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

27 communities near Shirley

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3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
5 rating (1 review) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
5 rating (1 review) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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 review) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 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.
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 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
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 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
4 rating (1 review) Vineyards at Blue Point
$500ks - $700ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
1 rating (1 review) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 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.
5 rating (1 review) The Villages at Mount Sin...
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe Preserve, Yaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 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
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
Greenwood Village 5147 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$247,500

2 beds

|

2 baths

|

1,592 sq ft

|

Condo

5147 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 177 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$449,500

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

177 VENTRY CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
Greenwood Village 201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$250,000

2 beds

|

2 baths

|

1,078 sq ft

|

Condo

201 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Vineyards at Blue Point 103 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$699,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

103 HALLEY DR, BROOKHAVEN, NY, 11772
New Woodridge Strathmore Terrace 41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,000

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
New The Vineyards at Miller Place 48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$619,996

2 beds

|

3 baths

|

1,486 sq ft

|

Condo

48 AVERY LN, BROOKHAVEN, NY, 11764
New Leisure Glen 562 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$670,000

2 beds

|

2 baths

|

1,652 sq ft

|

House

562 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Leisure Glen 3 BALDWIN CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$519,900

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

3 BALDWIN CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Greenwood Village 24 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$79,999

1 beds

|

1 baths

|

812 sq ft

|

Condo

24 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Leisure Village 470B DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$339,000

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

470B DARWEN DR, BROOKHAVEN, 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.
New The Vineyards at Miller Place 40 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$625,000

3 beds

|

3 baths

|

1,700 sq ft

|

Condo

40 AVERY LN, BROOKHAVEN, NY, 11764
New Leisure Glen 488 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$659,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

488 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Stoneleigh Woods at Riverhead 904 BALTUSROL BLVD, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$510,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

904 BALTUSROL BLVD, RIVERHEAD, NY, 11901
The Vineyards at Miller Place 6 HALLEY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$559,000

2 beds

|

2 baths

|

1,291 sq ft

|

House

6 HALLEY LN, BROOKHAVEN, NY, 11764
Leisure Knoll 434 KINGSTON DR 434, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$499,000

2 beds

|

2 baths

|

1,646 sq ft

|

Condo

434 KINGSTON DR 434, BROOKHAVEN, NY, 119...
Community: Leisure Knoll
The Villages at Mount Sinai Park 93 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$799,000

2 beds

|

2 baths

|

2,234 sq ft

|

House

93 LOUDEN LOOP, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Leisure Glen 277 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$535,900

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

277 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Meadowbrook Pointe Links & Spa 146 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$800,000

2 beds

|

3 baths

|

2,047 sq ft

|

Condo

146 AUGUSTA DR, BROOKHAVEN, NY, 11763
Strathmore Gate East 46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$429,999

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

46 FORGE LN, BROOKHAVEN, NY, 11727
Greenwood Village 40 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,999

2 beds

|

1 baths

|

938 sq ft

|

Condo

40 GREENWOOD BLVD, 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.
Greenwood Village 5115 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$299,999

2 beds

|

2 baths

|

1,134 sq ft

|

House

5115 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11..., Brookhaven, NY 11961
$459,900

2 beds

|

2 baths

|

1,168 sq ft

|

Condo

379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11...
Community: Leisure Village
Leisure Glen 14 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$450,000

2 beds

|

2 baths

|

1,212 sq ft

|

House

14 FLANDERS CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Country Pointe Preserve 103 FOXWOOD DR 73, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$935,000

2 beds

|

3 baths

|

2,187 sq ft

|

Condo

103 FOXWOOD DR 73, BROOKHAVEN, NY, 11980
The Waterways at Moriches 129 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$749,000

2 beds

|

2 baths

|

1,762 sq ft

|

Condo

129 CAPTAINS CT, BROOKHAVEN, NY, 11955
Sunken Pond Estates 1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$545,000

2 beds

|

2 baths

|

1,258 sq ft

|

House

1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
The Waterways at Moriches 632 WATER WAY 32, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$699,000

2 beds

|

3 baths

|

1,874 sq ft

|

Condo

632 WATER WAY 32, BROOKHAVEN, NY, 11955
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Greenwood Village 205 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$169,999

2 beds

|

2 baths

|

1,138 sq ft

|

House

205 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 222 BLACKPOOL CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$319,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

222 BLACKPOOL CT A, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Leisure Village 387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$449,000

2 beds

|

2 baths

|

1,767 sq ft

|

Condo

387 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.
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$397,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Knoll 346 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$419,000

2 beds

|

1 baths

|

1,050 sq ft

|

Condo

346 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Sunken Pond Estates 3102 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$519,900

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3102 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Leisure Knoll 177 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$379,900

2 beds

|

1 baths

|

1,116 sq ft

|

Condo

177 CANTERBURY DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Foxwood Village 1407 MIDDLE RD 271, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$465,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933
Community: Foxwood Village
Greenwood Village 33 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$225,000

2 beds

|

2 baths

|

1,134 sq ft

|

House

33 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Windcrest East 90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$799,000

3 beds

|

3 baths

|

2,620 sq ft

|

Condo

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
Windcrest East 29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$785,000

3 beds

|

3 baths

|

2,531 sq ft

|

Condo

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
Want to learn more about 55+ communities in Shirley? 55places can help!
Questions? Call us: (934) 333-5665
Greenwood Village 10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$179,999

2 beds

|

1 baths

|

938 sq ft

|

Condo

10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 1 LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$248,833

2 beds

|

2 baths

|

1,027 sq ft

|

Condo

1 LIMETREE DR, 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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