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

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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

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

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

8923 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

House

130 PRIMA DR, KISSIMMEE, FL, 34759

13175 SE 94TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

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

Questions? Call us: (888) 625-4885

The Villages®

$625,000

3 beds

2 baths

1,806 sq ft

House

1945 RIEGER RD, THE VILLAGES, FL, 32163

Community: The Villages®

Esplanade at Highland Ranch

2605 CLEMSON RIDGE CT, CLERMONT, FL, 347..., Clermont, FL 34715

$438,999

2 beds

2 baths

1,726 sq ft

House

2605 CLEMSON RIDGE CT, CLERMONT, FL, 347...

Community: Esplanade at Highland Ranch

Trilogy® Orlando

602 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736

$589,999

2 beds

3 baths

1,900 sq ft

House

602 CONSERVATION BLVD, GROVELAND, FL, 34...

Community: Trilogy® Orlando

Solivita

308 VESTRELLA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$285,000

2 beds

2 baths

1,703 sq ft

House

308 VESTRELLA DR, KISSIMMEE, FL, 34759

Community: Solivita

Stonecrest

17680 SE 121ST CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$253,600

2 beds

2 baths

1,581 sq ft

House

17680 SE 121ST CT, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Traditions at Lake Ruby

3986 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$415,000

4 beds

3 baths

2,320 sq ft

House

3986 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Breakaway Trails

4 CREEK BEND WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$695,000

5 beds

3 baths

3,625 sq ft

House

4 CREEK BEND WAY, ORMOND BEACH, FL, 3217...

Community: Breakaway Trails

Breakaway Trails

2 CREEK BEND WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$655,000

4 beds

4 baths

3,098 sq ft

House

2 CREEK BEND WAY, ORMOND BEACH, FL, 3217...

Community: Breakaway Trails

The Villages®

$589,000

3 beds

2 baths

1,678 sq ft

House

512 AINSWORTH CIR, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$424,900

3 beds

2 baths

2,044 sq ft

House

1422 SEGOVIA PL, THE VILLAGES, FL, 32162

Community: The Villages®

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The Villages®

1708 LAUREN LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$234,900

2 beds

2 baths

1,040 sq ft

Manufactured Home

1708 LAUREN LN, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$199,999

1 beds

1 baths

793 sq ft

Villa

706 VILLITA LN, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$235,000

2 beds

2 baths

1,156 sq ft

Villa

2907 BARBOZA DR, THE VILLAGES, FL, 32162

Community: The Villages®

Halifax Plantation

1452 KILRUSH DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$719,000

4 beds

2 baths

2,613 sq ft

House

1452 KILRUSH DR, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

Solivita

428 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$419,900

2 beds

2 baths

2,023 sq ft

House

428 BEL AIR WAY, KISSIMMEE, FL, 34759

Community: Solivita

Pennbrooke Fairways

738 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$142,900

1 beds

1 baths

588 sq ft

House

738 COTTAGE PARK LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Four Seasons at Orlando

1980 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$595,000

3 beds

2 baths

2,202 sq ft

House

1980 FLORA PASS PL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

The Villages®

$359,900

2 beds

2 baths

1,146 sq ft

Villa

1402 CONCHAS DR, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$379,900

3 beds

2 baths

1,855 sq ft

House

17979 SE 89TH ROTHWAY CT, THE VILLAGES, ...

Community: The Villages®

New Bridgewater at Viera

9273 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$495,000

3 beds

2 baths

1,900 sq ft

House

9273 ALISTER DR, MELBOURNE, FL, 32940

House

4156 NADIRA CT, THE VILLAGES, FL, 32163

Community: The Villages®

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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

3 beds

3 baths

2,038 sq ft

House

3 beds

2 baths

1,786 sq ft

House

3 beds

2 baths

1,554 sq ft

Villa

2 beds

2 baths

1,134 sq ft

Manufactured Home

3 beds

2 baths

1,926 sq ft

House

2 beds

2 baths

1,351 sq ft

Villa

3 beds

2 baths

1,490 sq ft

House

3 beds

2 baths

2,805 sq ft

House

3 beds

2 baths

2,141 sq ft

House

2 beds

2 baths

1,106 sq ft

House

2 beds

2 baths

1,406 sq ft

House

2 beds

2 baths

1,404 sq ft

House

3 beds

2 baths

2,021 sq ft

House

3 beds

2 baths

1,725 sq ft

House

3 beds

3 baths

2,339 sq ft

House

3 beds

2 baths

1,806 sq ft

House

2 beds

2 baths

1,726 sq ft

House

2 beds

3 baths

1,900 sq ft

House

2 beds

2 baths

1,703 sq ft

House

2 beds