528 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)

$485,000
Single Family Home
2886 CAREW AVE, Winter Park, FL 32789
This charming 4 bedroom home is available now! With lots of open space, a cozy fireplace, and a walk-in closet in the pr...
Listed by OLDE TOWN BROKERS INC


$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


$470,000
Single Family Home
3001 LITTLE CYPRESS CV, Winter Park, FL 32792
Welcome to your dream home in the heart of Winter Parks sought after Hyde Park community. Situated at the end of a quiet...
Listed by PIXEL REALTY


$2,995
Single Family Home
1931 OGLESBY AVE, Winter Park, FL 32789
Location, Location, Location... Offered here is an Amazing Rental with many potential options of usage... 4 Bedrooms and...
Listed by KEEN REALTY GROUP, INC.


$2,545
Townhouse
7628 ALOMA PINES CT, Winter Park, FL 32792
This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and l...
Listed by REAL PROPERTY MANAGEMENT AND REALTY


$1,950
Single Family Home
1966 BISCAYNE DR, Winter Park, FL 32789
This rental is AVAILABLE for move in May 18th 2025! Welcome to Winter Park. This single family home features 2 bedrooms ...
Listed by MAINFRAME REAL ESTATE


$1,799
Condo
3007 GEORGE MASON AVE #H-3D, Winter Park, FL 32792
Move-in ready and beautifully updated, this two-story condo in the desirable Colonies Community offers 2 bedrooms and 2....
Listed by ALLEGIANT MANAGEMENT GROUP, INC


$1,700
Condo
7350 SWALLOW RUN, Winter Park, FL 32792
For Rent. Available June 1st. Spacious 2-bedroom, 2-bathroom ground-floor. Features tile flooring throughout, granite co...
Listed by GHALI REALTY, INC


$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


$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


$1,100
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


$1,899,000
Single Family Home
2402.5 TEMPLE DR, Winter Park, FL 32789
Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 1...
Listed by OLDE TOWN BROKERS INC


$1,450,000
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


$340,000
Townhouse
2487 HARBOUR WAY, Winter Park, FL 32792
Unmissable opportunity in Winter Park! <br> <br>Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for t...
Listed by WRA BUSINESS & REAL ESTATE


$3,950
Single Family Home
1031 WILDMEADOW RUN, Winter Park, FL 32792
Located in the private, gated community of Hawks Crest, this 4-bedroom, 3.5-bath home built in 2020 offers modern living...
Listed by EXP REALTY LLC


$839,000
Single Family Home
2168 MARSH SEDGE LN, Winter Park, FL 32792
Welcome to your future home, where style, comfort, and technology come together seamlessly. This stunning 4-bedroom, 3-b...
Listed by SELECTA REALTY LLC


$585,000
Single Family Home
2441 BANCHORY RD, Winter Park, FL 32792
Under contract-accepting backup offers. Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the highly d...
Listed by FANNIE HILLMAN & ASSOCIATES


$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


$120,000
Condo
316 SCOTTSDALE SQ #316, Winter Park, FL 32792
Welcome to 316 Scottsdale Square, a delightful 2-bedroom, 1 and half bathroom condo located in desirable Winter Park. Th...
Listed by JADE KEY REALTY LLC


$6,800
Condo
311 E MORSE BLVD #2-3, Winter Park, FL 32789
Enjoy the perfect blend of modern comfort and timeless charm in this beautifully updated 2-bedroom, 2-bathroom condo for...
Listed by CHARLES RUTENBERG REALTY ORLANDO


$4,000
Single Family Home
1936 SUMMERFIELD RD, Winter Park, FL 32792
Welcome to 1936 Summerfield Rd, Winter Park, FL 32792 – a stylish and efficient 3-bedroom, 2-bath home just outside Bald...
Listed by HOST MANAGEMENT GROUP LLC


$1,165,000
Single Family Home
2832 BEAR ISLAND POINTE, Winter Park, FL 32792
Under contract-accepting backup offers. Welcome to 2832 Bear Island Pointe in Winter Park's premier gated community, Cyp...
Listed by COMPASS FLORIDA LLC


$1,025,000
Single Family Home
2923 COVE TRL, Winter Park, FL 32789
Under contract-accepting backup offers. A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILIT...
Listed by KELLER WILLIAMS ADVANTAGE III
