28,233

Winter Park, FL Homes

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  • /55

    $475,000

    $75K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,428 Sq Ft

    630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

    Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is

    Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

    630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
  • /46

    $4,295 Per Month

    • 4 Beds
    • 3 Baths
    • 2,134 Sq Ft
    • 4/3 WINTER PARK POOL HOME WITH WINTER PARK SCHOOLS! (Orange County Winter Park Schools)

    1625 Tioga Trail, Winter Park, FL 32789

    A RARE FIND IN WINTER PARK!! 4 BEDROOMS, 3 BATHROOMS, POOL, AND FENCED BACKYARD.Welcome home to this beautifully updated 4-bedroom, 3-bath pool home nestled on a quiet cul-de-sac in Winter Park Hills. Surrounded by million-dollar homes and zoned for excellent Winter Park schools (Dommerich Elementary, Maitland Middle and Winter Park High), this exceptional rental offers the perfect

    1625 Tioga Trail, Winter Park, FL 32789
  • /2

    $625,000

    Sold Jul 30, 2026

    2652 Abbey Rd, Winter Park, FL 32792

    • 5 Beds
    • 2 Baths
    • 1,938 Sq Ft
    • Built 1967

    Last Sold Summary

    • $322/SF
    • 7 Days On Market

    Current Estimated Value $564,288

    Last Listing Agent Mario Zendeli COMPASS FLORIDA LLC

    2652 Abbey Rd, Winter Park, FL 32792
    • /2

      Est $628,049

      Not Listed For Sale

      1401 Lone Feather Trail, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,770 Sq Ft
      • Built 2022
      1401 Lone Feather Trail, Winter Park, FL 32792

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  • /29

    $494,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,565 Sq Ft

    2715 Prince John Rd, Winter Park, FL 32792

    GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for

    Donna Peebles VIA PROPERTIES LLC

    2715 Prince John Rd, Winter Park, FL 32792
  • /31

    $4,820 Per Month

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft
    • House for Rent

    2341 Devon Ct, Winter Park, FL 32789

    Welcome to your private Winter Park retreat! This beautifully updated home offers comfort, charm, and plenty of space to settle in and enjoy. Inside, you’ll find a bright and inviting layout with stylish finishes, cozy living spaces, a well-equipped kitchen, comfortable bedrooms, and thoughtful touches throughout.The backyard is a true highlight — spacious, private, and perfect for

    Gabriel Cancel Rivera EXIT REALTY PREMIER LEGACY

    2341 Devon Ct, Winter Park, FL 32789
  • /2

    $215,000

    Sold Jul 08, 2026

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,058 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $203/SF
    • 76 Days On Market

    Current Estimated Value $206,294

    Last Listing Agent Angelica Diaz Bajo WRA BUSINESS & REAL ESTATE

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792
    • /2

      Est $307,281

      Not Listed For Sale

      2762 Hilda Cove, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,493 Sq Ft
      • Built 1981
      2762 Hilda Cove, Winter Park, FL 32792

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Thomas Weclew THE REALTY MEDICS

  • /28

    $245,000

    • 2 Beds
    • 2 Baths
    • 908 Sq Ft

    1250 S Denning Dr Unit 127, Winter Park, FL 32789

    Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    1250 S Denning Dr Unit 127, Winter Park, FL 32789
  • /26

    $2,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,158 Sq Ft
    • House for Rent

    301 S Capen Ave, Winter Park, FL 32789

    Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue.Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage.Down the hall, you'll find three

    301 S Capen Ave, Winter Park, FL 32789
  • /2

    $850,000

    Sold Mar 25, 2026

    465 N Phelps Ave, Winter Park, FL 32789

    • Land
    • 11,761 Sq Ft
    • $3,148,148 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $841,542

    Last Listing Agent Hircanys Vicioso KELLER WILLIAMS ADVANTAGE III

    465 N Phelps Ave, Winter Park, FL 32789
    • /2

      Est $752,467

      Not Listed For Sale

      1166 Wildmeadow Run, Winter Park, FL 32792

      • 4 Beds
      • 3.5 Baths
      • 2,589 Sq Ft
      • Built 2021
      1166 Wildmeadow Run, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Liz Jones ORANGE SLICE PROPERTIES

  • /72

    $3,395,000

    • 5 Beds
    • 5.5 Baths
    • 4,015 Sq Ft

    160 W Rockwood Way, Winter Park, FL 32789

    Perfectly positioned in the heart of Old Winter Park, the quaint Forrest Hills neighborhood is lined with charming cobblestone streets that wind around Lake Sue. This custom home, designed and built by the celebrated Z-Properties, pairs timeless New England character with modern sensibilities. Every detail is intentional in this iconic design—nothing has been sacrificed.Situated on a

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    160 W Rockwood Way, Winter Park, FL 32789
  • /17

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,149 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit E115, Winter Park, FL 32789

    Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit E115, Winter Park, FL 32789
  • /2

    $410,000

    Sold Jun 30, 2026

    2779 Sanbina St, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,405 Sq Ft
    • Built 1960

    Last Sold Summary

    • 11% Below List Price
    • $292/SF
    • 82 Days On Market

    Current Estimated Value $425,102

    Last Listing Agent Caroline Fiore MAINFRAME REAL ESTATE

    2779 Sanbina St, Winter Park, FL 32789
    • /2

      Est $759,861

      Not Listed For Sale

      2255 Marsh Sedge Ln, Winter Park, FL 32792

      • 4 Beds
      • 3 Baths
      • 2,192 Sq Ft
      • Built 2020
      2255 Marsh Sedge Ln, Winter Park, FL 32792

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY

  • /58

    $1,795,000

    $155K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,807 Sq Ft

    106 S Interlachen Ave Unit 518, Winter Park, FL 32789

    Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural

    Mary Colton FANNIE HILLMAN & ASSOCIATES

    106 S Interlachen Ave Unit 518, Winter Park, FL 32789
  • /23

    $1,650 Per Month

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

    2404 Gallery View Dr, Winter Park, FL 32792

    Fantastic condo! Ready move-in Aug 1st!! Super Location: 2nd floor 2/2 condo in sought-after Winter Park, walking distance from restaurants, grocery stores, etc... Convenient to Rollins College. You will love living in this small luxury complex that has been kept in superb condition. The condo is in a quiet setting with wood floors, vaulted ceilings, wood blinds, and a split floor plan. Enjoy the

    2404 Gallery View Dr, Winter Park, FL 32792
  • /2

    $445,000

    Sold Jun 04, 2026

    1832 E Cheryl Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Above List Price
    • $246/SF
    • 6 Days On Market

    Current Estimated Value $442,373

    Last Listing Agent Shanon Luiz SELECTIVE REALTY GROUP LLC

    1832 E Cheryl Dr, Winter Park, FL 32792
    • /2

      Est $1,058,374

      Not Listed For Sale

      1024 Wading Waters Cir, Winter Park, FL 32792

      • 4 Beds
      • 3 Baths
      • 3,057 Sq Ft
      • Built 2021
      1024 Wading Waters Cir, Winter Park, FL 32792

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  • /35

    $175,000

    $10K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,058 Sq Ft

    4798 Tangerine Ave, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to this charming and well-maintained condominium located in the desirable Winter Park area, offering the perfect blend of comfort, convenience, and low-maintenance living. This inviting residence features a spacious and functional layout filled with natural light, creating a warm and welcoming atmosphere ideal for everyday living or

    Vincenza Di Cesare De Vieira LPT REALTY, LLC

    4798 Tangerine Ave, Winter Park, FL 32792
  • /11

    $1,150 Per Month

    • 1 Bed
    • 1 Bath
    • 735 Sq Ft
    • Condo for Rent

    1000 S Semoran Blvd Unit 715, Winter Park, FL 32792

    Enjoy comfortable living in the highly sought-after Winter Park area! Close to shopping, dining, and major roadways, this well-located rental provides exceptional value in one of Central Florida's most desirable communities. This first-floor condo is ideally located just steps from the community pool and on-site laundry facilities, offering convenience and easy access to everyday amenities. Don't

    Lety Morales LPT REALTY, LLC

    1000 S Semoran Blvd Unit 715, Winter Park, FL 32792
  • /2

    $268,000

    Sold Feb 24, 2026

    609 Gallery Dr Unit 204, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 893 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Below List Price
    • $300/SF
    • 99 Days On Market

    Current Estimated Value $254,848

    Last Listing Agent Olga Ray A2Z REALTY GROUP

    609 Gallery Dr Unit 204, Winter Park, FL 32792
    • /2

      Est $435,478

      Not Listed For Sale

      1935 Canny Cove, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2023
      1935 Canny Cove, Winter Park, FL 32792

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Gordy Singh COMPASS FLORIDA, LLC

  • /30

    $349,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,397 Sq Ft

    3328 Hamlet Loop, Winter Park, FL 32792

    Virtually Staged. Comfort, style, and convenience come together in this beautifully maintained 3-bedroom, 2-bath home in the desirable Villas of Casselberry community. Soaring vaulted ceilings, an open floor plan, and abundant natural light create a spacious, inviting feel. The kitchen features stone countertops, ample cabinet space, and a cozy breakfast area, while the split-bedroom layout

    Daniel Robinson HOUWZER INC

    3328 Hamlet Loop, Winter Park, FL 32792
  • /2

    $1,800 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    759 Antonette Ave, Winter Park, FL 32789

    Wonderful 1 bedroom, 1 bathroom half of a duplex for rent in the College Quarter neighborhood of Winter Park. The location is walking distance to Park Ave and Rollins College. Inside the property there is a spacious living and bedroom, kitchen with a stackable washer/ dryer and a bathroom. There are charming wood floors and a spacious closet. Outside there is a detached shed, perfect for storing

    759 Antonette Ave, Winter Park, FL 32789
  • /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 $703,802

    Last Listing Agent Melissa Johnson EXP REALTY LLC

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

      Est $808,159

      Not Listed For Sale

      1421 Wooddale Ave, Winter Park, FL 32789

      • 3 Beds
      • 2 Baths
      • 1,628 Sq Ft
      • Built 1950
      1421 Wooddale Ave, Winter Park, FL 32789

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Rafael Casallas, Pa EMPIRE NETWORK REALTY

  • /52

    $674,900

    Open Sat 10AM - 1PM $75K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,411 Sq Ft

    860 N Denning Dr, Winter Park, FL 32789

    **NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME**This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation —

    LaDarrius Sanders OUTLET REALTY

    860 N Denning Dr, Winter Park, FL 32789
  • /11

    $1,600 Per Month

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

    7338 Swallow Run Unit 7338, Winter Park, FL 32792

    Whole apartment to your self. 2BR/2BA - This apartment has Good vibes - Cozy - Minutes away from everything !!! Really!!! Fully renovated Winter Park condo. What truly sets it apart, however, is the time you'll save. Centrally located, minutes from shopping, groceries, restaurants, universities, hospitals, entertainment, and everyday essentials. Believe-me you'll spend less time driving and more

    Jonathan Minerick HOMECOIN.COM

    7338 Swallow Run Unit 7338, 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 $366,348

    Last Listing Agent Michael Rogers INNOVATIVE REALTY, LLC

    7213 Silver Place, Winter Park, FL 32792
    • /2

      Est $308,683

      Not Listed For Sale

      5804 Shale Ct, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,055 Sq Ft
      • Built 1985
      5804 Shale Ct, Winter Park, FL 32792

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Mario Zendeli COMPASS FLORIDA LLC

  • /19

    $379,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,285 Sq Ft

    1605 Puritan Ave, Winter Park, FL 32792

    SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand-new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and

    Angelica Tomlinson LLC CENTURY 21 CARIOTI

    1605 Puritan Ave, Winter Park, FL 32792
  • /17

    $2,050 Per Month

    • 3 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • House for Rent

    1603 Winter Green Blvd, Winter Park, FL 32792

    This Spacious 3bd/2ba home with a fenced yard is located in the community of Winter Green in Winter Park. The Home has a Livingroom/dining room combo with tile and carpet flooring throughout. Kitchen appliances include: Refrigerator, range and dishwasher. Large master bedroom that has a walk-in closet and spacious master bath. Community amenities include: Community pool and tennis courts.

    1603 Winter Green Blvd, Winter Park, FL 32792
  • /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 $974,931

    Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

    7706 Waunatta Ct, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      677 Grenadine Ct Unit S, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,037 Sq Ft
      • Built 1981
      677 Grenadine Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • 103 Days On Market

      Last Listing Agent Barbara Zapotocky RE/MAX AEROSPACE REALTY

  • /75

    $1,949,500

    $241K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,422 Sq Ft

    1420 Aloma Ave, Winter Park, FL 32789

    Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water

    Alejandra Silva METROPOLITAN R.E SOLUTIONS INC

    1420 Aloma Ave, Winter Park, FL 32789
  • /10

    $1,525 Per Month

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft
    • House for Rent

    2530 Kamnic Ct, Winter Park, FL 32792

    This 2 bedroom, 2 bathroom villa is located in Winter Park near local shops, restaurants, and schools. Features include a spacious split floor plan with tile flooring throughout, a lovely kitchen with breakfast bar, living room, a wonderful primary suite with a large walk-in closet, laundry room, additional storage room, a fenced yard, and private parking.Schedule a showing or submit an

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    2530 Kamnic Ct, Winter Park, FL 32792
  • /2

    $353,000

    Sold Jul 22, 2026

    2973 Sanbina St, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft
    • Built 1965

    Last Sold Summary

    • 7% Below List Price
    • $313/SF
    • 53 Days On Market

    Current Estimated Value $378,476

    Last Listing Agent Nicholas Musashe SUN PROPERTIES, INC.

    2973 Sanbina St, Winter Park, FL 32789
    • /2

      Est $264,721

      Not Listed For Sale

      7164 Swallow Run Unit GE, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,470 Sq Ft
      • Built 2012
      7164 Swallow Run Unit GE, Winter Park, FL 32792

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Christian Cruz Garayua CENTURY 21 NEXT LEVEL REALTY

Showing Results 481 - 520, Page 13 of 18

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