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222 Properties Available
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$1,125,000
Single Family Home
1690 ONECO AVE, Winter Park, FL 32789
Step into this stunning one-story Spanish Mediterranean home, beautifully renovated in 2006 by renowned E2 Homes. Offeri...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$425,000
Single Family Home
328 LAKE FAIR LN, Winter Park, FL 32789
Under contract-accepting backup offers. Discover a true slice of paradise just minutes from downtown Orlando, nestled al...
Listed by RE/MAX 200 REALTY
$1,100,000
Single Family Home
1585 CHESTNUT AVE, Winter Park, FL 32789
Charming Spanish-Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida wi...
Listed by KELLER WILLIAMS WINTER PARK
$159,000
Condo
1695 LEE RD #B109, Winter Park, FL 32789
WELCOME Home! This first floor home offers easy access to this corner unit located in a prime central Winter Park locati...
Listed by EXP REALTY LLC
$489,000
Multi-Family
441 CLAY ST, Winter Park, FL 32789
Under contract-accepting backup offers. ATTENTION INVESTORS!!! DIAMOND LOCATION!! THIS IS THE MOST WONDERFUL OPORTUNITY ...
Listed by ORLANDO KEY REALTY LLC
$690,000
Townhouse
1806 MONDRIAN CIR, Winter Park, FL 32789
Experience the pinnacle of luxury lakeside living in Winter Park at our exclusive townhome community. This remarkable co...
Listed by COLDWELL BANKER RESIDENTIAL RE
$255,000
Condo
2500 LEE RD #202, Winter Park, FL 32789
2/2 * 956 SQ FT * LAKE KILLARNEY * CLOSE TO PARK AVE IN WINTER PARK * 3 MILES TO ROLLINS COLLEGE * NE...
Listed by THE ANDERSON GROUP & CO PL
$236,000
Condo
1500 GAY RD #10C, Winter Park, FL 32789
Under contract-accepting backup offers. Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on ...
Listed by REALCOM REAL ESTATE SERVICES INC
$3,400
Single Family Home
1850 WHITEHALL DR, Winter Park, FL 32789
This is a wonderful, furnished, pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. ...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,950,000
Single Family Home
622 PENN PL, Winter Park, FL 32789
Located just steps to the Golf Course and Park Avenue, in downtown Winter Park, 622 Penn Place is in the highly sought a...
Listed by COMMUNITY REALTY ASSOCIATES
$895,000
Townhouse
1762 MONDRIAN CIR, Winter Park, FL 32789
Introducing a stunning brand-new modern brownstone in the heart of Winter Park, offering access to Lake Killarney. Locat...
Listed by COLDWELL BANKER RESIDENTIAL RE
$1,825,000
Single Family Home
817 ANTONETTE AVE, Winter Park, FL 32789
Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality an...
Listed by FANNIE HILLMAN & ASSOCIATES
$2,254,000
Single Family Home
141 OAKWOOD WAY, Winter Park, FL 32789
Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area....
Listed by MAINFRAME REAL ESTATE
$2,119,000
Single Family Home
785 N PHELPS AVE, Winter Park, FL 32789
Under Construction. Completion September 2025, Nestled in the heart of Winter Park, this luxurious custom-built home sea...
Listed by COMPASS FLORIDA LLC
$1,770,000
Single Family Home
1470 PLACE PICARDY, Winter Park, FL 32789
Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,300,000
Single Family Home
1400 S PENNSYLVANIA AVE, Winter Park, FL 32789
Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. <br>You will...
Listed by JACK KELLER INC
$285,000
Condo
700 MELROSE AVE #A 22, Winter Park, FL 32789
HUGE PRICE CHANGE! <br>Welcome to this beautifully updated second-floor unit, offering a fresh and modern living exper...
Listed by FANNIE HILLMAN & ASSOCIATES
$4,500,000
Single Family Home
702 VIA BELLA, Winter Park, FL 32789
Under Construction. New Custom Home in the Desirable Winter Park Via's – Completion Expected June 2025 <br>This exceptio...
Listed by FLORIDIAN REALTY GROUP LLC
$144,900
Condo
1695 LEE RD #A209, Winter Park, FL 32789
Beautiful 1-Bedroom Condo in prime location! This Waterfall Cove at Winter Park condo presents, a spacious open layout a...
Listed by FUSILIER REALTY GROUP
$995,000
Single Family Home
1975 BISCAYNE DR, Winter Park, FL 32789
Under contract-accepting backup offers. Custom-Built Home with Unique Features in a Prime Winter Park Location! <br>Dis...
Listed by SOGO REAL ESTATE SERVICES LLC
$369,699
Condo
690 OSCEOLA AVE #209, Winter Park, FL 32789
Welcome to 690 Osceola Avenue, a lakefront complex in the heart of Winter Park. This sleek, modern residence offers the ...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$2,350
Condo
1055 S KENTUCKY AVE #4, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dini...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$2,350
Condo
1055 S KENTUCKY AVE #1, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$2,350
Condo
1055 S KENTUCKY AVE #2, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV