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48 Properties Available
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$1,385,000
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
$829,000
Condo
1276 S PENNSYLVANIA AVE #12, Winter Park, FL 32789
Nestled within the tranquil confines of the Virginia Heights neighborhood lies a truly exceptional property that blends ...
Listed by COMPASS FLORIDA LLC
$1,695,000
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
$215,000
Condo
700 MELROSE AVE #K32, Winter Park, FL 32789
Discover Winter Park Gardens, an exclusive 55+ community nestled in the heart of historic Winter Park! Welcome to your p...
Listed by BALDWIN PARK REALTY LLC
$1,800
Condo
1695 LEE RD #E103, Winter Park, FL 32789
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where ur...
Listed by ROBERT SLACK LLC
$1,699,000
Single Family Home
2339 LAFAYETTE AVE, Winter Park, FL 32789
Under contract-accepting backup offers. This Beautiful Winter Park Home is located between the "Vias" and "Tree Streets"...
Listed by COLLADO REAL ESTATE
$369,000
Single Family Home
657 OVERSPIN DR, Winter Park, FL 32789
One or more photo(s) has been virtually staged. **Seller is motivated and encourages all serious offers—bring your buyer...
Listed by RE/MAX 200 REALTY
$1,495
Single Family Home
1434 MINNESOTA AVE, Winter Park, FL 32789
Remo2 bedroom and Mid Century Modern two bedroom and one bath home for rent in the heart of the industrial area of Winte...
Listed by COLDWELL BANKER RESIDENTIAL RE
$995,000
Single Family Home
1821 WINDSOR DR, Winter Park, FL 32789
WELCOME to 1821 WINDSOR DR in WINTER PARK, FLORIDA! This is a ONCE IN A LIFETIME OPPORTUNITY to own this BEAUTIFUL CUSTO...
Listed by CREEGAN GROUP
$14,900
Townhouse
649 N PARK AVE, Winter Park, FL 32789
Now offered for lease, this luxury brownstone at northern end of Park Avenue delivers an exceptional lifestyle in the he...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,699,000
Single Family Home
1742 BARCELONA WAY, Winter Park, FL 32789
OPPORTUNITY AWAITS – PURE POTENTIAL IN WINTER PARK'S SEVILLA NEIGHBORHOOD! Rare, Tudor-style estate sits on an oversized...
Listed by KELLY PRICE & COMPANY LLC
$1,049,000
Single Family Home
913 MOSS LN, Winter Park, FL 32789
***Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Mos...
Listed by VECTOR PROPERTY 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
$669,000
Single Family Home
2711 PARKLAND DR, Winter Park, FL 32789
Welcome to this delightful 1,600 sqft home in one of Winter Park's most coveted neighborhoods. This three-bedroom, two-b...
Listed by CORCORAN PREMIER REALTY
$1,250,000
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
$2,199,999
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
$2,950,000
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
$220,000
Condo
2500 LEE RD #208, Winter Park, FL 32789
This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring t...
Listed by KELLER WILLIAMS REALTY AT THE PARKS
$1,899,999
Single Family Home
1299 HARDING STREET, Winter Park, FL 32789
Welcome to your private slice of paradise—a beautifully renovated home with a brand new 2024 pied-à-terre guest retreat,...
Listed by FANNIE HILLMAN & ASSOCIATES
$3,850
Condo
690 OSCEOLA AVE #502, Winter Park, FL 32789
Immaculate renovated lakefront condo with partial views of Lake Virginia and the Downtown skyline. Location, location, l...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$259,000
Condo
1250 S DENNING DR #111, Winter Park, FL 32789
LOCATION LOCATION!! Now is your chance to own this STUNNING NEWLY RENOVATED 2 bed / 2 full bath FIRST FLOOR condo in the...
Listed by EXP REALTY LLC
$349,000
Single Family Home
156 OAK GROVE RD, Winter Park, FL 32789
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence in the highly desirable Winter Park Oaks commu...
Listed by EVERLANE REALTY LLC
$1,490,000
Single Family Home
2408 LAFAYETTE AVE, Winter Park, FL 32789
This brand new custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines mode...
Listed by CORCORAN PREMIER REALTY
$479,000
Single Family Home
1564 CAVENDISH RD, Winter Park, FL 32789
Nice 3BR/1bath with one-car garage in sought-after Orwin Manor. Updated kitchen includes solid wood cabinets, SS appli...
Listed by CHARLES RUTENBERG REALTY ORLANDO