28,231

Winter Park, FL Homes

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  • /6

    $99,000

    • Studio
    • 1 Bath
    • 537 Sq Ft

    3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792

    Attention investors! Take a look at this great opportunity to purchase a Cozy Condo located in Winter Park, FL. This studio condo features beautiful tile floors and lots of closet space. First-floor unit with open patio. Minutes away from Downtown Winter Park, expressway, downtown Orlando, Full Sail, and the University of Central Florida. This community offers a pool, tennis court, and clubhouse.

    Lynda Cheros GOLDENCREST REALTY LLC

    3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
  • /20

    $1,695 Per Month

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

    659 Montego Bay Ct, Winter Park, FL 32792

    WINTER PARK VILLAS — 2-BEDROOM CONDO | $800 MOVE-IN CREDIT + WATER INCLUDED! $1,695/month • 2 Bedrooms • 2 Full Bathrooms • 1,037 Sq. Ft. LIMITED-TIME MOVE-IN SPECIAL Receive a $800 MOVE-IN CREDIT with an approved 12-month lease! WATER INCLUDED IN RENT! No separate monthly water bill — water is included in your rent. Welcome to this charming 2-bedroom,

    659 Montego Bay Ct, Winter Park, FL 32792
  • /2

    $2,700,000

    Sold Oct 02, 2025

    1445 Holts Grove Cir, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 4,489 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Above List Price
    • $601/SF
    • 2 Days On Market

    Current Estimated Value $2,761,734

    Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

    1445 Holts Grove Cir, Winter Park, FL 32789
    • /2

      Est $1,814,805

      Not Listed For Sale

      1411 Border Dr, Winter Park, FL 32789

      • 4 Beds
      • 6 Baths
      • 4,638 Sq Ft
      • Built 2019
      1411 Border Dr, Winter Park, FL 32789

      Last Sold Summary

      • 195 Days On Market

      Last Listing Agent Ana Scarlato CORCORAN PREMIER REALTY

  • /82

    $920,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 3,063 Sq Ft

    1492 Via Sangro Place, Winter Park, FL 32792

    Under contract-accepting backup offers. Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office,

    Maha Matta PA RE/MAX TOWN & COUNTRY REALTY

    1492 Via Sangro Place, Winter Park, FL 32792
  • /20

    $2,150 Per Month

    • 2 Beds
    • 1 Bath
    • 710 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 207, Winter Park, FL 32789

    Welcome to your future home in the heart of Winter Park, located in the desirable Maitland district! This charming property offers a comfortable and convenient lifestyle, with easy access to an array of amenities and attractions. Experience the ease of living with central heating and cooling, complemented by air conditioning and ceiling fans for your comfort throughout the year. This

    151 N Orlando Ave Unit 207, Winter Park, FL 32789
  • /2

    $375,000

    Sold Dec 30, 2025

    3083 Crane Strand Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1972

    Last Sold Summary

    • $312/SF
    • 12 Days On Market

    Current Estimated Value $385,394

    Last Listing Agent Sheri Malin REDFIN CORPORATION

    3083 Crane Strand Dr, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      700 Melrose Ave Unit G, Winter Park, FL 32789

      • 1 Bed
      • 1 Bath
      • 687 Sq Ft
      • Built 1964
      700 Melrose Ave Unit G, Winter Park, FL 32789

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  • /4

    $2,275,000

    New Construction $225K PRICE INCREASE
    • 5 Beds
    • 4.5 Baths
    • 3,813 Sq Ft

    930 Enclave Place, Winter Park, FL 32792

    Pre-Construction. To be built. Lot 19 at 930 Enclave Place presents a rare opportunity to own a newly constructed custom home in one of Winter Park’s most desirable locations—where thoughtful architecture, exceptional craftsmanship, natural beauty and walkable convenience come together.This exceptional custom residence within The Enclave, a premier boutique community in the heart of

    Matthew Burks CORCORAN PREMIER REALTY

    930 Enclave Place, Winter Park, FL 32792
  • /8

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    1250 S Denning Dr, Winter Park, FL 32789

    Property Id: 346094 First floor, spacious living area, quiet neighborhood, shaded and screened patio faces a courtyard/garden w/ seating. Incredible location short distance to Park Avenue, Rollins College, Trader Joes/Whole Foods/Publix, I4 exit, & shopping plazas. Ten minute drive to Downtown. -One reserved parking spot in front of unit door. Several visitor parking spots along side

    1250 S Denning Dr, Winter Park, FL 32789
  • /2

    $660,000

    Sold Nov 17, 2025

    2421 Summerfield Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,256 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Above List Price
    • $293/SF
    • 6 Days On Market

    Current Estimated Value $676,054

    Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

    2421 Summerfield Rd, Winter Park, FL 32792
    • /31

      Est $186,039

      Not Listed For Sale

      3307 Amber Wood Way Unit 106, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,031 Sq Ft
      • Built 1983
      3307 Amber Wood Way Unit 106, Winter Park, FL 32792

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Maureen Golmont WATSON REALTY CORP

  • /21

    $135,000

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

    3020 Antique Oaks Cir Unit 129, Winter Park, FL 32792

    VALUE OPPORTUNITY IN WINTER PARK! Welcome to 3020 Antique Oaks Circle #129, a spacious 2-bedroom, 2-bath FIRST-FLOOR CONDO offering approximately 1,018 square feet in the conveniently located Parkview Village community in Winter Park, FL 32792. If you have been searching for an affordable Winter Park condo, investment property, renovation opportunity, first-floor condo or 2-bedroom condo in

    Cassie Lamoureux KELLER WILLIAMS CLASSIC

    3020 Antique Oaks Cir Unit 129, Winter Park, FL 32792
  • /11

    $2,550

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • House for Rent

    1840 Bachman Way, Winter Park, FL 32792

    Amazing 3 bedroom, 2.5 bathroom house in Winter Park. Freshly painted home with vaulted ceiling throughout! Tile floor on 1st floor and carpet on 2nd floor. Spacious living room area. Great neighborhood with A+ Seminole County schools. Great location and close to schools, shopping and restaurants. Easy access to 436 and major highways. Amenities included: central air, central heat, dishwasher,

    1840 Bachman Way, Winter Park, FL 32792
  • /60

    $384,000

    Sold Aug 14, 2026

    1662 Tremont Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,534 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $250/SF
    • 42 Days On Market

    Current Estimated Value $380,407

    Last Listing Agent Michael Heacock Results Team Prop.& Investment

    1662 Tremont Ln, Winter Park, FL 32792
    • /60

      Est $1,608,575

      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

      Last Listing Agent Lance Kotowski Properties By Lanko, Inc

  • /25

    $295,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,363 Sq Ft

    1484 Viburnum Ln, Winter Park, FL 32792

    Now Available in Eastbrook of Winter Park! Come see this charming Home consisting of 3 bedrooms, 2 bath, 1,363(sqft), -clean residence with a spacious layout and great back yard! This is the perfect home for those looking for space and best of it’s move in ready. Property is being sold “as-is” with right to inspect. New Interior & Exterior paint!! It is the buyers and buyer’s agent responsibility

    Daniel Sefair SEFAIR INVESTMENTS INC

    1484 Viburnum Ln, Winter Park, FL 32792
  • /42

    $1,550 - $1,950

    Total Monthly Price

    • 1 - 3 Beds
    • 2 Baths
    • 800 Sq Ft
    • Condo for Rent

    200 Saint Andrews Blvd, Winter Park, FL 32792

    This is a very well maintained property and grounds. Great and caring HOA. The unit has recently been fully renovated and everything is new. 3 pools, club house, quiet. Great location close to historic Park Ave., Full Sail University, UCF, Hospital, and shoping. Full laundry in building.

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

    $610,000

    Sold Jun 12, 2026

    1174 Wildmeadow Run, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 2021

    Last Sold Summary

    • 9% Below List Price
    • $345/SF
    • 54 Days On Market

    Current Estimated Value $612,480

    Last Listing Agent Kara Lushear COLDWELL BANKER REALTY

    1174 Wildmeadow Run, Winter Park, FL 32792
    • /9

      Est $287,320

      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

      Last Listing Agent GREGORY NOONE CHARLES RUTENBERG REALTY ORLANDO

  • /41

    $2,750,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 3,676 Sq Ft

    948 Poinciana Ln, Winter Park, FL 32789

    Under contract-accepting backup offers. Virtually Staged. Beautifully updated and thoughtfully designed, this four-bedroom, three-and-one-half-bath residence blends sophisticated interiors, inviting living spaces and an impressive outdoor setting. Gorgeous curb appeal and meticulously maintained landscaping create a welcoming first impression, while extensive recent improvements bring a fresh,

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    948 Poinciana Ln, Winter Park, FL 32789
  • /12

    $1,000

    Total Monthly Price

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

    5312 Poinsetta Ave Unit 2, Winter Park, FL 32792

    Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the three rooms has its own electronic keypad lock for your privacy and security. The large common areas provide the perfect space for dining and living. A spacious laundry and kitchen provide you with plenty of space

    5312 Poinsetta Ave Unit 2, Winter Park, FL 32792
  • /2

    $3,485,000

    Sold Oct 17, 2025

    2171 Forrest Rd, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 4,565 Sq Ft
    • Built 2016

    Last Sold Summary

    • 9% Below List Price
    • $763/SF
    • 134 Days On Market

    Current Estimated Value $3,521,934

    Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

    2171 Forrest Rd, Winter Park, FL 32789
    • /24

      Est $185,410

      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

      Last Listing Agent Hojin Chang RE/MAX PRIME PROPERTIES

  • /28

    $625,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,934 Sq Ft

    786 Mcintyre Ave, Winter Park, FL 32789

    Virtually Staged. Welcome to 786 McIntyre Avenue, Winter Park, FL 32789—a serene retreat perched on a picturesque tree-lined brick street in one of Winter Park's most desirable neighborhoods. Just a short stroll from Rollins College and the renowned shops, restaurants, and charm of Park Avenue, this exceptional single-family townhome offers the perfect blend of comfort, style, and location—SINGLE

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    786 Mcintyre Ave, Winter Park, FL 32789
  • /21

    $2,100

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft
    • Condo for Rent

    2383 Sun Valley Cir Unit Winter Park, Winter Park, FL 32792

    Welcome to this charming and beautifully updated home in the serene Cedarwood Village community! Tucked away in a peaceful location, this unit offers a quiet retreat from traffic noise and features a private backyard with no rear neighbors perfect for enjoying the spacious, enclosed lanai. The modern kitchen features sleek granite countertops and matching cabinets, with the bathrooms and dining

    2383 Sun Valley Cir Unit Winter Park, Winter Park, FL 32792
  • /29

    $1,810,000

    Sold Sep 10, 2026

    721 Pansy Ave, Winter Park, FL 32789

    • 4 Beds
    • 4 Baths
    • 2,653 Sq Ft
    • Built 2018

    Last Sold Summary

    • 6% Below List Price
    • $682/SF
    • 129 Days On Market

    Current Estimated Value $1,826,478

    Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    721 Pansy Ave, Winter Park, FL 32789
    • /45

      Est $1,902,168

      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

      Last Listing Agent Chocky Burks CORCORAN PREMIER REALTY

  • /18

    $268,950

    $16K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    3220 Netherwood Dr, Winter Park, FL 32792

    BACK ON MARKET!! Buyer financing fell through! **Qualified buyers may be eligible for up to $40,000 in down payment assistance** Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future

    Nimrah Ashraf THE FIRM RE

    3220 Netherwood Dr, Winter Park, FL 32792
  • /19

    $2,695

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • House for Rent

    1509 Springtime Loop, Winter Park, FL 32792

    This beautiful 3 bedroom, 2 bath home is located in the desirable Autumn Glen neighborhood in Winter Park. Newly Renovated bathrooms, ceramic tile floors for the whole house and freshly painted interior. The entire house has new rooms doors, closets doors and new blinds. Vaulted ceilings throughout the home with skylights. Nice recently renovated kitchen with Stainless steel appliances. Beautiful

    1509 Springtime Loop, Winter Park, FL 32792
  • /71

    $1,000,000

    Sold Apr 01, 2026

    2607 Lafayette Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,770 Sq Ft
    • Built 2018

    Last Sold Summary

    • 15% Below List Price
    • $361/SF
    • 244 Days On Market

    Current Estimated Value $1,053,677

    Last Listing Agent Malgorzata Walas Fortune Christie's International Real Estate

    2607 Lafayette Ave, Winter Park, FL 32789
    • /14

      Est $546,843

      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

      Last Listing Agent nicoletta buonaccordo ALTIS REALTY

  • /31

    $725,000

    • 3 Beds
    • 2 Baths
    • 1,563 Sq Ft

    1850 Bryan Ave, Winter Park, FL 32789

    Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors flow through the inviting living and dining spaces, while a flexible bonus room is well suited for a home office, den or creative space. The kitchen features wood cabinetry and ample counter space. The spacious primary suite

    Jennifer King CORCORAN PREMIER REALTY

    1850 Bryan Ave, Winter Park, FL 32789
  • /14

    $1,750

    Total Monthly Price

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

    276 Cambridge Blvd, Winter Park, FL 32789

    This is a 1 Bedroom and 1 Bathroom DUPLEX, There are two of these Unique Houses on the Property, both are 1 bedroom homes. The Place has been updated, Ceiling Fan in the Bedroom. You can walk between them, The website does not offer Duplex as a listing choiceThis is down the street from Park Ave, Austins Coffee House is in walking distance, and is so close to I-4 that you can be Downtown in

    276 Cambridge Blvd, Winter Park, FL 32789
  • /2

    $390,000

    Sold May 28, 2026

    1036 Manchester Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Below List Price
    • $248/SF
    • 22 Days On Market

    Current Estimated Value $391,619

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1036 Manchester Cir, Winter Park, FL 32792
    • /2

      Est $1,085,797

      Not Listed For Sale

      795 W Canton Ave, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,374 Sq Ft
      • Built 2017
      795 W Canton Ave, Winter Park, FL 32789

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

  • /47

    $614,500

    $21K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    2708 Lion Heart Rd, Winter Park, FL 32792

    Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality.Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The

    Navid Rokh EQUITYPRO LLC

    2708 Lion Heart Rd, Winter Park, FL 32792
  • /13

    $2,250

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    2038 Ponderosa Ave, Winter Park, FL 32792

    Lovely updated home in Winter Park, Seminole County. New corian counters and appliances in kitchen. House is bright, open and totally renovated. Fenced backyard, 2 car garage and ready to move in now. Must see to appreciate!

    2038 Ponderosa Ave, Winter Park, FL 32792
  • /2

    $335,000

    Sold Sep 23, 2025

    5144 N Orange Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1976

    Last Sold Summary

    • 16% Below List Price
    • $263/SF
    • 128 Days On Market

    Current Estimated Value $343,669

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5144 N Orange Ave, Winter Park, FL 32792
    • /40

      Est $251,731

      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

      Last Listing Agent William Grim, III RE/MAX ASSURED

Showing Results 201 - 240, Page 6 of 18

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