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

130 communities near Cheshire

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4.6 rating (9 reviews)

Meadowbrook Pointe Links ...

$300ks - $700ks

Meadowbrook Pointe Links ..., Medford, NY

New and Resale | 55+ age-restricted | Built 2010 - present | 280 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)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

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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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

Knickerbocker Bay Club

$700ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 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 Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

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

Questions? Call us: (475) 244-9781

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Hidden Harbor Estates

$500ks - $600ks

Hidden Harbor Estates, Copiague, NY

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes

Eastport Meadows

$400ks

Eastport Meadows, Eastport, NY

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes

The Vineyards at Mount Si...

$800ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

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

Questions? Call us: (475) 244-9781

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 20 homes

The Polo Club at Islandia

$600ks - $700ks

The Polo Club at Islandia, Islandia, NY

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

Stratford Park

$600ks - $800ks

Stratford Park, Melville, NY

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 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

The Seasons at Plainview

$500ks - $600ks

The Seasons at Plainview, Plainview, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

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

Questions? Call us: (475) 244-9781

Forest Mews

$300ks - $400ks

Forest Mews, Avon, CT

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes

The Village at Hunt Glen

$300ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 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?

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130 communities

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

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