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New Windsor, MD 55+ active adult communities & homes for sale - Page 2

162 communities near New Windsor

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The Enclave at Ellicott S...
$400ks - $500ks
The Enclave at Ellicott S..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 69 homes
The Crest of Alexandria
$400ks - $800ks
The Crest of Alexandria, Alexandria, VA
New and Resale | 55+ age-restricted | Built 2017 - present | 250 homes
Sagebrook
$300ks - $400ks
Sagebrook, Dover, PA
New and Resale | 55+ age-restricted | Built 2020 - present | 194 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
Emerald Hills
$200ks
Emerald Hills, Bel Air, MD
Resale Only | 55+ age-restricted | Built 2006 - 2019 | 240 homes
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The Courtyards at Waverly...
$300ks - $1Ms
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 homes
The Atrium at MetroWest
$600ks - $700ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 homes
Legacy at Fallston Common...
$500ks
Legacy at Fallston Common..., Fallston, MD
Resale Only | 55+ age-restricted | Built 2011 - 2018 | 187 homes
Courtyards at Waverly Woo...
$300ks - $600ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 383 homes
5 rating (1 reviews) Crestwood Village
$200ks - $500ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 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.
Creek View
$200ks
Creek View, Carlisle, PA
New and Resale | 55+ age-restricted | Built 2004 - present | 305 homes
Heritage Run
$200ks - $400ks
Heritage Run, Lebanon, PA
New and Resale | 55+ age-restricted | Built 2006 - present | 88 homes
Ballenger Run
$300ks - $400ks
Ballenger Run, Frederick, MD
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes
Wynfield at Millersville
$300ks - $500ks
Wynfield at Millersville, Millersville, PA
New Construction | 55+ age-restricted | Built 2023 - present | 31 homes
Cedar Ridge at Piney Orch...
$200ks - $300ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
Regency at Belmont
$600ks - $900ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
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Questions? Call us: (443) 647-4690
Bethany Glen
- $600ks
Bethany Glen, Ellicott City, MD
New Construction | 55+ age-restricted | Built 2024 - present | 116 homes
North Pointe Condominiums
$200ks - $300ks
North Pointe Condominiums, Hanover, PA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 120 homes
The Paddock at Equine Mea...
$200ks - $400ks
The Paddock at Equine Mea..., Red Lion, PA
New and Resale | 55+ age-restricted | Built 2016 - present | 174 homes
Meadowview Village
$200ks - $300ks
Meadowview Village, Harrisburg, PA
Resale Only | 55+ age-restricted | Built 2002 - 2016 | 108 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.
Brookshire
$200ks - $400ks
Brookshire, Manheim, PA
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 230 homes
Spring Hill
$400ks - $600ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
4 rating (2 reviews) Traditions of America at ...
$300ks - $600ks
Traditions of America at ..., Lititz, PA
Resale Only | 55+ age-restricted | Built 2013 - 2021 | 329 homes
The Village at Foxfield
$300ks - $500ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
The Preserves at Cumberla...
$200ks - $400ks
The Preserves at Cumberla..., Gettysburg, PA
Resale Only | 55+ age-restricted | Built 2010 - present | 93 homes
5 rating (2 reviews) The Crossings at Sweetbri...
$400ks - $500ks
The Crossings at Sweetbri..., Lebanon, PA
New and Resale | 55+ age-restricted | Built 2012 - present | 198 homes
The Villages At Woodholme
$400ks - $500ks
The Villages At Woodholme, Baltimore, MD
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 286 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
5 rating (2 reviews) Potomac Green
$400ks - $800ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
Gatherings at Ellicott Mi...
$300ks
Gatherings at Ellicott Mi..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2013 - 2018 | 127 homes
Saintsbury Plaza
$300ks - $400ks
Saintsbury Plaza, Fairfax, VA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 111 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.
Crawfords Ridge
$500ks - $600ks
Crawfords Ridge, Odenton, MD
Resale Only | 55+ age-restricted | Built 2006 - 2006 | 27 homes
5 rating (1 reviews) Ellicott's Retreat
$300ks - $400ks
Ellicott's Retreat, Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2017 - 2022 | 160 homes
JerMae Estates
$300ks - $400ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
McKinsey Park
$300ks - $400ks
McKinsey Park, Severna Park, MD
Resale Only | 55+ age-restricted | Built 1993 - 2002 | 89 homes
Enclave at Park Forest
$500ks - $600ks
Enclave at Park Forest, Elkridge, MD
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 45 homes
Watershed
$600ks - $700ks
Watershed, Laurel, MD
New Construction | 55+ age-restricted | 84 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
Wynfield at Annville
$400ks - $600ks
Wynfield at Annville, Annville, PA
New Construction | 55+ age-restricted | Built 2022 - present | 95 homes
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
1 rating (1 reviews) Legacy at Cherry Tree
$400ks - $500ks
Legacy at Cherry Tree, Laurel, MD
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 120 homes
Suffield Meadows
$400ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 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.
New Bent Creek Crossing 2 REDBUD DR, MECHANICSBURG, PA, 17050, Mechanicsburg, PA 17050
$339,000

3 beds

|

3 baths

|

2,300 sq ft

|

Condo

2 REDBUD DR, MECHANICSBURG, PA, 17050
Community: Bent Creek Crossing
Heritage Hunt 7065 HERITAGE HUNT DR 108, GAINESVILLE, ..., Gainesville, VA 20155
$399,900

2 beds

|

2 baths

|

1,292 sq ft

|

Condo

7065 HERITAGE HUNT DR 108, GAINESVILLE, ...
Community: Heritage Hunt
Four Seasons at Kent Island 2000 HERONS NEST WAY 401, CHESTER, MD, 2..., Chester, MD 21619
$700,000

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

2000 HERONS NEST WAY 401, CHESTER, MD, 2...
Four Seasons at Kent Island 132 WHEELHOUSE WAY 11, CHESTER, MD, 2161..., Chester, MD 21619
$700,000

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

132 WHEELHOUSE WAY 11, CHESTER, MD, 2161...
Amblebrook 203 HIGHLAND WAY 3, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$569,990

2 beds

|

2 baths

|

2,130 sq ft

203 HIGHLAND WAY 3, GETTYSBURG, PA, 1732...
Community: Amblebrook
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Amblebrook 192 HIGHLAND WAY 32, GETTYSBURG, PA, 173..., Gettysburg, PA 17325
$539,990

2 beds

|

3 baths

|

2,036 sq ft

192 HIGHLAND WAY 32, GETTYSBURG, PA, 173...
Community: Amblebrook
Amblebrook 328 HIGHLAND WAY 170, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$499,990

2 beds

|

2 baths

|

1,661 sq ft

328 HIGHLAND WAY 170, GETTYSBURG, PA, 17...
Community: Amblebrook
Amblebrook 321 HIGHLAND WAY 160, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$449,900

2 beds

|

2 baths

|

1,409 sq ft

321 HIGHLAND WAY 160, GETTYSBURG, PA, 17...
Community: Amblebrook
New Nells Acres 823 HERMAN WAY, SYKESVILLE, MD, 21784, Sykesville, MD 21784
$585,000

3 beds

|

4 baths

|

2,332 sq ft

823 HERMAN WAY, SYKESVILLE, MD, 21784
Community: Nells Acres
New Creek View 114 GLENRIDGE DR, CARLISLE, PA, 17015, Carlisle, PA 17015
$249,937

2 beds

|

2 baths

|

1,208 sq ft

114 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.
New 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
New Leisure World® of Maryland 2921 N LEISURE WORLD BLVD 1-122, SILVER ..., Silver Spring, MD 20906
$145,000

2 beds

|

2 baths

|

953 sq ft

|

Condo

2921 N LEISURE WORLD BLVD 1-122, SILVER ...
New Heritage Harbour 2900 SHIPMASTER WAY 104, ANNAPOLIS, MD, ..., Annapolis, MD 21401
$349,900

2 beds

|

2 baths

|

1,046 sq ft

|

Condo

2900 SHIPMASTER WAY 104, ANNAPOLIS, MD, ...
Community: Heritage Harbour
New Amblebrook 109 ELDERBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$406,990

3 beds

|

2 baths

|

1,736 sq ft

109 ELDERBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
New Snowden Overlook 8887 WARM GRANITE DR 38, COLUMBIA, MD, 2..., Columbia, MD 21045
$750,000

3 beds

|

5 baths

|

4,208 sq ft

|

Condo

8887 WARM GRANITE DR 38, COLUMBIA, MD, 2...
Community: Snowden Overlook
New Four Seasons at Kent Island 216 KINGFISHER LN, CHESTER, MD, 21619, Chester, MD 21619
$1,400,000

2 beds

|

3 baths

|

2,010 sq ft

216 KINGFISHER LN, CHESTER, MD, 21619
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
New Four Seasons at Kent Island 102 BOATSWAIN WAY 2912, CHESTER, MD, 216..., Chester, MD 21619
$609,990

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

102 BOATSWAIN WAY 2912, CHESTER, MD, 216...
New Penn National 6873 OLD COURSE RD, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$789,000

4 beds

|

4 baths

|

4,605 sq ft

6873 OLD COURSE RD, FAYETTEVILLE, PA, 17...
Community: Penn National
New Leisure World® of Maryland 3330 N LEISURE WORLD BLVD 5-427, SILVER ..., Silver Spring, MD 20906
$260,000

2 beds

|

2 baths

|

1,138 sq ft

|

Condo

3330 N LEISURE WORLD BLVD 5-427, SILVER ...
New Leisure World® of Maryland 2901 S LEISURE WORLD BLVD 401, SILVER SP..., Silver Spring, MD 20906
$515,000

3 beds

|

2 baths

|

1,789 sq ft

|

Condo

2901 S LEISURE WORLD BLVD 401, SILVER SP...
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.
New The Village at Foxfield 4 LAMAR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$475,000

2 beds

|

2 baths

|

1,359 sq ft

4 LAMAR LN, MIDDLETOWN, MD, 21769
New The Village at Foxfield 7 DERR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$625,000

3 beds

|

3 baths

|

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769
New Heritage Run 108 ALLWEIN DR, LEBANON, PA, 17042, Lebanon, PA 17042
$423,900

2 beds

|

2 baths

|

1,577 sq ft

108 ALLWEIN DR, LEBANON, PA, 17042
Community: Heritage Run
New Regency at Dominion Valley 15110 HEATHER MILL LN 307, HAYMARKET, VA..., Haymarket, VA 20169
$439,900

2 beds

|

2 baths

|

1,538 sq ft

|

Condo

15110 HEATHER MILL LN 307, HAYMARKET, VA...
New Leisure World® of Maryland 3330 N LEISURE WORLD BLVD 5-820, SILVER ..., Silver Spring, MD 20906
$178,000

2 beds

|

2 baths

|

980 sq ft

|

Condo

3330 N LEISURE WORLD BLVD 5-820, SILVER ...
New Crestwood Village 5661 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703
$415,000

2 beds

|

2 baths

|

1,297 sq ft

5661 CRABAPPLE DR, FREDERICK, MD, 21703
Community: Crestwood Village
New Gerst Farm 9409 FOUNDERS LN, PERRY HALL, MD, 21128, Perry Hall, MD 21128
$719,990

3 beds

|

3 baths

9409 FOUNDERS LN, PERRY HALL, MD, 21128
Community: Gerst Farm
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
New Gerst Farm 9314 FOUNDERS LN, PERRY HALL, MD, 21128, Perry Hall, MD 21128
$579,990

3 beds

|

3 baths

9314 FOUNDERS LN, PERRY HALL, MD, 21128
Community: Gerst Farm
New Leisure World® of Maryland 3312 CHISWICK CT 62-3A, SILVER SPRING, M..., Silver Spring, MD 20906
$87,500

1 beds

|

1 baths

|

800 sq ft

|

Condo

3312 CHISWICK CT 62-3A, SILVER SPRING, M...
New Snowden Overlook 8729 SAGE BRUSH WAY 63, COLUMBIA, MD, 21..., Columbia, MD 21045
$685,000

3 beds

|

5 baths

|

4,620 sq ft

|

Condo

8729 SAGE BRUSH WAY 63, COLUMBIA, MD, 21...
Community: Snowden Overlook
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.
New Leisure World® of Maryland 3330 N LEISURE WORLD BLVD 5-415, SILVER ..., Silver Spring, MD 20906
$137,700

2 beds

|

2 baths

|

980 sq ft

|

Condo

3330 N LEISURE WORLD BLVD 5-415, SILVER ...
New Birchwood at Brambleton 23631 HAVELOCK WALK TER 203, ASHBURN, VA..., Ashburn, VA 20148
$445,000

2 beds

|

2 baths

|

1,012 sq ft

|

Condo

23631 HAVELOCK WALK TER 203, ASHBURN, VA...
New Heritage Harbour 804 COXSWAIN WAY, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$630,000

2 beds

|

2 baths

|

1,547 sq ft

804 COXSWAIN WAY, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
New Two Rivers 1536 YELLOW SAND LN, ODENTON, MD, 21113, Odenton, MD 21113
$738,500

2 beds

|

4 baths

|

2,037 sq ft

1536 YELLOW SAND LN, ODENTON, MD, 21113
Community: Two Rivers
Heritage Harbour 816 BOATSWAIN WAY, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$819,900

3 beds

|

3 baths

|

2,450 sq ft

816 BOATSWAIN WAY, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
Leisure World® of Maryland 3321 S LEISURE WORLD BLVD 98-1A, SILVER ..., Silver Spring, MD 20906
$99,500

1 beds

|

1 baths

|

635 sq ft

|

Condo

3321 S LEISURE WORLD BLVD 98-1A, SILVER ...
Leisure World® of Maryland 3005 S LEISURE WORLD BLVD 304, SILVER SP..., Silver Spring, MD 20906
$349,900

2 beds

|

2 baths

|

1,506 sq ft

|

Condo

3005 S LEISURE WORLD BLVD 304, SILVER SP...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 408, LEESBURG, V..., Leesburg, VA 20176
$379,999

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

19355 CYPRESS RIDGE TER 408, LEESBURG, V...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Leisure World® of Maryland 14601 DEERHURST TER, SILVER SPRING, MD, ..., Silver Spring, MD 20906
$425,000

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

14601 DEERHURST TER, SILVER SPRING, MD, ...
Leisure World® of Maryland 15107 INTERLACHEN DR 2-621, SILVER SPRIN..., Silver Spring, MD 20906
$163,500

2 beds

|

2 baths

|

990 sq ft

|

Condo

15107 INTERLACHEN DR 2-621, 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.

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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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