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Call us at (934) 333-5665 to learn more about active adult communities in Shirley

Shirley, NY 55+ active adult communities & homes for sale

27 communities near Shirley

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Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 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
5 rating (1 reviews) The Villages at Mount Sin...
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 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
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
The Vineyards at Miller P...
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 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
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 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.
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 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
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
$500ks - $700ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
New Meadowbrook Pointe Links & Spa 48 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$749,990

2 beds

|

4 baths

|

1,553 sq ft

|

Condo

48 AUGUSTA DR, BROOKHAVEN, NY, 11763
New Leisure Glen 289 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$585,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

289 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Leisure Village 323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$475,000

2 beds

|

2 baths

|

1,278 sq ft

|

Condo

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119...
Community: Leisure Village
New Country Pointe Preserve 3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$965,000

2 beds

|

3 baths

|

2,389 sq ft

|

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980
Stoneleigh Woods at Riverhead 156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$659,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Leisure Glen 155 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$495,000

2 beds

|

2 baths

|

1,456 sq ft

|

Condo

155 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Encore Atlantic Shores 11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$925,000

2 beds

|

3 baths

|

3,037 sq ft

|

House

11 OVATION PL, BROOKHAVEN, NY, 11941
The Waterways at Moriches 248 RIVER DR 248, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$629,000

2 beds

|

2 baths

|

1,544 sq ft

|

Condo

248 RIVER DR 248, BROOKHAVEN, NY, 11955
Leisure Village 150 EASTBOURNE CT B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$419,000

2 beds

|

2 baths

|

1,515 sq ft

|

Condo

150 EASTBOURNE CT B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Foxwood Village 1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$469,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, 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.
Leisure Glen 82 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,000

2 beds

|

2 baths

|

1,312 sq ft

|

Condo

82 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Leisure Knoll 259 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$445,000

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

259 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Strathmore Gate East 55 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$420,000

2 beds

|

1 baths

|

964 sq ft

|

Condo

55 FORGE LN, BROOKHAVEN, NY, 11727
Leisure Glen 12 BALDWIN CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,990

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

12 BALDWIN CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
The Villages at Mount Sinai Park 16 OAKHURST CT, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$789,000

2 beds

|

2 baths

|

1,929 sq ft

|

House

16 OAKHURST CT, BROOKHAVEN, NY, 11766
The Waterways at Moriches 485 WOODSCREEK CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$778,000

2 beds

|

3 baths

|

1,854 sq ft

|

Condo

485 WOODSCREEK CT, BROOKHAVEN, NY, 11955
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Leisure Village 404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

907 sq ft

|

Condo

404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$421,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
Glenwood Village 1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ..., Riverhead, NY 11901
$339,000

2 beds

|

2 baths

|

1,344 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Village 368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$419,990

2 beds

|

1 baths

|

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, 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 Knoll 204 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$449,000

2 beds

|

2 baths

|

849 sq ft

|

House

204 BELFAST LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Leisure Village 124 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$354,900

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

124 EXMORE CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Manors at The Colony Preserve 15 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$499,999

2 beds

|

2 baths

|

1,322 sq ft

|

Condo

15 CRICKET CT, BROOKHAVEN, NY, 11967
Woodridge Strathmore Terrace 7 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$449,000

2 beds

|

2 baths

|

840 sq ft

|

Condo

7 COBBLESTONE WAY, BROOKHAVEN, NY, 11766
Greenwood Village 191 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,999

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

191 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
The Waterways at Moriches 549 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$649,000

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

549 HIGHLAND CT, BROOKHAVEN, NY, 11955
Leisure Village 248 NEWCASTLE CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$415,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

248 NEWCASTLE CT A, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Leisure Village 375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$389,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119...
Community: Leisure Village
The Manors at The Colony Preserve 94 LAKESIDE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$529,999

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

94 LAKESIDE CT, BROOKHAVEN, NY, 11967
Strathmore Gate East 22 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$429,000

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

22 FREEMONT LN, BROOKHAVEN, 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.
Glenwood Village 1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$425,000

3 beds

|

2 baths

|

1,680 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1...
Community: Glenwood Village
Leisure Village 72 ENFIELD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

72 ENFIELD CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
Country Pointe Preserve 118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$865,000

2 beds

|

3 baths

|

1,998 sq ft

|

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980
The Waterways at Moriches 290 W MIDLAND POND CT 290, BROOKHAVEN, N..., Brookhaven, NY 11955
$629,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

290 W MIDLAND POND CT 290, BROOKHAVEN, N...
Leisure Village 279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$289,999

2 beds

|

1 baths

|

875 sq ft

|

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Waterways at Moriches 188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$775,000

2 beds

|

2 baths

|

2,100 sq ft

|

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955
Glenwood Village 1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ..., Riverhead, NY 11901
$130,000

2 beds

|

1 baths

|

720 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ...
Community: Glenwood Village
Sunken Pond Estates 3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$499,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Greenwood Village 2 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$192,500

2 beds

|

2 baths

|

1,064 sq ft

|

Condo

2 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 43 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$235,000

2 beds

|

2 baths

|

1,164 sq ft

|

Condo

43 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.

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This application does not include information on all of the properties available for sale at this time.

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