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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

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

Questions? Call us: (860) 854-8527

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

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

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

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

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

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

Want to learn more about 55+ 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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

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)

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

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

Questions? Call us: (860) 854-8527

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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 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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 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 Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

1 2 3...4

New The Villages at Mount Sinai Park

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$749,000

3 beds

3 baths

2,500 sq ft

House

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Leisure Knoll

225 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$540,000

2 beds

2 baths

1,094 sq ft

House

225 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New The Villages at Mount Sinai Park

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$929,000

3 beds

3 baths

2,816 sq ft

House

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Country Pointe Plainview

12103 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803

$1,075,000

2 beds

2 baths

1,335 sq ft

Condo

12103 ASPENWOOD DR, OYSTER BAY, NY, 1180...

Community: Country Pointe Plainview

New The Greens at Half Hollow

385 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,299,999

3 beds

3 baths

3,060 sq ft

Condo

385 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

New The Villages at Mount Sinai Park

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$839,999

2 beds

2 baths

1,736 sq ft

House

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Village Estates

12 SARAH CT, BABYLON, NY, 11701, Babylon, NY 11701

$579,000

2 beds

2 baths

1,243 sq ft

Condo

12 SARAH CT, BABYLON, NY, 11701

Community: Village Estates

New Snug Harbor

66 HARBOR N, BABYLON, NY, 11701, Babylon, NY 11701

$589,500

1 beds

1 baths

727 sq ft

Condo

66 HARBOR N, BABYLON, NY, 11701

Community: Snug Harbor

New Saddle Lakes

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

$629,000

3 beds

3 baths

1,837 sq ft

Condo

156 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

New Encore at Lake Grove

8 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$634,000

2 beds

3 baths

1,378 sq ft

Condo

8 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New Leisure Knoll

257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$399,000

2 beds

2 baths

1,000 sq ft

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961

1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190...

Community: Stoneleigh Woods at Riverhead

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

Questions? Call us: (860) 854-8527

New Oronoque Village

664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,438 sq ft

664 OSAGE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New The Greens at Half Hollow

398 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,599,999

2 beds

2 baths

2,525 sq ft

Condo

398 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Oronoque Village

543 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$585,000

1 beds

3 baths

1,426 sq ft

Condo

543 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New Encore at Lake Grove

176 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$609,000

2 beds

2 baths

1,429 sq ft

Condo

176 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New Regency at Prospect

196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712

$307,127

3 beds

2 baths

1,500 sq ft

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712

Community: Regency at Prospect

New The Seasons at Elwood

244 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,375,000

2 beds

3 baths

2,256 sq ft

Condo

244 FALL CT, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

Heritage Village

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

$390,000

2 beds

2 baths

1,432 sq ft

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488

47 HARBOR N, BABYLON, NY, 11701

Community: Snug Harbor

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

Questions? Call us: (860) 854-8527

Leisure Village

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$349,000

2 beds

1 baths

1,085 sq ft

Condo

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Setauket Meadows

100 COVE LN 100, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$769,000

2 beds

3 baths

1,820 sq ft

Condo

100 COVE LN 100, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Oronoque Village

315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$549,000

2 beds

3 baths

1,434 sq ft

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961

$299,000

2 beds

1 baths

875 sq ft

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...

Community: Leisure Village

Heritage Village

14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$269,000

2 beds

2 baths

1,000 sq ft

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Manors at The Colony Preserve

17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$559,000

2 beds

2 baths

1,557 sq ft

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

Leisure Knoll

541 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$529,000

3 beds

2 baths

1,412 sq ft

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Village

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

$309,000

3 beds

2 baths

1,716 sq ft

Condo

847 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

132 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$470,000

1 beds

3 baths

1,426 sq ft

Condo

132 BISON LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$405,000

2 beds

2 baths

1,432 sq ft

Condo

648 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Gardens of Wilbraham

56 CHERRY DR 56, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$419,000

2 beds

2 baths

1,213 sq ft

Condo

56 CHERRY DR 56, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

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

Questions? Call us: (860) 854-8527

The Greens at Half Hollow

163 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,599,000

2 beds

2 baths

2,500 sq ft

Condo

163 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Fairfield at St. James

309 FLAIR DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$454,000

1 beds

2 baths

983 sq ft

Condo

309 FLAIR DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

225 homes near Middletown

3 beds

3 baths

2,500 sq ft

House

2 beds

2 baths

1,094 sq ft

House

3 beds

3 baths

2,816 sq ft

House

2 beds

2 baths

1,335 sq ft

Condo

3 beds

3 baths

3,060 sq ft

Condo

2 beds

2 baths

1,736 sq ft

House

2 beds

2 baths

1,243 sq ft

Condo

1 beds

1 baths

727 sq ft

Condo

3 beds

3 baths

1,837 sq ft

Condo

2 beds

3 baths

1,378 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

3 baths

2,652 sq ft

Condo

2 beds

3 baths

1,942 sq ft

Condo

2 beds

3 baths

2,820 sq ft

Condo

2 beds

2 baths

1,944 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

1 beds

3 baths

1,438 sq ft

2 beds

2 baths

2,525 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths