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

126 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
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
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
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
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 (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
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Want to learn more about 55+ 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
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
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 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.
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Brierly Pond Village
$300ks - $400ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 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
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 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.
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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
Harbor View Estates
$400ks - $600ks
Harbor View Estates, Copiague, NY
New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 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
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 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.
123...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 Country Pointe Preserve 3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$980,000

2 beds

|

3 baths

|

2,389 sq ft

|

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980
New Chatfield Farms 6 WOODLAND PATH 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403
$799,000

3 beds

|

4 baths

|

2,600 sq ft

|

Condo

6 WOODLAND PATH 6, BEACON FALLS, CT, 064...
Community: Chatfield Farms
New The Waterways at Moriches 606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$699,000

2 beds

|

3 baths

|

1,860 sq ft

|

Condo

606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
New Leisure Village 179 VENTRY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$319,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

179 VENTRY CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
New Snug Harbor 117 HARBOR S, BABYLON, NY, 11701, Babylon, NY 11701
$599,990

2 beds

|

2 baths

|

935 sq ft

|

Condo

117 HARBOR S, BABYLON, NY, 11701
Community: Snug Harbor
New Glenwood Village 1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ..., Riverhead, NY 11901
$205,000

2 beds

|

2 baths

|

1,036 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ...
Community: Glenwood Village
New Heritage Village 1003 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

1003 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
New Spring Lake Village 253 CARRIAGE DR 253, SOUTHINGTON, CT, 06..., Southington, CT 06489
$309,900

2 beds

|

2 baths

|

1,152 sq ft

|

Condo

253 CARRIAGE DR 253, SOUTHINGTON, CT, 06...
Community: Spring Lake 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.
New Meadowbrook Pointe Links & Spa 250 SAND HILLS LN, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$324,100

2 beds

|

2 baths

|

1,133 sq ft

|

Condo

250 SAND HILLS LN, BROOKHAVEN, NY, 11763
New Greenwood Village 69 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

69 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Oronoque Village 585 PEQUOT LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$640,000

1 beds

|

3 baths

|

1,583 sq ft

|

Condo

585 PEQUOT LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Encore Atlantic Shores 228 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$749,000

2 beds

|

2 baths

|

1,605 sq ft

|

Condo

228 SONATA CT, BROOKHAVEN, NY, 11941
New Liberty at Newtown 16 FRANKLIN CT 16, NEWTOWN, CT, 06470, Newtown, CT 06470
$599,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

16 FRANKLIN CT 16, NEWTOWN, CT, 06470
Community: Liberty at Newtown
New Oronoque Village 632A OLD KNIFE LN 632A, STRATFORD, CT, 0..., Stratford, CT 06614
$570,000

2 beds

|

3 baths

|

1,876 sq ft

|

Condo

632A OLD KNIFE LN 632A, STRATFORD, CT, 0...
Community: Oronoque Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
New The Villas at Narragansett 406 NARRAGANSETT VILLAS DR, BABYLON, NY,..., Babylon, NY 11757
$599,000

2 beds

|

2 baths

|

1,215 sq ft

|

Condo

406 NARRAGANSETT VILLAS DR, BABYLON, NY,...
New Fairfield at St. James 1203 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$399,000

1 beds

|

1 baths

|

793 sq ft

|

Condo

1203 CABOT CT, SMITHTOWN, NY, 11780
Fairview 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
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
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 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
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
Fairview 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

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
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

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
Fairfield at St. James 302 BENTLEY CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$499,000

2 beds

|

2 baths

|

1,067 sq ft

|

Condo

302 BENTLEY CT, SMITHTOWN, NY, 11780
Encore Atlantic Shores 78 BALLAD CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$925,000

2 beds

|

3 baths

|

2,625 sq ft

|

Condo

78 BALLAD CT, BROOKHAVEN, NY, 11941
Oronoque Village 372 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$389,900

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

372 PIUTE 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
Encore Atlantic Shores 63 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$918,000

2 beds

|

3 baths

|

2,769 sq ft

|

Condo

63 ENCORE BLVD, BROOKHAVEN, NY, 11941
Village Estates 130 FRANCESCA WAY, BABYLON, NY, 11701, Babylon, NY 11701
$639,000

2 beds

|

2 baths

|

1,243 sq ft

|

Condo

130 FRANCESCA WAY, BABYLON, NY, 11701
Community: Village Estates
Eagles Walk at East Quogue 1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11..., Southampton, NY 11942
$565,000

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11...
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.
Leisure Village 231 BLACKPOOL CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

231 BLACKPOOL CT, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Greens at Half Hollow 742 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,099,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

742 VERONA DR, HUNTINGTON, NY, 11747
Country Pointe Plainview 52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803
$1,649,990

2 beds

|

3 baths

|

1,750 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
Encore Atlantic Shores 216 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$899,000

2 beds

|

3 baths

|

2,439 sq ft

|

Condo

216 SONATA CT, BROOKHAVEN, NY, 11941
The Waterways at Moriches 132 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$550,000

2 beds

|

2 baths

|

1,544 sq ft

|

Condo

132 CAPTAINS CT, BROOKHAVEN, NY, 11955
Vineyards at Blue Point 37 HALLEY DR 17, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$660,000

2 beds

|

2 baths

|

1,220 sq ft

|

Condo

37 HALLEY DR 17, BROOKHAVEN, NY, 11772
Angell Brook Village 10 ANGELL BROOK DR 10, WEST BOYLSTON, MA..., West Boylston, MA 01583
$540,000

3 beds

|

2 baths

|

2,228 sq ft

|

Condo

10 ANGELL BROOK DR 10, WEST BOYLSTON, MA...
Newtown Woods 1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064..., Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064...
Community: Newtown Woods
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$600,000

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
Heritage Village 581 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage 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.

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