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222 Properties Available
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$625,000
Condo
777 S DENNING DR #B, Winter Park, FL 32789
Under contract-accepting backup offers. This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic...
Listed by KELLER WILLIAMS WINTER PARK
$1,685
Single Family Home
657 MINNESOTA AVE, Winter Park, FL 32789
DUPLEX - FANTASTIC WINTER PARK LOCATION. 2 bedroom, 1 bath, with carport on driveway.. PRIVATE FENCED BACKYARD!! Terrazz...
Listed by A+ HOME RENTALS LLC
$1,500,000
Single Family Home
1741 PINE AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Nestled in the heart of Winter Park, this stunning 4-bedroom, 3-bathroom pool ho...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,750
Condo
1250 S DENNING DR #130, Winter Park, FL 32789
Great Location & Available 05/15/25! Beautiful Condo for Rent at the Mead Garden in Winter Park. Spacious 2 Bedroom and ...
Listed by FLORIDA TOP REALTY
$145,000
Condo
1695 LEE RD #E205, Winter Park, FL 32789
SPECIAL FINANCING AVAILABLE! First Horizon Home Start w/ Diversity Grant available for this home while funds last. Thi...
Listed by KELLER WILLIAMS HERITAGE REALTY
$1,575,000
Condo
690 OSCEOLA AVE #604, Winter Park, FL 32789
Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder's unit with panoramic views of Lake Virginia from almos...
Listed by COLDWELL BANKER RESIDENTIAL RE
$4,395,000
Single Family Home
229 ALEXANDER PL, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Discover a stunning blend of modern luxury and award-winning design in t...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$4,600,000
Single Family Home
2118 LAKE DR, Winter Park, FL 32789
"The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a p...
Listed by COMPASS FLORIDA LLC
$409,900
Single Family Home
1975 STAUNTON AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. An awesome home for young professionals or family or great rental for an...
Listed by ABSOLUTE REALTY GROUP, LLC
$1,475,000
Single Family Home
1750 WINCHESTER DR, Winter Park, FL 32789
Welcome to this masterfully renovated Winter Park residence, where modern luxury meets timeless comfort in coveted Timbe...
Listed by FANNIE HILLMAN & ASSOCIATES
$369,000
Condo
151 N ORLANDO AVE #229, Winter Park, FL 32789
LOCATION, LOCATION, LOCATION with partial Lake View! <br> <br>Tenant secured for 6.1.25 through 4.30.26 at $1,799 per m...
Listed by EXP REALTY LLC
$1,999
Single Family Home
1101 S PENNSYLVANIA AVE, Winter Park, FL 32789
Charming duplex for rent near the “College Quarter” in Winter Park. 2 bedrooms and 1 bath plus laundry room with washer...
Listed by AUTHENTIC REAL ESTATE TEAM
$169,000
Condo
1695 LEE RD #E103, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This char...
Listed by ROBERT SLACK LLC
$2,500,000
Single Family Home
450 LAKEWOOD DR, Winter Park, FL 32789
Custom estate 5 bedroom pool home now available that exudes meticulous detail, luxury and designed for entertaining. Th...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$725,000
Condo
535 N INTERLACHEN AVE #106, Winter Park, FL 32789
Rare opportunity to own a first floor unit with soaring 9 foot ceilings only steps away from the prestegious Park Avenue...
Listed by KELLER WILLIAMS WINTER PARK
$659,000
Single Family Home
2812 MULFORD AVE, Winter Park, FL 32789
Welcome to 2812 Mulford Avenue. This updated 3 bedroom and 2 bath home is located perfectly in Winter Park. Walking dist...
Listed by SYNCHRONICITY REAL ESTATE SOLUTIONS
$5,200,000
Single Family Home
1660 PALMER AVE, Winter Park, FL 32789
Experience refined luxury in this newly constructed 2024 Hamptons-style residence, a seamless blend of elegance and mode...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$2,379,900
Single Family Home
301 RIPPLING LN, Winter Park, FL 32789
Nestled along the serene shores of Lake Killarney, one of Winter Park's best-kept secrets Lake Killarney is one of Winte...
Listed by XCLUSIVE HOMES LLC
$849,000
Single Family Home
625 WORTHINGTON DR, Winter Park, FL 32789
Under contract-accepting backup offers. Completely remodeled, coastal-inspired home is located in the highly sought-afte...
Listed by KELLY PRICE & COMPANY LLC
$1,275,000
Multi-Family
726 and 720 N PENNSYLVANIA AVE, Winter Park, FL 32789
Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibility and investment potential. W...
Listed by RE/MAX TOWN & COUNTRY REALTY
$1,275,000
Single Family Home
726/720 N PENNSYLVANIA AVE, Winter Park, FL 32789
Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you're looking for...
Listed by RE/MAX TOWN & COUNTRY REALTY
$750,000
Single Family Home
726 N PENNSYLVANIA AVE, Winter Park, FL 32789
Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of modern elegance and prime location....
Listed by RE/MAX TOWN & COUNTRY REALTY
$550,000
Single Family Home
720 N PENNSYLVANIA AVE, Winter Park, FL 32789
Nestled in one of Winter Park's most sought-after locations, this 3-bedroom, 2-bathroom home seamlessly blends modern el...
Listed by RE/MAX TOWN & COUNTRY REALTY
$1,295,000
Single Family Home
1611 CHESTNUT AVE, Winter Park, FL 32789
Welcome to this stunning, fully renovated home in the heart of Winter Park. Located on Chestnut avenue beautifully rebui...
Listed by PARK AVENUE REALTY LLC