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

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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The Flats at Northside 1121 FORTUNE TER 410, POTOMAC, MD, 20854, Potomac, MD 20854
$903,709

2 beds

|

2 baths

|

1,534 sq ft

|

Condo

1121 FORTUNE TER 410, POTOMAC, MD, 20854
The Flats at Northside 1121 FORTUNE TER 404, POTOMAC, MD, 20854, Potomac, MD 20854
$863,234

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

1121 FORTUNE TER 404, POTOMAC, MD, 20854
Heritage Harbour 2900 SHIPMASTER WAY 309, ANNAPOLIS, MD, ..., Annapolis, MD 21401
$325,000

2 beds

|

2 baths

|

1,136 sq ft

|

Condo

2900 SHIPMASTER WAY 309, ANNAPOLIS, MD, ...
Community: Heritage Harbour
Lansdowne Woods of Virginia 19370 MAGNOLIA GROVE SQ L04, LEESBURG, V..., Leesburg, VA 20176
$594,900

2 beds

|

2 baths

|

1,708 sq ft

|

Condo

19370 MAGNOLIA GROVE SQ L04, LEESBURG, V...
Two Rivers 2446 HEATH ASTER CT, ODENTON, MD, 21113, Odenton, MD 21113
$799,000

4 beds

|

3 baths

|

1,802 sq ft

2446 HEATH ASTER CT, ODENTON, MD, 21113
Community: Two Rivers
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
JerMae Estates 5 GEOLEY CT, THURMONT, MD, 21788, Thurmont, MD 21788
$476,000

4 beds

|

3 baths

|

2,038 sq ft

5 GEOLEY CT, THURMONT, MD, 21788
Community: JerMae Estates
Four Seasons at Elm Tree 707 THOREAU DR, MOUNT JOY, PA, 17552, Mount Joy, PA 17552
$530,000

3 beds

|

2 baths

|

2,296 sq ft

707 THOREAU DR, MOUNT JOY, PA, 17552
Leisure World® of Maryland 3100 N LEISURE WORLD BLVD 207, SILVER SP..., Silver Spring, MD 20906
$559,000

3 beds

|

3 baths

|

1,735 sq ft

|

Condo

3100 N LEISURE WORLD BLVD 207, SILVER SP...
Leisure World® of Maryland 14805 PENNFIELD CIR 206, SILVER SPRING, ..., Silver Spring, MD 20906
$360,000

2 beds

|

2 baths

|

1,288 sq ft

|

Condo

14805 PENNFIELD CIR 206, SILVER SPRING, ...
The Village at Cabin Branch 13210 PETREL ST 3307, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$659,000

3 beds

|

2 baths

|

2,031 sq ft

|

Condo

13210 PETREL ST 3307, CLARKSBURG, MD, 20...
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 Cabin Branch 13210 PETREL ST 3307, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$659,000

3 beds

|

2 baths

|

2,031 sq ft

|

Condo

13210 PETREL ST 3307, CLARKSBURG, MD, 20...
Leisure World® of Maryland 3210 N LEISURE WORLD BLVD 116, SILVER SP..., Silver Spring, MD 20906
$369,000

2 beds

|

2 baths

|

1,505 sq ft

|

Condo

3210 N LEISURE WORLD BLVD 116, SILVER SP...
Heritage Harbour 903 SCUPPER CT, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$1,050,000

4 beds

|

5 baths

|

5,766 sq ft

903 SCUPPER CT, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Gerst Farm 9442 GERST RD, PERRY HALL, MD, 21128, Perry Hall, MD 21128
$499,990

3 beds

|

3 baths

|

2,690 sq ft

9442 GERST RD, PERRY HALL, MD, 21128
Community: Gerst Farm
Tanyard Shores 900 SANKOFA RD, GLEN BURNIE, MD, 21060, Glen Burnie, MD 21060
$559,900

4 beds

|

4 baths

|

3,556 sq ft

900 SANKOFA RD, GLEN BURNIE, MD, 21060
Community: Tanyard Shores
Leisure World® of Maryland 3632 GLENEAGLES DR 8-1F, SILVER SPRING, ..., Silver Spring, MD 20906
$105,000

1 beds

|

1 baths

|

635 sq ft

|

Condo

3632 GLENEAGLES DR 8-1F, SILVER SPRING, ...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Penn National 7132 LONE RIDGE CT, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$487,700

3 beds

|

4 baths

|

3,496 sq ft

7132 LONE RIDGE CT, FAYETTEVILLE, PA, 17...
Community: Penn National
Saintsbury Plaza 2901 SAINTSBURY PLZ 206, FAIRFAX, VA, 22..., Fairfax, VA 22031
$469,500

2 beds

|

2 baths

|

1,325 sq ft

|

Condo

2901 SAINTSBURY PLZ 206, FAIRFAX, VA, 22...
Community: Saintsbury Plaza
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 111, SILVER SP..., Silver Spring, MD 20906
$200,000

2 beds

|

2 baths

|

1,035 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 111, SILVER SP...
The Crest of Alexandria 7753 BELVALE DR, ALEXANDRIA, VA, 22315, Alexandria, VA 22315
$955,000

4 beds

|

4 baths

|

3,205 sq ft

7753 BELVALE DR, ALEXANDRIA, VA, 22315
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.
Spring Hill 8970 FASCINATION CT 130, LORTON, VA, 220..., Lorton, VA 22079
$339,000

2 beds

|

2 baths

|

890 sq ft

|

Condo

8970 FASCINATION CT 130, LORTON, VA, 220...
Community: Spring Hill
Four Seasons at Kent Island 110 BOATSWAIN WAY 3044, CHESTER, MD, 216..., Chester, MD 21619
$999,990

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

110 BOATSWAIN WAY 3044, CHESTER, MD, 216...
Four Seasons at Kent Island 102 BOATSWAIN WAY 2911, CHESTER, MD, 216..., Chester, MD 21619
$629,990

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

102 BOATSWAIN WAY 2911, CHESTER, MD, 216...
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 719, LEESBURG, V..., Leesburg, VA 20176
$383,250

2 beds

|

2 baths

|

1,101 sq ft

|

Condo

19375 CYPRESS RIDGE TER 719, LEESBURG, V...
Penn National 6804 LYTHAM LN, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222
$639,000

4 beds

|

4 baths

|

3,053 sq ft

6804 LYTHAM LN, FAYETTEVILLE, PA, 17222
Community: Penn National
Four Seasons at Kent Island 323 KINGFISHER LN, CHESTER, MD, 21619, Chester, MD 21619
$974,990

5 beds

|

5 baths

|

3,225 sq ft

323 KINGFISHER LN, CHESTER, MD, 21619
Birchwood at Brambleton 23664 JAYADEV TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$779,950

3 beds

|

3 baths

|

2,406 sq ft

23664 JAYADEV TER, ASHBURN, VA, 20148
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Cedar Ridge at Piney Orchard 8612 FLUTTERING LEAF TRL 208, ODENTON, M..., Odenton, MD 21113
$350,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

8612 FLUTTERING LEAF TRL 208, ODENTON, M...
Bay Bridge Cove 222 MOORINGS CIR 126, STEVENSVILLE, MD, ..., Stevensville, MD 21666
$600,000

3 beds

|

3 baths

|

2,074 sq ft

|

Condo

222 MOORINGS CIR 126, STEVENSVILLE, MD, ...
Community: Bay Bridge Cove
The Aspens 602 MULBERRY LN, LEBANON, PA, 17046, Lebanon, PA 17046
$290,000

2 beds

|

2 baths

|

1,272 sq ft

602 MULBERRY LN, LEBANON, PA, 17046
Community: The Aspens
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 Village at Cabin Branch 13220 PETREL ST 4202, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$615,000

3 beds

|

2 baths

|

Condo

13220 PETREL ST 4202, CLARKSBURG, MD, 20...
Gatherings at Cabin Branch 13220 PETREL ST 4202, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$615,000

3 beds

|

2 baths

|

Condo

13220 PETREL ST 4202, CLARKSBURG, MD, 20...
Two Rivers 2864 SOFT RUSH WAY, ODENTON, MD, 21113, Odenton, MD 21113
$889,000

5 beds

|

4 baths

|

3,645 sq ft

2864 SOFT RUSH WAY, ODENTON, MD, 21113
Community: Two Rivers
Emerald Hills 1603 MARTHA CT 402, BEL AIR, MD, 21015, Bel Air, MD 21015
$279,900

2 beds

|

2 baths

|

1,320 sq ft

|

Condo

1603 MARTHA CT 402, BEL AIR, MD, 21015
Community: Emerald Hills
Four Seasons at Kent Island 715 WARBLER WAY, CHESTER, MD, 21619, Chester, MD 21619
$839,990

4 beds

|

3 baths

|

2,791 sq ft

715 WARBLER WAY, CHESTER, MD, 21619
Four Seasons at Kent Island 723 WARBLER WAY, CHESTER, MD, 21619, Chester, MD 21619
$789,990

4 beds

|

3 baths

|

2,791 sq ft

723 WARBLER WAY, CHESTER, MD, 21619
Four Seasons at Kent Island 532 WARBLER WAY, CHESTER, MD, 21619, Chester, MD 21619
$929,990

3 beds

|

3 baths

|

2,772 sq ft

532 WARBLER WAY, CHESTER, MD, 21619
Four Seasons at Kent Island 102 BOATSWAIN WAY 2933, CHESTER, MD, 216..., Chester, MD 21619
$829,990

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

102 BOATSWAIN WAY 2933, CHESTER, MD, 216...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
North Pointe Condominiums 623 NORTHLAND DR 67, HANOVER, PA, 17331, Hanover, PA 17331
$300,000

2 beds

|

2 baths

|

1,332 sq ft

|

Condo

623 NORTHLAND DR 67, HANOVER, PA, 17331
Emerald Hills 1604 MARTHA CT 101, BEL AIR, MD, 21015, Bel Air, MD 21015
$274,999

2 beds

|

2 baths

|

1,240 sq ft

|

Condo

1604 MARTHA CT 101, BEL AIR, MD, 21015
Community: Emerald Hills
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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This application does not include information on all of the properties available for sale at this time.

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