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

124 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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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

Questions? Call us: (860) 854-8527

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Questions? Call us: (860) 854-8527

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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 Village at Oxford Gre...

$400ks - $500ks

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

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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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

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

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

Questions? Call us: (860) 854-8527

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

The Seasons at East Meado...

$400ks - $600ks

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

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

The Manors at The Colony ...

$300ks - $400ks

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

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

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Questions? Call us: (860) 854-8527

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

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Questions? Call us: (860) 854-8527

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

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Questions? Call us: (860) 854-8527

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

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

Questions? Call us: (860) 854-8527

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

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

Questions? Call us: (860) 854-8527

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

1 2 3...4

New The Villages at Mount Sinai Park

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$799,000

3 beds

3 baths

2,455 sq ft

Condo

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Rivington

424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810

$510,000

2 beds

2 baths

1,258 sq ft

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...

Community: Rivington

New Bartlett Hill

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480

$479,900

2 beds

3 baths

1,404 sq ft

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480

Community: Bartlett Hill

New Meadowbrook Pointe Links & Spa

83 PACIFIC DUNES CT 83, BROOKHAVEN, NY, ..., Brookhaven, NY 11763

$749,990

3 beds

3 baths

2,047 sq ft

Condo

83 PACIFIC DUNES CT 83, BROOKHAVEN, NY, ...

Community: Meadowbrook Pointe Links & Spa

New Leisure Glen

263 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,315 sq ft

Condo

263 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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 Stoneleigh Woods at Riverhead

153 STONELEIGH DR 153, RIVERHEAD, NY, 11..., Riverhead, NY 11901

$699,000

3 beds

3 baths

2,107 sq ft

Condo

153 STONELEIGH DR 153, RIVERHEAD, NY, 11...

Community: Stoneleigh Woods at Riverhead

New Strathmore Gate East

25 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$329,000

1 beds

1 baths

750 sq ft

Condo

25 FREEMONT LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

New The Greens at Half Hollow

236 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,698,000

2 beds

3 baths

2,500 sq ft

Condo

236 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Leisure Glen

415 LEISURE DR 415, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$642,000

2 beds

2 baths

1,685 sq ft

Condo

415 LEISURE DR 415, BROOKHAVEN, NY, 1196...

Community: Leisure Glen

New Oronoque Village

639 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

2 beds

3 baths

1,438 sq ft

Condo

639 ONONDAGA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New The Seasons at East Meadow

483 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$654,000

2 beds

2 baths

1,358 sq ft

Condo

483 SPRING DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

New Fairfield at St. James

908 DREW DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$609,000

2 beds

2 baths

1,050 sq ft

Condo

908 DREW DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New The Villages at Mount Sinai Park

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

$789,000

3 beds

3 baths

2,455 sq ft

Condo

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

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

Questions? Call us: (860) 854-8527

New Greenwood Village

43 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$264,999

2 beds

2 baths

1,164 sq ft

Mobile Home

43 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Sunken Pond Estates

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

$489,000

2 beds

3 baths

1,350 sq ft

Condo

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

Community: Sunken Pond Estates

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

Questions? Call us: (860) 854-8527

New The Seasons at East Meadow

394 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$649,000

2 beds

2 baths

1,670 sq ft

Condo

394 SPRING DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

New Leisure Knoll

506 LANCASTER CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,000

2 beds

2 baths

1,394 sq ft

House

506 LANCASTER CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Heritage Village

41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

3 baths

1,479 sq ft

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488

Community: Heritage Village

New Greenwood Village

65A VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$134,900

1 beds

1 baths

672 sq ft

Condo

65A VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Greenwood Village

135 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$139,999

2 beds

1 baths

938 sq ft

House

135 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

The Vineyards at Mount Sinai

59 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$1,075,000

2 beds

4 baths

1,982 sq ft

Condo

59 FARM ACRE CIR, BROOKHAVEN, NY, 11766

Community: The Vineyards at Mount Sinai

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

Questions? Call us: (860) 854-8527

Greenwood Village

21 LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$169,000

2 beds

2 baths

1,100 sq ft

Condo

21 LIMETREE DR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Village

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$349,000

2 beds

1 baths

875 sq ft

Condo

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Village

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$259,990

1 beds

1 baths

684 sq ft

Condo

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Meadow Brook Estates

312 SPRUCE HILL DR 312, OXFORD, CT, 0647..., Oxford, CT 06478

$529,900

2 beds

3 baths

1,564 sq ft

Condo

312 SPRUCE HILL DR 312, OXFORD, CT, 0647...

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

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The Village at Oxford Greens

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

1093 ST ANDREWS DR 7, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (860) 854-8527

Fairview at Oxford Greens

1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478

$739,900

2 beds

3 baths

2,536 sq ft

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$739,900

2 beds

3 baths

2,536 sq ft

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

3 beds

3 baths

2,455 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

3 baths

1,404 sq ft

3 beds

3 baths

2,047 sq ft

Condo

2 beds

2 baths

1,315 sq ft

Condo

3 beds

3 baths

2,107 sq ft

Condo

1 beds

1 baths

750 sq ft

Condo

2 beds

3 baths

2,500 sq ft

Condo

2 beds

2 baths

1,685 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,358 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

3 beds

3 baths

2,455 sq ft

Condo

2 beds

2 baths

1,164 sq ft

Mobile Home

2 beds

3 baths

1,350 sq ft

Condo

2 beds

2 baths

1,670 sq ft

Condo

2 beds

2 baths

1,394 sq ft

House

2 beds

3 baths

1,479 sq ft

Condo

1 beds

1 baths

672 sq ft

Condo

2 beds

1 baths