Cheshire, CT 55+ active adult communities & homes for sale - Page 2

231 homes near Cheshire

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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

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 - $1Ms

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

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 (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

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.

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

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

Questions? Call us: (475) 244-9781

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

The Seasons at East Meado...

$400ks - $600ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

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

Questions? Call us: (475) 244-9781

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

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

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

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

Questions? Call us: (475) 244-9781

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

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

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

Questions? Call us: (475) 244-9781

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

1 2 3...4

Spring Lake Village

40 HICKORY HL # 40, SOUTHINGTON, CT, 064..., Southington, CT 06489

$233,527

2 beds

2 baths

1,211 sq ft

Condo

40 HICKORY HL # 40, SOUTHINGTON, CT, 064...

40 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (475) 244-9781

Meadowbrook Pointe Athletic Club & Spa

366 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ..., North Hempstead, NY 11590

$799,000

2 beds

2 baths

1,342 sq ft

Condo

366 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ...

Community: Meadowbrook Pointe Athletic Club & Spa

Heritage Village

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

$399,000

3 beds

2 baths

1,716 sq ft

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$260,000

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

430 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961

$369,000

2 beds

2 baths

1,200 sq ft

House

430 FALMOUTH CT A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

258 NEWCASTLE CT F, RIDGE, NY, 11961, Ridge, NY 11961

$279,000

2 beds

1 baths

875 sq ft

Condo

258 NEWCASTLE CT F, RIDGE, NY, 11961

Community: Leisure Village

Oak Meadow Estates

65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791

$495,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...

Community: Oak Meadow Estates

The Greens at Half Hollow

843 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$699,000

2 beds

2 baths

1,150 sq ft

Condo

843 MADEIRA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

South Pond Village

81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$259,999

2 beds

2 baths

1,204 sq ft

Condo

81 SILO WAY 81, BLOOMFIELD, CT, 06002

Community: South Pond Village

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

Questions? Call us: (475) 244-9781

The Coves at Melville

54 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$579,000

2 beds

2 baths

1,162 sq ft

Condo

54 MORLEY CIR, HUNTINGTON, NY, 11747

Community: The Coves at Melville

Heritage Hills

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

$599,000

1 beds

2 baths

1,296 sq ft

Condo

680 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Villas at Seminary Hill

7102 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512

$439,999

2 beds

2 baths

1,144 sq ft

Condo

7102 PANKIN DR, CARMEL, NY, 10512

Community: Villas at Seminary Hill

Leisure Knoll

304 KINGSTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$530,000

2 beds

2 baths

1,000 sq ft

Condo

304 KINGSTON CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Hills

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

$749,000

3 beds

2 baths

1,689 sq ft

Condo

243 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

133 BANNOCK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$635,000

2 beds

3 baths

2,038 sq ft

Condo

133 BANNOCK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$299,900

2 beds

2 baths

1,144 sq ft

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Chatfield Farms

8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$699,900

3 beds

4 baths

2,610 sq ft

Condo

8 WOODLAND PATH 8, BEACON FALLS, CT, 064...

Community: Chatfield Farms

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

Questions? Call us: (475) 244-9781

Heritage Village

419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$500,000

3 beds

2 baths

1,716 sq ft

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$167,000

2 beds

2 baths

1,164 sq ft

Condo

16 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Village

230 BLACKPOOL CT A, RIDGE, NY, 11961, Ridge, NY 11961

$289,900

2 beds

1 baths

836 sq ft

Condo

230 BLACKPOOL CT A, RIDGE, NY, 11961

Community: Leisure Village

Overlook

3014 EASTVIEW LN # 110, CARMEL, NY, 1051..., Carmel, NY 10512

$779,000

2 beds

3 baths

2,466 sq ft

Condo

3014 EASTVIEW LN # 110, CARMEL, NY, 1051...

Community: Overlook

Meadow Brook Estates

215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478

$589,000

3 beds

3 baths

2,207 sq ft

Condo

215 MEADOW BROOK RD # 215, OXFORD, CT, 0...

Community: Meadow Brook Estates

Leisure Village

406 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$245,000

1 beds

1 baths

704 sq ft

Condo

406 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

Long Hill Village

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

$539,900

1 beds

3 baths

1,370 sq ft

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

Leisure Knoll

190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$479,999

2 beds

1 baths

913 sq ft

House

190 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Village Estates

34 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701

$569,999

2 beds

2 baths

1,251 sq ft

Condo

34 SARAH CT, AMITYVILLE, NY, 11701

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

Encore Atlantic Shores

236 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$790,000

2 beds

2 baths

2,215 sq ft

Condo

236 ENCORE BLVD, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Leisure Knoll

475 STRATFORD LN, RIDGE, NY, 11961, Ridge, NY 11961

$519,000

3 beds

2 baths

1,592 sq ft

House

475 STRATFORD LN, RIDGE, NY, 11961

Community: Leisure Knoll

1 2 3 4 5…6

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.

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231 homes

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Cheshire, CT 55+ active adult communities & homes for sale - Page 2

129 communities near Cheshire

231 homes near Cheshire

2 beds

2 baths

1,211 sq ft

Condo

1 beds

1 baths

844 sq ft

Condo

2 beds

1 baths

1,036 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

2 beds

2 baths

1,139 sq ft

Condo

2 beds

2 baths

1,342 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,200 sq ft

House

2 beds

1 baths

875 sq ft

Condo

2 beds

4 baths

2,164 sq ft

Condo

2 beds

2 baths

1,150 sq ft

Condo

2 beds

2 baths

1,204 sq ft

Condo

2 beds

2 baths

1,162 sq ft

Condo

1 beds

2 baths

1,296 sq ft

Condo

2 beds

2 baths

1,144 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

2 beds

3 baths

2,038 sq ft

Condo

2 beds