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

172 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 (4 reviews)

Cheesequake Village

$200ks - $300ks

Cheesequake Village, Old Bridge, NJ

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

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

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Questions? Call us: (475) 471-1908

4 rating (1 review)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

5 rating (2 reviews)

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

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.

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

4.2 rating (12 reviews)

Surrey Downs

$200ks - $300ks

Surrey Downs, Freehold, NJ

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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

Questions? Call us: (475) 471-1908

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 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 (1 review)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

HarborView

$600ks - $800ks

HarborView, Port Washington, NY

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

5 rating (1 review)

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

5 rating (1 review)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

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

Questions? Call us: (475) 471-1908

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

1 rating (1 review)

Plymouth Estates at Mount...

$400ks - $500ks

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

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

Four Seasons at Colts Far...

$600ks - $800ks

Four Seasons at Colts Far..., Farmingdale, NJ

New Construction | 55+ age-restricted | Built 2021 - present | 111 homes

The Vineyards at Miller P...

$500ks

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

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

Apple Ridge

$500ks - $1Ms

Apple Ridge, Mahwah, NJ

Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes

5 rating (1 review)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

5 rating (1 review)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

Rolling Meadows at Waysid...

$500ks - $600ks

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

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

5 rating (1 review)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

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

Questions? Call us: (475) 471-1908

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

39 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (475) 471-1908

The Villages NJ

41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077..., Freehold, NJ 07728

$389,000

2 beds

2 baths

1,008 sq ft

Ranch

41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077...

Community: The Villages NJ

New Surrey Downs

39 CARNABY CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$335,000

2 beds

1 baths

896 sq ft

Ranch

39 CARNABY CLOSE, FREEHOLD, NJ, 07728

1220 WILLOW LN 1219, HEMPSTEAD, NY, 1158...

Community: Dutchgate

New Apple Ridge

86 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430

$950,000

3 beds

3 baths

Condo

86 FISHER RD, MAHWAH, NJ, 07430

Community: Apple Ridge

New Oronoque Village

161 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$575,000

2 beds

3 baths

1,426 sq ft

Condo

Community: Chatfield Farms

New Saddle Lakes

176 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$575,000

2 beds

2 baths

1,247 sq ft

Condo

176 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

New Pond Spring Village

127 PONDVIEW CIR 127, BEACON FALLS, CT, ..., Beacon Falls, CT 06403

$465,000

2 beds

3 baths

1,328 sq ft

Condo

127 PONDVIEW CIR 127, BEACON FALLS, CT, ...

Community: Pond Spring Village

New Glenwood Village

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$289,000

2 beds

2 baths

1,248 sq ft

Manufactured Home

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1...

Community: Glenwood Village

New Leisure Glen

8 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$559,000

2 beds

2 baths

1,212 sq ft

Condo

8 FLANDERS CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Jefferson Village

36 SUSSEX DR A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$350,000

1 beds

1 baths

725 sq ft

Condo

36 SUSSEX DR A, YORKTOWN, NY, 10598

Community: Jefferson Village

New Rolling Meadows at Wayside

3 MORNING GLORY DR, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712

$924,900

4 beds

4 baths

2,016 sq ft

Adult Community

3 MORNING GLORY DR, OCEAN TWP, NJ, 07712

Community: Rolling Meadows at Wayside

New The Villas at Jumping Brook

18 TALL PINES DR, NEPTUNE TOWNSHIP, NJ, ..., Neptune Township, NJ 07753

$729,000

2 beds

2 baths

1,742 sq ft

Ranch

18 TALL PINES DR, NEPTUNE TOWNSHIP, NJ, ...

Community: The Villas at Jumping Brook

New Heritage Hills

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

$520,000

2 beds

2 baths

1,435 sq ft

Condo

343 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Cheesequake Village

11 IOWA CT 617, MATAWAN, NJ, 07747, Matawan, NJ 07747

$350,000

2 beds

2 baths

976 sq ft

Adult Community

11 IOWA CT 617, MATAWAN, NJ, 07747

Community: Cheesequake Village

New Long Hill Village

36 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$525,000

2 beds

2 baths

1,370 sq ft

Condo

36 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

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

Questions? Call us: (475) 471-1908

New Encore at Lake Grove

9 SONATA CT, SMITHTOWN, NY, 11755, Smithtown, NY 11755

$599,000

2 beds

2 baths

1,685 sq ft

Condo

9 SONATA CT, SMITHTOWN, NY, 11755

Community: Encore at Lake Grove

New The Villages NJ

32 PLAZA DE LAS LOBOS C, FREEHOLD, NJ, 0..., Freehold, NJ 07728

$399,000

2 beds

2 baths

1,008 sq ft

Adult Community

32 PLAZA DE LAS LOBOS C, FREEHOLD, NJ, 0...

Community: The Villages NJ

New Cheesequake Village

11 IOWA CT 617, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747

$350,000

2 beds

2 baths

976 sq ft

Townhouse,Single Family Residence

11 IOWA CT 617, OLD BRIDGE, NJ, 07747

Community: Cheesequake Village

New Plymouth Estates at Mount Sinai

53 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$499,999

2 beds

2 baths

1,272 sq ft

Condo

53 ROSE LN, BROOKHAVEN, NY, 11766

Community: Plymouth Estates at Mount Sinai

New Sunken Pond Estates

1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$545,000

2 beds

2 baths

1,258 sq ft

Condo

1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

New Heritage Hills

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

$699,000

2 beds

2 baths

1,427 sq ft

Condo

39 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Greenwood Village

33A LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$144,999

2 beds

1 baths

800 sq ft

House

33A LIMETREE DR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Glenwood Village

1661 OLD COUNTRY RD 291, RIVERHEAD, NY, ..., Riverhead, NY 11901

$259,000

2 beds

2 baths

1,200 sq ft

Mobile Home

1661 OLD COUNTRY RD 291, RIVERHEAD, NY, ...

Community: Glenwood Village

New Woodridge Strathmore Terrace

74 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$549,990

2 beds

2 baths

1,240 sq ft

Condo

74 HEARTHSIDE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Woodridge Strathmore Terrace

9 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$439,000

2 beds

2 baths

1,240 sq ft

Condo

9 CHIPPENDALE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Rivington

79 WINDING RIDGE WAY 79, DANBURY, CT, 06..., Danbury, CT 06810

$1,112,000

3 beds

4 baths

2,596 sq ft

Condo

79 WINDING RIDGE WAY 79, DANBURY, CT, 06...

Community: Rivington

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

Questions? Call us: (475) 471-1908

Heritage Hills

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

$829,000

3 beds

2 baths

1,780 sq ft

Condo

254 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Spring Lake Village

261 CARRIAGE DR 261, SOUTHINGTON, CT, 06..., Southington, CT 06489

$375,000

2 beds

2 baths

1,207 sq ft

Condo

261 CARRIAGE DR 261, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

Frequently Asked Questions

What size 55+ communities are there in Westport?

Of the 1 55+ community in Westport, it is for sale. By size, 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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172 communities

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

172 communities near Westport

400 homes near Westport

2 beds

2 baths

1,123 sq ft

Condo

2 beds

2 baths

1,592 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,078 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,008 sq ft

Ranch

2 beds

1 baths

896 sq ft

Ranch

1 beds

3 baths

2,660 sq ft

Condo

2 beds

2 baths

1,313 sq ft

Condo

2 beds

2 baths

1,124 sq ft

Adult Community

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

3 beds

3 baths

Condo

2 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

976 sq ft

Adult Community

2 beds

2 baths

976 sq ft

Condo

2 beds

3 baths

2,184 sq ft

Condo

2 beds

2 baths

1,247 sq ft

Condo

2 beds

3 baths

1,328 sq ft

Condo

2 beds

2 baths