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

254 homes 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

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

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

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

Questions? Call us: (475) 244-9781

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

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

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.

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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

Questions? Call us: (475) 244-9781

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

$300ks - $500ks

Fairfield at St. James, St. James, NY

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

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

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

Questions? Call us: (475) 244-9781

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes

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

Questions? Call us: (475) 244-9781

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

1 2 3...4

Sunken Pond Estates

3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$499,000

2 beds

2 baths

1,587 sq ft

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

The Greens at Half Hollow

928 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$615,000

2 beds

2 baths

1,262 sq ft

Condo

928 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Oronoque Village

72 DAKOTA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$539,500

1 beds

3 baths

1,118 sq ft

Condo

72 DAKOTA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

71 DAKOTA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$425,000

1 beds

2 baths

1,375 sq ft

Condo

71 DAKOTA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$520,000

3 beds

2 baths

1,716 sq ft

Condo

977 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

731 CHAMPIONSHIP DR 731, OXFORD, CT, 064..., Oxford, CT 06478

$629,900

2 beds

2 baths

1,539 sq ft

Condo

731 CHAMPIONSHIP DR 731, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Jefferson Village

18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598

$395,000

2 beds

1 baths

1,000 sq ft

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598

Community: Jefferson Village

Country Pointe Preserve

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$965,000

2 beds

3 baths

2,389 sq ft

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

Heritage Village

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

$214,900

2 beds

2 baths

1,032 sq ft

Condo

151 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

Heritage Village

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

$229,000

1 beds

1 baths

928 sq ft

Condo

79 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

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

Community: Greenwood Village

Greenwood Village

43 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$264,999

2 beds

2 baths

1,164 sq ft

Condo

43 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Village

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,308 sq ft

Condo

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Community: Leisure Village

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

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

Fairfield at St. James

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

$599,999

3 beds

3 baths

1,716 sq ft

Condo

506 DREW DR, SMITHTOWN, NY, 11780

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480

Community: Bartlett Hill

Oronoque Village

639 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$629,000

2 beds

3 baths

1,438 sq ft

Condo

639 ONONDAGA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

26 DORSET CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

Leisure Knoll

506 LANCASTER CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,000

2 beds

2 baths

1,394 sq ft

House

506 LANCASTER CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Hills

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

$979,000

3 beds

2 baths

1,793 sq ft

Condo

392 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

3 baths

1,479 sq ft

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

65A VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$134,900

1 beds

1 baths

864 sq ft

Condo

65A VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (475) 244-9781

Overlook

3004 EASTVIEW DR 105, CARMEL, NY, 10512, Carmel, NY 10512

$722,000

2 beds

3 baths

2,040 sq ft

Condo

3004 EASTVIEW DR 105, CARMEL, NY, 10512

Community: Overlook

Overlook

2031 SUMMIT LOOP 89, CARMEL, NY, 10512, Carmel, NY 10512

$789,000

2 beds

2 baths

1,948 sq ft

Condo

2031 SUMMIT LOOP 89, CARMEL, NY, 10512

Community: Overlook

1 2 3 4 5 6…7

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

254 homes

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: Apr 11, 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 - Page 3

130 communities near Cheshire

254 homes near Cheshire

2 beds

2 baths

1,587 sq ft

Condo

3 beds

3 baths

2,243 sq ft

Condo

2 beds

2 baths

2,008 sq ft

Condo

2 beds

2 baths

1,064 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,262 sq ft

Condo

1 beds

3 baths

1,118 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,539 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

3 baths

2,389 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

1 baths

1,245 sq ft

Condo

2 beds

2 baths

1,110 sq ft

Condo

2 beds

2 baths

1,164 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

1 baths

874 sq ft

Condo

2 beds