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

130 communities near Cheshire

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Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

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Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Meadowbrooke Pointe East ...

$500ks - $600ks

Meadowbrooke Pointe East ..., East Meadow, NY

New Construction | 62+ age-restricted | Built 2019 - present | 104 homes

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

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Questions? Call us: (475) 244-9781

O'Meara Farm

$400ks

O'Meara Farm, Farmington, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

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Questions? Call us: (475) 244-9781

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

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

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Knickerbocker Bay Club

$700ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

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

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

Harbor View Estates

$400ks - $600ks

Harbor View Estates, Copiague, NY

New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

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

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Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes

Hidden Harbor Estates

$500ks - $600ks

Hidden Harbor Estates, Copiague, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

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

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Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Stratford Park

$600ks - $800ks

Stratford Park, Melville, NY

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

The Bridges at Oxford Gre...

$600ks

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

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

The Seasons at East North...

$700ks

The Seasons at East North..., East Northport, NY

New Construction | 55+ age-restricted | Built 2023 - present | 190 homes

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

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5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

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

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

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

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The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

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

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

1 2 3...4

New Jefferson Village

119 VILLAGE RD H, YORKTOWN, NY, 10598, Yorktown, NY 10598

$439,000

2 beds

2 baths

1,100 sq ft

Condo

119 VILLAGE RD H, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Hills

725 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$774,900

2 beds

2 baths

1,526 sq ft

Condo

725 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

New HarborView

626 VILLAGE GRN, NORTH HEMPSTEAD, NY, 11..., North Hempstead, NY 11050

$1,199,000

3 beds

3 baths

2,424 sq ft

Condo

626 VILLAGE GRN, NORTH HEMPSTEAD, NY, 11...

Community: HarborView

New Leisure Village

273 BERWICK CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$289,000

2 beds

1 baths

836 sq ft

Condo

273 BERWICK CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Heritage Village

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

$249,000

1 beds

1 baths

928 sq ft

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

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New Jefferson Village

129 COLUMBIA CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$469,999

2 beds

2 baths

1,100 sq ft

Condo

129 COLUMBIA CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

New Fairview at Oxford Greens

1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Village Estates

105 FRANCESCA WAY 105, BABYLON, NY, 1170..., Babylon, NY 11701

$559,000

2 beds

1 baths

1,229 sq ft

Condo

105 FRANCESCA WAY 105, BABYLON, NY, 1170...

Community: Village Estates

New Overlook

2079 SUMMIT LOOP 103, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

2 baths

1,948 sq ft

Condo

2079 SUMMIT LOOP 103, CARMEL, NY, 10512

Community: Overlook

New Glenwood Village

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$449,999

3 beds

2 baths

1,680 sq ft

Manufactured Home

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1...

Community: Glenwood Village

New Leisure Village

72 ENFIELD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,900

2 beds

1 baths

1,085 sq ft

Condo

72 ENFIELD CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Pond Spring Village

17 PONDVIEW CIR 17, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403

$474,900

2 beds

2 baths

1,474 sq ft

Condo

17 PONDVIEW CIR 17, BEACON FALLS, CT, 06...

Community: Pond Spring Village

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Questions? Call us: (475) 244-9781

New Heritage Village

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

$189,000

2 beds

2 baths

1,044 sq ft

Condo

331 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Country Pointe Preserve

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$865,000

2 beds

3 baths

1,998 sq ft

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

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

Questions? Call us: (475) 244-9781

Heritage Hills

29 HERITAGE HLS 29D, SOMERS, NY, 10589, Somers, NY 10589

$495,000

2 beds

3 baths

1,340 sq ft

Condo

29 HERITAGE HLS 29D, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

99 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,426 sq ft

Condo

99 SEMINOLE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$340,000

1 beds

3 baths

1,438 sq ft

Condo

89 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

The Waterways at Moriches

290 W MIDLAND POND CT 290, BROOKHAVEN, N..., Brookhaven, NY 11955

$629,000

2 beds

2 baths

1,440 sq ft

Condo

290 W MIDLAND POND CT 290, BROOKHAVEN, N...

Community: The Waterways at Moriches

The Seasons at Seaford

56 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783

$820,000

2 beds

3 baths

1,034 sq ft

Condo

56 SPRING DR, HEMPSTEAD, NY, 11783

Community: The Seasons at Seaford

Country Pointe Plainview

31201 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,150,000

2 beds

2 baths

1,379 sq ft

Condo

31201 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

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Questions? Call us: (475) 244-9781

Heritage Village

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

$279,000

2 beds

2 baths

1,432 sq ft

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

196 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$365,000

1 beds

2 baths

1,175 sq ft

Condo

196 APACHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Breton Hills

401 BRETON WAY 401, GLEN COVE, NY, 11542, Glen Cove, NY 11542

$699,999

2 beds

2 baths

1,300 sq ft

Condo

401 BRETON WAY 401, GLEN COVE, NY, 11542

Community: Breton Hills

Autumn Fields

5 QUAIL HOLW 5, ENFIELD, CT, 06082, Enfield, CT 06082

$399,900

2 beds

3 baths

1,679 sq ft

Condo

5 QUAIL HOLW 5, ENFIELD, CT, 06082

Community: Autumn Fields

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

Questions? Call us: (475) 244-9781

Jefferson Village

158 CARRIAGE CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$686,000

2 beds

2 baths

1,555 sq ft

Condo

158 CARRIAGE CT B, YORKTOWN, NY, 10598

Community: Jefferson Village

Sunrise Village

93 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$525,000

2 beds

2 baths

1,230 sq ft

Condo

93 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

The Villages at Mount Sinai Park

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$899,000

3 beds

3 baths

2,455 sq ft

House

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Jefferson Village

10 REGENTS PL D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$240,000

1 baths

550 sq ft

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598

Community: Jefferson Village

O'Meara Farm

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032

$480,000

2 beds

2 baths

1,416 sq ft

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032

Community: O'Meara Farm

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The Greens at Half Hollow

625 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$980,000

2 beds

3 baths

1,940 sq ft

Condo

625 MADEIRA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Meadowbrooke Pointe East Meadow

137 EMANUEL WAY, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$839,000

2 beds

3 baths

1,390 sq ft

Condo

137 EMANUEL WAY, HEMPSTEAD, NY, 11554

Community: Meadowbrooke Pointe East Meadow

Foxwood Village

1407 MIDDLE RD 91, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$364,000

2 beds

2 baths

1,532 sq ft

House

1407 MIDDLE RD 91, RIVERHEAD, NY, 11933

Community: Foxwood Village

Heritage Village

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

$360,000

2 beds

2 baths

1,432 sq ft

Condo

640 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$409,000

2 beds

2 baths

1,360 sq ft

Condo

47 HURON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (475) 244-9781

Leisure Village

279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$299,999

2 beds

1 baths

875 sq ft

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Country Village Estates

45 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$475,000

2 beds

2 baths

1,305 sq ft

Condo

45 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

The Villages at Mount Sinai Park

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$675,000

2 beds

3 baths

1,736 sq ft

House

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

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

Questions? Call us: (475) 244-9781

Regency at Prospect

104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712

$328,417

3 beds

2 baths

1,500 sq ft

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712

Community: Regency at Prospect

Rivington

131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810

$770,000

3 beds

3 baths

1,592 sq ft

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...

Community: Rivington

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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130 communities

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

130 communities near Cheshire

246 homes near Cheshire

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,526 sq ft

Condo

3 beds

3 baths

2,424 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

3 beds

3 baths

2,256 sq ft

Condo

3 beds

3 baths

2,256 sq ft

Condo

2 beds

1 baths

1,229 sq ft

Condo

2 beds

2 baths

1,948 sq ft

Condo

3 beds

2 baths

1,680 sq ft

Manufactured Home

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,474 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

1,998 sq ft

Condo

2 beds

3 baths

1,340 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,440 sq ft

Condo

2 beds