67 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$740,000
Single Family Home
2478 WHITEHALL CIR, Winter Park, FL 32792
Expect to be impressed with this updated 3BR home in one of Winter Park's well- <br>established neighborhoods. It starts...
Listed by LPT REALTY, LLC
$3,250
Single Family Home
1946 STRATHAVEN RD, Winter Park, FL 32792
$100 OFF THE FIRST 6 MONTHS <br> <br> <br>For Rent – Spacious 3BR Home in Prime Winter Park Location! <br> <br>LOCATION,...
Listed by LPT REALTY, LLC
$100,000
Condo
126 SCOTTSDALE SQ #126, Winter Park, FL 32792
Great location!! Discover the charm of this beautifully maintained condo at 126 Scottsdale Square, nestled in a serene a...
Listed by LPT REALTY
$3,300
Single Family Home
2680 FITZHUGH RD, Winter Park, FL 32792
Beautifully remodeled and ideally located, this 4-bedroom, 3-bathroom home in Winter Park Pines offers the perfect blend...
Listed by BHHS FLORIDA REALTY
$2,500
Single Family Home
7733 FOX KNOLL PL, Winter Park, FL 32792
Welcome to this stunning 3-bedroom, 2-bathroom home in the wonderful Winter Park! Step inside and discover a beautiful l...
Listed by THE REALTY MEDICS
$379,999
Single Family Home
3383 HAMLET LOOP, Winter Park, FL 32792
Charming Winter Park Home with Private Pool on Corner Lot! <br> <br>Don't miss this beautifully updated 3-bedroom, 2-bat...
Listed by FLATFEE.COM
$425,000
Single Family Home
524 BYRON RD, Winter Park, FL 32792
Welcome to a charming and beautiful 3-bedroom, 2-bathroom home in one of Winter Park's most convenient and sought-after...
Listed by RE/MAX 200 REALTY
$624,900
Single Family Home
7988 PLEASANT PINE CIR, Winter Park, FL 32792
Stylish, Updated & Move-In Ready in Gated Winter Park Community! <br>Welcome to this impeccably maintained 4-bedroom, 2....
Listed by ABSOLUTE REALTY GROUP, LLC
$474,999
Single Family Home
7602 LODGE POLE TRL, Winter Park, FL 32792
Nestled in desirable Arrowhead Cove, this meticulously maintained 3-bedroom, 2.5-bath home represents the pinnacle of Wi...
Listed by KELLER WILLIAMS CLASSIC
$2,690
Single Family Home
7431 PORTSIDE CT, Winter Park, FL 32792
Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with fu...
Listed by MAIN STREET RENEWAL LLC
$475,000
Townhouse
1330 MERRYDALE WAY, Winter Park, FL 32792
Welcome to Enclave at Hawks Crest! This corner-unit 3-bedroom, 2.5-bath townhome offers added privacy, extra natural lig...
Listed by SELECTA REALTY LLC
$1,747
Townhouse
Winter Park, FL 32792
Winter Park 2 Bedroom Upgraded Condo <br>This unit is tiled throughout with Granite counter tops No carpet to worry abou...
Listed by THE REALTY FACTOR INC
$735,000
Single Family Home
346 ELKHORN CT, Winter Park, FL 32792
Welcome to your next chapter in Winter Park Pines, tucked within the most sought-after school district in all of Orlando...
Listed by 407 PROPERTIES
$1,980
Mobile Home
7034 EASTER ST, Winter Park, FL 32792
Location!! This completely renovated home is now available for rent and can be yours! With 3 bedrooms and 1 bathroom, th...
Listed by ELIZUNDIA LUXURY REALTY LLC
$1,499
Condo
1000 S SEMORAN BLVD #703, Winter Park, FL 32792
Spacious one-bedroom condominium in Golfside Villas! This move in ready first-floor unit includes a large living room, D...
Listed by CENTURY 21 CARIOTI
$650,000
Single Family Home
3759 KINSLEY PL, Winter Park, FL 32792
EXPECT TO BE IMPRESSED! Tucked away in a quaint and quiet Winter Park neighborhood, this beautifully maintained two-stor...
Listed by COMPASS FLORIDA LLC
$759,000
Single Family Home
620 DARCEY DR, Winter Park, FL 32792
New Roof installed July 2025. Charming brick Winter Park home in the desirable Brookshire Heights neighborhood. This hom...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$650,000
Single Family Home
3115 HEARTLEAF PL, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Park, FL! Motivated seller that is ...
Listed by EXP REALTY LLC
$658,900
Single Family Home
3110 HEARTLEAF PL, Winter Park, FL 32792
Beautiful pool home with an open great room plan with high vaulted ceilings and master on the first floor situated on on...
Listed by RE/MAX PRIME PROPERTIES
$580,000
Single Family Home
8065 PLEASANT PINE CIR, Winter Park, FL 32792
**This property qualifies for a closing cost credit up to $8,800 through the Seller's preferred lender.**Welcome home to...
Listed by KELLER WILLIAMS REALTY AT THE PARKS
$180,000
Condo
3651 N GOLDENROD RD #E205, Winter Park, FL 32792
Well maintained 2 bedroom/2 bathroom condo located in Lancelot of Winter Park. This spacious second floor unit with larg...
Listed by COLDWELL BANKER REALTY
$255,000
Condo
2480 TAHOE CIR #2480, Winter Park, FL 32792
Seminole County and Winter Park! Centrally located on the border of Orange County, this well-established community of C...
Listed by UNITED REAL ESTATE PREFERRED
$3,095
Single Family Home
3486 BOUGAINVILLEA DR #B, Winter Park, FL 32792
Location! Location! Location! This exactly what you are looking for, a nice home in a great location. This a great unit ...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$2,395
Single Family Home
3486 BOUGAINVILLEA DR #A, Winter Park, FL 32792
Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the hear...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV