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

131 communities near Cheshire

Sort by:

Relevance

3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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

Questions? Call us: (475) 244-9781

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

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

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)

The Villages at Mount Sin...

$600ks

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

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

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

Questions? Call us: (475) 244-9781

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

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

Questions? Call us: (475) 244-9781

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

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

Questions? Call us: (475) 244-9781

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

11 MORLEY CIR, HUNTINGTON, NY, 11747

Community: The Coves at Melville

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

Questions? Call us: (475) 244-9781

New Leisure Village

133 EASTBOURNE CT F, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$349,000

2 beds

1 baths

836 sq ft

Condo

133 EASTBOURNE CT F, BROOKHAVEN, NY, 119...

Community: Leisure Village

New Sunken Pond Estates

2803 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$499,000

2 beds

3 baths

1,350 sq ft

Condo

2803 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

New Heritage Village

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

$414,900

2 beds

2 baths

1,432 sq ft

Condo

945 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Vineyards at Brookfield

104 ARI LN, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$879,000

2 beds

4 baths

2,718 sq ft

Condo

104 ARI LN, BROOKHAVEN, NY, 11934

Community: Vineyards at Brookfield

New Stone Ridge Estates

160 CHRISTINE DR, HUNTINGTON, NY, 11746, Huntington, NY 11746

2 beds

2 baths

2,008 sq ft

567 INVERNESS CT 567, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (475) 244-9781

New The Powder Forest Homes

15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070

$949,000

4 beds

3 baths

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Country Pointe Plainview

82101 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$2,398,000

3 beds

4 baths

2,697 sq ft

House

82101 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

New Oronoque Village

283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$625,000

2 beds

3 baths

1,415 sq ft

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

New The Greens at Half Hollow

517 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,275,000

2 beds

3 baths

2,000 sq ft

Condo

517 BARDINI DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New The Greens at Half Hollow

283 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,395,000

3 beds

3 baths

2,700 sq ft

Condo

283 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New The Seasons at Elwood

35 WINTER PL, HUNTINGTON, NY, 11731, Huntington, NY 11731

$949,000

2 beds

3 baths

1,500 sq ft

Condo

35 WINTER PL, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New Encore Atlantic Shores

176 MELODY CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$899,000

2 beds

3 baths

2,800 sq ft

Condo

176 MELODY CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

New Overlook

1001 COTTAGE DR 1, CARMEL, NY, 10512, Carmel, NY 10512

$1,250,000

2 beds

4 baths

2,900 sq ft

Condo

1001 COTTAGE DR 1, CARMEL, NY, 10512

Community: Overlook

New The Waterways at Moriches

605 BAY VIEW CIR 5, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$649,000

2 beds

3 baths

1,485 sq ft

Condo

605 BAY VIEW CIR 5, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

New Meadow Brook Estates

211 MEADOW BROOK RD 211, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

3 beds

3 baths

2,201 sq ft

Condo

211 MEADOW BROOK RD 211, OXFORD, CT, 064...

Community: Meadow Brook Estates

New Heritage Village

10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$364,000

3 beds

2 baths

1,716 sq ft

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488

Condo

59 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

Oronoque Village

93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$559,000

2 beds

3 baths

2,542 sq ft

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Westhampton Pines

112 ASHLEY, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$1,225,000

3 beds

3 baths

2,304 sq ft

Condo

112 ASHLEY, SOUTHAMPTON, NY, 11977

Community: Westhampton Pines

Frequently Asked Questions

What size 55+ communities are there in Cheshire?

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

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

The smallest 55+ community in Cheshire has 88 homes, the largest has 88 homes, and the average community consists of 88 homes.

Are there gated 55+ communities in Cheshire?

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

Want more information about active adult communities around Cheshire?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Cheshire?

Call us: (475) 244-9781

131 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Jun 18, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

131 communities near Cheshire

263 homes near Cheshire

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

3 baths

1,558 sq ft

Condo

2 beds

2 baths

1,450 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

2 beds

2 baths

1,109 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

4 baths

2,718 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,261 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

4 baths

2,388 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

2 baths

2,008 sq ft

4 beds

3 baths

1,878 sq ft

3 beds

4 baths

2,697 sq ft

House

2 beds

3 baths

1,415 sq ft

Condo

2 beds

3 baths

2,000 sq ft

Condo