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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
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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
The Villages at Mount Sinai Park 4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$849,999

3 beds

|

3 baths

|

2,850 sq ft

|

Condo

4 OAKHURST CT, MOUNT SINAI, NY, 11766
Heritage Hills 348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$615,000

2 beds

|

2 baths

|

1,428 sq ft

|

Condo

348 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Greenwood Village 71 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949
$238,000

2 beds

|

2 baths

|

1,123 sq ft

|

Condo

71 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
Leisure Glen 437 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961
$525,000

2 beds

|

2 baths

|

1,417 sq ft

|

Condo

437 LEISURE DR, RIDGE, NY, 11961
Community: Leisure Glen
Glenwood Village 1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$245,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...
Community: Glenwood Village
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
New Heritage Hills 963 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$650,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

963 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Meadowbrooke Pointe East Meadow 506 EMANUEL WAY # 73, EAST MEADOW, NY, 1..., East Meadow, NY 11554
$720,000

1 beds

|

2 baths

|

961 sq ft

|

Condo

506 EMANUEL WAY # 73, EAST MEADOW, NY, 1...
Meadowbrooke Pointe East Meadow 514 EMANUEL WAY # 77, EAST MEADOW, NY, 1..., East Meadow, NY 11554
$790,000

1 beds

|

3 baths

|

2,061 sq ft

|

Condo

514 EMANUEL WAY # 77, EAST MEADOW, NY, 1...
Jefferson Village 40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$599,900

2 beds

|

2 baths

|

1,350 sq ft

|

Condo

40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Country Village Estates 11 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727
$479,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

11 THEODORE DR, 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.
The Waterways at Moriches 381 QUARRY POND CT, MORICHES, NY, 11955, Moriches, NY 11955
$649,000

2 beds

|

2 baths

|

2,200 sq ft

|

Condo

381 QUARRY POND CT, MORICHES, NY, 11955
The Waterways at Moriches 295 W MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955
$699,990

2 beds

|

2 baths

|

2,149 sq ft

|

Condo

295 W MIDLAND POND CT, MORICHES, NY, 119...
New Sunken Pond Estates 3804 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$519,000

2 beds

|

3 baths

|

1,674 sq ft

|

Condo

3804 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Meadowbrook Pointe Links & Spa 234 AUGUSTA DR # 234, MEDFORD, NY, 11763, Medford, NY 11763
$745,000

2 beds

|

3 baths

|

1,627 sq ft

|

Condo

234 AUGUSTA DR # 234, MEDFORD, NY, 11763
Country Pointe Plainview 34203 WINTERBERRY DR, PLAINVIEW, NY, 118..., Plainview, NY 11803
$899,888

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

34203 WINTERBERRY DR, PLAINVIEW, NY, 118...
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
New Dutchgate 1512 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580
$475,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1512 WILLOW LN, VALLEY STREAM, NY, 11580
Community: Dutchgate
Leisure Village 232A BLACKPOOL CT 232A, BROOKHAVEN, NY, ..., Brookhaven, NY 11961
$305,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

232A BLACKPOOL CT 232A, BROOKHAVEN, NY, ...
Community: Leisure Village
The Waterways at Moriches 106 E MIDLAND POND CT # 1, MORICHES, NY,..., Moriches, NY 11955
$499,000

2 beds

|

2 baths

|

1,982 sq ft

|

Condo

106 E MIDLAND POND CT # 1, MORICHES, NY,...
Leisure Village 286 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961
$359,900

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

286 BERWICK CT A, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 305 TORQUAY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961
$364,500

2 beds

|

1 baths

|

836 sq ft

|

House

305 TORQUAY CT UNIT C, RIDGE, NY, 11961
Community: Leisure 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.
The Seasons at Plainview 75 AUTUMN DR, PLAINVIEW, NY, 11803, Plainview, NY 11803
$699,999

2 beds

|

2 baths

|

1,379 sq ft

|

Condo

75 AUTUMN DR, PLAINVIEW, NY, 11803
New Saddle Lakes 107 SCENIC LAKE DR # 107, RIVERHEAD, NY,..., Riverhead, NY 11901
$639,000

2 beds

|

2 baths

|

1,631 sq ft

|

Condo

107 SCENIC LAKE DR # 107, RIVERHEAD, NY,...
Community: Saddle Lakes
Fairfield at St. James 206 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$570,000

3 beds

|

3 baths

|

1,649 sq ft

|

Condo

206 FLAIR CT, SMITHTOWN, NY, 11780
Greenwood Village 87 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$179,000

2 beds

|

1 baths

|

992 sq ft

|

Condo

87 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
The Polo Club at Islandia 1239 OLD NICHOLS RD # 46, ISLANDIA, NY, ..., Islandia, NY 11749
$639,000

2 beds

|

3 baths

|

1,654 sq ft

|

Condo

1239 OLD NICHOLS RD # 46, ISLANDIA, NY, ...
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Country Pointe Plainview 17101 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803
$1,055,000

2 beds

|

2 baths

|

1,443 sq ft

|

Condo

17101 ASPENWOOD DR, PLAINVIEW, NY, 11803
New Leisure Knoll 145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961
$418,000

2 beds

|

2 baths

|

900 sq ft

|

Condo

145 EDINBURGH DR, RIDGE, NY, 11961
Community: Leisure Knoll
Glenwood Village 1661 OLD COUNTRY RD UNIT 200, RIVERHEAD,..., Riverhead, NY 11901
$249,900

2 beds

|

1 baths

|

753 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 200, RIVERHEAD,...
Community: Glenwood Village
Vineyards at Blue Point 26 AVERY WAY # 26, BLUE POINT, NY, 11772, Blue Point, NY 11772
$925,000

2 beds

|

4 baths

|

3,388 sq ft

|

Condo

26 AVERY WAY # 26, BLUE POINT, NY, 11772
New Leisure Village 68A ENFIELD CT # 68A, RIDGE, NY, 11961, Ridge, NY 11961
$369,000

2 beds

|

1 baths

|

1,048 sq ft

|

Condo

68A ENFIELD CT # 68A, RIDGE, NY, 11961
Community: Leisure 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.
Vineyards at Moriches 52 TONI CT # 52, CENTER MORICHES, NY, 11..., Center Moriches, NY 11934
$699,000

2 beds

|

3 baths

|

2,196 sq ft

|

Condo

52 TONI CT # 52, CENTER MORICHES, NY, 11...
Encore at Lake Grove 20 CONCERTO DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755
$699,990

2 beds

|

3 baths

|

1,413 sq ft

|

Condo

20 CONCERTO DR, LAKE GROVE, NY, 11755
New Meadowbrook Pointe Athletic Club & Spa 494 PACING WAY # 301C, WESTBURY, NY, 115..., Westbury, NY 11590
$850,000

2 beds

|

2 baths

|

1,353 sq ft

|

Condo

494 PACING WAY # 301C, WESTBURY, NY, 115...
Stoneleigh Woods at Riverhead 8 LAKEVIEW CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$615,000

3 beds

|

3 baths

|

2,000 sq ft

|

Condo

8 LAKEVIEW CT, RIVERHEAD, NY, 11901
Vineyards at Moriches 30 TONI CT # 30, CENTER MORICHES, NY, 11..., Center Moriches, NY 11934
$725,000

2 beds

|

3 baths

|

2,204 sq ft

|

Condo

30 TONI CT # 30, CENTER MORICHES, NY, 11...
Want to learn more about 55+ communities in Middlebury? 55places can help!
Questions? Call us: (959) 214-4386
Encore at Lake Grove 3 CONCERTO DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755
$820,000

2 beds

|

3 baths

|

1,835 sq ft

|

Condo

3 CONCERTO DR, LAKE GROVE, NY, 11755
HarborView 161 HARBOR VIEW DR, PORT WASHINGTON, NY,..., Port Washington, NY 11050
$1,600,000

4 beds

|

4 baths

|

3,452 sq ft

|

Condo

161 HARBOR VIEW DR, PORT WASHINGTON, NY,...
Community: HarborView
Greenwood Village 10 ORANGE TREE CT, MANORVILLE, NY, 11949, Manorville, NY 11949
$210,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

10 ORANGE TREE CT, MANORVILLE, NY, 11949
Community: Greenwood Village
Greenwood Village 132 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$214,990

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

132 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Meadowbrook Pointe Links & Spa 142 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763
$729,990

2 beds

|

3 baths

|

1,691 sq ft

|

Condo

142 AUGUSTA DR, MEDFORD, NY, 11763

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287 homes near Middlebury
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