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Middlebury, CT 55+ active adult communities & homes for sale - Page 7

326 homes near Middlebury

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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
4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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.
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 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
5 rating (1 reviews) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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.
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Glassbury Court at Cold S...
$500ks - $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 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.
4 rating (1 reviews) Vineyards at Blue Point
$500ks - $700ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 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
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
The Views at Pomona
$200ks - $400ks
The Views at Pomona, Pomona, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 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
Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
Encore Atlantic Shores 11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$885,000

2 beds

|

3 baths

|

2,900 sq ft

|

Condo

11 OVATION PL, BROOKHAVEN, NY, 11941
Heritage Village 184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 22 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$425,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

22 CRICKET CT, BROOKHAVEN, NY, 11967
Heritage Village 333 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

333 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Heritage Hills 103 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$780,000

3 beds

|

2 baths

|

1,780 sq ft

|

Condo

103 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Country Pointe Plainview 33204 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803
$1,599,999

2 beds

|

2 baths

|

1,976 sq ft

|

Condo

33204 SPRUCE POND CIR, OYSTER BAY, NY, 1...
Hopmeadow Place 1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,430 sq ft

|

Condo

1 W ST 310, SIMSBURY, CT, 06070
Community: Hopmeadow Place
The Bel Aire at East Meadow 50 MERRICK AVE 415, HEMPSTEAD, NY, 11554, Hempstead, NY 11554
$500,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

50 MERRICK AVE 415, HEMPSTEAD, NY, 11554
HarborView 100 HARBOR VIEW DR 251, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$829,000

2 beds

|

3 baths

|

Condo

100 HARBOR VIEW DR 251, NORTH HEMPSTEAD,...
Community: HarborView
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.
Oronoque Village 448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$525,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
Saddle Lakes 174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$649,000

2 beds

|

2 baths

|

1,631 sq ft

|

Condo

174 ADELE CT, RIVERHEAD, NY, 11901
Community: Saddle Lakes
Newtown Woods 832 BROOKSIDE CT 832, NEWTOWN, CT, 06470, Newtown, CT 06470
$585,000

2 beds

|

2 baths

|

1,807 sq ft

|

Condo

832 BROOKSIDE CT 832, NEWTOWN, CT, 06470
Community: Newtown Woods
Westhampton Pines 171 JONATHAN LN, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$1,345,000

3 beds

|

3 baths

|

2,310 sq ft

|

Condo

171 JONATHAN LN, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
Meadowbrook Pointe Links & Spa 163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176..., Brookhaven, NY 11763
$699,990

2 beds

|

3 baths

|

1,558 sq ft

|

Condo

163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176...
Dutchgate 212 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580
$515,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

212 WILLOW LN, HEMPSTEAD, NY, 11580
Community: Dutchgate
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Heritage Village 945 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$398,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

945 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Vineyards at Brookfield 104 ARI LN, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$869,000

2 beds

|

4 baths

|

2,718 sq ft

|

Condo

104 ARI LN, BROOKHAVEN, NY, 11934
Stone Ridge Estates 160 CHRISTINE DR, HUNTINGTON, NY, 11746, Huntington, NY 11746
$770,000

2 beds

|

2 baths

|

Condo

160 CHRISTINE DR, HUNTINGTON, NY, 11746
Community: Stone Ridge Estates
Country Village Estates 110 THEODORE DR 110, BROOKHAVEN, NY, 117..., Brookhaven, NY 11727
$475,000

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

110 THEODORE DR 110, BROOKHAVEN, NY, 117...
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 Powder Forest Homes 15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070
$899,000

4 beds

|

3 baths

|

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070
Oronoque Village 283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$625,000

2 beds

|

3 baths

|

1,415 sq ft

|

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$353,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Liberty at Newtown 49 JO AL CT 49, NEWTOWN, CT, 06470, Newtown, CT 06470
$619,000

2 beds

|

3 baths

|

2,341 sq ft

|

Condo

49 JO AL CT 49, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Heritage Village 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 59 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

59 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$539,000

2 beds

|

3 baths

|

2,542 sq ft

|

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Liberty at Newtown 25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470
$529,000

2 beds

|

2 baths

|

1,413 sq ft

|

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Heritage Hills 300 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$555,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

300 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Leisure Knoll 183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$415,000

2 beds

|

1 baths

|

960 sq ft

|

Condo

183 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
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 Village at Oxford Greens 527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478
$650,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...
Regency at Fishkill 811 REGENCY DR 802, FISHKILL, NY, 12524, Fishkill, NY 12524
$161,450

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

811 REGENCY DR 802, FISHKILL, NY, 12524
Community: Regency at Fishkill
The Waterways at Moriches 376 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$499,999

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

376 QUARRY POND CT, BROOKHAVEN, NY, 1195...
Country Pointe Plainview 15103 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$1,050,000

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

15103 ASPENWOOD DR, OYSTER BAY, NY, 1180...
Jefferson Village 51 JEFFERSON OVAL E, YORKTOWN, NY, 10598, Yorktown, NY 10598
$439,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

51 JEFFERSON OVAL E, YORKTOWN, NY, 10598
Community: Jefferson Village
Harbor View Estates 206 ANCHOR CT, BABYLON, NY, 11726, Babylon, NY 11726
$589,990

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

206 ANCHOR CT, BABYLON, NY, 11726
Community: Harbor View Estates
Heritage Village 411 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$449,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 101 HERITAGE HILLS DR A, SOMERS, NY, 105..., Somers, NY 10589
$649,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

101 HERITAGE HILLS DR A, SOMERS, NY, 105...
Community: Heritage Hills
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Oronoque Village 13 ALGONQUIN LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$396,000

1 beds

|

2 baths

|

1,480 sq ft

|

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Summit at Bethel 6 LOCKWOOD CIR 6, BETHEL, CT, 06801, Bethel, CT 06801
$599,000

3 beds

|

3 baths

|

1,771 sq ft

|

Condo

6 LOCKWOOD CIR 6, BETHEL, CT, 06801
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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