Winter Park, FL Homes

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  $730,000

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  744 Cornwall Rd, Winter Park, FL 32792

  Charming 4-Bedroom Home in Desirable Winter Park PinesWelcome to your new home in the heart of Winter Park Pines! This beautifully maintained 4-bedroom, 2-bath residence offers a perfect blend of classic charm and modern comfort, situated in one of Central Florida’s most sought-after neighborhoods.Step inside to find warm hardwood floors that flow throughout the spacious living areas,

  Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

  744 Cornwall Rd, Winter Park, FL 32792
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  /11

  $1,098 - $1,451 per month

  Solis at Winter Park

  1 - 2 Beds

  7502 Sun Key Blvd, Winter Park, FL 32792

  Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

  7502 Sun Key Blvd, Winter Park, FL 32792
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  $3,100,000 Sold Jun 27, 2025

  731 Williams Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,260 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $728/SF
  • 45 Days On Market

  Current Estimated Value $2,996,206

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  731 Williams Dr, Winter Park, FL 32789
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 687 Sq Ft

  700 Melrose Ave Unit G, Winter Park, FL 32789

  700 Melrose Ave Unit G, Winter Park, FL 32789
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  /29

  $1,225,000

  • 3 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  501 W Canton Ave, Winter Park, FL 32789

  Introducing a rare opportunity to own a brand-new, luxury modern townhome just steps from Park Avenue in the heart of Winter Park. This stunning two-story, all-block construction residence offers the perfect blend of design, quality, and location—within walking distance to Hannibal Square, Rollins College, upscale dining, boutique shopping, and more. Inside, soaring 13-foot ceilings, custom wood

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  501 W Canton Ave, Winter Park, FL 32789
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  /21

  $1,450 per month

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

  651 Trinidad Ct Unit S, Winter Park, FL 32792

  Within walking distance to Full Sail University. This is a large one bedroom end unity condo in great condition. This unit is freshly painted, has ceramic tiled through out and features a large living room and separate dining area. This unit comes with its one Washer and dryer, and the water is included in the rent. This is an end unit so this is lots of natural light and privacy.

  Troy Hensley BHHS FLORIDA REALTY

  651 Trinidad Ct Unit S, Winter Park, FL 32792
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  $288,000 Sold Apr 08, 2025

  1811 Winter Green Blvd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • Built 1994

  Last Sold Summary

  • 9% Below List Price
  • $243/SF
  • 204 Days On Market

  Current Estimated Value $300,021

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

  1811 Winter Green Blvd, Winter Park, FL 32792
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  /31

  Est $187,027 Not Listed For Sale

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

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

  3307 Amber Wood Way Unit 106, Winter Park, FL 32792
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  /44

  $985,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,824 Sq Ft

  512 Clarendon Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins College and zoned for AudubonK-8! This spacious 2,824 SF home features two primary suites—one on each level—ideal for guests or multi-gen living. Gorgeous hardwood liketile floors throughout, high ceilings, crown molding, and two fireplaces add

  Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
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  /29

  $1,388 - $1,774 per month

  Atlas at Winter Park

  1 - 3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  $4,772,500 Sold Sep 18, 2025

  765 Via Lugano, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,319 Sq Ft
  • Built 2019

  Last Sold Summary

  • $1,105/SF
  • 1 Day On Market

  Current Estimated Value $4,745,878

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

  765 Via Lugano, Winter Park, FL 32789
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  /15

  Not Listed For Sale

  • 2 Beds
  • 3,098 Sq Ft

  1858 Cornell Ave, Winter Park, FL 32789

  1858 Cornell Ave, Winter Park, FL 32789
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  /49

  $449,000

  • 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 bedrooms and 2 full bath is situated on a 8,250 square feet lot was newly fenced in 2024 which gives a sense of privacy and spaciousness as you enter into the lanai. There is two detached sheds for your storage convenience. This beautiful done was

  Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

  1842 Puritan Ave, Winter Park, FL 32792
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  /52

  $11,500 per month

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft
  • Condo for Rent

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

  Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
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  $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 $2,661,937

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

  1445 Holts Grove Cir, Winter Park, FL 32789
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  Est $1,628,824 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,105 Sq Ft

  1318 Chapman Cir, Winter Park, FL 32789

  1318 Chapman Cir, Winter Park, FL 32789
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  /26

  $725,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,803 Sq Ft

  636 Dunblane Dr, Winter Park, FL 32792

  C H A R M I N G INSIDE & OUT! Delightful curb appeal & quaint front porch welcome you HOME! Move right into this ONE STORY immaculate & charming home on a beautiful tree-lined street in Winter Park. You will be enthralled with the hardwood floors, crown molding, amazing floor plan & tons of natural light! Spacious living room with bay window leads to dining room with original built-ins & french

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  636 Dunblane Dr, Winter Park, FL 32792
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  /35

  $1,555 - $2,175 per month

  The Lofts of Winter Park Village

  1 Bed

  520 N Orlando Ave, Winter Park, FL 32789

  Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

  520 N Orlando Ave, Winter Park, FL 32789
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  /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

  Last Listing Agent Sheri Malin REDFIN CORPORATION

  3083 Crane Strand Dr, Winter Park, FL 32792
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  Est $291,285 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft

  5774 Shale Ct, Winter Park, FL 32792

  5774 Shale Ct, Winter Park, FL 32792
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  /29

  $739,900

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft

  1213 Lindenwood Ln, Winter Park, FL 32792

  Discover the perfect blend of mid-century modern architecture and contemporary living in this beautifully updated 4-bedroom, 2-bath residence offering over 2,500 square feet of thoughtfully designed space. Situated on a spacious lot in a private cul-de-sac, this home features an inviting open floor plan, soaring vaulted ceilings, and abundant natural light that highlights its clean lines and

  Amy Turner KELLER WILLIAMS WINTER PARK

  1213 Lindenwood Ln, Winter Park, FL 32792
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  /27

  $1,370 per month

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

  2905 Antique Oaks Cir Unit 4, Winter Park, FL 32792

  Beautifully updated 1 bedroom 1 bath in Winter Park! Very close to Full Sail University, UCF, tons of dining options and shopping nearby. This super clean unit features rich laminate floors, a neutral color palette, lots of natural light, a balcony, and views of the community pool and hot tub. The kitchen features granite counter tops, wood cabinets, a bar top with a pass through window, and

  Kyle Petteway EXIT REAL ESTATE RESULTS

  2905 Antique Oaks Cir Unit 4, Winter Park, FL 32792
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  /2

  $560,000 Sold Aug 20, 2025

  1901 Loch Berry Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • Built 1957

  Last Sold Summary

  • 1% Below List Price
  • $394/SF
  • 7 Days On Market

  Current Estimated Value $550,466

  Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

  1901 Loch Berry Rd, Winter Park, FL 32792
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  /24

  Est $189,749 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  229 Lewfield Cir Unit 229, Winter Park, FL 32792

  229 Lewfield Cir Unit 229, Winter Park, FL 32792
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  $1,989,300

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  2614 Parkland Dr, Winter Park, FL 32789

  The only home priced under $2MM that has over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space,

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
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  /31

  $1,599 - $1,845 per month

  POSTE Winter Park

  1 - 2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  800 Semoran Park Dr, Winter Park, FL 32792
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  $916,000 Sold Jul 17, 2025

  609 Langholm Dr, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $462/SF
  • 8 Days On Market

  Current Estimated Value $910,445

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
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  Est $1,901,867 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,954 Sq Ft

  1433 Sarazens Place, Winter Park, FL 32792

  1433 Sarazens Place, Winter Park, FL 32792
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  /5

  $2,350,000

  • Land
  • 0.55 Acre
  • $4,272,727 per Acre

  1205 Mayfield Ave, Winter Park, FL 32789

  A rare estate-sized double lot in one of Winter Park’s most coveted and established neighborhoods—Temple Heights. This expansive property offers an exceptional opportunity to build a custom luxury residence in one of Central Florida’s most sought-after locations. Nestled in a quiet, tree-lined residential pocket, this oversized parcel provides the space, privacy, and prestige rarely available in

  Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
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  $1,700 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Townhouse for Rent

  7425 Wynnewood Square Unit 176, Winter Park, FL 32792

  This expansive condominium features two bedrooms and two and a half bathrooms. The primary and secondary bedrooms are situated on the upper level, each equipped with an en-suite bathroom. Both bedrooms are adorned with wooden flooring, while the remainder of the unit is tiled throughout. The living and dining areas are combined, enhanced by a mini bar surrounded by mirrors. The kitchen includes a

  Dee Diaz ZAID ROYALE REALTY PLLC

  7425 Wynnewood Square Unit 176, Winter Park, FL 32792
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  $2,599,000 Sold Feb 14, 2025

  1000 Via Tuscany Oaks Way, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,002 Sq Ft
  • Built 2003

  Last Sold Summary

  • $649/SF
  • 2 Days On Market

  Current Estimated Value $2,564,670

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1000 Via Tuscany Oaks Way, Winter Park, FL 32789
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  Est $557,113 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789
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  $650,000

  • 5 Beds
  • 3 Baths
  • 1,917 Sq Ft

  352 Cambridge Blvd, Winter Park, FL 32789

  This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from three separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a dedicated study. A large screened-in

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  352 Cambridge Blvd, Winter Park, FL 32789
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  /35

  $1,750 - $2,750 per month

  Hannibal Square

  2 Beds

  433 W New England Ave, Winter Park, FL 32789

  We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

  433 W New England Ave, Winter Park, FL 32789
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  $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

  Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

  2421 Summerfield Rd, Winter Park, FL 32792
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  /24

  Est $830,557 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789
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  $550,000

  • 3 Beds
  • 2 Baths
  • 1,115 Sq Ft

  720 N Pennsylvania Ave, Winter Park, FL 32789

  Nestled in one of Winter Park’s most sought-after locations, this 3-bedroom, 2-bathroom home seamlessly blends modern elegance with everyday comfort. From the moment you step inside, you'll be captivated by the sleek, contemporary finishes, recessed lighting, and stylish fixtures that enhance every space. The open living and dining room combo creates a bright and welcoming atmosphere, perfect for

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  720 N Pennsylvania Ave, Winter Park, FL 32789
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  /46

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  2021 Canny Cove, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to Winter Park! This 3-bedroom, 2.5-bath townhome in Grayson Square offers an open-concept living and dining area, ideal for entertaining, with a covered rear lanai. The kitchen features stainless steel appliances, quartz countertops, and ample cabinet space. Abundant storage is found throughout the home. The owner’s suite includes a

  Denise Del Castillo LPT REALTY, LLC

  2021 Canny Cove, Winter Park, FL 32792
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  $498,000 Sold May 28, 2025

  808 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1961

  Last Sold Summary

  • $286/SF
  • 4 Days On Market

  Current Estimated Value $488,873

  Last Listing Agent Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

  808 Denton Rd, Winter Park, FL 32792
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  Est $253,122 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft

  200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792

Showing Results 201 - 240, Page 6 of 18