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540 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)

$219,000
Condo
7468 SWALLOW RUN #38, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to this charming two bedroom, two and a half bathroom condo in t...
Listed by CREEGAN GROUP


$950,000
Single Family Home
5325 CYPRESS RESERVE PL, Winter Park, FL 32792
Your Dream Home Awaits! <br>Imagine a home that blends luxury, comfort, & convenience that's exactly what you'll find at...
Listed by LPT REALTY, LLC


$1,750
Condo
200 SAINT ANDREWS BLVD #2108, Winter Park, FL 32792
This 2 bedroom, 2 bathroom condo is located in Winter Park's desirable Four Seasons community. Enjoy all Winter Park has...
Listed by REAL PROPERTY MANAGEMENT AND REALTY


$1,299,000
Single Family Home
2536 BROOKSHIRE AVE, Winter Park, FL 32792
Welcome to 2536 Brookshire Ave, a spacious 4-bedroom, 3.5-bath modern farmhouse located in the heart of Winter Park. The...
Listed by PALMANO GROUP RE BROKERAGE LLC


$1,070,000
Single Family Home
250 CORTLAND AVE, Winter Park, FL 32789
Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of th...
Listed by EXP REALTY LLC


$565,000
Single Family Home
230 S RANGER BLVD, Winter Park, FL 32792
Under contract-accepting backup offers. Beautifully updated and FURNISHED (upon negotiation) 3-bedroom, 2-bath home in t...
Listed by KELLY PRICE & COMPANY LLC


$189,000
Condo
200 SAINT ANDREWS BLVD #2804, Winter Park, FL 32792
FOUR SEASONS CONDO IN Winter Park is Centrally located. Great community with a clubhouse, a fitness center recently ren...
Listed by BETTER HOMES & GARDENS RE STAR


$100,000
Condo
101 SCOTTSDALE SQ #101, Winter Park, FL 32792
Welcome to this spacious and modern 2 bedroom, 2 bathroom condominium located in Winter Park, FL, just minutes from Full...
Listed by EXP REALTY LLC


$97,000
Condo
3071 GEORGE MASON AVE #5, Winter Park, FL 32792
Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat! <br>Welcome to this well-maintained groun...
Listed by CASTLE & COTTAGE REALTY LLC


$1,695
Single Family Home
1714 MILLER AVE, Winter Park, FL 32789
Welcome to this charming duplex nestled in the heart of Winter Park. This 2-bedroom one bathroom with a one car carport ...
Listed by RE/MAX 200 REALTY


$1,695
Single Family Home
1716 MILLER AVE, Winter Park, FL 32789
Welcome to this charming duplex nestled in the heart of Winter Park. This 2-bedroom one bathroom with a one car carport ...
Listed by RE/MAX 200 REALTY


$1,235
Condo
261 SCOTTSDALE SQ #261, Winter Park, FL 32792
Spacious & Cozy 1 Bed/1 Bath Apartment for Rent – Prime Location Near Important Universities! <br>Don't miss this opport...
Listed by AGENT TRUST REALTY CORPORATION


$748,000
Single Family Home
607 DUNBLANE DR, Winter Park, FL 32792
Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenu...
Listed by CHARLES RUTENBERG REALTY ORLANDO


$479,900
Condo
535 N INTERLACHEN AVE #107, Winter Park, FL 32789
Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor...
Listed by FANNIE HILLMAN & ASSOCIATES


$469,900
Townhouse
2037 CANNY CV, Winter Park, FL 32792
Nestled in the coveted Grayson Square community of highly desired Winter Park, FL, 2037 Canny Cove Lane is a contemporar...
Listed by LPT REALTY, LLC


$457,900
Single Family Home
4442 GLENVIEW LN, Winter Park, FL 32792
Under contract-accepting backup offers. MOVE-IN READY HOME IN WINTER PARK! This immaculate ranch-style home has been mai...
Listed by REPETTO REALTY GROUP LLC


$450,000
Single Family Home
4991 TANGERINE AVE, Winter Park, FL 32792
Welcome to 4991 Tangerine Ave in the heart of Winter Park! This charming 4-bedroom, 2-bathroom home offers comfortable l...
Listed by KELLER WILLIAMS ADVANTAGE REALTY


$425,000
Single Family Home
3121 HEARTWOOD AVE, Winter Park, FL 32792
Under contract-accepting backup offers. **This property qualifies for a closing cost credit up to $6,600 through the Sel...
Listed by KELLER WILLIAMS REALTY AT THE PARKS


$410,000
Single Family Home
1921 TAYLOR AVE, Winter Park, FL 32792
Under contract-accepting backup offers. This 3-bedroom, 2-bathroom single-family home in Winter Park, Florida, offers a ...
Listed by EXP REALTY LLC


$395,000
Single Family Home
1021 MARE BELLO DR, Winter Park, FL 32792
Here it is! A great Single-Family Home in Winter Park HS district. Check out this beautiful freshly painted interior sin...
Listed by THE WILKINS WAY LLC


$389,000
Single Family Home
2805 BONGART RD, Winter Park, FL 32792
Welcome to this charming 3-bedroom, 2-bathroom single-story home, perfectly located in highly sought-after Winter Park. ...
Listed by CENTURY 21 CARIOTI


$89,000
Condo
7309 DANIEL WEBSTER DR #D, Winter Park, FL 32792
Turnkey Investment Opportunity in Winter Park! <br>Attention investors and savvy buyers—this 1-bedroom, 1-bath condo in ...
Listed by EXP REALTY LLC


$1,095,000
Single Family Home
1444 PELICAN BAY TRL, Winter Park, FL 32792
A True Gem on the Lake! <br> <br>If you've been dreaming of owning a lakefront property with a Winter Park address, this...
Listed by TRANSCEND REALTY


$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
