Winter Park Homes for Sale

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  /50

  $469,900

  • 3 Beds
  • 3 Baths
  • 1,880 Sq Ft

  2835 Bongart Rd, Winter Park, FL 32792

  Seller is Motivated and open to incentives, must sell NOW! - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard

  

  Claudia Jenkins

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 450-7314

  2835 Bongart Rd, Winter Park, FL 32792
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  Explore Winter Park

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  /15

  $189,900

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit B216, Winter Park, FL 32789

  Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaurants, schools and major roadways. The end unit features a nice open floorplan with lots of natural light. The kitchen is spacious and has lots of cabinet storage and countertop space it overlooks the large living room with sliding glass doors that lead out to the balcony with a

  

  Martha Grasty

  RE/MAX ASSURED

  (321) 381-3262

  1695 Lee Rd Unit B216, Winter Park, FL 32789
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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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  /28

  $649,900 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789

  Rare opportunity to own a first floor unit with soaring 9 foot ceilings only steps away from the prestegious Park Avenue! Discover the perfect blend of luxury, comfort, and convenience with this immaculate, move-in-ready condo, in the heart of Winter Park. Recently transformed with meticulous attention to detail, this lock-and-leave gem boasts an elegant, high-end renovation that exudes

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789
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  /24

  $100,000

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  126 Scottsdale Square Unit B126, Winter Park, FL 32792

  Great location!! Discover the charm of this beautifully maintained condo at 126 Scottsdale Square, nestled in a serene and convenient Orlando community. This condo boasts 3 bedrooms and 2 bathrooms thoughtfully designed with a spacious layout perfect for comfortable living. From the bright and open living area to the modern kitchen with upgraded appliances. Every detail has been tailored for

  Thomas Hicks, Sr LPT REALTY, LLC

  126 Scottsdale Square Unit B126, Winter Park, FL 32792
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  /38

  $875,000

  • 4 Beds
  • 4 Baths
  • 2,759 Sq Ft

  730 S Ranger Blvd, Winter Park, FL 32792

  Stunning, one of kind, 4/4 Winter Park pool home loaded with upgrades! ROOF, AC & WATER HEATER (2020), NEW FLOORING, KITCHEN & BATHS (2025), QUARTZ COUNTER TOPS (2025) FRESH INTERIOR PAINT (2025) & EXTERIOR (2023). Enjoy NEW DRIVEWAY PAVERS, FRONT YARD IRRIGATION (2025), REPLACEMENT WINDOWS & FRENCH DOORS (2016). Largest old school POOL in the neighborhood (20x40) RESURFACED (2016) with NEW PUMP

  David Knight EXP REALTY LLC

  730 S Ranger Blvd, Winter Park, FL 32792
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  /72

  $945,000

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  915 Garden Dr, Winter Park, FL 32789

  Step into this beautifully maintained Mid-Century Modern home, nestled in the prestigious Winter Park community and just a short three-minute stroll to the serene beauty of Mead Botanical Garden. A true raised ranch design, this home radiates warmth and character from the moment you arrive, featuring an expansive covered front patio that welcomes you inside.Inside, you’ll be greeted by

  Cassie Lamoureux KELLER WILLIAMS CLASSIC

  915 Garden Dr, Winter Park, FL 32789
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  /44

  $3,499,999

  • 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

  Kelly Price KELLY PRICE & COMPANY LLC

  1761 Legion Dr, Winter Park, FL 32789
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  /77

  $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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  /37

  $899,000

  • 3 Beds
  • 3.5 Baths
  • 2,116 Sq Ft

  1251 Arlington Place, Winter Park, FL 32789

  STUNNING WINTER PARK TOWNHOME - NO HOA, DESIGNER KITCHEN, PRIVATE BACKYARD OASISWelcome to this rare gem in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home WITH NO HOA! From the moment you walk in, you’ll be impressed by 20-FOOT CEILINGS in the foyer and family room, elegant hardwood floors, and OVERSIZED 8.5-FOOT DOORS

  Brad Barnett ANNE ROGERS REALTY GROUP INC

  1251 Arlington Place, Winter Park, FL 32789
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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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  /59

  $1,475,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  690 Osceola Ave Unit 604, Winter Park, FL 32789

  Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder’s unit with panoramic views of Lake Virginia from almost every room and its expansive full-width balcony. Welcome to Lakefront Luxury Living in the heart of Winter Park. This extraordinary Penthouse residence on the Chain of Lakes perfectly captures the essence of opulent Florida living. The 2-story lakefront home offers an

  Larry Slung COLDWELL BANKER RESIDENTIAL RE

  690 Osceola Ave Unit 604, Winter Park, FL 32789
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  /26

  $714,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,866 Sq Ft

  1275 Michigan Ave, Winter Park, FL 32789

  Welcome to this stunning townhome in the heart of Winter Park, built by award-winning Osprey Custom Home Builders. This residence combines timeless design, coastal aesthetic, certified greb construction, energy efficiency, and modern smart-home conveniences.Featuring 3 bedrooms, 2.5 baths, and an open-concept layout, the home is filled with designer finishes and thoughtful details

  Brandon Geers COMPASS FLORIDA LLC

  1275 Michigan Ave, Winter Park, FL 32789
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  /30

  $1,550,000

  • 5 Beds
  • 3 Baths
  • 3,145 Sq Ft

  130 W Kings Way, Winter Park, FL 32789

  Amazing opportunity in the Forest Hills subdivision in the heart of Historic Winter Park! As you enter this charming 4 bedroom home you’re welcomed by a spacious dining room that flows seamlessly into the large family room with fireplace, custom built-in shelving and storage cupboards, crown moulding and views over the rear yard and patio, perfect for relaxing or entertaining. To the front of the

  Andy Neal MAXIM REALTY ORLANDO

  130 W Kings Way, Winter Park, FL 32789
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  /39

  $1,300,000

  • 3 Beds
  • 3.5 Baths
  • 1,942 Sq Ft

  1450 Chestnut Ave, Winter Park, FL 32789

  Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timeless Mediterranean home offers three bedrooms, three and a half bathrooms, and just under 2,000 square feet of beautifully finished living space framed by mature magnolias and manicured hedges. A brick driveway leads to a two-car garage with carriage-style doors, while a covered entry showcases a solid arched

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1450 Chestnut Ave, Winter Park, FL 32789
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  /51

  $1,799,000

  • 3 Beds
  • 3 Baths
  • 3,297 Sq Ft

  825 Palmer Ave, Winter Park, FL 32789

  825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly positioned on an oversized .35-acre lot (85x173') with exclusive boathouse access to the prestigious

  Kelly Price KELLY PRICE & COMPANY LLC

  825 Palmer Ave, Winter Park, FL 32789
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  /43

  $1,799,000

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft

  1166 Oaks Blvd, Winter Park, FL 32789

  Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of thoughtfully designed living space.Relax on the charming front covered

  Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
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  /51

  $1,595,000

  • 5 Beds
  • 3.5 Baths
  • 3,292 Sq Ft

  1453 Lyndale Blvd, Winter Park, FL 32789

  Welcome to this updated and architecturally unique 5-bedroom, 3.5-bathroom custom home, offering 3,292 square feet of luxury living in the heart of Winter Park. Step inside and you’re immediately greeted by gleaming porcelain tile floors, smooth modern non-textured walls, and soaring ceilings that create a light and airy feel. The spacious living room features custom wall details, crown molding,

  Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1453 Lyndale Blvd, Winter Park, FL 32789
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  /28

  $320,000

  • 2 Beds
  • 2 Baths
  • 1,004 Sq Ft

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792

  FIRST-FLOOR LIVING WITH DIRECT WATER VIEWS AND AN UNBEATABLE LOCATION! Located in one of Winter Park’s most convenient and cared-for communities, The Gallery at Winter Park. This 2-bedroom, 2-bath condo showcases a beautifully updated kitchen and refreshed bathrooms. Contemporary luxury vinyl floors extend across the bedrooms and living areas for a clean, cohesive look. The primary suite is at

  Maria Elena Perez MEP REALTY INVESTMENTS LLC

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792
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  /56

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 2,565 Sq Ft

  215 Salvador Square, Winter Park, FL 32789

  Welcome home to this lovely four-bedroom, three-and-a-half-bath pool home in the prestigious Sevilla neighborhood of Winter Park! Tucked off a charming brick-lined street just 1⁄4 mile from Park Avenue, this .40-acre property offers both privacy and convenience to your Winter Park lifestyle. Inside, you’ll find timeless details such as marble and parquet flooring, crown molding, plantation

  Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

  215 Salvador Square, Winter Park, FL 32789
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  /25

  $349,900

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

  Charming Downtown Winter Park Pied-a-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
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  /51

  $1,285,000

  • 4 Beds
  • 2 Baths
  • 2,750 Sq Ft

  1981 Blue Ridge Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome home to this beautifully renovated 4-bedroom, 2-bathroom home nestled on a desirable corner lot in the heart of Winter Park’s Timberlane Shores community. Boasting

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1981 Blue Ridge Rd, Winter Park, FL 32789
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  /44

  $1,300,000

  • 3 Beds
  • 3.5 Baths
  • 3,363 Sq Ft

  800 Hamilton Place Ct, Winter Park, FL 32789

  Custom-built and beautifully maintained, this large 3-bedroom home with loft is located in prime Old Winter Park on a quiet cul-de-sac. The interior boasts 20'+ high ceilings, creating a grand and airy atmosphere throughout the main living spaces. High-end finishes include Viking stainless steel appliances, dolomite marble tile flooring, and a thoughtfully designed, functional layout ideal for

  Julian Torres, Jr EPIC REAL ESTATE ADVISORS LLC

  800 Hamilton Place Ct, Winter Park, FL 32789
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  /60

  $1,425,000

  • 4 Beds
  • 3.5 Baths
  • 3,349 Sq Ft

  2401 Lafayette Ave, Winter Park, FL 32789

  Seller is including a premium home warranty giving buyers peace of mind with coverage on HVAC, plumbing, appliances & more so you can move in with confidence! Professional deep cleaning will be paid for by seller before closing! Experience the charm and elegance of Winter Park living in this beautifully designed 4-bedroom, 3.5-bath home offering 3,604 square feet of thoughtfully crafted

  Nehad Darwish DIVINE ESTATES REALTY LLC

  2401 Lafayette Ave, Winter Park, FL 32789
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  /47

  $1,325,000

  • 4 Beds
  • 3.5 Baths
  • 2,953 Sq Ft

  1420 Palmer Ave, Winter Park, FL 32789

  Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave!Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of

  Amy Turner KELLER WILLIAMS WINTER PARK

  1420 Palmer Ave, Winter Park, FL 32789
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  /55

  $1,474,950

  • 4 Beds
  • 4 Baths
  • 3,474 Sq Ft

  952 Moss Ln, Winter Park, FL 32789

  Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 3-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find

  Terry Connors THE SHOP REAL ESTATE CO.

  952 Moss Ln, Winter Park, FL 32789
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  /59

  $1,445,000

  • 3 Beds
  • 3 Baths
  • 2,351 Sq Ft

  1741 Palmer Ave, Winter Park, FL 32789

  Welcome home to this one-of-a-kind, single-story Tuscan-style retreat nestled on an oversized lot in the heart of highly coveted Winter Park. From the moment you arrive, the round circular paver driveway and beautifully landscaped exterior set the tone for the warmth and elegance that awaits inside. Enter through custom wrought-iron gates into a private covered and screened in courtyard lanai,

  Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1741 Palmer Ave, Winter Park, FL 32789
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  /28

  $244,999

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792

  Charming 2-Story Condo in the Heart of Winter ParkLocated in the highly sought-after city of Winter Park, this beautifully maintained 2-bedroom, 1.5-bath condo offers the perfect blend of comfort, convenience, and community living. Along with a dedicated covered carport parking space. Just minutes from Park Avenue, top-rated shopping, and dining destinations, this home puts you at the

  Jessica Geer A+ REALTY PROFESSIONALS, INC

  200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
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  /33

  $236,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 204, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen appliances, and a complete interior fresh coat of

  Eddie Cooper MAINFRAME REAL ESTATE

  151 N Orlando Ave Unit 204, Winter Park, FL 32789
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  /58

  $1,295,000

  • 5 Beds
  • 4 Baths
  • 3,068 Sq Ft

  2105 Fosgate Dr, Winter Park, FL 32789

  This home is the perfect blend of resort luxury and farmhouse charm, with high-end finishes and features that cater to both relaxation and entertaining. From the resort-style backyard with a magnificent Saltwater Pool, lovely green space around the koi pond to the HGTV-worthy Interior with an entertainer’s dream kitchen, this has it all. The spacious split-bedroom floor plan, luxurious primary

  Eileen Winfrey LPT REALTY, LLC

  2105 Fosgate Dr, Winter Park, FL 32789
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  /16

  $1,449,000

  • 3 Beds
  • 3 Baths
  • 2,145 Sq Ft

  1644 Hibiscus Ave, Winter Park, FL 32789

  Charming, Well-Maintained Home on a Prime Lot in Winter Park’s Coveted Tree StreetsDon’t miss this rare opportunity to own a beautifully landscaped and meticulously maintained property on one of the most desirable streets in Winter Park. Situated on one of the largest lots in the sought-after Tree Streets, this home is perfect for a buyer or builder ready to create something truly special

  Harry Pool, III COLDWELL BANKER RESIDENTIAL RE

  1644 Hibiscus Ave, Winter Park, FL 32789
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  /53

  $241,900

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft

  200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792

  Excellent opportunity in a prime location in Central Florida. This two-bedroom, two-full-bath corner unit is in the Four Seasons Condominiums of Winter Park, just steps from the Cady Way Trail, Showalter Field, Ward Park, the YMCA, medical centers, and shopping. Park Avenue and museums are just minutes away. Four Seasons Condominiums is a 20-acre community located within the Winter Park city

  Lucy Gonzalez Zabala CHARLES RUTENBERG REALTY ORLANDO

  200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792
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  /45

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 2,388 Sq Ft

  1341 Lyndale Blvd, Winter Park, FL 32789

  Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park Village, this beautifully renovated 4-bedroom, 3-bath home offers the ultimate in walkable luxury living. Nestled on a charming brick street lined with sidewalks, this residence combines timeless elegance with unbeatable convenience.Inside, enjoy 10’ ceilings, rich wood,

  Brandon Geers COMPASS FLORIDA LLC

  1341 Lyndale Blvd, Winter Park, FL 32789
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  /69

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 2,841 Sq Ft

  1701 Palmer Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Charming Winter Park Pool Home – A Rare Opportunity! Nestled in the heart of Winter Park’s highly sought after 32789 zip code, this 4-bedroom, 3-bathroom pool home offers timeless charm, abundant space, and unlimited potential! Set on an expansive corner lot, this residence is just steps from Phelps Park, surrounded by tree-lined streets, and

  Jackie Swisher TRUST EQUITY GROUP LLC

  1701 Palmer Ave, Winter Park, FL 32789
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  /49

  $1,275,000

  • 6 Beds
  • 4 Baths
  • 2,284 Sq Ft

  726 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living areas, kitchens, and

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 N Pennsylvania Ave, Winter Park, FL 32789
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  /82

  $249,000

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 202, Winter Park, FL 32789

  2/2 * 956 SQ FT * LAKE KILLARNEY * CLOSE TO PARK AVE IN WINTER PARK * 3 MILES TO ROLLINS COLLEGE * NEW AC * NEW WATER HEATER * NEW INTERIOR PAINT * NEW LIGHTING *Perfectly located close to Park Ave in Winter Park, Rollins College, and Downtown Orlando. Fully updated, sought-after 956 Sq ft 2/2 Condo, on beautiful Lake Killarney a serene oasis in Winter

  Alison Maltby THE ANDERSON GROUP & CO PL

  2500 Lee Rd Unit 202, Winter Park, FL 32789
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  /50

  $1,290,000

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft

  1400 S Pennsylvania Ave, Winter Park, FL 32789

  Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. You will be amazed at this fully remodeled one level four bedroom home on a fenced corner lot. This home has amazing curb appeal, with its wide half circle paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living

  Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
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  /38

  $514,900

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  101 S Ranger Blvd, Winter Park, FL 32792

  Welcome to this beautifully updated and meticulously maintained home, nestled on a spacious corner lot in the highly sought-after Winter Park neighborhood—where the mailman still delivers right to your front door. Combining classic charm with modern upgrades, this three-bedroom, two-bathroom home offers the perfect balance of style, comfort, and functionality. Step inside to a bright and open

  Amy Turner KELLER WILLIAMS WINTER PARK

  101 S Ranger Blvd, Winter Park, FL 32792
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  /15

  $400,000

  • Land
  • 0.21 Acre
  • $1,904,762 per Acre

  1809 Palmer Ave, Winter Park, FL 32792

  Build your dream home in the heart of Winter Park! Located on the highly desirable Palmer Avenue, this premium lot offers a rare opportunity to create a custom residence just minutes from Park Avenue, Rollins College, top-rated schools, and the Winter Park Chain of Lakes. Situated among multi-million-dollar homes, this property is ideal for discerning buyers or builders seeking a great address

  Christina Munkberg COLDWELL BANKER RESIDENTIAL RE

  1809 Palmer Ave, Winter Park, FL 32792
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  /41

  $879,000

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789

  Welcome to The Cloisters, one of Winter Park’s most established lakefront communities, ideally located between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 6

Why Live in Winter Park

Winter Park, a neighborhood rich in history and charm, offers a glimpse into “Old Florida” with its hanging Spanish moss and lakeside views. Originally a resort community for northern business magnates in the 19th century, Winter Park features a mix of architectural styles, from ranchers and midcentury modern to Victorian and Spanish designs. Several homes and districts, including the Hannibal Square District, are listed on the National Register of Historic Places. The Hannibal Square Heritage Center honors the historic African American community with exhibitions and educational programs. The neighborhood is adorned with lush greenery and tranquil lakes, accessible through parks like Mead Botanical Garden, which has walking trails, an amphitheater, and a butterfly garden. Central Park, located in the heart of the shopping district, hosts year-round events and the annual Winter Park Sidewalk Art Festival. The Winter Park community center provides various programs and facilities, including a fitness center and community pool. Daily needs are met by grocery stores like Whole Foods and Trader Joe’s, while niche retailers and dining options, such as Hillstone Restaurant and Bosphorous Turkish Cuisine, are plentiful. Cultural institutions like Casa Feliz and the Charles Hosmer Morse Museum of Art add to the neighborhood's artistic appeal. Winter Park is safer than the national average and offers convenient access to major roadways like Interstate 4 and state Route 50.

Learn more about living in Winter Park

Frequently Asked Questions

Is Winter Park a good place to live?

Winter Park is a good place to live, receiving 4.3 stars from its residents. Winter Park is considered very car-dependent and somewhat bikeable with some transit options. Winter Park is a suburban neighborhood. Winter Park has 23 parks for recreational activities. It is somewhat dense in population with 6.8 people per acre and a median age of 41. The average household income is $111,076 which is above the national average. College graduates make up 54.4% of residents. A majority of residents in Winter Park are home owners, with 47.8% of residents renting and 52.2% of residents owning their home. A local real estate agent serving Winter Park can help you decide if this neighborhood is the right one for you. Learn more on our Winter Park neighborhood guide.

Is Winter Park, FL a safe neighborhood?

Winter Park, FL is less safe than the average neighborhood in the United States. It received a crime score of 5 out of 10.

How much do you need to make to afford a house in Winter Park?

The median home price in Winter Park is $725,000. If you put a 20% down payment of $145,000 and had a 30-year fixed mortgage with an interest rate of 6.5%, your estimated principal and interest payment would be $3,670 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $157K a year to afford the median home price in Winter Park. The average household income in Winter Park is $111K.

What are the best public schools in Winter Park?

The best public schools that serve Winter Park are:

• Winter Park High has an A+ Niche grade, a student teacher ratio of 21:1 and an average review score of 3.9.
• Dommerich Elementary School has an A Niche grade, a student teacher ratio of 16:1 and an average review score of 5.0.
• Baldwin Park Elementary has an A- Niche grade and a student teacher ratio of 16:1.

What are the best private schools in Winter Park?

The best private schools that serve Winter Park are:

• Park Maitland School has an A+ Niche grade, a student teacher ratio of 11:1 and an average review score of 4.6.
• Trinity Preparatory School has an A+ Niche grade, a student teacher ratio of 11:1 and an average review score of 4.3.
• St. Charles Borromeo Catholic School has an A Niche grade, a student teacher ratio of 14:1 and an average review score of 4.8.

What are the most popular zip codes in Winter Park, Winter Park, FL?

The most popular zip codes in Winter Park, Winter Park, FL include 32789, 32792, 32814, 32803 and 32751.

What are the most popular neighborhoods near Winter Park, Winter Park, FL?

The most popular neighborhoods near Winter Park, Winter Park, FL are Baldwin Park, Lake Howell, Orwin Manor, Colonialtown North and Audubon Park.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 69 days on the market compared to the national average of 52 days. The median sale price for homes in Winter Park, FL over the last 12 months is $675,000, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$675,000

Median Single Family Sale Price

$918,000

Median Townhouse Sale Price

$775,000

Median 2 Bedroom Sale Price

$240,950

Median 1 Bedroom Sale Price

$165,000

Average Price Per Sq Ft

$439

Number of Homes for Sale

211

Last 12 months Home Sales

625

Months of Supply

4.10

Median List Price

$725,000

Median Change From 1st List Price

6%

Median Home Sale Price YoY Change

2%