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Middletown, CT 55+ active adult communities & homes for sale - Page 3

127 communities near Middletown

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4.9 rating (14 reviews) Chatfield Farms
$400ks - $700ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
North Woods of Colchester
$300ks - $400ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
RiverWalk
$500ks - $600ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
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Questions? Call us: (860) 854-8527
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Bartlett Hollow
$200ks - $400ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
Autumn Estates
$500ks - $600ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 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.
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
RiverBend Estates
$400ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Summer Wind Estates
$300ks - $400ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 homes
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Cobblestone Court
$400ks - $500ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes
Forest Mews
$300ks - $400ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
The Village at Hunt Glen
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
O'Meara Farm
$400ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 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.
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
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
Angell Brook Village
$300ks
Angell Brook Village, West Boylston, MA
Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
New England Commons
$200ks - $300ks
New England Commons, Webster, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
The Woods at Dunham Pond
$200ks - $400ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 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 Coach Homes at Ridgef...
$300ks - $400ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 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
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Windmill Gate
$300ks - $400ks
Windmill Gate, Oakdale, NY
Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
3.5 rating (2 reviews) Harvest Pointe
$800ks - $3Ms
Harvest Pointe, Cutchogue, NY
New Construction | 55+ age-restricted | Built 2017 - present | 124 homes
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 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.
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
$410,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Heritage Village 40 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$270,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

40 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 28 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$429,900

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

28 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Summit at Bethel 14 GREAT HILL DR 14, BETHEL, CT, 06801, Bethel, CT 06801
$719,000

3 beds

|

3 baths

|

2,744 sq ft

|

Condo

14 GREAT HILL DR 14, BETHEL, CT, 06801
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
New Village Estates 121 FRANCESCA WAY, BABYLON, NY, 11701, Babylon, NY 11701
$559,000

2 beds

|

1 baths

|

1,234 sq ft

|

Condo

121 FRANCESCA WAY, BABYLON, NY, 11701
Community: Village Estates
New Oronoque Village 615 CHEROKEE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$574,900

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

615 CHEROKEE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Harbor View Estates 301 ANCHOR CT, BABYLON, NY, 11726, Babylon, NY 11726
$625,000

1 beds

|

2 baths

|

1,213 sq ft

|

Condo

301 ANCHOR CT, BABYLON, NY, 11726
Community: Harbor View Estates
New The Waterways at Moriches 606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$749,000

2 beds

|

3 baths

|

1,860 sq ft

|

Condo

606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195...
New Founders Ridge UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT..., Middletown, CT 06457
$689,000

2 beds

|

2 baths

|

1,555 sq ft

UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT...
Community: Founders Ridge
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 Leisure Glen 20 WAINSCOTT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$599,999

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

20 WAINSCOTT CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Brierly Pond Village 97 HORNE WAY 97, MILLBURY, MA, 01527, Millbury, MA 01527
$450,000

2 beds

|

3 baths

|

1,746 sq ft

|

Condo

97 HORNE WAY 97, MILLBURY, MA, 01527
New Leisure Glen 9 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$619,000

2 beds

|

2 baths

|

1,882 sq ft

|

House

9 OAKDALE CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Country Pointe Plainview 43101 SILVER BIRCH LN, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803
$1,750,000

2 beds

|

2 baths

|

2,178 sq ft

|

House

43101 SILVER BIRCH LN, OYSTER BAY, NY, 1...
New Sunrise Village 97 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$519,000

2 beds

|

2 baths

|

1,046 sq ft

|

Condo

97 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
New Strathmore Gate East 39 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$375,000

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

39 FREEMONT LN, BROOKHAVEN, NY, 11727
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
New Fairfield at St. James 704 FENWAY RD, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$519,000

2 beds

|

2 baths

|

1,292 sq ft

|

Condo

704 FENWAY RD, SMITHTOWN, NY, 11780
The Village at Oxford Greens 84 LINKS WAY 84, OXFORD, CT, 06478, Oxford, CT 06478
$710,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

84 LINKS WAY 84, OXFORD, CT, 06478
Autumn Fields 24 QUAIL HOLW 24, ENFIELD, CT, 06082, Enfield, CT 06082
$339,000

1 beds

|

2 baths

|

1,235 sq ft

|

Condo

24 QUAIL HOLW 24, ENFIELD, CT, 06082
Community: Autumn Fields
Heritage Village 722 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

722 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.
Country Pointe Plainview 30101 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803
$1,200,000

2 beds

|

2 baths

|

1,379 sq ft

|

Condo

30101 SPRUCE POND CIR, OYSTER BAY, NY, 1...
Heritage Village 970 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$309,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

970 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 44 WARRINGTON ROUND 44, DANBURY, CT, 068..., Danbury, CT 06810
$628,000

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

44 WARRINGTON ROUND 44, DANBURY, CT, 068...
Community: Rivington
Leisure Glen 477 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$589,000

2 beds

|

2 baths

|

1,434 sq ft

|

Condo

477 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Country Pointe Plainview 38204 WINTERBERRY DR, OYSTER BAY, NY, 11..., Oyster Bay, NY 11803
$1,585,000

2 beds

|

2 baths

|

1,989 sq ft

|

Condo

38204 WINTERBERRY DR, OYSTER BAY, NY, 11...
The Manors at The Colony Preserve 41 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$485,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

41 GREENTREE CT, BROOKHAVEN, NY, 11967
Heritage Village 411 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$427,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Heritage Village 620 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$319,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Country Pointe Preserve 119 MIA LN 76, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$940,000

2 beds

|

3 baths

|

2,187 sq ft

|

Condo

119 MIA LN 76, BROOKHAVEN, NY, 11980
The Village at Oxford Greens 733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478
$624,900

2 beds

|

3 baths

|

1,673 sq ft

|

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...
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.
Sunken Pond Estates 403 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$520,000

2 beds

|

2 baths

|

1,350 sq ft

|

Condo

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190...
Community: Sunken Pond Estates
Saddle Lakes 157 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$595,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
Village Estates 30 SARAH CT, BABYLON, NY, 11701, Babylon, NY 11701
$599,000

2 beds

|

2 baths

|

1,251 sq ft

|

Condo

30 SARAH CT, BABYLON, NY, 11701
Community: Village Estates
The Greens at Half Hollow 643 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,299,999

3 beds

|

3 baths

|

2,500 sq ft

|

Condo

643 VERONA DR, HUNTINGTON, NY, 11747
Regency at Prospect 133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712
$550,000

2 beds

|

3 baths

|

1,850 sq ft

|

Condo

133 SYCAMORE DR, PROSPECT, CT, 06712
Community: Regency at Prospect
Vineyards at Moriches 19 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$775,000

2 beds

|

3 baths

|

2,251 sq ft

|

Condo

19 EMILIE DR, BROOKHAVEN, NY, 11934
Leisure Glen 279 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$569,999

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

279 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Newtown Woods 623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470
$498,900

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470
Community: Newtown Woods
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Heritage Village 875 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

875 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Buckingham 13 KENINGTON RD 13, AVON, CT, 06001, Avon, CT 06001
$639,900

3 beds

|

3 baths

|

2,024 sq ft

|

Condo

13 KENINGTON RD 13, AVON, CT, 06001
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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