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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
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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 - $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
Amblebrook 122 ELDERBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$416,990

3 beds

|

2 baths

|

1,813 sq ft

122 ELDERBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Country Manor 81 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$205,000

2 beds

|

2 baths

|

1,550 sq ft

81 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
Traditions of America at Silver Spring 86 PRESIDENTS DR, MECHANICSBURG, PA, 170..., Mechanicsburg, PA 17050
$515,000

2 beds

|

2 baths

|

2,036 sq ft

|

Condo

86 PRESIDENTS DR, MECHANICSBURG, PA, 170...
Penn National 3826 FARMSTEAD DR, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222
$349,000

3 beds

|

4 baths

|

3,106 sq ft

3826 FARMSTEAD DR, FAYETTEVILLE, PA, 172...
Community: Penn National
Spring Valley Estates 11802 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$388,900

4 beds

|

3 baths

|

2,035 sq ft

11802 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Spring Valley Estates 11798 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$388,900

4 beds

|

3 baths

|

2,035 sq ft

11798 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Amblebrook 118 NEW VISTA WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$484,900

2 beds

|

2 baths

|

1,733 sq ft

118 NEW VISTA WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
Penn National 7010 FAIRWAY OAKS, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222
$379,900

3 beds

|

2 baths

7010 FAIRWAY OAKS, FAYETTEVILLE, PA, 172...
Community: Penn National
Alden Place 1012 ENGLISH DR, LEBANON, PA, 17042, Lebanon, PA 17042
$325,000

2 beds

|

2 baths

|

1,904 sq ft

1012 ENGLISH DR, LEBANON, PA, 17042
Community: Alden Place
Amblebrook 52 TULIP TREE WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$349,900

2 beds

|

2 baths

|

1,500 sq ft

52 TULIP TREE WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
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.
Penn National 2375 ARONIMINK CIR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$274,000

2 beds

|

2 baths

2375 ARONIMINK CIR, FAYETTEVILLE, PA, 17...
Community: Penn National
Amblebrook 126 ELDERBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$399,990

3 beds

|

2 baths

|

1,736 sq ft

126 ELDERBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Winding Creek 416 PINNACLE RIDGE DR, ANNVILLE, PA, 170..., Annville, PA 17003
$594,900

2 beds

|

2 baths

|

2,246 sq ft

416 PINNACLE RIDGE DR, ANNVILLE, PA, 170...
Community: Winding Creek
Winding Creek 524 WINDING CREEK BLVD, ANNVILLE, PA, 17..., Annville, PA 17003
$554,800

2 beds

|

2 baths

|

1,741 sq ft

524 WINDING CREEK BLVD, ANNVILLE, PA, 17...
Community: Winding Creek
Winding Creek 214 GRAND SUMMIT DR, ANNVILLE, PA, 17003, Annville, PA 17003
$554,400

2 beds

|

2 baths

|

1,884 sq ft

214 GRAND SUMMIT DR, ANNVILLE, PA, 17003
Community: Winding Creek
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Amblebrook 104 CHOKEBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$395,990

3 beds

|

2 baths

|

1,402 sq ft

104 CHOKEBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Cherry Tree 412 HAWTHORN LN # 67, HANOVER, PA, 17331, Hanover, PA 17331
$319,900

3 beds

|

2 baths

|

1,612 sq ft

412 HAWTHORN LN # 67, HANOVER, PA, 17331
Community: Cherry Tree
Cortland Park 787 AURORA DR, MECHANICSBURG, PA, 17055, Mechanicsburg, PA 17055
$489,900

3 beds

|

3 baths

|

2,360 sq ft

787 AURORA DR, MECHANICSBURG, PA, 17055
Community: Cortland Park
Penn National 5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P..., Fayetteville, PA 17222
$204,000

2 beds

|

2 baths

|

1,598 sq ft

|

Condo

5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P...
Community: Penn National
Carmella 110 BLUEBELL DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050
$415,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

110 BLUEBELL DR, MECHANICSBURG, PA, 1705...
Community: Carmella
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.
Wynfield at Millersville 105 VILLAGE DR, MILLERSVILLE, PA, 17551, Millersville, PA 17551
$451,000

3 beds

|

3 baths

|

2,487 sq ft

105 VILLAGE DR, MILLERSVILLE, PA, 17551
Heritage Run 113 ALLWEIN DR, LEBANON, PA, 17042, Lebanon, PA 17042
$344,900

2 beds

|

2 baths

|

1,300 sq ft

113 ALLWEIN DR, LEBANON, PA, 17042
Community: Heritage Run
Heritage Run 109 ALLWEIN DR, LEBANON, PA, 17042, Lebanon, PA 17042
$447,900

2 beds

|

2 baths

|

1,689 sq ft

109 ALLWEIN DR, LEBANON, PA, 17042
Community: Heritage Run
Heritage Run 111 ALLWEIN DR, LEBANON, PA, 17042, Lebanon, PA 17042
$421,500

2 beds

|

2 baths

|

1,590 sq ft

111 ALLWEIN DR, LEBANON, PA, 17042
Community: Heritage Run
Amblebrook 85 QUIET CREEK DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$599,990

2 beds

|

2 baths

|

2,220 sq ft

85 QUIET CREEK DR, GETTYSBURG, PA, 17325
Community: Amblebrook
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Amblebrook 215 RUSTIC WOOD DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$695,000

3 beds

|

3 baths

|

2,971 sq ft

215 RUSTIC WOOD DR, GETTYSBURG, PA, 1732...
Community: Amblebrook
Amblebrook 141 GRAND OVERLOOK DR, GETTYSBURG, PA, 1..., Gettysburg, PA 17325
$349,990

3 beds

|

3 baths

141 GRAND OVERLOOK DR, GETTYSBURG, PA, 1...
Community: Amblebrook
Amblebrook 211 GRAND OVERLOOK DR, GETTYSBURG, PA, 1..., Gettysburg, PA 17325
$379,990

2 beds

|

2 baths

|

1,518 sq ft

211 GRAND OVERLOOK DR, GETTYSBURG, PA, 1...
Community: Amblebrook
Amblebrook 33 ROLLING HILLS WAY, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$450,000

2 beds

|

2 baths

|

1,852 sq ft

33 ROLLING HILLS WAY, GETTYSBURG, PA, 17...
Community: Amblebrook
Creek View 118 GLENRIDGE DR, CARLISLE, PA, 17015, Carlisle, PA 17015
$269,710

2 beds

|

2 baths

|

1,408 sq ft

118 GLENRIDGE DR, CARLISLE, PA, 17015
Community: Creek View
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.
Wynfield at Annville 117 BELLFLOWER AVE, ANNVILLE, PA, 17003, Annville, PA 17003
$574,990

2 beds

|

2 baths

|

1,758 sq ft

117 BELLFLOWER AVE, ANNVILLE, PA, 17003
Wynfield at Millersville 102 VILLAGE DR, MILLERSVILLE, PA, 17551, Millersville, PA 17551
$423,900

3 beds

|

3 baths

|

2,487 sq ft

102 VILLAGE DR, MILLERSVILLE, PA, 17551
Villas at Cattail 152 ST MICHAELS WAY, HANOVER, PA, 17331, Hanover, PA 17331
$400,000

3 beds

|

2 baths

|

2,165 sq ft

152 ST MICHAELS WAY, HANOVER, PA, 17331
Community: Villas at Cattail
Amblebrook 294 RUSTIC WOOD DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$574,900

2 beds

|

2 baths

|

2,474 sq ft

294 RUSTIC WOOD DR, GETTYSBURG, PA, 1732...
Community: Amblebrook
Cherry Tree 679 CYPRESS DR # 76, HANOVER, PA, 17331, Hanover, PA 17331
$324,900

3 beds

|

2 baths

|

1,568 sq ft

679 CYPRESS DR # 76, HANOVER, PA, 17331
Community: Cherry Tree
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Amblebrook 170 LIVELY STREAM WAY, GETTYSBURG, PA, 1..., Gettysburg, PA 17325
$1,100,000

3 beds

|

4 baths

|

4,085 sq ft

170 LIVELY STREAM WAY, GETTYSBURG, PA, 1...
Community: Amblebrook
Sagebrook 880 SHADOWBROOKE DR, DOVER, PA, 17315, Dover, PA 17315
$379,990

2 beds

|

2 baths

880 SHADOWBROOKE DR, DOVER, PA, 17315
Community: Sagebrook
Winding Creek 505 STONE GATE BLVD, ANNVILLE, PA, 17003, Annville, PA 17003
$467,500

2 beds

|

2 baths

|

1,728 sq ft

505 STONE GATE BLVD, ANNVILLE, PA, 17003
Community: Winding Creek
Alden Place 1007 GREAT HALL DR, LEBANON, PA, 17042, Lebanon, PA 17042
$329,900

2 beds

|

2 baths

|

1,948 sq ft

1007 GREAT HALL DR, LEBANON, PA, 17042
Community: Alden Place
Penn National 6352 PENN NATIONAL DR, CHAMBERSBURG, PA,..., Chambersburg, PA 17201
$495,000

3 beds

|

2 baths

|

2,173 sq ft

6352 PENN NATIONAL DR, CHAMBERSBURG, PA,...
Community: Penn National

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544 homes near New Windsor
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