Winter Park, FL Homes

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  /22

  $550,000 Open Sat 1PM - 3PM

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

  720 W Webster Ave, Winter Park, FL 32789

  Discover the charm of Winter Park living in this beautifully maintained 1950s home, where convenience and comfort meet modern updates. Just minutes from Park Avenue and Winter Park Village, this 3-bedroom, 2-bath residence offers a lifestyle surrounded by boutique shopping, dining, and cultural experiences.Inside, rich wood flooring, natural light, and thoughtful touches create a warm and

  Brian Hyser THE AGENCY FL

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

  $2,835,000 Sold Nov 24, 2025

  255 Stirling Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,635 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $780/SF
  • 25 Days On Market

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

  255 Stirling Ave, Winter Park, FL 32789
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  /32

  Est $463,898 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  2445 Firstlight Way, Winter Park, FL 32792

  2445 Firstlight Way, Winter Park, FL 32792
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  /25

  $329,900

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

  Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
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  /2

  $1,430,000 Sold Nov 10, 2025

  1011 Mckean Cir, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 1955

  Last Sold Summary

  • $641/SF
  • 0 Days On Market

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  1011 Mckean Cir, Winter Park, FL 32789
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  /62

  Est $2,035,995 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 7,762 Sq Ft

  2156 Talman Ct, Winter Park, FL 32792

  2156 Talman Ct, Winter Park, FL 32792
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  /24

  $435,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft

  1306 Merrydale Way, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. MERITAGE BUILDER HOME- PRICE IMPROVEMENT - OWNER MOTIVATED - WILLING TO HELP WITH CLOSING COSTS OR RATE BUY DOWN. Welcome to the Enclave at Hawks Crest, a newly built GATED luxury townhomecommunity in sought-after Winter Park, and this 3BD/2.5BA home with a bright open floor plan, UPGRADES throughout,

  Claire Sims LLC LPT REALTY, LLC

  1306 Merrydale Way, Winter Park, FL 32792
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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 $436,025

  Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

  1945 Bering Ave, Winter Park, FL 32789
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  /20

  Est $473,244 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  2448 Firstlight Way, Winter Park, FL 32792

  2448 Firstlight Way, Winter Park, FL 32792
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  /17

  $634,900

  • 3 Beds
  • 1.5 Baths
  • 2,108 Sq Ft

  5150 Old Howell Branch Rd, Winter Park, FL 32792

  A Rare Live/Work Opportunity! Work from home or utilize the space as an office, retail, daycare, or other permitted use. This fully renovated property includes two adjoining parcels: the main lot with the building, plus a vacant lot (50' x 155') offering future expansion potential for an additional structure, subject to zoning and county regulations. With a sought-after Winter Park address, the

  John Sadri JOHN SADRI & COMPANY

  5150 Old Howell Branch Rd, Winter Park, FL 32792
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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 $833,360

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

  Unlisted Address
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  /22

  Est $194,101 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792
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  /34

  $1,599,900 New Construction

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  607 Ellen Dr, Winter Park, FL 32789

  Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting

  Kelly Price KELLY PRICE & COMPANY LLC

  607 Ellen Dr, 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

  Current Estimated Value $2,558,211

  Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

  1341 Place Picardy, Winter Park, FL 32789
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  /77

  Est $774,843 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7904 Pleasant Pine Cir, Winter Park, FL 32792

  7904 Pleasant Pine Cir, Winter Park, FL 32792
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  /22

  $298,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 115, Winter Park, FL 32789

  Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake

  Chris Creegan CREEGAN GROUP

  151 N Orlando Ave Unit 115, Winter Park, FL 32789
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  /2

  $340,000 Sold Feb 12, 2025

  5134 Lake Howell Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,399 Sq Ft
  • Built 1957

  Last Sold Summary

  • $243/SF
  • 8 Days On Market

  Current Estimated Value $340,455

  Last Listing Agent Dawn Tinder KELLER WILLIAMS WINTER PARK

  5134 Lake Howell Rd, Winter Park, FL 32792
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  /28

  Est $270,086 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  7113 Swallow Run Unit 2, Winter Park, FL 32792

  7113 Swallow Run Unit 2, Winter Park, FL 32792
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  /8

  $358,000

  • Land
  • 0.16 Acre
  • $2,237,500 per Acre

  2002 Indiana Ave, Winter Park, FL 32789

  Great buildable lot centrally located close to I-4 for easy access. Currently zoned R-2 for multifamily housing 2+ units possible. Please consult the zoning and planning Dept. for info and guidelines for building. The lot has single family homes on both sides of it and faces a retention pond area across the street. Front half of the lot is cleared. Back half of the lot is wooded. Paved road

  David Nicholson DAWN REALTY

  2002 Indiana Ave, Winter Park, FL 32789
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  /2

  $435,000 Sold Aug 31, 2025

  2209 Fairglenn Way, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,027 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Below List Price
  • $215/SF
  • 54 Days On Market

  Current Estimated Value $450,500

  Last Listing Agent Benjamin Benami CHARLES RUTENBERG REALTY ORLANDO

  2209 Fairglenn Way, Winter Park, FL 32792

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