Winter Park, FL Homes

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  $1,295,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,363 Sq Ft

  800 Hamilton Place Ct, Winter Park, FL 32789

  Custom-built and beautifully maintained, this large 3-bedroom home with loft is located in prime Old Winter Park on a quiet cul-de-sac. The interior boasts 18'+ high ceilings, creating a grand and airy atmosphere throughout the main living spaces. High-end finishes include Viking stainless steel appliances, dolomite marble tile flooring, and a thoughtfully designed, functional layout ideal for

  Julian Torres, Jr EPIC REAL ESTATE ADVISORS LLC

  800 Hamilton Place Ct, Winter Park, FL 32789
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  /14

  $1,250 - $1,800 per month

  Park Apartments

  1 - 3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  WELCOME TO THE PARK APARTMENTS (NEWLY RENOVATED!) Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two

  7528 Park Promenade Dr, Winter Park, FL 32792
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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

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

  1445 Holts Grove Cir, Winter Park, FL 32789
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  /30

  Est $1,359,206 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,734 Sq Ft

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789
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  $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 OAKSTRAND REALTY

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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  /16

  $1,295 per month

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Townhouse for Rent

  2183 Crandon Ave Unit 1/2, Winter Park, FL 32789

  This 2 bedroom, 1 bathroom, 2nd floor unit is located in the heart of Winter Park. Enjoy all of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious living area, a lovely kitchen, a screened patio area, and a shared laundry room

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  2183 Crandon Ave Unit 1/2, Winter Park, FL 32789
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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 $548,258

  Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

  1901 Loch Berry Rd, Winter Park, FL 32792
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  /2

  Est $851,235 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,610 Sq Ft

  1245 Wisconsin Ave, Winter Park, FL 32789

  1245 Wisconsin Ave, Winter Park, FL 32789
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  /23

  $420,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,477 Sq Ft

  1847 Azalea Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. 32789 Zip Code! Welcome Home to 1847 Azalea Ave! Discover the charm and convenience of this beautiful one-story home located in the heart of Winter Park. The home is complete with 4 Bedrooms, 2.5 Bathrooms, and 1,477 square feet of living space. This recently renovated property offers brand new features throughout and is move-in ready, ideal for a first

  Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
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  /11

  $1,146 - $1,836 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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  /2

  $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 $902,303

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
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  /36

  Est $192,454 Not Listed For Sale

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

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792
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  /36

  $359,500

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft

  7580 Aloma Pines Ct, Winter Park, FL 32792

  Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location and this 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with

  Simon Colak USCO CAPITAL GROUP

  7580 Aloma Pines Ct, Winter Park, FL 32792
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  /16

  $2,150 per month

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

  151 N Orlando Ave Unit 226, Winter Park, FL 32789

  Updated 2 bedrooms 1 bath conveniently located next to Winter Park Village and Trader Joes shopping center. Unit is can be furnished and is also for sale.

  Mike Wang LOKATION

  151 N Orlando Ave Unit 226, Winter Park, FL 32789
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  /2

  $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 $2,550,392

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1000 Via Tuscany Oaks Way, Winter Park, FL 32789
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  /2

  Est $138,135 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  289 Lewfield Cir, Winter Park, FL 32792

  289 Lewfield Cir, Winter Park, FL 32792
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  $480,000 Pending

  • 5 Beds
  • 3 Baths
  • 1,546 Sq Ft

  3319 Ellwood Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. The pool home you’ve been waiting for is here! Welcome to this beautifully renovated 5-bedroom, 3-bathroom home offering 1,546 SF of living space, abundant natural light in every room, a spacious screened porch, a private pool, and a Mother-in-law Suite with its own private entrance—perfect for guests, multi-generational living, or rental income. The

  Elena Sanchez BALDWIN PARK REALTY LLC

  3319 Ellwood Ct, Winter Park, FL 32792
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  /29

  $1,360 - $1,863 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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  /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

  Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

  2421 Summerfield Rd, Winter Park, FL 32792
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  Est $223,525 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  220 Lewfield Cir, Winter Park, FL 32792

  220 Lewfield Cir, Winter Park, FL 32792
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  $800,000

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  1780 Bryan Ave, Winter Park, FL 32789

  Discover a truly unique offering in the heart of Winter Park! This property, located at 1780 Bryan Avenue, is being offered along with theadjoining lots at 1760 and 1770 Bryan Avenue. While available together as a rare collection of three consecutive parcels, each lot is also being sold separately at individual prices, giving buyers the flexibility to purchase one, two, or all three.

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1780 Bryan Ave, Winter Park, FL 32789
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  /19

  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • House for Rent

  1931 Carrigan Ave, Winter Park, FL 32792

  An excellent place to call home. This newly renovated 3 bedroom 2 bath house offers a lot of entertainment options; it is sitting on an oversize lot which features ample backyard space which is completely fenced. This home has brand new AC, Plumbing and Electric and offers washer/dryer hookups. Close to A+ schools and is approximately 7 minutes from Park Ave shopping and dining. This will not

  Amanda Beckman RED DOOR INVESTMENT GRP LLC

  1931 Carrigan Ave, Winter Park, FL 32792
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  /2

  $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 $489,763

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

  808 Denton Rd, Winter Park, FL 32792
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  /18

  Est $159,691 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  2929 Antique Oaks Cir Unit 49, Winter Park, FL 32792

  2929 Antique Oaks Cir Unit 49, Winter Park, FL 32792
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  /25

  $409,000

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

  3425 Ferndell Dr, Winter Park, FL 32792

  Fully Renovated Gem in Winter Park!Welcome to your dream home in one of Central Florida’s most sought-after neighborhoods—Winter Park. This beautifully renovated 3-bedroom, 2-bathroom residence blends timeless charm with modern updates, offering the perfect move-in-ready sanctuary for today’s lifestyle.Step inside and fall in love with the light-filled open layout, anchored by a stunning

  Ivanhoe Alvarez LOKATION

  3425 Ferndell Dr, Winter Park, FL 32792
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  /35

  $1,575 - $1,895 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

  $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

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

  2171 Forrest Rd, Winter Park, FL 32789
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  /21

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft

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

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792
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  /48

  $669,000

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

  1174 Wildmeadow Run, Winter Park, FL 32792

  Welcome to Hawks Crest – Winter Park’s premier gated, resort-style community! This beautifully appointed home features a timeless terracotta tile roof, elegant plantation shutters, and durable tile flooring throughout the main living areas and carpet in the bedrooms. Designed with comfort and convenience in mind, the home is wheelchair accessible and already prepped for solar panels and security

  Jen Marks CHARLES RUTENBERG REALTY ORLANDO

  1174 Wildmeadow Run, Winter Park, FL 32792
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  /49

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • House for Rent

  332 Harris Ave, Winter Park, FL 32789

  This quaint three-bedroom, two-bathroom residence is ideally situated on a corner lot on a tranquil street. The property has been nicely maintained, both internally and externally. The interior boasts a bright and airy atmosphere, featuring a generously sized great room and a spacious eat-in kitchen with ample cabinetry and storage. Outdoors, residents will discover an oasis of beautifully

  Flory Clark UNITED REAL ESTATE PREFERRED

  332 Harris Ave, Winter Park, FL 32789
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  /2

  $9,140,000 Sold Jan 15, 2025

  2040 Venetian Way, Winter Park, FL 32789

  • 6 Beds
  • 7.5 Baths
  • 8,082 Sq Ft
  • Built 2002

  Last Sold Summary

  • 9% Below List Price
  • $1,131/SF
  • 45 Days On Market

  Current Estimated Value $9,023,481

  Last Listing Agent Thomas Bonner COLDWELL BANKER RESIDENTIAL RE

  2040 Venetian Way, Winter Park, FL 32789
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  /24

  Est $191,814 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792
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  /17

  $918,000

  • 5 Beds
  • 3.5 Baths
  • 3,598 Sq Ft

  5325 Cypress Reserve Place, Winter Park, FL 32792

  ATTENTION BUYERS!! Price adjusted to $918,000 and $15K SELLER CONCESSION TOWARDS BUYERS CLOSING COST WITH FULL ASKING PRICE!!The Winter Park Oasis You've Been Waiting For:Imagine waking up in an expansive primary suite, enjoying a cup of coffee by the fireplace, and then stepping out to your backyard oasis the heated, screened-in pool and spa, warmed by eco-friendly solar panels, are

  Dori Estrada LPT REALTY, LLC

  5325 Cypress Reserve Place, Winter Park, FL 32792
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  /31

  $1,449 - $1,705 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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  $435,000 Sold Jan 22, 2025

  1944 Bering Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 1,956 Sq Ft
  • Built 1958

  Last Sold Summary

  • 2% Above List Price
  • $222/SF
  • 13 Days On Market

  Current Estimated Value $449,162

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES

  1944 Bering Ave, Winter Park, FL 32789
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  /22

  Est $154,103 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 237, Winter Park, FL 32789

  2500 Lee Rd Unit 237, Winter Park, FL 32789
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  /31

  $185,000 Pending

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

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

  Under contract-accepting backup offers. Welcome to Parkview Village — one of Winter Park’s most convenient and sought-after condo communities! This move-in ready 2-bedroom, 2-bathroom first-floor end unit offers a perfect blend of comfort and location. Step inside to find a bright, open-concept living and dining area with tile flooring throughout the main spaces and new luxury vinyl plank in both

  Chris Bessette KELLER WILLIAMS CLASSIC

  2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792
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  $3,700 per month

  • 5 Beds
  • 3 Baths
  • 2,132 Sq Ft
  • House for Rent

  730 W Swoope Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Charming Winter Park Corner Home for Rent - 730 W Swoope Ave Experience the best of Winter Park living in this beautifully renovated corner home! Located just three blocks from the iconic Park Avenue, this spacious 5-bedroom, 3 bathroom residence offers over 2,200 square feet of updated living space. The bright, open design and private rooms provide

  Andres Ospina Rivera LPT REALTY, LLC

  730 W Swoope Ave, Winter Park, FL 32789
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  /2

  $520,000 Sold Mar 31, 2025

  1810 Taylor Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Below List Price
  • $372/SF
  • 0 Days On Market

  Current Estimated Value $532,311

  Last Listing Agent Julia Dalessandro FANNIE HILLMAN & ASSOCIATES

  1810 Taylor Ave, Winter Park, FL 32789
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  Est $3,193,865 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,367 Sq Ft

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  140 E Morse Blvd Unit G, Winter Park, FL 32789

Showing Results 201 - 240, Page 6 of 18