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

130 communities near Cheshire

Sort by:

Relevance

O'Meara Farm

$400ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

The Coach Homes at Ridgef...

$300ks - $400ks

The Coach Homes at Ridgef..., Ridgefield, CT

New Construction | 55+ age-restricted | Built 2019 - present | 30 homes

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

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

Questions? Call us: (475) 244-9781

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 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.

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

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

Questions? Call us: (475) 244-9781

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

New Construction | 55+ age-restricted | Built 2014 - present | 16 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

Autumn Estates

$500ks - $600ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

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

Questions? Call us: (475) 244-9781

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

The Club at Melville

$500ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

4 rating (1 reviews)

Vineyards at Blue Point

$500ks - $700ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

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

Questions? Call us: (475) 244-9781

The Bel Aire at East Mead...

$300ks - $400ks

The Bel Aire at East Mead..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 95 homes

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

1 2 3...4

New Dutchgate

205 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580

$699,999

3 beds

2 baths

1,480 sq ft

Condo

205 WILLOW LN, HEMPSTEAD, NY, 11580

Community: Dutchgate

New Heritage Hills

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

$679,999

2 beds

2 baths

1,416 sq ft

Condo

386 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Jefferson Village

185 LONG HILL DR A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$449,000

2 beds

2 baths

1,302 sq ft

Condo

185 LONG HILL DR A, YORKTOWN, NY, 10598

Community: Jefferson Village

New The Village at Buckingham

18 CAVENDISH PL 18, AVON, CT, 06001, Avon, CT 06001

$714,900

3 beds

3 baths

2,730 sq ft

Condo

18 CAVENDISH PL 18, AVON, CT, 06001

Community: The Village at Buckingham

New Jefferson Village

23 DORSET CT C, YORKTOWN, NY, 10598, Yorktown, NY 10598

$339,000

1 beds

1 baths

700 sq ft

Condo

23 DORSET CT C, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (475) 244-9781

New Meadow Brook Estates

223 MEADOW BROOK RD 223, OXFORD, CT, 064..., Oxford, CT 06478

$589,900

2 beds

2 baths

1,480 sq ft

Condo

223 MEADOW BROOK RD 223, OXFORD, CT, 064...

Community: Meadow Brook Estates

New Greenwood Village

40 WILLOW CT, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$249,999

2 beds

2 baths

1,151 sq ft

Manufactured On Land

40 WILLOW CT, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Oronoque Village

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

$550,000

2 beds

3 baths

1,620 sq ft

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

New Woodridge Strathmore Terrace

54 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$549,999

2 beds

2 baths

1,335 sq ft

Condo

54 STANDISH DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Heritage Village

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

$479,000

2 beds

2 baths

1,432 sq ft

Condo

899 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

1 beds

3 baths

1,438 sq ft

Condo

209 ACORN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Vineyards at Brookfield

69 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$709,999

2 beds

3 baths

2,254 sq ft

Condo

69 AVERY DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Brookfield

New The Powder Forest Homes

9 ASHTON CIR, SIMSBURY, CT, 06070, Simsbury, CT 06070

$700,000

2 beds

2 baths

1,809 sq ft

Condo

9 ASHTON CIR, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Applegate Estates

90 APPLE GATE 190, SOUTHINGTON, CT, 0648..., Southington, CT 06489

$450,000

2 beds

2 baths

1,350 sq ft

Condo

90 APPLE GATE 190, SOUTHINGTON, CT, 0648...

Community: Applegate Estates

New The Greens at Half Hollow

1153 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$750,000

2 beds

2 baths

1,100 sq ft

Condo

1153 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New The Village at Oxford Greens

71 LINKS WAY 71, OXFORD, CT, 06478, Oxford, CT 06478

$598,000

2 beds

2 baths

1,590 sq ft

71 LINKS WAY 71, 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 Heritage Village

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

$264,999

2 beds

2 baths

1,432 sq ft

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Waterways at Moriches

377 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$599,999

2 beds

2 baths

2,141 sq ft

Condo

377 QUARRY POND CT, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

New Woodridge Strathmore Terrace

58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$435,000

2 beds

2 baths

1,025 sq ft

Condo

58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Jefferson Village

113 VILLAGE RD B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$449,999

2 beds

2 baths

1,200 sq ft

Condo

113 VILLAGE RD B, YORKTOWN, NY, 10598

Community: Jefferson Village

New The Woods at Dunham Pond

29 HERON VIEW RD 29, NEW FAIRFIELD, CT, ..., New Fairfield, CT 06812

$334,000

1 beds

2 baths

1,590 sq ft

Condo

29 HERON VIEW RD 29, NEW FAIRFIELD, CT, ...

Community: The Woods at Dunham Pond

New Heritage Hills

37 HERITAGE HILLS DR A, SOMERS, NY, 1058..., Somers, NY 10589

$500,000

1 beds

1 baths

955 sq ft

Condo

37 HERITAGE HILLS DR A, SOMERS, NY, 1058...

Community: Heritage Hills

New Greenwood Village

131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$165,000

2 beds

2 baths

1,062 sq ft

Manufactured Home

131 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New The Waterways at Moriches

629 WATER WAY 29, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$715,000

2 beds

3 baths

1,611 sq ft

Condo

629 WATER WAY 29, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New Regency Meadows

108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611

$739,000

2 beds

3 baths

2,891 sq ft

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611

Community: Regency Meadows

New Heritage Hills

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

$569,000

2 beds

2 baths

1,296 sq ft

Condo

757 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Village

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

$409,000

2 beds

2 baths

1,432 sq ft

Condo

139 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

Foxwood Village

1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933, Brookhaven, NY 11933

$425,000

2 beds

2 baths

1,444 sq ft

Manufactured Home

1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933

Community: Foxwood Village

Heritage Village

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

$365,000

2 beds

2 baths

1,398 sq ft

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

69 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$289,900

2 beds

2 baths

1,044 sq ft

Condo

69 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$354,000

2 beds

2 baths

1,432 sq ft

Condo

122 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$324,900

2 beds

2 baths

1,398 sq ft

Condo

47 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Knoll

491 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,000

2 beds

2 baths

976 sq ft

Condo

491 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Village

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

$424,900

2 beds

2 baths

1,398 sq ft

Condo

553 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

23 DORSET CT F, YORKTOWN, NY, 10598, Yorktown, NY 10598

$315,000

2 beds

1 baths

925 sq ft

Condo

23 DORSET CT F, YORKTOWN, NY, 10598

Community: Jefferson Village

Country Village Estates

41 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$480,000

2 beds

2 baths

1,308 sq ft

Condo

41 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

Oronoque Village

664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,438 sq ft

Condo

664 OSAGE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

69 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$270,000

2 beds

2 baths

1,044 sq ft

Condo

69 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

Plymouth Estates at Mount Sinai

98 ANDREW DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$599,990

2 beds

2 baths

1,820 sq ft

Condo

98 ANDREW DR, BROOKHAVEN, NY, 11766

Community: Plymouth Estates at Mount Sinai

Heritage Village

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

$349,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

130 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: May 23, 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

271 homes near Cheshire

3 beds

2 baths

1,480 sq ft

Condo

2 beds

2 baths

1,416 sq ft

Condo

2 beds

2 baths

1,302 sq ft

Condo

3 beds

3 baths

2,730 sq ft

Condo

1 beds

1 baths

700 sq ft

Condo

2 beds

2 baths

1,480 sq ft

Condo

2 beds

2 baths

1,151 sq ft

Manufactured On Land

2 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

3 baths

2,254 sq ft

Condo

2 beds

2 baths

1,809 sq ft

Condo

2 beds

2 baths

1,350 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,590 sq ft

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

2,141 sq ft

Condo

2 beds

2 baths

1,025 sq ft

Condo

2 beds

2 baths