Winter Park, FL Homes

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  /17

  Est $444,753 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2760 Bright Bird Ln, Winter Park, FL 32792

  2760 Bright Bird Ln, Winter Park, FL 32792
• 

  

  

  /31

  $485,000 Pending

  • 4 Beds
  • 4 Baths
  • 2,000 Sq Ft

  131 Stefanik Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. BRAND NEW ROOF SEPTEMBER 2025! Welcome to this fantastic income-producing duplex, offering the perfect blend of comfort, convenience, and opportunity. Each side features 2 bedrooms and 1.5 bathrooms, with its own attached garage and private driveway. From the moment you arrive, you’ll appreciate the meticulously maintained landscaping that enhances the curb

  Thomas McNamara EXP REALTY LLC

  131 Stefanik Rd, Winter Park, FL 32792
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  /2

  $785,000 Sold Dec 30, 2024

  1005 Fairway Dr, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,584 Sq Ft
  • Built 1973

  Last Sold Summary

  • 13% Below List Price
  • $304/SF
  • 141 Days On Market

  Current Estimated Value $790,711

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1005 Fairway Dr, Winter Park, FL 32792
• 

  

  

  /17

  Est $442,633 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2748 Bright Bird Ln, Winter Park, FL 32792

  2748 Bright Bird Ln, Winter Park, FL 32792
• 

  

  

  /22

  $575,000

  • 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 ORLANDO

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

  $89,750 Sold Dec 05, 2025

  3002 George Mason Ave Unit 3, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,085 Sq Ft
  • Built 1974

  Last Sold Summary

  • 25% Below List Price
  • $83/SF
  • 92 Days On Market

  Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

  3002 George Mason Ave Unit 3, Winter Park, FL 32792
• 

  

  /18

  Est $210,588 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft

  7413 Belle River Ct Unit 3, Winter Park, FL 32792

  7413 Belle River Ct Unit 3, Winter Park, FL 32792
• 

  

  /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

  $755,000 Sold Jul 18, 2025

  1000 Howell Branch Rd, Winter Park, FL 32789

  • Land
  • 0.55 Acre
  • $1,372,727 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 241 Days On Market

  Current Estimated Value $855,172

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1000 Howell Branch Rd, Winter Park, FL 32789
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  /5

  Est $421,937 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,477 Sq Ft

  7494 Betty St, Winter Park, FL 32792

  7494 Betty St, Winter Park, FL 32792
• 

  

  /19

  $739,000

  • 2 Beds
  • 2 Baths
  • 1,305 Sq Ft

  300 Carolina Ave Unit 201, Winter Park, FL 32789

  Experience the best of Winter Park living in this beautifully updated 2-bedroom, 2-bath condominium located in the highly sought-after Park West Condominiums. Perfectly situated just steps from Park Avenue’s restaurants, boutique shops, cafés, and the weekly farmers market, this second-floor residence offers both comfort and convenience in one of Central Florida’s most desirable neighborhoods.

  Teri Webster LPT REALTY, LLC

  300 Carolina Ave Unit 201, Winter Park, FL 32789
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  /2

  $150,000 Sold Mar 18, 2025

  3358 Cedar Springs Place Unit 159, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1984

  Last Sold Summary

  • 33% Below List Price
  • $145/SF
  • 59 Days On Market

  Current Estimated Value $156,606

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC

  3358 Cedar Springs Place Unit 159, Winter Park, FL 32792
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  /3

  Est $2,244,348 Not Listed For Sale

  150 Whipple Ave, Winter Park, FL 32789

  150 Whipple Ave, Winter Park, FL 32789
• 

  

  /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

  $130,000 Sold Nov 25, 2025

  200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft
  • Built 1970

  Last Sold Summary

  • 13% Below List Price
  • $179/SF
  • 35 Days On Market

  Last Listing Agent Mary Marwick PREMIUM PROPERTIES R.E SERVICE

  200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
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  /2

  Est $777,599 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,094 Sq Ft

  2352 Kestrel Perch Place, Winter Park, FL 32792

  2352 Kestrel Perch Place, Winter Park, FL 32792
• 

  

  /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

  $170,000 Sold Sep 24, 2025

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $152/SF
  • 74 Days On Market

  Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
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  /54

  Est $773,559 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,894 Sq Ft

  1155 Wildmeadow Run, Winter Park, FL 32792

  1155 Wildmeadow Run, Winter Park, FL 32792
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  /45

  $1,630,000 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

  $240,000 Sold Mar 03, 2025

  200 Saint Andrews Blvd Unit 2502, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,165 Sq Ft
  • Built 1970

  Last Sold Summary

  • 26% Below List Price
  • $206/SF
  • 217 Days On Market

  Current Estimated Value $236,184

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  200 Saint Andrews Blvd Unit 2502, Winter Park, FL 32792
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  /67

  Est $1,321,298 Not Listed For Sale

  • 7 Beds
  • 5 Baths
  • 5,111 Sq Ft

  1464 Via Sangro Place, Winter Park, FL 32792

  1464 Via Sangro Place, Winter Park, FL 32792
• 

  

  /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

  $325,000 Sold Oct 03, 2025

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 0 Days On Market

  Last Listing Agent Tyler Gibson LPT REALTY, LLC

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
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  /28

  Est $442,677 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2901 Clever Ln, Winter Park, FL 32792

  2901 Clever Ln, Winter Park, FL 32792
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  /44

  $750,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  1712 Golfside Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. The home you’ve been waiting for—an exceptional Winter Park residence offering a private pool and golf views. Situated at 1712 Golfside, this property welcomes you with a picturesque oak-lined street, a paver driveway, and timeless architectural character. Every element has been designed to deliver a sophisticated blend of comfort, style, and effortless

  Shawn McCormick ERA GRIZZARD REAL ESTATE

  1712 Golfside Dr, Winter Park, FL 32792
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  /2

  $415,000 Sold Jun 10, 2025

  3063 Ash Park Loop, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $248/SF
  • 23 Days On Market

  Current Estimated Value $420,801

  Last Listing Agent Cheryl Anderson ANDERSON INVESTMENT PROPERTIES

  3063 Ash Park Loop, Winter Park, FL 32792
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  /32

  Est $686,847 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,592 Sq Ft

  1431 Lake Florence Way, Winter Park, FL 32792

  1431 Lake Florence Way, Winter Park, FL 32792
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  /3

  $3,650,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,719 Sq Ft

  207 E Kings Way, Winter Park, FL 32789

  Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
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  /2

  $385,000 Sold Nov 12, 2025

  4421 Steed Terrace, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Built 1989

  Last Sold Summary

  • 14% Below List Price
  • $215/SF
  • 209 Days On Market

  Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC

  4421 Steed Terrace, Winter Park, FL 32792
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  /14

  Est $730,969 Not Listed For Sale

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

  1407 Miller Ave, Winter Park, FL 32789

  1407 Miller Ave, Winter Park, FL 32789
• 

  

  /20

  $549,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  2412 Middleton Ave, Winter Park, FL 32792

  Gorgeous move in ready or spacious corner lot to build your Dream Home, fully updated 3 bedroom, 2 full bath , corner lot home in a coveted Winter Park neighborhood! The interior is completely renovated throughout, including kitchen with stone countertops, two year old appliances, all new bathrooms with shower glass doors, flooring with plank tiles, two year old A/C unit and air handler, new

  Santiago Borrero REAL ESTATE INVESTMENTS BY BOR

  2412 Middleton Ave, Winter Park, FL 32792
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  /2

  $665,000 Sold Jun 18, 2025

  2817 Prince John Rd, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,183 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $305/SF
  • 37 Days On Market

  Current Estimated Value $655,084

  Last Listing Agent Lori Gilmore LORI GILMORE REAL ESTATE LLC

  2817 Prince John Rd, Winter Park, FL 32792
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  /2

  Est $643,969 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,518 Sq Ft

  756 Friar Rd Unit 13, Winter Park, FL 32792

  756 Friar Rd Unit 13, Winter Park, FL 32792
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  /34

  $725,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  770 W Webster Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Stop the car! Check out this classic 4/2 Florida ranch PLUS vacant lot ready for renovation! Newer roof, water heater. HW and tile floors, screened porch, utility/storage room. 1 car carport. OR develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 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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  /38

  Est $289,759 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  236 Balfour Dr Unit 21, Winter Park, FL 32792

  236 Balfour Dr Unit 21, Winter Park, FL 32792
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  /67

  $895,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,808 Sq Ft

  1802 Arbor Park Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Situated in the highly sought-after Winter Park area and surrounded by tree-lined streets, this stunning move-in ready home is waiting for its new owner. Set on one of the largest lots in the neighborhood, the property greets you with style and charm. Professional landscaping leads you to an inviting open floor plan designed for both family life and

  Jennifer Roberts FLORIDA EXECUTIVE REALTY

  1802 Arbor Park Dr, 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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  /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

Showing Results 641 - 680, Page 17 of 18