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New Windsor, MD 55+ active adult communities & homes for sale - Page 4

608 homes near New Windsor

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2.3 rating (3 reviews) Leisure World® of Marylan...
<$100k - $800ks
Leisure World® of Marylan..., Silver Spring, MD
Resale Only | 55+ age-restricted | Built 1966 - 2009 | 5,600 homes
Four Seasons at Kent Isla...
$400ks - $700ks
Four Seasons at Kent Isla..., Kent Island, MD
New Construction | 55+ age-restricted | Built 2018 - present | 1,079 homes
4.3 rating (11 reviews) Amblebrook
$300ks - $700ks
Amblebrook, Gettysburg, PA
New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes
The Flats at Heathcote Vi...
$300ks - $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction | 55+ age-restricted | Built 2026 - present | 500 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
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Winding Creek
$300ks - $700ks
Winding Creek, Palmyra, PA
New Construction | 55+ age-restricted | Built 2021 - present | 82 homes
The Village at Cabin Bran...
$500ks
The Village at Cabin Bran..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2021 - present
Element at Mill Creek
$400ks - $600ks
Element at Mill Creek, Annapolis, MD
New Construction | 55+ age-restricted | Built 2022 - present | 140 homes
Penn National
$100ks - $600ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 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.
Cameron Grove
$200ks - $400ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 homes
5 rating (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
The Flats at Northside
$600ks - $1Ms
The Flats at Northside, Potomac, MD
New Construction | Age-targeted | Built 2025 - present | 143 homes
Traditions of America at ...
$400ks - $600ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 homes
5 rating (1 reviews) Two Rivers
$500ks - $700ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
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
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
The Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
Bay Bridge Cove
$300ks - $500ks
Bay Bridge Cove, Stevensville, MD
Resale Only | 55+ age-restricted | Built 2016 - 2022 | 273 homes
5 rating (1 reviews) Snowden Overlook
$300ks - $600ks
Snowden Overlook, Columbia, MD
Resale Only | 55+ age-restricted | Built 2005 - 2010 | 350 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 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.
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 homes
5 rating (1 reviews) Regency at Dominion Valle...
$300ks - $1Ms
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, MD
New Construction | 55+ age-restricted | Built 2026 - present
Beechfield Manors
$200ks - $400ks
Beechfield Manors, Bowie, MD
New Construction | 55+ age-restricted | Built 2024 - present
Spring Valley Estates
$300ks - $400ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
Signature Club at Greenvi...
$400ks - $500ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Tanyard Shores
$400ks - $500ks
Tanyard Shores, Glen Burnie, MD
New Construction | 55+ age-restricted | Built 2020 - present | 190 homes
Gerst Farm
$500ks - $700ks
Gerst Farm, Perry Hall, MD
New Construction | 55+ age-restricted | Built 2026 - present | 202 homes
5 rating (1 reviews) Alden Place
$300ks - $600ks
Alden Place, Lebanon, PA
New and Resale | 55+ age-restricted | Built 2009 - present | 505 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.
Montebello
$500ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
3 rating (2 reviews) Dunbarton
$300ks - $500ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
Legacy at Gateway
$300ks
Legacy at Gateway, Bel Air, MD
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 70 homes
Cromwell 55+
$300ks - $900ks
Cromwell 55+, Ijamsville, MD
New Construction | 55+ age-restricted | Built 2024 - present | 488 homes
Four Seasons at Virginia ...
$400ks - $500ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 homes
Briar Lake
$300ks - $400ks
Briar Lake, Lebanon, PA
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 113 homes
Carroll's Creek
$300ks
Carroll's Creek, Gambrills, MD
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 162 homes
Cadence at Lansdowne
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Legacy at Fallston Common...
$500ks
Legacy at Fallston Common..., Fallston, MD
Resale Only | 55+ age-restricted | Built 2011 - 2018 | 187 homes
Sagebrook
$300ks - $400ks
Sagebrook, Dover, PA
New and Resale | 55+ age-restricted | Built 2020 - present | 194 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.
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Crestwood Village 7079 CATALPA RD, FREDERICK, MD, 21703, Frederick, MD 21703
$360,000

2 beds

|

2 baths

|

1,232 sq ft

7079 CATALPA RD, FREDERICK, MD, 21703
Community: Crestwood Village
Four Seasons at Kent Island 169 HARRIER WAY, CHESTER, MD, 21619, Chester, MD 21619
$779,900

2 beds

|

2 baths

|

2,394 sq ft

169 HARRIER WAY, CHESTER, MD, 21619
Central Parke at Victoria Falls 13851 BELLE CHASSE BLVD 213, LAUREL, MD,..., Laurel, MD 20707
$395,000

3 beds

|

2 baths

|

1,703 sq ft

|

Condo

13851 BELLE CHASSE BLVD 213, LAUREL, MD,...
Four Seasons at Kent Island 110 BOATSWAIN WAY 3042, CHESTER, MD, 216..., Chester, MD 21619
$749,990

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

110 BOATSWAIN WAY 3042, CHESTER, MD, 216...
Four Seasons at Kent Island 540 WARBLER WAY, CHESTER, MD, 21619, Chester, MD 21619
$929,990

3 beds

|

3 baths

|

2,789 sq ft

540 WARBLER WAY, CHESTER, MD, 21619
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Emerald Pointe 19419 AMETHYST DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$425,000

2 beds

|

2 baths

|

2,394 sq ft

19419 AMETHYST DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Amblebrook 182 RUSTIC WOOD DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$599,900

2 beds

|

2 baths

|

2,154 sq ft

182 RUSTIC WOOD DR, GETTYSBURG, PA, 1732...
Community: Amblebrook
Crestwood Village 5603 HONEYSUCKLE CT, FREDERICK, MD, 2170..., Frederick, MD 21703
$412,000

2 beds

|

1 baths

|

1,297 sq ft

5603 HONEYSUCKLE CT, FREDERICK, MD, 2170...
Community: Crestwood Village
The Crossings at Sweetbriar 928 SWEETBAY LN, LEBANON, PA, 17046, Lebanon, PA 17046
$415,000

2 beds

|

2 baths

|

1,708 sq ft

928 SWEETBAY LN, LEBANON, PA, 17046
Central Parke at Victoria Falls 7300 COLCHIS CT, LAUREL, MD, 20707, Laurel, MD 20707
$634,900

3 beds

|

3 baths

|

2,800 sq ft

7300 COLCHIS CT, LAUREL, MD, 20707
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.
Montebello 21630 HAWKSBILL HIGH CIR 204, STERLING, ..., Sterling, VA 20164
$577,590

2 beds

|

2 baths

|

1,640 sq ft

|

Condo

21630 HAWKSBILL HIGH CIR 204, STERLING, ...
Community: Montebello
Leisure World® of Maryland 3576 CHISWICK CT 34-2C, SILVER SPRING, M..., Silver Spring, MD 20906
$180,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

3576 CHISWICK CT 34-2C, SILVER SPRING, M...
Four Seasons at Kent Island 121 MERLIN DR, CHESTER, MD, 21619, Chester, MD 21619
$719,900

2 beds

|

2 baths

|

2,118 sq ft

121 MERLIN DR, CHESTER, MD, 21619
Leisure World® of Maryland 15107 INTERLACHEN DR 2-115, SILVER SPRIN..., Silver Spring, MD 20906
$235,000

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

15107 INTERLACHEN DR 2-115, SILVER SPRIN...
Potomac Green 20515 LITTLE CREEK TER 101, ASHBURN, VA,..., Ashburn, VA 20147
$429,900

2 beds

|

2 baths

|

1,347 sq ft

|

Condo

20515 LITTLE CREEK TER 101, ASHBURN, VA,...
Community: Potomac Green
Leisure World® of Maryland 2900 N LEISURE WORLD BLVD 211, SILVER SP..., Silver Spring, MD 20906
$329,000

2 beds

|

2 baths

|

1,466 sq ft

|

Condo

2900 N LEISURE WORLD BLVD 211, SILVER SP...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 3330 GLENEAGLES DR 68-2D, SILVER SPRING,..., Silver Spring, MD 20906
$165,000

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

3330 GLENEAGLES DR 68-2D, SILVER SPRING,...
Regency at Dominion Valley 5416 ZOYSIA CT, HAYMARKET, VA, 20169, Haymarket, VA 20169
$850,000

4 beds

|

4 baths

|

3,962 sq ft

5416 ZOYSIA CT, HAYMARKET, VA, 20169
Leisure World® of Maryland 3466 CHISWICK CT 43-2A, SILVER SPRING, M..., Silver Spring, MD 20906
$175,000

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

3466 CHISWICK CT 43-2A, SILVER SPRING, M...
Amblebrook 117 GENTLE SLOPE WAY, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$551,990

4 beds

|

4 baths

|

1,574 sq ft

117 GENTLE SLOPE WAY, GETTYSBURG, PA, 17...
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.
Leisure World® of Maryland 3210 N LEISURE WORLD BLVD 1014, SILVER S..., Silver Spring, MD 20906
$325,000

2 beds

|

2 baths

|

1,090 sq ft

|

Condo

3210 N LEISURE WORLD BLVD 1014, SILVER S...
Two Rivers 3020 TURNSTILE LN, ODENTON, MD, 21113, Odenton, MD 21113
$865,000

3 beds

|

4 baths

|

4,086 sq ft

3020 TURNSTILE LN, ODENTON, MD, 21113
Community: Two Rivers
Brookshire 726 HEATHER RDG, MANHEIM, PA, 17545, Manheim, PA 17545
$360,000

3 beds

|

3 baths

|

1,428 sq ft

726 HEATHER RDG, MANHEIM, PA, 17545
Community: Brookshire
Cromwell 55+ 6144 BECK OVERLOOK, IJAMSVILLE, MD, 2175..., Ijamsville, MD 21754
$699,990

2 beds

|

2 baths

|

3,387 sq ft

6144 BECK OVERLOOK, IJAMSVILLE, MD, 2175...
Community: Cromwell 55+
Central Parke at Victoria Falls 7208 PAPERBARK TER, LAUREL, MD, 20707, Laurel, MD 20707
$425,000

2 beds

|

2 baths

|

1,502 sq ft

7208 PAPERBARK TER, LAUREL, MD, 20707
The Flats at Northside 1135 POLARIS RD 90, POTOMAC, MD, 20854, Potomac, MD 20854
$1,642,700

3 beds

|

5 baths

|

3,470 sq ft

1135 POLARIS RD 90, POTOMAC, MD, 20854
The Flats at Northside 1135 POLARIS RD 75, POTOMAC, MD, 20854, Potomac, MD 20854
$1,424,100

4 beds

|

3 baths

|

2,840 sq ft

1135 POLARIS RD 75, POTOMAC, MD, 20854
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
The Flats at Northside 1135 POLARIS RD 101, POTOMAC, MD, 20854, Potomac, MD 20854
$1,698,975

4 beds

|

5 baths

|

3,470 sq ft

1135 POLARIS RD 101, POTOMAC, MD, 20854
The Enclave at Ellicott Hills 2649 BUCKINGHAM RD 43, ELLICOTT CITY, MD..., Ellicott City, MD 21043
$739,900

3 beds

|

4 baths

|

3,688 sq ft

|

Condo

2649 BUCKINGHAM RD 43, ELLICOTT CITY, MD...
Heritage Hunt 13886 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$924,900

3 beds

|

4 baths

|

3,590 sq ft

13886 CRABTREE WAY, GAINESVILLE, VA, 201...
Community: Heritage Hunt
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 Ellicott Mills 3011 DEXTER DR 1106, ELLICOTT CITY, MD, ..., Ellicott City, MD 21043
$375,000

2 beds

|

1 baths

|

980 sq ft

|

Condo

3011 DEXTER DR 1106, ELLICOTT CITY, MD, ...
Liberty Grove 8600 LIBERTY TRL 306, MANASSAS, VA, 2011..., Manassas, VA 20110
$330,000

2 beds

|

3 baths

|

1,743 sq ft

|

Condo

8600 LIBERTY TRL 306, MANASSAS, VA, 2011...
Community: Liberty Grove
Crestwood Village 7058 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703
$185,000
|

1 baths

|

617 sq ft

7058 BASSWOOD RD, FREDERICK, MD, 21703
Community: Crestwood Village
Bloomfields 55+ 2605 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702
$785,000

3 beds

|

4 baths

|

3,462 sq ft

2605 BROADLEAF DR, FREDERICK, MD, 21702
Community: Bloomfields 55+
Potomac Green 20515 LITTLE CREEK TER 304, ASHBURN, VA,..., Ashburn, VA 20147
$535,000

2 beds

|

2 baths

|

1,515 sq ft

|

Condo

20515 LITTLE CREEK TER 304, ASHBURN, VA,...
Community: Potomac Green
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 203, HAYMARKET, VA, 2..., Haymarket, VA 20169
$515,005

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

5800 MOONSTONE WAY 203, HAYMARKET, VA, 2...
Walhaven at Kingstowne 5951 CLAPTON CT, ALEXANDRIA, VA, 22310, Alexandria, VA 22310
$899,000

3 beds

|

4 baths

|

2,804 sq ft

|

Condo

5951 CLAPTON CT, ALEXANDRIA, VA, 22310
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 202, HAYMARKET, VA, 2..., Haymarket, VA 20169
$627,140

3 beds

|

2 baths

|

1,850 sq ft

|

Condo

5800 MOONSTONE WAY 202, HAYMARKET, VA, 2...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 104, HAYMARKET, VA, 2..., Haymarket, VA 20169
$456,065

2 beds

|

2 baths

|

1,345 sq ft

|

Condo

5800 MOONSTONE WAY 104, HAYMARKET, VA, 2...
The Flats at Heathcote Village by Del Webb 6156 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$699,990

3 beds

|

3 baths

|

2,625 sq ft

6156 AMBER LN, HAYMARKET, VA, 20169
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.

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