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230 Properties Available
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$1,499,900
Single Family Home
130 W KINGS WAY, Winter Park, FL 32789
Amazing opportunity in the Forest Hills subdivision in the heart of Historic Winter Park! As you enter this charming 4 b...
Listed by


$929,900
Single Family Home
2823 WRIGHT AVE, Winter Park, FL 32789
Here's your chance to own something truly special in Winter Park! This gorgeous lakefront home sits on over HALF AN ACRE...
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$950,000
Single Family Home
668 OVERSPIN DR, Winter Park, FL 32789
Modern Elegance Meets Custom Craftsmanship in the Heart of Winter Park <br>Welcome to your dream home — a custom-built W...
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$140,000
Condo
1695 LEE RD #C214, Winter Park, FL 32789
Charming 2-bedroom, 1-bath condo located in the heart of Winter Park. This well-maintained unit offers comfortable livin...
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$354,900
Single Family Home
611 OLOLU DR, Winter Park, FL 32789
RARE FIND! MUST SEE! PRIME LOCATION! NO HOA! Check out this 3 bedroom 2 bath gem in the heart of beautiful Winter Park. ...
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$2,795
Single Family Home
313 GRANADA DR, Winter Park, FL 32789
Four bedroom, two bathroom, single family home with carport and outdoor laundry/utility/storage room. Located in the Fai...
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$1,995,000
Single Family Home
1612 MAGNOLIA AVE, Winter Park, FL 32789
Welcome home to 1612 Magnolia Avenue. Built by the renowned custom home builder Lundev, this beautifully crafted transit...
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$1,129,000
Condo
100 S VIRGINIA AVE #314, Winter Park, FL 32789
RARE OPPORUNITY to Experience refined living in the heart of Winter Park with this exceptional and spacious 3-bedroom, 3...
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$1,634,900
Single Family Home
1510 MILLER AVE, Winter Park, FL 32789
Under Construction. New Construction – Modern Luxury Meets Urban Living at Winter Park's Newest Neighborhood, Winter Par...
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$198,800
Condo
700 MELROSE AVE #D21, Winter Park, FL 32789
Located in the historic Winter Park Gardens community, this condo has been meticulously maintained and updated. Featurin...
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$8,950,000
Single Family Home
1120 PRESERVE POINT DR, Winter Park, FL 32789
In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private ...
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$550,000
Condo
535 N INTERLACHEN AVE #203, Winter Park, FL 32789
Experience effortless luxury living just blocks from iconic Park Avenue in this stunning, fully renovated condo located ...
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$479,000
Single Family Home
260 ORANGE TERRACE DR, Winter Park, FL 32789
Under contract-accepting backup offers. What a great location - Ready for move in before the holidays! Don't miss this ...
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$3,100
Single Family Home
240 ORANGE TERRACE DR, Winter Park, FL 32789
Spacious 4 bedroom, 2 bath home in a quiet neighborhood just minutes from I-4 and Fairbanks. Convenient to downtown Orla...
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$2,190,000
Single Family Home
2001 LAKE DR, Winter Park, FL 32789
Nestled on a quiet cul-de-sac in the heart of Winter Park, this canal-front residence offers the perfect balance of eleg...
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$2,350,000
Single Family Home
1268 PRESERVE POINT DR, Winter Park, FL 32789
Stunning custom residence in the highly sought-after Windsong community, built by Hal George of Parkland Homes and desig...
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$1,990,000
Single Family Home
319 SANTIAGO DR, Winter Park, FL 32789
Nestled in coveted Winter Park's Sevilla neighborhood, this 4-bed, 4.5-bath pool home delivers 3,500+ SF of refined livi...
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$439,000
Single Family Home
1872 BISCAYNE DR, Winter Park, FL 32789
Don't miss this rare opportunity to own a professionally landscaped, beautifully maintained home in Winter Park, perfect...
Listed by


$17,550
Single Family Home
1860 VIA CONTESSA, Winter Park, FL 32789
Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted ...
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$1,850
Single Family Home
460 CAMBRIDGE BLVD #B, Winter Park, FL 32789
460 B Cambridge is a beautifully updated 2 bed / 2 bath home offering 945 sq ft of stylish living space. Every detail ha...
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$3,350,000
Single Family Home
1900 W FAWSETT RD, Winter Park, FL 32789
Don't miss the opportunity to own this stunning lakefront property on Lake Sue in Winter Park! Over an acre with 125+ fe...
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$275,000
Condo
1500 GAY RD #24B, Winter Park, FL 32789
Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dolla...
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$10,500
Single Family Home
1530 VIA TUSCANY, Winter Park, FL 32789
Newly Remodeled Pool home located on premier street in Winter Park. This 4 bedroom home has just been totally updated wi...
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$325,000
Condo
1308 S PENNSYLVANIA AVE #3, Winter Park, FL 32789
This beautifully updated 1-bedroom, 1-bath condo offers 823 sq. ft. of stylish living space in one of Central Florida's ...
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