Winter Park, FL Houses for Sale

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  /42

  $875,000 Open Tue 4PM - 7PM

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1090 Wildmeadow Run, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. This luxurious Modern Style home delivers the pinnacle lifestyle, in every aspect of MAINTENANCE FREE LIVING. You will enjoy premium views of nature with a RESORT CLUBHOUSE featuring an abundance of amenities including a resort pool, fitness center & playground, all JUST 250 FEET AWAY....This home has been IMPECCABLY MAINTAINED, and includes the

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 339-2639

  1090 Wildmeadow Run, Winter Park, FL 32792
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  /44

  $729,000

  • 4 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  607 Dunblane Dr, Winter Park, FL 32792

  Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue’s top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunning chef’s kitchen with quartz waterfall countertops, custom cabinetry, and all-new stainless steel

  

  Khozaif Merali

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 490-4706

  607 Dunblane Dr, Winter Park, FL 32792
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  /18

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,637 Sq Ft

  1050 Reading Ct, Winter Park, FL 32792

  Great investment opportunity in the prime location of Winter Park, Florida. Ideal for a growing family or investor. Well established neighborhood of Howell Estates, 3 bedroom, 2 full bathrooms, 1,637 square feet of living area with just over a quarter of an acre. Split plan bedrooms for added privacy. Exterior of the home is concrete block and stucco. The eat-in-kitchen and large family room

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 850-2823

  1050 Reading Ct, Winter Park, FL 32792
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  /89

  $1,000,000

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  4107 Gabriella Ln, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Do you have a vision? Do you love Nature? Welcome to this Exceptional Bear Gully Lakefront Retreat – A Rare Blend of Privacy and Natural Beauty! Refurbish the house as it is, or start new on this amazing rare natural Florida lakefront ground. Tucked away on the serene shores of Bear Gully Lake, this one-of-a-kind property presents a rare

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 382-1061

  4107 Gabriella Ln, Winter Park, FL 32792
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  /42

  $765,000

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  2418 Whitehall Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION! MOTIVATED SELLER! Don't miss out!!! A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story property in the heart of WINTER PARK. Showcasing a new meticulously designed floorplan, this property has also recently been EXTENDED by a total approx. 1,040 sqft. Exuding

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (321) 599-7240

  2418 Whitehall Cir, Winter Park, FL 32792
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  /100

  $8,500,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,564 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 4/30/2025!! Introducing a Unique, Stunning Modern HomeA groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this home follows commercial-grade

  

  Prescilla Vazquez

  PV LUXURY GROUP PA

  (321) 478-2671

  2661 Vía Tuscany, Winter Park, FL 32789
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  /32

  $470,000

  • 5 Beds
  • 3 Baths
  • 1,442 Sq Ft

  2181 Linden Rd, Winter Park, FL 32792

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  Alejandro Rodriguez AROD PARTNERS REALTY

  2181 Linden Rd, Winter Park, FL 32792
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  /19

  $529,900

  • 3 Beds
  • 2 Baths
  • 2,254 Sq Ft

  7682 Glenmoor Ln, Winter Park, FL 32792

  Welcome to 7682 Glenmoor Lane – a beautifully renovated gem in the sought-after Glenmoor community of Winter Park. Situated on a generous 0.26-acre lot, this stunning single-family home blends timeless style with modern updates throughout.Step inside to discover custom tile flooring, solid wood cabinetry in both the kitchen and bathrooms, and custom tile work that adds elegance to every

  Bob Holston, Jr HOLSTON PROPERTIES & DEV., INC

  7682 Glenmoor Ln, Winter Park, FL 32792
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  /58

  $382,500

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft

  5234 Ohio St, Winter Park, FL 32792

  Tropical Vibes + Total Privacy in Winter Park! A rare find, indeed!! Tucked away at the very end of a quiet cul-de-sac, this charming block construction home offers the ultimate in peaceful vibes, comfort, and Florida living. Built in 1973, this one-story gem offers timeless durability with the added benefit of modern comfort and unmatched privacy. Set on a beautifully landscaped,

  Emily Nickley MARKET CONNECT REALTY LLC

  5234 Ohio St, Winter Park, FL 32792
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  /29

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  2006 Ponderosa Ave, Winter Park, FL 32792

  Pure Potential in Winter Park’s Eastbrook Community! Renovate or move-in, this is a great opportunity for an investor or homebuyer. Spacious 1,467 SF home with 3 bedrooms, 2 full baths, living & family room + a home office/den which could easily be converted into a 4th bedroom. New carpet in each bedroom. Fresh paint throughout. Attached 2-car garage with laundry. Custom built shed has plenty of

  Kelly Price KELLY PRICE & COMPANY LLC

  2006 Ponderosa Ave, Winter Park, FL 32792
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  /41

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  5331 Oak Ct, Winter Park, FL 32792

  Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

  Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

  5331 Oak Ct, Winter Park, FL 32792
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  /49

  $649,900

  • 3 Beds
  • 2 Baths
  • 1,469 Sq Ft

  1926 Natalen Rd, Winter Park, FL 32792

  *** MUST SEE WINTER PARK POOL HOME ***Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing

  Peggy Bonnewitz EXP REALTY LLC

  1926 Natalen Rd, Winter Park, FL 32792
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  /54

  $3,544,999

  • 5 Beds
  • 5.5 Baths
  • 4,955 Sq Ft

  1761 Legion Dr, Winter Park, FL 32789

  One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

  Brian Scanlon SCANLON REALTY GROUP LLC

  1761 Legion Dr, Winter Park, FL 32789
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  /80

  $1,210,000

  • 4 Beds
  • 3.5 Baths
  • 3,321 Sq Ft

  4048 Gilder Rose Place, Winter Park, FL 32792

  Welcome to 4048 Gilder Rose Pl, an impressive four-bedroom, three and a half bathroom residence spanning over 3,300 square feet, located in Winter Park at Bear Gully Pointe, a gated community featuring a spring fed 137 acre lake. This beautifully updated home perfectly balances modern style with practical living, offering an inviting retreat for those seeking both comfort, sophistication and

  Abby Greenberg COMPASS FLORIDA LLC

  4048 Gilder Rose Place, Winter Park, FL 32792
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  $2,900,000

  • 4 Beds
  • 7 Baths
  • 5,416 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open interior, situated on a spacious corner lot just moments from Park Avenue. From the moment you step into the grand foyer—with its graceful circular staircase, custom tile work, and rich wood floors—it's clear that every detail of this home was crafted with care.The heart of

  Terry Yonker BUCKEYE REALTY LLC

  1401 Green Cove Rd, Winter Park, FL 32789
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  /66

  $1,249,000

  • 3 Beds
  • 2.5 Baths
  • 1,993 Sq Ft

  2525 Venetian Way, Winter Park, FL 32789

  Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake Access This meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas fireplace. The sleek, chef-inspired kitchen

  Kimberly Slinger KELLY PRICE & COMPANY LLC

  2525 Venetian Way, Winter Park, FL 32789
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  /85

  $1,590,000

  • 5 Beds
  • 4.5 Baths
  • 5,329 Sq Ft

  8041 Lake Waunatta Dr, Winter Park, FL 32792

  Modern Lakefront Dream home NOW AVAILABLE! Nestled in the peaceful Lake Waunatta Woods neighborhood, this stunning renovated lakefront estate seamlessly blends modern style with effortless luxury. With over 5,300 square feet, five spacious bedrooms, and breathtaking panoramic views of Lake Waunatta from nearly every room, this one-of-a-kind property offers the ultimate waterfront lifestyle.

  Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

  8041 Lake Waunatta Dr, Winter Park, FL 32792
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  /48

  $2,150,000

  • 5 Beds
  • 4.5 Baths
  • 3,851 Sq Ft

  1560 Woodland Ave, Winter Park, FL 32789

  You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick-paved street. There are five bedrooms and four and a half bathrooms spread out over 3,800 square feet in this stunning property. Featuring a welcoming pool and relaxing spa. A separate suite with its own entrance is available for use by the mother-in-law

  Manny Alvarez LOKATION

  1560 Woodland Ave, Winter Park, FL 32789
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  /44

  $440,000

  • 4 Beds
  • 2 Baths
  • 1,821 Sq Ft

  2829 Aloma Ave, Winter Park, FL 32792

  Rare Opportunity in Highly Sought-After Winter Park!Don’t miss your chance to own this fantastic 1960s gem in one of Winter Park’s most desirable neighborhoods just minutes to Cady Way Trail, and tons of Dining and shopping options! SELLER WILL CONTRIBUTE 10K to your closing costs.. AND ...LISTED WELL BELOW APPRAISED VALUE ! Known for its top-rated schools and unbeatable location as well , this

  Cassie Lamoureux KELLER WILLIAMS CLASSIC

  2829 Aloma Ave, Winter Park, FL 32792
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  /72

  $539,500

  • 5 Beds
  • 2 Baths
  • 2,272 Sq Ft

  5073 Lake Howell Rd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Discover this large 5-bedroom, 2-bathroom POOL home in an established Winter Park neighborhood with no HOA! A fantastic opportunity for new owners to bring their personal design touches and upgrades. Plenty of room to take down walls and really open this home up to it's full potential. Recent Major improvements include: NEW ROOF (2021), NEW AC

  Susie Norton CHARLES RUTENBERG REALTY ORLANDO

  5073 Lake Howell Rd, Winter Park, FL 32792
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  /35

  $784,000

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft

  5618 Winterbrook Way, Winter Park, FL 32792

  This stunning 5-bed, 4-bath home in the exclusive gated WINTERBROOK community is move in ready and ready for you to enjoy. Built in 2020 by Pulte Homes, this like new energy-efficient home offers luxury wood-look tile, wood beams, a 2 car garage with epoxy floors and a beautifully landscaped backyard. The gourmet kitchen features quartzite countertops, a gas cooktop, upgraded sink, and large

  Elizabeth Binder REDFIN CORPORATION

  5618 Winterbrook Way, Winter Park, FL 32792
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  /31

  $1,490,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,838 Sq Ft

  2408 Lafayette Ave, Winter Park, FL 32789

  This brand new custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set

  Matthew Burks CORCORAN PREMIER REALTY

  2408 Lafayette Ave, Winter Park, FL 32789
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  /32

  $899,000

  • 5 Beds
  • 4 Baths
  • 3,424 Sq Ft

  2604 Marble Ave, Orlando, FL 32803

  Stunning 5 BEDROOM POOL HOME in the Heart of AUDUBON PARK GARDEN DISTRICT. Welcome to 2604 Marble Avenue — a beautifully appointed 5-bedroom, 4-bathroom home offering 3,424 SQUARE FEET of stylish living space in one of Orlando's most desirable neighborhoods. Zoned for top-rated AUDUBON PARK K-8 and WINTER PARK HIGH SCHOOL, this home combines location, comfort, and exceptional versatility.

  Brian Spain LAKESIDE REALTY

  2604 Marble Ave, Orlando, FL 32803
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  /25

  $1,150,000

  • 5 Beds
  • 3 Baths
  • 2,813 Sq Ft

  233 Hampden Place, Winter Park, FL 32789

  Vintage original 5-Bed, 3-Bath pool home with new roof on an estate-size lot adorned with mature landscaping and breathtaking views that overlook a natural wooded area in desirable Virginia Heights. This fabulous property could have a full renovation to make best use of the existing home, or the 16,000+ square foot lot offers the perfect opportunity to build the new home of your dreams and

  Frank Ferrell FERRELL REALTY, INC.

  233 Hampden Place, Winter Park, FL 32789
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  /55

  $1,050,000

  • 4 Beds
  • 3.5 Baths
  • 2,173 Sq Ft

  208 Brewer Ave, Winter Park, FL 32789

  Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering just under 2,200 sq ft of thoughtfully designed living space. From the moment you arrive, the charm is undeniable—with classic architectural details and a welcoming front porch that set the tone for what’s inside. Step into an open and inviting layout featuring an updated kitchen with modern cabinetry,

  Cassandra King COMPASS FLORIDA LLC

  208 Brewer Ave, Winter Park, FL 32789
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  /50

  $1,349,500 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft

  1371 Lyndale Blvd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. As you enter this renovated 4-bedroom, 2.5-bathroom home within the city limits of Winter Park, you're immediately welcomed by a bright, open living and dining area anchored by a stunning wet bar, complete with sink, cabinetry, ice maker, and floating shelves. All completed with light modern porcelain tile flooring. To your right, the kitchen

  Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
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  /34

  $845,000

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  734 Maryland Ave, Winter Park, FL 32789

  Fully renovated 1926 historic Winter Park bungalow with separate guest cottage in the heart of the Winter Park Historic District. Surrounded by a beautiful tree-lined street with brick roads, you'll be impressed by the magnificent curb appeal. Ideally located within a short distance to Park Avenue, Rollins College and the Winter Park Chain of Lakes community dock, just minutes from the Winter

  Michael Domi PREMIER SOTHEBY'S INTL. REALTY

  734 Maryland Ave, Winter Park, FL 32789
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  /41

  $1,200,000

  • 6 Beds
  • 4 Baths
  • 4,277 Sq Ft

  2080 Wood Thrush Ln, Winter Park, FL 32792

  Exceptional Living Awaits in the Heart of Winter ParkNestled in the sought-after community of Waters Edge at Hawks Crest, this stunning4268 square-foot energy-efficient home offers an exquisite blend of classic eleganceand modern comfort. This Kerville II model, built by Meritage Homes in 2020, has beenthoughtfully designed to be both welcoming and refined.From the moment you

  Nate Klutznick LOKATION

  2080 Wood Thrush Ln, Winter Park, FL 32792
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  /74

  $1,750,000

  • 3 Beds
  • 4 Baths
  • 2,964 Sq Ft

  1270 Arlington Place, Winter Park, FL 32789

  Modern Elegance in the Heart of Winter Park!Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this home reflects exceptional craftsmanship and elevated taste.A long paver driveway welcomes

  Brian Mitnik RE/MAX 200 REALTY

  1270 Arlington Place, Winter Park, FL 32789
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  /38

  $1,425,000

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  2015 Summerfield Rd, Winter Park, FL 32792

  In the heart of Kenilworth Shores, one of Winter Park’s desirable neighborhoods, this completely renovated one-story residence offers a blend of modern luxury and effortless livability. Meticulously reimagined in 2024, every detail of this home has been thoughtfully curated—from the clean-lined architectural finishes to the flowing, open-concept layout that seamlessly connects indoor and outdoor

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2015 Summerfield Rd, Winter Park, FL 32792
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  /21

  $949,900

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  2823 Wright Ave, Winter Park, FL 32789

  Here’s your chance to own something truly special in Winter Park! This gorgeous lakefront home sits on over HALF AN ACRE, a rare find in this area - allowing opportunity to BUILD YOUR DREAM HOME! Step inside to find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes, ideal for both entertaining and everyday living. The home boasts new windows

  Tal Busidan TAL BUSIDAN PA

  2823 Wright Ave, Winter Park, FL 32789
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  /23

  $998,000

  • 4 Beds
  • 3.5 Baths
  • 4,088 Sq Ft

  1319 Heavenly Cove, Winter Park, FL 32792

  FULLY FURNISHED HOME THAT IS MOVE-IN READY! ALL FURNITURE INCLUDED IN THE SALES PRICE! Amazing home located in a quiet gated subdivision in Winter Park near Trinity Prep. The home provides a wonderful layout with high ceilings and an open concept – perfect for entertaining. Updated kitchen with clean white cabinets, spacious chef’s island, and GE stainless steel appliances to cook a delicious

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  1319 Heavenly Cove, Winter Park, FL 32792
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  /39

  $900,000

  • 4 Beds
  • 2 Baths
  • 2,237 Sq Ft

  1018 Turner Rd, Winter Park, FL 32789

  Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat lift, character and contemporary upgrades that make everyday feel like a lakeside retreat. Major

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1018 Turner Rd, Winter Park, FL 32789
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  /72

  $1,095,000

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft

  2607 Lafayette Ave, Winter Park, FL 32789

  Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining.Step inside to discover an open-concept layout that seamlessly connects the kitchen,

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2607 Lafayette Ave, Winter Park, FL 32789
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  /39

  $950,000

  • 4 Beds
  • 4 Baths
  • 3,646 Sq Ft

  5510 Howell Branch Rd, Winter Park, FL 32792

  Welcome to an extraordinary Florida residence, situated on a sprawling 1.52-acre lot. The main residence features an attached two-car garage, complemented by a detached two-car garage—perfect for additional vehicles or workshop space. For those in need of versatile storage or business potential, a 3,500-square-foot two-story warehouse offers ample opportunity, while a spacious outdoor

  Shaun Shaffner Blue Marlin Real Estate

  5510 Howell Branch Rd, Winter Park, FL 32792
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  /72

  $825,000

  • 5 Beds
  • 3 Baths
  • 2,132 Sq Ft

  730 W Swoope Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Experience the Charm of Winter Park in This Renovated Corner HomeWelcome to the beautifully updated gem of Winter Park!Located on a prime corner lot just three short blocks from the famous Park Avenue, this stunning residence spans over 2,200 square feet and has been completely transformed to blend style, comfort, and an unbeatable

  Andres Ospina Rivera LPT REALTY, LLC

  730 W Swoope Ave, Winter Park, FL 32789
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  /38

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,887 Sq Ft

  913 Moss Ln, Winter Park, FL 32789

  ***Lease purchase available | Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Moss Lane, Winter Park, FL – A 2023 Masterpiece Awaits! Step into luxury living at 913 Moss Lane, a breathtakingly renovated 3-bedroom, 2-bath haven in the heart of Winter Park, boasting 1,887 square feet of modern elegance and timeless Florida charm.

  Peter Rodriguez VECTOR PROPERTY GROUP

  913 Moss Ln, Winter Park, FL 32789
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  /65

  $935,000

  • 5 Beds
  • 3.5 Baths
  • 3,598 Sq Ft

  5325 Cypress Reserve Place, Winter Park, FL 32792

  ATENTION BUYERS!! PRICE ADJUSTED TO $935K & $15K SELLER CONCESSION TOWARDS BUYERS CLOSING COST WITH FULL ASKING PRICE!!Your Dream Home Awaits!Imagine a home that blends luxury, comfort, & convenience that’s exactly what you’ll find at 5325 Cypress Reserve Pl in Winter Park’s exclusive gated community Cypress Reserve.This move-in-ready 5-bedroom masterpiece isn’t just a house

  Dori Estrada LPT REALTY, LLC

  5325 Cypress Reserve Place, Winter Park, FL 32792
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  /68

  $960,000

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft

  250 Cortland Ave, Winter Park, FL 32789

  Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

  Alexandra Nordine EXP REALTY LLC

  250 Cortland Ave, Winter Park, FL 32789
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  /57

  $1,070,000

  • 4 Beds
  • 2.5 Baths
  • 3,121 Sq Ft

  1444 Pelican Bay Trail, Winter Park, FL 32792

  Back on market due to financing issue with buyer. Updated Price! A True Gem on the Lake!If you've been dreaming of owning a lakefront property with a Winter Park address, this is your chance! This stunning 4-bedroom, 2.5-bathroom home in the tranquil Pelican Bay Subdivision is move-in ready and full of charm.As you approach, you'll be greeted by lush landscaping. Step

  Jacob Hara TRANSCEND REALTY

  1444 Pelican Bay Trail, Winter Park, FL 32792

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Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Learn more about living in Winter Park

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 95 days on the market compared to the national average of 70 days. The median sale price for homes in Winter Park, FL over the last 12 months is $450,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$450,000

Median Single Family Sale Price

$810,000

Median Townhouse Sale Price

$775,000

Median 2 Bedroom Sale Price

$170,000

Median 1 Bedroom Sale Price

$149,000

Average Price Per Sq Ft

$339

Number of Homes for Sale

29

Last 12 months Home Sales

174

Months of Supply

2.00

Median List Price

$630,000

Median Change From 1st List Price

6%

Median Home Sale Price YoY Change

1%