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

$550,000
Single Family Home
720 N PENNSYLVANIA AVE, Winter Park, FL 32789
Nestled in one of Winter Park's most sought-after locations, this 3-bedroom, 2-bathroom home seamlessly blends modern el...
Listed by RE/MAX TOWN & COUNTRY REALTY


$1,550
Condo
7340 SWALLOW RUN #7340, Winter Park, FL 32792
Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centr...
Listed by METRO CITY REALTY


$1,250
Condo
3035 GEORGE MASON AVE #20D, Winter Park, FL 32792
Welcome to 3035 George Mason Avenue, Unit #20B—a cozy and inviting 1-bedroom, 1-bathroom retreat in the heart of beautif...
Listed by EXP REALTY LLC


$245,000
Condo
1913 WOODCREST DR #B, Winter Park, FL 32792
Winter Park gem! Tastefully updated 2-bedroom, 2-bathroom corner condominium with a spacious patio is your rare cha...
Listed by FUTURE HOME REALTY INC


$191,000
Condo
3651 N GOLDENROD RD #210, Winter Park, FL 32792
beautiful Condo in of Winter Park. <br> <br>This spacious second-floor unit is filled with natural light from its large ...
Listed by WRA BUSINESS & REAL ESTATE


$185,000
Condo
224 LEWFIELD CIR, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ The perfect ...
Listed by WEMERT GROUP REALTY LLC


$80,000
Condo
185 SCOTTSDALE SQ #185, Winter Park, FL 32792
Beautifully maintained and updated 2 Bedroom and 2 Bath condo in Winter Park! Easy to care for tile floors flow through ...
Listed by FANNIE HILLMAN & ASSOCIATES


$100,000
Condo
166 SCOTTSDALE SQ #166, Winter Park, FL 32792
Take a look this charming 2nd-floor condominium featuring 2 bedrooms and 2 bathrooms in Winter Park. Conveniently locate...
Listed by KYLIN REALTY LLC


$1,295,000
Single Family Home
1611 CHESTNUT AVE, Winter Park, FL 32789
Welcome to this stunning, fully renovated home in the heart of Winter Park. Located on Chestnut avenue beautifully rebui...
Listed by PARK AVENUE REALTY LLC


$429,990
Single Family Home
7427 HOUSTON CT E, Winter Park, FL 32792
Under contract-accepting backup offers. Charming Newly Remodeled Home with Modern Touches and Ample Outdoor Space Discov...
Listed by FUTURE HOME REALTY INC


$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


$795,000
Single Family Home
625 BRECHIN DR, Winter Park, FL 32792
PICTURE PERFECT HOME IN WINTER PARK'S KENILWORTH SHORES! Homes of this quality and preservation hardly come on the marke...
Listed by KELLY PRICE & COMPANY LLC


$449,900
Single Family Home
5359 LANYARD CT, Winter Park, FL 32792
MOTIVATED SELLER. Meticulously Maintained Corner-Lot Pool Home with Modern Upgrades & No HOA! <br> <br>Pride of ownershi...
Listed by REDFIN CORPORATION


$400,000
Single Family Home
7331 BLUE JACKET PL W, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Incredible Value! Priced to sell under market value! This is your oppor...
Listed by NETWORTH REALTY OF ORLANDO, LLC


$275,000
Townhouse
2464 HARBOUR WAY, Winter Park, FL 32792
New Price !!Location Winter Park! Charming 2-Bedroom, 2-Bath Single-Story Townhouse – Priced to Sell! This well-located...
Listed by AGENT TRUST REALTY CORPORATION


$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


$170,000
Condo
7340 DANIEL WEBSTER DR #7, Winter Park, FL 32792
Charming 3-Bedroom, 2-Bath Condo in Prime Location! <br> <br>Welcome to this beautifully updated 3-bedroom, 2-bath condo...
Listed by EXP REALTY LLC


$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


$284,000
Single Family Home
1727 WINTER GREEN BLVD, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to this fabulous area! Discover a bright interior tied together...
Listed by OPENDOOR BROKERAGE 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


$409,000
Single Family Home
927 MARE BELLO DR, Winter Park, FL 32792
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. LOCATION, LOCATION! Welcome to 9...
Listed by LA ROSA REALTY KISSIMMEE


$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


$154,000
Condo
116 SCOTTSDALE SQ #2, Winter Park, FL 32792
Located in Winter Park near Winter Pines Golf Club & minutes from Baldwin Park, 243 Scottsdale Square is a fantastic 2-b...
Listed by RE/MAX TOWN & COUNTRY REALTY
