Westport, CT 55+ active adult communities & homes for sale

167 communities near Westport

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3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

2.8 rating (5 reviews)

The Villages NJ

$200Ks - $400Ks

The Villages NJ, Howell, NJ

Resale Only | 55+ age-restricted | Built 1967 - 1975 | 670 homes

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

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4.2 rating (12 reviews)

Surrey Downs

$300Ks - $400Ks

Surrey Downs, Freehold, NJ

Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes

4 rating (1 reviews)

Jefferson Village

$200Ks - $500Ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

2.8 rating (4 reviews)

Cheesequake Village

$200Ks - $300Ks

Cheesequake Village, Old Bridge, NJ

Resale Only | 55+ age-restricted | Built 1965 - 1971 | 713 homes

5 rating (2 reviews)

Shadow Lake Village

$300Ks - $600Ks

Shadow Lake Village, Red Bank, NJ

Resale Only | 55+ age-restricted | Built 1972 - 1980 | 952 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

3.7 rating (3 reviews)

Greenwood Village

<$100k - $200Ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

The Village at Oxford Gre...

$600Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

The Greens at Half Hollow

$600Ks - $1Ms

The Greens at Half Hollow, Melville, NY

Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes

5 rating (2 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

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Questions? Call us: (475) 471-1908

The Waterways at Moriches

$400Ks - $500Ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes

4 rating (8 reviews)

Glenwood Village

$100Ks - $200Ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

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Questions? Call us: (475) 471-1908

Meadowbrook Pointe Athlet...

$600Ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

The Retreat at Carmel

$400Ks - $700Ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Country Pointe Plainview

$1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 homes

Fairview at Oxford Greens

$600Ks - $700Ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

Rivington

$400Ks - $800Ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

5 rating (1 reviews)

Encore Atlantic Shores

$700Ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

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Questions? Call us: (475) 471-1908

Regency at Woodbridge

$600Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

4.9 rating (14 reviews)

Chatfield Farms

$500Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

5 rating (1 reviews)

The Villages at Mount Sin...

$500Ks - $700Ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

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Questions? Call us: (475) 471-1908

Regency at Fishkill

$400Ks - $500Ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

The Seasons at East Meado...

$600Ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

The Bel Aire at East Mead...

$400Ks

The Bel Aire at East Mead..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 95 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

Stone Ridge Estates

$700Ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

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Questions? Call us: (475) 471-1908

Stoneleigh Woods at River...

$500Ks - $600Ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

The Vineyards at Miller P...

$600Ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

3.7 rating (3 reviews)

Rosemont Estates

$700Ks - $800Ks

Rosemont Estates, Marlboro, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 homes

Leisure Knoll

$400Ks - $500Ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

The Manors at The Colony ...

$500Ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

Want to learn more about 55+ rental communities in Westport? 55places can help!

Questions? Call us: (475) 471-1908

Leisure Glen

$400Ks - $500Ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

5 rating (1 reviews)

Westhampton Pines

$1Ms

Westhampton Pines, Westhampton, NY

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes

The Villas at Narraganset...

$500Ks - $600Ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

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

Questions? Call us: (475) 471-1908

Kensington Estates

$2Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

1 2 3 4...5

New The Seasons at East Meadow

169 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$649,900

2 beds

2 baths

1,358 sq ft

Condo

169 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

New Meadowbrook Pointe Athletic Club & Spa

420 PACING WAY, WESTBURY, NY, 11590, Westbury, NY 11590

$679,000

2 beds

2 baths

1,217 sq ft

Condo

420 PACING WAY, WESTBURY, NY, 11590

Community: Meadowbrook Pointe Athletic Club & Spa

New Heritage Village

968 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$249,000

2 beds

2 baths

1,071 sq ft

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Encore Atlantic Shores

236 ENCORE BLVD, EASTPORT, NY, 11941, Eastport, NY 11941

$790,000

2 beds

2 baths

2,185 sq ft

Condo

236 ENCORE BLVD, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

New The Villages NJ

80 PARKWAY DR D, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$439,000

2 beds

2 baths

1,262 sq ft

Ranch

80 PARKWAY DR D, FREEHOLD, NJ, 07728

Community: The Villages NJ

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

Questions? Call us: (475) 471-1908

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Questions? Call us: (475) 471-1908

New Leisure Knoll

475 STRATFORD LN, RIDGE, NY, 11961, Ridge, NY 11961

$519,000

3 beds

2 baths

1,592 sq ft

House

475 STRATFORD LN, RIDGE, NY, 11961

Community: Leisure Knoll

New Glenwood Village

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$245,000

2 beds

2 baths

1,156 sq ft

Manufactured Home

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...

Community: Glenwood Village

New Chatfield Farms

9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0..., Beacon Falls, CT 06403

$515,000

2 beds

3 baths

1,700 sq ft

Condo

9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0...

Community: Chatfield Farms

New Jefferson Village

53 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$439,900

2 beds

2 baths

1,100 sq ft

Condo

53 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

New The Bel Aire at East Meadow

50 MERRICK AVE 120, EAST MEADOW, NY, 115..., East Meadow, NY 11554

$475,000

2 beds

2 baths

1,000 sq ft

Condo

50 MERRICK AVE 120, EAST MEADOW, NY, 115...

Community: The Bel Aire at East Meadow

New The Seasons at East Meadow

286 SPRING DR # 286, EAST MEADOW, NY, 11..., East Meadow, NY 11554

$660,000

2 beds

3 baths

1,030 sq ft

Condo

286 SPRING DR # 286, EAST MEADOW, NY, 11...

Community: The Seasons at East Meadow

New Sonoma Woods

60 SONOMA LN # 60, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$549,900

2 beds

3 baths

2,054 sq ft

Condo

60 SONOMA LN # 60, MIDDLETOWN, CT, 06457

Community: Sonoma Woods

New Rolling Meadows at Wayside

14 MAGNOLIA CT, ASBURY PARK, NJ, 07712, Asbury Park, NJ 07712

$799,900

3 beds

3 baths

2,016 sq ft

House

14 MAGNOLIA CT, ASBURY PARK, NJ, 07712

Community: Rolling Meadows at Wayside

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

Questions? Call us: (475) 471-1908

New Kensington Estates

48 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797

$2,349,999

6 beds

5 baths

4,333 sq ft

House

48 PLAINVIEW RD, WOODBURY, NY, 11797

Community: Kensington Estates

New Heritage Hills

339 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$500,000

2 beds

3 baths

1,550 sq ft

Condo

339 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Want to learn more about 55+ rental communities in Westport? 55places can help!

Questions? Call us: (475) 471-1908

New South Pond Village

162 THISTLE POND DR # 162, BLOOMFIELD, C..., Bloomfield, CT 06002

$395,000

2 beds

2 baths

1,341 sq ft

Condo

162 THISTLE POND DR # 162, BLOOMFIELD, C...

95 FARNWORTH CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

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New The Village at Oxford Greens

117 COUNTRY CLUB DR # 117, OXFORD, CT, 0..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,666 sq ft

117 COUNTRY CLUB DR # 117, OXFORD, CT, 0...

Community: The Village at Oxford Greens

New Cheesequake Village

72 HAVEN DR D, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747

$325,000

2 beds

1 baths

949 sq ft

Condo

72 HAVEN DR D, OLD BRIDGE, NJ, 07747

Community: Cheesequake Village

New Meadowbrook Pointe Athletic Club & Spa

568 PACING WAY # 568, WESTBURY, NY, 1159..., Westbury, NY 11590

$875,000

2 beds

2 baths

1,328 sq ft

Condo

568 PACING WAY # 568, WESTBURY, NY, 1159...

Community: Meadowbrook Pointe Athletic Club & Spa

New Heritage Hills

744 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$619,000

2 beds

2 baths

1,525 sq ft

Condo

744 HERITAGE HLS B, SOMERS, NY, 10589

153 COURS DE PASTEUR E, FREEHOLD, NJ, 07...

Ranch

139 WEIN MARKET C, FREEHOLD, NJ, 07728

Community: The Villages NJ

Want to learn more about 55+ rental communities in Westport? 55places can help!

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Surrey Downs

32 CARNABY CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$324,999

2 beds

1 baths

896 sq ft

Ranch

32 CARNABY CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

Granite Woods

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$229,000

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762

Community: Granite Woods

Regency at Wappinger

61 FARMINGTON RD, WAPPINGERS FALLS, NY, ..., Wappingers Falls, NY 12590

$775,000

2 beds

2 baths

1,738 sq ft

House

61 FARMINGTON RD, WAPPINGERS FALLS, NY, ...

Community: Regency at Wappinger

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

Questions? Call us: (475) 471-1908

Oronoque Village

635 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

3 baths

1,454 sq ft

Condo

635 NORTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

656 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$634,900

2 beds

2 baths

1,296 sq ft

Condo

656 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Frequently Asked Questions

What size 55+ communities are there in Westport?

In Westport, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Westport?

The smallest 55+ community in Westport has 62 homes, the largest has 62 homes, and the average community consists of 62 homes.

Are there gated 55+ communities in Westport?

No, there are no gated 55+ communities in Westport.

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167 communities

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Westport, CT 55+ active adult communities & homes for sale

167 communities near Westport

286 homes near Westport

2 beds

2 baths

1,358 sq ft

Condo

2 beds

2 baths

1,217 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

2 baths

2,185 sq ft

Condo

2 beds

2 baths

1,262 sq ft

Ranch

3 beds

2 baths

1,592 sq ft

House

2 beds

2 baths

1,156 sq ft

Manufactured Home

2 beds

3 baths

1,700 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

3 baths

1,030 sq ft

Condo

2 beds

3 baths

2,054 sq ft

Condo

3 beds

3 baths

2,016 sq ft

House

6 beds

5 baths

4,333 sq ft

House

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,341 sq ft

Condo

2 beds

1 baths

9,140 sq ft

Condo

2 beds

4 baths

2,308 sq ft

Townhouse

2 beds

3 baths

1,666 sq ft

Condo

2 beds