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223 Properties Available In 32789
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$1,400,000
Single Family Home
2525 VENETIAN WAY, Winter Park, FL 32789
Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake Access <br>This meticulously renovated 3-bed, 2.5-...
Listed by KELLY PRICE & COMPANY LLC


$800,000
Single Family Home
441 N CAPEN AVE, Winter Park, FL 32789
Rare find in the heart of Historic West Winter Park - Newer 2017 solid built David Weekley home now available! This mode...
Listed by COLDWELL BANKER RESIDENTIAL RE


$235,000
Condo
1250 S DENNING DR #230, Winter Park, FL 32789
Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floo...
Listed by FANNIE HILLMAN & ASSOCIATES


$1,275,000
Single Family Home
309 PARK NORTH CT, Winter Park, FL 32789
Endless Potential in the Heart of Park North! <br>Just steps from the charm and energy of Winter Park's Park Avenue—wher...
Listed by FANNIE HILLMAN & ASSOCIATES


$1,025,000
Single Family Home
2923 COVE TRL, Winter Park, FL 32789
A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market ...
Listed by KELLER WILLIAMS ADVANTAGE III


$1,150,000
Single Family Home
795 W CANTON AVE, Winter Park, FL 32789
Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just a short stroll to iconic Park Avenue and...
Listed by WEICHERT REALTORS HALLMARK PROPERTIES


$1,299,000
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


$2,295,000
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


$3,195,000
Single Family Home
1020 MAYFIELD AVE, Winter Park, FL 32789
Exquisite, Luxury Listing in the Heart of Winter Park! Stunning, single-story residence, customized and remodeled by Phi...
Listed by KELLY PRICE & COMPANY LLC


$1,550,000
Single Family Home
1661 WOODLAND AVE, Winter Park, FL 32789
Fabulous Top-to-Bottom Renovation on Coveted Brick Street in Prime Winter Park Location! This exceptional 3-bedroom, 3.5...
Listed by FANNIE HILLMAN & ASSOCIATES


$285,000
Condo
151 N ORLANDO AVE #115, Winter Park, FL 32789
Fantastic 2 bed/ 1 bath - first floor condo in cool, mid-century building on Lake Killarney. This home is next to Trader...
Listed by FANNIE HILLMAN & ASSOCIATES


$1,385,000
Single Family Home
1370 ALBERTA DR, Winter Park, FL 32789
Discover luxurious lakeside living in prestigious Winter Park, where this extensively updated pool home offers the perfe...
Listed by FANNIE HILLMAN & ASSOCIATES


$2,795,000
Single Family Home
1630 LASBURY AVE, Winter Park, FL 32789
Nestled on a serene, brick-paved street in the heart of Winter Park, this elegant 5-bedroom, 3.2-bathroom pool home is s...
Listed by FANNIE HILLMAN & ASSOCIATES


$1,739,000
Single Family Home
279 RIPPLING LN, Winter Park, FL 32789
Discover serene lakefront living at its finest in this exquisite 4-bedroom 3 bath home at 279 Rippling Lane. Set against...
Listed by FANNIE HILLMAN & ASSOCIATES


$2,950,000
Single Family Home
1860 VIA CONTESSA, Winter Park, FL 32789
Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted ...
Listed by SIERRA REALTY GROUP LLC


$675,000
Single Family Home
1399 ALOMA AVE, Winter Park, FL 32789
Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on...
Listed by FLORIDA HOMES REALTY & MTG


$14,000
Single Family Home
909 SEMINOLE DR, Winter Park, FL 32789
FOR LEASE - STUNNING, COMPLETELY REMODELED BY SKOLFIELD HOMES GUEST HOUSE - IN THE GOLDEN TRIANGLE, WALKING DISTANCE TO...
Listed by KELLY PRICE & COMPANY LLC


$2,100,000
Single Family Home
2402.5 TEMPLE DR, Winter Park, FL 32789
Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 1...
Listed by OLDE TOWN BROKERS INC


$1,450,000
Single Family Home
2105 FOSGATE DR, Winter Park, FL 32789
This home is the perfect blend of resort luxury and farmhouse charm, with high-end finishes and features that cater to b...
Listed by LPT REALTY, LLC


$3,000
Single Family Home
663 CALLAHAN ST, Winter Park, FL 32789
Charming 3-Bedroom, 2-Bath Home for Rent in the Heart of Winter Park! <br>Ideally located just a short bike ride from Ha...
Listed by KELLER WILLIAMS REALTY AT THE PARKS


$8,000
Condo
311 E MORSE BLVD #2-3, Winter Park, FL 32789
Enjoy the perfect blend of modern comfort and timeless charm in this beautifully updated 2-bedroom, 2-bathroom condo for...
Listed by CHARLES RUTENBERG REALTY ORLANDO


$975,000
Single Family Home
1265 PARK POINTE LN, Winter Park, FL 32789
Welcome home to this beautifully upgraded gem nestled in the heart of Winter Park. This move-in-ready home sits on a qui...
Listed by KELLER WILLIAMS ADVANTAGE III


$3,500
Single Family Home
2530 FRANKLIN AVE, Winter Park, FL 32789
Come and enjoy the comfort and modern upgrades in this beautifully renovated and well-maintained 3-bedroom, 2-bath home,...
Listed by CHARLES RUTENBERG REALTY ORLANDO


$1,100,000
Single Family Home
913 MOSS LN, Winter Park, FL 32789
?913 Moss Ln, Winter Park, FL 32789 is a beautifully renovated 3-bedroom, 2-bathroom single-family home that seamlessly ...
Listed by FLAT FEE MLS REALTY
