Winter Park, FL Homes

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  /29

  Est $334,676 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3113 Crown Jewel Ct, Winter Park, FL 32792

  3113 Crown Jewel Ct, Winter Park, FL 32792
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  /41

  $499,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft

  2381 Roxbury Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Live the Winter Park dream in this freshly updated 3-bedroom, 2-bath home—just steps from Lake Killarney and minutes to I-4, boutique shopping, and top dining spots. The interior has been freshly painted, creating a bright and welcoming feel throughout. The updated kitchen shines with white shaker cabinets, quartz countertops, a subway-tile

  Alex Vastardis COLDWELL BANKER REALTY

  2381 Roxbury Rd, Winter Park, FL 32789
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  /2

  $439,900 Sold Jul 22, 2025

  1945 Bering Ave, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,576 Sq Ft
  • Built 1958

  Last Sold Summary

  • $279/SF
  • 6 Days On Market

  Current Estimated Value $434,268

  Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

  1945 Bering Ave, Winter Park, FL 32789
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  /11

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  1405 Miller Ave, Winter Park, FL 32789

  1405 Miller Ave, Winter Park, FL 32789
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  /43

  $525,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,870 Sq Ft

  1817 Jessica Ct, Winter Park, FL 32789

  Under contract-accepting backup offers. Beautifully situated on an elevated 50-by-106-foot lot in the Waterbridge community, this spacious single-story home enjoys a quiet cul-de-sac setting overlooking a small neighborhood park and is adjacent to a green space that enhances privacy. The property has wonderful curb appeal with mature trees, a wide driveway, an oversized two-car garage, and an

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1817 Jessica Ct, Winter Park, FL 32789
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  /2

  $799,000 Sold Apr 08, 2025

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 2,331 Sq Ft
  • Built 1952

  Last Sold Summary

  • $343/SF
  • 3 Days On Market

  Current Estimated Value $833,747

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

  Unlisted Address
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  /19

  Est $276,609 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 939 Sq Ft

  2404 Gallery View Dr Unit 1, Winter Park, FL 32792

  2404 Gallery View Dr Unit 1, Winter Park, FL 32792
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  /12

  $1,690,000

  • Land
  • 0.51 Acre
  • $3,313,725 per Acre

  141 W Lake Sue Ave, Winter Park, FL 32789

  AMAZING Winter Park Opportunity! Nestled in one of the most desirable locations, 141 W Lake Sue Avenue offers a VERY HARD to find 1⁄2 acre lot—the epitome of prime real estate. Making this a rare chance for builders or buyers to create their dream Winter Park residence on this corner lot at Glencoe & Lake Sue Avenue. Surrounded by beautiful homes and tree-lined streets, this pristine lot provides

  Brian Mitnik RE/MAX 200 REALTY

  141 W Lake Sue Ave, Winter Park, FL 32789
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  /2

  $227,100 Sold Jan 21, 2025

  2494 Timberline Dr, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $173/SF
  • 57 Days On Market

  Current Estimated Value $242,027

  Last Listing Agent Crystal Whitehead CREEGAN GROUP

  2494 Timberline Dr, Winter Park, FL 32792
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  /34

  Est $241,081 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  1925 Woodcrest Dr Unit E, Winter Park, FL 32792

  1925 Woodcrest Dr Unit E, Winter Park, FL 32792
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  /47

  $639,000

  • 3 Beds
  • 2 Baths
  • 1,619 Sq Ft

  2817 Fitzooth Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Discover the perfect blend of modern upgrades and effortless living in this beautifully updated pool home located in the highly desirable Winter Park Pines community. Set on a spacious corner lot, this move-in-ready residence features a bright open-concept floor plan filled with natural light and upgraded finishes throughout. The remodeled kitchen

  Diego Trujillo-Castillo DJ & LINDSEY REAL ESTATE

  2817 Fitzooth Dr, Winter Park, FL 32792
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  /2

  $299,000 Sold Jan 08, 2025

  222 Balfour Dr Unit 14, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1985

  Last Sold Summary

  • 12% Below List Price
  • $238/SF
  • 206 Days On Market

  Current Estimated Value $301,907

  Last Listing Agent Tricia Ramsby BHHS FLORIDA REALTY

  222 Balfour Dr Unit 14, Winter Park, FL 32792
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  /31

  Est $769,873 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  2312 Kestrel Perch Place, Winter Park, FL 32792

  2312 Kestrel Perch Place, Winter Park, FL 32792
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  /13

  $455,000

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  2206 Bonanza Ave, Winter Park, FL 32792

  Beautiful home in Winter Park, located in a quiet neighborhood with no homeowner association fees. This 4-bedroom, 2-bathroom home has been recently remodeled, including new bathrooms, new flooring, new quartz countertops, new kitchen cabinets, a new 2025 central air conditioning unit, a 2023 roof, and a new 2025 water heater. It features a 2-car garage and ample parking, as well as a renovated

  Pia Jijon Garcia AGENT TRUST REALTY CORPORATION

  2206 Bonanza Ave, Winter Park, FL 32792
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  /2

  $285,000 Sold Jan 23, 2025

  5173 Lazy Oaks Dr, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,236 Sq Ft
  • Built 1984

  Last Sold Summary

  • 5% Below List Price
  • $231/SF
  • 107 Days On Market

  Current Estimated Value $281,012

  Last Listing Agent Kathleen Harrison CALL IT CLOSED INTL REALTY

  5173 Lazy Oaks Dr, Winter Park, FL 32792
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  /18

  Est $188,758 Not Listed For Sale

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

  2911 Antique Oaks Cir Unit GE, Winter Park, FL 32792

  2911 Antique Oaks Cir Unit GE, Winter Park, FL 32792
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  /50

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft

  1400 S Pennsylvania Ave, Winter Park, FL 32789

  Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. You will be amazed at this fully remodeled one level four bedroom home on a fenced corner lot. This home has amazing curb appeal, with its wide half circle paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living

  Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
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  /2

  $2,575,000 Sold Oct 20, 2025

  1341 Place Picardy, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,469 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $576/SF
  • 95 Days On Market

  Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

  1341 Place Picardy, Winter Park, FL 32789
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  /24

  Est $333,337 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3173 Crown Jewel Ct, Winter Park, FL 32792

  3173 Crown Jewel Ct, Winter Park, FL 32792
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  /36

  $1,050,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  632 Country Club Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards

  Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

  632 Country Club Dr, Winter Park, FL 32789

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