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

125 communities near Middletown

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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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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Questions? Call us: (860) 854-8527

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Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

New Construction | 55+ age-restricted | Built 2023 - present | 142 homes

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

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Questions? Call us: (860) 854-8527

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

Questions? Call us: (860) 854-8527

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

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Questions? Call us: (860) 854-8527

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)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

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Questions? Call us: (860) 854-8527

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 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 Middletown? 55places can help!

Questions? Call us: (860) 854-8527

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

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

Questions? Call us: (860) 854-8527

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

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

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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 Middletown? 55places can help!

Questions? Call us: (860) 854-8527

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

1 2 3...4

New 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

New 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

New Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

New Castle Heights of Cheshire

151 VICTORIA DR, CHESHIRE, CT, 06410, Cheshire, CT 06410

$769,900

2 beds

4 baths

2,843 sq ft

Condo

151 VICTORIA DR, CHESHIRE, CT, 06410

Community: Castle Heights of Cheshire

New Country Village Estates

163 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$454,500

2 beds

2 baths

1,261 sq ft

Condo

163 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

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

New The Waterways at Moriches

188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$775,000

2 beds

2 baths

2,100 sq ft

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New Spring Lake Village

872 GLACIER WAY 872, SOUTHINGTON, CT, 06..., Southington, CT 06489

$319,000

2 beds

2 baths

1,226 sq ft

Condo

872 GLACIER WAY 872, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

New Glenwood Village

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ..., Riverhead, NY 11901

$130,000

2 beds

1 baths

720 sq ft

Manufactured Home

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ...

Community: Glenwood Village

New Heritage Village

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

$229,000

2 beds

2 baths

1,076 sq ft

Condo

101 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

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

$325,000

2 beds

2 baths

1,076 sq ft

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Eagles Walk at East Quogue

1504 AERIE WAY 1504, SOUTHAMPTON, NY, 11..., Southampton, NY 11942

$545,000

2 beds

2 baths

1,341 sq ft

House

1504 AERIE WAY 1504, SOUTHAMPTON, NY, 11...

Community: Eagles Walk at East Quogue

New The Summit at Bethel

20 GREAT HILL DR 20, BETHEL, CT, 06801, Bethel, CT 06801

$649,000

3 beds

3 baths

2,159 sq ft

Condo

20 GREAT HILL DR 20, BETHEL, CT, 06801

Community: The Summit at Bethel

New Leisure Village

120 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$205,000

1 beds

1 baths

684 sq ft

Condo

120 EXMORE CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 854-8527

New Heritage Village

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

$353,000

2 beds

2 baths

1,432 sq ft

Condo

401 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Strathmore Gate East

42 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$425,000

2 beds

2 baths

1,112 sq ft

Condo

42 FREEMONT LN, BROOKHAVEN, NY, 11727

177 THISTLE POND DR 177, BLOOMFIELD, CT,...

Community: South Pond Village

The Village at Oxford Greens

523 PUTTING GREEN LN 523, OXFORD, CT, 06..., Oxford, CT 06478

$625,000

2 beds

2 baths

2,008 sq ft

Condo

523 PUTTING GREEN LN 523, OXFORD, CT, 06...

Community: The Village at Oxford Greens

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

Questions? Call us: (860) 854-8527

Greenwood Village

2 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$192,500

2 beds

2 baths

1,064 sq ft

Condo

2 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Heritage Village

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$225,000

1 beds

1 baths

928 sq ft

Condo

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

The Greens at Half Hollow

928 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$615,000

2 beds

2 baths

1,262 sq ft

Condo

928 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Oronoque Village

72 DAKOTA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$539,500

1 beds

3 baths

1,118 sq ft

Condo

72 DAKOTA LN B, STRATFORD, CT, 06614

Condo

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064...

Condo

79 HERITAGE VLG A, SOUTHBURY, CT, 06488

Condo

43 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (860) 854-8527

Leisure Glen

233 GLEN DR 233, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$565,000

2 beds

2 baths

1,666 sq ft

Condo

233 GLEN DR 233, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Leisure Village

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,308 sq ft

Condo

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Community: Leisure Village

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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125 communities

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

125 communities near Middletown

214 homes near Middletown

3 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

1,592 sq ft

Condo

3 beds

3 baths

Condo

2 beds

4 baths

2,843 sq ft

Condo

2 beds

2 baths

1,261 sq ft

Condo

2 beds

2 baths

2,100 sq ft

Condo

2 beds

2 baths

1,226 sq ft

Condo

2 beds

1 baths

720 sq ft

Manufactured Home

2 beds

2 baths

1,076 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

2 baths

1,341 sq ft

House

3 beds

3 baths

2,159 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,112 sq ft

Condo

2 beds

2 baths

1,312 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

2 beds

2 baths

1,587 sq ft

Condo

2 beds

2 baths

1,454 sq ft

Condo

3 beds

3 baths