- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
109 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)

$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


$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


$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


$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


$219,900
Condo
2348 SUN VALLEY CIR, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Dreams Do Come True! Spectacular Opportunity in Sought-After Cedarwood V...
Listed by INVESTOR'S REAL ESTATE LLC


$1,650
Condo
3651 N GOLDENROD RD #B207, Winter Park, FL 32792
Beautifully Updated 2-Bed/2-Bath Condo Near UCF & Full Sail! <br> <br>Step into this stylish and freshly updated second-...
Listed by MAINFRAME REAL ESTATE


$724,900
Condo
640 KILLARNEY BAY CT #4, Winter Park, FL 32789
Tucked away on the tranquil shores of Lake Killarney, this impeccably remodeled two-story residence offers a rare opport...
Listed by COMPASS FLORIDA LLC


$679,000
Single Family Home
2817 PRINCE JOHN RD, Winter Park, FL 32792
NEW ROOF 2019! GREAT PRICE! SPECTACULAR WINTER PARK HOME COMPLETELY RENOVATED AND UPGRADED INCLUDING A STUNNING KITCHEN!...
Listed by LORI GILMORE REAL ESTATE LLC


$2,040
Single Family Home
Winter Park, FL 32792
Updated 3 BED, 2 BATH HOME IN ESTABLISHED WINTER PARK NEIGHBORHOOD! This lovely 1,669 sq ft home has beautiful ceramic t...
Listed by KELLER WILLIAMS REALTY AT THE PARKS


$639,000
Condo
100 S INTERLACHEN AVE #107F, Winter Park, FL 32789
Welcome to the heart of Winter Park living! This beautifully updated 2 bedroom, 1 bath, first floor condo offers the per...
Listed by MAINFRAME REAL ESTATE


$474,500
Townhouse
1628 LITTLE WREN LN, Winter Park, FL 32792
Improved Price! Welcome to your private "nest" on Little Wren. Nestled among the trees, this modern masterpiece is loca...
Listed by PARKSIDE PROPERTIES, 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


$95,000
Condo
337 SCOTTSDALE SQ #337, Winter Park, FL 32792
This well-maintained unit offers a combination of functionality, comfort, and an excellent location. The unit features t...
Listed by HOMERIVER GROUP


$2,099,000
Single Family Home
1299 HARDING STREET, Winter Park, FL 32789
Welcome to your private slice of paradise—a beautifully renovated home with a brand new 2024 pied-à-terre guest retreat,...
Listed by FANNIE HILLMAN & ASSOCIATES


$600,000
Single Family Home
3019 NORTHWOOD BLVD, Winter Park, FL 32789
WINTER PARK 32789 - Mid Century design. Unique neighborhood - walk to shopping, restaurants, entertainment. 3/1.5 Bath w...
Listed by SAND DOLLAR REALTY GROUP INC


$2,095
Single Family Home
1445 CHILEAN LN, Winter Park, FL 32792
No security deposit required to qualified applicants! This property is enrolled with Obligo, allowing qualified renters ...
Listed by RE/MAX TOWN & COUNTRY REALTY


$89,000
Condo
7341 DANIEL WEBSTER DR #4, Winter Park, FL 32792
JUST REDUCED THE PRICE!!! NEWLY REMODELED WITH MODERN STYLE! PERFECT PROPERTY FOR THE PRICE! GREAT FOR INVESTORS OR F...
Listed by PROFESSIONAL PROPERTY MGMT & L


$249,900
Condo
255 SANDLEWOOD TRL, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Dreams Do Come True! FHA, VA, and DPA approved, making it a smart choice...
Listed by INVESTOR'S REAL ESTATE LLC


$1,795
Condo
300 SCOTTSDALE SQ #300, Winter Park, FL 32792
Charming 2-bedroom, 1.5-bathroom townhouse in Winter Park's Winter Park Woods community. This two-story unit features ne...
Listed by LA ROSA REALTY ORLANDO LLC


$359,000
Single Family Home
156 OAK GROVE RD, Winter Park, FL 32789
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence in the highly desirable Winter Park Oaks commu...
Listed by EVERLANE REALTY LLC


$489,900
Single Family Home
4887 SEMINOLE AVE, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Location, Location, Location!!!! Winter Park Florida: Large 4 Bedroom 3 ...
Listed by CHARLES RUTENBERG REALTY ORLANDO


$550,000
Single Family Home
1430 HYDE PARK DR, Winter Park, FL 32792
Step inside and be ready to see an AMAZING LAKE VIEW from this SPLIT plan, 2 bedroom 2 bath BEAUTIFUL home. NEW LUXURY ...
Listed by KELLER WILLIAMS ADVANTAGE REALTY


$189,900
Condo
200 SAINT ANDREWS BLVD #1603, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to FOUR SEASONS... a serene, centrally located community in Wint...
Listed by FANNIE HILLMAN & ASSOCIATES


$69,900
Condo
194 SCOTTSDALE SQ #194, Winter Park, FL 32792
Spacious 2-Bedroom Winter Park Condo – Prime Location & Incredible Potential! CONDO FEES PAID THROUGH JUNE FOR THE BUYER...
Listed by THE NAVY HOUSE
