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

2,513 homes near Winter Park

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4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

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

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

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

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

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

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3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 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 (1 reviews)

Plantation Bay Golf &...

$400ks - $2Ms

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

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

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

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

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3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

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

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

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Questions? Call us: (888) 625-4885

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 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 (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

5 rating (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $900ks

Lakes of Mount Dora, Mount Dora, FL

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

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4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

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

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

5 rating (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

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

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $600ks

Cresswind at Victoria Gar..., DeLand, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

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Questions? Call us: (888) 625-4885

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

3.8 rating (5 reviews)

Traditions at Lake Ruby

$200ks - $300ks

Traditions at Lake Ruby, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 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

Tohoqua Reserve

$300ks - $600ks

Tohoqua Reserve, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2021 - present | 258 homes

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

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

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

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Questions? Call us: (888) 625-4885

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

7624 SAND PIERRE CT, KISSIMMEE, FL, 3474...

Community: Four Seasons at Orlando

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New Spruce Creek South

17590 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$189,000

2 beds

2 baths

1,008 sq ft

House

17590 SE 96TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

New Solivita

3461 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$300,000

2 beds

2 baths

1,499 sq ft

Villa

3461 FALLBROOK DR, KISSIMMEE, FL, 34759

Community: Solivita

New Scottish Highlands

27 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$215,000

2 beds

2 baths

1,252 sq ft

House

27 GORDON CT, LEESBURG, FL, 34788

Community: Scottish Highlands

New Plantation at Leesburg

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748

$299,999

3 beds

2 baths

1,868 sq ft

House

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

New Gatherings of Lake Nona

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32..., Orlando, FL 32827

$329,000

2 beds

2 baths

1,549 sq ft

Condo

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

New Grand Haven

20 N VILLAGE PKWY, PALM COAST, FL, 32137, Palm Coast, FL 32137

$750,000

3 beds

3 baths

2,875 sq ft

House

20 N VILLAGE PKWY, PALM COAST, FL, 32137

Community: Grand Haven

New The Villages®

2088 VISION CT, THE VILLAGES, FL, 32163, The Villages, FL 32163

$689,000

3 beds

2 baths

2,013 sq ft

House

2088 VISION CT, THE VILLAGES, FL, 32163

Community: The Villages®

New Foxwood Lake Estates

1704 QUAIL HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$140,000

2 beds

2 baths

1,372 sq ft

Manufactured Home

1704 QUAIL HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

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New The Country Club of Mount Dora

1901 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$539,000

3 beds

2 baths

2,286 sq ft

House

1901 PARK FOREST BLVD, MOUNT DORA, FL, 3...

Community: The Country Club of Mount Dora

New Sullivan Ranch

20926 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757

$349,900

3 beds

2 baths

1,440 sq ft

House

20926 SULLIVAN RANCH BLVD, MOUNT DORA, F...

Community: Sullivan Ranch

New Foxwood Lake Estates

4966 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$174,900

2 beds

2 baths

1,352 sq ft

Manufactured Home

4966 DEERWOOD DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

New Twin Lakes

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772

$420,000

2 beds

2 baths

1,624 sq ft

House

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...

Community: Twin Lakes

New The Villages®

1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$775,000

4 beds

3 baths

2,959 sq ft

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

New Foxwood Lake Estates

1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$164,900

3 beds

2 baths

1,176 sq ft

Manufactured Home

1798 FOX HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

New Four Seasons at Orlando

1999 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$429,980

2 beds

2 baths

1,557 sq ft

Villa

1999 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

New Lakes at Laurel Highlands

2933 IVY LAKE CT, LAKELAND, FL, 33811, Lakeland, FL 33811

$389,500

5 beds

3 baths

2,674 sq ft

House

2933 IVY LAKE CT, LAKELAND, FL, 33811

Community: Lakes at Laurel Highlands

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New The Villages®

5511 HEAD WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163

$394,900

3 beds

2 baths

1,708 sq ft

House

5511 HEAD WAY, THE VILLAGES, FL, 32163

Community: The Villages®

New High Vista at Ridgewood Lakes

116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$309,000

2 beds

2 baths

1,776 sq ft

House

116 FLEMING LN, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

New The Villages®

603 ROBIN LANE AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785

$159,900

2 beds

2 baths

1,352 sq ft

Manufactured Home

603 ROBIN LANE AVE, WILDWOOD, FL, 34785

Community: The Villages®

New The Villages®

1714 EL NINO ST, THE VILLAGES, FL, 32162, The Villages, FL 32162

$289,000

2 beds

2 baths

1,121 sq ft

Villa

1714 EL NINO ST, THE VILLAGES, FL, 32162

Community: The Villages®

New The Villages®

2530 FOXBRIDGE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162

$324,900

3 beds

2 baths

1,392 sq ft

House

2530 FOXBRIDGE TER, THE VILLAGES, FL, 32...

Community: The Villages®

New Plantation Bay Golf & Country Club

608 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$575,000

3 beds

2 baths

2,090 sq ft

House

608 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

New Plantation at Leesburg

25845 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$325,000

3 beds

2 baths

2,047 sq ft

House

25845 GLEN EAGLE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New The Villages®

3284 THEODORE TER, THE VILLAGES, FL, 321..., The Villages, FL 32163

$674,900

3 beds

3 baths

2,033 sq ft

House

3284 THEODORE TER, THE VILLAGES, FL, 321...

Community: The Villages®

New The Villages®

717 TANGERINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$220,000

2 beds

2 baths

1,332 sq ft

Manufactured Home

717 TANGERINE DR, LADY LAKE, FL, 32159

Villa

935 WREN ST, THE VILLAGES, FL, 32163

Community: The Villages®

New Venetian Bay

424 LUNA BELLA LN 416C, NEW SMYRNA BEACH..., New Smyrna Beach, FL 32168

$257,145

2 beds

2 baths

1,669 sq ft

Condo

424 LUNA BELLA LN 416C, NEW SMYRNA BEACH...

Community: Venetian Bay

New Heritage - The Cottages of Sanders Grove

5715 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762

$363,389

4 beds

3 baths

1,938 sq ft

House

5715 HIAWASSEE RD, OKAHUMPKA, FL, 34762

Community: Heritage - The Cottages of Sanders Grove

New Solivita

1405 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759

$279,000

2 beds

2 baths

1,543 sq ft

House

1405 HARBOR RIDGE DR, KISSIMMEE, FL, 347...

Community: Solivita

New Heritage - The Cottages of Sanders Grove

5727 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762

$323,286

3 beds

2 baths

1,407 sq ft

House

5727 HIAWASSEE RD, OKAHUMPKA, FL, 34762

Community: Heritage - The Cottages of Sanders Grove

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

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New Solivita

106 VISTA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$229,900

3 beds

2 baths

1,786 sq ft

House

106 VISTA DR, KISSIMMEE, FL, 34759

Community: Solivita

New Lake Ashton

5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884

$579,900

3 beds

2 baths

2,354 sq ft

House

5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL...

Community: Lake Ashton

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2,513 homes

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

90 communities near Winter Park

2,513 homes near Winter Park

3 beds

2 baths

1,733 sq ft

Villa

3 beds

2 baths

1,505 sq ft

House

4 beds

2 baths

2,069 sq ft

House

2 beds

2 baths

1,148 sq ft

House

2 beds

2 baths

1,437 sq ft

House

2 beds

2 baths

1,008 sq ft

House

2 beds

2 baths

1,499 sq ft

Villa

2 beds

2 baths

1,252 sq ft

House

3 beds

2 baths

1,868 sq ft

House

2 beds

2 baths

1,549 sq ft

Condo

3 beds

3 baths

2,875 sq ft

House

3 beds

2 baths

2,013 sq ft

House

2 beds

2 baths

1,372 sq ft

Manufactured Home

3 beds

2 baths

2,286 sq ft

House

3 beds

2 baths

1,440 sq ft

House

2 beds

2 baths

1,352 sq ft

Manufactured Home

2 beds

2 baths

1,624 sq ft

House

4 beds

3 baths

2,959 sq ft

House

3 beds

2 baths

1,176 sq ft

Manufactured Home

2 beds