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New Windsor, MD 55+ active adult communities & homes for sale

544 homes near New Windsor

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The Reserve at New Windso...
$400Ks - $400Ks
The Reserve at New Windso..., New Windsor, MD
Resale Only | 55+ age-restricted | Built 2016 - 2021 | 83 homes
5 rating (1 reviews) Leisure World® of Marylan...
<$100k - $500Ks
Leisure World® of Marylan..., Silver Spring, MD
Resale Only | 55+ age-restricted | Built 1966 - 2009 | 5,600 homes
4.3 rating (11 reviews) Amblebrook
$300Ks - $1Ms
Amblebrook, Gettysburg, PA
New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes
5 rating (3 reviews) Heritage Hunt
$400Ks - $800Ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
3.7 rating (3 reviews) Heritage Harbour
$300Ks - $500Ks
Heritage Harbour, Annapolis, MD
Resale Only | 55+ age-restricted | Built 1979 - 2008 | 1,683 homes
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2 rating (1 reviews) Birchwood at Brambleton
$400Ks - $1Ms
Birchwood at Brambleton, Ashburn, VA
New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes
5 rating (2 reviews) Potomac Green
$800Ks - $900Ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
5 rating (31 reviews) Lansdowne Woods of Virgin...
$200Ks - $500Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes
Penn National
$200Ks - $500Ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
Four Seasons at Kent Isla...
$400Ks - $1Ms
Four Seasons at Kent Isla..., Kent Island, MD
New Construction | 55+ age-restricted | Built 2018 - present | 1,079 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 reviews) Regency at Dominion Valle...
$400Ks - $800Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
5 rating (1 reviews) Two Rivers
$500Ks - $800Ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
Cameron Grove
$200Ks - $400Ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 homes
5 rating (2 reviews) Central Parke at Victoria...
$300Ks - $600Ks
Central Parke at Victoria..., Laurel, MD
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes
The Woodlands of Urbana
$600Ks - $600Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
5 rating (1 reviews) Crestwood Village
$300Ks - $300Ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
Traditions of America at ...
$400Ks - $500Ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 homes
Alden Place
$300Ks - $600Ks
Alden Place, Lebanon, PA
New and Resale | 55+ age-restricted | Built 2009 - present | 505 homes
Carter's Mill
$400Ks - $700Ks
Carter's Mill, Haymarket, VA
New Construction | 55+ age-restricted | Built 2020 - present | 480 homes
3 rating (2 reviews) Dunbarton
$600Ks - $600Ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 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 Courtyards at Waverly...
$300Ks - $900Ks
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 homes
5 rating (1 reviews) Carroll Vista
$300Ks - $500Ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 homes
Cedar Ridge at Piney Orch...
$300Ks - $400Ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
Montebello
$600Ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
Village Crest
$300Ks - $400Ks
Village Crest, Ellicott City, MD
New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Courtyards at Waverly Woo...
$300Ks - $400Ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 383 homes
5 rating (2 reviews) Arbor Gate
$200Ks - $300Ks
Arbor Gate, Myerstown, PA
Resale Only | 55+ age-restricted | Built 1997 - 2005 | 378 homes
5 rating (1 reviews) Snowden Overlook
$400Ks - $700Ks
Snowden Overlook, Columbia, MD
Resale Only | 55+ age-restricted | Built 2005 - 2010 | 350 homes
4 rating (2 reviews) Traditions of America at ...
$500Ks - $600Ks
Traditions of America at ..., Lititz, PA
Resale Only | 55+ age-restricted | Built 2013 - 2021 | 329 homes
Creek View
$100Ks - $200Ks
Creek View, Carlisle, PA
New and Resale | 55+ age-restricted | Built 2004 - present | 305 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.
Longstown Village
$100Ks - $200Ks
Longstown Village, York, PA
Resale Only | Age-targeted | Built 1997 - 2000 | 304 homes
The Villages At Woodholme
$400Ks - $500Ks
The Villages At Woodholme, Baltimore, MD
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 286 homes
Spring Hill
$500Ks - $800Ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
The Enclave at Ellicott H...
$300Ks - $400Ks
The Enclave at Ellicott H..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 280 homes
Bay Bridge Cove
$600Ks - $600Ks
Bay Bridge Cove, Stevensville, MD
Resale Only | 55+ age-restricted | Built 2016 - 2022 | 273 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Regency at Ashburn
$800Ks - $900Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
The Crest of Alexandria
$900Ks - $900Ks
The Crest of Alexandria, Alexandria, VA
New and Resale | 55+ age-restricted | Built 2017 - present | 250 homes
Emerald Pointe
$300Ks - $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Traditions of America at ...
$500Ks - $700Ks
Traditions of America at ..., East Petersburg, PA
New Construction | 55+ age-restricted | Built 2021 - present | 247 homes
5 rating (2 reviews) Four Seasons at Elm Tree
$200Ks - $400Ks
Four Seasons at Elm Tree, Mount Joy, PA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 245 homes
Two Rivers 3148 SUNNY RIDGE DR, ODENTON, MD, 21113, Odenton, MD 21113
$739,900

3 beds

|

3 baths

|

2,056 sq ft

3148 SUNNY RIDGE DR, ODENTON, MD, 21113
Community: Two Rivers
Leisure World® of Maryland 15301 PINE ORCHARD DR 86-3E, SILVER SPRI..., Silver Spring, MD 20906
$289,999

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15301 PINE ORCHARD DR 86-3E, SILVER SPRI...
Four Seasons at Kent Island 132 WHEELHOUSE WAY, CHESTER, MD, 21619, Chester, MD 21619
$1,350,000

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

132 WHEELHOUSE WAY, CHESTER, MD, 21619
Leisure World® of Maryland 15030 WESTHOLM CT # 268-C, SILVER SPRING..., Silver Spring, MD 20906
$299,000

3 beds

|

2 baths

|

1,194 sq ft

|

Condo

15030 WESTHOLM CT # 268-C, SILVER SPRING...
Emerald Pointe 13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742
$429,000

2 beds

|

3 baths

|

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...
Community: Emerald Pointe
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Colonial Charles 3141 LADY BANKS LN, WALDORF, MD, 20603, Waldorf, MD 20603
$450,000

3 beds

|

3 baths

|

2,400 sq ft

3141 LADY BANKS LN, WALDORF, MD, 20603
Community: Colonial Charles
Four Seasons at Kent Island 135 NAUSET LN, CHESTER, MD, 21619, Chester, MD 21619
$814,900

3 beds

|

3 baths

|

2,399 sq ft

135 NAUSET LN, CHESTER, MD, 21619
Gatherings at Lyndwood 7315 BROOKVIEW RD 302, ELKRIDGE, MD, 210..., Elkridge, MD 21075
$465,000

2 beds

|

2 baths

|

1,900 sq ft

|

Condo

7315 BROOKVIEW RD 302, ELKRIDGE, MD, 210...
Carroll Vista 101 BUTTERFLY DR # 106, TANEYTOWN, MD, 2..., Taneytown, MD 21787
$382,900

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

101 BUTTERFLY DR # 106, TANEYTOWN, MD, 2...
Community: Carroll Vista
Heritage Harbour 930 ASTERN WAY 502, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$350,000

2 beds

|

2 baths

|

1,477 sq ft

|

Condo

930 ASTERN WAY 502, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
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.
Central Parke at Victoria Falls 13851 BELLE CHASSE BLVD UNIT 213, LAUREL..., Laurel, MD 20707
$410,000

2 beds

|

2 baths

|

1,703 sq ft

|

Condo

13851 BELLE CHASSE BLVD UNIT 213, LAUREL...
Signature Club at Greenview 5816 DREXAL AVE, NEW MARKET, MD, 21774, New Market, MD 21774
$950,000

5 beds

|

4 baths

|

4,926 sq ft

5816 DREXAL AVE, NEW MARKET, MD, 21774
Four Seasons at Kent Island 154 HARRIER WAY, CHESTER, MD, 21619, Chester, MD 21619
$639,545

2 beds

|

2 baths

|

1,900 sq ft

154 HARRIER WAY, CHESTER, MD, 21619
McKinsey Park 600 MCKINSEY PARK DR APT 102, SEVERNA PA..., Severna Park, MD 21146
$400,000

2 beds

|

2 baths

|

1,226 sq ft

600 MCKINSEY PARK DR APT 102, SEVERNA PA...
Community: McKinsey Park
Heritage Harbour 940 ASTERN WAY UNIT 604, ANNAPOLIS, MD, ..., Annapolis, MD 21401
$415,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

940 ASTERN WAY UNIT 604, ANNAPOLIS, MD, ...
Community: Heritage Harbour
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 15015 HASLEMERE CT, SILVER SPRING, MD, 2..., Silver Spring, MD 20906
$380,000

3 beds

|

2 baths

|

1,194 sq ft

|

Condo

15015 HASLEMERE CT, SILVER SPRING, MD, 2...
Four Seasons at Kent Island 170 HARRIER WAY UNIT 22, CHESTER, MD, 21..., Chester, MD 21619
$510,000

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

170 HARRIER WAY UNIT 22, CHESTER, MD, 21...
Ellicott's Retreat 8580 SUNELL LN, ELLICOTT CITY, MD, 21043, Ellicott City, MD 21043
$1,299,000

6 beds

|

7 baths

|

4,241 sq ft

8580 SUNELL LN, ELLICOTT CITY, MD, 21043
Community: Ellicott's Retreat
Four Seasons at Saint Margaret's 1509 FERAL DAE LN UNIT 204, ANNAPOLIS, M..., Annapolis, MD 21409
$489,000

2 beds

|

2 baths

|

1,442 sq ft

|

Condo

1509 FERAL DAE LN UNIT 204, ANNAPOLIS, M...
Nells Acres 1909 LENNOX DR 90, ELDERSBURG, MD, 21784, Eldersburg, MD 21784
$339,900

3 beds

|

3 baths

|

1,620 sq ft

|

Condo

1909 LENNOX DR 90, ELDERSBURG, MD, 21784
Community: Nells Acres
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.
Four Seasons at Kent Island 170 HARRIER WAY 11, CHESTER, MD, 21619, Chester, MD 21619
$499,000

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

170 HARRIER WAY 11, CHESTER, MD, 21619
Gatherings at Lyndwood 7315 MAPLECREST RD 405, ELKRIDGE, MD, 21..., Elkridge, MD 21075
$419,900

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

7315 MAPLECREST RD 405, ELKRIDGE, MD, 21...
Leisure World® of Maryland 3330 N LEISURE WORLD BLVD 5-1015, SILVER..., Silver Spring, MD 20906
$205,000

2 beds

|

2 baths

|

980 sq ft

|

Condo

3330 N LEISURE WORLD BLVD 5-1015, SILVER...
Heritage Harbour 940 ASTERN WAY 309, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$389,900

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

940 ASTERN WAY 309, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
The Villages At Woodholme 8523 SNOWREATH RD # 8523, BALTIMORE, MD,..., Baltimore, MD 21208
$479,900

3 beds

|

4 baths

|

4,423 sq ft

|

Condo

8523 SNOWREATH RD # 8523, BALTIMORE, MD,...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Four Seasons at Kent Island 630 WARBLER WAY 2224, CHESTER, MD, 21619, Chester, MD 21619
$724,900

2 beds

|

3 baths

|

2,602 sq ft

|

Condo

630 WARBLER WAY 2224, CHESTER, MD, 21619
Four Seasons at Kent Island 630 WARBLER WAY 2222, CHESTER, MD, 21619, Chester, MD 21619
$574,900

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

630 WARBLER WAY 2222, CHESTER, MD, 21619
The Village at Cabin Branch 13230 PETREL ST UNIT 2208, CLARKSBURG, M..., Clarksburg, MD 20871
$574,990

2 beds

|

2 baths

|

1,702 sq ft

|

Condo

13230 PETREL ST UNIT 2208, CLARKSBURG, M...
Gatherings at Cabin Branch 13230 PETREL ST UNIT 2208, CLARKSBURG, M..., Clarksburg, MD 20871
$574,990

2 beds

|

2 baths

|

1,702 sq ft

|

Condo

13230 PETREL ST UNIT 2208, CLARKSBURG, M...
The Village at Cabin Branch 13230 PETREL ST UNIT 2104, CLARKSBURG, M..., Clarksburg, MD 20871
$549,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13230 PETREL ST UNIT 2104, CLARKSBURG, M...
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.
Gatherings at Cabin Branch 13230 PETREL ST UNIT 2104, CLARKSBURG, M..., Clarksburg, MD 20871
$549,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13230 PETREL ST UNIT 2104, CLARKSBURG, M...
Gatherings at Cabin Branch 13210 PETREL ST UNIT 3304, CLARKSBURG, M..., Clarksburg, MD 20871
$474,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST UNIT 3304, CLARKSBURG, M...
The Village at Cabin Branch 13210 PETREL ST UNIT 3304, CLARKSBURG, M..., Clarksburg, MD 20871
$474,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST UNIT 3304, CLARKSBURG, M...
Central Parke at Victoria Falls 13401 BELLE CHASSE BLVD 411, LAUREL, MD,..., Laurel, MD 20707
$399,000

2 beds

|

2 baths

|

1,673 sq ft

|

Condo

13401 BELLE CHASSE BLVD 411, LAUREL, MD,...
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD APT 512, SILVE..., Silver Spring, MD 20906
$239,000

2 beds

|

2 baths

|

1,260 sq ft

|

Condo

3200 N LEISURE WORLD BLVD APT 512, SILVE...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD APT 702, SILVE..., Silver Spring, MD 20906
$295,000

2 beds

|

2 baths

|

1,090 sq ft

|

Condo

3200 N LEISURE WORLD BLVD APT 702, SILVE...
Four Seasons at Kent Island 190 HARRIER WAY 11, CHESTER, MD, 21619, Chester, MD 21619
$540,000

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

190 HARRIER WAY 11, CHESTER, MD, 21619
Leisure World® of Maryland 3360 GLENEAGLES DR 71-2B, SILVER SPRING,..., Silver Spring, MD 20906
$141,000

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

3360 GLENEAGLES DR 71-2B, SILVER SPRING,...
Emerald Pointe 19554 TURQUOISE DR V219, HAGERSTOWN, MD,..., Hagerstown, MD 21742
$484,900

2 beds

|

2 baths

19554 TURQUOISE DR V219, HAGERSTOWN, MD,...
Community: Emerald Pointe
The Paddock at Equine Meadows 227 JUTLAND WAY, RED LION, PA, 17356, Red Lion, PA 17356
$410,000

3 beds

|

3 baths

|

3,210 sq ft

|

Condo

227 JUTLAND WAY, RED LION, PA, 17356

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544 homes near New Windsor
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