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

126 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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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 Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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

Questions? Call us: (860) 854-8527

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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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

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

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

Questions? Call us: (860) 854-8527

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

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

Questions? Call us: (860) 854-8527

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

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

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

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

Questions? Call us: (860) 854-8527

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

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

1 2 3...4

New Greenwood Village

5190 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$239,000

2 beds

2 baths

1,258 sq ft

Condo

5190 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

102 WINGED FOOT WAY, RIVERHEAD, NY, 1190...

Community: Sunken Pond Estates

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

Questions? Call us: (860) 854-8527

New Country Pointe Plainview

33204 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,735,000

2 beds

2 baths

1,976 sq ft

Condo

33204 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

New Leisure Village

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$228,888

2 beds

1 baths

836 sq ft

Condo

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961

448 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

New The Powder Forest Homes

6 RONAN WAY 6, SIMSBURY, CT, 06070, Simsbury, CT 06070

2 beds

2 baths

1,807 sq ft

Condo

832 BROOKSIDE CT 832, NEWTOWN, CT, 06470

Condo

104 ARI LN, BROOKHAVEN, NY, 11934

Community: Vineyards at Brookfield

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

Questions? Call us: (860) 854-8527

Stone Ridge Estates

160 CHRISTINE DR, HUNTINGTON, NY, 11746, Huntington, NY 11746

2 beds

2 baths

2,008 sq ft

567 INVERNESS CT 567, OXFORD, CT, 06478

Community: The Village at Oxford Greens

The Powder Forest Homes

15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070

$949,000

4 beds

3 baths

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Country Pointe Plainview

82101 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$2,398,000

3 beds

4 baths

2,697 sq ft

House

82101 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

Oronoque Village

283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$625,000

2 beds

3 baths

1,415 sq ft

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

The Greens at Half Hollow

517 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,275,000

2 beds

3 baths

2,000 sq ft

Condo

517 BARDINI DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

283 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,395,000

3 beds

3 baths

2,700 sq ft

Condo

283 ALTESSA BLVD, HUNTINGTON, 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

The Seasons at Elwood

35 WINTER PL, HUNTINGTON, NY, 11731, Huntington, NY 11731

$949,000

2 beds

3 baths

1,500 sq ft

Condo

35 WINTER PL, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

Encore Atlantic Shores

176 MELODY CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$899,000

2 beds

3 baths

2,800 sq ft

Condo

176 MELODY CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

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 Founders Ridge, Bartlett Hollow.

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 539 days. The average price of homes for sale in these communities is approximately $555,135, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Sonoma Woods average around $599,900, while homes in Bartlett Hollow average around $579,900.

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Want to learn more about 55+ communities in Middletown?

Call us: (860) 854-8527

126 communities

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REIN updates its listings on a daily basis. Data last updated: Jun 25, 2026.
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Middletown, CT 55+ active adult communities & homes for sale

126 communities near Middletown

229 homes near Middletown

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

3 baths

2,062 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

2 beds

2 baths

1,976 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

3 beds

3 baths

2,759 sq ft

Condo

2 beds

2 baths

1,430 sq ft

Condo

1 beds

1 baths

530 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

3 baths

1,864 sq ft

2 beds

2 baths

1,631 sq ft

Condo

2 beds

2 baths

1,188 sq ft

Condo

2 beds

2 baths

1,807 sq ft

Condo

3 beds

3 baths

2,310 sq ft

Condo

2 beds

2 baths

1,379 sq ft

Condo

2 beds

2 baths

954 sq ft

Condo

2 beds

3 baths