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- $ 400,000
- $ 600,000
- $ 1,000,000
464 Properties Available In Winter Park
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- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
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$2,400
Condo
1055 S KENTUCKY AVE #4, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dini...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$599,900
Single Family Home
1116 FAIRWAY DR, Winter Park, FL 32792
Welcome to this beautiful, single-family home in the Golfside Community in Winter Park! This stunning 3-bedroom, 2-bathr...
Listed by INNOVATIVE REALTY, LLC
$100,000
Single Family Home
2667 FITZHUGH RD, Winter Park, FL 32792
MULTIPLE OFFERS RECEIVED. REQUESTING HIGHEST AND BEST BY JAN 16TH AT 10AM. What a great location! Winter Park address...
Listed by RE/MAX PRIME PROPERTIES
$94,900
Condo
273 SCOTTSDALE SQ #273, Winter Park, FL 32792
Under contract-accepting backup offers. Located on the First Floor, this single-story condo features a one bedroom and o...
Listed by COLDWELL BANKER RESIDENTIAL RE
$6,800
Condo
315 E NEW ENGLAND AVE #13, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Experience the lifestyle of elegance and luxury at Villa Siena, known as...
Listed by ONE OAK REALTY CORP
$4,590
Single Family Home
2504 TUSCALOOSA TRL, Winter Park, FL 32789
This stunning 3-bedroom (previously 4), 2.5-bath home has been thoughtfully updated with modern comfort and style. The o...
Listed by LIPPI REALTY LLC
$2,600
Condo
1055 S KENTUCKY AVE #1, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$2,400
Condo
1055 S KENTUCKY AVE #2, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$1,990
Condo
2500 LEE RD #S, Winter Park, FL 32789
Discover this stunning gem nestled in the sought-after Lake Killarney community. This charming corner unit boasts privac...
Listed by LIPPI REALTY LLC
$960,000
Single Family Home
830 W CANTON AVE, Winter Park, FL 32789
***MODERN LUXURY LIVING IN THE HEART OF WINTER PARK.*** <br>Welcome to your Dream Home at 830 W Canton Av. Every detail ...
Listed by COLDWELL BANKER REALTY
$525,000
Single Family Home
2073 SHADYHILL TER, Winter Park, FL 32792
Nestled on a lushly landscaped corner lot, this beautiful Winter Park, FL homes offers a serene retreat with picturesque...
Listed by KROLL REALTY GROUP
$250,000
Condo
2482 TAHOE CIR #2482, Winter Park, FL 32792
Beautifully updated end-unit home in the sought-after Cedarwood Village community of Winter Park! This charming property...
Listed by UNITED REAL ESTATE PREFERRED
$749,900
Townhouse
1521 HARMON AVE, Winter Park, FL 32789
Welcome home to this stunning and unique tri-level townhome that offers a bright and open floor plan with no HOA or dues...
Listed by ALL REAL ESTATE & INVESTMENTS
$649,900
Single Family Home
631 CALLAHAN ST, Winter Park, FL 32789
Completely renovated inside and out! Kitchen 2022, bathrooms 2022, windows 2022, fence 2022, roof 2023, pavers pergola a...
Listed by HOUWZER LLC
$115,000
Condo
293 SCOTTSDALE SQ #293, Winter Park, FL 32792
Additional Pictures to come. <br>Calling all INVESTORS!! Calling all First-Time Home-Buyers!! This beautiful unit in Win...
Listed by COLDWELL BANKER RESIDENTIAL RE
$1,900
Condo
1512 INDIANA AVE #C, Winter Park, FL 32789
Spacious ONE BEDROOM , one bath CONDO available now! This is a first floor apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$11,900,000
Single Family Home
1120 PRESERVE POINT DR, Winter Park, FL 32789
Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean Estate i...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$2,995,000
Single Family Home
884 AUDUBON LN, Winter Park, FL 32789
Discover an extraordinary opportunity to own a one-story lakefront retreat on the picturesque Lake Mizell, part of the c...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,495,000
Single Family Home
907 MOSS LN, Winter Park, FL 32789
Tuscan-inspired Mediterranean gem in the Via's of olde Winter Park. Step into the charm of an Italian villa with this el...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,395,000
Single Family Home
433 CAROLINA AVE, Winter Park, FL 32789
From the boutique address at 433 Carolina Ave, take a stroll down to historic Hannibal Square or to the New England gour...
Listed by COLDWELL BANKER RESIDENTIAL RE
$849,000
Single Family Home
744 LONDON RD, Winter Park, FL 32792
Step into a home where luxury, style, and functionality come together seamlessly! This stunning 2,804-square-foot pool h...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$600,000
Single Family Home
513 CORNWALL RD, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Location, Location, Location! Don't miss this opportunity to own a charm...
Listed by BHHS FLORIDA REALTY
$485,000
Townhouse
2909 CLEVER LN, Winter Park, FL 32792
Welcome to 2909 Clever Lane, Winter Park, Florida! This stunning 3-bedroom, 2.5-bathroom townhome offers over 1,900 squa...
Listed by CREEGAN GROUP
$430,000
Single Family Home
2206 WINTER WOODS BLVD, Winter Park, FL 32792
Under contract-accepting backup offers. Welcome to this lovely home in the Winter Park area with plenty of room to grow!...
Listed by KELLER WILLIAMS WINTER PARK