31 Properties for Sale
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$840,000
Condo
100 S INTERLACHEN AVE #204D, Winter Park, FL 32789
Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned bet...
Listed by COLDWELL BANKER RESIDENTIAL RE
$1,899,900
Single Family Home
1521 CHESTNUT AVE, Winter Park, FL 32789
Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, built in 2023, located in one of W...
Listed by COMPASS FLORIDA LLC
$1,499,000
Single Family Home
1429 CHAPMAN CIR, Winter Park, FL 32789
Exceptional Phil Kean-designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophistica...
Listed by CORCORAN PREMIER REALTY
$399,000
Condo
311 E MORSE BLVD #7-5, Winter Park, FL 32789
Major Price Improvement & Motivated Seller! Here is your rare opportunity to own a studio apartment in Whispering Waters...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$360,000
Single Family Home
1921 DARTMOUTH AVE, Winter Park, FL 32789
Charming, Fully Renovated Bungalow in the Heart of Winter Park! Welcome to this beautifully upgraded bungalow that make...
Listed by THOMAS LYNNE REALTY GROUP LLC
$410,000
Condo
240 KILLARNEY BAY CT #4, Winter Park, FL 32789
Welcome to Killarney Bay—Winter Park's best-kept secret for tranquil lakeside living, and just steps from the city's fin...
Listed by KELLER WILLIAMS WINTER PARK
$1,850,000
Single Family Home
1355 HIBISCUS AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-f...
Listed by PALMANO GROUP RE BROKERAGE LLC
$1,750,000
Single Family Home
446 ALBERTA DR, Winter Park, FL 32789
Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits ...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$3,190,000
Single Family Home
1820 ENGLEWOOD RD, Winter Park, FL 32789
Award-winning Phil Kean design on a prominent corner lot in the heart of Winter Park, just minutes from Baldwin Park, Pa...
Listed by KELLER WILLIAMS ADVANTAGE III
$1,095,000
Single Family Home
2607 LAFAYETTE AVE, Winter Park, FL 32789
Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park's most desirable neig...
Listed by FORTUNE INTERNATIONAL REALTY
$3,975,000
Single Family Home
1581 FOREST AVE, Winter Park, FL 32789
An Exquisite “Hollywood Regency” style residence showcasing a meticulous architectural reconstruction by Master Custom ...
Listed by BHHS FLORIDA REALTY
$332,000
Condo
184 SANDLEWOOD TRL #2, Winter Park, FL 32789
Welcome to Your Turnkey Retreat in Winter Park! <br> <br>Nestled just minutes from the charming boutiques and award-winn...
Listed by EXP REALTY LLC
$1,514,950
Single Family Home
952 MOSS LN, Winter Park, FL 32789
Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and...
Listed by THE SHOP REAL ESTATE CO.
$1,495,000
Single Family Home
1741 PALMER AVE, Winter Park, FL 32789
Welcome home to this one-of-a-kind, single-story Tuscan-style retreat nestled on an oversized lot in the heart of highly...
Listed by CENTRAL FLORIDA PRIME REAL ESTATE LLC
$1,595,000
Single Family Home
1831 MIZELL AVE, Winter Park, FL 32789
Stunning contemporary home in Winter Park is close to Park Avenue and all of the wonderful restaurants, shops and the hi...
Listed by EXP REALTY LLC
$1,200,000
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
$2,125,000
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
$3,595,000
Single Family Home
2171 FORREST RD, Winter Park, FL 32789
On one of Winter Park's most scenic brick-lined streets, this exceptional two-story residence commands attention on a sp...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$659,000
Condo
640 KILLARNEY BAY CT #4, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake Killarney, this impeccably re...
Listed by COMPASS FLORIDA LLC
$970,000
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
$1,399,000
Single Family Home
1600 BARCELONA WAY, Winter Park, FL 32789
Under contract-accepting backup offers. Back on the market at no fault of the seller. Step into the charm of old Florida...
Listed by LPT REALTY, LLC
$439,900
Condo
535 N INTERLACHEN AVE #107, Winter Park, FL 32789
Under contract-accepting backup offers. Location, Location, Location - downtown Winter Park condo for under $500K! This ...
Listed by FANNIE HILLMAN & ASSOCIATES
$6,200,000
Single Family Home
1400 ALABAMA DR, Winter Park, FL 32789
Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland, the largest of t...
Listed by THE AGENCY ORLANDO
$149,900
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