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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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Questions? Call us: (443) 647-4690
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
Heritage Harbour 803 COXSWAIN WAY 103, ANNAPOLIS, MD, 214..., Annapolis, MD 21401
$409,900

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

803 COXSWAIN WAY 103, ANNAPOLIS, MD, 214...
Community: Heritage Harbour
Two Rivers 1219 BEAVER TREE DR, ODENTON, MD, 21113, Odenton, MD 21113
$549,900

2 beds

|

3 baths

|

1,410 sq ft

1219 BEAVER TREE DR, ODENTON, MD, 21113
Community: Two Rivers
Leisure World® of Maryland 2904 N LEISURE WORLD BLVD APT 514, SILVE..., Silver Spring, MD 20906
$199,500

1 beds

|

1 baths

|

888 sq ft

|

Condo

2904 N LEISURE WORLD BLVD APT 514, SILVE...
Four Seasons at Kent Island 815 WARBLER WAY, CHESTER, MD, 21619, Chester, MD 21619
$668,900

2 beds

|

2 baths

|

1,993 sq ft

815 WARBLER WAY, CHESTER, MD, 21619
Gatherings at Lyndwood 6155 SHADYWOOD RD 204, ELKRIDGE, MD, 210..., Elkridge, MD 21075
$420,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

6155 SHADYWOOD RD 204, ELKRIDGE, MD, 210...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
The Enclave at Ellicott Hills 2540 KENSINGTON GDNS 406, ELLICOTT CITY,..., Ellicott City, MD 21043
$424,900

2 beds

|

2 baths

|

1,630 sq ft

|

Condo

2540 KENSINGTON GDNS 406, ELLICOTT CITY,...
Emerald Hills 1600 MARTHA CT 301, BEL AIR, MD, 21015, Bel Air, MD 21015
$280,000

3 beds

|

2 baths

|

1,300 sq ft

|

Condo

1600 MARTHA CT 301, BEL AIR, MD, 21015
Community: Emerald Hills
Leisure World® of Maryland 3310 N LEISURE WORLD BLVD 325, SILVER SP..., Silver Spring, MD 20906
$227,000

2 beds

|

2 baths

|

1,115 sq ft

|

Condo

3310 N LEISURE WORLD BLVD 325, SILVER SP...
Crestwood Village 7043 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703
$339,999

2 beds

|

2 baths

|

1,225 sq ft

7043 BASSWOOD RD, FREDERICK, MD, 21703
Community: Crestwood Village
Four Seasons at Kent Island 132 KESTREL LN, CHESTER, MD, 21619, Chester, MD 21619
$995,000

4 beds

|

4 baths

|

3,634 sq ft

132 KESTREL LN, CHESTER, MD, 21619
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 World® of Maryland 3220 LUDHAM DR # 196A, SILVER SPRING, MD..., Silver Spring, MD 20906
$399,900

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

3220 LUDHAM DR # 196A, SILVER SPRING, MD...
Carroll Vista 405 CLUBSIDE DR # 303, TANEYTOWN, MD, 21..., Taneytown, MD 21787
$375,900

3 beds

|

3 baths

|

1,697 sq ft

|

Condo

405 CLUBSIDE DR # 303, TANEYTOWN, MD, 21...
Community: Carroll Vista
Four Seasons at Kent Island 124 NAUSET LN, CHESTER, MD, 21619, Chester, MD 21619
$825,000

3 beds

|

3 baths

|

2,583 sq ft

124 NAUSET LN, CHESTER, MD, 21619
Leisure World® of Maryland 15115 INTERLACHEN DR 3-815, SILVER SPRIN..., Silver Spring, MD 20906
$210,000

2 beds

|

2 baths

|

1,115 sq ft

|

Condo

15115 INTERLACHEN DR 3-815, SILVER SPRIN...
Bay Bridge Cove 440 MOORINGS CIR # 85, STEVENSVILLE, MD,..., Stevensville, MD 21666
$685,000

3 beds

|

3 baths

|

2,812 sq ft

|

Condo

440 MOORINGS CIR # 85, STEVENSVILLE, MD,...
Community: Bay Bridge Cove
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 14809 PENNFIELD CIR APT 406, SILVER SPRI..., Silver Spring, MD 20906
$350,000

2 beds

|

2 baths

|

1,319 sq ft

|

Condo

14809 PENNFIELD CIR APT 406, SILVER SPRI...
The Villages At Woodholme 8500 BRIDALWREATH WAY, PIKESVILLE, MD, 2..., Pikesville, MD 21208
$485,000

4 beds

|

4 baths

|

3,594 sq ft

|

Condo

8500 BRIDALWREATH WAY, PIKESVILLE, MD, 2...
Snowden Overlook 8820 SHINING OCEANS WAY 410, COLUMBIA, M..., Columbia, MD 21045
$499,000

2 beds

|

2 baths

|

1,787 sq ft

|

Condo

8820 SHINING OCEANS WAY 410, COLUMBIA, M...
Community: Snowden Overlook
Leisure World® of Maryland 2904 N LEISURE WORLD BLVD 502, SILVER SP..., Silver Spring, MD 20906
$335,000

2 beds

|

2 baths

|

1,334 sq ft

|

Condo

2904 N LEISURE WORLD BLVD 502, SILVER SP...
Carroll Vista 152 SADDLETOP DR # 354, TANEYTOWN, MD, 2..., Taneytown, MD 21787
$362,500

2 beds

|

2 baths

|

1,679 sq ft

|

Condo

152 SADDLETOP DR # 354, TANEYTOWN, MD, 2...
Community: Carroll Vista
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 Enclave at Ellicott Hills 2520 KENSINGTON GDNS UNIT 401, ELLICOTT ..., Ellicott City, MD 21043
$400,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

2520 KENSINGTON GDNS UNIT 401, ELLICOTT ...
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 115, SILVER SP..., Silver Spring, MD 20906
$300,000

3 beds

|

2 baths

|

1,489 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 115, SILVER SP...
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD APT 514, SILVE..., Silver Spring, MD 20906
$250,000

2 beds

|

2 baths

|

1,035 sq ft

|

Condo

3200 N LEISURE WORLD BLVD APT 514, SILVE...
Leisure World® of Maryland 3638 EDELMAR TER # 123-B, SILVER SPRING,..., Silver Spring, MD 20906
$419,000

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

3638 EDELMAR TER # 123-B, SILVER SPRING,...
Leisure World® of Maryland 15300 BEAVERBROOK CT 88-2B, SILVER SPRIN..., Silver Spring, MD 20906
$269,000

2 beds

|

2 baths

|

1,043 sq ft

|

Condo

15300 BEAVERBROOK CT 88-2B, SILVER SPRIN...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 3322 CHISWICK CT 61-1G, SILVER SPRING, M..., Silver Spring, MD 20906
$93,000

1 beds

|

1 baths

|

635 sq ft

|

Condo

3322 CHISWICK CT 61-1G, SILVER SPRING, M...
Bay Bridge Cove 736 MOORINGS CIR 35, STEVENSVILLE, MD, 2..., Stevensville, MD 21666
$669,000

3 beds

|

3 baths

|

1,906 sq ft

|

Condo

736 MOORINGS CIR 35, STEVENSVILLE, MD, 2...
Community: Bay Bridge Cove
Leisure World® of Maryland 2904 N LEISURE WORLD BLVD 501, SILVER SP..., Silver Spring, MD 20906
$289,000

2 beds

|

2 baths

|

1,111 sq ft

|

Condo

2904 N LEISURE WORLD BLVD 501, SILVER SP...
Heritage Harbour 2600 COMPASS DR, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$509,000

2 beds

|

2 baths

|

1,514 sq ft

2600 COMPASS DR, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
The Enclave at Ellicott Hills 2530 KENSINGTON GDNS UNIT 406, ELLICOTT ..., Ellicott City, MD 21043
$415,000

3 beds

|

2 baths

|

1,750 sq ft

|

Condo

2530 KENSINGTON GDNS UNIT 406, ELLICOTT ...
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 Forest Glen 8612 WINTERGREEN CT 105, ODENTON, MD, 21..., Odenton, MD 21113
$365,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

8612 WINTERGREEN CT 105, ODENTON, MD, 21...
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 918, SILVER SP..., Silver Spring, MD 20906
$309,500

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 918, SILVER SP...
Leisure World® of Maryland 2901 S LEISURE WORLD BLVD 419, SILVER SP..., Silver Spring, MD 20906
$419,000

2 beds

|

2 baths

|

1,774 sq ft

|

Condo

2901 S LEISURE WORLD BLVD 419, SILVER SP...
Gatherings at Lyndwood 6150 SHADYWOOD RD UNIT 401, ELKRIDGE, MD..., Elkridge, MD 21075
$425,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

6150 SHADYWOOD RD UNIT 401, ELKRIDGE, MD...
Leisure World® of Maryland 15100 INTERLACHEN DR # 4-908, SILVER SPR..., Silver Spring, MD 20906
$199,000

2 beds

|

2 baths

|

1,115 sq ft

|

Condo

15100 INTERLACHEN DR # 4-908, SILVER SPR...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Two Rivers 1240 BEAVER TREE DR, ODENTON, MD, 21113, Odenton, MD 21113
$725,000

3 beds

|

4 baths

|

3,144 sq ft

1240 BEAVER TREE DR, ODENTON, MD, 21113
Community: Two Rivers
Courtyards at Waverly Woods East 11150 CHAMBERS CT H, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$410,000

2 beds

|

2 baths

|

1,610 sq ft

|

Condo

11150 CHAMBERS CT H, WOODSTOCK, MD, 2116...
Gatherings at Lyndwood 7315 BROOKVIEW RD UNIT 407, ELKRIDGE, MD..., Elkridge, MD 21075
$450,000

3 beds

|

2 baths

|

1,900 sq ft

|

Condo

7315 BROOKVIEW RD UNIT 407, ELKRIDGE, MD...
Leisure World® of Maryland 15101 INTERLACHEN DR 1-1022, SILVER SPRI..., Silver Spring, MD 20906
$245,000

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

15101 INTERLACHEN DR 1-1022, SILVER SPRI...
Bay Bridge Cove 858 MOORINGS CIR 11, STEVENSVILLE, MD, 2..., Stevensville, MD 21666
$614,000

3 beds

|

2 baths

|

1,906 sq ft

|

Condo

858 MOORINGS CIR 11, STEVENSVILLE, MD, 2...
Community: Bay Bridge Cove

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544 homes near New Windsor
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