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

125 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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

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

Questions? Call us: (860) 854-8527

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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 Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

$300ks - $900ks

Rivington, Danbury, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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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

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

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

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Questions? Call us: (860) 854-8527

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

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Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes

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Questions? Call us: (860) 854-8527

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

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

Questions? Call us: (860) 854-8527

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

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

1 2 3...4

New Heritage Village

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

$189,000

2 beds

2 baths

1,044 sq ft

Condo

331 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Angell Brook Village

44 ANGELL BROOK DR 44, WEST BOYLSTON, MA..., West Boylston, MA 01583

$479,000

2 beds

2 baths

1,274 sq ft

Condo

44 ANGELL BROOK DR 44, WEST BOYLSTON, MA...

Community: Angell Brook Village

New The Village at Westminster Place

53 TEA PARTY CIR 53, HOLDEN, MA, 01520, Holden, MA 01520

$539,000

2 beds

2 baths

1,258 sq ft

Condo

53 TEA PARTY CIR 53, HOLDEN, MA, 01520

Community: The Village at Westminster Place

New Heritage Village

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

$260,000

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Country Pointe Preserve

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$865,000

2 beds

3 baths

1,998 sq ft

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

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

New Oronoque Village

99 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,426 sq ft

Condo

99 SEMINOLE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Oronoque Village

89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$340,000

1 beds

3 baths

1,438 sq ft

Condo

89 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New The Waterways at Moriches

290 W MIDLAND POND CT 290, BROOKHAVEN, N..., Brookhaven, NY 11955

$629,000

2 beds

2 baths

1,440 sq ft

Condo

290 W MIDLAND POND CT 290, BROOKHAVEN, N...

Community: The Waterways at Moriches

New The Seasons at Seaford

56 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783

$820,000

2 beds

3 baths

1,034 sq ft

Condo

56 SPRING DR, HEMPSTEAD, NY, 11783

Community: The Seasons at Seaford

New Country Pointe Plainview

31201 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,150,000

2 beds

2 baths

1,379 sq ft

Condo

31201 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

Heritage Village

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

$279,000

2 beds

2 baths

1,432 sq ft

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

196 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$365,000

1 beds

2 baths

1,175 sq ft

Condo

196 APACHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Autumn Fields

5 QUAIL HOLW 5, ENFIELD, CT, 06082, Enfield, CT 06082

$399,900

2 beds

3 baths

1,679 sq ft

Condo

5 QUAIL HOLW 5, ENFIELD, CT, 06082

Community: Autumn Fields

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

Questions? Call us: (860) 854-8527

Sunrise Village

93 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$525,000

2 beds

2 baths

1,230 sq ft

Condo

93 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

The Villages at Mount Sinai Park

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$899,000

3 beds

3 baths

2,455 sq ft

House

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

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

Questions? Call us: (860) 854-8527

O'Meara Farm

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032

$480,000

2 beds

2 baths

1,416 sq ft

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032

Community: O'Meara Farm

The Greens at Half Hollow

625 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$980,000

2 beds

3 baths

1,940 sq ft

Condo

625 MADEIRA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Meadowbrooke Pointe East Meadow

137 EMANUEL WAY, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$839,000

2 beds

3 baths

1,390 sq ft

Condo

137 EMANUEL WAY, HEMPSTEAD, NY, 11554

Community: Meadowbrooke Pointe East Meadow

Foxwood Village

1407 MIDDLE RD 91, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$364,000

2 beds

2 baths

1,532 sq ft

House

1407 MIDDLE RD 91, RIVERHEAD, NY, 11933

Community: Foxwood Village

Heritage Village

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

$360,000

2 beds

2 baths

1,432 sq ft

Condo

640 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$409,000

2 beds

2 baths

1,360 sq ft

Condo

47 HURON LN A, 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

279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$299,999

2 beds

1 baths

875 sq ft

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Country Village Estates

45 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$475,000

2 beds

2 baths

1,305 sq ft

Condo

45 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

The Villages at Mount Sinai Park

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$675,000

2 beds

3 baths

1,736 sq ft

House

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Regency at Prospect

104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712

$328,417

3 beds

2 baths

1,500 sq ft

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712

Community: Regency at Prospect

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

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Rivington

131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810

$770,000

3 beds

3 baths

1,592 sq ft

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...

Community: Rivington

Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

Castle Heights of Cheshire

151 VICTORIA DR, CHESHIRE, CT, 06410, Cheshire, CT 06410

$769,900

2 beds

4 baths

2,843 sq ft

Condo

151 VICTORIA DR, CHESHIRE, CT, 06410

Community: Castle Heights of Cheshire

Country Village Estates

163 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$454,500

2 beds

2 baths

1,261 sq ft

Condo

163 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

The Waterways at Moriches

188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$775,000

2 beds

2 baths

2,100 sq ft

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

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Glenwood Village

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ..., Riverhead, NY 11901

$130,000

2 beds

1 baths

720 sq ft

Manufactured Home

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Village

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

$229,000

2 beds

2 baths

1,076 sq ft

Condo

101 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$325,000

2 beds

2 baths

1,076 sq ft

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Eagles Walk at East Quogue

1504 AERIE WAY 1504, SOUTHAMPTON, NY, 11..., Southampton, NY 11942

$545,000

2 beds

2 baths

1,341 sq ft

House

1504 AERIE WAY 1504, SOUTHAMPTON, NY, 11...

Community: Eagles Walk at East Quogue

The Summit at Bethel

20 GREAT HILL DR 20, BETHEL, CT, 06801, Bethel, CT 06801

$649,000

3 beds

3 baths

2,159 sq ft

Condo

20 GREAT HILL DR 20, BETHEL, CT, 06801

Community: The Summit at Bethel

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Heritage Village

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

$353,000

2 beds

2 baths

1,432 sq ft

Condo

401 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Strathmore Gate East

42 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$425,000

2 beds

2 baths

1,112 sq ft

Condo

42 FREEMONT LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

Leisure Glen

16 HUNTINGTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$505,000

2 beds

2 baths

1,312 sq ft

Condo

16 HUNTINGTON CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (860) 854-8527

Heritage Village

25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$439,900

2 beds

2 baths

1,447 sq ft

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Sunken Pond Estates

3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$499,000

2 beds

2 baths

1,587 sq ft

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901

Community: Sunken Pond Estates

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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125 communities

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

125 communities near Middletown

207 homes near Middletown

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,274 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

1,998 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,440 sq ft

Condo

2 beds

3 baths

1,034 sq ft

Condo

2 beds

2 baths

1,379 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

2 beds

3 baths

1,679 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

3 beds

3 baths

2,455 sq ft

House

2 beds

2 baths

1,416 sq ft

Condo

2 beds

3 baths

1,940 sq ft

Condo

2 beds

3 baths

1,390 sq ft

Condo

2 beds

2 baths

1,532 sq ft

House

2 beds