50 Properties Available
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$285,000
Condo
1920 WOODCREST DR #15, Winter Park, FL 32792
Gorgeous, fully renovated 2-bedroom / 2-bathroom condominium nestled in the heart of Winter Park along a beautiful and q...
Listed by COLDWELL BANKER RESIDENTIAL RE
$689,900
Single Family Home
3759 KINSLEY PL, Winter Park, FL 32792
EXPECT TO BE IMPRESSED! Tucked away in a quaint and quiet Winter Park neighborhood, this beautifully maintained two-stor...
Listed by COMPASS FLORIDA LLC
$765,000
Single Family Home
620 DARCEY DR, Winter Park, FL 32792
New roof scheduled for replacement at end of July 2025. Charming brick Winter Park home in the desirable Brookshire Heig...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$525,000
Single Family Home
2844 SCARLET RD, Winter Park, FL 32792
Welcome to this stunning mid-century modern beauty where timeless design meets thoughtful, contemporary updates. Nestled...
Listed by KELLER WILLIAMS WINTER PARK
$1,349,000
Single Family Home
2922 REEF KNOT PL, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Stunning Lakefront Living in an Exclusive Gated Community! Welcome to th...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$297,999
Townhouse
2376 DOMINICA RUN, Winter Park, FL 32792
Welcome to this beautifully updated townhouse located in the heart of desirable Winter Park! Step inside to find a brigh...
Listed by MARK SPAIN REAL ESTATE
$1,100,000
Single Family Home
2880 OLD CASTLE DR, Winter Park, FL 32792
Under contract-accepting backup offers. Welcome to this beautifully designed executive pool home with private in-law qua...
Listed by CORCORAN PREMIER REALTY
$241,900
Condo
200 SAINT ANDREWS BLVD #2306, Winter Park, FL 32792
Excellent opportunity in a prime location in Central Florida. This two-bedroom, two-full-bath corner unit is in the Four...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$509,000
Single Family Home
7584 LODGE POLE TRL, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Beautiful remodeled pool home. Luxury vinyl plank flooring throughout t...
Listed by SAND DOLLAR REALTY GROUP INC
$350,000
Single Family Home
5144 ORANGE AVE, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome Home!! NEW ROOF, UPDATED KITCHEN, SEMINOLE COUNTY SCHOOLS. RV Ca...
Listed by WEMERT GROUP REALTY LLC
$499,999
Single Family Home
7602 LODGE POLE TRL, Winter Park, FL 32792
Nestled in desirable Arrowhead Cove, this meticulously maintained 3-bedroom, 2.5-bath home represents the pinnacle of Wi...
Listed by KELLER WILLIAMS CLASSIC
$1,747
Townhouse
Winter Park, FL 32792
Winter Park 2 Bedroom Upgraded Condo <br>This unit is tiled throughout with Granite counter tops No carpet to worry abou...
Listed by THE REALTY FACTOR INC
$735,000
Single Family Home
346 ELKHORN CT, Winter Park, FL 32792
Welcome to your next chapter in Winter Park Pines, tucked within the most sought-after school district in all of Orlando...
Listed by 407 PROPERTIES
$2,850
Single Family Home
3300 BENNINGTON CT, Winter Park, FL 32792
Winter Park Rental Home in Bennington Estates. Home offers 4 Bedrooms, 2 Baths, Split plan, Large Eat-in Kitchen w/Isla...
Listed by RE/MAX TOWN & COUNTRY REALTY
$1,499
Condo
1000 S SEMORAN BLVD #703, Winter Park, FL 32792
Spacious one-bedroom condominium in Golfside Villas! This move in ready first-floor unit includes a large living room, D...
Listed by CENTURY 21 CARIOTI
$4,000
Single Family Home
1289 HEAVENLY CV, Winter Park, FL 32792
Welcome to this move in ready 4-bedroom, 3-bath, 3-car garage pool home located in the exclusive gated community of Eden...
Listed by COLDWELL BANKER RESIDENTIAL RE
$670,777
Single Family Home
3115 HEARTLEAF PL, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Park, FL! This stunning 4-bedroom, ...
Listed by EXP REALTY LLC
$275,000
Townhouse
2318 INAGUA WAY, Winter Park, FL 32792
Discover One of Winter Park's Best Kept Secrets Windward Square! <br> <br>Welcome home to this completely renovated 2-be...
Listed by REAL BROKER, LLC
$2,699
Townhouse
2461 FIRSTLIGHT WAY, Winter Park, FL 32792
GREAT LOCATION!! Come and check out one of Winter Park's newest neighborhoods, Hawks Crest! This stunning townhome has ...
Listed by 407 PROPERTIES
$658,900
Single Family Home
3110 HEARTLEAF PL, Winter Park, FL 32792
Beautiful pool home with an open great room plan with high vaulted ceilings and master on the first floor situated on on...
Listed by RE/MAX PRIME PROPERTIES
$1,850
Townhouse
3019 CASSELWOOD ST, Winter Park, FL 32792
ATTENTION GOOD RENTERS!! COME TO SHOW THIS WONDERFUL OPORTUNITY FOR RENT THIS WONDERFUL TOWNHOUSE IN A REALLY GOOD LOCAT...
Listed by ORLANDO KEY REALTY LLC
$450,000
Single Family Home
2151 CONIFER AVE, Winter Park, FL 32792
Under contract-accepting backup offers. This POOL home is amazing in every way and is truly a must see! Original Owner w...
Listed by KORR REALTY CORP
$499,999
Single Family Home
1924 SUMMERFIELD RD, Winter Park, FL 32792
**This property qualifies for a closing cost credit up to $7,700 through the Seller's preferred lender.** Welcome to a l...
Listed by KELLER WILLIAMS REALTY AT THE PARKS
$375,000
Single Family Home
3430 ARBUTUS LN, Winter Park, FL 32792
Charming Winter Park Pool Home with Mother-In-Law Suite. Welcome to your own slice of paradise in the heart of Winter Pa...
Listed by URBAN NEST CLUB INC