28,402

Winter Park, FL Homes

Section Image Section Image
  • /43

    $475,000

    Open Sat 11AM - 2PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,622 Sq Ft

    3641 Hawthorne Ln, Winter Park, FL 32792

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed

    Agent Photo

    Keegan Siegfried

    LPT REALTY, LLC

    3641 Hawthorne Ln, Winter Park, FL 32792
  • /18

    Starting at $1,330 Per Month

    • Studio - 2 Beds

    311 N Knowles Ave, Winter Park, FL 32789

    Park East Apartments, a charming community of studio, one, and two bedroom homes in the heart of Winter Park, FL. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style.Choose from a wide array of floor plans and layouts to find the home that meets your needs. Your fully equipped kitchen opens

    Park East - Park Knowles Apartments

    311 N Knowles Ave, Winter Park, FL 32789
  • /2

    $567,000

    Sold Apr 02, 2026

    1459 Nottingham Dr, Winter Park, FL 32792

    • 5 Beds
    • 2.5 Baths
    • 1,885 Sq Ft
    • Built 1971

    Last Sold Summary

    • $301/SF
    • 2 Days On Market

    Current Estimated Value $562,783

    Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

    1459 Nottingham Dr, Winter Park, FL 32792
    • /60

      Est $1,621,122

      Not Listed For Sale

      1318 Chapman Cir, Winter Park, FL 32789

      • 4 Beds
      • 3.5 Baths
      • 3,105 Sq Ft
      • Built 2014
      1318 Chapman Cir, Winter Park, FL 32789

      Last Sold Summary

      • 162 Days On Market

  • /41

    $2,495,000

    $155K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,011 Sq Ft

    1130 Park North Place, Winter Park, FL 32789

    Half-acre lot just steps from Park Avenue shopping and dining, tucked on a quiet cul-de-sac in the heart of Winter Park.This traditional two-story home offers a well-designed floorplan for both everyday living and entertaining. From the moment you enter, the home feels warm and inviting. The main level features a spacious primary suite along with connected living spaces that flow easily from

    Agent Photo

    Jennifer King

    CORCORAN PREMIER REALTY

    1130 Park North Place, Winter Park, FL 32789
  • /36

    Starting at $1,252 Per Month

    • Studio - 3 Beds

    2000 Village Ln, Winter Park, FL 32792

    5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

    The Taylor at Winter Park

    2000 Village Ln, Winter Park, FL 32792
  • /2

    $690,000

    Sold Aug 14, 2025

    2433 Whitehall Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft
    • Built 1962

    Last Sold Summary

    • 5% Above List Price
    • $375/SF
    • 2 Days On Market

    Current Estimated Value $691,233

    Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

    2433 Whitehall Cir, Winter Park, FL 32792
    • /9

      Est $288,476

      Not Listed For Sale

      5774 Shale Ct, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,041 Sq Ft
      • Built 1985
      5774 Shale Ct, Winter Park, FL 32792

      Last Sold Summary

      • 1 Day On Market

  • /23

    $1,825,000

    New Construction Pending
    • 5 Beds
    • 5.5 Baths
    • 3,655 Sq Ft

    2305 Coldstream Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and

    Agent Photo

    Jennifer King

    CORCORAN PREMIER REALTY

    2305 Coldstream Dr, Winter Park, FL 32792
  • /19

    Starting at $1,250 Per Month

    • 1 - 2 Beds

    2610-2617 Eastbrook Blvd, Winter Park, FL 32792

    Nestled within the serene and picturesque neighborhood of Lake Howell, Eastbrook Apartments offers a peaceful lakeside living experience with all the conveniences of a big city. This charming community in the Winter Park area is ideal for those seeking a blend of tranquility and accessibility. With 29 exclusive units, Eastbrook provides an intimate living environment with spacious and

    Eastbrook Apartments

    2610-2617 Eastbrook Blvd, Winter Park, FL 32792
  • /2

    $730,000

    Sold Mar 23, 2026

    1213 Lindenwood Ln, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,505 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $291/SF
    • 81 Days On Market

    Current Estimated Value $718,031

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1213 Lindenwood Ln, Winter Park, FL 32792
    • /24

      Est $180,920

      Not Listed For Sale

      229 Lewfield Cir Unit 229, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 953 Sq Ft
      • Built 1973
      229 Lewfield Cir Unit 229, Winter Park, FL 32792

      Last Sold Summary

      • 61 Days On Market

  • /20

    $474,900

    Open Sat 10AM - 2PM $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,376 Sq Ft

    501 Heritage Blvd, Winter Park, FL 32792

    Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality. A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights include: - Newer

    Bernardo Carrasquel B EXP REALTY LLC

    501 Heritage Blvd, Winter Park, FL 32792
  • /35

    Starting at $1,556

    Total Monthly Price

    • 1 - 3 Beds

    2015 New Stonecastle Terrace, Winter Park, FL 32792

    Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

    Stonecastle Apartment Homes

    2015 New Stonecastle Terrace, Winter Park, FL 32792
  • /2

    $1,590,000

    Sold Mar 06, 2026

    1166 Oaks Blvd, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,860 Sq Ft
    • Built 2018

    Last Sold Summary

    • 12% Below List Price
    • $556/SF
    • 153 Days On Market

    Current Estimated Value $1,621,179

    Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

    1166 Oaks Blvd, Winter Park, FL 32789
    • /45

      Est $1,854,719

      Not Listed For Sale

      1433 Sarazens Place, Winter Park, FL 32792

      • 5 Beds
      • 5.5 Baths
      • 3,954 Sq Ft
      • Built 2020
      1433 Sarazens Place, Winter Park, FL 32792

      Last Sold Summary

      • 0 Days On Market

  • /51

    $1,149,900

    $49K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,652 Sq Ft

    1448 Lake Florence Way, Winter Park, FL 32792

    Located within an intimate gated community of just 28 homes and only a short drive to Downtown Winter Park, this exceptional former model home by K. Hovnanian Homes showcases over $200,000 in builder and custom upgrades with luxury finishes and thoughtful design throughout. Residents enjoy access to a private community dock, perfect for launching a canoe or paddleboard or simply relaxing while

    Abby Nelson RE/MAX 200 REALTY

    1448 Lake Florence Way, Winter Park, FL 32792
  • /16

    Starting at $1,599 Per Month

    • 2 Beds

    4704 Lucier Ct, Winter Park, FL 32792

    *Restricted units only*App and Admin special for only $175!Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will

    The Vista at Winter Park

    4704 Lucier Ct, Winter Park, FL 32792
  • /2

    $390,000

    Sold Jun 11, 2026

    7517 Laurel Springs Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Below List Price
    • $232/SF
    • 4 Days On Market

    Current Estimated Value $413,579

    Last Listing Agent Jay Patterson KELLER WILLIAMS ADVANTAGE REALTY

    7517 Laurel Springs Dr, Winter Park, FL 32792
    • /14

      Est $533,300

      Not Listed For Sale

      1821 Hammerlin Ave Unit A, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,818 Sq Ft
      • Built 2006
      1821 Hammerlin Ave Unit A, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

  • /20

    $375,000

    $25K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 913 Sq Ft

    2482 Roxbury Rd, Winter Park, FL 32789

    Under contract-accepting backup offers. Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready.But what truly sets this

    Gary Cohl COLDWELL BANKER REALTY

    2482 Roxbury Rd, Winter Park, FL 32789
  • /11

    Starting at $1,340

    Total Monthly Price

    • 1 - 2 Beds

    7502 Sun Key Blvd, Winter Park, FL 32792

    Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

    Solis at Winter Park

    7502 Sun Key Blvd, Winter Park, FL 32792
  • /2

    $245,000

    Sold Jun 26, 2025

    2471 Tahoe Cir, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft
    • Built 1981

    Last Sold Summary

    • 6% Below List Price
    • $189/SF
    • 84 Days On Market

    Current Estimated Value $244,960

    Last Listing Agent Kevin Wilhelm MLSB THE BUREAU POWERED BY CAROM REALTY

    2471 Tahoe Cir, Winter Park, FL 32792
    • /40

      Est $251,272

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,322 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792

      Last Sold Summary

      • 10 Days On Market

  • /26

    $449,990

    Pending
    • 3 Beds
    • 2 Baths
    • 1,534 Sq Ft

    5117 Cypress Ct, Winter Park, FL 32792

    Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully renovated home tucked away on a quiet cul-de-sac in Winter Park.Thoughtfully redesigned with a modern open-concept layout, this home offers an expansive single-story layout with over 1,500 square feet of inviting living space designed for both everyday living and effortless entertaining. From the moment you

    Kristin McIntosh EXP REALTY LLC

    5117 Cypress Ct, Winter Park, FL 32792
  • /29

    Starting at $1,438

    Total Monthly Price

    • 1 - 3 Beds

    3733 N Goldenrod Rd, Winter Park, FL 32792

    Welcome home to Atlas at Winter Park!

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
  • /2

    $400,000

    Sold Jul 16, 2025

    3443 Arnel Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,503 Sq Ft
    • Built 1967

    Last Sold Summary

    • 6% Below List Price
    • $266/SF
    • 15 Days On Market

    Current Estimated Value $402,735

    Last Listing Agent Lana More KELLER WILLIAMS WINTER PARK

    3443 Arnel Dr, Winter Park, FL 32792
    • /2

      Est $697,471

      Not Listed For Sale

      2602 Winter Park Rd, Winter Park, FL 32789

      • 3 Beds
      • 2 Baths
      • 1,966 Sq Ft
      • Built 1975
      2602 Winter Park Rd, Winter Park, FL 32789

      Last Sold Summary

      • 4 Days On Market

  • /26

    $265,000

    $20K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,495 Sq Ft

    2401 Sun Valley Cir, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the

    Jamie Vanosdol EXP REALTY LLC

    2401 Sun Valley Cir, Winter Park, FL 32792
  • /30

    Starting at $1,675 Per Month

    • 1 Bed

    520 N Orlando Ave, Winter Park, FL 32789

    Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

    The Lofts of Winter Park Village

    520 N Orlando Ave, Winter Park, FL 32789
  • /2

    $2,050,000

    Sold Apr 30, 2026

    1205 Mayfield Ave, Winter Park, FL 32789

    • Land
    • 23,958 Sq Ft
    • $3,727,273 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 89 Days On Market

    Current Estimated Value $2,208,348

    Last Listing Agent Abby Nelson RE/MAX 200 REALTY

    1205 Mayfield Ave, Winter Park, FL 32789
    • /28

      Est $337,672

      Not Listed For Sale

      4870 Seminole Ave, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1957
      4870 Seminole Ave, Winter Park, FL 32792

      Last Sold Summary

      • 32 Days On Market

  • /48

    $535,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 2,071 Sq Ft

    1232 Valley Creek Run, Winter Park, FL 32792

    Welcome to this beautifully maintained pool home in the highly desirable Lost Creek community, where comfort, functionality, and location come together perfectly. This spacious residence features three generously sized bedrooms and a thoughtfully designed floor plan offering both formal and casual living spaces, including a living room, formal dining room, and a large family room that flows

    James Clark CENTURY 21 ALTON CLARK

    1232 Valley Creek Run, Winter Park, FL 32792
  • /31

    Starting at $1,514 Per Month

    • 1 - 2 Beds

    800 Semoran Park Dr, Winter Park, FL 32792

    Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

    POSTE Winter Park

    800 Semoran Park Dr, Winter Park, FL 32792
  • /2

    $261,000

    Sold May 13, 2026

    1500 Gay Rd Unit 8D, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Below List Price
    • $254/SF
    • 19 Days On Market

    Current Estimated Value $264,210

    Last Listing Agent Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

    1500 Gay Rd Unit 8D, Winter Park, FL 32789
    • /22

      Est $5,501,810

      Not Listed For Sale

      300 S Interlachen Ave Unit 601, Winter Park, FL 32789

      • 4 Beds
      • 4.5 Baths
      • 5,430 Sq Ft
      • Built 2005
      300 S Interlachen Ave Unit 601, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

  • /71

    $685,000

    $15K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,702 Sq Ft

    3114 Heartleaf Place, Winter Park, FL 32792

    Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive,

    Nadia Kurakin CHAMPION HOMES

    3114 Heartleaf Place, Winter Park, FL 32792
  • /35

    Starting at $1,600 Per Month

    • Studio - 3 Beds

    433 W New England Ave, Winter Park, FL 32789

    We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

    Hannibal Square

    433 W New England Ave, Winter Park, FL 32789
  • /2

    $440,000

    Sold Jan 29, 2026

    1621 Puritan Ave, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,765 Sq Ft
    • Built 1963

    Last Sold Summary

    • 12% Below List Price
    • $249/SF
    • 342 Days On Market

    Current Estimated Value $435,235

    Last Listing Agent Alejandro Colon PREFERRED REAL ESTATE BROKERS

    1621 Puritan Ave, Winter Park, FL 32792
    • /2

      Est $2,738,184

      Not Listed For Sale

      1737 Lookout Landing Cir, Winter Park, FL 32789

      • 5 Beds
      • 5.5 Baths
      • 5,066 Sq Ft
      • Built 2013
      1737 Lookout Landing Cir, Winter Park, FL 32789

      Last Sold Summary

      • 232 Days On Market

Showing Results 81 - 120, Page 3 of 18

How to Buy a Home How to Finance a Home How to Sell a Home