73 Properties Available
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$1,705
Condo
851 MILES AVE #8, Winter Park, FL 32789
UNBELIEVABLE PRICE DROP! This gorgeous 2 bedroom 1 bathroom condo is ready to go, and priced for you! This unit is a sec...
Listed by LPT REALTY, LLC
$1,250,000
Single Family Home
1450 CHESTNUT AVE, Winter Park, FL 32789
Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timeless Mediterranean home offers t...
Listed by KELLY PRICE & COMPANY LLC
$625,000
Single Family Home
720 W WEBSTER AVE, Winter Park, FL 32789
Discover the charm of Winter Park living in this beautifully maintained 1950s home, where convenience and comfort meet m...
Listed by THE AGENCY ORLANDO
$200,000
Condo
2500 LEE RD #219, Winter Park, FL 32789
Welcome to life on Lake Killarney, one of Winter Park's most sought-after lakefront communities! This charming 2-bedroom...
Listed by SUNDIAL REAL ESTATE LLC
$2,100
Condo
632 GAINES WAY, Winter Park, FL 32789
Just blocks from Park Avenue and Rollins College, this newly built fully furnished charming 1 bedroom, 1 bath apartment ...
Listed by WEMERT GROUP REALTY LLC
$3,295
Single Family Home
830 DOUGLAS AVE, Winter Park, FL 32789
Beautifully renovated home featuring a split floor plan & elegant woodgrain tile flooring throughout. The kitchen is fil...
Listed by PREMIER MANAGEMENT GROUP INC
$1,695
Condo
851 MILES AVE #21, Winter Park, FL 32789
Enjoy a quiet but beautiful space at Aragon Condominiums. This first-floor corner unit allows for privacy with only one ...
Listed by FLORIDA ONE REAL ESTATE LLC
$1,095,000
Single Family Home
215 SALVADOR SQUARE, Winter Park, FL 32789
Welcome home to this lovely four-bedroom, three-and-a-half-bath pool home in the gorgeous Sevilla neighborhood of Winter...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$630,000
Single Family Home
1740 ANZLE AVE, Winter Park, FL 32789
PROPERTY AS-IS - <br>DEMO AND NEW-BUILD PLANS APPROVED <br>*Property with all demo permits and build plans approved rea...
Listed by GOYAL & DECOSTER REALTY
$349,900
Condo
311 E MORSE BLVD #7-11, Winter Park, FL 32789
Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! <br>Welcome to Whispering Waters, a beautifully mai...
Listed by FANNIE HILLMAN & ASSOCIATES
$10,000
Single Family Home
1661 HILLCREST AVE, Winter Park, FL 32789
Owner open to 9+ month lease period. Luxurious Winter Park Retreat with Stunning Features! Welcome to 1661 Hillcrest Ave...
Listed by ROYALTY R E BOUTIQUE INC
$3,695
Single Family Home
1641 CHESTNUT AVE, Winter Park, FL 32789
Welcome to your new home nestled along Winter Park's coveted tree-lined Chestnut Avenue. This beautiful 3 bedroom, 3 bat...
Listed by REAL PROPERTY MANAGEMENT AND REALTY
$1,600
Condo
1250 S DENNING DR #232, Winter Park, FL 32789
Less than 1 mile from Rollins College and Park Ave in the highly desirable 32789 Winter Park zip code. This 2-Bedroom, 2...
Listed by RE/MAX DOWNTOWN
$2,329,000
Single Family Home
715 VIA BELLA, Winter Park, FL 32789
Tucked away on a quiet cul-de-sac lined with multi-million-dollar estates, this Winter Park residence offers an enviable...
Listed by COMPASS FLORIDA LLC
$2,760
Single Family Home
2843 RIDDLE DR, Winter Park, FL 32789
Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with fu...
Listed by MAIN STREET RENEWAL LLC
$1,549
Condo
1500 MICHIGAN AVE #B, Winter Park, FL 32789
This charming 2-bedroom, 1-bathroom apartment offers comfortable living space in a prime Winter Park location. Situated ...
Listed by 407 PROPERTIES
$2,550
Single Family Home
955 MINNESOTA AVE, Winter Park, FL 32789
Welcome to your new home at 955 Minnesota Avenue, nestled in the heart of charming Winter Park. This beautiful 3 bedroom...
Listed by REAL PROPERTY MANAGEMENT AND REALTY
$1,895
Townhouse
200 SANDLEWOOD TRL #4, Winter Park, FL 32789
ovely, light and airy home with newer appliances, fresh paint through out and newer laminate flooring upstairs. The kitc...
Listed by FANNIE HILLMAN & ASSOCIATES
$2,395
Townhouse
645 HUNTINGTON AVE #7, Winter Park, FL 32789
Live in style in this renovated 2-bedroom, 2.5-bath townhome located in the heart of Winter Park. The modern kitchen fea...
Listed by BELMONT REALTY
$6,995
Single Family Home
1205 MAYFIELD AVE, Winter Park, FL 32789
Great rental opportunity in Winter Park, FL! This two-story residence is located in the TEMPLE HEIGHTS neighborhood. Thi...
Listed by RE/MAX 200 REALTY
$2,000
Townhouse
235 SANDLEWOOD TRL, Winter Park, FL 32789
WINTER PARK: Sandlewood Creek Community - AVAILABLE NOW!! Welcome home to this great 3 bedroom, 3.5 bath, 3 story townho...
Listed by CFRP REALTY LLC
$3,500
Single Family Home
1288 MICHIGAN AVE, Winter Park, FL 32789
5 bedrooms, 3 bathrooms super close to Winter Park Village and conveniently located close to all Winter Park activities....
Listed by CQ ORLANDO REALTY INC
$545,000
Single Family Home
240 ORANGE TERRACE DR, Winter Park, FL 32789
JUST REDUCED, SELLER MOTIVATED! <br>Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-...
Listed by A+ REALTY PROFESSIONALS, INC
$2,900
Single Family Home
430 OLOLU DR, Winter Park, FL 32789
Interested in trying out the lake life in Winter Park? 430 Ololu is available FOR RENT beginning October 1st on Lake Kil...
Listed by MILLER GRANT AND COMPANY