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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
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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
5 rating (1 reviews) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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.
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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
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
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
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
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 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.
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
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
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
New Sunken Pond Estates 2201 PEBBLE BEACH PATH 2201, RIVERHEAD, ..., Riverhead, NY 11901
$549,900

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

2201 PEBBLE BEACH PATH 2201, RIVERHEAD, ...
Community: Sunken Pond Estates
New Encore Atlantic Shores 177 MELODY CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$765,000

2 beds

|

2 baths

|

2,150 sq ft

|

Condo

177 MELODY CT, BROOKHAVEN, NY, 11941
New The Waterways at Moriches 376 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$519,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

376 QUARRY POND CT, BROOKHAVEN, NY, 1195...
New The Waterways at Moriches 519 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$610,000

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

519 HIGHLAND CT, BROOKHAVEN, NY, 11955
New The Vineyards at Mount Sinai 51 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$1,085,000

2 beds

|

3 baths

|

3,214 sq ft

|

Condo

51 FARM ACRE CIR, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
New Leisure Village 368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$379,990

2 beds

|

1 baths

|

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...
Community: Leisure Village
Leisure Village 196 NEWCASTLE CT C, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$330,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

196 NEWCASTLE CT C, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Greenwood Village 11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11..., Brookhaven, NY 11949
$199,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11...
Community: Greenwood Village
The Manors at The Colony Preserve 40 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$540,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

40 GREENTREE CT, BROOKHAVEN, NY, 11967
The Waterways at Moriches 188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$729,000

2 beds

|

2 baths

|

2,100 sq ft

|

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955
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 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Knoll 379 LARCHMONT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$539,000

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

379 LARCHMONT CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Leisure Knoll 220 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$539,999

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

220 BELFAST LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Leisure Glen 515 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$560,000

2 beds

|

2 baths

|

1,434 sq ft

|

House

515 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Greenwood Village 40 WILLOW CT, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$249,999

2 beds

|

2 baths

|

1,151 sq ft

|

Manufactured On Land

40 WILLOW CT, BROOKHAVEN, NY, 11949
Community: Greenwood Village
The Waterways at Moriches 377 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$599,999

3 beds

|

2 baths

|

2,141 sq ft

|

Condo

377 QUARRY POND CT, BROOKHAVEN, NY, 1195...
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Woodridge Strathmore Terrace 58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$435,000

2 beds

|

2 baths

|

1,025 sq ft

|

Condo

58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Greenwood Village 131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$165,000

2 beds

|

2 baths

|

1,062 sq ft

|

Manufactured Home

131 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
The Waterways at Moriches 629 WATER WAY 29, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$715,000

2 beds

|

3 baths

|

1,611 sq ft

|

Condo

629 WATER WAY 29, BROOKHAVEN, NY, 11955
Foxwood Village 1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933, Brookhaven, NY 11933
$425,000

2 beds

|

2 baths

|

1,444 sq ft

|

Manufactured Home

1407 MIDDLE RD 83, BROOKHAVEN, 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 Knoll 491 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$489,000

2 beds

|

2 baths

|

976 sq ft

|

Condo

491 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Plymouth Estates at Mount Sinai 26 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$595,000

2 beds

|

2 baths

|

1,563 sq ft

|

Condo

26 ROSE LN, BROOKHAVEN, NY, 11766
The Villages at Mount Sinai Park 10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$749,000

3 beds

|

3 baths

|

2,500 sq ft

|

House

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766
The Villages at Mount Sinai Park 54 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$899,000

3 beds

|

3 baths

|

2,816 sq ft

|

House

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766
The Villages at Mount Sinai Park 68 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$839,999

2 beds

|

2 baths

|

1,736 sq ft

|

House

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766
Leisure Knoll 257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$399,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Stoneleigh Woods at Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$699,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Westhampton Pines 49 SAMANTHA CIR 49, SOUTHAMPTON, NY, 119..., Southampton, NY 11977
$989,000

2 beds

|

2 baths

|

1,944 sq ft

|

Condo

49 SAMANTHA CIR 49, SOUTHAMPTON, NY, 119...
Community: Westhampton Pines
Leisure Village 395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...
Community: Leisure Village
The Manors at The Colony Preserve 17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$559,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967
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 541 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$519,000

3 beds

|

2 baths

|

1,412 sq ft

|

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Foxwood Village 1407 MIDDLE RD 253, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$449,000

3 beds

|

2 baths

|

1,753 sq ft

|

House

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933
Community: Foxwood Village
Leisure Village 265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$335,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Leisure Knoll 520 CRANSTON LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$499,999

2 beds

|

2 baths

|

1,574 sq ft

|

Condo

520 CRANSTON LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
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
Leisure Village 323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$425,000

2 beds

|

2 baths

|

1,278 sq ft

|

Condo

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119...
Community: Leisure Village
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
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
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.

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