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

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 Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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

Questions? Call us: (860) 854-8527

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

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

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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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

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

Questions? Call us: (860) 854-8527

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

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Questions? Call us: (860) 854-8527

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

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

Questions? Call us: (860) 854-8527

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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

1 2 3...4

New 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, ...

Community: Glenwood Village

Greenwood Village

19 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$105,900

2 beds

2 baths

871 sq ft

Condo

19 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Leisure Village

200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$255,000

1 beds

1 baths

684 sq ft

Condo

200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196...

Community: Leisure Village

New Rivington

11 ORWICH CT 11, DANBURY, CT, 06810, Danbury, CT 06810

$649,900

3 beds

4 baths

1,572 sq ft

Condo

11 ORWICH CT 11, DANBURY, CT, 06810

Community: Rivington

New Windcrest East

116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119..., Riverhead, NY 11933

$774,900

3 beds

3 baths

2,200 sq ft

House

116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119...

Community: Windcrest East

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

Questions? Call us: (860) 854-8527

New Woodridge Strathmore Terrace

32 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

3 beds

3 baths

2,008 sq ft

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...

238 COACH DR 56, OYSTER BAY, NY, 11797

Community: Kensington Estates

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Questions? Call us: (860) 854-8527

New Heritage Village

18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$474,981

3 beds

2 baths

1,735 sq ft

Condo

18 HERITAGE CRST D, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Village at Oxford Greens

1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478

$713,775

2 beds

3 baths

2,536 sq ft

Condo

Community: The Waterways at Moriches

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

Questions? Call us: (860) 854-8527

Fairfield at St. James

409 ELTON CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$649,000

3 beds

3 baths

1,733 sq ft

Condo

409 ELTON CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Country Pointe Plainview

15103 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803

$1,075,000

2 beds

2 baths

1,335 sq ft

Condo

15103 ASPENWOOD DR, OYSTER BAY, NY, 1180...

Community: Country Pointe Plainview

Oronoque Village

44 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

2 beds

2 baths

1,400 sq ft

Condo

44 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

The Vineyards at Mount Sinai

51 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$1,085,000

2 beds

3 baths

3,214 sq ft

Condo

51 FARM ACRE CIR, BROOKHAVEN, NY, 11766

Community: The Vineyards at Mount Sinai

Heritage Village

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

$315,000

2 beds

2 baths

1,076 sq ft

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

513 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$584,900

2 beds

3 baths

1,620 sq ft

Condo

513 OPA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

The Summit at Bethel

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

$629,000

2 beds

3 baths

1,623 sq ft

Condo

50 GREAT HILL DR, BETHEL, CT, 06801

Community: The Summit at Bethel

Regency at Prospect

59 CHERRY CIR 59, PROSPECT, CT, 06712, Prospect, CT 06712

$575,000

2 beds

3 baths

2,067 sq ft

Condo

59 CHERRY CIR 59, PROSPECT, CT, 06712

Community: Regency at Prospect

Harbor View Estates

206 ANCHOR CT, BABYLON, NY, 11726, Babylon, NY 11726

$599,000

2 beds

2 baths

1,200 sq ft

Condo

206 ANCHOR CT, BABYLON, NY, 11726

Community: Harbor View Estates

South Pond Village

174 THISTLE POND DR 174, BLOOMFIELD, CT,..., Bloomfield, CT 06002

$449,900

2 beds

2 baths

1,535 sq ft

Condo

174 THISTLE POND DR 174, BLOOMFIELD, CT,...

Community: South Pond Village

Oronoque Village

778 QUINNIPIAC LN A, STRATFORD, CT, 0661..., Stratford, CT 06614

$480,000

1 beds

3 baths

1,175 sq ft

Condo

778 QUINNIPIAC LN A, STRATFORD, CT, 0661...

Community: Oronoque Village

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

Questions? Call us: (860) 854-8527

Heritage Village

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

$469,000

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$379,990

2 beds

1 baths

Condo

368 WOODBRIDGE DR A, 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 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 520 days. The average price of homes for sale in these communities is approximately $556,595, 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?

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126 communities

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

126 communities near Middletown

225 homes near Middletown

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

871 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

3 beds

4 baths

1,572 sq ft

Condo

3 beds

3 baths

2,200 sq ft

House

2 beds

2 baths

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,652 sq ft

Condo

3 beds

3 baths

2,008 sq ft

Condo

2 beds

2 baths

1,586 sq ft

Condo

2 beds

3 baths

1,941 sq ft

Condo

2 beds

2 baths

1,159 sq ft

Condo

2 beds

3 baths

1,928 sq ft

Condo

1 beds

3 baths

1,175 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

3 beds

4 baths

2,662 sq ft

Condo

3 beds

2 baths

1,735 sq ft

Condo

2 beds

3 baths

2,536 sq ft

Condo

2 beds

3 baths

2,536 sq ft

Condo

2 beds

2 baths