28,401

Winter Park, FL Homes

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  • /50

    $825,000

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,020 Sq Ft

    1287 Verdant Glade Place, Winter Park, FL 32792

    **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 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    1287 Verdant Glade Place, 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

    $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

  • /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
  • /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

    $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
  • /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

    $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

  • /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
  • /6

    $3,000

    Total Monthly Price

    • 2 Beds
    • 2.5 Baths
    • 1,100 Sq Ft
    • Townhouse for Rent

    1144 Washington Ave, Winter Park, FL 32789

    Fully remodeled 2 BR, 2.5 BA townhouse in a wonderful location of Winter Park. 1 block from the Winter Park Tennis Center, walking distance to Rollins College and Park Ave. The townhouse is tucked into a quiet neighborhood known as The Quarters. New Kitchen, Appliances, cabinets and fixtures. New carpeting, and hard wood floors throughout. All three bathrooms have been remodel with new vanities

    1144 Washington Ave, Winter Park, FL 32789
  • /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

  • /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 $1,058 Per Month

    • Studio - 3 Beds

    300 Jamestown Dr, Winter Park, FL 32792

    Carlton Arms of Winter Park is a well established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff. We offer an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

    Carlton Arms of Winter Park

    300 Jamestown Dr, 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

  • /22

    $190,000

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft

    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792

    TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a functional open layout perfect for everyday living or investment potential. Step inside to find a bright and airy living and dining area with sliding glass doors leading to a private screened-in balcony — the perfect spot to relax and enjoy the

    Steven Pugh EXP REALTY LLC

    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
  • /30

    Starting at $1,972

    Total Monthly Price

    • 1 - 2 Beds

    3045 Aloma Ave, Winter Park, FL 32792

    Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar-all with an attentive team at your

    Rosalia Winter Park 55+ Active Adult Community

    3045 Aloma Ave, 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

  • /42

    $598,000

    $26K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,620 Sq Ft

    1822 Yorkshire Dr, Winter Park, FL 32792

    Virtually Staged. PRICE REDUCTION...priced to move! Charming three-bedroom, three-bath one-story home features a split floor plan with two primary suites, ideal for multigenerational living or guest flexibility, in a prime Winter Park location. In the desirable Park Manor subdivision, this beautifully designed split floor plan home offers comfort and privacy, perfect for modern living. Enjoy the

    MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

    1822 Yorkshire Dr, Winter Park, FL 32792
  • /27

    Starting at $1,154

    Total Monthly Price

    • Studio - 3 Beds

    1701 Lee Rd, Winter Park, FL 32789

    There's no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the

    Westmount at Winter Park

    1701 Lee Rd, Winter Park, FL 32789
  • /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

  • /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
  • /30

    Starting at $1,275 Per Month

    • 1 - 3 Beds

    2500 Howell Branch Rd, Winter Park, FL 32792

    Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

    Signal Pointe

    2500 Howell Branch Rd, Winter Park, FL 32792
  • /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

  • /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
  • /35

    Starting at $1,141 Per Month

    • 2 - 3 Beds

    7701 Acorn Woods Cir, Winter Park, FL 32792

    Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

    Golden Oaks

    7701 Acorn Woods Cir, 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

  • /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
  • /24

    Starting at $1,481 Per Month

    • 1 - 2 Beds

    3935 Sutton Place Blvd, Winter Park, FL 32792

    Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

    Alvista Winter Park

    3935 Sutton Place Blvd, Winter Park, FL 32792
  • /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

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