20 Properties Available
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$1,050,000
Single Family Home
1610 CHESTNUT AVE, Winter Park, FL 32789
Nestled in the desirable Tree Streets of Winter Park, this stunning Mid-Century Modern residence offers timeless style, ...
Listed by THE AGENCY ORLANDO
$880,000
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
$3,975,000
Single Family Home
1742 TEMPLE DR, Winter Park, FL 32789
In one of Winter Park's desirable neighborhoods, this stunning four-bedroom, five-bath modern masterpiece with Control4 ...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$429,000
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
$3,895,000
Single Family Home
1820 GLENCOE RD, Winter Park, FL 32789
Welcome to your dream home—a masterfully designed, Dutch West Indies-inspired custom residence that blends timeless eleg...
Listed by CORCORAN PREMIER REALTY
$1,795,000
Single Family Home
1780 MIZELL AVE., Winter Park, FL 32789
Experience the height of modern luxury in this newly constructed home, masterfully designed by esteemed architect Gary H...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,595,000
Single Family Home
1733 HARMON AVE, Winter Park, FL 32789
Experience the charm and elegance of Winter Park living in this beautifully designed 5-bedroom, 4.5-bath home offering 3...
Listed by SOUTH REALTY, INC
$2,399,000
Single Family Home
922 N PENNSYLVANIA AVE, Winter Park, FL 32789
Experience timeless elegance and modern sophistication in this stunning 3 bedroom, 4 bath Mediterranean home, ideally si...
Listed by FANNIE HILLMAN & ASSOCIATES
$355,000
Condo
700 MELROSE AVE #C22, Winter Park, FL 32789
CLICK ON VIRTUAL TOUR to get an overview of the complex. <br>Discover a RARE opportunity to own a 3 BEDROOM 2.5 BATH uni...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,449,900
Single Family Home
1420 PALMER AVE, Winter Park, FL 32789
Luxurious Retreat in the Heart of Winter Park's Premier Neighborhood – Minutes from Park Ave! <br>Discover timeless eleg...
Listed by KELLER WILLIAMS WINTER PARK
$2,999,000
Single Family Home
1891 LAKE SPIER DR, Winter Park, FL 32789
Welcome to a rare opportunity to embrace the Winter Park lakefront lifestyle in this custom-built masterpiece that blend...
Listed by LPT REALTY, LLC
$1,888,000
Single Family Home
2407 LAFAYETTE AVE, Winter Park, FL 32789
Discover this exceptional custom-designed modern pool home, ideally situated on a quiet street in Winter Park. This spac...
Listed by FANNIE HILLMAN & ASSOCIATES
$2,900,000
Single Family Home
1401 GREEN COVE RD, Winter Park, FL 32789
This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open inte...
Listed by BUCKEYE REALTY 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
$1,699,000
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
$1,295,000
Single Family Home
1701 PALMER AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Charming Winter Park Pool Home – A Rare Opportunity! Nestled in the hear...
Listed by TRUST EQUITY GROUP LLC
$2,389,000
Single Family Home
2412 CHANTILLY AVE, Winter Park, FL 32789
Step into a realm of refined living—an architectural tour de force in the heart of Winter Park. Designed by a premier bo...
Listed by COMPASS FLORIDA LLC
$340,000
Condo
700 MELROSE AVE J 1 AVE #J1, Winter Park, FL 32789
PRICE IMPROVEMENT – Best buy in Winter Park..........Motivated Sellers! <br> CLICK ON VIRTUAL TOUR to get an overview...
Listed by FANNIE HILLMAN & ASSOCIATES
$949,000
Single Family Home
1840 BISCAYNE DR, Winter Park, FL 32789
One or more photo(s) has been virtually staged. A Rare Gem in Winter Park – New Construction by Konkol Custom Homes <br>...
Listed by COMPASS FLORIDA LLC
$2,750,000
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