Winter Park, FL 55+ active adult communities & homes for sale

2,487 homes near Winter Park

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4 rating (17 reviews)

The Villages®

<$100k - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.7 rating (18 reviews)

Solivita

$100Ks - $600Ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

3.6 rating (48 reviews)

Latitude Margaritaville

$300Ks - $900Ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

5 rating (1 reviews)

Plantation Bay Golf &...

$200Ks - $4Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$200Ks - $500Ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

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5 rating (2 reviews)

Plantation at Leesburg

$100Ks - $500Ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

5 rating (3 reviews)

Stonecrest

$200Ks - $500Ks

Stonecrest, Summerfield, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes

5 rating (7 reviews)

Kings Ridge

$200Ks - $400Ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

5 rating (3 reviews)

Twin Lakes

$200Ks - $600Ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Grand Haven

$300Ks - $1Ms

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

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Pelican Bay Daytona Beach

$100Ks - $500Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $300Ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

5 rating (1 reviews)

Cypress Lakes

$100Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $800Ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

Venetian Bay

$200Ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

5 rating (2 reviews)

Heritage Isle

$200Ks - $500Ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes

3.8 rating (6 reviews)

Trilogy® Orlando

$200Ks - $500Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

5 rating (8 reviews)

Royal Highlands

$200Ks - $500Ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

5 rating (1 reviews)

Del Webb Sunbridge

$300Ks - $1Ms

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

Del Webb at Viera

$300Ks - $800Ks

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300Ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

5 rating (1 reviews)

Sandpiper Golf & Coun...

$200Ks - $400Ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

3.6 rating (5 reviews)

Heritage Hills

$200Ks - $500Ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300Ks - $600Ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

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Questions? Call us: (888) 625-4885

Halifax Plantation

$200Ks - $700Ks

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 homes

5 rating (1 reviews)

Legacy of Leesburg

$200Ks - $400Ks

Legacy of Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes

Breakaway Trails

$400Ks - $700Ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

4 rating (4 reviews)

Lakes of Mount Dora

$400Ks - $900Ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

4 rating (2 reviews)

Harbor Hills Country Club

$200Ks - $1Ms

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

4.8 rating (6 reviews)

Highland Lakes

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

5 rating (2 reviews)

Bridgewater at Viera

$300Ks - $600Ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

The Country Club of Mount...

$200Ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

4.1 rating (9 reviews)

Indian River Colony Club

$200Ks - $400Ks

Indian River Colony Club, Melbourne, FL

New and Resale | 55+ age-restricted | Built 1986 - present | 777 homes

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Questions? Call us: (888) 625-4885

3.9 rating (7 reviews)

Summit Greens

$300Ks - $400Ks

Summit Greens, Clermont, FL

Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes

5 rating (1 reviews)

Royal Harbor

$200Ks - $400Ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

Lakeside Landings

$200Ks - $500Ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

1 rating (1 reviews)

Sullivan Ranch

$300Ks - $600Ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

Highland Fairways

$100Ks - $300Ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

1 2...3

The Villages®

$355,900

2 beds

2 baths

1,270 sq ft

Villa

1057 CARVER CT, THE VILLAGES, FL, 32163

Community: The Villages®

Harbor Hills Country Club

6128 LANDINGS BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$649,995

3 beds

3 baths

2,134 sq ft

House

6128 LANDINGS BLVD, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

The Villages®

$579,500

3 beds

2 baths

1,939 sq ft

House

2304 FRINGE TREE TRL, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

111 SUGAR MAPLE AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785

$148,000

2 beds

2 baths

1,152 sq ft

Manufactured Home

111 SUGAR MAPLE AVE, WILDWOOD, FL, 34785

Community: The Villages®

Venetian Bay

3367 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$487,000

3 beds

2 baths

1,976 sq ft

Halfplex

3367 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Traditions at Lake Ruby

2920 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$262,500

2 beds

2 baths

1,935 sq ft

House

2920 DAYTON DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Solivita

972 LADERA RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759

$475,000

3 beds

3 baths

2,318 sq ft

House

972 LADERA RANCH RD, KISSIMMEE, FL, 3475...

Community: Solivita

The Villages®

$600,000

3 beds

3 baths

1,911 sq ft

House

4528 HAYWARD PATH, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$609,999

3 beds

2 baths

1,950 sq ft

House

4434 SHOCKOE CIR, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$429,000

3 beds

2 baths

1,724 sq ft

House

669 PEARSON ST, THE VILLAGES, FL, 32162

Community: The Villages®

Stonecrest

11280 SE 170TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$259,900

2 beds

2 baths

1,251 sq ft

House

11280 SE 170TH LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Stonecrest

12607 SE 178TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$315,000

3 beds

2 baths

1,826 sq ft

House

12607 SE 178TH PL, SUMMERFIELD, FL, 3449...

Community: Stonecrest

The Villages®

$495,000

3 beds

2 baths

1,757 sq ft

Villa

1868 DALTON DR, THE VILLAGES, FL, 32162

Community: The Villages®

Huntington at Hunter's Ridge

99 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$499,700

3 beds

2 baths

2,238 sq ft

House

99 HUNTINGTON PL, ORMOND BEACH, FL, 3217...

Community: Huntington at Hunter's Ridge

The Villages®

$925,000

4 beds

2 baths

2,544 sq ft

House

1988 DOVE HOLLOW RUN, THE VILLAGES, FL, ...

Community: The Villages®

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Questions? Call us: (888) 625-4885

Spruce Creek South

9567 SE 174TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$249,999

2 beds

2 baths

1,620 sq ft

House

9567 SE 174TH PLACE RD, SUMMERFIELD, FL,...

Community: Spruce Creek South

Stonecrest

12300 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$485,000

3 beds

2 baths

2,121 sq ft

House

12300 SE 176TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

Spruce Creek South

9885 SE 177TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$215,000

2 beds

2 baths

1,008 sq ft

House

9885 SE 177TH LN, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

Palms at Serenoa

3903 WINGED ELM CT, CLERMONT, FL, 34714, Clermont, FL 34714

$430,000

2 beds

2 baths

1,822 sq ft

House

3903 WINGED ELM CT, CLERMONT, FL, 34714

Community: Palms at Serenoa

The Villages®

$359,000

3 beds

2 baths

1,397 sq ft

Villa

552 AUDREY LN, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

12185 NE 51ST CIR, OXFORD, FL, 34484, Oxford, FL 34484

$329,900

3 beds

2 baths

1,889 sq ft

House

12185 NE 51ST CIR, OXFORD, FL, 34484

Community: The Villages®

The Villages®

$398,000

3 beds

2 baths

1,861 sq ft

House

879 ASTOR WAY, THE VILLAGES, FL, 32162

Community: The Villages®

Twin Lakes

2769 REDBLUSH TER, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772

$524,300

2 beds

3 baths

2,107 sq ft

House

2769 REDBLUSH TER, SAINT CLOUD, FL, 3477...

Community: Twin Lakes

Pelican Bay Daytona Beach

240 BOB WHITE CT # 240, DAYTONA BEACH, F..., Daytona Beach, FL 32119

$205,000

2 beds

2 baths

1,093 sq ft

Condo

240 BOB WHITE CT # 240, DAYTONA BEACH, F...

Community: Pelican Bay Daytona Beach

Pelican Bay Daytona Beach

240 BOB WHITE CT 2400, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$205,000

2 beds

2 baths

1,093 sq ft

Condo

240 BOB WHITE CT 2400, DAYTONA BEACH, FL...

House

4020 CAPLAND AVE, CLERMONT, FL, 34711

Community: Kings Ridge

Venetian Bay

3357 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$499,999

4 beds

3 baths

2,835 sq ft

House

3357 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

Stonecrest

11735 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$439,000

3 beds

2 baths

1,777 sq ft

House

11735 SE 174TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

Foxwood Lake Estates

5038 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810

$229,900

2 beds

2 baths

1,404 sq ft

Manufactured Home

5038 FOXWOOD BLVD, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Four Seasons at Orlando

1855 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$349,990

2 beds

2 baths

1,437 sq ft

Villa

1855 FLORA PASS PL, KISSIMMEE, FL, 34747

House

9673 SE 174TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

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2,487 homes near Winter Park

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Winter Park, FL 55+ active adult communities & homes for sale

90 communities near Winter Park

2,487 homes near Winter Park

2 beds

2 baths

1,270 sq ft

Villa

3 beds

3 baths

2,134 sq ft

House

3 beds

2 baths

1,939 sq ft

House

2 beds

2 baths

1,152 sq ft

Manufactured Home

3 beds

2 baths

1,976 sq ft

Halfplex

2 beds

2 baths

1,935 sq ft

House

3 beds

3 baths

2,318 sq ft

House

3 beds

3 baths

1,911 sq ft

House

3 beds

2 baths

1,950 sq ft

House

3 beds

2 baths

1,724 sq ft

House

2 beds

2 baths

1,251 sq ft

House

3 beds

2 baths

1,826 sq ft

House

3 beds

2 baths

1,757 sq ft

Villa

3 beds

2 baths

2,238 sq ft

House

4 beds

2 baths

2,544 sq ft

House

2 beds

2 baths

1,620 sq ft

House

3 beds

2 baths

2,121 sq ft

House

2 beds

2 baths

1,008 sq ft

House

2 beds

2 baths

1,822 sq ft

House

3 beds