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451 Properties Available In Winter Park
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$3,299,000
Single Family Home
255 STIRLING AVE, Winter Park, FL 32789
An incredible Winter Park Chain of Lakes opportunity on Lake Virginia with clear views of Rollins College. This transiti...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$975,000
Single Family Home
2129 FOSGATE DRIVE, Winter Park, FL 32789
Nestled on a quiet street in one of Winter Park's most desirable neighborhoods, this home blends timeless elegance with ...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$699,000
Single Family Home
2825 MULFORD AVE, Winter Park, FL 32789
Welcome to 2825 Mulford Avenue, 'Memorable Mulford,' a charming 2-bedroom, 2-bath bungalow ideally located in Winter Par...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$899,000
Single Family Home
2573 MADELINE AVE, Winter Park, FL 32789
Custom built in 2023, this Winter Park home has it all. Enjoy this quiet pocket of 32789 less than 3 miles from Park Ave...
Listed by LOMBARDO TEAM REAL ESTATE LLC
$430,000
Single Family Home
5122 N WOODCREST DR, Winter Park, FL 32792
This is your chance to own a rare updated 3-bedroom, 2-bath pool home in the heart of Winter Park. This move-in-ready p...
Listed by KELLER WILLIAMS ELITE PARTNERS III REALTY
$2,100,000
Single Family Home
1540 PALM AVE, Winter Park, FL 32789
Welcome to this stunning SINGLE STORY five-bedroom home in one of Winter Park's most desirable neighborhoods, where char...
Listed by FANNIE HILLMAN & ASSOCIATES
$3,495,000
Single Family Home
1821 ENGLEWOOD RD, Winter Park, FL 32789
This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Developmen...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,650,000
Single Family Home
340 ALBERTA DR, Winter Park, FL 32789
Welcome to 340 Alberta Drive, a beautifully maintained 4-bedroom, 4-bath residence with a new roof installed in 2020. Si...
Listed by REAL ESTATE FIRM OF ORLANDO
$1,075,000
Single Family Home
2143 BLOSSOM LN, Winter Park, FL 32789
Winter Park canal front with direct access to Lake Killarney. <br> <br>This 3-bed, 2-bath, split-plan home blends everyd...
Listed by EXP REALTY LLC
$460,000
Single Family Home
3319 ELLWOOD CT, Winter Park, FL 32792
The pool home you've been waiting for is here! Welcome to this beautifully renovated 5-bedroom, 3-bathroom home offering...
Listed by BALDWIN PARK REALTY LLC
$425,000
Single Family Home
5422 ALBERT DR, Winter Park, FL 32792
Welcome home to 5422 Albert Drive this beautifully remodeled 3-bedroom, 2-bathroom home is located in the heart of Winte...
Listed by WATSON REALTY CORP
$399,000
Single Family Home
917 DUPONT AVE, Winter Park, FL 32789
Welcome to this charming mid-century 3-bedroom, 2-bathroom ranch-style home located in the heart of Winter Park, Florida...
Listed by LPT REALTY, LLC
$575,000
Single Family Home
1875 STAUNTON AVE, Winter Park, FL 32789
Welcome to this newer single-family home tucked away in the Karolina On Killarney section of Winter Park. Situated on a ...
Listed by KELLER WILLIAMS WINTER PARK
$499,000
Single Family Home
2485 MIDDLETON AVE, Winter Park, FL 32792
Wait no more! Don't miss this charming and hard to find 3 bed/ 2 bath PLUS bonus room in Brookshire Heights! Large tr...
Listed by KELLER WILLIAMS WINTER PARK
$373,500
Single Family Home
5110 N WOODCREST DR, Winter Park, FL 32792
Discover the perfect blend of comfort and convenience in this beautifully remodeled 3-bedroom, 2-bath home in Winter Par...
Listed by LA ROSA REALTY ORLANDO LLC
$1,165,000
Single Family Home
1450 CHESTNUT AVE, Winter Park, FL 32789
Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timeless Mediterranean home offers t...
Listed by KELLY PRICE & COMPANY LLC
$410,000
Single Family Home
5346 CYPRESS DR, Winter Park, FL 32792
Impeccably cared for and ready for its next chapter, this Winter Park home blends timeless charm with essential modern u...
Listed by KELLER WILLIAMS ADVANTAGE REALTY
$375,000
Single Family Home
2320 HIGH ST, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Enjoy a 1% lower interest rate for your first year with our preferred le...
Listed by THE AGENCY ORLANDO
$1,050,000
Single Family Home
7706 WAUNATTA CT, Winter Park, FL 32792
Stunning Lakefront Retreat in Winter Park! Welcome to your dream home on beautiful Lake Waunatta! This spacious and upgr...
Listed by SAND DOLLAR REALTY GROUP INC
$535,000
Single Family Home
240 ORANGE TERRACE DR, Winter Park, FL 32789
DON'T MISS OUT! <br>Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath ...
Listed by A+ REALTY PROFESSIONALS, INC
$514,900
Single Family Home
8136 LAZY BEAR LN, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to Enclave at Aloma — a gated community quietly nestled in a con...
Listed by FANNIE HILLMAN & ASSOCIATES
$980,000
Single Family Home
208 BREWER AVE, Winter Park, FL 32789
SELLERS ARE OFFERING A $5,000 CREDIT TO A BUYER FOR AN ACCEPTED CONTRACT BY 09/30/25! Welcome to this beautifully update...
Listed by COMPASS FLORIDA LLC
$599,500
Townhouse
1250 FORMOSA AVE, Winter Park, FL 32789
Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after...
Listed by RE/MAX TOWN & COUNTRY REALTY
$995,000
Townhouse
512 CLARENDON AVE, Winter Park, FL 32789
Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins Colle...
Listed by COMPASS FLORIDA LLC