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New Windsor, MD 55+ active adult communities & homes for sale - Page 3

626 homes near New Windsor

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5 rating (1 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
Cameron Grove
$200ks - $400ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 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 Flats at Northside
$600ks - $1Ms
The Flats at Northside, Potomac, MD
New Construction | Age-targeted | Built 2025 - present | 143 homes
3.7 rating (3 reviews) Heritage Harbour
$300ks - $800ks
Heritage Harbour, Annapolis, MD
Resale Only | 55+ age-restricted | Built 1979 - 2008 | 1,683 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
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.
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
Beechfield Manors
$200ks - $400ks
Beechfield Manors, Bowie, MD
New Construction | 55+ age-restricted | Built 2024 - present
Element at Mill Creek
$400ks - $600ks
Element at Mill Creek, Annapolis, MD
New Construction | 55+ age-restricted | Built 2022 - present | 140 homes
The Village at Cabin Bran...
$500ks
The Village at Cabin Bran..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2021 - present
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Questions? Call us: (443) 647-4690
5 rating (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 homes
5 rating (1 reviews) Alden Place
$300ks - $500ks
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.
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, MD
New Construction | 55+ age-restricted | Built 2026 - present
5 rating (2 reviews) Arbor Gate
$200ks
Arbor Gate, Myerstown, PA
Resale Only | 55+ age-restricted | Built 1997 - 2005 | 378 homes
The Atrium at MetroWest
$600ks - $700ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 homes
The Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Penn National
$100ks - $600ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
Four Seasons at Virginia ...
$400ks - $500ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 homes
5 rating (1 reviews) Gatherings at Wellington
$300ks - $400ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 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.
Bay Bridge Cove
$300ks - $500ks
Bay Bridge Cove, Stevensville, MD
Resale Only | 55+ age-restricted | Built 2016 - 2022 | 273 homes
5 rating (2 reviews) Central Parke at Victoria...
$300ks - $500ks
Central Parke at Victoria..., Laurel, MD
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes
Tanyard Shores
$400ks - $500ks
Tanyard Shores, Glen Burnie, MD
New Construction | 55+ age-restricted | Built 2020 - present | 190 homes
Legacy at Fallston Common...
$500ks
Legacy at Fallston Common..., Fallston, MD
Resale Only | 55+ age-restricted | Built 2011 - 2018 | 187 homes
5 rating (1 reviews) Gatherings at Lyndwood
$300ks - $400ks
Gatherings at Lyndwood, Elkridge, MD
Resale Only | 55+ age-restricted | Built 2005 - 2008 | 216 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Winifred Manor
$200ks
Winifred Manor, Eldersburg, MD
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 152 homes
5 rating (1 reviews) Carroll Vista
$300ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 homes
The Village at Freedom Hi...
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
Traditions of America at ...
$400ks - $600ks
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.
Cedar Ridge at Piney Orch...
$200ks - $300ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
Carroll's Creek
$300ks
Carroll's Creek, Gambrills, MD
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 162 homes
Blue Ridge
$300ks - $400ks
Blue Ridge, Harrisburg, PA
New and Resale | Age-targeted | Built 2020 - present | 130 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
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
123...4
Leisure World® of Maryland 15115 INTERLACHEN DR 3-204, SILVER SPRIN..., Silver Spring, MD 20906
$285,000

2 beds

|

2 baths

|

1,480 sq ft

|

Condo

15115 INTERLACHEN DR 3-204, SILVER SPRIN...
Heritage Harbour 906 PERRY LANDING CT, ANNAPOLIS, MD, 214..., Annapolis, MD 21401
$609,900

2 beds

|

3 baths

|

2,569 sq ft

906 PERRY LANDING CT, ANNAPOLIS, MD, 214...
Community: Heritage Harbour
Leisure World® of Maryland 2900 N LEISURE WORLD BLVD 212, SILVER SP..., Silver Spring, MD 20906
$179,000

1 beds

|

1 baths

|

896 sq ft

|

Condo

2900 N LEISURE WORLD BLVD 212, SILVER SP...
Arbor Gate 19 SPRINGHOUSE DR, MYERSTOWN, PA, 17067, Myerstown, PA 17067
$239,000

3 beds

|

2 baths

|

1,319 sq ft

19 SPRINGHOUSE DR, MYERSTOWN, PA, 17067
Community: Arbor Gate
Emerald Pointe 19553 TURQUOISE DR V222, HAGERSTOWN, MD,..., Hagerstown, MD 21742
$484,900

2 beds

|

2 baths

|

1,850 sq ft

19553 TURQUOISE DR V222, HAGERSTOWN, MD,...
Community: Emerald Pointe
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 3712 FINSBURY PARK DR 50-A, SILVER SPRIN..., Silver Spring, MD 20906
$389,900

2 beds

|

2 baths

|

1,157 sq ft

3712 FINSBURY PARK DR 50-A, SILVER SPRIN...
Heritage Harbour 860 WOODMONT RD, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$629,000

3 beds

|

2 baths

|

1,623 sq ft

860 WOODMONT RD, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Leisure World® of Maryland 3700 GLEN EAGLES DR, SILVER SPRING, MD, ..., Silver Spring, MD 20906
$775,000

4 beds

|

3 baths

|

3,776 sq ft

3700 GLEN EAGLES DR, SILVER SPRING, MD, ...
Carroll Vista 154 SADDLETOP DR 355, TANEYTOWN, MD, 217..., Taneytown, MD 21787
$330,000

2 beds

|

2 baths

|

1,394 sq ft

|

Condo

154 SADDLETOP DR 355, TANEYTOWN, MD, 217...
Community: Carroll Vista
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.
Briar Lake 858 WATER EDGE CT, LEBANON, PA, 17046, Lebanon, PA 17046
$429,000

3 beds

|

2 baths

|

1,700 sq ft

858 WATER EDGE CT, LEBANON, PA, 17046
Community: Briar Lake
Four Seasons at Kent Island 102 BOATSWAIN WAY 2934, CHESTER, MD, 216..., Chester, MD 21619
$989,990

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

102 BOATSWAIN WAY 2934, CHESTER, MD, 216...
Four Seasons at Kent Island 102 BOATSWAIN WAY 2921, CHESTER, MD, 216..., Chester, MD 21619
$889,990

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

102 BOATSWAIN WAY 2921, CHESTER, MD, 216...
Four Seasons at Kent Island 102 BOATSWAIN WAY 2912, CHESTER, MD, 216..., Chester, MD 21619
$649,990

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

102 BOATSWAIN WAY 2912, CHESTER, MD, 216...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Four Seasons at Kent Island 102 BOATSWAIN WAY 2911, CHESTER, MD, 216..., Chester, MD 21619
$649,990

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

102 BOATSWAIN WAY 2911, CHESTER, MD, 216...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 422, LEESBURG, V..., Leesburg, VA 20176
$370,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19355 CYPRESS RIDGE TER 422, LEESBURG, V...
Tanyard Shores 7414 AMEGA WAY, GLEN BURNIE, MD, 21060, Glen Burnie, MD 21060
$536,890

3 beds

|

4 baths

|

2,237 sq ft

7414 AMEGA WAY, GLEN BURNIE, MD, 21060
Community: Tanyard Shores
Potomac Green 20500 CASABLANCA DR, ASHBURN, VA, 20147, Ashburn, VA 20147
$739,000

3 beds

|

3 baths

|

2,447 sq ft

20500 CASABLANCA DR, ASHBURN, VA, 20147
Community: Potomac Green
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 169 HARRIER WAY, CHESTER, MD, 21619, Chester, MD 21619
$779,900

3 beds

|

2 baths

|

2,394 sq ft

169 HARRIER WAY, CHESTER, MD, 21619
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 409, LEESBURG, V..., Leesburg, VA 20176
$289,000

1 beds

|

1 baths

|

874 sq ft

|

Condo

19375 CYPRESS RIDGE TER 409, LEESBURG, V...
Leisure World® of Maryland 3330 N LEISURE WORLD BLVD 5-627, SILVER ..., Silver Spring, MD 20906
$270,000

2 beds

|

2 baths

|

1,138 sq ft

|

Condo

3330 N LEISURE WORLD BLVD 5-627, SILVER ...
Cameron Grove 13220 FOX BOW DR 307, UPPER MARLBORO, MD..., Upper Marlboro, MD 20774
$330,000

2 beds

|

2 baths

|

1,187 sq ft

|

Condo

13220 FOX BOW DR 307, UPPER MARLBORO, MD...
Community: Cameron Grove
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Heritage Hunt 6230 SETTLERS TRAIL PL, GAINESVILLE, VA,..., Gainesville, VA 20155
$738,000

4 beds

|

3 baths

|

3,082 sq ft

6230 SETTLERS TRAIL PL, GAINESVILLE, VA,...
Community: Heritage Hunt
Potomac Green 44367 ADARE MANOR SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$675,000

2 beds

|

3 baths

|

2,060 sq ft

44367 ADARE MANOR SQ, ASHBURN, VA, 20147
Community: Potomac Green
Signature Club at Greenview 10832 DEWEY WAY, NEW MARKET, MD, 21774, New Market, MD 21774
$475,000

4 beds

|

4 baths

|

2,424 sq ft

10832 DEWEY WAY, NEW MARKET, MD, 21774
Dunbarton 9709 SEAFIELD PL, BRISTOW, VA, 20136, Bristow, VA 20136
$750,000

4 beds

|

4 baths

|

4,435 sq ft

9709 SEAFIELD PL, BRISTOW, VA, 20136
Community: Dunbarton
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.
Heritage Harbour 1011 BOOM CT, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$559,900

3 beds

|

4 baths

|

2,640 sq ft

1011 BOOM CT, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Leisure World® of Maryland 3108 BECKENHAM CT 251-H, SILVER SPRING, ..., Silver Spring, MD 20906
$245,000

2 beds

|

3 baths

|

1,385 sq ft

|

Condo

3108 BECKENHAM CT 251-H, SILVER SPRING, ...
Birchwood at Brambleton 42970 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$882,206

3 beds

|

4 baths

|

2,742 sq ft

42970 TRUMAN TER, ASHBURN, VA, 20148
Heritage Harbour 969 RUNNING BROOK WAY, ANNAPOLIS, MD, 21..., Annapolis, MD 21401
$739,000

3 beds

|

2 baths

|

2,621 sq ft

969 RUNNING BROOK WAY, ANNAPOLIS, MD, 21...
Community: Heritage Harbour
Gatherings at Lyndwood 6150 SHADYWOOD RD 207, ELKRIDGE, MD, 210..., Elkridge, MD 21075
$485,000

3 beds

|

2 baths

|

1,900 sq ft

|

Condo

6150 SHADYWOOD RD 207, ELKRIDGE, MD, 210...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Crestwood Village 5661 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703
$435,000

2 beds

|

2 baths

|

1,297 sq ft

5661 CRABAPPLE DR, FREDERICK, MD, 21703
Community: Crestwood Village
The Aspens 592 N 16TH ST, LEBANON, PA, 17046, Lebanon, PA 17046
$258,000

2 beds

|

2 baths

|

1,312 sq ft

592 N 16TH ST, LEBANON, PA, 17046
Community: The Aspens
Ellicott's Retreat 8580 SUNELL LN, ELLICOTT CITY, MD, 21043, Ellicott City, MD 21043
$1,299,000

6 beds

|

7 baths

|

4,241 sq ft

8580 SUNELL LN, ELLICOTT CITY, MD, 21043
Community: Ellicott's Retreat
Central Parke at Victoria Falls 7201 PAPERBARK TER, LAUREL, MD, 20707, Laurel, MD 20707
$419,000

2 beds

|

2 baths

|

1,464 sq ft

7201 PAPERBARK TER, 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.
The Flats at Heathcote Village by Del Webb 6091 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$782,540

3 beds

|

3 baths

|

2,625 sq ft

6091 AZURITE WAY, HAYMARKET, VA, 20169
Four Seasons at Kent Island 249 WARBLER WAY, CHESTER, MD, 21619, Chester, MD 21619
$699,000

2 beds

|

2 baths

|

2,025 sq ft

249 WARBLER WAY, CHESTER, MD, 21619
The Flats at Heathcote Village by Del Webb 6093 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$820,756

3 beds

|

4 baths

|

2,625 sq ft

6093 AZURITE WAY, HAYMARKET, VA, 20169
The Flats at Heathcote Village by Del Webb 6099 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$737,083

3 beds

|

3 baths

|

2,763 sq ft

6099 AZURITE WAY, HAYMARKET, VA, 20169
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 5917 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$841,207

4 beds

|

4 baths

|

4,034 sq ft

5917 SUNSTONE LN, HAYMARKET, VA, 20169
Heritage Harbour 911 YARDARM LN, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$515,000

2 beds

|

2 baths

|

1,514 sq ft

911 YARDARM LN, ANNAPOLIS, MD, 21401
Community: Heritage Harbour

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