Westport, CT 55+ active adult communities & homes for sale - Page 3

369 homes 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 (4 reviews)

Cheesequake Village

$100ks - $200ks

Cheesequake Village, Old Bridge, NJ

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

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

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

Questions? Call us: (475) 471-1908

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

4.2 rating (12 reviews)

Surrey Downs

$200ks - $300ks

Surrey Downs, Freehold, NJ

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

Questions? Call us: (475) 471-1908

The Manors at The Colony ...

$300ks - $400ks

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

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Rolling Meadows at Waysid...

$500ks - $600ks

Rolling Meadows at Waysid..., Ocean Township, NJ

Resale Only | 55+ age-restricted | Built 2002 - 2007 | 328 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

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

Questions? Call us: (475) 471-1908

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes

4.6 rating (9 reviews)

Meadowbrook Pointe Links ...

$300ks - $700ks

Meadowbrook Pointe Links ..., Medford, NY

New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes

5 rating (1 reviews)

The Villas at Jumping Bro...

$300ks - $500ks

The Villas at Jumping Bro..., Neptune Township, NJ

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 168 homes

Equestra at Colts Neck Cr...

$600ks - $700ks

Equestra at Colts Neck Cr..., Farmingdale, NJ

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 483 homes

HarborView

$800ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

Winthrop Court

$400ks - $600ks

Winthrop Court, Clifton, NJ

Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 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

Glassbury Court at Cold S...

$500ks - $700ks

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...

Community: Glassbury Court at Cold Spring

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

Questions? Call us: (475) 471-1908

Four Seasons at Cedar Grove

505 HOLLY LN, CEDAR GROVE TWP., NJ, 0700..., Cedar Grove Twp., NJ 07009

$799,000

2 beds

2 baths

505 HOLLY LN, CEDAR GROVE TWP., NJ, 0700...

Community: Four Seasons at Cedar Grove

Heritage Village

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

$449,000

2 beds

2 baths

1,432 sq ft

Condo

818 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Cheesequake Village

5 PENNSYLVANIA DR, OLD BRIDGE TWP., NJ, ..., Old Bridge Twp., NJ 07747

2 baths

1,398 sq ft

Condo

233 HERITAGE VLG A, SOUTHBURY, CT, 06488

100 HARBORVIEW DR 301, NORTH HEMPSTEAD, ...

Community: HarborView

Heritage Village

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

$375,000

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478

2 beds

2 baths

1,557 sq ft

Condo

33 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

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

Questions? Call us: (475) 471-1908

Cheesequake Village

11 INDIANA CT A, MATAWAN, NJ, 07747, Matawan, NJ 07747

1 beds

1 baths

949 sq ft

Adult Community

1 ALABAMA CT 820, MATAWAN, NJ, 07747

606 FLAIR CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

Questions? Call us: (475) 471-1908

Oronoque Village

46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Vineyards at Moriches

20 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$759,000

2 beds

3 baths

1,984 sq ft

Condo

20 EMILIE DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

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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.

How long do listings in 55+ communities in Westport typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in Westport stay on the market for around 19 days. The average price of homes for sale in this community is approximately $459,000, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Whitney Glen average around $459,000.

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369 homes

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REIN updates its listings on a daily basis. Data last updated: Jul 27, 2026.
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Westport, CT 55+ active adult communities & homes for sale - Page 3

170 communities near Westport

369 homes near Westport

2 beds

2 baths

1,071 sq ft

Condo

2 beds

2 baths

1,261 sq ft

House

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,747 sq ft

Condo

2 beds

2 baths

1,974 sq ft

Condo

2 beds

2 baths

2 beds

2 baths

1,432 sq ft

Condo

2 beds

1 baths

2 beds

2 baths

1,250 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

3 beds

3 baths

2,246 sq ft

Condo

2 beds

2 baths

980 sq ft

Manufactured Home

2 beds

2 baths

1,567 sq ft

Ranch

2 beds

2 baths

1,328 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

3 beds

2 baths

2,008 sq ft

Condo

2 beds

2 baths

1,186 sq ft

Condo

2 beds

2 baths

1,265 sq ft

Condo

3 beds