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

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

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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

Chatfield Farms

9 LAKEVIEW RISE 9, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$499,000

2 beds

3 baths

1,700 sq ft

Condo

9 LAKEVIEW RISE 9, BEACON FALLS, CT, 064...

Community: Chatfield Farms

Kensington Estates

48 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797

$2,349,999

6 beds

5 baths

4,333 sq ft

House

48 PLAINVIEW RD, WOODBURY, NY, 11797

Community: Kensington Estates

South Pond Village

162 THISTLE POND DR 162, BLOOMFIELD, CT,..., Bloomfield, CT 06002

$395,000

2 beds

2 baths

1,341 sq ft

Condo

162 THISTLE POND DR 162, BLOOMFIELD, CT,...

Community: South Pond Village

The Retreat at Carmel

18 WHEELER CT, CARMEL, NY, 10512, Carmel, NY 10512

$749,900

2 beds

3 baths

2,035 sq ft

Condo

18 WHEELER CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

The Village at Oxford Greens

117 COUNTRY CLUB DR 117, OXFORD, CT, 064..., Oxford, CT 06478

$639,900

3 beds

3 baths

2,666 sq ft

117 COUNTRY CLUB DR 117, OXFORD, CT, 064...

Community: The Village at Oxford Greens

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

Questions? Call us: (475) 244-9781

Meadowbrook Pointe Athletic Club & Spa

568 PACING WAY # 568, WESTBURY, NY, 1159..., Westbury, NY 11590

$875,000

2 beds

2 baths

1,328 sq ft

Condo

568 PACING WAY # 568, WESTBURY, NY, 1159...

Community: Meadowbrook Pointe Athletic Club & Spa

The Seasons at East Northport

142 AUGUST CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$790,302

2 beds

2 baths

1,536 sq ft

Condo

142 AUGUST CIR, HUNTINGTON, NY, 11731

Community: The Seasons at East Northport

The Village at Oxford Greens

301 FAIRWAY DR 301, OXFORD, CT, 06478, Oxford, CT 06478

$619,000

2 beds

2 baths

2,080 sq ft

Condo

301 FAIRWAY DR 301, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Westhampton Pines

39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11..., Westhampton, NY 11977

$1,495,000

3 beds

2 baths

2,500 sq ft

Condo

39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11...

Community: Westhampton Pines

Granite Woods

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$229,000

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762

Community: Granite Woods

Oronoque Village

635 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

3 baths

1,454 sq ft

Condo

635 N TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$195,000

2 beds

2 baths

1,032 sq ft

Condo

73 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0..., Oxford, CT 06478

$650,000

3 beds

3 baths

2,731 sq ft

Condo

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0...

Community: The Village at Oxford Greens

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

Questions? Call us: (475) 244-9781

Meadowbrook Pointe Athletic Club & Spa

428 TROTTING LN # 428, WESTBURY, NY, 115..., Westbury, NY 11590

$1,150,000

2 beds

3 baths

2,628 sq ft

Condo

428 TROTTING LN # 428, WESTBURY, NY, 115...

Community: Meadowbrook Pointe Athletic Club & Spa

Snug Harbor

170 HARBOR, AMITYVILLE, NY, 11701, Amityville, NY 11701

$550,000

2 beds

3 baths

1,334 sq ft

Condo

170 HARBOR, AMITYVILLE, NY, 11701

Community: Snug Harbor

Greenwood Village

54 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$130,000

2 beds

2 baths

1,134 sq ft

Condo

54 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood Village

Heritage Village

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

$299,900

2 beds

2 baths

1,365 sq ft

Condo

198 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Summit at Bethel

12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680..., Bethel, CT 06801

$619,900

2 beds

3 baths

2,023 sq ft

Condo

12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680...

Community: The Summit at Bethel

Oronoque Village

13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

1 beds

2 baths

1,330 sq ft

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614

Community: Oronoque Village

Greenwood Village

42 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$99,000

2 beds

2 baths

960 sq ft

Condo

42 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Heritage Hills

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

$645,000

3 beds

2 baths

1,689 sq ft

Condo

140 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

The Village at Oxford Greens

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478

$645,000

3 beds

3 baths

2,595 sq ft

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...

Community: The Village at Oxford Greens

The Village at Oxford Greens

185 COUNTRY CLUB DR 185, OXFORD, CT, 064..., Oxford, CT 06478

$645,000

3 beds

3 baths

2,595 sq ft

185 COUNTRY CLUB DR 185, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Heritage Village

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

$320,000

2 beds

2 baths

1,365 sq ft

Condo

423 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

278 BERWICK CT UNIT B B, RIDGE, NY, 1196..., Ridge, NY 11961

$359,900

2 beds

1 baths

875 sq ft

Condo

278 BERWICK CT UNIT B B, RIDGE, NY, 1196...

Community: Leisure Village

Regency at Woodbridge

3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525

$629,000

3 beds

3 baths

Condo

3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065...

Community: Regency at Woodbridge

Regency at Woodbridge

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ..., Woodbridge, CT 06525

$749,000

3 beds

3 baths

Condo

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ...

Community: Regency at Woodbridge

Heritage Village

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

$199,900

2 beds

2 baths

1,044 sq ft

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

418 WEYMOUTH CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,900

2 beds

1 baths

1,036 sq ft

Condo

418 WEYMOUTH CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

The Waterways at Moriches

554 MIRROR POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$499,000

2 beds

2 baths

1,497 sq ft

Condo

554 MIRROR POND CT, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

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

Questions? Call us: (475) 244-9781

Oronoque Village

446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$635,000

3 beds

3 baths

1,426 sq ft

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

Heritage Hills

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

$475,000

2 beds

2 baths

1,205 sq ft

Condo

182 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

151 S TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$460,000

1 beds

3 baths

1,426 sq ft

Condo

151 S TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

The Retreat at Carmel

4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512

$759,900

2 beds

3 baths

2,035 sq ft

Condo

4 FROST CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Village

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

$339,900

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Liberty at Newtown

79 SUZIE DR # 79, NEWTOWN, CT, 06470, Newtown, CT 06470

$575,000

2 beds

3 baths

2,317 sq ft

Condo

79 SUZIE DR # 79, NEWTOWN, CT, 06470

Community: Liberty at Newtown

Fairfield at St. James

901 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780

$499,000

2 beds

2 baths

1,230 sq ft

Condo

901 FENWAY RD, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

Leisure Glen

10 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961

$599,900

2 beds

2 baths

1,666 sq ft

Condo

10 OAKDALE CT, RIDGE, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (475) 244-9781

Heritage Village

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

$310,000

2 beds

2 baths

1,432 sq ft

Condo

891 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Coves at Melville

6 MORLEY CIR, MELVILLE, NY, 11747, Melville, NY 11747

$530,000

2 beds

2 baths

Condo

6 MORLEY CIR, MELVILLE, NY, 11747

Community: The Coves at Melville

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.

Want more information about active adult communities around Cheshire?

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231 homes

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

129 communities near Cheshire

231 homes near Cheshire

2 beds

3 baths

1,700 sq ft

Condo

6 beds

5 baths

4,333 sq ft

House

2 beds

2 baths

1,341 sq ft

Condo

2 beds

3 baths

2,035 sq ft

Condo

3 beds

3 baths

2,666 sq ft

2 beds

2 baths

1,328 sq ft

Condo

2 beds

2 baths

1,536 sq ft

Condo

2 beds

2 baths

2,080 sq ft

Condo

3 beds

2 baths

2,500 sq ft

Condo

1 beds

1 baths

889 sq ft

Condo

1 beds

3 baths

1,454 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

3 beds

3 baths

2,731 sq ft

Condo

2 beds

3 baths

2,628 sq ft

Condo

2 beds

3 baths

1,334 sq ft

Condo

2 beds

2 baths

1,134 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

3 baths

2,023 sq ft

Condo

1 beds

2 baths

1,330 sq ft

Condo

2 beds

2 baths