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

124 communities near Middletown

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3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

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

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

3.7 rating (3 reviews)

Greenwood Village

<$100k - $200Ks

Greenwood Village, Manorville, NY

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

The Village at Oxford Gre...

$600Ks - $700Ks

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

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

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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

Harmony Place

$400Ks

Harmony Place, Rutland, MA

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

The Waterways at Moriches

$400Ks - $500Ks

The Waterways at Moriches, Moriches, NY

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $200Ks

Glenwood Village, Riverhead, NY

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

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Leisure Knoll

$400Ks - $500Ks

Leisure Knoll, Ridge, NY

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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Rivington

$400Ks - $800Ks

Rivington, Danbury, CT

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

5 rating (1 reviews)

Encore Atlantic Shores

$700Ks

Encore Atlantic Shores, Eastport, NY

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

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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

Regency at Woodbridge

$600Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

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Questions? Call us: (860) 854-8527

Fairview at Oxford Greens

$600Ks - $700Ks

Fairview at Oxford Greens, Oxford, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $700Ks

Chatfield Farms, Beacon Falls, CT

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

The Manors at The Colony ...

$500Ks

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

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

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

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

Country Pointe Plainview

$1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $700Ks

Encore at Lake Grove, Lake Grove, NY

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

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Questions? Call us: (860) 854-8527

The Coves at Melville

$500Ks

The Coves at Melville, Melville, NY

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

5 rating (1 reviews)

Westhampton Pines

$1Ms

Westhampton Pines, Westhampton, NY

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

Kensington Estates

$2Ms

Kensington Estates, Woodbury, NY

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

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

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

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

Questions? Call us: (860) 854-8527

The Villas at Narraganset...

$500Ks

The Villas at Narraganset..., Lindenhurst, NY

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

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

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

Village Estates

$500Ks

Village Estates, Amityville, NY

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

Stone Ridge Estates

$700Ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

The Vineyards at Miller P...

$600Ks

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

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

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Questions? Call us: (860) 854-8527

Leisure Glen

$400Ks - $500Ks

Leisure Glen, Ridge, NY

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

Strathmore Gate East

$300Ks - $400Ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes

5 rating (1 reviews)

The Villages at Mount Sin...

$500Ks - $700Ks

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

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

The Seasons at East North...

$700Ks

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

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

Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

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

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

Questions? Call us: (860) 854-8527

The Seasons at Plainview

$600Ks - $700Ks

The Seasons at Plainview, Plainview, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes

3.5 rating (2 reviews)

Foxwood Village

$400Ks - $500Ks

Foxwood Village, Calverton, NY

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

Snug Harbor

$600Ks - $700Ks

Snug Harbor, Amityville, NY

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

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

Questions? Call us: (860) 854-8527

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

Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

1 2 3...4

New Oak Meadow Estates

65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791

$495,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...

Community: Oak Meadow Estates

New The Greens at Half Hollow

843 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$699,000

2 beds

2 baths

1,150 sq ft

Condo

843 MADEIRA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New South Pond Village

81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$259,999

2 beds

2 baths

1,204 sq ft

Condo

81 SILO WAY 81, BLOOMFIELD, CT, 06002

Community: South Pond Village

New Brierly Pond Village

196 HORNE WAY # 196, MILLBURY, MA, 01527, Millbury, MA 01527

$515,000

2 beds

4 baths

2,100 sq ft

Condo

196 HORNE WAY # 196, MILLBURY, MA, 01527

Community: Brierly Pond Village

New The Coves at Melville

54 MORLEY CIR, MELVILLE, NY, 11747, Melville, NY 11747

$579,000

2 beds

2 baths

1,162 sq ft

Condo

54 MORLEY CIR, MELVILLE, NY, 11747

Community: The Coves at Melville

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

Questions? Call us: (860) 854-8527

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

Questions? Call us: (860) 854-8527

New Leisure Knoll

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

$530,000

2 beds

2 baths

1,000 sq ft

Condo

304 KINGSTON CT, RIDGE, NY, 11961

Community: Leisure Knoll

New Oronoque Village

133 BANNOCK LN, STRATFORD, CT, 06614, Stratford, CT 06614

$635,000

2 beds

3 baths

2,038 sq ft

Condo

133 BANNOCK LN, STRATFORD, CT, 06614

Community: Oronoque Village

New Heritage Village

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

$299,900

2 beds

2 baths

1,144 sq ft

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Chatfield Farms

8 WOODLAND PATH # 8, BEACON FALLS, CT, 0..., Beacon Falls, CT 06403

$724,900

3 beds

4 baths

2,610 sq ft

Condo

8 WOODLAND PATH # 8, BEACON FALLS, CT, 0...

Community: Chatfield Farms

New Chatfield Farms

8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$724,900

3 beds

4 baths

2,610 sq ft

230 BLACKPOOL CT A, RIDGE, NY, 11961

Community: Leisure Village

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Questions? Call us: (860) 854-8527

The Seasons at East Meadow

479 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$619,000

2 beds

2 baths

1,358 sq ft

House

479 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

Encore at Lake Grove

17 SONATA CT, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$635,000

2 beds

3 baths

1,486 sq ft

Condo

17 SONATA CT, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

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

Questions? Call us: (860) 854-8527

Meadow Brook Estates

215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478

$589,000

3 beds

3 baths

2,207 sq ft

Condo

215 MEADOW BROOK RD # 215, OXFORD, CT, 0...

Community: Meadow Brook Estates

Leisure Village

406 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$245,000

1 beds

1 baths

704 sq ft

Condo

406 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

Long Hill Village

71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$539,900

1 beds

3 baths

1,370 sq ft

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

Leisure Knoll

190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$479,999

2 beds

1 baths

913 sq ft

House

190 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Village Estates

34 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701

$569,999

2 beds

2 baths

1,251 sq ft

Condo

34 SARAH CT, AMITYVILLE, NY, 11701

Community: Village Estates

Heritage Village

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

$295,000

2 beds

2 baths

1,432 sq ft

Condo

915 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

Greenwood Village

126 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$225,000

2 beds

2 baths

1,032 sq ft

Condo

126 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Encore at Lake Grove

171 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$799,000

2 beds

3 baths

2,189 sq ft

Condo

171 SYMPHONY DR, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

745 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$644,900

1 beds

3 baths

1,620 sq ft

Condo

445 NORTH TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (860) 854-8527

Rivington

1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681..., Danbury, CT 06810

$899,900

3 beds

4 baths

2,596 sq ft

Condo

1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681...

Community: Rivington

Heritage Village

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

$249,000

2 beds

2 baths

1,071 sq ft

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Encore Atlantic Shores

236 ENCORE BLVD, EASTPORT, NY, 11941, Eastport, NY 11941

$790,000

2 beds

2 baths

2,215 sq ft

Condo

236 ENCORE BLVD, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Leisure Knoll

475 STRATFORD LN, RIDGE, NY, 11961, Ridge, NY 11961

$519,000

3 beds

2 baths

1,592 sq ft

House

475 STRATFORD LN, RIDGE, NY, 11961

Community: Leisure Knoll

Glenwood Village

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$245,000

2 beds

2 baths

1,156 sq ft

Manufactured Home

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...

House

48 PLAINVIEW RD, WOODBURY, NY, 11797

Community: Kensington Estates

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

Questions? Call us: (860) 854-8527

South Pond Village

162 THISTLE POND DR 162, BLOOMFIELD, CT,..., Bloomfield, CT 06002

$395,000

2 beds

2 baths

1,341 sq ft

Condo

162 THISTLE POND DR 162, BLOOMFIELD, CT,...

Community: South Pond Village

The Village at Oxford Greens

117 COUNTRY CLUB DR 117, OXFORD, CT, 064..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,666 sq ft

117 COUNTRY CLUB DR 117, OXFORD, CT, 064...

Community: The Village at Oxford Greens

The Seasons at East Northport

142 AUGUST CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$790,302

2 beds

2 baths

1,536 sq ft

Condo

142 AUGUST CIR, HUNTINGTON, NY, 11731

Community: The Seasons at East Northport

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

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Leisure Glen

77 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,699 sq ft

House

77 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

The Manors at The Colony Preserve

34 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967

$515,000

2 beds

2 baths

1,357 sq ft

Condo

34 GREENTREE CT, SHIRLEY, NY, 11967

Community: The Manors at The Colony Preserve

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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124 communities

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

124 communities near Middletown

200 homes near Middletown

2 beds

4 baths

2,164 sq ft

Condo

2 beds

2 baths

1,150 sq ft

Condo

2 beds

2 baths

1,204 sq ft

Condo

2 beds

4 baths

2,100 sq ft

Condo

2 beds

2 baths

1,162 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

3 baths

2,038 sq ft

Condo

2 beds

2 baths

1,144 sq ft

Condo

3 beds

4 baths

2,610 sq ft

Condo

3 beds

4 baths

2,610 sq ft

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,164 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

1,358 sq ft

House

2 beds

3 baths

1,486 sq ft

Condo

3 beds

3 baths

2,207 sq ft

Condo

1 beds

1 baths

704 sq ft

Condo

1 beds

3 baths

1,370 sq ft

Condo

2 beds

1 baths

913 sq ft

House

2 beds

2 baths