Winter Park, FL Homes for Sale

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  $875,000

  • 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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  /29

  $375,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  2827 Euston Rd, Winter Park, FL 32789

  Welcome to 2827 Euston Rd, a beautifully updated home in the highly desirable Winter Park area with the added bonus of no HOA! This charming residence offers 3 beds, 2baths, and a versatile bonus room that can be used as an office, playroom, or additional living space.The master suite is thoughtfully separated from the other two bedrooms, providing privacy and convenience. Inside, you’ll

  

  Evelyn Tejada

  REGENCY REAL ESTATE LLC

  (321) 461-5735

  2827 Euston Rd, Winter Park, FL 32789
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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

  $1,200,000

  • 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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  /8

  $310,000

  • Land
  • 1.01 Acres
  • $306,931 per Acre

  3520 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just over an acre, lot in coveted Winter Park. Nestled on the end of a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 467-7107

  3520 Wilde Ave, Winter Park, FL 32792
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  /36

  $765,000

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

  2418 Whitehall Cir, Winter Park, FL 32792

  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 luxury in a modern setting and with stunning curb

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (321) 599-7240

  2418 Whitehall Cir, Winter Park, FL 32792
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  /19

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 215-7673

  7706 Country Place Unit A8, Winter Park, FL 32792
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  /73

  $985,000

  • 3 Beds
  • 2 Baths
  • 3,158 Sq Ft

  7801 Georgeann St, Winter Park, FL 32792

  Live the Winter Park LAKEFRONT dream with this stunning 3-bedroom, 2-bath home on skiable LAKE WAUNATTA, Chain of Lakes, offering breathtaking water views and endless amenities and NO HOA! The entire second floor is dedicated to the luxurious primary suite, complete with a spacious office, oversized closets, enjoy your morning coffee or evening glass of wine on your private balcony overlooking

  

  Kelly Butterfield

  RE/MAX TOWN & COUNTRY REALTY

  (321) 599-6353

  7801 Georgeann St, Winter Park, FL 32792
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  /8

  $260,000

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
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  /22

  $719,000

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  2338 Tuscarora Trail, Maitland, FL 32751

  **Charming Dommerich Hills Home with Scenic Lake Views and Modern Updates*** Nestled in the desirable Dommerich Hills, this beautiful 4-bedroom, 2-bath lakeside home offers a serene lifestyle with views of the lush conservation area and Lake Waumpi. Mature trees and an expansive backyard create a peaceful retreat, with ample space to add a pool. The home’s classic Florida charm is enhanced with

  

  Timothy Smith

  WHITE WHALE REAL ESTATE

  (321) 342-1836

  2338 Tuscarora Trail, Maitland, FL 32751
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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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  $659,900 Open Sun 12PM - 3PM

  • 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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  $3,599,999

  • 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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  $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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  /43

  $1,199,000

  • 4 Beds
  • 5 Baths
  • 4,015 Sq Ft

  4052 Gilder Rose Place, Winter Park, FL 32792

  A rare opportunity to own this beautiful pool home in Winter Park at Bear Gully Pointe, a gated community located on a spring fed 137-acre Lake. This perfect 3-way split floor plan with pool views has an open fireplace to enjoy the mornings & evenings. The conservation area in back makes a very private pool & patio area. Expect to be impressed when entering the home with expansive ceilings, open

  Steve Lang HOMEVEST REALTY

  4052 Gilder Rose Place, Winter Park, FL 32792
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  /25

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,349 Sq Ft

  657 Overspin Dr, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. **Seller is motivated and encourages all serious offers—bring your buyers!** Welcome to your cozy Winter Park retreat! This charming 4-bedroom, 2-bath home blends comfort and convenience in one perfect package. Nestled on a spacious lot with a large backyard—ideal for entertaining, gardening, or playing fetch—this home also features a unique

  Abby Nelson RE/MAX 200 REALTY

  657 Overspin Dr, Winter Park, FL 32789
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  $2,900,000 Open Sun 5PM - 7PM

  • 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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  $1,350,000 Open Sun 1PM - 3PM

  • 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 AccessThis 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

  Kimberly Slinger KELLY PRICE & COMPANY LLC

  2525 Venetian Way, Winter Park, FL 32789
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  /37

  $950,000

  • 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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  $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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  $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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  /29

  $405,000

  • 4 Beds
  • 2 Baths
  • 1,598 Sq Ft

  5600 Revelwood Loop, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. PRICE IMPROVEMENT!!!! Clean, BRIGHT and MOVE IN READY!!! Prepare to be IMPRESSED with this BEAUTIFUL 4 bedroom, 2 Bath 1598 Sq Ft home in the quaint and quiet Bridgewater Community! This terrific Winter Park home is LIGHT-FILLED, SPACIOUS and has a terrific 3 way split floorplan. Upon entering the home, you will notice the vaulted ceiling, fresh

  Tami Vincent REAL ESTATE PROS

  5600 Revelwood Loop, Winter Park, FL 32792
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  $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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  $1,575,000

  • 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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  /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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  /27

  $665,000

  • 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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  /20

  $265,000

  • 2 Beds
  • 2.5 Baths
  • 1,295 Sq Ft

  2394 Sun Valley Cir, Winter Park, FL 32792

  This charming 2-bedroom, 2-bathroom condo offers 1,295 square feet of comfortable single-level living, thoughtfully designed for easy living and entertaining. The open floor plan boasts a spacious, sunlit living area and a well-appointed kitchen, perfect for culinary creations. Both bedrooms are generously sized and provide privacy, each featuring its own en-suite bathroom for added convenience.

  Jamie Vanosdol EXP REALTY LLC

  2394 Sun Valley Cir, Winter Park, FL 32792
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  $839,900

  • 4 Beds
  • 3.5 Baths
  • 2,962 Sq Ft

  675 Overspin Dr, Winter Park, FL 32789

  This well-appointed house features approximately 2,962 square feet of living space with four bedrooms and three and a half bathrooms. The property sits on approximately 0.16 acres of land. The home offers two laundry rooms and all updated appliances, providing ample functionality and convenience. The primary bedroom is spacious and well-appointed, offering ample room for relaxation and privacy.

  Zoe Essma COLDWELL BANKER RESIDENTIAL RE

  675 Overspin Dr, Winter Park, FL 32789
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  /24

  $135,000

  • 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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  /61

  $1,625,000

  • 4 Beds
  • 4 Baths
  • 3,777 Sq Ft

  1650 Lakehurst Ave, Winter Park, FL 32789

  1650 Lakehurst Avenue, Winter Park, FL | Offered at $1,695,000 | Beautiful brick home on a huge 0.38 acre corner lot, in the Heart of Winter Park! Designed with traditional elegance in mind, this stately residence offers 4 bedrooms, 4 full baths, and over 3,700 sf of living space. Enter the home through the foyer where you’ll find formal living and dining rooms to your left and right, and a large

  Kelly Price KELLY PRICE & COMPANY LLC

  1650 Lakehurst Ave, Winter Park, FL 32789
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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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  $935,000 Open Sun 1PM - 4PM

  • 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

  $205,000

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3247 Forest Oaks Ct Unit 116, Winter Park, FL 32792

  Welcome to this beautifully updated 2-bedroom, 2.5-bath condo in the heart of Winter Park! Featuring ceramic tile and laminate wood flooring throughout, this home offers a modern feel with upgraded kitchen finishes, refreshed lighting, ceiling fans, and recently updated sinks, toilets, and flooring. The spacious layout provides comfort and convenience, with both bedrooms offering en-suite

  Brandon Feng KELLER WILLIAMS WINTER PARK

  3247 Forest Oaks Ct Unit 116, Winter Park, FL 32792
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  /20

  $189,900

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

  Welcome to “Four Seasons” condominiums in Winter Park. This 2nd floor 2-bedroom 2 bath unit has a great view of the pool, tennis and shuffle court and is right outside your front door. The floor plan offers a nice-sized living dining area plus a spacious primary bedroom. Updates to the condo are... roof replaced in 2023, Re-piped 2025, new water heater 2025, AC 2017. Granite counter tops in the

  Evelyn Pilchick RE/MAX 200 REALTY

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
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  /59

  $1,550,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft

  1541 Chestnut Ave, Winter Park, FL 32789

  An extraordinary home, built in 2018 by Lazarus, is situated on a quaint cobblestone street in the exclusive “Tree Streets” of Winter Park. Contemporary transitional design has many details and has been beautifully maintained and upgraded. A 4-bedroom 3 bath pool home stretches over 2,800 sf with natural light filling the spaces through expansive windows. The home offers open concept living in

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1541 Chestnut Ave, Winter Park, FL 32789
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  /43

  $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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  /23

  $889,000

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  1217 Kenwood Ave, Winter Park, FL 32789

  The inviting bungalow at 1217 Kenwood Ave is located just a few houses off famed Park Avenue and steps from the Winter Park Village, which is fresh off a $50 million transformation and includes popular bars and restaurants, a movie theater and shopping. The home was fully renovated in 2018 with updates to the HVAC, electrical, plumbing, flooring, subflooring, interiors, and a new roof- offering

  Kurt Lehmann LEHMANN REALTY INC.

  1217 Kenwood Ave, Winter Park, FL 32789
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  /84

  $445,000

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  1900 Erudite Way, Winter Park, FL 32792

  Step into effortless style and comfort in this beautifully crafted 2024 townhome located in Winter Park's desirable Grayson Square community. From the moment you arrive, you’ll appreciate the home’s modern curb appeal and smart features, including a convenient keypad entry and smart lighting throughout.Inside, an open-concept layout welcomes you with rich wood floors, designer lighting,

  Erica Diltz BALDWIN PARK REALTY LLC

  1900 Erudite Way, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 11

Why Live in Winter Park

Winter Park, a historic urban village, offers a blend of residential and commercial areas set among the Winter Park Chain of Lakes. The neighborhood is known for its rich arts scene and highly rated schools, including Winter Park High and Trinity Preparatory School of Florida. Park Avenue remains a central hub with high-end boutiques and dining options like The Ravenous Pig. Rollins College and The Rollins Museum of Art add to the cultural attractions. Residents enjoy outdoor activities such as boating and paddleboarding on the lakes, and green spaces like Central Park, which features walking paths and a rose garden. The Winter Park Country Club and Golf Course provides a public nine-hole course. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park foster a strong sense of community. The area has a lower crime rate compared to the national average, with a violent crime rate of 2.9 per 1,000 people. Winter Park's home styles range from petite bungalows to lakeside mansions, including New Traditional, midcentury ranch, Colonial Revival, and Contemporary homes. The neighborhood is well-connected with Interstate 4, SunRail, and Lynx bus services, and is about 10 miles from downtown Orlando and 20 miles from Orlando International Airport.

Learn more about living in Winter Park

Frequently Asked Questions

What is the average home price in Winter Park, FL?

Homes for sale in Winter Park, FL have an average home price of $1,159,053.

Are home prices dropping in Winter Park?

Yes, home prices in Winter Park are down 2% in the last 12 months.

How many homes have sold over the last 12 months in Winter Park, FL?

686 homes have sold in Winter Park, FL over the last 12 months.

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

The most popular zip codes in Winter Park, FL include 34787, 34747, 32712, 34746 and 32703.

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

The median home price in Winter Park is $649,900. If you put a 20% down payment of $130,000 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $3,380 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $145K a year to afford the median home price in Winter Park.

How are the schools in Winter Park, FL?

Winter Park, FL has highly rated public and private schools. Some of the best schools in Winter Park based on Niche Grades are Trinity Preparatory School, Dommerich Elementary School and Audubon Park School. Browse all the schools in Winter Park, FL to learn more.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 64 days on the market compared to the national average of 50 days. The median sale price for homes in Winter Park, FL over the last 12 months is $595,000, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$595,000

Median Single Family Sale Price

$785,000

Median Townhouse Sale Price

$480,000

Median 2 Bedroom Sale Price

$238,500

Median 1 Bedroom Sale Price

$170,000

Average Price Per Sq Ft

$414

Number of Homes for Sale

256

Last 12 months Home Sales

686

Months of Supply

4.50

Median List Price

$649,900

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

-2%