28,233

Winter Park, FL Homes

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  • /38

    $825,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,540 Sq Ft

    1431 Palm Ave, Winter Park, FL 32789

    Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along picturesque brick streets shaded by mature trees, this inviting home offers a warm, light-filled interior and a private backyard oasis. From the moment you enter, you’ll notice the abundance of natural light and the large windows

    Kelsey Payton ALL REAL ESTATE & INVESTMENTS

    1431 Palm Ave, Winter Park, FL 32789
  • /11

    $2,400 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft
    • House for Rent

    258 Balfour Dr, Winter Park, FL 32792

    Property Id: 439431 Property is right off of Aloma, fairly close to Park Avenue area. It is a 3 Bedroom, 2.5 Bath house, with newly installed wood floors and neutral paint throughout. It has a 2 car garage and a sun room as well as a small privacy fenced in yard. All three bedrooms are upstairs with the living and dining area being downstairs. Call Ben for showing

    258 Balfour Dr, Winter Park, FL 32792
  • /2

    $165,000

    Sold Jun 01, 2026

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792

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

    Last Sold Summary

    • 6% Below List Price
    • $208/SF
    • 77 Days On Market

    Current Estimated Value $165,611

    Last Listing Agent Eric Zimmerman RE/MAX ADVANTAGE

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792
    • /2

      Est $88,667

      Not Listed For Sale

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

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

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Benjamin W Berry EXP REALTY LLC

  • /20

    $315,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft

    1540 Florentino Ln, Winter Park, FL 32792

    Under contract-accepting backup offers. Come and see your new home in the sought after Vistas at Howell Branch community. This two story townhouse has 3 bedrooms, 2.5 baths, and open first floor, floor plan. Relax in the evening on your screened in porch. The master bedroom has a walk in closet and large master bath. Your washer and dryer are on the second floor centrally located to all the

    Ashley Fisak COLDWELL BANKER REALTY

    1540 Florentino Ln, Winter Park, FL 32792
  • /17

    $6,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Apartment for Rent

    301 W Comstock Ave, Winter Park, FL 32789

    Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

    Sydney Brownlee THE SYDGAN CORP

    301 W Comstock Ave, Winter Park, FL 32789
  • /2

    $425,000

    Sold Jun 26, 2026

    1923 Linden Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,117 Sq Ft
    • Built 1955

    Last Sold Summary

    • 15% Below List Price
    • $201/SF
    • 57 Days On Market

    Current Estimated Value $441,025

    Last Listing Agent Milton James COLDWELL BANKER REALTY

    1923 Linden Rd, Winter Park, FL 32792
    • /21

      Not Listed For Sale

      7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,267 Sq Ft
      • Built 1974
      7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

  • /27

    $424,400

    $51K PRICE DROP Pending
    • 1 Bed
    • 1 Bath
    • 767 Sq Ft

    644 N Knowles Ave Unit 3, Winter Park, FL 32789

    Virtually Staged. LOCATION! LOCATION! LOCATION! Welcome to Knowles Manor...a charming 11 unit condo perched on quiet brick street in the heart of Olde Winter Park...just steps from the Winter Park 9 golf course, Casa Feliz, and the boutiques, restaurants, and vibrant lifestyle of Park Avenue, this location is hard to beat. This delightful first-floor residence is the perfect place to call home or

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    644 N Knowles Ave Unit 3, Winter Park, FL 32789
  • /14

    $1,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,134 Sq Ft
    • House for Rent

    617 Dunraven Dr, Winter Park, FL 32792

    Property Id: 2862438 Welcome to this charming 4 bed, 3.5 bath single-family home in Winter Park, FL! Built in 1964, this property boasts modern amenities including a dishwasher, washer/dryer, and fenced yard. Pet-friendly with a garage, this home is perfect for families. Don't miss out on this gem!

    617 Dunraven Dr, Winter Park, FL 32792
  • /2

    $1,300,000

    Sold Sep 22, 2025

    1371 Lyndale Blvd, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,714 Sq Ft
    • Built 1949

    Last Sold Summary

    • 4% Below List Price
    • $479/SF
    • 8 Days On Market

    Current Estimated Value $1,309,890

    Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

    1371 Lyndale Blvd, Winter Park, FL 32789
    • /2

      Est $1,513,040

      Not Listed For Sale

      101 S New York Ave Unit 303, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,174 Sq Ft
      • Built 2009
      101 S New York Ave Unit 303, Winter Park, FL 32789

      Last Sold Summary

      • 129 Days On Market

      Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  • /45

    $185,000

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft

    7450 Wynnewood Square Unit 189, Winter Park, FL 32792

    This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the upstairs boasts beautiful

    Kimberly King REAL ESTATE PROFESSIONALS SE

    7450 Wynnewood Square Unit 189, Winter Park, FL 32792
  • /38

    $3,200 Per Month

    • 5 Beds
    • 3 Baths
    • 2,300 Sq Ft
    • House for Rent

    5354 Lanyard Ct, Winter Park, FL 32792

    Welcome to 5354 Lanyard Court, a spacious Winter Park pool home offering approximately 2,300 square feet of flexible living space, 5 bedrooms, 3 full bathrooms and a large fenced backyard.The main residence features 3 bedrooms and 2 full bathrooms with comfortable living areas designed for everyday living and entertaining. One of the property's standout features is the separate suite,

    Johanna Chandler LPT REALTY, LLC

    5354 Lanyard Ct, Winter Park, FL 32792
  • /2

    $405,000

    Sold Jan 09, 2026

    3425 Ferndell Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,516 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $267/SF
    • 164 Days On Market

    Current Estimated Value $402,852

    Last Listing Agent Ivanhoe Alvarez LOKATION

    3425 Ferndell Dr, Winter Park, FL 32792
    • /30

      Est $1,499,549

      Not Listed For Sale

      311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

      • 3 Beds
      • 2 Baths
      • 2,066 Sq Ft
      • Built 1960
      311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

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

  • /12

    $1,699,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,530 Sq Ft

    2308 Mulbry Dr, Winter Park, FL 32789

    Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet of open-concept living space, the home features four bedrooms and three-and-a-half lavish bathrooms. Framed by hand-selected architectural stone, the elegant entryway reveals a luminous interior anchored by wide-plank light oak

    Brandon Geers COMPASS FLORIDA LLC

    2308 Mulbry Dr, Winter Park, FL 32789
  • /20

    $2,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,220 Sq Ft
    • House for Rent

    3557 Arbutus Ln, Winter Park, FL 32792

    Property Id: 1928209 Make this unique 3 bedroom, 2 bath pool home yours in the desirable Winter Park. This home has a lot of character that makes it feel like home. There is vintage fireplace in the living room, wood beams. The kitchen is still newly remodeled with quartz countertops, a generous amount of wood cabinets for storage and tile backsplash. The master bedroom has its own private

    3557 Arbutus Ln, Winter Park, FL 32792
  • /2

    $235,000

    Sold Jan 29, 2026

    613 Orange Tree Ct Unit 507, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Below List Price
    • $187/SF
    • 10 Days On Market

    Current Estimated Value $237,334

    Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

    613 Orange Tree Ct Unit 507, Maitland, FL 32751
    • /2

      Est $189,658

      Not Listed For Sale

      3043 Antique Oaks Cir Unit 171, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,018 Sq Ft
      • Built 1984
      3043 Antique Oaks Cir Unit 171, Winter Park, FL 32792

      Last Sold Summary

      • 331 Days On Market

      Last Listing Agent Mikhael Najm DALTON WADE INC

  • /72

    $3,750,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,377 Sq Ft

    2622 Lake Howell Ln, Winter Park, FL 32792

    Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare

    Brian Hyser THE AGENCY FL

    2622 Lake Howell Ln, Winter Park, FL 32792
  • /15

    $1,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,295 Sq Ft
    • House for Rent

    3629 Hedgewood Dr, Winter Park, FL 32792

    Lovely 3-bedroom 2 Bath, Fenced yard and open back patio. Laminate and terrazzo flooring. This home comes with a washer and dryer and lawn care is included! As you walk into the kitchen to the right you walk into the covered back patio great for gatherings. Theres also a eat in kitchen as you walk from the garage. Hall bathroom has a tub as the master bathroom has a walk-in shower. This one won't

    Jeff Anderson HD REALTY LLC

    3629 Hedgewood Dr, Winter Park, FL 32792
  • /24

    $649,000

    Sold Oct 17, 2025

    2304 Depauw Ave, Orlando, FL 32804

    • 3 Beds
    • 2.5 Baths
    • 1,668 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $389/SF
    • 199 Days On Market

    Current Estimated Value $648,000

    David Weekley Homes Central Living - Downtown

    2304 Depauw Ave, Orlando, FL 32804
    • /2

      Est $177,319

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,067 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Patricia Wojewoda BETTER HOMES & GARDENS RE STAR

  • /41

    $275,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    5143 Lazy Oaks Dr, Winter Park, FL 32792

    Virtually Staged. Quiet Living in the Desirable Lazy Oaks Community of Winter Park.Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA.This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed

    Mindy Machock KELLER WILLIAMS REALTY AT THE PARKS

    5143 Lazy Oaks Dr, Winter Park, FL 32792
  • /15

    $1,350 Per Month

    • 1 Bed
    • 1 Bath
    • 763 Sq Ft
    • House for Rent

    4874 Tangerine Ave, Winter Park, FL 32792

    Discover comfort and convenience in this charming 1-bedroom, 1-bathroom condo. The unit comes equipped with a stove and refrigerator, perfect for your culinary needs. Enjoy the cozy ambiance provided by carpeted floors and the elegant touch of wood cabinets. This property is part of a well-maintained community featuring a refreshing pool, ideal for relaxing and unwinding. Don’t miss out on this

    4874 Tangerine Ave, Winter Park, FL 32792
  • /2

    $500,000

    Sold May 27, 2026

    720 W Webster Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • Built 1950

    Last Sold Summary

    • 9% Below List Price
    • $369/SF
    • 54 Days On Market

    Current Estimated Value $501,470

    Last Listing Agent Vincent Cordaro SERHANT

    720 W Webster Ave, Winter Park, FL 32789
    • /2

      Est $361,523

      Not Listed For Sale

      1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

      • 1 Bed
      • 1 Bath
      • 864 Sq Ft
      • Built 1983
      1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Abby Nelson RE/MAX 200 REALTY

  • /31

    $419,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,836 Sq Ft

    1842 Puritan Ave, Winter Park, FL 32792

    Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful 4 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your

    Karan Jodha MOBED REALTY, P.A

    1842 Puritan Ave, Winter Park, FL 32792
  • /13

    $1,750 Per Month

    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft
    • Condo for Rent

    612 Trinidad Ct Unit 612, Winter Park, FL 32792

    Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area

    Carolina Barriento JEXOR LLC

    612 Trinidad Ct Unit 612, Winter Park, FL 32792
  • /2

    $180,000

    Sold Jan 06, 2026

    2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $177/SF
    • 8 Days On Market

    Current Estimated Value $184,304

    Last Listing Agent Chris Bessette KELLER WILLIAMS CLASSIC

    2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      3153 Greenwood St Unit Winter Spr, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,241 Sq Ft
      • Built 1984
      3153 Greenwood St Unit Winter Spr, Winter Park, FL 32792

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Allison Day RE/MAX TOWN & COUNTRY REALTY

  • /38

    $669,900

    Open Sat 11AM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft

    274 N Ranger Blvd, Winter Park, FL 32792

    Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! From the moment you enter, you will appreciate the home's refined modern aesthetic, clean architectural lines, and thoughtfully curated finishes. Brand new flooring creates a seamless sense of elegance throughout, while sleek new cabinetry, contemporary finishes,

    SHANNON LEE EXPLORE FLORIDA REALTY SERVICES LLC

    274 N Ranger Blvd, Winter Park, FL 32792
  • /11

    $1,375 Per Month

    • 2 Beds
    • 2 Baths
    • 1,045 Sq Ft
    • Condo for Rent

    1000 S Semoran Blvd Unit 806, Winter Park, FL 32792

    LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included! Apply Today!TO SCHEDULE A SHOWING YOU MUST EMAIL US WITH YOUR CONTACT INFORMATION AND THE PROPERTY YOU WISH TO SEE AT AND AN AGENT WILL RESPOND BACK WITH THE AVAILABLE SHOW TIMES.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process

    1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
  • /2

    $1,950,000

    Sold Sep 16, 2025

    141 Oakwood Way, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 3,909 Sq Ft
    • Built 2015

    Last Sold Summary

    • 14% Below List Price
    • $499/SF
    • 170 Days On Market

    Current Estimated Value $2,022,969

    Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

    141 Oakwood Way, Winter Park, FL 32789
    • /2

      Est $392,341

      Not Listed For Sale

      3121 Thistlehill Dr, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,503 Sq Ft
      • Built 1967
      3121 Thistlehill Dr, Winter Park, FL 32792

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Mark Ramey EXP REALTY LLC

  • /24

    $305,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    2370 Barbados Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. Virtually Staged. Just Listed for Sale in Winter Park - Windward Square. Lovely 3/2 townhouse. Low HOA. Community pool and playground. Great location.

    Jose Perez COLDWELL BANKER REALTY

    2370 Barbados Dr, Winter Park, FL 32792
  • /18

    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 1,174 Sq Ft
    • Townhouse for Rent

    3217 Royal St, Winter Park, FL 32792

    Beautifully renovated 3-bedroom, 2-bathroom rental home located in Winter Park. This property features a spacious 2-car garage, washer and dryer included, and a private backyard, all situated on a quiet cul-de-sac. The home has been newly renovated with updated finishes throughout, providing a clean and comfortable living space. The location offers excellent access to Central Florida, with Full

    Stephen Murphy DALTON WADE INC

    3217 Royal St, Winter Park, FL 32792
  • /2

    $160,000

    Sold Jun 05, 2026

    2500 Lee Rd Unit 122, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft
    • Built 1969

    Last Sold Summary

    • 11% Below List Price
    • $248/SF
    • 60 Days On Market

    Current Estimated Value $161,423

    Last Listing Agent Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

    2500 Lee Rd Unit 122, Winter Park, FL 32789
    • /2

      Est $1,282,961

      Not Listed For Sale

      309 Park Ct N, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,096 Sq Ft
      • Built 1968
      309 Park Ct N, Winter Park, FL 32789

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

Showing Results 281 - 320, Page 8 of 18

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