Call us at (860) 854-8527 to learn more about active adult communities in Middletown

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

121 communities near Middletown

Sort by:

Relevance

Relevance

5 rating (3 reviews) Founders Ridge
$500Ks - $600Ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
No reviews yet Sonoma Woods
$300Ks - $300Ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
No reviews yet Bartlett Hollow
$200Ks - $400Ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
3.6 rating (7 reviews) Heritage Village
$100Ks - $400Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
No reviews yet Leisure Village
$200Ks - $500Ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
No reviews yet 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
No reviews yet Rivington
$400Ks - $900Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
No reviews yet Oronoque Village
$400Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
No reviews yet 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
No reviews yet Leisure Knoll
$400Ks - $500Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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.
No reviews yet Country Pointe Plainview
$1Ms - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (1 reviews) Fairfield at St. James
$400Ks - $600Ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
No reviews yet Leisure Glen
$400Ks - $500Ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
No reviews yet Spring Lake Village
$200Ks - $200Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
4 rating (8 reviews) Glenwood Village
$100Ks - $400Ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
3.7 rating (3 reviews) Greenwood Village
$100Ks - $200Ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
No reviews yet The Seasons at East Meado...
$500Ks - $500Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
No reviews yet Regency at Prospect
$400Ks - $400Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
No reviews yet The Waterways at Moriches
$400Ks - $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.5 rating (2 reviews) Foxwood Village
$300Ks - $400Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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.
1 rating (1 reviews) Plymouth Estates at Mount...
$500Ks - $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$600Ks - $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
4 rating (1 reviews) Vineyards at Blue Point
$600Ks - $900Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
No reviews yet The Club at Melville
$500Ks - $500Ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
No reviews yet The Seasons at Elwood
$800Ks - $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
No reviews yet Meadow Brook Estates
$500Ks - $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
5 rating (1 reviews) Encore Atlantic Shores
$600Ks - $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
No reviews yet The Summit at Bethel
$600Ks - $600Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks - $500Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 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
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.
No reviews yet Woodridge Strathmore Terr...
$400Ks - $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
5 rating (1 reviews) Sunrise Village
$400Ks - $400Ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
No reviews yet Brierly Pond Village
$400Ks - $400Ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
No reviews yet Saddle Lakes
$400Ks - $400Ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
No reviews yet Country Village Estates
$400Ks - $500Ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
5 rating (1 reviews) Sunken Pond Estates
$400Ks - $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
5 rating (1 reviews) Westhampton Pines
$900Ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 reviews) The Villages at Mount Sin...
$700Ks - $800Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
No reviews yet The Powder Forest Homes
$600Ks - $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
5 rating (1 reviews) Newtown Woods
$400Ks - $500Ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Harmony Place 6 FIDELITY DR # 2, RUTLAND, MA, 01543, Rutland, MA 01543
$512,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

6 FIDELITY DR # 2, RUTLAND, MA, 01543
Community: Harmony Place
New Harmony Place 4 FIDELITY DR # 2, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

4 FIDELITY DR # 2, RUTLAND, MA, 01543
Community: Harmony Place
New Harmony Place 132 FIDELITY DR # 61, RUTLAND, MA, 01543, Rutland, MA 01543
$539,000

2 beds

|

2 baths

|

2,149 sq ft

|

Condo

132 FIDELITY DR # 61, RUTLAND, MA, 01543
Community: Harmony Place
Brierly Pond Village 30 HORNE WAY # 30, MILLBURY, MA, 01527, Millbury, MA 01527
$419,900

3 beds

|

2 baths

|

1,746 sq ft

|

Condo

30 HORNE WAY # 30, MILLBURY, MA, 01527
The Gardens of Wilbraham 45 IVY CIR # 45, WILBRAHAM, MA, 01095, Wilbraham, MA 01095
$495,000

2 beds

|

3 baths

|

1,752 sq ft

|

Condo

45 IVY CIR # 45, WILBRAHAM, MA, 01095
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Brierly Pond Village 47 HORNE WAY # 47, MILLBURY, MA, 01527, Millbury, MA 01527
$454,000

2 beds

|

3 baths

|

1,746 sq ft

|

Condo

47 HORNE WAY # 47, MILLBURY, MA, 01527
Leisure Village 406 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961
$235,500

1 beds

|

1 baths

|

679 sq ft

|

Condo

406 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ..., Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

975 sq ft

|

Condo

369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ...
Community: Leisure Village
Greenwood Village 5157 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$189,500

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

5157 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 137 EASTBOURNE CT A, RIDGE, NY, 11961, Ridge, NY 11961
$299,999

2 beds

|

1 baths

|

836 sq ft

|

Condo

137 EASTBOURNE CT A, RIDGE, NY, 11961
Community: Leisure Village
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 Waterways at Moriches 521 HIGHLAND CT # 521, MORICHES, NY, 119..., Moriches, NY 11955
$610,000

2 beds

|

2 baths

|

1,839 sq ft

|

Condo

521 HIGHLAND CT # 521, MORICHES, NY, 119...
Fairfield at St. James 1104 DREW DR, SAINT JAMES, NY, 11780, Saint James, NY 11780
$429,000

1 beds

|

1 baths

|

752 sq ft

|

Condo

1104 DREW DR, SAINT JAMES, NY, 11780
Country Village Estates 11 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727
$479,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

11 THEODORE DR, CORAM, NY, 11727
Glenwood Village 1661 OLD COUNTRY RD UNIT 423, RIVERHEAD,..., Riverhead, NY 11901
$199,900

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 423, RIVERHEAD,...
Community: Glenwood Village
New The Greens at Half Hollow 708 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747
$1,299,999

3 beds

|

3 baths

|

2,500 sq ft

|

Condo

708 BALFOUR PL, MELVILLE, NY, 11747
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
New Leisure Glen 475 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961
$549,000

2 beds

|

2 baths

|

1,417 sq ft

|

Condo

475 LEISURE DR, RIDGE, NY, 11961
Community: Leisure Glen
Glenwood Village 1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ..., Riverhead, NY 11901
$299,500

2 beds

|

2 baths

|

1,270 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ...
Community: Glenwood Village
Fairfield at St. James 205 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$619,990

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

205 FLAIR CT, SMITHTOWN, NY, 11780
Leisure Village 96 ENFIELD CT B, RIDGE, NY, 11961, Ridge, NY 11961
$459,000

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

96 ENFIELD CT B, RIDGE, NY, 11961
Community: Leisure Village
Encore Atlantic Shores 68 ENCORE, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$849,999

2 beds

|

3 baths

|

3,000 sq ft

|

Condo

68 ENCORE, BROOKHAVEN, NY, 11941
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.
Greenwood Village 77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$159,990

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

77 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Sunrise Village 133 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782
$439,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

133 REVERE DR, SAYVILLE, NY, 11782
Community: Sunrise Village
Stone Ridge Estates 156 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746
$800,000

2 beds

|

2 baths

|

1,700 sq ft

|

Condo

156 CHRISTINE DR, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
New Greenwood Village 164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$174,990

2 beds

|

1 baths

|

938 sq ft

|

Manufactured Home

164 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
New Fairfield at St. James 914 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780
$499,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

914 FENWAY RD, SAINT JAMES, NY, 11780
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
New The Villages at Mount Sinai Park 109 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$749,900

2 beds

|

2 baths

|

1,736 sq ft

|

Condo

109 LOUDEN LOOP, MOUNT SINAI, NY, 11766
New The Waterways at Moriches 365 SEABREEZE CT, MORICHES, NY, 11955, Moriches, NY 11955
$595,000

2 beds

|

2 baths

|

1,930 sq ft

|

Condo

365 SEABREEZE CT, MORICHES, NY, 11955
New Leisure Village 2 GUILFORD CT B, RIDGE, NY, 11961, Ridge, NY 11961
$519,000

2 beds

|

2 baths

|

1,767 sq ft

|

Condo

2 GUILFORD CT B, RIDGE, NY, 11961
Community: Leisure Village
Glenwood Village 1661 OLD COUNTRY RD 179, RIVERHEAD, NY, ..., Riverhead, NY 11901
$215,000

2 beds

|

2 baths

|

1,036 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 179, RIVERHEAD, NY, ...
Community: Glenwood Village
Greenwood Village 21 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949
$179,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

21 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
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 East Meadow 121 SPRING DR # 121, EAST MEADOW, NY, 11..., East Meadow, NY 11554
$579,999

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

121 SPRING DR # 121, EAST MEADOW, NY, 11...
Meadowbrook Pointe Links & Spa 142 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763
$729,990

2 beds

|

3 baths

|

1,691 sq ft

|

Condo

142 AUGUSTA DR, MEDFORD, NY, 11763
New Kensington Estates 46 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797
$2,999,999

6 beds

|

5 baths

|

4,333 sq ft

|

House

46 PLAINVIEW RD, WOODBURY, NY, 11797
Community: Kensington Estates
Leisure Village 42D TRENT CT 42D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$249,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

42D TRENT CT 42D, BROOKHAVEN, NY, 11961
Community: Leisure Village
New Fairfield at St. James 605 CABOT CT 605, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$499,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

605 CABOT CT 605, SMITHTOWN, NY, 11780
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Leisure Knoll 145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961
$415,000

2 beds

|

2 baths

|

900 sq ft

|

Condo

145 EDINBURGH DR, RIDGE, NY, 11961
Community: Leisure Knoll
Leisure Village 192 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961
$239,000

1 beds

|

1 baths

|

650 sq ft

|

Condo

192 VENTRY CT A, RIDGE, NY, 11961
Community: Leisure Village
The Seasons at East Meadow 315 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$584,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

315 SPRING DR, EAST MEADOW, NY, 11554
Village Estates 26 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701
$549,000

2 beds

|

2 baths

|

1,243 sq ft

|

Condo

26 SARAH CT, AMITYVILLE, NY, 11701
Community: Village Estates
New Glenwood Village 1661 OLD COUNTRY RD 540, RIVERHEAD, NY, ..., Riverhead, NY 11901
$425,000

2 beds

|

2 baths

|

1,700 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 540, RIVERHEAD, NY, ...
Community: Glenwood Village

Frequently Asked Questions


Want more information about active adult communities around Middletown?

Global - Lead Form - Buyer or Renter

*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

121 communities near Middletown
Remove Boundaries ×
Map Satellite

Want to learn more about 55+ communities in Middletown?

Call us: (860) 854-8527

Call Us Call Us
Scroll to Top