Middletown, CT 55+ active adult communities & homes for sale - Page 2

126 communities near Middletown

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The Vineyards at Miller P...

$500ks

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

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

4 rating (1 reviews)

Vineyards at Blue Point

$500ks - $700ks

Vineyards at Blue Point, Blue Point, NY

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

The Bel Aire at East Mead...

$300ks - $400ks

The Bel Aire at East Mead..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 95 homes

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

Questions? Call us: (860) 854-8527

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

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

Harbor View Estates

$400ks - $600ks

Harbor View Estates, Copiague, NY

New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

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.

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

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

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

The Seasons at Plainview

$500ks - $600ks

The Seasons at Plainview, Plainview, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

The Village at Hunt Glen

$300ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 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

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

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

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 homes

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 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

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

New Construction | Age-targeted | Built 2025 - 2026 | 25 homes

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

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

Questions? Call us: (860) 854-8527

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

1 2 3...4

Greenwood Village

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949

$245,000

2 beds

2 baths

1,130 sq ft

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...

Community: Greenwood Village

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 The Village at Oxford Greens

1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478

$663,775

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

$663,775

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478

$778,160

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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Questions? Call us: (860) 854-8527

New Fairview at Oxford Greens

$778,160

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478

$754,150

2 beds

3 baths

1,955 sq ft

Condo

Condo

37 HALLEY DR 17, BROOKHAVEN, NY, 11772

581 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

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

212 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614

$319,000

1 beds

2 baths

1,426 sq ft

Condo

212 AGAWAM DR B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Leisure Village

274 BERWICK CT C, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,000

2 beds

1 baths

836 sq ft

Condo

274 BERWICK CT C, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Bartlett Hill

19 PLUMROSE CT 19, PORTLAND, CT, 06480, Portland, CT 06480

$500,000

2 beds

3 baths

1,503 sq ft

19 PLUMROSE CT 19, PORTLAND, CT, 06480

Community: Bartlett Hill

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

$450,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (860) 854-8527

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

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 - Page 2

126 communities near Middletown

236 homes near Middletown

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

2 baths

1,067 sq ft

Condo

2 beds

3 baths

2,625 sq ft

Condo

2 beds

3 baths

2,820 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

3 baths

2,769 sq ft

Condo

2 beds

2 baths

1,243 sq ft

Condo

2 beds

2 baths

1,341 sq ft

Condo

2 beds

2 baths

1,240 sq ft

House

2 beds

1 baths

836 sq ft

Condo

2 beds

3 baths

1,940 sq ft

Condo

2 beds

3 baths

1,750 sq ft

Condo

2 beds