kitchen overlooks the backyard and features a granite island and newer stainless appliances. A side entry from the tandem two-car carport leads into a practical mudroom with a tucked-away laundry closet. The spacious yard offers room for gardens, recreation, outdoor living and potentially a future pool. Recent improvements include a new roof in 2024, updated A/C in 2018, newer appliances and a transferable termite bond. Natural gas is available on-site. The location is truly special. Park Avenue and Central Park are a quick stroll away, while favorites including Croissant Gourmet, Ravenous Pig, Sushi Saint, Fiddler’s Green and Winter Park Playhouse are all within an easy walk. Rollins College, the Saturday Farmers Market, Hannibal Square and the many shops and restaurants of downtown Winter Park are also nearby. Families will also appreciate access to highly regarded Winter Park schools, including Audubon Park School (K–8) and Winter Park High School. Whether you choose to update and enjoy the existing home, use the guest house for additional flexibility or income, or ultimately create a new custom residence, 950 S. Kentucky Avenue offers a wonderful opportunity to live in the heart of Winter Park.

950 S Kentucky Avenue, Winter Park
$575,000
4 Beds ⋅ 3 Baths ⋅ O6433352 MLS
Welcome home to this beautifully presented 4-bedroom, 3-bath home located in Winter Park Estates. Offering a comfortable single-story layout and solid block construction, this home combines character, functionality, and inviting indoor and outdoor living spaces. Step inside to a spacious living area that flows naturally into the kitchen and adjoining living spaces, creating an excellent layout for everyday living and entertaining. One of the standout features is the private in-ground pool, creating a wonderful backyard setting for relaxing, entertaining, and enjoying Florida's year round outdoor lifestyle. The property also offers an attached garage, additional storage, and a functional layout designed to make the most of the home's space. Located in an established Winter Park neighborhood with no HOA, this property offers added flexibility without monthly association fees. The location provides convenient access to shopping, dining, parks, entertainment, and major roadways throughout Winter Park and the greater Orlando area. With its 4-bedroom, 3-bath layout, private pool, block construction, and desirable Winter Park location, this home offers a combination of space, convenience, and Florida living that is difficult to find.

2627 Ambergate Road, Winter Park