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

168 communities near Westport

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3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

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

2.8 rating (5 reviews)

The Villages NJ

$200ks - $300ks

The Villages NJ, Howell, NJ

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

3 rating (2 reviews)

Heritage Hills

$400ks - $1Ms

Heritage Hills, Somers, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

5 rating (2 reviews)

Fairfield at St. James

$300ks - $500ks

Fairfield at St. James, St. James, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

4.2 rating (12 reviews)

Surrey Downs

$200ks - $300ks

Surrey Downs, Freehold, NJ

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

2.8 rating (4 reviews)

Cheesequake Village

$100ks - $200ks

Cheesequake Village, Old Bridge, NJ

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

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Questions? Call us: (475) 471-1908

The Village at Oxford Gre...

$400ks - $500ks

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

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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Questions? Call us: (475) 471-1908

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

5 rating (1 reviews)

Four Seasons at Great Not...

$400ks - $700ks

Four Seasons at Great Not..., Woodland Park, NJ

Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

3.7 rating (3 reviews)

Rosemont Estates

$500ks - $700ks

Rosemont Estates, Marlboro, NJ

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

5 rating (2 reviews)

Shadow Lake Village

$200ks - $500ks

Shadow Lake Village, Red Bank, NJ

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

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Questions? Call us: (475) 471-1908

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Chelsea Square

$300ks - $400ks

Chelsea Square, Morganville, NJ

New and Resale | 55+ age-restricted | Built 2007 - present | 225 homes

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Questions? Call us: (475) 471-1908

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

The Seasons at East Meado...

$400ks - $600ks

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

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

The Manors at The Colony ...

$300ks - $400ks

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

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

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

Questions? Call us: (475) 471-1908

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Four Seasons at Wayne

$300ks - $400ks

Four Seasons at Wayne, Wayne, NJ

Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Glassbury Court at Cold S...

$500ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

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

Questions? Call us: (475) 471-1908

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

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

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

Regency at Holmdel

$900ks - $1Ms

Regency at Holmdel, Holmdel, NJ

Resale Only | 55+ age-restricted | Built 2016 - 2019 | 181 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

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

Questions? Call us: (475) 471-1908

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

1 2 3 4...5

New Village Estates

137 FRANCESCA WAY, BABYLON, NY, 11701, Babylon, NY 11701

$599,999

2 beds

1 baths

1,245 sq ft

Condo

137 FRANCESCA WAY, BABYLON, NY, 11701

Community: Village Estates

New Greenwood Village

75 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$135,000

2 beds

2 baths

1,110 sq ft

Condo

75 VILLAGE CIR, BROOKHAVEN, NY, 11949

233 GLEN DR 233, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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 Four Seasons at Great Notch Spa and Club

8 QUARTZ WAY, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424

$800,000

2 beds

2 baths

1,781 sq ft

8 QUARTZ WAY, WOODLAND PARK, NJ, 07424

Community: Four Seasons at Great Notch Spa and Club

New Heritage Hills

441 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$539,000

2 beds

2 baths

1,265 sq ft

Condo

Community: Heritage Village

New Rolling Meadows at Wayside

250 ROLLING MEADOWS BLVD, OCEAN TWP, NJ,..., Ocean Twp, NJ 07712

$849,000

3 beds

4 baths

2,440 sq ft

House

250 ROLLING MEADOWS BLVD, OCEAN TWP, NJ,...

Community: Rolling Meadows at Wayside

New Leisure Village

395 WOODBRIDGE DR C, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$289,000

2 beds

1 baths

874 sq ft

Condo

395 WOODBRIDGE DR C, BROOKHAVEN, NY, 119...

Community: Leisure Village

New Leisure Village

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$380,000

2 beds

2 baths

972 sq ft

Condo

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196...

Community: Leisure Village

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Questions? Call us: (475) 471-1908

New Country Village Estates

58 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$449,000

2 beds

2 baths

1,386 sq ft

Condo

58 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

New Fairfield at St. James

506 DREW DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$625,000

3 beds

3 baths

1,716 sq ft

Condo

506 DREW DR, SMITHTOWN, NY, 11780

Condo

4 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

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Heritage Village

78 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$280,000

2 beds

2 baths

1,032 sq ft

Condo

78 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Rolling Meadows at Wayside

99 BARBERRY DR, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712

$834,900

2 beds

3 baths

2,168 sq ft

Adult Community

99 BARBERRY DR, OCEAN TWP, NJ, 07712

Community: Rolling Meadows at Wayside

The Villages at Mount Sinai Park

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$799,000

3 beds

3 baths

2,455 sq ft

Condo

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Rivington

424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810

$510,000

2 beds

2 baths

1,258 sq ft

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...

Community: Rivington

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

Questions? Call us: (475) 471-1908

Bartlett Hill

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480

$479,900

2 beds

3 baths

1,404 sq ft

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480

Community: Bartlett Hill

Meadowbrook Pointe Links & Spa

83 PACIFIC DUNES CT 83, BROOKHAVEN, NY, ..., Brookhaven, NY 11763

$749,990

3 beds

3 baths

2,047 sq ft

Condo

83 PACIFIC DUNES CT 83, BROOKHAVEN, NY, ...

Community: Meadowbrook Pointe Links & Spa

HarborView

$825,000

2 beds

3 baths

Condo

100 HARBOR VIEW DR 111, NORTH HEMPSTEAD,...

Community: HarborView

Leisure Glen

263 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,315 sq ft

Condo

263 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Stoneleigh Woods at Riverhead

153 STONELEIGH DR 153, RIVERHEAD, NY, 11..., Riverhead, NY 11901

$699,000

3 beds

3 baths

2,107 sq ft

Condo

153 STONELEIGH DR 153, RIVERHEAD, NY, 11...

Community: Stoneleigh Woods at Riverhead

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

Questions? Call us: (475) 471-1908

Strathmore Gate East

25 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$329,000

1 beds

1 baths

750 sq ft

Condo

25 FREEMONT LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

The Greens at Half Hollow

236 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,698,000

2 beds

3 baths

2,500 sq ft

Condo

236 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Regency at Holmdel

31 LANGTON DR, HOLMDEL, NJ, 07733, Holmdel, NJ 07733

$1,429,000

3 beds

4 baths

3,304 sq ft

Townhouse

31 LANGTON DR, HOLMDEL, NJ, 07733

Community: Regency at Holmdel

Heritage Hills

358 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$622,900

2 beds

3 baths

1,550 sq ft

Condo

358 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Glen

415 LEISURE DR 415, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$642,000

2 beds

2 baths

1,867 sq ft

Condo

415 LEISURE DR 415, BROOKHAVEN, NY, 1196...

133A RIGI STRASSE, FREEHOLD, NJ, 07728

Community: The Villages NJ

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

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Fairfield at St. James

908 DREW LN, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$609,000

2 beds

2 baths

1,050 sq ft

Condo

908 DREW LN, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Chelsea Square

115 BECKET WAY, MORGANVILLE, NJ, 07751, Morganville, NJ 07751

$480,000

2 beds

2 baths

Adult Community

115 BECKET WAY, MORGANVILLE, NJ, 07751

Community: Chelsea Square

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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168 communities

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

168 communities near Westport

307 homes near Westport

2 beds

1 baths

1,245 sq ft

Condo

2 beds

2 baths

1,110 sq ft

Condo

1 beds

1 baths

708 sq ft

Condo

2 beds

2 baths

1,164 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,781 sq ft

2 beds

2 baths

1,265 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

3 baths

2,551 sq ft

House

2 beds

2 baths

1,076 sq ft

Condo

3 beds

4 baths

2,440 sq ft

House

2 beds

1 baths

874 sq ft

Condo

2 beds

2 baths

972 sq ft

Condo

2 beds

2 baths

1,386 sq ft

Condo

3 beds

3 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

3 baths

2,734 sq ft

Condo

2 beds

3 baths

2,823 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

2 beds

2 baths