Winter Park, FL Homes for Sale

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  /29

  $395,000

  • 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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  /44

  $748,000

  • 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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  /27

  $107,000

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft

  3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792

  SELLER WILL GIVE A $5,000 CREDIT TOWARDS CLOSING COSTS!! Unlock the potential of this two-bedroom, two-bathroom condominium located in the Colonies community. This unit is has stainless steel appliances and granite countertops in both the kitchen and bathrooms. Each bedroom features spacious walk-in closets. A new A/C unit was just installed! The community has desirable amenities including a

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 399-2572

  3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792
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  /100

  $8,799,000 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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  /36

  $800,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,745 Sq Ft

  441 N Capen Ave, Winter Park, FL 32789

  Rare find in the heart of Historic West Winter Park - Newer 2017 solid built David Weekley home now available! This modern designed chic home offers energy efficient features with luxury design. Walk into the home and be impressed by the voluminous ceilings and 8' door frames adorned with ceiling crown molding. This unique home design offers ultimate privacy with all bedrooms on the lower

  Susan Taliaferro COLDWELL BANKER RESIDENTIAL RE

  441 N Capen Ave, Winter Park, FL 32789
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  /66

  $1,400,000 Open Sun 2PM - 4PM

  • 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 kitchen

  Kimberly Slinger KELLY PRICE & COMPANY LLC

  2525 Venetian Way, Winter Park, FL 32789
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  /58

  $1,450,000

  • 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

  $235,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 913 Sq Ft

  1250 S Denning Dr Unit 230, Winter Park, FL 32789

  Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floor unit offers the ease of single-level living once inside, featuring an open-concept layout filled with natural light. The updated kitchen (2016) boasts stylish tile flooring that mimics hardwood, granite countertops, a farmhouse sink, and stainless-steel appliances, all

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  1250 S Denning Dr Unit 230, Winter Park, FL 32789
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  /16

  $1,495,000

  • 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 in an

  Harry Pool, III COLDWELL BANKER RESIDENTIAL RE

  1644 Hibiscus Ave, Winter Park, FL 32789
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  /100

  $1,165,000

  • 5 Beds
  • 5 Baths
  • 3,983 Sq Ft

  2832 Bear Island Pointe, Winter Park, FL 32792

  Welcome to 2832 Bear Island Pointe in Winter Park's premier gated community, Cypress Reserve! This meticulously maintained estate-like home is move-in-ready with 5 bedrooms plus a large office room with its own bathroom and separate exterior entry. Nestled near the serene Bear Gully Lake, this stunning residence offers the perfect blend of elegance, convenience, and resort-style living. The

  Drew Belani COMPASS FLORIDA LLC

  2832 Bear Island Pointe, Winter Park, FL 32792
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  /39

  $800,000

  • 4 Beds
  • 3 Baths
  • 2,360 Sq Ft

  600 Brechin Dr, Winter Park, FL 32792

  Welcome to one of the most sought after neighborhoods of Kenilworth Shores in Winter Park! Nestled among tree-lined streets where the mail is still delivered right to your door, this beautifully appointed 4-bedroom, 3-bathroom home blends timeless elegance with modern comfort. From the moment you step onto the charming brick walkway, you'll fall in love with the lush, mature landscaping and

  Amy Turner KELLER WILLIAMS WINTER PARK

  600 Brechin Dr, Winter Park, FL 32792
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  /53

  $1,025,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,377 Sq Ft

  2923 Cove Trail, Winter Park, FL 32789

  A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market for the FIRST TIME. 2923 Cove Trail is nestled between the best of Winter Park & Maitland. Masterly created by the renowned Charlie Clayton it blends unmatched craftsmanship with modern design & flexibility craved by you, today’s discerning buyer. REIMAGINED in 2011 this

  Robin Delaney KELLER WILLIAMS ADVANTAGE III

  2923 Cove Trail, Winter Park, FL 32789
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  /43

  $458,000

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

  2812 Bright Bird Ln, Winter Park, FL 32792

  Built in 2024, this move-in ready 3-bedroom, 2.5-bathroom townhome is located in the gated community of Grayson Square, just a little over 15 minutes from Park Avenue in downtown Winter Park. Designed with a sleek, neutral gray color scheme and modern finishes throughout, the home features an open-concept layout filled with natural light that enhances its bright and airy feel. The main level

  Jessica Snyder EXP REALTY LLC

  2812 Bright Bird Ln, Winter Park, FL 32792
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  /31

  $219,900

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  2348 Sun Valley Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Dreams Do Come True! Spectacular Opportunity in Sought-After Cedarwood Village – Winter Park!Welcome to this charming 2-bedroom, 2-bathroom single-story condo tucked away in the peaceful rear section of the community—offering beautiful, tranquil views and a sense of privacy that’s hard to find. With a new roof already in place, the foundation is set

  Freddie Crespo INVESTOR'S REAL ESTATE LLC

  2348 Sun Valley Cir, Winter Park, FL 32792
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  /15

  $210,000

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

  1695 Lee Rd Unit E215, Winter Park, FL 32789

  Experience modern living in this beautifully updated 3-bedroom, 2-bath condo at 1695 Lee Rd E215, Winter Park, FL 32789. Nestled in the heart of Winter Park, this unit offers easy access to Park Avenue’s upscale shopping and dining, Rollins College, and nearby cultural attractions. Inside, the fully renovated kitchen boasts elegant quartz countertops, contemporary cabinetry, and updated

  Kerem Munoz- Franquiz LA ROSA REALTY CENTRAL FLORIDA

  1695 Lee Rd Unit E215, Winter Park, FL 32789
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  /41

  $474,500

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  1628 Little Wren Ln, Winter Park, FL 32792

  Improved Price! Welcome to your private "nest" on Little Wren. Nestled among the trees, this modern masterpiece is located directly next to a wide open green space and also backs to a private wooded area giving you beautiful, natural, unobstructed views. The home's modern architecture style is evident from the moment you approach with its striking front door acting as a key focal point.

  Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

  1628 Little Wren Ln, Winter Park, FL 32792
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  /20

  $189,900

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft

  200 Saint Andrews Blvd Unit 1603, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to FOUR SEASONS... a serene, centrally located community in Winter Park near Full Sail, Cady Way Trail/Park, Showalter Field, Ward Park & Winter Park Hospital. EXACTLY WHAT YOU HAVE BEEN SEARCHNG FOR!! Covered entry & spacious rooms makes this a perfect place to call home. Living/ Dining room combination, charming kitchen & oversized

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  200 Saint Andrews Blvd Unit 1603, Winter Park, FL 32792
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  /26

  $225,000

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792

  We are proud to bring to market this incredibly private END UNIT condo within the Hidden Oaks community. The unit offers three bedrooms (all upstairs), two full bathrooms (upstairs) and one half bathroom (downstairs), two reserved parking spots, upgraded wood-look ceramic tile, upgraded light fixtures, upgraded bathroom mirrors and upgraded fans throughout, upgraded thick granite countertop in

  Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792
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  /31

  $185,000

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

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792

  Experience the perfect blend of charm, convenience, and value in this beautifully maintained (freshly cleaned and painted) 2-bed, 2.5-bath townhouse-style condo nestled in the heart of the desirable Hidden Oaks community in Winter Park. Whether you're a first-time homebuyer, a savvy investor, or simply seeking a cozy space to call home, this property is a standout choice. Key Features Include:

  Ali Khaku, MBA REALTY HUB

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792
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  /44

  $1,050,000

  • 4 Beds
  • 2.5 Baths
  • 2,546 Sq Ft

  2680 Oglesby Ave, Winter Park, FL 32789

  Welcome to your Winter Park dream home—a modern farmhouse masterpiece blending timeless design with contemporary comforts. Built in 2019, this single-family home offers four spacious bedrooms, two and a half baths, and luxurious finishes you'll cherish for years.Nestled between the highly coveted areas and school zones of College Park and Winter Park, this property is an opportunity you

  Kris Kennedy COMPASS FLORIDA LLC

  2680 Oglesby Ave, Winter Park, FL 32789
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  /33

  $185,000

  • 1 Bed
  • 1 Bath
  • 835 Sq Ft

  200 St Andrews Blvd Unit 512, Winter Park, FL 32792

  **This property qualifies for a closing cost credit up to $2,700 through the Seller’s preferred lender.**Welcome home to this cozy 1-bedroom, 1-bathroom, second-floor unit in the heart of Winter Park. As you step inside the common area, head upstairs to your private entrance. The open living room is filled with natural light and features sliding glass doors that lead to your own private balcony –

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  200 St Andrews Blvd Unit 512, Winter Park, FL 32792
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  /27

  $219,000

  • 2 Beds
  • 2.5 Baths
  • 1,578 Sq Ft

  7468 Swallow Run Unit 38, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this charming two bedroom, two and a half bathroom condo in the heart of Winter Park. This home offers a spacious and functional layout with a half bath on the first floor, perfect for guests, and an interior laundry room for added convenience. The living room features a cozy fireplace, creating a warm and inviting atmosphere. Two sliding

  Chris Creegan CREEGAN GROUP

  7468 Swallow Run Unit 38, Winter Park, FL 32792
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  /61

  $950,000

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

  5325 Cypress Reserve Place, Winter Park, FL 32792

  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 it’s a lifestyle upgrade. With a heated pool & spa, 3-car garage, newly installed roof, and spacious layout, this home offers

  Dori Estrada LPT REALTY, LLC

  5325 Cypress Reserve Place, Winter Park, FL 32792
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  /24

  $189,000

  • 2 Beds
  • 2 Baths
  • 1,067 Sq Ft

  200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792

  FOUR SEASONS CONDO IN Winter Park is Centrally located. Great community with a clubhouse, a fitness center recently renovated, 3 swimming pools, tennis courts, and shuffleboard court. Close by you are only a short walk to Cady Way Park for baseball and soccer fields as well as other playgrounds. This 2 bedrooom/2 bath unit has been updated with laminate flooring, ceiling fans, all appliances

  Patricia Wojewoda BETTER HOMES & GARDENS RE STAR

  200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792
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  /36

  $849,999 Open Sat 3PM - 5PM

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

  2418 Whitehall Cir, Winter Park, FL 32792

  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 appeal, this TURNKEY residence with high-end finishes

  Alice Anne Jackson CORCORAN PREMIER REALTY

  2418 Whitehall Cir, Winter Park, FL 32792
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  /14

  $205,000

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792

  Welcome to this inviting first-floor condo, designed with an open concept floor plan that seamlessly blends comfort and style. The expansive family room provides a generous space for family gatherings and entertaining, with abundant natural light flowing through large windows and a screened-in porch. This condo features two generously sized bedrooms and two full bathrooms, offering ample space

  Dean D Nikolic PMI PROPERTY ALLIANCE

  2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792
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  /21

  $200,000

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft

  145 Scottsdale Square Unit 145, Winter Park, FL 32792

  Excellent opportunity to own an apartment home close to everything imaginable near downtown Orlando. One block form Full Sail University. Completely renovated and exquisitely appointed.

  Julio Cesar Perez GLOVEN REALTY

  145 Scottsdale Square Unit 145, Winter Park, FL 32792
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  /26

  $795,000

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

  1344 Blue Stem Ln, Winter Park, FL 32792

  This is it, the home you have been searching for. Welcome to a stunning home that seamlessly blends contemporary design with natural beauty. Nestled on a beautiful sought after lot, this spacious residence offers unparalleled comfort and style, with serene pond and fountain views that create a peaceful retreat on your screened in lanai.Inside, the open-concept layout is flooded with

  Denae Zoellner CASTLE & COTTAGE REALTY LLC

  1344 Blue Stem Ln, Winter Park, FL 32792
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  /17

  $224,888

  • 2 Beds
  • 1.5 Baths
  • 1,393 Sq Ft

  7466 Canford Ct Unit 25, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. This home can be purchased with NO MONEY DOWN!! Welcome to Whisperwood! This recently updated 2 bedroom, 1.5 bathroom, 2-story condo makes the perfect home. Located just minutes away from Target and Winter Park’s restaurants, this property offers a sought-after lifestyle that combines convenience with modern living. Step inside and prepare to be

  Hillary Alvarez KELLER WILLIAMS ADVANTAGE III

  7466 Canford Ct Unit 25, Winter Park, FL 32792
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  /5

  $724,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft

  1632 Haven Dr, Orlando, FL 32803

  1632 Haven Dr, Orlando, FL 32803: Welcome to your dream home in vibrant Wadeview Park! This exquisite new construction townhome by David Weekley Homes offers modern living with a touch of elegance, boasting 1,772 square feet of thoughtfully designed space. Perfect for families and professionals alike, this residence features 3 Spacious Bedrooms: Enjoy restful retreats in generously sized

  David Weekley Homes

  Rittenberg, Orlando, FL 32803
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  /30

  $440,000

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  5001 Tangerine Ave, Winter Park, FL 32792

  Charming Winter Park Home with PoolWelcome to 5001 Tangerine Avenue, a bright and welcoming 3-bedroom, 2-bath home in the heart of Winter Park. Situated on a spacious 0.32-acre lot, this 1,732 sq ft home features an inviting layout perfect for relaxing or entertaining.Enjoy sunny Florida days by your private pool and take advantage of the large yard for outdoor fun or future possibilities.

  Jason Neves MARK SPAIN REAL ESTATE

  5001 Tangerine Ave, Winter Park, FL 32792
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  /4

  $340,000

  • 3 Beds
  • 3 Baths
  • 1,803 Sq Ft

  2487 Harbour Way, Winter Park, FL 32792

  Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for those seeking comfort, convenience and quality of life.Located in one of the most sought-after areas of Winter Park, with an excellent location, close to schools, shops, restaurants, parks and much more!The community offers a complete infrastructure with a swimming pool, playground,

  Marcus Freire de Araujo WRA BUSINESS & REAL ESTATE

  2487 Harbour Way, Winter Park, FL 32792
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  /16

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft

  2711 Parkland Dr, Winter Park, FL 32789

  Welcome to this delightful 1,600 sqft home in one of Winter Park's most coveted neighborhoods. This three-bedroom, two-bathroom home blends classic charm with modern updates. The beautifully updated kitchen features newer appliances and opens to a cozy living area with a character-rich wood-burning fireplace. The versatile 23'x11' living and dining area offers multiple configuration options,

  Greg Martinez CORCORAN PREMIER REALTY

  2711 Parkland Dr, Winter Park, FL 32789
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  /35

  $2,100,000

  • 4 Beds
  • 4.5 Baths
  • 3,248 Sq Ft

  2402.5 Temple Dr, Winter Park, FL 32789

  Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 150-foot private drive with gate. Designed with comfortable yet sophisticated living space, this home is perfect for those seeking a serene retreat for both everyday living and entertainment. The heart of the home is the sizable kitchen, boasting a gas stove, high-end

  Steve Schiffer OLDE TOWN BROKERS INC

  2402.5 Temple Dr, Winter Park, FL 32789
• 

  

  /23

  $649,900 Open Sun 1PM - 5PM

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft

  236 N Ranger Blvd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Fully Renovated – EXPERIENCE WINTER PARK! This beautifully updated quarter acre Medallion Home offers 3 spacious bedrooms and 2 full bathrooms, with a bright open-concept layout and an inviting Florida room that overlooks a private, tree-lined backyard—perfect for family gatherings, peaceful mornings, or relaxed evenings at home.Your home gives you

  Ramses Misel Trillos EXP REALTY LLC

  236 N Ranger Blvd, Winter Park, FL 32792
• 

  

  /33

  $839,900

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft

  2168 Marsh Sedge Ln, Winter Park, FL 32792

  Welcome to your future home, where style, comfort, and technology come together seamlessly. This stunning 4-bedroom, 3-bath residence is nestled in the highly desirable gated community of Hawks Crest, known for its luxurious resort-style amenities and unbeatable location.From the moment you enter, you’ll be greeted by a spacious and thoughtfully designed open-concept layout, perfect for both

  Marcelle Da Silva Sampaio SELECTA REALTY LLC

  2168 Marsh Sedge Ln, Winter Park, FL 32792
• 

  

  /22

  $120,000

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

  316 Scottsdale Square Unit 316, Winter Park, FL 32792

  Welcome to 316 Scottsdale Square, a delightful 2-bedroom, 1 and half bathroom condo located in desirable Winter Park. This home features a spacious open floor plan with natural light, ideal for comfortable living. The kitchen includes modern appliances and overlooks the cozy living area, perfect for entertaining. The utility room is equipped with a washer and dryer, plus extra storage space for

  Tyann Huynh JADE KEY REALTY LLC

  316 Scottsdale Square Unit 316, Winter Park, FL 32792
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  /32

  $400,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,727 Sq Ft

  264 Balfour Dr, Winter Park, FL 32792

  Welcome to 264 Balfour Drive — an exclusive residence within a private enclave of just 13 elegant townhomes in the heart of Winter Park designed by architect Nils Schweizer. a student of Frank Lloyd Wright. Offering an attached two-car garage and a premier location, this home blends sophistication with comfort in every detail.Step into a grand living room where soaring ceilings and expansive

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  264 Balfour Dr, Winter Park, FL 32792
• 

  

  /43

  $1,749,000

  • 3 Beds
  • 3.5 Baths
  • 3,112 Sq Ft

  101 S New York Ave Unit 311, Winter Park, FL 32789

  Discover luxury living in this exquisite two-story condominium, located on the third floor of the highly sought-after Douglas Grand. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends entertaining with everyday comfort. Step into a blank canvas offering a clean landscape—free of flooring—allowing you to effortlessly bring your own design vision to life. Whether you

  Tiffany Grindstaff KELLY PRICE & COMPANY LLC

  101 S New York Ave Unit 311, Winter Park, FL 32789
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  /15

  $1,275,000

  • Land
  • 0.38 Acre
  • $3,355,263 per Acre

  309 Park Ct N, Winter Park, FL 32789

  Endless Potential in the Heart of Park North! Just steps from the charm and energy of Winter Park’s Park Avenue—where boutique cafés, fine dining, art galleries, museums, Central Park, and the Winter Park 9 Golf Course await—this rare Park North gem offers the ultimate opportunity to create your dream home. Nestled at the end of a peaceful cul-de-sac, this expansive .38-acre lot (16,534 SF) is a

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  309 Park Ct N, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 11

About Winter Park

Winter Park began in the 1880s when two New Englanders set out to plan a community that would appeal to other ex-pats from the north. Along with the promise of warm, sunny winters, they established good schools and a lively arts scene to lure wealthy residents. The main commercial district, Park Avenue, was where residents shopped and ate together. The city’s chain of lakes provided endless hours of boating and fishing. Over the years, Winter Park has grown to feel more like a Central Florida city, with shopping centers and access to major high ...

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 $1,126,270.

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

684 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, 34746, 32712 and 32703.

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

The median home price in Winter Park is $649,000. If you put a 20% down payment of $129,800 and had a 30-year fixed mortgage with an interest rate of 6.81%, your estimated principal and interest payment would be $3,390 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 71 days on the market compared to the national average of 47 days. The average sale price for homes in Winter Park, FL over the last 12 months is $1,000,217, up 2% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)

$599,500

Median Single Family Price

$825,000

Median Townhouse Price

$485,000

Median 2 Bedroom Price

$236,000

Median 1 Bedroom Price

$158,000

Average Price Per Sq Ft

$406

Number of Homes for Sale

242

Last 12 months Home Sales

684

Months of Supply

4.20

Median List Price

$649,000

Median Discount From 1st List Price

6%

Median Home Sale Price YoY Change

2%