Middletown, CT 55+ active adult communities & homes for sale

124 communities near Middletown

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5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

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

Sonoma Woods

$300Ks

Sonoma Woods, Middletown, CT

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

Bartlett Hollow

$200Ks - $400Ks

Bartlett Hollow, Middletown, CT

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

3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

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

Questions? Call us: (860) 854-8527

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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

Rivington

$400Ks - $800Ks

Rivington, Danbury, CT

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

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

The Village at Oxford Gre...

$600Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 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

$400Ks

Leisure Knoll, Ridge, NY

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

Country Pointe Plainview

$1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (2 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

Leisure Glen

$500Ks

Leisure Glen, Ridge, NY

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

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Questions? Call us: (860) 854-8527

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks

Glenwood Village, Riverhead, NY

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

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Questions? Call us: (860) 854-8527

3.7 rating (3 reviews)

Greenwood Village

<$100k - $200Ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

The Seasons at East Meado...

$500Ks - $600Ks

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

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

Regency at Prospect

$400Ks - $500Ks

Regency at Prospect, Prospect, CT

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

The Waterways at Moriches

$400Ks - $500Ks

The Waterways at Moriches, Moriches, NY

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

3.5 rating (2 reviews)

Foxwood Village

$400Ks - $500Ks

Foxwood Village, Calverton, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

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Questions? Call us: (860) 854-8527

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

4 rating (1 reviews)

Vineyards at Blue Point

$800Ks

Vineyards at Blue Point, Blue Point, NY

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

The Club at Melville

$500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 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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Questions? Call us: (860) 854-8527

Meadow Brook Estates

$500Ks

Meadow Brook Estates, Oxford, CT

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

5 rating (1 reviews)

Encore Atlantic Shores

$700Ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

The Summit at Bethel

$600Ks

The Summit at Bethel, Bethel, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

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

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $800Ks

Encore at Lake Grove, Lake Grove, NY

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

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Questions? Call us: (860) 854-8527

Woodridge Strathmore Terr...

$400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

Sunrise Village, Sayville, NY

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

Brierly Pond Village

$400Ks

Brierly Pond Village, Millbury, MA

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes

Saddle Lakes

$400Ks

Saddle Lakes, Riverhead, NY

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

Country Village Estates

$400Ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

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

Questions? Call us: (860) 854-8527

5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $500Ks

Sunken Pond Estates, Riverhead, NY

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

5 rating (1 reviews)

Westhampton Pines

$900Ks - $1Ms

Westhampton Pines, Westhampton, NY

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

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Questions? Call us: (860) 854-8527

5 rating (1 reviews)

The Villages at Mount Sin...

$500Ks - $700Ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

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

1 2 3...4

Newtown Woods

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064..., Newtown, CT 06470

$478,000

2 beds

2 baths

1,504 sq ft

Condo

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064...

Community: Newtown Woods

Oronoque Village

195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

2 beds

3 baths

1,575 sq ft

Condo

195 BAYFIELD LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Chatfield Farms

18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403

$599,000

2 beds

3 baths

2,719 sq ft

18 FIELDSTONE LN # 18, BEACON FALLS, CT,...

Community: Chatfield Farms

New 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

Heritage Village

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

$285,000

2 beds

2 baths

1,432 sq ft

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 854-8527

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

Questions? Call us: (860) 854-8527

New 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

Oronoque Village

617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$524,900

1 beds

3 baths

1,438 sq ft

Condo

617 CHEROKEE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

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

$480,000

1 beds

3 baths

1,426 sq ft

Condo

151 SOUTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

New 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

375 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$424,999

1 beds

3 baths

1,550 sq ft

Condo

375 PIUTE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

2 baths

1,454 sq ft

Condo

87 CREEK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,900

1 beds

3 baths

1,620 sq ft

Condo

289 AGAWAM DR B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$279,900

2 beds

2 baths

1,365 sq ft

Condo

825 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 854-8527

Heritage Village

25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$449,000

2 beds

2 baths

1,447 sq ft

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Village at Oxford Greens

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

$669,900

3 beds

3 baths

2,595 sq ft

Condo

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

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 854-8527

Oronoque Village

522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

2 beds

3 baths

1,426 sq ft

Condo

522 IROQUOIS LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New South Pond Village

170 THISTLE POND DR # 170, BLOOMFIELD, C..., Bloomfield, CT 06002

$457,500

2 beds

2 baths

1,459 sq ft

170 THISTLE POND DR # 170, BLOOMFIELD, C...

Community: South Pond Village

Heritage Village

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

$515,000

3 beds

2 baths

1,716 sq ft

Condo

977 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

811 VILLAGE RD # 811, SOUTHINGTON, CT, 0..., Southington, CT 06489

$399,900

2 beds

3 baths

1,550 sq ft

Condo

811 VILLAGE RD # 811, SOUTHINGTON, CT, 0...

Community: Spring Lake Village

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

Questions? Call us: (860) 854-8527

Oronoque Village

488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

2 beds

3 baths

1,438 sq ft

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

736 QUINNIPIAC LN B, STRATFORD, CT, 0661..., Stratford, CT 06614

$465,000

1 beds

3 baths

1,426 sq ft

Condo

736 QUINNIPIAC LN B, STRATFORD, CT, 0661...

Community: Oronoque Village

Oronoque Village

766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

766 NYACK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

The Village at Oxford Greens

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0..., Oxford, CT 06478

$615,000

2 beds

2 baths

1,532 sq ft

Condo

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$615,000

2 beds

2 baths

1,532 sq ft

Condo

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...

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

Community: Regency at Woodbridge

New 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

Rivington

$499,900

2 beds

2 baths

1,229 sq ft

Condo

1 RIVINGTON WAY UNIT 201, DANBURY, CT, 0...

Community: Rivington

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

Questions? Call us: (860) 854-8527

Heritage Village

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

$355,000

2 beds

164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$465,000

1 beds

2 baths

1,175 sq ft

Condo

164 BISON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Regency at Woodbridge

10 HILLCREST DR # 5, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525

$995,000

3 beds

3 baths

Condo

10 HILLCREST DR # 5, WOODBRIDGE, CT, 065...

Community: Regency at Woodbridge

Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there are no large communities, no medium communities, and 3 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Middletown?

The smallest 55+ communities in Middletown has 25 homes, the largest has 75 homes, and the average communities consists of 56 homes.

Are there new 55+ homes available in Middletown?

Yes, there are new 55+ homes available in Middletown. The most recent communities started in Middletown include Founders Ridge, Bartlett Hollow, Sonoma Woods. There are also 2 communities in Middletown that offer new construction homes, including Bartlett Hollow, Founders Ridge.

Are there gated 55+ communities in Middletown?

Yes, there is gated 55+ communities in Middletown. Approximately 33.3% of 55+ communities in the area are gated. For instance, Bartlett Hollow is a gated communities with 25 homes.

How long do listings in 55+ communities in Middletown typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Middletown stay on the market for around 237 days. The average price of homes for sale in these communities is approximately $577,386, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Sonoma Woods average around $649,900, while homes in Bartlett Hollow average around $579,139.

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124 communities

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Middletown, CT 55+ active adult communities & homes for sale

124 communities near Middletown

189 homes near Middletown

2 beds

2 baths

1,504 sq ft

Condo

2 beds

3 baths

1,575 sq ft

Condo

2 beds

3 baths

2,719 sq ft

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

1,330 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

3 baths

2,023 sq ft

Condo

1 beds

3 baths

1,550 sq ft

Condo

1 beds

2 baths

1,454 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

3 beds

3 baths

2,595 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

1,426 sq ft

Condo

2 beds

3 baths

4,023 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

3 baths