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494 Properties Available In Winter Park
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$1,585,000
Single Family Home
1450 GLENCOE RD, Winter Park, FL 32789
Experience the charm and comfort of this one-story, Key West-style pool home, nestled on a brick-lined street and canopi...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,349,500
Single Family Home
1371 LYNDALE BLVD, Winter Park, FL 32789
One or more photo(s) has been virtually staged. As you enter this renovated 4-bedroom, 2.5-bathroom home within the city...
Listed by ALIGN REAL ESTATE LLC
$365,000
Single Family Home
2006 PONDEROSA AVE, Winter Park, FL 32792
Pure Potential in Winter Park's Eastbrook Community! Renovate or move-in, this is a great opportunity for an investor or...
Listed by KELLY PRICE & COMPANY LLC
$500,000
Single Family Home
7602 LODGE POLE TRL, Winter Park, FL 32792
Nestled in desirable Arrowhead Cove, this meticulously maintained 3-bedroom, 2.5-bath home represents the pinnacle of Wi...
Listed by KELLER WILLIAMS CLASSIC
$775,000
Single Family Home
620 DARCEY DR, Winter Park, FL 32792
New roof scheduled for replacement at end of July 2025. Charming brick Winter Park home in the desirable Brookshire Heig...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$865,000
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
$649,900
Single Family Home
1926 NATALEN RD, Winter Park, FL 32792
*** MUST SEE WINTER PARK POOL HOME *** <br>Explore the virtual tours to fully appreciate the beauty of this completely r...
Listed by EXP REALTY LLC
$549,000
Single Family Home
2244 BROOKSHIRE AVE, Winter Park, FL 32792
Welcome to this delightful 3-bedroom, 2-bathroom single-family home located in the highly sought-after Brookshire Height...
Listed by EXP REALTY LLC
$575,000
Single Family Home
1339 ORCHID AVE, Winter Park, FL 32789
A rare find in Winter Park: A charming Bungalow with 3-Car Garage (24x36) and detached finished Shed (10x14) for office ...
Listed by ABIDE REALTY
$2,849,000
Single Family Home
2652 LAKE HOWELL LN, Winter Park, FL 32792
This approximately 4200 square foot home is situated on a 1.68-acre gorgeous lakefront lot in the desirable Winter Park...
Listed by COLDWELL BANKER REALTY
$459,000
Single Family Home
3304 BENNINGTON CT, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome Home! This immaculate 3-bedroom, 2-bathroom single family home i...
Listed by DAHLIA REALTY GROUP
$1,999,500
Single Family Home
1840 BRYAN AVE, Winter Park, FL 32789
This custom 2014 built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet clo...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$875,000
Single Family Home
1090 WILDMEADOW RUN, Winter Park, FL 32792
One or more photo(s) has been virtually staged. This luxurious Modern Style home delivers the pinnacle lifestyle, in eve...
Listed by BHHS FLORIDA REALTY
$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
$1,195,000
Single Family Home
1611 CHESTNUT AVE, Winter Park, FL 32789
MOTIVATED SELLER AND VERY EASY SHOW! 1500 SQ FEET BRAND NEW LIVING SPACE HAD BEEN ADDED ON. NEW ROOF, TWO NEW AC SYSTEMS...
Listed by PARK AVENUE REALTY LLC
$2,389,000
Single Family Home
2412 CHANTILLY AVE, Winter Park, FL 32789
An architectural tour de force in the heart of Winter Park. Designed by a premier builder of boutique homes and crafted ...
Listed by COMPASS FLORIDA LLC
$3,150,000
Single Family Home
575 PALMER AVE, Winter Park, FL 32789
Step into elevated Winter Park living with this exceptional Mediterranean-inspired estate. Built in 2020, every inch of ...
Listed by DEVLIN INVESTORS & ASSOCIATES
$750,000
Single Family Home
2478 WHITEHALL CIR, Winter Park, FL 32792
Expect to be impressed with this updated 3BR home in one of Winter Park's well- <br>established neighborhoods. It starts...
Listed by LPT REALTY, LLC
$450,000
Single Family Home
1871 STAUNTON AVE, Winter Park, FL 32789
Charming Bungalow on Double Lot Near Lake Killarney! Welcome to this delightful 3-bedroom, 2-bathroom bungalow nestled ...
Listed by WATSON REALTY CORP.
$2,850
Single Family Home
1057 MINNESOTA AVE, Winter Park, FL 32789
RARE FIND available Fully or Partially Furnished. This authentic 1920's bungalow style home sits in a picturesque locati...
Listed by SHORES REAL ESTATE
$1,390,000
Single Family Home
501 LAKEVIEW AVE, Winter Park, FL 32789
Under Construction. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with cris...
Listed by COLDWELL BANKER RESIDENTIAL RE
$1,390,000
Single Family Home
525 LAKEVIEW AVE, Winter Park, FL 32789
Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic ...
Listed by COLDWELL BANKER RESIDENTIAL RE
$370,000
Condo
150 KILLARNEY BAY CT #5, Winter Park, FL 32789
Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and...
Listed by COMPASS FLORIDA LLC
$339,500
Single Family Home
3103 ASH PARK LOOP, Winter Park, FL 32792
Welcome to Hyde Park, nestled off Howell Branch Road in Seminole County. First time offered. Wonderful two bedroom, tw...
Listed by PREMIER SOTHEBY'S INTL. REALTY