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

$200Ks - $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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Questions? Call us: (860) 854-8527

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 - $600Ks

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...

$500Ks - $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

Spring Lake Village, Southington, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $200Ks

Glenwood Village, Riverhead, NY

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

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

Questions? Call us: (860) 854-8527

3.7 rating (3 reviews)

Greenwood Village

$100Ks - $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

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

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

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

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 - $800Ks

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

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

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

504 GOTHAM CT, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

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

Leisure Village

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

$250,000

1 beds

1 baths

782 sq ft

Condo

423 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

New Leisure Glen

289 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961

$500,000

2 beds

2 baths

1,635 sq ft

Condo

289 GLEN DR, RIDGE, NY, 11961

Community: Leisure Glen

Plymouth Estates at Mount Sinai

230 IRA RD # 230, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$589,999

2 beds

2 baths

1,317 sq ft

Condo

230 IRA RD # 230, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Leisure Village

42 TRENT CT D, RIDGE, NY, 11961, Ridge, NY 11961

$345,000

2 beds

1 baths

895 sq ft

Condo

42 TRENT CT D, RIDGE, NY, 11961

Community: Leisure Village

The Greens at Half Hollow

1126 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747

$629,888

2 beds

2 baths

1,150 sq ft

Condo

1126 SAVOY DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

911 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$629,000

2 beds

2 baths

1,134 sq ft

Condo

911 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

259 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$1,430,000

3 beds

4 baths

3,100 sq ft

Condo

259 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

910 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$779,000

2 beds

2 baths

1,120 sq ft

Condo

910 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

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

Questions? Call us: (860) 854-8527

New The Villages at Mount Sinai Park

78 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$799,000

2 beds

2 baths

2,135 sq ft

Condo

78 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Leisure Village

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961

$342,000

2 beds

1 baths

1,278 sq ft

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...

Condo

118 HARBOR, AMITYVILLE, NY, 11701

Community: Snug Harbor

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

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Village Estates

66 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701

$499,000

2 beds

2 baths

1,243 sq ft

Condo

66 SARAH CT, AMITYVILLE, NY, 11701

Community: Village Estates

Saddle Lakes

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$749,990

3 beds

3 baths

1,837 sq ft

Condo

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Stoneleigh Woods at Riverhead

67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$619,000

2 beds

3 baths

1,972 sq ft

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

The Vineyards at Miller Place

45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$650,000

2 beds

3 baths

1,853 sq ft

Condo

45 HALLEY LN, MILLER PLACE, NY, 11764

Condo

474 DARWEN DR B, RIDGE, NY, 11961

Condo

113 OVERTURE PL, EASTPORT, NY, 11941

304 GOTHAM WAY, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

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

Questions? Call us: (860) 854-8527

The Waterways at Moriches

477 WOODSCREEK CT, MORICHES, NY, 11955, Moriches, NY 11955

$565,000

3 beds

2 baths

1,839 sq ft

Condo

477 WOODSCREEK CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

Plymouth Estates at Mount Sinai

166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$579,999

2 beds

2 baths

1,820 sq ft

House

166 IRA RD, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

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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Want to learn more about 55+ communities in Middletown?

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124 communities

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

124 communities near Middletown

176 homes near Middletown

2 beds

2 baths

938 sq ft

Condo

2 beds

1 baths

1,074 sq ft

Condo

2 beds

1 baths

816 sq ft

Mobile Home

2 beds

2 baths

1,434 sq ft

Condo

2 beds

2 baths

1,236 sq ft

House

1 beds

1 baths

782 sq ft

Condo

2 beds

2 baths

1,635 sq ft

Condo

2 beds

2 baths

1,317 sq ft

Condo

2 beds

1 baths

895 sq ft

Condo

2 beds

2 baths

1,150 sq ft

Condo

2 beds

2 baths

1,134 sq ft

Condo

3 beds

4 baths

3,100 sq ft

Condo

2 beds

2 baths

1,120 sq ft

Condo

2 beds

2 baths

2,135 sq ft

Condo

2 beds

1 baths

1,278 sq ft

Condo

2 beds

2 baths

1,587 sq ft

Condo

2 beds

2 baths

1,215 sq ft

Condo

2 beds

2 baths

1,250 sq ft

Condo

2 beds

2 baths

1,147 sq ft

Condo

2 beds