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

148 communities near Trumbull

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Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
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Questions? Call us: (475) 231-4869
Stoneleigh Woods at Carme...
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
Meadowbrooke Pointe East ...
$500ks - $600ks
Meadowbrooke Pointe East ..., East Meadow, NY
New Construction | 62+ age-restricted | Built 2019 - present | 104 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Autumn Estates
$500ks - $600ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
The Seasons at Plainview
$500ks - $600ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 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 Seasons at East Meado...
$400ks - $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
Hidden Harbor Estates
$500ks - $600ks
Hidden Harbor Estates, Copiague, NY
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes
Bartlett Hollow
$200ks - $400ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
The Vineyards at Mount Si...
$800ks - $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction | 55+ age-restricted | Built 2020 - present | 91 homes
Want to learn more about 55+ communities in Trumbull? 55places can help!
Questions? Call us: (475) 231-4869
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Woodcrest at Jacobs Hill
$200ks - $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 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.
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
RiverWalk
$500ks - $600ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
Glassbury Court at Hunter...
$500ks - $700ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes
Wolfe Landing
$500ks - $600ks
Wolfe Landing, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 43 homes
Want to learn more about 55+ communities in Trumbull? 55places can help!
Questions? Call us: (475) 231-4869
Eden Park
$500ks - $600ks
Eden Park, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes
The Views at Pomona
$200ks - $400ks
The Views at Pomona, Pomona, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 homes
North Woods of Colchester
$300ks - $400ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 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.
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 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
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
The Pines at Bohemia
$400ks - $500ks
The Pines at Bohemia, Bohemia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 20 homes
Castle Heights of Cheshir...
$500ks - $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes
The Polo Club at Islandia
$600ks - $700ks
The Polo Club at Islandia, Islandia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
Want to learn more about 55+ communities in Trumbull? 55places can help!
Questions? Call us: (475) 231-4869
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Windmill Gate
$300ks - $400ks
Windmill Gate, Oakdale, NY
Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 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.
New The Powder Forest Homes 9 ASHTON CIR, SIMSBURY, CT, 06070, Simsbury, CT 06070
$700,000

2 beds

|

2 baths

|

1,809 sq ft

|

Condo

9 ASHTON CIR, SIMSBURY, CT, 06070
New Applegate Estates 90 APPLE GATE 190, SOUTHINGTON, CT, 0648..., Southington, CT 06489
$450,000

2 beds

|

2 baths

|

1,350 sq ft

|

Condo

90 APPLE GATE 190, SOUTHINGTON, CT, 0648...
Community: Applegate Estates
New The Village at Oxford Greens 71 LINKS WAY 71, OXFORD, CT, 06478, Oxford, CT 06478
$598,000

2 beds

|

2 baths

|

1,590 sq ft

|

Condo

71 LINKS WAY 71, OXFORD, CT, 06478
New The Greens at Half Hollow 1153 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$750,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

1153 SAVOY DR, HUNTINGTON, NY, 11747
New Heritage Village 397 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$264,999

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Trumbull? 55places can help!
Questions? Call us: (475) 231-4869
New Regency at Fishkill 145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$539,999

2 beds

|

2 baths

|

1,803 sq ft

|

Condo

145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
New The Waterways at Moriches 377 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$599,999

2 beds

|

2 baths

|

2,141 sq ft

|

Condo

377 QUARRY POND CT, BROOKHAVEN, NY, 1195...
New Woodridge Strathmore Terrace 58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$435,000

2 beds

|

2 baths

|

1,025 sq ft

|

Condo

58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
New Jefferson Village 113 VILLAGE RD B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$449,999

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

113 VILLAGE RD B, YORKTOWN, NY, 10598
Community: Jefferson Village
New The Woods at Dunham Pond 29 HERON VIEW RD 29, NEW FAIRFIELD, CT, ..., New Fairfield, CT 06812
$334,000

1 beds

|

2 baths

|

1,590 sq ft

|

Condo

29 HERON VIEW RD 29, NEW FAIRFIELD, CT, ...
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 Heritage Hills 37 HERITAGE HILLS DR A, SOMERS, NY, 1058..., Somers, NY 10589
$500,000

1 beds

|

1 baths

|

955 sq ft

|

Condo

37 HERITAGE HILLS DR A, SOMERS, NY, 1058...
Community: Heritage Hills
New Greenwood Village 131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$165,000

2 beds

|

2 baths

|

1,062 sq ft

|

Manufactured Home

131 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Shadow Lake Village 65 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$339,999

1 beds

|

1 baths

|

979 sq ft

|

Adult Community

65 LEXINGTON CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
New The Waterways at Moriches 629 WATER WAY 29, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$715,000

2 beds

|

3 baths

|

1,611 sq ft

|

Condo

629 WATER WAY 29, BROOKHAVEN, NY, 11955
New Regency Meadows 108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611
$739,000

2 beds

|

3 baths

|

2,891 sq ft

|

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611
Community: Regency Meadows
New Heritage Hills 757 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$569,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

757 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Trumbull? 55places can help!
Questions? Call us: (475) 231-4869
New Four Seasons at Ridgemont 602 FOUR SEASONS LN, MONTVALE, NJ, 07645, Montvale, NJ 07645
$915,000

2 beds

|

2 baths

|

Condo

602 FOUR SEASONS LN, MONTVALE, NJ, 07645
New Heritage Village 139 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Regency at Fishkill 246 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$499,999

1 beds

|

2 baths

|

1,543 sq ft

|

Condo

246 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
New Foxwood Village 1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933, Brookhaven, NY 11933
$425,000

2 beds

|

2 baths

|

1,444 sq ft

|

Manufactured Home

1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933
Community: Foxwood 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 Heritage Village 738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$365,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 69 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

69 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 122 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$354,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

122 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 47 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$324,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

47 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Knoll 491 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$489,000

2 beds

|

2 baths

|

976 sq ft

|

Condo

491 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 553 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

553 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Jefferson Village 23 DORSET CT F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$315,000

2 beds

|

1 baths

|

925 sq ft

|

Condo

23 DORSET CT F, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in Trumbull? 55places can help!
Questions? Call us: (475) 231-4869
Country Village Estates 41 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$480,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

41 THEODORE DR, BROOKHAVEN, NY, 11727
Oronoque Village 664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

664 OSAGE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Shadow Lake Village 34 DICKINSON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$559,000

2 beds

|

2 baths

|

1,272 sq ft

|

House

34 DICKINSON CT, RED BANK, NJ, 07701
Community: Shadow 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.
Heritage Village 69 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$270,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

69 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Shadow Lake Village 17 BELMONT CT D, RED BANK, NJ, 07701, Red Bank, NJ 07701
$369,000

1 beds

|

1 baths

|

930 sq ft

|

House

17 BELMONT CT D, RED BANK, NJ, 07701
Community: Shadow Lake Village
Plymouth Estates at Mount Sinai 98 ANDREW DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,990

2 beds

|

2 baths

|

1,820 sq ft

|

Condo

98 ANDREW DR, BROOKHAVEN, NY, 11766
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Fishkill 326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$519,000

1 beds

|

2 baths

|

1,543 sq ft

|

Condo

326 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$575,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Jefferson Village 80 C INDEPENDENCE CT, YORKTOWN, NY, 1059..., Yorktown, NY 10598
$359,000

1 beds

|

1 baths

|

850 sq ft

|

Condo

80 C INDEPENDENCE CT, YORKTOWN, NY, 1059...
Community: Jefferson Village
Plymouth Estates at Mount Sinai 26 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$595,000

2 beds

|

2 baths

|

1,563 sq ft

|

Condo

26 ROSE LN, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in Trumbull? 55places can help!
Questions? Call us: (475) 231-4869
Heritage Village 2 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$357,500

2 beds

|

2 baths

|

1,572 sq ft

|

Condo

2 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 567 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$469,900

1 beds

|

2 baths

|

967 sq ft

|

Condo

567 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
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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