- Register
- Sign In
457 Properties Available In Winter Park
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$347,500
Single Family Home
1605 PURITAN AVE, Winter Park, FL 32792
Charming Winter Park block home featuring 3 bedrooms, 2 bathrooms, and a versatile enclosed Florida room—perfect for a h...
Listed by Denise San Miguel REALTY LYNK INC
$249,900
Townhouse
7470 CANFORD CT #23, Winter Park, FL 32792
Beautifully updated three bedroom two and a half bath townhome in the heart of Winter Park with one thousand five hundre...
Listed by Sam Nguyen FLORIDA REALTY INVESTMENTS
$1,195,000
Single Family Home
1092 WADING WATERS CIR, Winter Park, FL 32792
Experience resort-style living every day in this stunning Meritage Homes masterpiece, perfectly situated on a premium wa...
Listed by Tara Haefner KELLER WILLIAMS HERITAGE REALTY
$785,000
Single Family Home
2074 LAURELWOOD WAY, Winter Park, FL 32792
Discover your next home in the heart of Winter Park! Welcome to 2074 Laurelwood Way, a stunning one-story Pomelo model b...
Listed by Janki Thakkar EXP REALTY LLC
$460,000
Single Family Home
2218 KING RICHARDS CT, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome home to 2218 King Richards Court — a beautifully updated pool ho...
Listed by Steve Montgomery EXP REALTY LLC
$2,295,000
Single Family Home
1885 TEMPLE DR, Winter Park, FL 32789
Update! ALL NEW Black Steel doors installed 11/2025 and windows with low e-dual pane glass to be installed ($150k value!...
Listed by Jennifer Sloan COMPASS FLORIDA LLC
$369,000
Single Family Home
5110 N WOODCREST DR, Winter Park, FL 32792
SELLER MOTIVATED! Discover the perfect blend of comfort and convenience in this beautifully remodeled 3-bedroom, 2-bath ...
Listed by Danielle Richardson LPT REALTY, LLC
$1,499,000
Single Family Home
102 BELL PL, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction ...
Listed by Freddie Crespo INVESTOR'S REAL ESTATE LLC
$415,000
Single Family Home
1872 BISCAYNE DR, Winter Park, FL 32789
Back on the market due to seller changing real estate companies - not due to financing or inspections. Don't miss this r...
Listed by Shirley Jones COLDWELL BANKER RESIDENTIAL RE
$2,900,000
Single Family Home
1401 GREEN COVE RD, Winter Park, FL 32789
Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park's ...
Listed by Adriana Oyarce ANCHOR REAL ESTATE
$1,375,000
Single Family Home
2015 SUMMERFIELD RD, Winter Park, FL 32792
Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake B...
Listed by Christina Fata REAL BROKER, LLC
$3,895,000
Single Family Home
1751 GLENCOE RD, Winter Park, FL 32789
Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed Davila Homes masterpiece redefine...
Listed by Julie Christensen COMPASS FLORIDA LLC
$745,000
Single Family Home
1324 INDIANA AVE, Winter Park, FL 32789
Charming two story bungalow built in 1935. Timeless character meets modern comfort in this beautifully maintained four b...
Listed by Ivey Geisler KELLER WILLIAMS REALTY AT THE PARKS
$2,598,000
Single Family Home
1661 PALM AVENUE, Winter Park, FL 32789
Introducing a stunning new custom home by Ellsworth Gallimore and Butler Ridge Development, ideally situated in a prime ...
Listed by Nancy Bagby FANNIE HILLMAN & ASSOCIATES
$3,795,000
Single Family Home
516 HENKEL CIR, Winter Park, FL 32789
This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of th...
Listed by Morgan Seefried KELLER WILLIAMS WINTER PARK
$1,560,000
Single Family Home
1460 VIA SANGRO PL, Winter Park, FL 32792
Waterfront dream home in the exclusive, gated community of Lakeside Estates on beautiful Garden Lake. This exquisite 7-b...
Listed by Jennifer Sloan COMPASS FLORIDA LLC
$499,900
Single Family Home
2381 ROXBURY RD, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Live the Winter Park dream in this freshly updated 3-bedroom, 2-bath hom...
Listed by Alex Vastardis COLDWELL BANKER REALTY
$1,675,000
Single Family Home
132 BURKS CIR, Winter Park, FL 32789
Experience refined living in this completely remodeled single story residence located in the heart of Winter Park. Enjoy...
Listed by Ivey Geisler KELLER WILLIAMS REALTY AT THE PARKS
$650,000
Single Family Home
428 SELKIRK DR, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Income-Producing Opportunity! Welcome to this versatile Winter Park POOL...
Listed by Sheri Malin REDFIN CORPORATION
$499,000
Single Family Home
1422 TIERRA CIR, Winter Park, FL 32792
PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Available, making it an excellent op...
Listed by Jennifer Conrado CHARLES RUTENBERG REALTY ORLANDO
$235,000
Condo
700 MELROSE AVE #J 23, Winter Park, FL 32789
Beautiful 1-Bedroom Condo in the Heart of Winter Park Located on the second floor close to ELEVATORS. Please click on vi...
Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
$1,999,000
Single Family Home
1540 PALM AVE, Winter Park, FL 32789
Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park's most desirable neigh...
Listed by John McDade FANNIE HILLMAN & ASSOCIATES
$1,598,000
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 Pilar Ulloa REAL ESTATE FIRM OF ORLANDO
$560,000
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 Jill Healey KELLER WILLIAMS WINTER PARK