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

139 communities near Milford

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Baldwin Station
$400Ks - $400Ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Gloria Commons
$400Ks - $400Ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
3 rating (2 reviews) Heritage Hills
$300Ks - $900Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.6 rating (7 reviews) Heritage Village
$100Ks - $500Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
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 Milford? 55places can help!
Questions? Call us: (475) 271-1803
The Greens at Half Hollow
$500Ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes
Rivington
$600Ks - $600Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
Oronoque Village
$200Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
The Village at Oxford Gre...
$500Ks - $700Ks
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.
Meadowbrook Pointe Athlet...
$800Ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Leisure Knoll
$300Ks - $400Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Country Pointe Plainview
$1Ms - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (2 reviews) Fairfield at St. James
$400Ks - $400Ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
Leisure Glen
$400Ks - $400Ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Want to learn more about 55+ communities in Milford? 55places can help!
Questions? Call us: (475) 271-1803
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 - $400Ks
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
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
Regency at Prospect
$300Ks - $500Ks
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.
Dutchgate
$400Ks - $400Ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
The Waterways at Moriches
$400Ks - $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
The Retreat at Carmel
$400Ks - $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Overlook
$600Ks - $900Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
3.5 rating (2 reviews) Foxwood Village
$300Ks - $400Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Want to learn more about 55+ communities in Milford? 55places can help!
Questions? Call us: (475) 271-1803
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
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$300Ks - $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
4 rating (1 reviews) Vineyards at Blue Point
$800Ks - $800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
HarborView
$900Ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
The Club at Melville
$500Ks - $500Ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 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 Elwood
$800Ks - $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
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
The Summit at Bethel
$600Ks - $600Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks - $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
Want to learn more about 55+ communities in Milford? 55places can help!
Questions? Call us: (475) 271-1803
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
Woodridge Strathmore Terr...
$400Ks - $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Regency at Wappinger
$600Ks - $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
5 rating (1 reviews) Sunrise Village
$400Ks - $500Ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Saddle Lakes
$400Ks - $400Ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Stoneleigh Woods at Riverhead 4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$660,000

2 beds

|

3 baths

|

2,175 sq ft

|

Condo

4 HAVERTON CT, RIVERHEAD, NY, 11901
Leisure Glen 12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961
$489,990

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

12 BALDWIN CT, RIDGE, NY, 11961
Community: Leisure Glen
Leisure Glen 12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961
$489,990

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

12 BALDWIN CT, RIDGE, NY, 11961
Community: Leisure Glen
Glenwood Village 1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE..., Riverhead, NY 11901
$285,000

2 beds

|

2 baths

|

1,232 sq ft

|

Manufactured Home

1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE...
Community: Glenwood Village
Glenwood Village 1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE..., Riverhead, NY 11901
$285,000

2 beds

|

2 baths

|

1,232 sq ft

|

Manufactured Home

1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE...
Community: Glenwood Village
Want to learn more about 55+ communities in Milford? 55places can help!
Questions? Call us: (475) 271-1803
Leisure Village 259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961
$254,900

1 beds

|

1 baths

|

875 sq ft

|

Condo

259 NEWCASTLE CT E, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961
$254,900

1 beds

|

1 baths

|

875 sq ft

|

Condo

259 NEWCASTLE CT E, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 96 ENFIELD CT B, RIDGE, NY, 11961, Ridge, NY 11961
$424,000

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

96 ENFIELD CT B, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119..., Ridge, NY 11961
$260,000

1 beds

|

1 baths

|

782 sq ft

|

Condo

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119...
Community: Leisure Village
Leisure Village 419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119..., Ridge, NY 11961
$260,000

1 beds

|

1 baths

|

782 sq ft

|

Condo

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119...
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.
Leisure Village 166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961
$259,000

1 beds

|

1 baths

|

680 sq ft

|

House

166 VENTRY CT B, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961
$259,000

1 beds

|

1 baths

|

680 sq ft

|

House

166 VENTRY CT B, RIDGE, NY, 11961
Community: Leisure Village
New Breton Hills 209 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$699,888

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

209 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton Hills
Leisure Glen 256 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961
$499,000

2 beds

|

2 baths

|

1,456 sq ft

|

Condo

256 GLEN DR, RIDGE, NY, 11961
Community: Leisure Glen
New Heritage Hills 349 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

2 baths

|

1,484 sq ft

|

Condo

349 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Milford? 55places can help!
Questions? Call us: (475) 271-1803
New Heritage Hills 299 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$693,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

299 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Breton Hills 512 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$639,000

2 beds

|

2 baths

|

1,430 sq ft

|

Condo

512 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton Hills
Heritage Hills 688 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$725,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

688 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Greenwood Village 53 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$275,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

53 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Jefferson Village 170 LONG HILL DR A, YORKTOWN HEIGHTS, NY..., Yorktown Heights, NY 10598
$675,000

2 beds

|

2 baths

|

1,555 sq ft

|

Condo

170 LONG HILL DR A, YORKTOWN HEIGHTS, NY...
Community: Jefferson 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.
Leisure Village 310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961
$342,000

2 beds

|

1 baths

|

1,278 sq ft

|

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...
Community: Leisure Village
New Jefferson Village 159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$569,999

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
New Plymouth Estates at Mount Sinai 230 IRA RD # 230, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$589,999

2 beds

|

2 baths

|

1,317 sq ft

|

Condo

230 IRA RD # 230, MOUNT SINAI, NY, 11766
New The Waterways at Moriches 416 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955
$575,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

416 LINDSAY LN, MORICHES, NY, 11955
New Glenwood Village 1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,..., Riverhead, NY 11901
$205,000

2 beds

|

2 baths

|

1,008 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,...
Community: Glenwood Village
Want to learn more about 55+ communities in Milford? 55places can help!
Questions? Call us: (475) 271-1803
Heritage Hills 798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$619,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Regency at Fishkill 736 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$499,000

1 beds

|

2 baths

|

1,543 sq ft

|

House

736 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Glassbury Court at Cold Spring 43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516
$729,000

2 beds

|

3 baths

|

2,620 sq ft

|

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516
Greenwood Village 145 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$199,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

145 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
New Glassbury Court at Cold Spring 11 REVOLUTION RD, COLD SPRING, NY, 10516, Cold Spring, NY 10516
$515,000

2 beds

|

3 baths

|

1,806 sq ft

|

Condo

11 REVOLUTION RD, COLD SPRING, NY, 10516
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 Setauket Meadows 95 COVE LN, EAST SETAUKET, NY, 11733, East Setauket, NY 11733
$749,990

2 beds

|

3 baths

|

1,991 sq ft

|

Condo

95 COVE LN, EAST SETAUKET, NY, 11733
Community: Setauket Meadows
Heritage Hills 593 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$619,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

593 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 262 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$550,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

262 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 262 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$550,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

262 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 882 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$825,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

882 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Milford? 55places can help!
Questions? Call us: (475) 271-1803
Heritage Hills 882 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$825,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

882 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Greenwood Village 99 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$269,988

2 beds

|

2 baths

|

1,487 sq ft

|

Condo

99 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Greenwood Village 99 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$269,988

2 beds

|

2 baths

|

1,487 sq ft

|

Condo

99 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
The Hollows at Blue Hill 41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ..., Pearl River, NY 10965
$999,000

2 beds

|

3 baths

|

2,210 sq ft

|

Condo

41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ...
The Hollows at Blue Hill 41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ..., Pearl River, NY 10965
$999,000

2 beds

|

3 baths

|

2,210 sq ft

|

Condo

41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ...

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139 communities near Milford
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