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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
New Gatherings at Ellicott Mills 8547 COLTRANE CT 39, ELLICOTT CITY, MD, ..., Ellicott City, MD 21043
$615,000

3 beds

|

3 baths

|

2,667 sq ft

|

Condo

8547 COLTRANE CT 39, ELLICOTT CITY, MD, ...
Leisure World® of Maryland 3613 EDELMAR TER # 131-B, SILVER SPRING,..., Silver Spring, MD 20906
$425,000

3 beds

|

2 baths

|

1,430 sq ft

|

Condo

3613 EDELMAR TER # 131-B, SILVER SPRING,...
Leisure World® of Maryland 3500 FOREST EDGE DR 15-2E, SILVER SPRING..., Silver Spring, MD 20906
$159,900

2 beds

|

2 baths

|

1,157 sq ft

|

Condo

3500 FOREST EDGE DR 15-2E, SILVER SPRING...
New Crestwood Village 5722 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703
$349,000

2 beds

|

2 baths

|

1,264 sq ft

5722 BOX ELDER CT, FREDERICK, MD, 21703
Community: Crestwood Village
Heritage Harbour 2737 YEOMANS LANTERN CT, ANNAPOLIS, MD, ..., Annapolis, MD 21401
$529,999

2 beds

|

2 baths

|

1,514 sq ft

2737 YEOMANS LANTERN CT, ANNAPOLIS, MD, ...
Community: Heritage Harbour
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
New Signature Club at Greenview 10576 EDWARDIAN LN 132, NEW MARKET, MD, ..., New Market, MD 21774
$619,000

3 beds

|

4 baths

|

3,655 sq ft

|

Condo

10576 EDWARDIAN LN 132, NEW MARKET, MD, ...
Leisure World® of Maryland 3314 CHISWICK CT 62-1G, SILVER SPRING, M..., Silver Spring, MD 20906
$97,000

1 beds

|

1 baths

|

635 sq ft

|

Condo

3314 CHISWICK CT 62-1G, SILVER SPRING, M...
Leisure World® of Maryland 15115 INTERLACHEN DR 3-802, SILVER SPRIN..., Silver Spring, MD 20906
$164,900

1 beds

|

1 baths

|

850 sq ft

|

Condo

15115 INTERLACHEN DR 3-802, SILVER SPRIN...
New Leisure World® of Maryland 15101 INTERLACHEN DR 1-102, SILVER SPRIN..., Silver Spring, MD 20906
$180,000

1 beds

|

1 baths

|

860 sq ft

|

Condo

15101 INTERLACHEN DR 1-102, SILVER SPRIN...
Heritage Harbour 2664 COMPASS DR, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$455,000

2 beds

|

2 baths

|

1,145 sq ft

2664 COMPASS DR, 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.
New Village Crest 8125 HICKORY HIGH CT L, ELLICOTT CITY, M..., Ellicott City, MD 21043
$395,000

2 beds

|

2 baths

|

1,574 sq ft

|

Condo

8125 HICKORY HIGH CT L, ELLICOTT CITY, M...
Community: Village Crest
CobbleStone Estates 9616 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740
$395,000

2 beds

|

2 baths

|

1,561 sq ft

9616 COBBLE STONE CT, HAGERSTOWN, MD, 21...
Community: CobbleStone Estates
Castlefield 2748 VISTAS DR # 11, MANCHESTER, MD, 211..., Manchester, MD 21102
$495,000

3 beds

|

3 baths

|

2,750 sq ft

|

Condo

2748 VISTAS DR # 11, MANCHESTER, MD, 211...
Community: Castlefield
Courts of Clarksburg 832 BUTTERFLY WEED DR, GERMANTOWN, MD, 2..., Germantown, MD 20876
$797,435

2 beds

|

3 baths

|

2,784 sq ft

832 BUTTERFLY WEED DR, GERMANTOWN, MD, 2...
Cameron Grove 13507 LEESBURG PL, UPPER MARLBORO, MD, 2..., Upper Marlboro, MD 20774
$395,000

2 beds

|

2 baths

|

1,469 sq ft

13507 LEESBURG PL, UPPER MARLBORO, MD, 2...
Community: Cameron Grove
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Cedar Ridge at Piney Orchard 8615 FLUTTERING LEAF TRL 404, ODENTON, M..., Odenton, MD 21113
$375,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

8615 FLUTTERING LEAF TRL 404, ODENTON, M...
Village Crest 8115 YELLOW PINE DR L, ELLICOTT CITY, MD..., Ellicott City, MD 21043
$385,000

2 beds

|

2 baths

|

1,574 sq ft

|

Condo

8115 YELLOW PINE DR L, ELLICOTT CITY, MD...
Community: Village Crest
New Two Rivers 2630 DRAGON FLY WAY, ODENTON, MD, 21113, Odenton, MD 21113
$544,900

2 beds

|

2 baths

|

1,668 sq ft

|

Condo

2630 DRAGON FLY WAY, ODENTON, MD, 21113
Community: Two Rivers
New Leisure World® of Maryland 15107 INTERLACHEN DR 2-822, SILVER SPRIN..., Silver Spring, MD 20906
$249,999

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

15107 INTERLACHEN DR 2-822, SILVER SPRIN...
Watershed 1202 CRESTED WOOD DR, LAUREL, MD, 20724, Laurel, MD 20724
$664,990

4 beds

|

4 baths

|

2,660 sq ft

1202 CRESTED WOOD DR, LAUREL, MD, 20724
Community: Watershed
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 34, CHESTER, MD, 21619, Chester, MD 21619
$740,000

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

170 HARRIER WAY 34, CHESTER, MD, 21619
Central Parke at Victoria Falls 13801 BELLE CHASSE BLVD 212, LAUREL, MD,..., Laurel, MD 20707
$389,500

2 beds

|

2 baths

|

1,673 sq ft

|

Condo

13801 BELLE CHASSE BLVD 212, LAUREL, MD,...
Central Parke at Victoria Falls 13501 BELLE CHASSE BLVD 215, LAUREL, MD,..., Laurel, MD 20707
$410,000

2 beds

|

2 baths

|

1,919 sq ft

|

Condo

13501 BELLE CHASSE BLVD 215, LAUREL, MD,...
Heritage Harbour 825 COXSWAIN WAY, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$545,000

2 beds

|

2 baths

|

1,691 sq ft

825 COXSWAIN WAY, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Leisure World® of Maryland 3310 N LEISURE WORLD BLVD 124, SILVER SP..., Silver Spring, MD 20906
$250,000

2 beds

|

2 baths

|

1,195 sq ft

|

Condo

3310 N LEISURE WORLD BLVD 124, SILVER SP...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Legacy at Fallston Commons 309 LENNOX DR, FALLSTON, MD, 21047, Fallston, MD 21047
$559,990

3 beds

|

4 baths

|

2,444 sq ft

|

Condo

309 LENNOX DR, FALLSTON, MD, 21047
Four Seasons at Saint Margaret's 901 NOAH WINFIELD TER UNIT 102, ANNAPOLI..., Annapolis, MD 21409
$539,000

2 beds

|

2 baths

|

1,732 sq ft

|

Condo

901 NOAH WINFIELD TER UNIT 102, ANNAPOLI...
Carroll Vista 102 BUTTERFLY DR # 55, TANEYTOWN, MD, 21..., Taneytown, MD 21787
$374,900

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

102 BUTTERFLY DR # 55, TANEYTOWN, MD, 21...
Community: Carroll Vista
Liberty Place 40 LIBERTY RD T, SYKESVILLE, MD, 21784, Sykesville, MD 21784
$334,900

2 beds

|

2 baths

|

1,186 sq ft

|

Condo

40 LIBERTY RD T, SYKESVILLE, MD, 21784
Community: Liberty Place
Leisure World® of Maryland 3504 FITZHUGH LN # 49-C, SILVER SPRING, ..., Silver Spring, MD 20906
$519,000

3 beds

|

2 baths

|

1,266 sq ft

|

Condo

3504 FITZHUGH LN # 49-C, SILVER SPRING, ...
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.
Cameron Grove 13006 BRICE CT, UPPER MARLBORO, MD, 2077..., Upper Marlboro, MD 20774
$485,000

3 beds

|

3 baths

|

2,601 sq ft

13006 BRICE CT, UPPER MARLBORO, MD, 2077...
Community: Cameron Grove
The Village at Cabin Branch 13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$479,900

3 beds

|

3 baths

|

1,590 sq ft

13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Gatherings at Cabin Branch 13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$479,900

3 beds

|

3 baths

|

1,590 sq ft

13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Two Rivers 2834 DRAGON FLY WAY, ODENTON, MD, 21113, Odenton, MD 21113
$575,000

2 beds

|

2 baths

|

1,886 sq ft

2834 DRAGON FLY WAY, ODENTON, MD, 21113
Community: Two Rivers
Leisure World® of Maryland 3210 N LEISURE WORLD BLVD 1001, SILVER S..., Silver Spring, MD 20906
$489,000

3 beds

|

2 baths

|

1,544 sq ft

|

Condo

3210 N LEISURE WORLD BLVD 1001, SILVER S...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Central Parke at Victoria Falls 13106 OLD FIELD TER, LAUREL, MD, 20707, Laurel, MD 20707
$614,900

4 beds

|

3 baths

|

3,304 sq ft

13106 OLD FIELD TER, LAUREL, MD, 20707
The Courtyards at Waverly Woods 2241 JOHN GRAVEL RD M, MARRIOTTSVILLE, M..., Marriottsville, MD 21104
$400,000

2 beds

|

2 baths

|

1,438 sq ft

|

Condo

2241 JOHN GRAVEL RD M, MARRIOTTSVILLE, M...
Courtyards at Waverly Woods East 11110 CHAMBERS CT A, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$380,000

2 beds

|

2 baths

|

1,595 sq ft

|

Condo

11110 CHAMBERS CT A, WOODSTOCK, MD, 2116...
Watershed 2104 FOXGLOVE LN, LAUREL, MD, 20724, Laurel, MD 20724
$698,890

3 beds

|

4 baths

|

2,695 sq ft

2104 FOXGLOVE LN, LAUREL, MD, 20724
Community: Watershed
Watershed 1354 CRESTED WOOD DR DR, LAUREL, MD, 207..., Laurel, MD 20724
$599,990

3 beds

|

4 baths

|

2,660 sq ft

1354 CRESTED WOOD DR DR, LAUREL, MD, 207...
Community: Watershed

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544 homes near New Windsor
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