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New Windsor, MD 55+ active adult communities & homes for sale - Page 6

461 homes 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 - $600Ks
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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2 rating (1 reviews) Birchwood at Brambleton
$400Ks - $900Ks
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
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 Isla...
$400Ks - $1Ms
Four Seasons at Kent Isla..., Kent Island, MD
New Construction | 55+ age-restricted | Built 2018 - present | 1,079 homes
5 rating (1 reviews) Regency at Dominion Valle...
$400Ks - $500Ks
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
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5 rating (2 reviews) Central Parke at Victoria...
$400Ks
Central Parke at Victoria..., Laurel, MD
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes
The Woodlands of Urbana
$400Ks - $600Ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
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 ...
$400Ks - $500Ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 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.
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
The Courtyards at Waverly...
$300Ks - $800Ks
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 homes
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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
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
Village Crest, Ellicott City, MD
New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 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.
Courtyards at Waverly Woo...
$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
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Questions? Call us: (443) 647-4690
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
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.
Bay Bridge Cove
$600Ks
Bay Bridge Cove, Stevensville, MD
Resale Only | 55+ age-restricted | Built 2016 - 2022 | 273 homes
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
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
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 2510 PAINTER CT, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$484,900

2 beds

|

2 baths

|

1,440 sq ft

2510 PAINTER CT, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Heritage Harbour 950 BERMUDA LN, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$595,000

4 beds

|

3 baths

|

1,812 sq ft

950 BERMUDA LN, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Leisure World® of Maryland 3301 S LEISURE WORLD BLVD 99-2E, SILVER ..., Silver Spring, MD 20906
$102,500

1 beds

|

1 baths

|

800 sq ft

|

Condo

3301 S LEISURE WORLD BLVD 99-2E, SILVER ...
Leisure World® of Maryland 3352 CHISWICK CT 57-3E, SILVER SPRING, M..., Silver Spring, MD 20906
$103,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

3352 CHISWICK CT 57-3E, SILVER SPRING, M...
Leisure World® of Maryland 3322 CHISWICK CT 61-1G, SILVER SPRING, M..., Silver Spring, MD 20906
$89,000

1 beds

|

1 baths

|

635 sq ft

|

Condo

3322 CHISWICK CT 61-1G, SILVER SPRING, M...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
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...
The Woodlands of Urbana 3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$609,997

3 beds

|

3 baths

|

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704
Gatherings at Forest Glen 8612 WINTERGREEN CT 105, ODENTON, MD, 21..., Odenton, MD 21113
$349,900

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

8612 WINTERGREEN CT 105, ODENTON, MD, 21...
Leisure World® of Maryland 3386 CHISWICK CT 50-1A, SILVER SPRING, M..., Silver Spring, MD 20906
$132,000

1 beds

|

1 baths

|

1,014 sq ft

|

Condo

3386 CHISWICK CT 50-1A, SILVER SPRING, 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.
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...
Castlefield 2841 CHAUNCEY HILL DR # 28, MANCHESTER, ..., Manchester, MD 21102
$529,900

3 beds

|

3 baths

|

3,188 sq ft

|

Condo

2841 CHAUNCEY HILL DR # 28, MANCHESTER, ...
Community: Castlefield
Cameron Grove 1 ROSEBUD CT, UPPER MARLBORO, MD, 20774, Upper Marlboro, MD 20774
$400,000

2 beds

|

2 baths

|

1,298 sq ft

1 ROSEBUD CT, UPPER MARLBORO, MD, 20774
Community: Cameron Grove
Bethany Glen 9803 BLUE IVY WAY, ELLICOTT CITY, MD, 21..., Ellicott City, MD 21042
$787,888

3 beds

|

4 baths

|

2,795 sq ft

9803 BLUE IVY WAY, ELLICOTT CITY, MD, 21...
Community: Bethany Glen
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Four Seasons at Kent Island 176 FLAGSTAFF WAY 2424, CHESTER, MD, 216..., Chester, MD 21619
$935,990

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

176 FLAGSTAFF WAY 2424, CHESTER, MD, 216...
Four Seasons at Kent Island 141 REDSTART DR, CHESTER, MD, 21619, Chester, MD 21619
$1,019,990

3 beds

|

3 baths

|

2,789 sq ft

141 REDSTART DR, CHESTER, MD, 21619
Four Seasons at Kent Island 110 KINGLET CT, CHESTER, MD, 21619, Chester, MD 21619
$969,990

5 beds

|

5 baths

|

3,225 sq ft

110 KINGLET CT, CHESTER, MD, 21619
Leisure World® of Maryland 15107 INTERLACHEN DR 2-321, SILVER SPRIN..., Silver Spring, MD 20906
$205,000

2 beds

|

2 baths

|

990 sq ft

15107 INTERLACHEN DR 2-321, 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.
Four Seasons at Kent Island 170 HARRIER WAY 34, CHESTER, MD, 21619, Chester, MD 21619
$699,900

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

170 HARRIER WAY 34, CHESTER, MD, 21619
The Village at Freedom Hills 13948 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740
$374,900

2 beds

|

2 baths

|

1,430 sq ft

13948 PATRIOT WAY, HAGERSTOWN, MD, 21740
The Enclave at Ellicott Hills 2540 KENSINGTON GDNS UNIT 303, ELLICOTT ..., Ellicott City, MD 21043
$390,000

2 beds

|

2 baths

|

1,640 sq ft

|

Condo

2540 KENSINGTON GDNS UNIT 303, ELLICOTT ...
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,...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 15211 ELKRIDGE WAY 94-3C, SILVER SPRING,..., Silver Spring, MD 20906
$218,500

2 beds

|

2 baths

|

1,030 sq ft

|

Condo

15211 ELKRIDGE WAY 94-3C, SILVER SPRING,...
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...
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
Leisure World® of Maryland 15205 TOTTENHAM TER # 24-B, SILVER SPRIN..., Silver Spring, MD 20906
$435,000

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

15205 TOTTENHAM TER # 24-B, 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.
Leisure World® of Maryland 15107 INTERLACHEN DR 2-119, SILVER SPRIN..., Silver Spring, MD 20906
$205,000

2 beds

|

2 baths

|

950 sq ft

|

Condo

15107 INTERLACHEN DR 2-119, SILVER SPRIN...
Eden Brook 1012 SAMANTHA LN APT 301, ODENTON, MD, 2..., Odenton, MD 21113
$350,000

2 beds

|

2 baths

|

1,612 sq ft

|

Condo

1012 SAMANTHA LN APT 301, ODENTON, MD, 2...
Community: Eden Brook
Courtyards at Waverly Woods East 11130 CHAMBERS CT B, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$413,000

2 beds

|

2 baths

|

1,607 sq ft

|

Condo

11130 CHAMBERS CT B, WOODSTOCK, MD, 2116...
Two Rivers 2834 DRAGON FLY WAY, ODENTON, MD, 21113, Odenton, MD 21113
$570,000

2 beds

|

2 baths

|

1,886 sq ft

2834 DRAGON FLY WAY, ODENTON, MD, 21113
Community: Two Rivers
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
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 15101 INTERLACHEN DR 1-612, SILVER SPRIN..., Silver Spring, MD 20906
$269,900

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

15101 INTERLACHEN DR 1-612, SILVER SPRIN...
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
The Villages At Woodholme 4223 CHASTETREE CT, PIKESVILLE, MD, 2120..., Pikesville, MD 21208
$469,000

4 beds

|

4 baths

|

3,800 sq ft

|

Condo

4223 CHASTETREE CT, PIKESVILLE, MD, 2120...
Cameron Grove 1 CAMERON GROVE BLVD APT 202, UPPER MARL..., Upper Marlboro, MD 20774
$310,000

2 beds

|

2 baths

|

1,208 sq ft

|

Condo

1 CAMERON GROVE BLVD APT 202, UPPER MARL...
Community: Cameron Grove
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 3314 CHISWICK CT 62-1G, SILVER SPRING, M..., Silver Spring, MD 20906
$92,000

1 beds

|

1 baths

|

635 sq ft

|

Condo

3314 CHISWICK CT 62-1G, SILVER SPRING, M...
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...
Emerald Hills 1603 MARTHA CT 101, BEL AIR, MD, 21015, Bel Air, MD 21015
$311,500

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

1603 MARTHA CT 101, BEL AIR, MD, 21015
Community: Emerald Hills
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, ...
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
$330,000

2 beds

|

2 baths

|

1,325 sq ft

|

Condo

3100 N LEISURE WORLD BLVD 812, SILVER SP...
Bethany Glen 9798 BLUE IVY WAY, ELLICOTT CITY, MD, 21..., Ellicott City, MD 21042
$814,990

3 beds

|

3 baths

|

3,337 sq ft

9798 BLUE IVY WAY, ELLICOTT CITY, MD, 21...
Community: Bethany Glen

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