28,224

Winter Park, FL Homes

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  • /20

    $172,000

    $3K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 990 Sq Ft

    3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792

    Welcome to this beautifully maintained 2-bedroom, 1.5-bathroom townhouse-style condominium located in the desirable Hidden Oaks Condominium community. This charming unit features a spacious living and dining area with tile flooring throughout the first floor, along with a well-appointed kitchen, breakfast nook, and convenient indoor laundry room. The home has been freshly updated with new

    Jessie Lin SOGO REAL ESTATE SERVICES LLC

    3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792
  • /9

    $2,015 Per Month

    • 3 Beds
    • 2 Baths
    • 1,175 Sq Ft
    • Condo for Rent

    2711 Aloma Ave, Winter Park, FL 32792

    Welcome home to 2711 Aloma Avenue — a 3-bedroom, 2-bathroom unit offering 1,175 square feet in the Winter Park area near Orlando. This home offers a comfortable, well-proportioned layout convenient to Aloma Avenue shopping, dining, and easy access to major roadways for commuting throughout the greater Orlando area. Pet-friendly with a pet fee. For applications or to schedule a viewing, please

    2711 Aloma Ave, Winter Park, FL 32792
  • /2

    $1,206,400

    Sold Oct 15, 2025

    4048 Gilder Rose Place, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,321 Sq Ft
    • Built 1992

    Last Sold Summary

    • $363/SF
    • 101 Days On Market

    Current Estimated Value $1,186,317

    Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

    4048 Gilder Rose Place, Winter Park, FL 32792
    • /2

      Est $459,623

      Not Listed For Sale

      1596 Little Wren Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,964 Sq Ft
      • Built 2020
      1596 Little Wren Ln, Winter Park, FL 32792

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Nohora Gomez COLDWELL BANKER REALTY

  • /22

    $660,000

    • 3 Beds
    • 3 Baths
    • 1,690 Sq Ft

    1256 Melissa Ct, Winter Park, FL 32789

    Very well maintained townhouse great location in Waterbridge on cul-de-sac near tennis courts. This 2 bedroom/den or 3 bedroom , 3 bathroom with primary upstairs and additional bedroom on main floor is renovated with hardwood floors downstairs, updated recessed lighting throughout, updated plumbing, volume ceilings, great ambient light and windows, barrel tile roof. Kitchen with updated

    Wesley Morales KELLER WILLIAMS REALTY AT THE PARKS

    1256 Melissa Ct, Winter Park, FL 32789
  • /32

    $2,100 Per Month

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • House for Rent

    5212 N Indiana Ave, Winter Park, FL 32792

    Welcome to this beautifully remodeled 1,000-square-foot Mid-Century Modern home offering the perfect blend of timeless design and modern updates. This charming residence features 3 spacious bedrooms and 1.5 updated bathrooms, creating a comfortable and functional layout for everyday living. The heart of the home is the stunning new kitchen, showcasing crisp white shaker cabinets, elegant quartz

    Edward Diamond CREEGAN GROUP

    5212 N Indiana Ave, Winter Park, FL 32792
  • /2

    $487,500

    Sold Mar 26, 2026

    275 N Ranger Blvd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,864 Sq Ft
    • Built 1965

    Last Sold Summary

    • 2% Below List Price
    • $262/SF
    • 2 Days On Market

    Current Estimated Value $734,852

    Last Listing Agent David Augello ON POINT REALTY LLC

    275 N Ranger Blvd, Winter Park, FL 32792
    • /2

      Est $496,839

      Not Listed For Sale

      1303 Merrydale Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,312 Sq Ft
      • Built 2021
      1303 Merrydale Way, Winter Park, FL 32792

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  • /33

    $649,000

    $20K PRICE DROP Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,107 Sq Ft

    1409 Sunset Dr, Winter Park, FL 32789

    Under contract-accepting backup offers. LOCATION. LIFESTYLE. TIMELESS WINTER PARK CHARM. Discover an exceptional opportunity in Lake Knowles Terrace, where classic character, effortless comfort, and an enviable location come together beautifully.From the moment you arrive, the home makes an unforgettable first impression with charming curb appeal, elegant walkways, a brick-paver driveway, and

    TJ Tuzzeo KONA REALTY SERVICES LLC

    1409 Sunset Dr, Winter Park, FL 32789
  • /18

    $1,890 Per Month

    • 2 Beds
    • 1 Bath
    • 1,150 Sq Ft
    • House for Rent

    2510 Roxbury Rd, Winter Park, FL 32789

    This beautifully renovated half-duplex is just blocks from Lake Killarney, ideally situated between College Park and the Winter Park shopping district. Enjoy quick access to local favorites like the Orlando Science Center, Winter Park Village, and Mead Gardens—all just minutes away.The home features 2 bedrooms, 1 bathroom, and a dedicated carport for convenient parking. Inside, you'll

    2510 Roxbury Rd, Winter Park, FL 32789
  • /2

    $630,000

    Sold Apr 16, 2026

    649 Berwick Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,943 Sq Ft
    • Built 1966

    Last Sold Summary

    • 3% Above List Price
    • $324/SF
    • 3 Days On Market

    Current Estimated Value $621,986

    Last Listing Agent Caroline Fiore MAINFRAME REAL ESTATE

    649 Berwick Dr, Winter Park, FL 32792
    • /2

      Est $1,372,383

      Not Listed For Sale

      1733 Harmon Ave, Winter Park, FL 32789

      • 5 Beds
      • 4.5 Baths
      • 3,267 Sq Ft
      • Built 2025
      1733 Harmon Ave, Winter Park, FL 32789

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  • /24

    $309,900

    • 3 Beds
    • 2.5 Baths
    • 1,545 Sq Ft

    7530 Cranes Creek Ct, Winter Park, FL 32792

    Welcome home to this inviting 3-bedroom, 2.5-bath townhome offering a comfortable floor plan and several recent updates. All three bedrooms are conveniently located on the second floor and feature newly installed carpet, providing a fresh and comfortable feel.The main living areas feature easy-care ceramic tile throughout the living room and dining room, as well as in the bathrooms. The

    Edward Hru ROO REALTY LLC

    7530 Cranes Creek Ct, Winter Park, FL 32792
  • /19

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1942 Conifer Ct, Winter Park, FL 32792

    Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a table with 4 chairs - picnic in your own park

    Scott Banta BLACKFIN REALTY LLC

    1942 Conifer Ct, Winter Park, FL 32792
  • /2

    $168,500

    Sold Jul 02, 2026

    1500 Gay Rd Unit 5, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 732 Sq Ft
    • Built 1972

    Last Sold Summary

    • 14% Below List Price
    • $230/SF
    • 97 Days On Market

    Last Listing Agent Jacob Hara TRANSCEND REALTY

    1500 Gay Rd Unit 5, Winter Park, FL 32789
    • /2

      Est $382,702

      Not Listed For Sale

      740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 1,536 Sq Ft
      • Built 1986
      740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

      Last Sold Summary

      • 171 Days On Market

      Last Listing Agent Michael O'Shaughnessy MICHAEL O'SHAUGHNESSY, INC.

  • /30

    $629,900

    $195K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,472 Sq Ft

    2612 Roxbury Rd, Winter Park, FL 32789

    RENT TO OWN OPTION AVAILABLE!!!Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper —

    Laura Mcadams EXP REALTY LLC

    2612 Roxbury Rd, Winter Park, FL 32789
  • /16

    $2,200 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,277 Sq Ft
    • 3 Bedroom Pet-Friendly Home in Winter Park, FL with Main Street Renewal

    2866 Euston Rd, Winter Park, FL 32789

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location,

    2866 Euston Rd, Winter Park, FL 32789
  • /2

    $625,090

    Sold Jun 03, 2026

    2713 Eastern Pkwy, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Below List Price
    • $479/SF
    • 12 Days On Market

    Current Estimated Value $647,558

    Last Listing Agent Helen Thompson RE/MAX SELECT GROUP

    2713 Eastern Pkwy, Winter Park, FL 32789
    • /2

      Est $217,971

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 1402, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,165 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 1402, Winter Park, FL 32792

      Last Sold Summary

      • 134 Days On Market

      Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

  • /28

    $475,000

    • 2 Beds
    • 2 Baths
    • 1,438 Sq Ft

    2824 Prince John Rd, Winter Park, FL 32792

    Welcome to this charming 2 bedroom, 2 bath home, with light and bright open floor plan, spacious rooms and many updates and upgrades. Roof was replaced (2019), new A/C (8/26), fully renovated kitchen with quartz counters, cabinetry, and stainless appliances. Pella double pane windows (2020), new French doors and interior doors, and new soffits and gutters in 2025. Enjoy outdoor living in the

    Joan Cross BHHS FLORIDA REALTY

    2824 Prince John Rd, Winter Park, FL 32792
  • /19

    $1,850 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    2481 Tahoe Cir Unit 42481, Winter Park, FL 32792

    Welcome to Cedarwood Village, a spacious 2-bedroom, 2-bath and upstairs loft condominium with approximately 1,495 square feet of living space, ideally located in Winter Park. Tucked within an established community surrounded by mature trees, this residence offers a comfortable layout with plenty of flexibility for everyday living. The inviting living and dining area provides generous space for

    sebastian Lozano COLDWELL BANKER REALTY

    2481 Tahoe Cir Unit 42481, Winter Park, FL 32792
  • /2

    $637,500

    Sold Jan 16, 2026

    595 Huntington Ave Unit 4, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,951 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $327/SF
    • 149 Days On Market

    Current Estimated Value $638,985

    Last Listing Agent Andrew Livingston COLDWELL BANKER REALTY

    595 Huntington Ave Unit 4, Winter Park, FL 32789
    • /2

      Est $210,380

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792

      • 2 Beds
      • 1.5 Baths
      • 1,219 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

  • /25

    $284,900

    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft

    2335 Inagua Way, Winter Park, FL 32792

    Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

    Marion McGrath ABSOLUTE REALTY GROUP, LLC

    2335 Inagua Way, Winter Park, FL 32792
  • /20

    $3,795 Per Month

    • 3 Beds
    • 3 Baths
    • 1,715 Sq Ft
    • House for Rent

    1667 Mizell Ave, Winter Park, FL 32789

    Minimum Deposit $3795. Monthly Rent $3795. AvailableNOW!Contact Polina at or email to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established.Welcome to your dream Winter Park home! This charming 3-bedroom, 3 full bathroom gem is the epitome of comfort and style.

    1667 Mizell Ave, Winter Park, FL 32789
  • /2

    $1,250,000

    Sold Dec 29, 2025

    359 Beloit Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,395 Sq Ft
    • Built 1979

    Last Sold Summary

    • $522/SF
    • 0 Days On Market

    Current Estimated Value $1,276,215

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    359 Beloit Ave, Winter Park, FL 32789
    • /2

      Est $508,000

      Not Listed For Sale

      1632 Haven Dr, Orlando, FL 32803

      • 3 Beds
      • 2.5 Baths
      • 1,772 Sq Ft
      • Built 2025
      1632 Haven Dr, Orlando, FL 32803

      Last Sold Summary

      • 110 Days On Market

      Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  • /20

    $375,000

    $25K PRICE DROP Under Contract
    • 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
  • /27

    $1,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • Townhouse for Rent

    3220 Oak Lawn Place Unit 210, Winter Park, FL 32792

    This beautiful corner-unit townhouse offers comfort, space, and convenience in a highly desirable location. This home features 3 bedrooms and 2.5 bathrooms, providing plenty of space for families and professionals. The kitchen flows seamlessly into the living, dining áreas and private patio offering a practical design for everyday living. All bedrooms are located upstairs for added privacy,

    Nelly Kilzi de Khabaze AGENT TRUST REALTY CORPORATION

    3220 Oak Lawn Place Unit 210, Winter Park, FL 32792
  • /2

    $775,000

    Sold May 22, 2026

    521 Fairfax Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 2,112 Sq Ft
    • Built 1955

    Last Sold Summary

    • 2% Below List Price
    • $367/SF
    • 2 Days On Market

    Current Estimated Value $775,190

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    521 Fairfax Ave, Winter Park, FL 32789
    • /2

      Not Listed For Sale

      1630 Haven Dr, Orlando, FL 32803

      • 3 Beds
      • 2.5 Baths
      • 1,668 Sq Ft
      • Built 2024
      1630 Haven Dr, Orlando, FL 32803

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  • /35

    $649,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,101 Sq Ft

    1037 N Virginia Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street. Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. New roof and water heater 2023, refinished hardwood floors,

    Lisa Gould KELLER WILLIAMS WINTER PARK

    1037 N Virginia Ave, Winter Park, FL 32789
  • /14

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 805 Sq Ft
    • Townhouse for Rent

    1618 Indiana Ave, Winter Park, FL 32789

    Minimum Deposit $1800. Rent $1800. Water and Lawncare Included in rent price!Set on a friendly street in the heart of Winter Park, this freshly remodeled duplex delivers easy, low-maintenance living in one of Central Florida's most sought-after zip codes. Inside, 805 square feet of thoughtfully refreshed space welcomes you with brand-new appliances, a crisp new A/C system, and a casual

    1618 Indiana Ave, Winter Park, FL 32789
  • /2

    $1,199,000

    Sold Jun 09, 2026

    1807 Magnolia Ave, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 2,618 Sq Ft
    • Built 2026

    Last Sold Summary

    • $458/SF
    • 9 Days On Market

    Current Estimated Value $1,172,211

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1807 Magnolia Ave, Winter Park, FL 32789
    • /2

      Est $1,400,490

      Not Listed For Sale

      1830 Pineview Cir, Winter Park, FL 32792

      • 4 Beds
      • 3.5 Baths
      • 2,843 Sq Ft
      • Built 2024
      1830 Pineview Cir, Winter Park, FL 32792

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

  • /23

    $242,400

    $18K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 956 Sq Ft

    2500 Lee Rd Unit 104, Winter Park, FL 32789

    Price improvement! Move-in ready in Winter Park 32789. This beautifully renovated first-floor 2-bedroom, 2-bath condo features an open layout, custom soft-close cabinetry, high-end quartzite countertops, sleek matching appliances, and stylishly updated bathrooms, including a primary bath with elegant Italian porcelain tile. Major upgrades include a NEW A/C system and air handler and NEW tankless

    Stephen Hachey FLAT FEE MLS REALTY

    2500 Lee Rd Unit 104, Winter Park, FL 32789
  • /2

    $2,500 Per Month

    • Property for Rent

    Unlisted Address

    Rare Winter Park Lakefront Boathouse - $2,500/Month Experience the quintessential Central Florida lifestyle in this exceptional boathouse rental on the renowned Winter Park Chain of Lakes. This direct lakefront property offers unparalleled access to year-round water activities, from kayaking and paddleboarding to boating and fishing right from your doorstep. Positioned just off the scenic

    Kelly Price KELLY PRICE & COMPANY LLC

    Unlisted Address
  • /2

    $1,095,000

    Sold Dec 01, 2025

    1450 Chestnut Ave, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,942 Sq Ft
    • Built 2009

    Last Sold Summary

    • 16% Below List Price
    • $564/SF
    • 49 Days On Market

    Current Estimated Value $1,130,622

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1450 Chestnut Ave, Winter Park, FL 32789
    • /2

      Not Listed For Sale

      255 Sandlewood Trail, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 960 Sq Ft
      • Built 1984
      255 Sandlewood Trail, Winter Park, FL 32789

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Freddie Crespo INVESTOR'S REAL ESTATE LLC

Showing Results 401 - 440, Page 11 of 18

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