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60 Properties Available
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$775,000
Townhouse
1429 INDIANA AVE, Winter Park, FL 32789
Like new and totally turn-key! Built by award-winning Winter Park Custom Homes, coastal modern residence offers thoughtf...
Listed by KELLY PRICE & COMPANY LLC
$3,180,000
Single Family Home
731 WILLIAMS DR, Winter Park, FL 32789
Introducing a stunning brand-new custom home by Butler Ridge Development, located in the highly desirable Park Grove nei...
Listed by FANNIE HILLMAN & ASSOCIATES
$475,000
Single Family Home
2886 CAREW AVE, Winter Park, FL 32789
This charming 4 bedroom home is available now! With lots of open space, a cozy fireplace, and a walk-in closet in the pr...
Listed by OLDE TOWN BROKERS INC
$2,750
Single Family Home
1931 OGLESBY AVE, Winter Park, FL 32789
Location, Location, Location... Offered here is an Amazing Rental with many potential options of usage... 4 Bedrooms and...
Listed by KEEN REALTY GROUP, INC.
$1,799,000
Single Family Home
2402.5 TEMPLE DR, Winter Park, FL 32789
Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 1...
Listed by OLDE TOWN BROKERS INC
$1,385,000
Single Family Home
2105 FOSGATE DR, Winter Park, FL 32789
This home is the perfect blend of resort luxury and farmhouse charm, with high-end finishes and features that cater to b...
Listed by LPT REALTY, LLC
$1,200,000
Single Family Home
309 PARK NORTH CT, Winter Park, FL 32789
Under contract-accepting backup offers. Endless Potential in the Heart of Park North! <br>Just steps from the charm and ...
Listed by FANNIE HILLMAN & ASSOCIATES
$2,175,000
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
$2,950,000
Single Family Home
1020 MAYFIELD AVE, Winter Park, FL 32789
Exquisite, Luxury Listing in the Heart of Winter Park! Stunning, single-story residence, customized and remodeled by Phi...
Listed by KELLY PRICE & COMPANY LLC
$689,000
Condo
640 KILLARNEY BAY CT #4, Winter Park, FL 32789
Tucked away on the tranquil shores of Lake Killarney, this impeccably remodeled two-story residence offers a rare opport...
Listed by COMPASS FLORIDA LLC
$137,500
Condo
1695 LEE RD #E214, Winter Park, FL 32789
Don't miss out on this wonderful 2/1 featuring an awesome balcony overlooking a peaceful green space with a tranquil pon...
Listed by RE/MAX ASSURED
$259,000
Condo
1250 S DENNING DR #111, Winter Park, FL 32789
LOCATION LOCATION!! Now is your chance to own this STUNNING NEWLY RENOVATED 2 bed / 2 full bath FIRST FLOOR condo in the...
Listed by EXP REALTY LLC
$349,000
Single Family Home
156 OAK GROVE RD, Winter Park, FL 32789
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence in the highly desirable Winter Park Oaks commu...
Listed by EVERLANE REALTY LLC
$539,000
Single Family Home
2381 ROXBURY RD, Winter Park, FL 32789
WINTER PARK-Outstanding Renovations! Beautiful 3 Bedrooms 2 Baths! Open concept floor plan, single story with a lot of n...
Listed by KELLER WILLIAMS HERITAGE REALTY
$5,995
Single Family Home
433 CAROLINA AVE, Winter Park, FL 32789
A stunning two-story house with five bedrooms is now available. The house has ceramic tittle except for the bedrooms whi...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$995,000
Single Family Home
250 CORTLAND AVE, Winter Park, FL 32789
Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of th...
Listed by EXP REALTY LLC
$1,495
Single Family Home
1714 MILLER AVE, Winter Park, FL 32789
Welcome to this charming duplex nestled in the heart of Winter Park. This 2-bedroom one bathroom with a one car carport ...
Listed by RE/MAX 200 REALTY
$1,495
Single Family Home
1716 MILLER AVE, Winter Park, FL 32789
Welcome to this charming duplex nestled in the heart of Winter Park. This 2-bedroom one bathroom with a one car carport ...
Listed by RE/MAX 200 REALTY
$1,195,000
Single Family Home
1213 RICHMOND RD, Winter Park, FL 32789
An extraordinary and rare opportunity awaits in the highly sought-after Virginia Heights neighborhood, just a short stro...
Listed by KELLY PRICE & COMPANY LLC
$159,900
Condo
1695 LEE RD #E103, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Price Reduced!! Waterfall Cove, where urban convenience meets tranquil l...
Listed by ROBERT SLACK LLC
$665,000
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
$1,995
Condo
1055 S KENTUCKY AVE #4, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dini...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$1,995
Condo
1055 S KENTUCKY AVE #1, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$1,995
Condo
1055 S KENTUCKY AVE #2, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV