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

287 homes near Middlebury

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5 rating (2 reviews) Benson Woods
$400Ks - $600Ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
No reviews yet Granite Woods
$600Ks - $700Ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
3 rating (2 reviews) Heritage Hills
$400Ks - $600Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1975 - 2003 | 2,600 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 - $400Ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
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 - $1Ms
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$300Ks - $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
No reviews yet Oronoque Village
$500Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
No reviews yet The Village at Oxford Gre...
$500Ks - $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 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 Meadowbrook Pointe Athlet...
$800Ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
No reviews yet Leisure Knoll
$300Ks - $500Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
No reviews yet Country Pointe Plainview
$800Ks - $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 - $500Ks
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
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
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 - $300Ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
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 - $600Ks
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
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 Dutchgate
$400Ks - $400Ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 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
No reviews yet The Retreat at Carmel
$300Ks - $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
3.5 rating (2 reviews) Foxwood Village
$300Ks - $400Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
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
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
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
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
No reviews yet HarborView
$900Ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 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
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 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
$700Ks - $800Ks
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 - $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
No reviews yet Woodridge Strathmore Terr...
$300Ks - $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
No reviews yet Regency at Wappinger
$700Ks - $800Ks
Regency at Wappinger, Wappingers Falls, NY
New and Resale | 55+ age-restricted | Built 2014 - present | 225 homes
5 rating (1 reviews) Sunrise Village
$400Ks - $500Ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 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 - $400Ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Meadowbrook Pointe Links & Spa 42 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763
$649,990

2 beds

|

3 baths

|

1,534 sq ft

|

Condo

42 AUGUSTA DR, MEDFORD, NY, 11763
Westhampton Pines 42 KIMBERLY DR # 42, WESTHAMPTON, NY, 11..., Westhampton, NY 11977
$1,450,000

2 beds

|

3 baths

|

2,350 sq ft

|

Condo

42 KIMBERLY DR # 42, WESTHAMPTON, NY, 11...
Community: Westhampton Pines
Encore at Lake Grove 10 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755
$630,000

2 beds

|

2 baths

|

1,390 sq ft

|

Condo

10 SYMPHONY DR, LAKE GROVE, NY, 11755
Encore Atlantic Shores 82 BALLAD CT, EASTPORT, NY, 11941, Eastport, NY 11941
$795,000

2 beds

|

3 baths

|

2,150 sq ft

|

Condo

82 BALLAD CT, EASTPORT, NY, 11941
Westhampton Pines 69 SAMANTHA CIR # 69, WESTHAMPTON, NY, 1..., Westhampton, NY 11977
$998,999

2 beds

|

2 baths

|

1,944 sq ft

|

Condo

69 SAMANTHA CIR # 69, WESTHAMPTON, NY, 1...
Community: Westhampton Pines
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Heritage Hills 480 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$649,000

2 beds

|

2 baths

|

1,468 sq ft

|

Condo

480 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
The Greens at Half Hollow 1069 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747
$688,500

2 beds

|

2 baths

|

1,140 sq ft

|

Condo

1069 SAVOY DR, MELVILLE, NY, 11747
Founders Village 2555 YOUNGS AVE 7D, SOUTHOLD, NY, 11971, Southold, NY 11971
$529,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

2555 YOUNGS AVE 7D, SOUTHOLD, NY, 11971
Community: Founders Village
New The Waterways at Moriches 497 OAK BLUFF CT, MORICHES, NY, 11955, Moriches, NY 11955
$559,999

2 beds

|

3 baths

|

1,988 sq ft

|

Condo

497 OAK BLUFF CT, MORICHES, NY, 11955
New Greenwood Village 5148 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$205,000

2 beds

|

2 baths

|

1,350 sq ft

|

Condo

5148 VILLAGE CIR, BROOKHAVEN, 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.
Dutchgate 1011 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580
$480,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1011 WILLOW LN, VALLEY STREAM, NY, 11580
Community: Dutchgate
Sunken Pond Estates 1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$469,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Meadowbrooke Pointe East Meadow 417 EMANUEL WAY # 417, EAST MEADOW, NY, ..., East Meadow, NY 11554
$725,000

2 beds

|

2 baths

|

961 sq ft

|

Condo

417 EMANUEL WAY # 417, EAST MEADOW, NY, ...
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
Glenwood Village 1661 OLD COUNTRY RD UNIT 521, RIVERHEAD,..., Riverhead, NY 11901
$369,000

2 beds

|

2 baths

|

Condo

1661 OLD COUNTRY RD UNIT 521, RIVERHEAD,...
Community: Glenwood Village
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
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
Jefferson Village 60 KIRBY CLOSE F, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598
$399,000

2 beds

|

2 baths

|

910 sq ft

|

Condo

60 KIRBY CLOSE F, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
New Leisure Village 231 BLACKPOOL CT, RIDGE, NY, 11961, Ridge, NY 11961
$289,000

2 beds

|

1 baths

|

825 sq ft

|

Condo

231 BLACKPOOL CT, RIDGE, NY, 11961
Community: Leisure Village
Leisure Knoll 209 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961
$430,000

2 beds

|

2 baths

|

1,116 sq ft

|

Condo

209 KINGSTON DR, RIDGE, NY, 11961
Community: Leisure Knoll
Greenwood Village 24 LIMETREE DR # 24, MANORVILLE, NY, 119..., Manorville, NY 11949
$224,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

24 LIMETREE DR # 24, MANORVILLE, NY, 119...
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.
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
Leisure Village 232 BLACKPOOL CT F, RIDGE, NY, 11961, Ridge, NY 11961
$279,900

2 beds

|

1 baths

|

833 sq ft

|

Condo

232 BLACKPOOL CT F, RIDGE, NY, 11961
Community: Leisure Village
The Bel Aire at East Meadow 50 MERRICK AVE 313, EAST MEADOW, NY, 115..., East Meadow, NY 11554
$439,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

50 MERRICK AVE 313, EAST MEADOW, NY, 115...
Vineyards at Blue Point 125 HALLEY DR, BLUE POINT, NY, 11772, Blue Point, NY 11772
$699,000

2 beds

|

2 baths

|

1,619 sq ft

|

Condo

125 HALLEY DR, BLUE POINT, NY, 11772
Leisure Village 28 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961
$379,999

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

28 TRENT CT B, RIDGE, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Jefferson Village 143 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$479,900

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

143 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Knickerbocker Bay Club 433 MAIN ST 203, PORT WASHINGTON, NY, 11..., Port Washington, NY 11050
$989,000

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

433 MAIN ST 203, PORT WASHINGTON, NY, 11...
Leisure Village 374 WOODBRIDGE DR UNIT A A, RIDGE, NY, 1..., Ridge, NY 11961
$329,999

2 beds

|

1 baths

|

1,187 sq ft

|

Condo

374 WOODBRIDGE DR UNIT A A, RIDGE, NY, 1...
Community: Leisure Village
Leisure Village 119 EXMORE CT A, RIDGE, NY, 11961, Ridge, NY 11961
$349,999

2 beds

|

1 baths

|

1,100 sq ft

|

Condo

119 EXMORE CT A, RIDGE, NY, 11961
Community: Leisure Village
Strathmore Gate East 9 FORGE LN, CORAM, NY, 11727, Coram, NY 11727
$339,999

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

9 FORGE LN, CORAM, NY, 11727
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.
Fairfield at St. James 1204 GOTHAM DR # 1204, SAINT JAMES, NY, ..., Saint James, NY 11780
$414,990

1 beds

|

2 baths

|

750 sq ft

|

Condo

1204 GOTHAM DR # 1204, SAINT JAMES, NY, ...
The Waterways at Moriches 276 DOCKSIDE CT, MORICHES, NY, 11955, Moriches, NY 11955
$699,000

2 beds

|

2 baths

|

1,875 sq ft

|

Condo

276 DOCKSIDE CT, MORICHES, NY, 11955
Heritage Hills 304 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$675,000

3 beds

|

3 baths

|

1,700 sq ft

|

Condo

304 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Foxwood Village 1407 MIDDLE RD 203, CALVERTON, NY, 11933, Calverton, NY 11933
$420,000

3 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

1407 MIDDLE RD 203, CALVERTON, NY, 11933
Community: Foxwood Village
Country Village Estates 192 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727
$475,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

192 THEODORE DR, CORAM, NY, 11727
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Heritage Hills 116 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$479,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

116 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Leisure Knoll 140A LAURANCE LN, RIDGE, NY, 11961, Ridge, NY 11961
$359,000

1 beds

|

1 baths

|

600 sq ft

|

Condo

140A LAURANCE LN, RIDGE, NY, 11961
Community: Leisure Knoll
Meadowbrook Pointe Athletic Club & Spa 100 SHADY LN # 100, WESTBURY, NY, 11590, Westbury, NY 11590
$889,000

2 beds

|

2 baths

|

1,353 sq ft

|

Condo

100 SHADY LN # 100, WESTBURY, NY, 11590
Plymouth Estates at Mount Sinai 211 POND CIR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$574,888

2 beds

|

2 baths

|

1,662 sq ft

|

Condo

211 POND CIR, MOUNT SINAI, NY, 11766
Leisure Village 312C WOODBRIDGE DR 312C, BROOKHAVEN, NY,..., Brookhaven, NY 11961
$277,000

1 beds

|

1 baths

|

679 sq ft

|

Condo

312C WOODBRIDGE DR 312C, BROOKHAVEN, NY,...
Community: Leisure Village

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287 homes near Middlebury
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