236 Properties Available
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$2,119,000
Single Family Home
785 N PHELPS AVE, Winter Park, FL 32789
Under Construction. Completion September 2025, Nestled in the heart of Winter Park, this luxurious custom-built home sea...
Listed by COMPASS FLORIDA LLC
$1,300,000
Single Family Home
1400 S PENNSYLVANIA AVE, Winter Park, FL 32789
Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. <br>You will...
Listed by JACK KELLER INC
$599,000
Single Family Home
1875 STAUNTON AVE, Winter Park, FL 32789
WELCOME HOME! LOCATION LOCATION LOCATION!!! Built in 2017, this 4 bedroom, 2 bathroom home is exactly what you are looki...
Listed by THE AGENCY ORLANDO
$144,900
Condo
1695 LEE RD #A209, Winter Park, FL 32789
Beautiful 1-Bedroom Condo in prime location! This Waterfall Cove at Winter Park condo presents, a spacious open layout a...
Listed by FUSILIER REALTY GROUP
$665,000
Single Family Home
1792 KILLARNEY DR, Winter Park, FL 32789
Welcome to this incredible and rare opportunity to own a Winter Park home with deeded private lake access to Lake Killar...
Listed by THE AGENCY ORLANDO
$849,900
Single Family Home
675 OVERSPIN DR, Winter Park, FL 32789
This well-appointed house features approximately 2,962 square feet of living space with four bedrooms and three and a ha...
Listed by COLDWELL BANKER RESIDENTIAL RE
$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
$10,900,000
Single Family Home
1120 PRESERVE POINT DR, Winter Park, FL 32789
Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean Estate i...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,265,000
Single Family Home
1611 WALNUT AVE, Winter Park, FL 32789
PRICE REDUCED TO $1,265,000 <br>Prime Location! <br>Step into the charm of Old Winter Park in this uniquely designed one...
Listed by COLDWELL BANKER RESIDENTIAL RE
$140,000
Condo
1695 LEE RD #B211, Winter Park, FL 32789
Fantastic 2 bedroom, 1 bathroom unit in the centrally located Waterfall Cove community in Winter Park, close to all of t...
Listed by RE/MAX ASSURED
$1,450
Single Family Home
1512 INDIANA AVE #B, Winter Park, FL 32789
Spacious ONE BEDROOM , one 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
$2,150
Condo
151 N ORLANDO AVE #207, Winter Park, FL 32789
Welcome to this beautifully renovated 2-bedroom, 1-bathroom second-floor condo on picturesque Lake Killarney. This move-...
Listed by PALMANO GROUP RE BROKERAGE LLC
$1,450
Single Family Home
1512 INDIANA AVE #A, Winter Park, FL 32789
Spacious ONE BEDROOM , one 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
$375,000
Single Family Home
2827 EUSTON RD, Winter Park, FL 32789
Welcome to 2827 Euston Rd, a beautifully updated home in the highly desirable Winter Park area with the added bonus of n...
Listed by REGENCY REAL ESTATE LLC
$235,000
Condo
1500 GAY RD #7A, Winter Park, FL 32789
Seller to replace windows or give a credit to buyer at closing!!! Discover unparalleled comfort in this stunning 2-bed, ...
Listed by PRISTINE FLORIDA PROPERTIES LLC
$1,897,000
Single Family Home
2260 MULBRY DR, Winter Park, FL 32789
Pre-Construction. To be built. Price Improvement! Your Dream Home Is Ready To Be Built!! Pre-Construction Opportunity! B...
Listed by KELLER WILLIAMS WINTER PARK
$8,799,000
Single Family Home
2661 VIA TUSCANY, Winter Park, FL 32789
CALLING HIGHEST AND BEST BY 4/30/2025!! <br> <br>Introducing a Unique, Stunning Modern Home <br> <br>A groundbreaking a...
Listed by PV LUXURY GROUP PA
$189,900
Condo
1250 S DENNING DR #122, Winter Park, FL 32789
One or more photo(s) has been virtually staged. **MAJOR PRICE DROP** FANTASTIC OPPORTUNITY** <br>Discover the perfect b...
Listed by ORLANDO HOME DEALER LLC
$189,900
Condo
1695 LEE RD #B216, Winter Park, FL 32789
Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaura...
Listed by RE/MAX ASSURED
$2,799,000
Single Family Home
2550 VENETIAN WAY, Winter Park, FL 32789
"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME H...
Listed by COMPASS FLORIDA LLC
$1,599,999
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
$1,600
Condo
1695 LEE RD #C103, Winter Park, FL 32789
Charming condo for Lease! location , Location , location ! This 2-bedroom, 1-bathroom apartment offers an open layout wi...
Listed by EMPIRE NETWORK REALTY