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485 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)

$1,400,000
Single Family Home
2525 VENETIAN WAY, Winter Park, FL 32789
Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake Access <br>This meticulously renovated 3-bed, 2.5-...
Listed by KELLY PRICE & COMPANY LLC


$800,000
Single Family Home
441 N CAPEN AVE, Winter Park, FL 32789
Rare find in the heart of Historic West Winter Park - Newer 2017 solid built David Weekley home now available! This mode...
Listed by COLDWELL BANKER RESIDENTIAL RE


$649,900
Single Family Home
236 N RANGER BLVD, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Fully Renovated – EXPERIENCE WINTER PARK! This beautifully updated quart...
Listed by EXP REALTY LLC


$400,000
Townhouse
264 BALFOUR DR, Winter Park, FL 32792
Welcome to 264 Balfour Drive — an exclusive residence within a private enclave of just 13 elegant townhomes in the heart...
Listed by FANNIE HILLMAN & ASSOCIATES


$235,000
Condo
1250 S DENNING DR #230, Winter Park, FL 32789
Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floo...
Listed by FANNIE HILLMAN & ASSOCIATES


$1,025,000
Single Family Home
2923 COVE TRL, Winter Park, FL 32789
A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market ...
Listed by KELLER WILLIAMS ADVANTAGE III


$1,150,000
Single Family Home
795 W CANTON AVE, Winter Park, FL 32789
Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just a short stroll to iconic Park Avenue and...
Listed by WEICHERT REALTORS HALLMARK PROPERTIES


$1,299,000
Single Family Home
1341 LYNDALE BLVD, Winter Park, FL 32789
Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park V...
Listed by COMPASS FLORIDA LLC


$2,295,000
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


$3,195,000
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


$420,000
Single Family Home
3063 ASH PARK LOOP, Winter Park, FL 32792
Location, Location, Location! Welcome to Hyde Park! This lovely home in Winter Park offers a blend of amenities and clas...
Listed by ANDERSON INVESTMENT PROPERTIES


$1,150,000
Single Family Home
2011 SOARING OAK WAY, Winter Park, FL 32792
RATE BUY DOWN OPTION AVAILABLE on this stunning 4,300 square foot home in sought after Waters Edge at Hawks Crest in Win...
Listed by DEGREE REALTY LLC


$285,000
Condo
151 N ORLANDO AVE #115, Winter Park, FL 32789
Fantastic 2 bed/ 1 bath - first floor condo in cool, mid-century building on Lake Killarney. This home is next to Trader...
Listed by FANNIE HILLMAN & ASSOCIATES


$279,900
Condo
2309 SUN VALLEY CIR #2309, Winter Park, FL 32792
Welcome to the largest floor plan in the community! This beautifully maintained 2 bedroom, 2 bathroom condo offers a fre...
Listed by CENTURY 21 INTEGRA


$478,000
Single Family Home
7320 FIELDCREST AVE, Winter Park, FL 32792
MOVE IN TODAY!! Welcome to your dream home in a quiet neighborhood as you relax by the private pool. Leave all the worr...
Listed by COLDWELL BANKER REALTY


$415,000
Single Family Home
5144 GOLDENROD PLACE RD, Winter Park, FL 32792
Nestled on an oversized lot at the end of a peaceful cul-de-sac, this charming home offers the perfect blend of privacy ...
Listed by C. APOLLO REALTY INC


$1,385,000
Single Family Home
1370 ALBERTA DR, Winter Park, FL 32789
Discover luxurious lakeside living in prestigious Winter Park, where this extensively updated pool home offers the perfe...
Listed by FANNIE HILLMAN & ASSOCIATES


$849,999
Single Family Home
2418 WHITEHALL CIR, Winter Park, FL 32792
A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story pro...
Listed by CORCORAN PREMIER REALTY


$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


$527,000
Single Family Home
4026 TENITA DR, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to this stunning property where elegance meets comfort. The neut...
Listed by OPENDOOR BROKERAGE LLC


$1,750,000
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


$440,000
Single Family Home
5001 TANGERINE AVE, Winter Park, FL 32792
Charming Winter Park Home with Pool <br> <br>Welcome to 5001 Tangerine Avenue, a bright and welcoming 3-bedroom, 2-bath ...
Listed by MARK SPAIN REAL ESTATE


$14,000
Single Family Home
909 SEMINOLE DR, Winter Park, FL 32789
FOR LEASE - STUNNING, COMPLETELY REMODELED BY SKOLFIELD HOMES GUEST HOUSE - IN THE GOLDEN TRIANGLE, WALKING DISTANCE TO...
Listed by KELLY PRICE & COMPANY LLC


$1,125
Condo
7429 DANIEL WEBSTER DR #B-15C, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to this charming 1-bedroom, 1-bathroom house located in the desi...
Listed by TRANSCEND REALTY
