28,401

Winter Park, FL Homes

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  • /41

    $549,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,930 Sq Ft

    4053 Cool Water Ct, Winter Park, FL 32792

    POOL HOME WITH A WOOD-BURNING FIREPLACE, HOME OFFICE, AND PRIME WINTER PARK LOCATION! This single-family home is packed with the features today's buyers are looking for, including a private pool, spacious backyard, dedicated office/den, and a cozy wood-burning fireplace. Inside, you'll find a versatile floor plan designed for both everyday living and entertaining. The family room is warm and

    Aarohi Shah ALIGN REAL ESTATE LLC

    4053 Cool Water Ct, Winter Park, FL 32792
  • /19

    $1,450 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Condo for Rent

    3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792

    Beautiful 2-bedroom, 2-bath condo available for rent in the highly desirable Winter Park area. This inviting home is thoughtfully designed for comfortable family living and features no carpet, with durable laminate flooring throughout perfect for easy cleaning and everyday use. The condo offers a spacious and functional layout, including a bright living area ideal for family time and

    Praveen Setty RIGHTHOUSE REALTY LLC

    3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
  • /2

    $468,000

    Sold Aug 28, 2025

    541 London Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,899 Sq Ft
    • Built 1965

    Last Sold Summary

    • $246/SF
    • 8 Days On Market

    Current Estimated Value $496,066

    Last Listing Agent Christopher Bauman REVEL REALTY LLC

    541 London Rd, Winter Park, FL 32792
    • /7

      Est $91,018

      Not Listed For Sale

      7309 Daniel Webster Dr Unit B, Winter Park, FL 32792

      • Studio
      • 1 Bath
      • 590 Sq Ft
      • Built 1974
      7309 Daniel Webster Dr Unit B, Winter Park, FL 32792

      Last Sold Summary

      • 44 Days On Market

  • /22

    $1,795,000

    New Construction
    • 4 Beds
    • 4 Baths
    • 2,819 Sq Ft

    2501 Lafayette Ave, Winter Park, FL 32789

    Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by curated design firm - Catalyst Design, with 25-year experience and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one.

    Michael Elias CHARLES RUTENBERG REALTY ORLANDO

    2501 Lafayette Ave, Winter Park, FL 32789
  • /9

    $2,015 Per Month

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

    2711 Aloma Ave, Winter Park, FL 32792

    Coming Soon!!To schedule a showing or for applications, please visit our website:www.keystone-By submitting your information on this page you consent to being contacted by the Property Manager and RentEngine via SMS, phone, or email.

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

    $710,000

    Sold Apr 01, 2026

    630 Saint Dunstan Way, Winter Park, FL 32792

    • 5 Beds
    • 2 Baths
    • 2,240 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Above List Price
    • $317/SF
    • 5 Days On Market

    Current Estimated Value $704,942

    Last Listing Agent Melissa Johnson EXP REALTY LLC

    630 Saint Dunstan Way, Winter Park, FL 32792
    • /2

      Est $1,040,055

      Not Listed For Sale

      311 E Morse Blvd Unit 6-18, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 2,096 Sq Ft
      • Built 1960
      311 E Morse Blvd Unit 6-18, Winter Park, FL 32789

      Last Sold Summary

      • 102 Days On Market

  • /41

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft

    5331 Oak Ct, Winter Park, FL 32792

    Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

    Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

    5331 Oak Ct, Winter Park, FL 32792
  • /16

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 964 Sq Ft
    • Townhouse for Rent

    3254 Howell Branch Rd, Winter Park, FL 32792

    This charming 2-bedroom, 2-bath duplex is ready for immediate move-in, offering a warm and inviting atmosphere for comfortable living. Step inside to discover a thoughtfully designed space with tile flooring throughout, providing both durability and easy maintenance. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances and solid-surface countertops. This

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    3254 Howell Branch Rd, Winter Park, FL 32792
  • /2

    $360,000

    Sold Mar 27, 2026

    7213 Silver Place, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $288/SF
    • 3 Days On Market

    Current Estimated Value $365,172

    Last Listing Agent Michael Rogers INNOVATIVE REALTY, LLC

    7213 Silver Place, Winter Park, FL 32792
    • /36

      Est $1,403,530

      Not Listed For Sale

      1405 Chapman Cir Unit OR, Winter Park, FL 32789

      • 3 Beds
      • 4 Baths
      • 2,950 Sq Ft
      • Built 2007
      1405 Chapman Cir Unit OR, Winter Park, FL 32789

      Last Sold Summary

      • 2 Days On Market

  • /27

    $154,500

    $15K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 990 Sq Ft

    3282 Oak Lake Place, Winter Park, FL 32792

    New Price! This beautifully updated 2-story condo offers the perfect blend of style and affordability. Featuring a fresh kitchen, renovated bathroom, and new flooring throughout, this move-in-ready home includes an in-unit washer/dryer for ultimate convenience. As a desirable end unit, you’ll enjoy extra privacy and a peaceful view of the adjacent conservation area. Relax on your private patio,

    Chad Busby BUSBY REALTY LLC

    3282 Oak Lake Place, Winter Park, FL 32792
  • /15

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,852 Sq Ft
    • Winter Park 3/2 Rental

    521 Ohio St, Winter Park, FL 32789

    WINTER PARK! 3 bedroom/2 bathroom single family home blocks from I-4. Newer luxury vinyl floors installed throughout home. Stainless steel refrigerator and range, new SS dishwasher, separate dining room, family room, living room, and 2 bonus rooms for offices or storage. 2-car carport with private drive. Big yard (1/3 acre lot) corner lot, rear patio. Inside laundry room with washer / dryer

    521 Ohio St, Winter Park, FL 32789
  • /2

    $935,000

    Sold Dec 19, 2025

    7706 Waunatta Ct, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 3,858 Sq Ft
    • Built 1978

    Last Sold Summary

    • 11% Below List Price
    • $242/SF
    • 70 Days On Market

    Current Estimated Value $988,558

    Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

    7706 Waunatta Ct, Winter Park, FL 32792
    • /33

      Est $442,102

      Not Listed For Sale

      2003 Canny Cove, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2023
      2003 Canny Cove, Winter Park, FL 32792

      Last Sold Summary

      • 31 Days On Market

  • /27

    $464,900

    $5K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 1,787 Sq Ft

    1032 Manchester Cir, Winter Park, FL 32792

    Welcome to this beautifully maintained 4-bedroom, 2-bath pool home nestled in one of the desirable neighborhoods of Winter Park within Seminole County. Offering the perfect blend of comfort, space, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining.Step inside to discover a spacious, light-filled floor plan featuring generous living areas,

    Nancy Morales BHHS FLORIDA REALTY

    1032 Manchester Cir, Winter Park, FL 32792
  • /41

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,837 Sq Ft
    • Condo for Rent

    2530 Passamonte Dr Unit 10E, Winter Park, FL 32792

    REMODELLED - new flooring and freshly painted. Welcome home to this beautiful townhome centrally located in Winter Park, 15 miles away from Park Avenue, just outside of Baldwin Park. Enjoy beautiful water views on the back patio. This home is fresh ready to move in. Available for rent April 15 or later. Top schools, Glenridge middle school, Winter Park high school and Brookshire elementary

    Livia Petraru EXP REALTY LLC

    2530 Passamonte Dr Unit 10E, Winter Park, FL 32792
  • /2

    $1,110,000

    Sold Aug 26, 2025

    233 Hampden Place, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 2,813 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $395/SF
    • 7 Days On Market

    Current Estimated Value $1,211,574

    Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

    233 Hampden Place, Winter Park, FL 32789
    • /55

      Est $1,143,009

      Not Listed For Sale

      1772 Mondrian Cir, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,193 Sq Ft
      • Built 2023
      1772 Mondrian Cir, Winter Park, FL 32789

      Last Sold Summary

      • 83 Days On Market

  • /9

    $349,000

    • 2 Beds
    • 1 Bath
    • 749 Sq Ft

    811 Overspin Dr, Winter Park, FL 32789

    Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those

    Rickey Singh RICK SINGH REAL ESTATE

    811 Overspin Dr, Winter Park, FL 32789
  • /20

    $2,499 Per Month

    • 3 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • House for Rent

    1947 Summerfield Rd, Winter Park, FL 32792

    Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act

    1947 Summerfield Rd, Winter Park, FL 32792
  • /2

    $200,000

    Sold Sep 13, 2025

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

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • Built 1984

    Last Sold Summary

    • 11% Below List Price
    • $174/SF
    • 131 Days On Market

    Current Estimated Value $206,735

    Last Listing Agent Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

    3251 Oak Lake Place Unit 135, Winter Park, FL 32792
    • /19

      Est $239,291

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792

      • 2 Beds
      • 1.5 Baths
      • 1,219 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

  • /10

    $5,500,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,775 Sq Ft

    313 Sylvan Dr, Winter Park, FL 32789

    Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    313 Sylvan Dr, Winter Park, FL 32789
  • /11

    $1,745 Per Month

    • 3 Beds
    • 1.5 Baths
    • 970 Sq Ft
    • Townhouse for Rent

    3232 Royal St, Winter Park, FL 32792

    Very clean 1/2 duplex near Full Sail University. 2 initial bedrooms with third bedroom built out into the insulated and air conditioned garage. There is storage space in the garage but not enough to park a car. Located off of Forsythe Rd near University Blvd, this home is ideal for a student at Full Sail University or UCF. Very close to major roadways of Semoran Bv (SR436) and University Bv.

    Joe Thomas CLASSIC 1 REALTY INC

    3232 Royal St, Winter Park, FL 32792
  • /2

    $180,000

    Sold May 18, 2026

    200 Saint Andrews Blvd Unit 705, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft
    • Built 1970

    Last Sold Summary

    • $248/SF
    • 45 Days On Market

    Current Estimated Value $176,619

    Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

    200 Saint Andrews Blvd Unit 705, Winter Park, FL 32792
    • /43

      Est $779,238

      Not Listed For Sale

      7984 Pleasant Pine Cir, Winter Park, FL 32792

      • 5 Beds
      • 4 Baths
      • 3,496 Sq Ft
      • Built 2016
      7984 Pleasant Pine Cir, Winter Park, FL 32792

      Last Sold Summary

      • 0 Days On Market

  • /60

    $2,150,000

    $195K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 3,986 Sq Ft

    2299 Via Tuscany, Winter Park, FL 32789

    Under contract-accepting backup offers. BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for

    Vincent Scarlatos CORCORAN PREMIER REALTY

    2299 Via Tuscany, Winter Park, FL 32789
  • /15

    $2,495 Per Month

    • 4 Beds
    • 2 Baths
    • 1,669 Sq Ft
    • House for Rent

    2730 Prince John Rd, Winter Park, FL 32792

    Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *Bonus Amenity Included* -All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident

    2730 Prince John Rd, Winter Park, FL 32792
  • /2

    $3,200,000

    Sold Nov 04, 2025

    1900 W Fawsett Rd, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,600 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $696/SF
    • 6 Days On Market

    Current Estimated Value $3,167,326

    Last Listing Agent Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

    1900 W Fawsett Rd, Winter Park, FL 32789
    • /40

      Est $828,628

      Not Listed For Sale

      2035 Soaring Oak Way, Winter Park, FL 32792

      • 4 Beds
      • 3 Baths
      • 2,706 Sq Ft
      • Built 2021
      2035 Soaring Oak Way, Winter Park, FL 32792

      Last Sold Summary

      • 130 Days On Market

  • /44

    $899,000

    Open Sun 12PM - 2PM $76K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,003 Sq Ft

    1507 Golfside Dr, Winter Park, FL 32792

    Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    1507 Golfside Dr, Winter Park, FL 32792
  • /48

    $9,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft
    • House for Rent

    1760 Alabama Dr, Winter Park, FL 32789

    Behind a gated courtyard entrance in the Vias of Winter Park, just around the corner from Kraft Azalea Garden on the shores of Lake Maitland, this move-in ready residence offers privacy, thoughtful design and exceptional indoor-outdoor living. Surrounded by mature landscaping and accessed from both front and rear driveways, the property provides a rare sense of seclusion while remaining minutes

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    1760 Alabama Dr, Winter Park, FL 32789
  • /2

    $600,000

    Sold May 15, 2026

    3110 Heartleaf Place, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,704 Sq Ft
    • Built 1998

    Last Sold Summary

    • 5% Below List Price
    • $222/SF
    • 3 Days On Market

    Current Estimated Value $627,726

    Last Listing Agent Hajime Shimabukuro FUSILIER MANAGEMENT GROUP

    3110 Heartleaf Place, Winter Park, FL 32792
    • /2

      Est $659,677

      Not Listed For Sale

      1219 Verdant Glade Place, Winter Park, FL 32792

      • 3 Beds
      • 3.5 Baths
      • 2,002 Sq Ft
      • Built 2019
      1219 Verdant Glade Place, Winter Park, FL 32792

      Last Sold Summary

      • 79 Days On Market

  • /36

    $849,000

    Open Sat 2PM - 4PM
    • 3 Beds
    • 2.5 Baths
    • 1,904 Sq Ft

    437 N Capen Ave, Winter Park, FL 32789

    Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’

    Brandon Geers COMPASS FLORIDA LLC

    437 N Capen Ave, Winter Park, FL 32789
  • /27

    $1,455 Per Month

    • 2 Beds
    • 2 Baths
    • 956 Sq Ft
    • Condo for Rent

    2500 Lee Rd Unit 103, Winter Park, FL 32789

    Welcome to Lakeside Manor on beautiful Lake Killarney! This spacious 2-bedroom, 2-bath condo offers comfortable living in one of the most convenient locations in the Orlando/Winter Park area. The unit features a bright and open living space and generously sized bedrooms.Residents of Lakeside Manor enjoy access to community amenities including private Lake Killarney access, a community

    2500 Lee Rd Unit 103, Winter Park, FL 32789
  • /2

    $630,000

    Sold Aug 11, 2025

    1792 Killarney Dr, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,264 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $278/SF
    • 1 Day On Market

    Current Estimated Value $664,443

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    1792 Killarney Dr, Winter Park, FL 32789
    • /25

      Est $295,500

      Not Listed For Sale

      5408 Peaco Place, Winter Park, FL 32792

      • 3 Beds
      • 1.5 Baths
      • 1,439 Sq Ft
      • Built 1984
      5408 Peaco Place, Winter Park, FL 32792

      Last Sold Summary

      • 24 Days On Market

Showing Results 561 - 600, Page 15 of 18

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