28,400

Winter Park, FL Homes

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  • /52

    $1,150,000

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

    1981 Blue Ridge Rd, Winter Park, FL 32789

    Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    1981 Blue Ridge Rd, Winter Park, FL 32789
  • /131

    Starting at $1,295 Per Month

    • 1 - 3 Beds

    541 Oak Reserve Ln, Winter Park, FL 32792

    Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

    Oak Reserve at Winter Park

    541 Oak Reserve Ln, Winter Park, FL 32792
  • /2

    $374,900

    Sold Oct 10, 2025

    2028 Leanne Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft
    • Built 1968

    Last Sold Summary

    • $244/SF
    • 9 Days On Market

    Last Listing Agent Jamie Ampel ALL SELLERS & BUYERS REALTY INC

    2028 Leanne Ct, Winter Park, FL 32792
    • /26

      Est $479,383

      Not Listed For Sale

      2469 Firstlight Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,308 Sq Ft
      • Built 2019
      2469 Firstlight Way, Winter Park, FL 32792

      Last Sold Summary

      • 58 Days On Market

  • /37

    $835,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft

    1090 Wildmeadow Run, Winter Park, FL 32792

    Virtually Staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity. Ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This off-grid solar system comes with a WHOLE HOUSE BATTERY BACKUP, keeping your lights on

    Agent Photo

    Rod Chevalier

    BHHS FLORIDA REALTY

    1090 Wildmeadow Run, Winter Park, FL 32792
  • /50

    Starting at $1,593 Per Month

    • Studio - 3 Beds

    1874 Harmon Ave, Winter Park, FL 32789

    Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

    Berkshire Winter Park

    1874 Harmon Ave, Winter Park, FL 32789
  • /2

    $1,200,000

    Sold May 29, 2026

    3711 Vinsetta Ct, Winter Park, FL 32792

    • 6 Beds
    • 4 Baths
    • 4,214 Sq Ft
    • Built 2015

    Last Sold Summary

    • 20% Below List Price
    • $285/SF
    • 75 Days On Market

    Current Estimated Value $1,325,347

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    3711 Vinsetta Ct, Winter Park, FL 32792
    • /47

      Est $1,067,798

      Not Listed For Sale

      1939 Woodcrest Dr, Winter Park, FL 32792

      • 4 Beds
      • 3.5 Baths
      • 2,575 Sq Ft
      • Built 2020
      1939 Woodcrest Dr, Winter Park, FL 32792

      Last Sold Summary

      • 2 Days On Market

  • /48

    $625,000

    Open Sun 1AM - 3PM $55K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,287 Sq Ft

    1830 Edwin Blvd, Winter Park, FL 32789

    Virtually Staged. *** JUST REDUCED TO $625,000 | 1830 Edwin Blvd, Winter Park, FL 32789*** This is your moment. One of Winter Park's most beautifully RENOVATED and MOVE-IN READY homes has just been repriced, and at $625,000, it will not last long. From the moment you step inside, you are welcomed by an open, airy layout with soaring VAULTED CEILINGS that make the home feel expansive and inviting.

    Agent Photo

    Nydia Marrero

    ZEN LIVING HOMES LLC

    1830 Edwin Blvd, Winter Park, FL 32789
  • /44

    Starting at $1,063 Per Month

    • Studio - 3 Beds

    4755 N Goldenrod Rd, Winter Park, FL 32792

    Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

    Liv at Winter Park Apartment Homes

    4755 N Goldenrod Rd, Winter Park, FL 32792
  • /2

    $2,295,000

    Sold Dec 16, 2025

    1661 Palm Ave, Winter Park, FL 32789

    • 4 Beds
    • 6 Baths
    • 3,570 Sq Ft
    • Built 2025

    Last Sold Summary

    • 12% Below List Price
    • $643/SF
    • 26 Days On Market

    Current Estimated Value $2,201,722

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    1661 Palm Ave, Winter Park, FL 32789
    • /2

      Est $185,720

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 1,127 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 1603, Winter Park, FL 32792

      Last Sold Summary

      • 38 Days On Market

  • /63

    $230,000

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

    7488 Whisperwood Dr Unit 28, Winter Park, FL 32792

    Welcome to Whisperwood, where space, convenience, and investment potential come together in one exceptional opportunity.This rare gem is a beautifully maintained 2-bedroom, 2.5-bath residence offering a rarely available townhome-style floor plan that combines generous living spaces, exceptional functionality, and outstanding investment potential. The spacious multi-level layout features

    Agent Photo

    Miranda Azer

    PARKVIEW REAL ESTATE

    7488 Whisperwood Dr Unit 28, Winter Park, FL 32792
  • /50

    Starting at $1,852 Per Month

    • Studio - 3 Beds

    1305 Morgan Stanley Ave, Winter Park, FL 32789

    Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

    Juno Winter Park

    1305 Morgan Stanley Ave, Winter Park, FL 32789
  • /2

    $2,700,000

    Sold Oct 30, 2025

    1020 Mayfield Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,663 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $1,014/SF
    • 149 Days On Market

    Current Estimated Value $2,787,254

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    1020 Mayfield Ave, Winter Park, FL 32789
    • /2

      Est $261,641

      Not Listed For Sale

      7148 Swallow Run Unit E1, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,565 Sq Ft
      • Built 2008
      7148 Swallow Run Unit E1, Winter Park, FL 32792

      Last Sold Summary

      • 21 Days On Market

  • /56

    $315,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft

    5894 Shale Ct, Winter Park, FL 32792

    Under contract-accepting backup offers. **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.** Talk about location, location, location! Welcome to this beautifully updated and well-maintained 2-bedroom, 2-bathroom, 1-car garage home in Winter Park, perfectly situated in the

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    5894 Shale Ct, Winter Park, FL 32792
  • /50

    Starting at $1,930 Per Month

    • 1 - 3 Beds

    940 W Canton Ave, Winter Park, FL 32789

    Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

    Paseo at Winter Park Village

    940 W Canton Ave, Winter Park, FL 32789
  • /2

    $714,000

    Sold Mar 12, 2026

    636 Dunblane Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,803 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Below List Price
    • $396/SF
    • 7 Days On Market

    Current Estimated Value $704,388

    Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    636 Dunblane Dr, Winter Park, FL 32792
    • /2

      Est $282,248

      Not Listed For Sale

      222 Balfour Dr Unit 14, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,256 Sq Ft
      • Built 1985
      222 Balfour Dr Unit 14, Winter Park, FL 32792

      Last Sold Summary

      • 206 Days On Market

  • /46

    $475,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,645 Sq Ft

    3641 Oak Vista Ln, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to Winter Park. VIEW VIRTUAL TOUR! The Original Owner has meticulously cared for this home and the pride of ownership shines through. The real showstopper is your private outdoor oasis! Enjoy Florida’s endless sunshine in the expansive, screened-in back porch and pool area—perfect for year-round gatherings, pool parties, and quiet weekends at home.

    Agent Photo

    Laurie Cain

    CHARLES RUTENBERG REALTY ORLANDO

    3641 Oak Vista Ln, Winter Park, FL 32792
  • /50

    Starting at $1,093 Per Month

    • 1 - 3 Beds

    349 Scottsdale Square, Winter Park, FL 32792

    This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

    Winter Park Woods Apartments

    349 Scottsdale Square, Winter Park, FL 32792
  • /2

    $581,000

    Sold May 26, 2026

    7917 Pleasant Pine Cir, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,157 Sq Ft
    • Built 2014

    Last Sold Summary

    • 3% Below List Price
    • $269/SF
    • 0 Days On Market

    Current Estimated Value $589,421

    Last Listing Agent Lori Gilmore LORI GILMORE REAL ESTATE LLC

    7917 Pleasant Pine Cir, Winter Park, FL 32792
    • /2

      Est $2,789,534

      Not Listed For Sale

      1618 Holts Grove Cir, Winter Park, FL 32789

      • 5 Beds
      • 8 Baths
      • 4,807 Sq Ft
      • Built 2014
      1618 Holts Grove Cir, Winter Park, FL 32789

      Last Sold Summary

      • 173 Days On Market

  • /31

    $380,000

    Pending
    • 2 Beds
    • 1 Bath
    • 988 Sq Ft

    440 Cambridge Blvd, Winter Park, FL 32789

    Under contract-accepting backup offers. **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 to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    440 Cambridge Blvd, Winter Park, FL 32789
  • /35

    Starting at $1,199 Per Month

    • 1 - 3 Beds

    3207 Rosebud Ln, Winter Park, FL 32792

    These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

    Summerlin at Winter Park Apartments

    3207 Rosebud Ln, Winter Park, FL 32792
  • /2

    $354,900

    Sold May 15, 2026

    5330 Tangerine Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,642 Sq Ft
    • Built 1976

    Last Sold Summary

    • $216/SF
    • 0 Days On Market

    Current Estimated Value $355,785

    Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

    5330 Tangerine Ave, Winter Park, FL 32792
    • /33

      Est $799,170

      Not Listed For Sale

      1316 Fountain Hills Ct, Winter Park, FL 32792

      • 4 Beds
      • 3.5 Baths
      • 2,823 Sq Ft
      • Built 2018
      1316 Fountain Hills Ct, Winter Park, FL 32792

      Last Sold Summary

      • 138 Days On Market

  • /36

    $419,900

    Open Fri 2:30PM - 3PM $60K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,770 Sq Ft

    3463 Arnel Dr, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. DO NOT MISS THIS OPPORTUNITY! PRICE IMPROVEMENT + Pool Home + Paid-Off Solar Panels + No HOA in Winter Park! Welcome to this move-in-ready 3-bedroom, 2-bathroom home with approximately 1,770 square feet of living space, a 2-car garage, and a private pool, all located in the established Eastbrook community. Roof replaced in 2018, fully paid-off solar

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    3463 Arnel Dr, Winter Park, FL 32792
  • /39

    Starting at $910 Per Month

    • 1 - 3 Beds

    2353 Winter Woods Blvd, Winter Park, FL 32792

    Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

    San Jose Apartments

    2353 Winter Woods Blvd, Winter Park, FL 32792
  • /2

    $638,250

    Sold Sep 02, 2025

    1536 Golfside Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1980

    Last Sold Summary

    • $338/SF
    • 3 Days On Market

    Current Estimated Value $649,392

    Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    1536 Golfside Dr, Winter Park, FL 32792
    • /2

      Est $1,855,793

      Not Listed For Sale

      1411 Border Dr, Winter Park, FL 32789

      • 4 Beds
      • 6 Baths
      • 4,638 Sq Ft
      • Built 2019
      1411 Border Dr, Winter Park, FL 32789

      Last Sold Summary

      • 195 Days On Market

  • /26

    $399,900

    • 4 Beds
    • 2 Baths
    • 1,979 Sq Ft

    3949 Cool Water Ct, Winter Park, FL 32792

    Located on a quiet cul-de-sac in Winter Park, this home has the kind of layout and lot that are hard to find at this price point. Vaulted ceilings open up the main living area, and built-in display niches along the wall give the space character you won't find in newer construction. The kitchen has a breakfast bar peninsula and connects to a sunny dining space with a pendant light overhead. The

    Agent Photo

    Regan Jackson

    ACME REAL ESTATE FLORIDA LLC

    3949 Cool Water Ct, Winter Park, FL 32792
  • /50

    Starting at $1,585 Per Month

    • Studio - 2 Beds

    741 Clay St, Winter Park, FL 32789

    Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

    Seven41 Winter Park

    741 Clay St, Winter Park, FL 32789
  • /2

    $401,000

    Sold Oct 15, 2025

    1809 Palmer Ave, Winter Park, FL 32792

    • Land
    • 9,147 Sq Ft
    • $1,909,524 per Acre

    Last Sold Summary

    • 5 Days On Market

    Current Estimated Value $399,359

    Last Listing Agent Christina Munkberg COLDWELL BANKER REALTY

    1809 Palmer Ave, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      700 Melrose Ave Unit G, Winter Park, FL 32789

      • 1 Bed
      • 1 Bath
      • 687 Sq Ft
      • Built 1964
      700 Melrose Ave Unit G, Winter Park, FL 32789

      Last Sold Summary

      • 73 Days On Market

  • /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
  • /50

    Starting at $1,614 Per Month

    • 1 - 2 Beds

    3924 Calibre Bend Ln, Winter Park, FL 32792

    Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

    Calibre Bend Apartments

    3924 Calibre Bend Ln, Winter Park, FL 32792
  • /2

    $4,250,000

    Sold Jun 01, 2026

    1336 College Point, Winter Park, FL 32789

    • 4 Beds
    • 5 Baths
    • 3,181 Sq Ft
    • Built 1926

    Last Sold Summary

    • 8% Below List Price
    • $1,336/SF
    • 109 Days On Market

    Current Estimated Value $4,442,314

    Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1336 College Point, Winter Park, FL 32789
    • /31

      Est $186,087

      Not Listed For Sale

      3307 Amber Wood Way Unit 106, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,031 Sq Ft
      • Built 1983
      3307 Amber Wood Way Unit 106, Winter Park, FL 32792

      Last Sold Summary

      • 16 Days On Market

Showing Results 41 - 80, Page 2 of 18

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