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

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

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

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4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

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

Questions? Call us: (860) 854-8527

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

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

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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

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 Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

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

1 2 3...4

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

New Vineyards at Brookfield

104 ARI LN, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$879,000

2 beds

4 baths

2,718 sq ft

Condo

104 ARI LN, BROOKHAVEN, NY, 11934

Community: Vineyards at Brookfield

New Stone Ridge Estates

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

$780,000

2 beds

2 baths

Condo

160 CHRISTINE DR, HUNTINGTON, NY, 11746

Community: Stone Ridge Estates

New Heritage Village

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

$424,900

2 beds

2 baths

1,398 sq ft

Condo

892 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Country Village Estates

110 THEODORE DR 110, BROOKHAVEN, NY, 117..., Brookhaven, NY 11727

$475,000

2 beds

2 baths

1,261 sq ft

Condo

110 THEODORE DR 110, BROOKHAVEN, NY, 117...

Community: Country Village Estates

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Questions? Call us: (860) 854-8527

New Heritage Village

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

$335,000

2 beds

2 baths

1,398 sq ft

Condo

339 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Rivington

82 WINDING RIDGE WAY 82, DANBURY, CT, 06..., Danbury, CT 06810

$925,000

3 beds

4 baths

2,388 sq ft

Condo

82 WINDING RIDGE WAY 82, DANBURY, CT, 06...

Community: Rivington

New The Village at Oxford Greens

567 INVERNESS CT 567, OXFORD, CT, 06478, Oxford, CT 06478

$665,000

2 beds

2 baths

2,008 sq ft

567 INVERNESS CT 567, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New 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

New 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

New 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

New 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

New 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

New 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

New 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

New The Waterways at Moriches

605 BAY VIEW CIR 5, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$649,000

2 beds

3 baths

1,485 sq ft

Condo

605 BAY VIEW CIR 5, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

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

Questions? Call us: (860) 854-8527

New Meadow Brook Estates

211 MEADOW BROOK RD 211, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

3 beds

3 baths

2,201 sq ft

Condo

211 MEADOW BROOK RD 211, OXFORD, CT, 064...

Community: Meadow Brook Estates

New Heritage Village

10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$364,000

3 beds

2 baths

1,716 sq ft

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Rivington

104 CENTER MEADOW LN 104, DANBURY, CT, 0..., Danbury, CT 06810

$510,000

2 beds

2 baths

1,330 sq ft

Condo

104 CENTER MEADOW LN 104, DANBURY, CT, 0...

Community: Rivington

New Snug Harbor

26 HARBOR RD, BABYLON, NY, 11701, Babylon, NY 11701

$699,000

2 beds

2 baths

1,131 sq ft

Condo

26 HARBOR RD, BABYLON, NY, 11701

Community: Snug Harbor

New Spring Lake Village

342 SONGBIRD LN 342, SOUTHINGTON, CT, 06..., Southington, CT 06489

$259,900

2 beds

1 baths

912 sq ft

Condo

342 SONGBIRD LN 342, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

New Leisure Village

134 EASTBOURNE CT 134D, BROOKHAVEN, NY, ..., Brookhaven, NY 11961

$329,000

2 beds

1 baths

875 sq ft

Condo

134 EASTBOURNE CT 134D, BROOKHAVEN, NY, ...

Community: Leisure Village

New Liberty at Newtown

49 JO AL CT 49, NEWTOWN, CT, 06470, Newtown, CT 06470

$635,000

2 beds

3 baths

2,341 sq ft

Condo

49 JO AL CT 49, NEWTOWN, CT, 06470

Community: Liberty at Newtown

New Heritage Village

1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$248,000

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

New Encore Atlantic Shores

203 BACH CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$759,000

2 beds

2 baths

1,889 sq ft

Condo

203 BACH CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

New Vineyards at Moriches

27 TONI CT, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$759,999

2 beds

3 baths

2,251 sq ft

Condo

27 TONI CT, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

New Heritage Village

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

$237,000

2 beds

2 baths

1,076 sq ft

Condo

24 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

Heritage Village

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

$249,000

2 beds

2 baths

1,076 sq ft

Condo

59 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$559,000

2 beds

3 baths

2,542 sq ft

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Westhampton Pines

112 ASHLEY, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$1,225,000

3 beds

3 baths

2,304 sq ft

Condo

112 ASHLEY, SOUTHAMPTON, NY, 11977

Community: Westhampton Pines

Heritage Village

196 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$229,900

2 beds

2 baths

1,044 sq ft

Condo

196 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairfield at St. James

703 DREW DR D7, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$429,999

1 beds

1 baths

752 sq ft

Condo

703 DREW DR D7, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Newbury Village

46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804

$699,000

2 beds

4 baths

2,560 sq ft

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...

Community: Newbury Village

Liberty at Newtown

25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470

$545,000

2 beds

2 baths

1,413 sq ft

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470

Community: Liberty at Newtown

Oronoque Village

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

$565,000

1 beds

3 baths

1,426 sq ft

Condo

253 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Knoll

183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$415,000

2 beds

1 baths

960 sq ft

Condo

183 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Regency at Prospect

6 LILAC LN 6, PROSPECT, CT, 06712, Prospect, CT 06712

$474,900

2 beds

3 baths

1,552 sq ft

Condo

6 LILAC LN 6, PROSPECT, CT, 06712

Community: Regency at Prospect

Country Pointe Plainview

52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803

$1,749,000

2 beds

3 baths

1,750 sq ft

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...

Community: Country Pointe Plainview

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

Questions? Call us: (860) 854-8527

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

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

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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126 communities

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

126 communities near Middletown

226 homes near Middletown

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

4 baths

2,718 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,261 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

4 baths

2,388 sq ft

Condo

2 beds

2 baths

2,008 sq ft

4 beds

3 baths

1,878 sq ft

3 beds

4 baths

2,697 sq ft

House

2 beds

3 baths

1,415 sq ft

Condo

2 beds

3 baths

2,000 sq ft

Condo

3 beds

3 baths

2,700 sq ft

Condo

2 beds

3 baths

1,500 sq ft

Condo

2 beds

3 baths

2,800 sq ft

Condo

2 beds

3 baths

1,485 sq ft

Condo

3 beds

3 baths

2,201 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,330 sq ft

Condo

2 beds

2 baths

1,131 sq ft

Condo