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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
The Hamlets at South River Colony 411 HAMLET CLUB DR UNIT 304, EDGEWATER, ..., Edgewater, MD 21037
$400,000

2 beds

|

2 baths

|

1,534 sq ft

|

Condo

411 HAMLET CLUB DR UNIT 304, EDGEWATER, ...
Leisure World® of Maryland 3110 ADDERLEY CT # 245-A, SILVER SPRING,..., Silver Spring, MD 20906
$285,000

2 beds

|

2 baths

|

998 sq ft

|

Condo

3110 ADDERLEY CT # 245-A, SILVER SPRING,...
The Woodlands of Urbana 3207 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$609,900

3 beds

|

3 baths

|

1,677 sq ft

3207 THORNAPPLE DR, FREDERICK, MD, 21704
Leisure World® of Maryland 2921 N LEISURE WORLD BLVD 1-316, SILVER ..., Silver Spring, MD 20906
$145,000

1 beds

|

2 baths

|

803 sq ft

|

Condo

2921 N LEISURE WORLD BLVD 1-316, SILVER ...
Leisure World® of Maryland 15101 INTERLACHEN DR 1-123, SILVER SPRIN..., Silver Spring, MD 20906
$234,900

2 beds

|

2 baths

|

1,225 sq ft

|

Condo

15101 INTERLACHEN DR 1-123, 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 15115 INTERLACHEN DR 3-107, SILVER SPRIN..., Silver Spring, MD 20906
$339,900

3 beds

|

3 baths

|

1,530 sq ft

|

Condo

15115 INTERLACHEN DR 3-107, SILVER SPRIN...
Cameron Grove 14040 NEW ACADIA LN APT 406, UPPER MARLB..., Upper Marlboro, MD 20774
$330,000

2 beds

|

2 baths

|

1,280 sq ft

|

Condo

14040 NEW ACADIA LN APT 406, UPPER MARLB...
Community: Cameron Grove
Leisure World® of Maryland 14507 ELMHAN CT # 182-B, SILVER SPRING, ..., Silver Spring, MD 20906
$459,000

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

14507 ELMHAN CT # 182-B, SILVER SPRING, ...
The Courtyards at Waverly Woods 2740 EMMA STONE DR, MARRIOTTSVILLE, MD, ..., Marriottsville, MD 21104
$900,000

3 beds

|

3 baths

|

2,654 sq ft

2740 EMMA STONE DR, MARRIOTTSVILLE, MD, ...
Bay Bridge Cove 312 TOPSIDE DR 223, STEVENSVILLE, MD, 21..., Stevensville, MD 21666
$665,000

3 beds

|

3 baths

|

2,844 sq ft

|

Condo

312 TOPSIDE DR 223, STEVENSVILLE, MD, 21...
Community: Bay Bridge Cove
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.
Snowden Overlook 8656 VAST ROSE DR 23, COLUMBIA, MD, 2104..., Columbia, MD 21045
$775,000

4 beds

|

5 baths

|

3,719 sq ft

|

Condo

8656 VAST ROSE DR 23, COLUMBIA, MD, 2104...
Community: Snowden Overlook
Snowden Overlook 8736 ENDLESS OCEAN WAY 24, COLUMBIA, MD,..., Columbia, MD 21045
$699,000

3 beds

|

4 baths

|

3,480 sq ft

|

Condo

8736 ENDLESS OCEAN WAY 24, COLUMBIA, MD,...
Community: Snowden Overlook
Snowden Overlook 8740 ENDLESS OCEAN WAY 26, COLUMBIA, MD,..., Columbia, MD 21045
$739,900

3 beds

|

4 baths

|

3,540 sq ft

|

Condo

8740 ENDLESS OCEAN WAY 26, COLUMBIA, MD,...
Community: Snowden Overlook
Snowden Overlook 8861 SHINING OCEANS WAY 27, COLUMBIA, MD..., Columbia, MD 21045
$670,000

3 beds

|

4 baths

|

4,233 sq ft

|

Condo

8861 SHINING OCEANS WAY 27, COLUMBIA, MD...
Community: Snowden Overlook
Leisure World® of Maryland 3311 S LEISURE WORLD BLVD 99-3D, SILVER ..., Silver Spring, MD 20906
$100,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

3311 S LEISURE WORLD BLVD 99-3D, SILVER ...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Four Seasons at Kent Island 3000 HERONS NEST WAY UNIT 11, CHESTER, M..., Chester, MD 21619
$555,900

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

3000 HERONS NEST WAY UNIT 11, CHESTER, M...
Heritage Harbour 2828 BERTH CT, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$500,000

2 beds

|

2 baths

|

1,434 sq ft

2828 BERTH CT, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Legacy at Fallston Commons 331 TUFTON CIR # 102, FALLSTON, MD, 2104..., Fallston, MD 21047
$559,000

3 beds

|

4 baths

|

3,344 sq ft

|

Condo

331 TUFTON CIR # 102, FALLSTON, MD, 2104...
The Village at Foxfield 1 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$574,900

3 beds

|

3 baths

|

3,161 sq ft

1 KELLER LN, MIDDLETOWN, MD, 21769
Leisure World® of Maryland 2900 N LEISURE WORLD BLVD APT 209, SILVE..., Silver Spring, MD 20906
$255,000

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

2900 N LEISURE WORLD BLVD APT 209, SILVE...
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 Village at Cabin Branch 13444 PETREL ST, CLARKSBURG, MD, 20871, Clarksburg, MD 20871
$564,999

3 beds

|

3 baths

|

1,933 sq ft

13444 PETREL ST, CLARKSBURG, MD, 20871
Gatherings at Cabin Branch 13444 PETREL ST, CLARKSBURG, MD, 20871, Clarksburg, MD 20871
$564,999

3 beds

|

3 baths

|

1,933 sq ft

13444 PETREL ST, CLARKSBURG, MD, 20871
Leisure World® of Maryland 15101 INTERLACHEN DR 1-625, SILVER SPRIN..., Silver Spring, MD 20906
$175,000

1 beds

|

1 baths

|

965 sq ft

|

Condo

15101 INTERLACHEN DR 1-625, SILVER SPRIN...
Legacy at Gateway 636 WALLINGFORD RD UNIT 2C, BEL AIR, MD,..., Bel Air, MD 21014
$420,000

2 beds

|

3 baths

|

1,799 sq ft

|

Condo

636 WALLINGFORD RD UNIT 2C, BEL AIR, MD,...
Community: Legacy at Gateway
Leisure World® of Maryland 15032 WESTHOLM CT # 268-D, SILVER SPRING..., Silver Spring, MD 20906
$367,000

3 beds

|

2 baths

|

1,194 sq ft

|

Condo

15032 WESTHOLM CT # 268-D, SILVER SPRING...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 3525 TARKINGTON LN # 63-B, SILVER SPRING..., Silver Spring, MD 20906
$415,000

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

3525 TARKINGTON LN # 63-B, SILVER SPRING...
Castlefield 2855 CHAUNCEY HILL DR # 33, MANCHESTER, ..., Manchester, MD 21102
$549,000

3 beds

|

3 baths

|

2,969 sq ft

|

Condo

2855 CHAUNCEY HILL DR # 33, MANCHESTER, ...
Community: Castlefield
Leisure World® of Maryland 15201 ELKRIDGE WAY 93-2J, SILVER SPRING,..., Silver Spring, MD 20906
$215,000

2 beds

|

2 baths

|

1,030 sq ft

|

Condo

15201 ELKRIDGE WAY 93-2J, SILVER SPRING,...
Courtyards at Waverly Woods East 11100 CHAMBERS CT F, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$395,000

2 beds

|

2 baths

|

1,610 sq ft

|

Condo

11100 CHAMBERS CT F, WOODSTOCK, MD, 2116...
The Enclave at Ellicott Hills 2550 KENSINGTON GDNS 205, ELLICOTT CITY,..., Ellicott City, MD 21043
$400,000

3 beds

|

2 baths

|

1,740 sq ft

|

Condo

2550 KENSINGTON GDNS 205, ELLICOTT CITY,...
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 3005 S LEISURE WORLD BLVD APT 201, SILVE..., Silver Spring, MD 20906
$275,000

2 beds

|

2 baths

|

1,359 sq ft

|

Condo

3005 S LEISURE WORLD BLVD APT 201, SILVE...
Signature Club at Greenview 10611 VICTORIAN AVE 51, NEW MARKET, MD, ..., New Market, MD 21774
$580,000

3 beds

|

3 baths

|

2,200 sq ft

10611 VICTORIAN AVE 51, NEW MARKET, MD, ...
Leisure World® of Maryland 2901 S LEISURE WORLD BLVD 304, SILVER SP..., Silver Spring, MD 20906
$299,900

2 beds

|

2 baths

|

1,229 sq ft

|

Condo

2901 S LEISURE WORLD BLVD 304, SILVER SP...
Cameron Grove 12900 FOX BOW DR 206, UPPER MARLBORO, MD..., Upper Marlboro, MD 20774
$304,000

2 beds

|

2 baths

|

1,270 sq ft

|

Condo

12900 FOX BOW DR 206, UPPER MARLBORO, MD...
Community: Cameron Grove
Four Seasons at Kent Island 224 BAYBERRY DR, CHESTER, MD, 21619, Chester, MD 21619
$599,900

2 beds

|

2 baths

|

1,913 sq ft

224 BAYBERRY DR, CHESTER, MD, 21619
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Heritage Harbour 916 SEXTANT WAY, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$579,995

3 beds

|

4 baths

|

2,640 sq ft

916 SEXTANT WAY, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Leisure World® of Maryland 2921 N LEISURE WORLD BLVD 1-226, SILVER ..., Silver Spring, MD 20906
$160,000

1 beds

|

2 baths

|

803 sq ft

|

Condo

2921 N LEISURE WORLD BLVD 1-226, SILVER ...
Leisure World® of Maryland 15310 PINE ORCHARD DR 84-3K, SILVER SPRI..., Silver Spring, MD 20906
$269,000

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15310 PINE ORCHARD DR 84-3K, SILVER SPRI...
The Reserve at New Windsor 2910 UNION SQUARE RD # 34, NEW WINDSOR, ..., New Windsor, MD 21776
$420,000

3 beds

|

3 baths

|

2,164 sq ft

2910 UNION SQUARE RD # 34, NEW WINDSOR, ...
Leisure World® of Maryland 14801 PENNFIELD CIR APT 203, SILVER SPRI..., Silver Spring, MD 20906
$435,000

3 beds

|

3 baths

|

1,633 sq ft

|

Condo

14801 PENNFIELD CIR APT 203, SILVER SPRI...

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544 homes near New Windsor
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