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

259 homes near Middletown

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5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

No reviews yet

Sonoma Woods

$300Ks - $300Ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

No reviews yet

Bartlett Hollow

$200Ks - $400Ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

3.6 rating (7 reviews)

Heritage Village

$200Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

No reviews yet

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

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

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No reviews yet

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

No reviews yet

Rivington

$400Ks - $500Ks

Rivington, Danbury, CT

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

No reviews yet

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

The Village at Oxford Gre...

$500Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

No reviews yet

Leisure Knoll

$300Ks - $500Ks

Leisure Knoll, Ridge, NY

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

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No reviews yet

Country Pointe Plainview

$1Ms - $1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (2 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

No reviews yet

Leisure Glen

$400Ks - $400Ks

Leisure Glen, Ridge, NY

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

No reviews yet

Spring Lake Village

$200Ks - $200Ks

Spring Lake Village, Southington, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $400Ks

Glenwood Village, Riverhead, NY

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

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

Questions? Call us: (860) 854-8527

3.7 rating (3 reviews)

Greenwood Village

$100Ks - $200Ks

Greenwood Village, Manorville, NY

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

No reviews yet

The Seasons at East Meado...

$500Ks - $600Ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

No reviews yet

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

No reviews yet

The Waterways at Moriches

$400Ks - $700Ks

The Waterways at Moriches, Moriches, NY

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

3.5 rating (2 reviews)

Foxwood Village

$300Ks - $400Ks

Foxwood Village, Calverton, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks - $500Ks

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

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

4 rating (1 reviews)

Vineyards at Blue Point

$800Ks - $800Ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

No reviews yet

The Club at Melville

$500Ks - $500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

No reviews yet

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

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

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

Questions? Call us: (860) 854-8527

No reviews yet

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

5 rating (1 reviews)

Encore Atlantic Shores

$600Ks - $900Ks

Encore Atlantic Shores, Eastport, NY

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

No reviews yet

The Summit at Bethel

$600Ks - $600Ks

The Summit at Bethel, Bethel, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$600Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $800Ks

Encore at Lake Grove, Lake Grove, NY

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

No reviews yet

Woodridge Strathmore Terr...

$400Ks - $400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

Sunrise Village, Sayville, NY

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

No reviews yet

Brierly Pond Village

$400Ks - $400Ks

Brierly Pond Village, Millbury, MA

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

No reviews yet

Saddle Lakes

$400Ks - $400Ks

Saddle Lakes, Riverhead, NY

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

No reviews yet

Country Village Estates

$300Ks - $400Ks

Country Village Estates, Coram, NY

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

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

Questions? Call us: (860) 854-8527

5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $500Ks

Sunken Pond Estates, Riverhead, NY

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

No reviews yet

The Seasons at East North...

$700Ks - $700Ks

The Seasons at East North..., East Northport, NY

New Construction | 55+ age-restricted | Built 2023 - present | 190 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)

The Villages at Mount Sin...

$600Ks - $700Ks

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

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

No reviews yet

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

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

1 2 3...4

Westhampton Pines

112 ASHLEY DR, WESTHAMPTON, NY, 11977, Westhampton, NY 11977

$1,399,000

3 beds

3 baths

2,306 sq ft

Condo

112 ASHLEY DR, WESTHAMPTON, NY, 11977

Community: Westhampton Pines

Leisure Knoll

407 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961

$514,990

2 beds

2 baths

100 sq ft

Condo

407 BELFAST LN, RIDGE, NY, 11961

Community: Leisure Knoll

Windmill Gate

18 DAWN DR, OAKDALE, NY, 11769, Oakdale, NY 11769

$639,999

2 beds

2 baths

1,175 sq ft

House

18 DAWN DR, OAKDALE, NY, 11769

Community: Windmill Gate

Glenwood Village

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901

$149,000

2 beds

1 baths

840 sq ft

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...

Community: Glenwood Village

The Waterways at Moriches

106 E MIDLAND POND CT # 1, MORICHES, NY,..., Moriches, NY 11955

$499,000

2 beds

2 baths

1,982 sq ft

Condo

106 E MIDLAND POND CT # 1, MORICHES, NY,...

Community: The Waterways at Moriches

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

Questions? Call us: (860) 854-8527

Encore Atlantic Shores

167 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941

$955,000

2 beds

3 baths

3,136 sq ft

Condo

167 MELODY CT, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Leisure Village

488A FAIRWAY CT # 488A, RIDGE, NY, 11961, Ridge, NY 11961

$449,000

2 beds

2 baths

1,180 sq ft

Condo

488A FAIRWAY CT # 488A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

46 TRENT CT C, RIDGE, NY, 11961, Ridge, NY 11961

$365,000

2 beds

1 baths

1,085 sq ft

Condo

46 TRENT CT C, RIDGE, NY, 11961

Community: Leisure Village

Greenwood Village

57 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$159,999

2 beds

2 baths

1,000 sq ft

Condo

57 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Village

247 NEWCASTLE CT A, RIDGE, NY, 11961, Ridge, NY 11961

$425,000

2 beds

2 baths

1,564 sq ft

Condo

247 NEWCASTLE CT A, RIDGE, NY, 11961

Community: Leisure Village

Greenwood Village

16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$179,899

2 beds

2 baths

1,200 sq ft

Manufactured Home

16 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Village

231 BLACKPOOL CT F, RIDGE, NY, 11961, Ridge, NY 11961

$305,000

2 beds

1 baths

875 sq ft

Condo

231 BLACKPOOL CT F, RIDGE, NY, 11961

Community: Leisure Village

Leisure Knoll

304 KINGSTON CT, RIDGE, NY, 11961, Ridge, NY 11961

$429,000

2 beds

2 baths

976 sq ft

Condo

304 KINGSTON CT, RIDGE, NY, 11961

Community: Leisure Knoll

The Villages at Mount Sinai Park

4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$799,999

3 beds

3 baths

2,850 sq ft

Condo

4 OAKHURST CT, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Stone Ridge Estates

156 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746

$775,000

2 beds

2 baths

1,700 sq ft

Condo

156 CHRISTINE DR, DIX HILLS, NY, 11746

Community: Stone Ridge Estates

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

Questions? Call us: (860) 854-8527

Leisure Village

120 EXMORE CT D, RIDGE, NY, 11961, Ridge, NY 11961

$239,990

1 beds

1 baths

684 sq ft

Condo

120 EXMORE CT D, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

4 GUILFORD CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961

$469,900

2 beds

2 baths

1,486 sq ft

Condo

4 GUILFORD CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

New Harvest Pointe

32 MILLSTONE LN 16, CUTCHOGUE, NY, 11935, Cutchogue, NY 11935

$1,125,000

2 beds

3 baths

1,600 sq ft

Condo

32 MILLSTONE LN 16, CUTCHOGUE, NY, 11935

Community: Harvest Pointe

New Encore Atlantic Shores

113 OVERTURE PL, EASTPORT, NY, 11941, Eastport, NY 11941

$895,000

2 beds

3 baths

3,037 sq ft

Condo

113 OVERTURE PL, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

The Waterways at Moriches

204 RIVER DR, MORICHES, NY, 11955, Moriches, NY 11955

$789,000

2 beds

2 baths

1,790 sq ft

Condo

204 RIVER DR, MORICHES, NY, 11955

Community: The Waterways at Moriches

The Villages at Mount Sinai Park

25 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$799,000

2 beds

3 baths

2,229 sq ft

Condo

25 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Greenwood Village

1 WILLOW CT, MANORVILLE, NY, 11949, Manorville, NY 11949

$259,000

2 beds

2 baths

1,450 sq ft

Condo

1 WILLOW CT, MANORVILLE, NY, 11949

Community: Greenwood Village

New The Club at Melville

171 CLUBHOUSE CIR, MELVILLE, NY, 11747, Melville, NY 11747

$577,465

2 beds

2 baths

1,262 sq ft

Condo

171 CLUBHOUSE CIR, MELVILLE, NY, 11747

Community: The Club at Melville

New Greenwood Village

99 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$295,000

2 beds

2 baths

1,487 sq ft

Condo

99 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Village

424 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961

$279,900

1 beds

1 baths

782 sq ft

Condo

424 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 854-8527

New Fairfield at St. James

607 CABOT CT 607, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

1 beds

2 baths

929 sq ft

Condo

607 CABOT CT 607, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Greenwood Village

93 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$109,000

2 beds

2 baths

1,100 sq ft

Condo

93 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

New The Greens at Half Hollow

259 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$1,599,000

3 beds

4 baths

3,100 sq ft

Condo

259 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

423 FLORENCIA PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,225,000

3 beds

3 baths

2,500 sq ft

Condo

423 FLORENCIA PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

New Strathmore Gate East

53 FREEDOM LN, CORAM, NY, 11727, Coram, NY 11727

$440,000

2 beds

1 baths

1,036 sq ft

Condo

53 FREEDOM LN, CORAM, NY, 11727

Community: Strathmore Gate East

New The Vineyards at Miller Place

48 AVERY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$679,900

2 beds

3 baths

1,486 sq ft

Condo

48 AVERY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

The Seasons at East Northport

142 AUGUST CIR, EAST NORTHPORT, NY, 1173..., East Northport, NY 11731

$780,302

2 beds

2 baths

1,536 sq ft

Condo

142 AUGUST CIR, EAST NORTHPORT, NY, 1173...

Community: The Seasons at East Northport

Sunken Pond Estates

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$469,000

2 beds

3 baths

1,350 sq ft

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

The Seasons at East Meadow

383 SUMMER CT, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$640,000

2 beds

2 baths

1,272 sq ft

Condo

383 SUMMER CT, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

Leisure Village

48 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961

$355,000

2 beds

1 baths

1,278 sq ft

Condo

48 TRENT CT B, RIDGE, NY, 11961

House

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

1 2 3 4 5 6…7

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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259 homes near Middletown

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

123 communities near Middletown

259 homes near Middletown

3 beds

3 baths

2,306 sq ft

Condo

2 beds

2 baths

100 sq ft

Condo

2 beds

2 baths

1,175 sq ft

House

2 beds

1 baths

840 sq ft

Mobile Home

2 beds

2 baths

1,982 sq ft

Condo

2 beds

3 baths

3,136 sq ft

Condo

2 beds

2 baths

1,180 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,564 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Manufactured Home

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

976 sq ft

Condo

3 beds

3 baths

2,850 sq ft

Condo

2 beds

2 baths

1,700 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

2 baths

1,486 sq ft

Condo

2 beds

3 baths

1,600 sq ft

Condo

2 beds

3 baths

3,037 sq ft

Condo

2 beds