Winter Park Real Estate Search

Winter Park Homes for Sale

Our website features the best Winter Park real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Winter Park Homes and Condos for Sale

$397,000
3 Beds 2 Baths Eastbrook Sub SubDv. 32792 Zip Code
Step through the door, take a deep breath, and know that you are finally where you are supposed to be in this delightful Winter Park home! This 3 bedroom, 2 bath with open-concept floor plan is situated in the desired EASTBROOK community. The open family/kitchen/dinette exudes a sense of spaciousness as you enter through the front door. The kitchen features GRANITE countertops, STAINLESS STEEL APPLIANCES and a kitchen island offering additional cabinet space. When you prefer a more private place to relax, the separate living room with BRICK FIREPLACE and additional mini split offers that tranquillity year-round with a door leading to your own large PATIO with an outdoor shower. As you walk down the hall to the primary bedroom featuring an EN-SUITE BATHROOM with GRANITE countertops and a large WALK-IN CLOSET with bifold doors, you pass 2 additional bedrooms and an upgraded guest bathroom. The covered one-car CARPORT also boasts an exterior LAUNDRY ROOM with washer/dryer hook up and additional storage area with shelving, convenient for all your outdoor gear. The EXPANSIVE back yard is surrounded by privacy fencing and mature landscaping with a storage shed as well. Zoned for high-rated Winter Park schools, this home is also conveniently located to all Orlando and its surrounding areas have to offer: Downtown Orlando, Downtown Winter Park, theme parks, golf courses, Rollins College, University of Central Florida and numerous retail shops and restaurants. Come see this home today and make it yours!

3676 Hedgewood Drive, Winter Park

$3,095,000
5 Beds 5.5 Baths Comstock Park SubDv. 32789 Zip Code
Welcome to 1563 Lakehurst, a stunning 5-bedroom, 5-and-a-half-bathroom pool home that epitomizes luxury living and has been meticulously remodeled to perfection. This residence won the prestigious Orlando Parade of Homes 2021 First Place and Grand Award and is a masterpiece of design and craftsmanship.Initially conceived by the local architect Gary Hancock, this home was reimagined by the renowned Ted Maines and Hardwick General Contractors, resulting in a comfortably elegant living space deserving of accolades and awards. Located on an oversized lot on a charming brick-lined street in one of the most desirable neighborhoods of Central Florida, this home boasts an enviable address just moments away from the shops and restaurants of Winter Park and Park Ave. Spanning over 4,300 square feet, the main house offers spacious and inviting living areas flooded with natural light. Every detail was considered throughout the renovation: top-of-the-line Anderson windows, custom inset cabinetry, luxury bi-fold Origin door, designer lighting, engineered oak floors, solid core interior doors, custom mahogany front door, and many more finishes that discerning buyers will recognize and appreciate. The kitchen is the heart of the home, featuring Wolf and Sub-Zero appliances, extensive custom inset cabinetry, Cambria luxury quartz, and a center island spanning almost 20 feet. The separate breakfast bar allows quick and easy coffee, tea, and breakfast prep without disturbing the clean aesthetics of the kitchen. The open living space has an Origin Luxury bi-fold door for indoor-outdoor living, and a vaulted cathedral ceiling finished with designer lighting. The lounge and bar offer a pre-dinner retreat before using the artfully designed formal dining room, with smoked glass, dramatic navy wood paneling, and custom herringbone wood floor. The light-filled primary bedroom is also located on the ground floor. Updated in 2022, this bedroom has Phillip Jeffries wall covering and Flos pendants. The bathroom has two independent vanities and separate closets. A full pool bathroom with shower, additional powder room and large office or flexible space complete the first story. Three additional bedrooms provide ample space for family or guests. The largest bedroom has an ensuite bathroom, and two additional bedrooms are connected by a large bathroom with a double vanity. For those needing additional accommodations, the in-law suite over the garage offers an additional 400+ square feet of living space, perfect for guests or multigenerational living. The extensive back patio has multiple areas for dining, entertaining, and enjoying Florida living. The summer kitchen was installed in 2021, and there is additional wine and refrigeration space. The front parking pad and landscaping were completed in spring 2024.All of the systems are from 2020 or newer. The roof was installed in 2020, 2 tankless water heaters were added in 2020, upstairs and downstairs Carrier air conditioners are from 2023, the guest house a/c is from 2021, and the guest house water heater is from 2024. All drywall, ceilings and tongue and groove was replaced, home was taken down to the studs, and has an effective date for build as 2020. With its unparalleled location, luxury, and craftsmanship, this home is a rare find. Don't miss your opportunity to own a piece of Winter Park's finest—schedule your private showing today!

1563 Lakehurst Avenue, Winter Park

$625,000
4 Beds 3 Baths Glencoe Sub SubDv. 32789 Zip Code
Welcome to your dream home in the heart of Winter Park's Glencoe subdivision, where luxury meets convenience with NO HOA fees! This meticulously renovated and updated 4-bedroom, 3-bathroom residence sits majestically on over a quarter-acre lot, offering a sanctuary of modern comfort and style. From the moment you arrive, the curb appeal beckons with its custom pavers driveway and a detached 1-car garage, providing both parking convenience and additional storage space. Step inside to discover a harmonious blend of contemporary design and functionality, highlighted by brand-new AC, roof, water heater, appliances & septic tank. The interior welcomes you with matching vinyl flooring that flows seamlessly throughout the open floor plan, encompassing the living room, dining area, and kitchen. Natural light floods the space, accentuated by large windows and a back double sliding glass door leading to the expansive backyard. The kitchen is a chef's paradise, boasting brand new stainless steel appliances, elegant white cabinetry with gold accents, luxurious marble countertops, and a stunning tile backsplash. A massive center island serves as the focal point, ideal for effortless meal preparation and entertaining guests. Retreat to the master bedroom, where tranquility awaits with an attached master bathroom and a spacious walk-in closet. The master bathroom exudes opulence with a double sink vanity and a massive walk-in shower, complemented by matching white cabinetry, countertops, and chic black and gold accents echoing the home's sophisticated theme. Additional bedrooms offer ample space, natural light, and versatility, providing ideal accommodations for family members or guests. Step outside through the kitchen to the oversized backyard, a sprawling oasis perfect for hosting family gatherings, celebrating holidays, or simply unwinding in solitude. This exceptional property not only offers unparalleled comfort and style but also boasts an unbeatable location close to major roads, highways, restaurants, entertainment, and more. Don't miss your chance to make this unique residence your own! <div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=o8FGEvVwB7G&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

2710 Euston Road, Winter Park

$639,900
3 Beds 2.5 Baths Villas Of Aragon Condo SubDv. 32789 Zip Code
Welcome to easy living in Winter Park! Step into this charming townhouse nestled in the Villas of Aragon. With just 4 townhouses in the neighborhood, connected solely by the garage, you'll enjoy a secluded setting. On the first floor, discover a delightful kitchen boasting timeless white cabinets, granite countertops, stainless-steel appliances, a large breakfast bar, and a charming tongue and groove ceiling which adds a touch of character to this heart of the home. Enjoy meals in the spacious dining room, illuminated by natural light streaming through French doors leading to the courtyard. The dining room seamlessly flows into the inviting living room, adorned with a stunning white brick wood-burning fireplace and elegant plantation shutters. Throughout the home, you'll find gorgeous bamboo flooring adding warmth and sophistication. The first floor is complete with a chic powder bath for guests and a cozy desk nook tucked under the stairs. Upstairs, the large primary bedroom awaits with ample natural light, pitched ceilings, and a rustic barn door leading to the ensuite bathroom. Pamper yourself in the primary bathroom boasting double vanities, a large shower, and two walk-in closets. Two additional generously sized bedrooms share a beautifully renovated secondary bathroom. Step outside to the back patio and bask in the beauty that surrounds you. A pergola adorned with stunning jasmine vines creates a picturesque scene, while fern pine trees offer both elegance and privacy. With an oversized two-car garage, a parking pad for guests, and a low HOA fee of only $400/month, this townhouse offers both convenience and exceptional value. Other highlights include a new roof installed in 2021, a new AC unit in 2022, and fresh exterior and interior paint. Located centrally in Winter Park, this property provides easy access to all major roads and highways. Plus, it's just minutes away from Downtown Winter Park's renowned Park Avenue shopping and dining. Don't miss out on this fabulous opportunity to call this townhouse your home sweet home!

1051 Aragon Avenue Unit 1051, Winter Park

$635,000
3 Beds 2 Baths Orangewood Park SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. Welcome home to this well maintained 3-bedroom 2-bathroom home right in the heart of Winter Park. The location is phenomenal - walking distance to East End Market, a short bike ride to Baldwin Park, Ivanhoe Village, or esteemed Park Avenue. While the area boasts an endless list of places to visit you will also enjoy the quiet, oak tree lined streets of his highly sought after Eastern Parkway address as you are welcomed with lush landscaping surrounding the bungalow style home. This home boasts a separate dining area off the living room, with a breakfast nook located off the kitchen. The stunning wood floors lead you back to a primary suite that includes a spacious walk-in closet with custom built-ins and an entry room perfect for an office, sitting area, baby’s room, or anything in between. You will also find 2 bedrooms and a fully renovated bathroom as you continue down the hallway. Florida living at its finest is found on the newly installed patio located in the oversized backyard. Enjoy a completely fenced in backyard with room for BBQ, games, and the perfect place for hosting. The backyard also includes a shed for extra storage. Extra features and updates include: new HVAC 2018, re-piped interior, no cast iron (rare), Roof 2017, replaced well pump for irrigation (low waste water and sewer bills), renovated patio, updated landscape, and renovated guest bathroom.

2817 Eastern Parkway, Winter Park

$1,550,000
3 Beds 3.5 Baths Winter Park Residential SubDv. 32789 Zip Code
Step into luxury living at its finest in this exquisite two-story condo nestled within the Douglas Grand of downtown Winter Park. Boasting sophistication and elegance and offering unparalleled comfort and convenience. Spanning across two levels on the North side of the building (more energy efficient), this residence features 3 bedrooms (2 owners suites… one on main level and one up), 3 1/2 baths, and a “private interior elevator”, ensuring effortless access and seamless transitions between spaces. The bright-open floor plan is ideal for both entertaining and everyday living, highlighted by a spacious kitchen equipped with top-of-the-line Sub-Zero, Bosch, and Wolf appliances, complemented by custom cabinetry for a touch of refinement. Indulge in the serenity of the interior atrium, creating a tranquil oasis of natural light within the comfort of your own home. Each bedroom is accompanied by its own ensuite bath and walk-in closet, providing ultimate privacy and convenience. The primary suite is a sanctuary of relaxation, offering a generous 25 x 13 layout, a large walk-in closet, and access to the outdoor terrace with a tree-top view overlooking Morse Boulevard - perfect for a morning coffee or evening wine. Convenience meets luxury with two deeded parking spaces within the secured parking garage, ensuring peace of mind and ease of access. There is plenty of additional common area parking as well separate from the gated off owner’s parking area… Located in the heart of downtown Winter Park, Douglas Grand offers unrivaled access to renowned Park Avenue, Winter Park Farmer's Market, Central Park, Winter Park Village, and Rollins College, placing an array of dining, shopping, and entertainment options only footsteps away. Embrace the lock-and-leave lifestyle with the SunRail station just a short stroll away, providing convenient access to downtown Orlando for sporting events or the Dr. Phillips Performing Arts Center. Whether you're seeking a serene retreat or a vibrant urban experience, this sophisticated condo offers the perfect blend of luxury, convenience, and elegance, promising a lifestyle of unparalleled comfort and style.

101 S New York Avenue Unit 304, Winter Park

$749,900
2 Beds 2 Baths Tax Equities Inc Rep SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Park! This completely renovated gem showcases a spacious layout with a modern farmhouse style, nestled in a classic, sought-after Central Florida neighborhood. As you step onto the covered front porch, you'll immediately feel the inviting atmosphere, perfect for unwinding and soaking in the tranquil neighborhood vibe. Inside, the open floorplan offers versatility to configure living spaces to your heart's desire. The kitchen is a chef's delight, boasting beautiful butcher block counters, a farmhouse sink, and a stylish tile backsplash. Equipped with stainless steel appliances, including a 6 burner gas stove, it's ready for culinary adventures. Retreat to the master bedroom, a peaceful haven at the end of the day. The ensuite master bath features a charming barn door entry, ample cabinet space in the vanity, and a luxurious partially framed glass enclosed shower with a standalone soaking tub. The secondary bedroom is equally inviting, with a vaulted ceiling and easy access to a beautiful full bath just outside its entrance. Step outside to the open patio overlooking the fenced backyard, offering a serene space to relax and enjoy the outdoors. Luxury vinyl plank floors flow seamlessly throughout the entire home, complementing the modern aesthetic. Every aspect of this home has been meticulously updated, from plumbing, electrical, and HVAC systems to windows, doors, and fixtures. Plus, plumbing is already in place for a future tankless hot water heater installation. The location couldn't be better, with easy access to Winter Park Village, Trader Joe’s, and Park Avenue, providing an endless array of dining and shopping options. Don't miss the opportunity to make this your forever home! Schedule a showing today and experience the epitome of Winter Park living. <iframe width='853' height='480' src='https://my.matterport.com/show/?m=dG1uYAKsj8u' frameborder='0' allowfullscreen allow='xr-spatial-tracking'></iframe>

840 W Canton Avenue, Winter Park

$320,000
2 Beds 2.5 Baths Vistas At Lake Howell SubDv. 32792 Zip Code
Discover the perfect blend of luxury and convenience in this beautifully updated two-bedroom townhouse located in the gated Vistas at Lake Howell community in desirable Winter Park. This property stands out with its modern amenities and strategic location, offering a lifestyle most can only dream of. The townhouse features a newly updated kitchen complete with new appliances and countertops, a master bath freshly painted, and updated outlet and switch covers, ensuring a contemporary feel throughout. Each bedroom boasts expansive walk-in closets, with the primary suite connected to a versatile loft area and an ensuite bathroom, enhancing both space and privacy. Enjoy the essence of open-concept living with a layout designed for both entertaining and relaxation. The spacious living area extends through large sliding doors to a screened and covered lanai, perfect for alfresco dining or quiet evenings enjoying the breeze. Positioned for ultimate convenience, this home is just minutes from Downtown Winter Park, UCF, Full Sail University, Rollins College, and Advent Health facilities. With an abundance of shopping, dining, and entertainment options nearby, everything you need is within easy reach. Residents benefit from thoughtful community features including extra guest parking, peaceful walkways, and professional lawn maintenance, which contribute to a carefree and low-maintenance lifestyle. Ready for immediate move-in, this townhouse combines comfort, style, and practicality, making it an ideal choice for discerning buyers or investors seeking a prime property in Winter Park.

2645 Galliano Circle, Winter Park

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