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546 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)

$3,288,000
Single Family Home
731 WILLIAMS DR, Winter Park, FL 32789
Introducing a stunning brand-new custom home by Butler Ridge Development, located in the highly desirable Park Grove nei...
Listed by FANNIE HILLMAN & ASSOCIATES


$550,000
Single Family Home
2138 WHITEHALL DR, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to this well-maintained home in the desirable Kenilworth Shores ...
Listed by KELLER WILLIAMS REALTY AT THE PARKS


$450,000
Single Family Home
3317 DORMER CT, Winter Park, FL 32792
Welcome to your dream home in the heart of Central Florida! This immaculate, move-in ready 3-bedroom, 2-bath pool home i...
Listed by KELLER WILLIAMS ADVANTAGE REALTY


$2,095,000
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


$950,000
Condo
200 CAROLINA AVE #201, Winter Park, FL 32789
A unique opportunity to own this Winter Park luxury corner condo unit in the gated Park West community. Resting on the ...
Listed by PREMIER SOTHEBY'S INTL. REALTY


$725,000
Single Family Home
1129 GOLFSIDE DR, Winter Park, FL 32792
Nestled on an idyllic tree-lined street, this charming 3-bedroom, 2-bathroom POOL HOME offers the Winter Park Lifestyle ...
Listed by RE/MAX 200 REALTY


$475,000
Single Family Home
407 S LAKEMONT AVE, Winter Park, FL 32792
This adorable 3 bedroom, 1 bath mid-century modern bungalow is tucked into a highly coveted part of Winter Park. Thought...
Listed by TCA REALTY, LLC


$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


$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


$1,275,000
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


$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


$800,000
Single Family Home
600 BRECHIN DR, Winter Park, FL 32792
Welcome to one of the most sought after neighborhoods of Kenilworth Shores in Winter Park! Nestled among tree-lined stre...
Listed by KELLER WILLIAMS WINTER PARK


$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


$780,000
Single Family Home
5275 PINE LILY CIR, Winter Park, FL 32792
Welcome to your private retreat, tucked away on a quiet cul-de-sac with direct pond views. This beautifully upgraded 5-b...
Listed by RE/MAX TOWN & COUNTRY REALTY


$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


$719,000
Single Family Home
1139 FAIRWAY DR, Winter Park, FL 32792
PRICE REDUCED. BRING OFFERS. Fabulous updated home in the heart of Winter Park, where timeless charm meets tranquil Wi...
Listed by KELLER WILLIAMS WINTER PARK


$1,550,000
Single Family Home
1661 WOODLAND AVE, Winter Park, FL 32789
Fabulous Top-to-Bottom Renovation on Coveted Brick Street in Prime Winter Park Location! This exceptional 3-bedroom, 3.5...
Listed by FANNIE HILLMAN & ASSOCIATES


$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


$650,000
Single Family Home
2855 LION HEART RD, Winter Park, FL 32792
Welcome to 2855 Lion Heart Dr, Winter Park — a beautifully remodeled home that seamlessly combines modern comfort with a...
Listed by MY REALTY GROUP, LLC.


$559,900
Single Family Home
7584 LODGE POLE TRL, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Beautiful remodeled home. Luxury vinyl plank flooring throughout the en...
Listed by SAND DOLLAR REALTY GROUP INC
