Middletown, CT 55+ active adult communities & homes for sale - Page 4

249 homes 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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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

Questions? Call us: (860) 854-8527

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 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

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

New and Resale | 55+ age-restricted | Built 2006 - present | 125 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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

The Cottages at Wire Mill

$1Ms

The Cottages at Wire Mill, Stamford, CT

New Construction | 55+ age-restricted | Built 2026 - present | 9 homes

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

Questions? Call us: (860) 854-8527

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

1 2 3...4

Windcrest East

5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$775,000

3 beds

3 baths

2,449 sq ft

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933

Community: Windcrest East

Oronoque Village

383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,360 sq ft

Condo

383 SEQUOIA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$349,900

2 beds

2 baths

1,398 sq ft

Condo

895 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Stoneleigh Woods at Riverhead

159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$674,999

2 beds

3 baths

2,172 sq ft

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Heritage Village

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

$389,900

2 beds

2 baths

1,432 sq ft

Condo

16 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

Spring Lake Village

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489

$350,000

2 beds

2 baths

1,230 sq ft

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...

Community: Spring Lake Village

Heritage Village

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

$299,900

2 beds

2 baths

1,032 sq ft

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$439,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

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

$394,990

2 beds

1 baths

Condo

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

Community: Leisure Village

Baldwin Station

15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461

$599,000

2 beds

3 baths

2,331 sq ft

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461

Community: Baldwin Station

The Village at Oxford Greens

941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Snug Harbor

58 HARBOR RD, BABYLON, NY, 11701, Babylon, NY 11701

$495,000

1 beds

1 baths

727 sq ft

Condo

58 HARBOR RD, BABYLON, NY, 11701

Community: Snug Harbor

Rivington

64 WARRINGTON ROUND 64, DANBURY, CT, 068..., Danbury, CT 06810

$615,000

3 beds

3 baths

1,600 sq ft

Condo

64 WARRINGTON ROUND 64, DANBURY, CT, 068...

Community: Rivington

Glenwood Village

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901

$469,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...

Community: Glenwood Village

Heritage Village

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$518,000

3 beds

2 baths

1,716 sq ft

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

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

Questions? Call us: (860) 854-8527

Leisure Village

66 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,900

2 beds

1 baths

1,085 sq ft

Condo

66 ENFIELD CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Greenwood Village

89 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$89,000

1 beds

1 baths

812 sq ft

Condo

89 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Setauket Meadows

66 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$739,999

2 beds

3 baths

1,878 sq ft

Condo

66 BRIANNA DR, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Heritage Village

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

$245,000

2 beds

2 baths

1,071 sq ft

Condo

773 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Newtown Woods

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470, Newtown, CT 06470

$595,000

2 beds

2 baths

1,747 sq ft

Condo

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470

Community: Newtown Woods

Glenwood Village

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ..., Riverhead, NY 11901

$239,999

2 beds

2 baths

980 sq ft

Manufactured Home

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...

Community: Glenwood Village

Pond Spring Village

111 PONDVIEW CIR, BEACON FALLS, CT, 0640..., Beacon Falls, CT 06403

$438,000

2 beds

2 baths

1,328 sq ft

Condo

111 PONDVIEW CIR, BEACON FALLS, CT, 0640...

Community: Pond Spring Village

Country Pointe Plainview

19303 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803

$1,148,000

2 beds

2 baths

1,335 sq ft

Condo

19303 ASPENWOOD DR, OYSTER BAY, NY, 1180...

Community: Country Pointe Plainview

Heritage Village

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

$310,000

2 beds

2 baths

1,398 sq ft

Condo

233 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

349 NIBLICK LN 349, OXFORD, CT, 06478, Oxford, CT 06478

$658,000

3 beds

2 baths

2,008 sq ft

Condo

349 NIBLICK LN 349, OXFORD, CT, 06478

Community: The Village at Oxford Greens

The Greens at Half Hollow

907 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$749,000

2 beds

2 baths

1,186 sq ft

Condo

907 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

Heritage Village

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

$360,000

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478

$658,000

3 beds

2 baths

2,152 sq ft

349 NIBLICK LN, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

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

$284,900

2 beds

2 baths

1,044 sq ft

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Country Pointe Plainview

55201 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,599,000

2 beds

2 baths

1,989 sq ft

Condo

55201 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

Spring Lake Village

21 HICKORY HL 21, SOUTHINGTON, CT, 06489, Southington, CT 06489

$248,000

2 beds

2 baths

1,285 sq ft

Condo

21 HICKORY HL 21, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

The Manors at The Colony Preserve

33 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$510,000

2 beds

2 baths

1,557 sq ft

Condo

33 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

The Waterways at Moriches

632 WATER WAY 32, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$799,000

2 beds

3 baths

1,874 sq ft

Condo

632 WATER WAY 32, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

The Seasons at Elwood

178 SUMMER CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,599,000

2 beds

3 baths

2,900 sq ft

Condo

178 SUMMER CIR, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

Greenwood Village

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$135,000

2 beds

2 baths

987 sq ft

House

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Fairfield at St. James

1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$649,000

2 beds

2 baths

948 sq ft

Condo

1205 GOTHAM DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Fairfield at St. James

606 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$424,000

1 beds

1 baths

752 sq ft

Condo

606 FLAIR CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

Questions? Call us: (860) 854-8527

Oronoque Village

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

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Vineyards at Moriches

20 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$759,000

2 beds

3 baths

1,984 sq ft

Condo

20 EMILIE DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

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 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.

Want more information about active adult communities around Middletown?

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249 homes

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Middletown, CT 55+ active adult communities & homes for sale - Page 4

127 communities near Middletown

249 homes near Middletown

3 beds

3 baths

2,449 sq ft

House

1 beds

3 baths

1,360 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

2,172 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

1 beds

2 baths

1,360 sq ft

Condo

2 beds

1 baths

Condo

2 beds

3 baths

2,331 sq ft

Condo

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,682 sq ft

1 beds

1 baths

727 sq ft

Condo

3 beds

3 baths

1,600 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Manufactured Home

3 beds

2 baths

1,716 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

1 beds

1 baths

812 sq ft

Condo

2 beds

3 baths

1,878 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo