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540 Properties Available In Winter Park
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$2,575,000
Single Family Home
1795 GREENWICH AVE, Winter Park, FL 32789
Welcome to a one-of-a-kind, custom-designed residence offering the perfect blend of modern sophistication, thoughtful fu...
Listed by KELLY PRICE & COMPANY LLC


$1,299,000
Single Family Home
1341 LYNDALE BLVD, Winter Park, FL 32789
Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park V...
Listed by COMPASS FLORIDA LLC


$2,295,000
Single Family Home
2614 PARKLAND DR, Winter Park, FL 32789
Welcome to 2614 Parkland Drive—an exquisite, fully renovated luxury residence nestled in the heart of Winter Park, Flori...
Listed by JW GASTON LLC


$1,550,000
Single Family Home
1661 WOODLAND AVE, Winter Park, FL 32789
Fabulous Top-to-Bottom Renovation on Coveted Brick Street in Prime Winter Park Location! This exceptional 3-bedroom, 3.5...
Listed by FANNIE HILLMAN & ASSOCIATES


$699,900
Single Family Home
2817 PRINCE JOHN RD, Winter Park, FL 32792
NEW ROOF 2019! SPECTACULAR WINTER PARK HOME COMPLETELY RENOVATED AND UPGRADED INCLUDING A STUNNING KITCHEN! This four be...
Listed by LORI GILMORE REAL ESTATE LLC


$569,999
Single Family Home
7730 BROKEN ARROW TRL, Winter Park, FL 32792
Welcome to this inviting 3-bedroom, 2-bathroom home, perfectly situated on a spacious lot that offers peace, privacy, an...
Listed by LA ROSA REALTY PREMIER LLC


$1,200,000
Condo
100 S INTERLACHEN AVE #304, Winter Park, FL 32789
Sit back and relax on two private balconies with pool and lake views. This combined unit has the largest square footage ...
Listed by FANNIE HILLMAN & ASSOCIATES


$349,990
Single Family Home
320 GRANADA DR, Winter Park, FL 32789
Welcome to this delightful 3-bedroom, 2-bathroom home nestled in the heart of sought-after Winter Park! Bursting with ch...
Listed by KELLER WILLIAMS WINTER PARK


$675,000
Single Family Home
796 MCINTYRE AVE, Winter Park, FL 32789
Welcome to 796 McIntyre Avenue, Winter Park, FL 32789. This stunning and serene retreat is the ideal place to call home,...
Listed by FANNIE HILLMAN & ASSOCIATES


$479,900
Single Family Home
1532 LAWNDALE CIR, Winter Park, FL 32792
Welcome to Your Florida Oasis in Winter Park! <br> <br>This beautifully maintained 4-bedroom, 3-bathroom home offers 2,0...
Listed by KELLER WILLIAMS WINTER PARK


$575,000
Single Family Home
2007 STRATHAVEN ROAD, Winter Park, FL 32792
Updated, immaculate and move-in ready! You'll love everything about this 4BR classic ranch style home in Kenilworth Shor...
Listed by EXP REALTY LLC


$385,000
Single Family Home
5144 ORANGE AVE, Winter Park, FL 32792
One or more photo(s) has been virtually staged. PRICED TO SELL! NEW ROOF, UPDATED PANEL BOX, UPDATED KITCHEN. Welcome Ho...
Listed by WEMERT GROUP REALTY LLC


$349,000
Single Family Home
3204 NETHERWOOD, Winter Park, FL 32792
Discover this beautifully renovated 2-bedroom, .5 -bathroom villa in the heart of Winter Park! Nestled on a private cul-...
Listed by WATSON REALTY CORP.


$415,000
Single Family Home
5144 GOLDENROD PLACE RD, Winter Park, FL 32792
Nestled on an oversized lot at the end of a peaceful cul-de-sac, this charming home offers the perfect blend of privacy ...
Listed by C. APOLLO REALTY INC


$420,000
Single Family Home
1041 MANCHESTER CIR, Winter Park, FL 32792
Incredible Winter Park Location! <br>This spacious 4-bedroom, 2-bathroom pool home is situated in a highly desirable are...
Listed by COLDWELL BANKER RESIDENTIAL RE


$2,150,000
Single Family Home
1560 WOODLAND AVE, Winter Park, FL 32789
You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situ...
Listed by LOKATION


$2,100,000
Single Family Home
4469 OLD BEAR RUN, Winter Park, FL 32792
Welcome to this amazing custom home located on PRIVATE BEAR GULLY LAKE, with 137 ACRES OF GORGEOUS WATERFRONT! This stun...
Listed by HOME WISE REALTY GROUP, INC.


$600,000
Single Family Home
2310 CADY WAY, Winter Park, FL 32792
Welcome home to the sought after neighborhood of Brookshire Heights with in the Greater Winter Park Pines Community, whe...
Listed by KELLER WILLIAMS WINTER PARK


$425,000
Single Family Home
7602 GLENMOOR LN, Winter Park, FL 32792
Welcome to this beautifully maintained 3-bedroom, 2-bathroom single-family home in the heart of Winter Park, FL! Featuri...
Listed by KELLER WILLIAMS REALTY AT THE PARKS


$483,700
Single Family Home
1776 E CHERYL DR, Winter Park, FL 32792
Welcome to 1776 E Cheryl Dr, located on a quiet cul-de-sac in desirable Winter Park. The home offers a split plan with 4...
Listed by MINK REALTY


$565,000
Single Family Home
230 S RANGER BLVD, Winter Park, FL 32792
Beautifully updated and FURNISHED (upon negotiation) 3-bedroom, 2-bath home in the desirable Winter Park Pines neighborh...
Listed by KELLY PRICE & COMPANY LLC


$2,895,000
Single Family Home
1630 LASBURY AVE, Winter Park, FL 32789
Nestled on a serene, brick-paved street in the heart of Winter Park, this elegant 5-bedroom, 3.2-bathroom pool home is s...
Listed by FANNIE HILLMAN & ASSOCIATES


$489,900
Condo
535 N INTERLACHEN AVE #107, Winter Park, FL 32789
Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor...
Listed by FANNIE HILLMAN & ASSOCIATES


$450,000
Single Family Home
4991 TANGERINE AVE, Winter Park, FL 32792
Welcome to 4991 Tangerine Ave in the heart of Winter Park! This charming 4-bedroom, 2-bathroom home offers comfortable l...
Listed by KELLER WILLIAMS ADVANTAGE REALTY
