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

152 communities near New Windsor

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The Reserve at New Windso...
$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 - $500Ks
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 - $600Ks
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
$600Ks - $800Ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
5 rating (31 reviews) Lansdowne Woods of Virgin...
$300Ks - $500Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes
Penn National
$200Ks - $600Ks
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 - $700Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
5 rating (1 reviews) Two Rivers
$500Ks - $700Ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
Cameron Grove
$200Ks - $500Ks
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
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
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
Traditions of America at ...
$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
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 - $600Ks
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
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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 - $600Ks
The Enclave at Ellicott H..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 280 homes
Bay Bridge Cove
$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
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
Crestwood Village 6905 CHOKEBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703
$324,900

2 beds

|

1 baths

|

1,160 sq ft

6905 CHOKEBERRY CT, FREDERICK, MD, 21703
Community: Crestwood Village
Emerald Pointe 13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$424,900

2 beds

|

2 baths

|

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
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
Four Seasons at Kent Island 127 FLYCATCHER WAY, CHESTER, MD, 21619, Chester, MD 21619
$1,100,000

2 beds

|

2 baths

|

1,993 sq ft

127 FLYCATCHER WAY, CHESTER, MD, 21619
Four Seasons at Kent Island 123 FLYCATCHER WAY, CHESTER, MD, 21619, Chester, MD 21619
$1,300,000

3 beds

|

3 baths

|

2,789 sq ft

123 FLYCATCHER WAY, CHESTER, MD, 21619
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Four Seasons at Kent Island 117 FLYCATCHER WAY, CHESTER, MD, 21619, Chester, MD 21619
$1,400,000

3 beds

|

4 baths

|

2,930 sq ft

117 FLYCATCHER WAY, CHESTER, MD, 21619
Four Seasons at Kent Island 111 FLYCATCHER WAY, CHESTER, MD, 21619, Chester, MD 21619
$1,400,000

5 beds

|

5 baths

|

3,225 sq ft

111 FLYCATCHER WAY, CHESTER, MD, 21619
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
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 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...
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 3210 N LEISURE WORLD BLVD 1001, SILVER S..., Silver Spring, MD 20906
$449,000

3 beds

|

2 baths

|

1,544 sq ft

|

Condo

3210 N LEISURE WORLD BLVD 1001, SILVER S...
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
Leisure World® of Maryland 14805 PENNFIELD CIR APT 201, SILVER SPRI..., Silver Spring, MD 20906
$280,000

2 beds

|

2 baths

|

1,136 sq ft

|

Condo

14805 PENNFIELD CIR APT 201, SILVER SPRI...
Leisure World® of Maryland 14507 ELMHAN CT # 182-B, SILVER SPRING, ..., Silver Spring, MD 20906
$434,000

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

14507 ELMHAN CT # 182-B, SILVER SPRING, ...
Carroll Vista 180 SADDLETOP DR # 368, TANEYTOWN, MD, 2..., Taneytown, MD 21787
$410,000

3 beds

|

3 baths

|

1,697 sq ft

|

Condo

180 SADDLETOP DR # 368, TANEYTOWN, MD, 2...
Community: Carroll Vista
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Four Seasons at Saint Margaret's 1507 BROADNECK PL UNIT 404, ANNAPOLIS, M..., Annapolis, MD 21409
$399,000

2 beds

|

2 baths

|

1,235 sq ft

|

Condo

1507 BROADNECK PL UNIT 404, ANNAPOLIS, M...
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...
Courtyards at Waverly Woods East 11180 CHAMBERS CT E, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$424,900

2 beds

|

2 baths

|

1,610 sq ft

|

Condo

11180 CHAMBERS CT E, WOODSTOCK, MD, 2116...
Leisure World® of Maryland 15301 PINE ORCHARD DR 86-3E, SILVER SPRI..., Silver Spring, MD 20906
$269,999

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15301 PINE ORCHARD DR 86-3E, SILVER SPRI...
New Leisure World® of Maryland 15107 INTERLACHEN DR 2-215, SILVER SPRIN..., Silver Spring, MD 20906
$240,000

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

15107 INTERLACHEN DR 2-215, SILVER SPRIN...
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 Leisure World® of Maryland 3436 CHISWICK CT # 45-H, SILVER SPRING, ..., Silver Spring, MD 20906
$249,000

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

3436 CHISWICK CT # 45-H, SILVER SPRING, ...
New Leisure World® of Maryland 15100 INTERLACHEN DR # 4-521, SILVER SPR..., Silver Spring, MD 20906
$339,000

3 beds

|

3 baths

|

1,530 sq ft

|

Condo

15100 INTERLACHEN DR # 4-521, SILVER SPR...
Cameron Grove 13216 FOX BOW DR 403, UPPER MARLBORO, MD..., Upper Marlboro, MD 20774
$333,900

2 beds

|

2 baths

|

1,298 sq ft

|

Condo

13216 FOX BOW DR 403, UPPER MARLBORO, MD...
Community: Cameron Grove
Snowden Overlook 8861 SHINING OCEANS WAY 27, COLUMBIA, MD..., Columbia, MD 21045
$650,000

3 beds

|

4 baths

|

4,233 sq ft

|

Condo

8861 SHINING OCEANS WAY 27, COLUMBIA, MD...
Community: Snowden Overlook
Four Seasons at Kent Island 170 HARRIER WAY UNIT 22, CHESTER, MD, 21..., Chester, MD 21619
$499,000

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

170 HARRIER WAY UNIT 22, CHESTER, MD, 21...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
New Heritage Harbour 1943 MARCONI CIR, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$420,000

2 beds

|

2 baths

|

1,032 sq ft

1943 MARCONI CIR, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Gatherings at Lyndwood 6155 SHADYWOOD RD 204, ELKRIDGE, MD, 210..., Elkridge, MD 21075
$419,500

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

6155 SHADYWOOD RD 204, ELKRIDGE, MD, 210...
New Cedar Ridge at Piney Orchard 8615 WANDERING FOX TRL 208, ODENTON, MD,..., Odenton, MD 21113
$350,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

8615 WANDERING FOX TRL 208, ODENTON, MD,...
Central Parke at Victoria Falls 13120 WINDING TRAIL RD, LAUREL, MD, 2070..., Laurel, MD 20707
$407,000

3 beds

|

3 baths

|

1,472 sq ft

13120 WINDING TRAIL RD, LAUREL, MD, 2070...
Tiree Land Condominiums 301 TIREE CT 303, ABINGDON, MD, 21009, Abingdon, MD 21009
$269,900

2 beds

|

2 baths

|

1,340 sq ft

|

Condo

301 TIREE CT 303, ABINGDON, MD, 21009
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 Leisure World® of Maryland 3310 N LEISURE WORLD BLVD 6-526, SILVER ..., Silver Spring, MD 20906
$279,000

2 beds

|

2 baths

|

1,460 sq ft

|

Condo

3310 N LEISURE WORLD BLVD 6-526, SILVER ...
Leisure World® of Maryland 3005 S LEISURE WORLD BLVD APT 624, SILVE..., Silver Spring, MD 20906
$249,900

2 beds

|

2 baths

|

1,087 sq ft

|

Condo

3005 S LEISURE WORLD BLVD APT 624, SILVE...
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
Heritage Harbour 2900 SHIPMASTER WAY APT 216, ANNAPOLIS, ..., Annapolis, MD 21401
$347,000

2 beds

|

2 baths

|

1,048 sq ft

|

Condo

2900 SHIPMASTER WAY APT 216, ANNAPOLIS, ...
Community: Heritage Harbour
Heritage Harbour 950 BERMUDA LN, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$629,000

4 beds

|

3 baths

|

1,812 sq ft

950 BERMUDA LN, ANNAPOLIS, MD, 21401
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 3100 N LEISURE WORLD BLVD 812, SILVER SP..., Silver Spring, MD 20906
$339,800

2 beds

|

2 baths

|

1,325 sq ft

|

Condo

3100 N LEISURE WORLD BLVD 812, SILVER SP...
Bay Bridge Cove 349 TOPSIDE DR 158, STEVENSVILLE, MD, 21..., Stevensville, MD 21666
$649,900

3 beds

|

3 baths

|

2,284 sq ft

|

Condo

349 TOPSIDE DR 158, STEVENSVILLE, MD, 21...
Community: Bay Bridge Cove
Cameron Grove 1 CAMERON GROVE BLVD 301, UPPER MARLBORO..., Upper Marlboro, MD 20774
$324,900

2 beds

|

2 baths

|

1,364 sq ft

|

Condo

1 CAMERON GROVE BLVD 301, UPPER MARLBORO...
Community: Cameron Grove
Leisure World® of Maryland 3005 S LEISURE WORLD BLVD 426, SILVER SP..., Silver Spring, MD 20906
$317,000

2 beds

|

2 baths

|

1,301 sq ft

|

Condo

3005 S LEISURE WORLD BLVD 426, SILVER SP...
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...

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152 communities near New Windsor
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