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417 Properties

417 Properties for Sale In Winter Park

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1024 WADING WATERS CIR, Winter Park, FL 32792
1/55 55

$1,065,000

Open Thu 4PM-6PM

Single Family Home

4 Beds 3 Baths 3,057 SqFt

1024 WADING WATERS CIR, Winter Park, FL 32792

Welcome to 1024 Wading Waters Circle—a rare offering in the gated, amenity-rich enclave of Hawk's Crest in Winter Park. ...

Listed by PREMIER SOTHEBY'S INTL. REALTY

1640 CYPRESS POINT LN, Winter Park, FL 32792
1/37 37

$714,900

Open Fri 5PM-6:30PM

Single Family Home

3 Beds 2 Baths 1,704 SqFt

1640 CYPRESS POINT LN, Winter Park, FL 32792

Welcome to 1640 Cypress Point – a home like no other in Winter Park. This beautifully maintained 3-bedroom, 2-bathroom h...

Listed by KELLER WILLIAMS WINTER PARK

5234 OHIO ST, Winter Park, FL 32792
3D

$382,500

Open Sat 11AM-1PM

Single Family Home

3 Beds 2 Baths 1,226 SqFt

5234 OHIO ST, Winter Park, FL 32792

Tropical Vibes + Total Privacy in Winter Park! A rare find, indeed!! Tucked away at the very end of a quiet cul-de-sac, ...

Listed by MARKET CONNECT REALTY LLC

618 BLAIRSHIRE CIR, Winter Park, FL 32792
1/39 39

$699,900

Open Sun 12PM-3PM

Single Family Home

3 Beds 3 Baths 1,876 SqFt

618 BLAIRSHIRE CIR, Winter Park, FL 32792

First time on the market! This one-owner, 3-bedroom, 3-bathroom single-family pool home offers the perfect blend of clas...

Listed by FANNIE HILLMAN & ASSOCIATES

1371 LYNDALE BLVD, Winter Park, FL 32789
1/50 50

$1,349,500

Open Sat 1PM-4PM

Single Family Home

4 Beds 3 Baths 2,714 SqFt

1371 LYNDALE BLVD, Winter Park, FL 32789

One or more photo(s) has been virtually staged. As you enter this renovated 4-bedroom, 2.5-bathroom home within the city...

Listed by ALIGN REAL ESTATE LLC

512 CLARENDON AVE, Winter Park, FL 32789
1/44 44

$1,100,000

Open Sat 10AM-12PM

Townhouse

4 Beds 4 Baths 2,826 SqFt

512 CLARENDON AVE, Winter Park, FL 32789

Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins Colle...

Listed by COMPASS FLORIDA LLC

1819 SHADYHILL TER, Winter Park, FL 32792
3D

$535,000

Open Sat 2PM-4PM

Single Family Home

4 Beds 3 Baths 1,811 SqFt

1819 SHADYHILL TER, Winter Park, FL 32792

Welcome to your own private retreat, perfectly situated at the end of a quiet CUL-DE-SAC on one of the most SCENIC LOTS ...

Listed by KELLER WILLIAMS WINTER PARK

1920 WOODCREST DR #15, Winter Park, FL 32792
1/20 20

$285,000

Open Sun 11AM-1PM

Condo

2 Beds 2 Baths 1,010 SqFt

1920 WOODCREST DR #15, Winter Park, FL 32792

Gorgeous, fully renovated 2-bedroom / 2-bathroom condominium nestled in the heart of Winter Park along a beautiful and q...

Listed by COLDWELL BANKER RESIDENTIAL RE

1840 BISCAYNE DR, Winter Park, FL 32789
1/47 47

$949,000

Open Sun 1PM-3PM

Single Family Home

4 Beds 3 Baths 2,646 SqFt

1840 BISCAYNE DR, Winter Park, FL 32789

Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom H...

Listed by CORCORAN PREMIER REALTY

2211 AZALEA PL, Winter Park, FL 32789
1/99 99

$6,180,000

Open Sat 1PM-3PM

Single Family Home

5 Beds 7 Baths 7,278 SqFt

2211 AZALEA PL, Winter Park, FL 32789

Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront...

Listed by FORTUNE INTERNATIONAL REALTY

1780 MIZELL AVE., Winter Park, FL 32789
1/61 61

$1,695,000

Open Sat 12PM-2PM

Single Family Home

4 Beds 4 Baths 2,743 SqFt

1780 MIZELL AVE., Winter Park, FL 32789

Experience the height of modern luxury in this newly constructed home, masterfully designed by esteemed architect Gary H...

Listed by PREMIER SOTHEBY'S INTL. REALTY

1761 LEGION DR, Winter Park, FL 32789
1/54 54

$3,544,999

Open Sat 11AM-1:30PM

Single Family Home

5 Beds 6 Baths 4,955 SqFt

1761 LEGION DR, Winter Park, FL 32789

One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was complet...

Listed by SCANLON REALTY GROUP LLC

1339 ORCHID AVE, Winter Park, FL 32789
1/45 45

$575,000

Open Sat 10AM-3PM

Single Family Home

2 Beds 1 Bath 789 SqFt

1339 ORCHID AVE, Winter Park, FL 32789

A rare find in Winter Park: A charming Bungalow with 3-Car Garage (24x36) and detached finished Shed (10x14) for office ...

Listed by ABIDE REALTY

2607 LAFAYETTE AVE, Winter Park, FL 32789
1/72 72

$1,095,000

Open Sun 1PM-3PM

Single Family Home

4 Beds 4 Baths 2,770 SqFt

2607 LAFAYETTE AVE, Winter Park, FL 32789

Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park's most desirable neig...

Listed by FORTUNE INTERNATIONAL REALTY

2880 OLD CASTLE DR, Winter Park, FL 32792
1/46 46

$1,120,000

Open Sun 1PM-3PM

Single Family Home

5 Beds 5 Baths 3,839 SqFt

2880 OLD CASTLE DR, Winter Park, FL 32792

Welcome to this beautifully designed executive pool home with private in-law quarters, nestled on an oversized corner lo...

Listed by CORCORAN PREMIER REALTY

1521 CHESTNUT AVE, Winter Park, FL 32789
1/55 55

$1,899,900

Open Sat 1PM-3PM

Single Family Home

4 Beds 3 Baths 2,843 SqFt

1521 CHESTNUT AVE, Winter Park, FL 32789

Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, built in 2023, located in one of W...

Listed by COMPASS FLORIDA LLC

1090 WILDMEADOW RUN, Winter Park, FL 32792
1/42 42

$875,000

Open Sat 11AM-2PM

Single Family Home

4 Beds 4 Baths 2,589 SqFt

1090 WILDMEADOW RUN, Winter Park, FL 32792

One or more photo(s) has been virtually staged. This luxurious Modern Style home delivers the pinnacle lifestyle, in eve...

Listed by BHHS FLORIDA REALTY

1399 ALOMA AVE, Winter Park, FL 32789
1/38 38

$675,000

Open Sat 11AM-1PM

Single Family Home

3 Beds 2 Baths 1,804 SqFt

1399 ALOMA AVE, Winter Park, FL 32789

Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on...

Listed by FLORIDA HOMES REALTY & MTG

2525 VENETIAN WAY, Winter Park, FL 32789
3D

$1,249,000

Open Sun 2PM-4PM

Single Family Home

3 Beds 3 Baths 1,993 SqFt

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

1429 CHAPMAN CIR, Winter Park, FL 32789
1/36 36

$1,499,000

Open Sun 2PM-4PM

Single Family Home

4 Beds 4 Baths 3,116 SqFt

1429 CHAPMAN CIR, Winter Park, FL 32789

Exceptional Phil Kean-designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophistica...

Listed by CORCORAN PREMIER REALTY

2008 NOTTINGDALE LN, Winter Park, FL 32792
1/48 48

$365,000

New

Single Family Home

3 Beds 2 Baths 1,278 SqFt

2008 NOTTINGDALE LN, Winter Park, FL 32792

Nestled in the highly desirable Winter Park, Florida, 2008 Nottingdale Lane presents a meticulously updated and move-in-...

Listed by EXP REALTY LLC

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