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

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

Want to learn more about 55+ communities in New Windsor? 55places can help!

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

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

1 2 3...4

Leisure World® of Maryland

3352 CHISWICK CT 57-3E, SILVER SPRING, M..., Silver Spring, MD 20906

$103,000

1 beds

1 baths

800 sq ft

Condo

3352 CHISWICK CT 57-3E, SILVER SPRING, M...

Community: Leisure World® of Maryland

Heritage Harbour

803 COXSWAIN WAY UNIT 203, ANNAPOLIS, MD..., Annapolis, MD 21401

$379,900

2 beds

2 baths

1,190 sq ft

Condo

803 COXSWAIN WAY UNIT 203, ANNAPOLIS, MD...

Community: Heritage Harbour

Heritage Harbour

905 BEACON WAY, ANNAPOLIS, MD, 21401, Annapolis, MD 21401

$489,000

2 beds

2 baths

1,394 sq ft

905 BEACON WAY, ANNAPOLIS, MD, 21401

Community: Heritage Harbour

Leisure World® of Maryland

3005 S LEISURE WORLD BLVD 821, SILVER SP..., Silver Spring, MD 20906

$375,000

2 beds

2 baths

1,601 sq ft

Condo

3005 S LEISURE WORLD BLVD 821, SILVER SP...

Community: Leisure World® of Maryland

Four Seasons at Kent Island

141 SWITCHGRASS WAY 34, CHESTER, MD, 216..., Chester, MD 21619

$684,950

3 beds

3 baths

2,600 sq ft

Condo

141 SWITCHGRASS WAY 34, CHESTER, MD, 216...

Condo

6509 GOLDEN SPRING LN 76, COLUMBIA, MD, ...

Community: Hickory Crest

Want to learn more about 55+ communities in New Windsor? 55places can help!

Questions? Call us: (443) 647-4690

Cameron Grove

12916 FOX BOW DR APT 107, UPPER MARLBORO..., Upper Marlboro, MD 20774

$324,999

2 beds

2 baths

1,116 sq ft

Condo

12916 FOX BOW DR APT 107, UPPER MARLBORO...

Community: Cameron Grove

Signature Club at Greenview

5810 WHITEROSE WAY, NEW MARKET, MD, 2177..., New Market, MD 21774

$465,000

3 beds

4 baths

2,410 sq ft

5810 WHITEROSE WAY, NEW MARKET, MD, 2177...

Community: Signature Club at Greenview

Snowden Overlook

8790 SAGE BRUSH WAY 19, COLUMBIA, MD, 21..., Columbia, MD 21045

$639,900

4 beds

4 baths

4,619 sq ft

8790 SAGE BRUSH WAY 19, COLUMBIA, MD, 21...

Community: Snowden Overlook

Signature Club at Greenview

5948 JACOBEAN PL, NEW MARKET, MD, 21774, New Market, MD 21774

$660,000

3 beds

3 baths

3,123 sq ft

Condo

5948 JACOBEAN PL, NEW MARKET, MD, 21774

Community: Signature Club at Greenview

Leisure World® of Maryland

3431 S LEISURE WORLD BLVD 88-3C, SILVER ..., Silver Spring, MD 20906

$115,000

2 beds

1 baths

1,035 sq ft

Condo

3431 S LEISURE WORLD BLVD 88-3C, SILVER ...

Community: Leisure World® of Maryland

Cedar Ridge at Piney Orchard

8608 WANDERING FOX TRL 303, ODENTON, MD,..., Odenton, MD 21113

$400,000

2 beds

2 baths

1,700 sq ft

Condo

8608 WANDERING FOX TRL 303, ODENTON, MD,...

Community: Cedar Ridge at Piney Orchard

Heritage Harbour

930 ASTERN WAY 405, ANNAPOLIS, MD, 21401, Annapolis, MD 21401

$379,900

2 beds

2 baths

1,464 sq ft

Condo

930 ASTERN WAY 405, ANNAPOLIS, MD, 21401

Community: Heritage Harbour

Snowden Overlook

8879 WARM GRANITE DR # 27, COLUMBIA, MD,..., Columbia, MD 21045

$650,000

4 beds

5 baths

4,196 sq ft

Condo

8879 WARM GRANITE DR # 27, COLUMBIA, MD,...

Community: Snowden Overlook

Winifred Manor

2010 RUDY SERRA DR C, SYKESVILLE, MD, 21..., Sykesville, MD 21784

$275,000

2 beds

2 baths

1,080 sq ft

Condo

2010 RUDY SERRA DR C, SYKESVILLE, MD, 21...

Community: Winifred Manor

Villas at Cattail Creek

15124 PLAYERS WAY 7, GLENWOOD, MD, 21738, Glenwood, MD 21738

$609,000

4 beds

4 baths

4,297 sq ft

Condo

15124 PLAYERS WAY 7, GLENWOOD, MD, 21738

Community: Villas at Cattail Creek

Want to learn more about 55+ communities in New Windsor? 55places can help!

Questions? Call us: (443) 647-4690

The Villages At Woodholme

8325 MEADOWSWEET RD # 8325, BALTIMORE, M..., Baltimore, MD 21208

$500,000

3 beds

3 baths

3,144 sq ft

Condo

8325 MEADOWSWEET RD # 8325, BALTIMORE, M...

Community: The Villages At Woodholme

Leisure World® of Maryland

2 FINSBURY PARK CT # 47-A, SILVER SPRING..., Silver Spring, MD 20906

$445,000

3 beds

2 baths

1,193 sq ft

Condo

2 FINSBURY PARK CT # 47-A, SILVER SPRING...

Community: Leisure World® of Maryland

Leisure World® of Maryland

3434 GLENEAGLES DR # 78-B, SILVER SPRING..., Silver Spring, MD 20906

$262,000

2 beds

3 baths

1,600 sq ft

Condo

3434 GLENEAGLES DR # 78-B, SILVER SPRING...

Community: Leisure World® of Maryland

Gatherings at Forest Glen

8603 WINTERGREEN CT UNIT 201, ODENTON, M..., Odenton, MD 21113

$340,000

2 beds

2 baths

1,500 sq ft

Condo

8603 WINTERGREEN CT UNIT 201, ODENTON, M...

Community: Gatherings at Forest Glen

The Woodlands of Urbana

2928 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704

$725,000

3 beds

4 baths

3,634 sq ft

2928 HERB GARDEN DR, FREDERICK, MD, 2170...

Community: The Woodlands of Urbana

The Courtyards at Waverly Woods

2350 ADAM DAVID WAY, MARRIOTTSVILLE, MD,..., Marriottsville, MD 21104

$670,000

3 beds

3 baths

3,444 sq ft

2350 ADAM DAVID WAY, MARRIOTTSVILLE, MD,...

Community: The Courtyards at Waverly Woods

Heritage Harbour

932 RIVERSEDGE CIR, ANNAPOLIS, MD, 21401, Annapolis, MD 21401

3 beds

2 baths

1,740 sq ft

Condo

2540 KENSINGTON GDNS 204, ELLICOTT CITY,...

Community: The Enclave at Ellicott Hills

Want to learn more about 55+ communities in New Windsor? 55places can help!

Questions? Call us: (443) 647-4690

Emerald Pointe

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$359,900

2 beds

2 baths

1,834 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Emerald Pointe

13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$449,900

2 beds

2 baths

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Four Seasons at Kent Island

130 SUNRISE CT, CHESTER, MD, 21619, Chester, MD 21619

$949,900

3 beds

4 baths

3,494 sq ft

130 SUNRISE CT, CHESTER, MD, 21619

Community: Four Seasons at Kent Island

The Villages At Woodholme

8330 MEADOWSWEET RD # 8330, PIKESVILLE, ..., Pikesville, MD 21208

$469,000

3 beds

4 baths

4,056 sq ft

Condo

8330 MEADOWSWEET RD # 8330, PIKESVILLE, ...

Community: The Villages At Woodholme

Leisure World® of Maryland

2900 N LEISURE WORLD BLVD APT 312, SILVE..., Silver Spring, MD 20906

$175,000

1 beds

1 baths

896 sq ft

Condo

2900 N LEISURE WORLD BLVD APT 312, SILVE...

Community: Leisure World® of Maryland

1 2 3 4 5 6 7 8 9 10 11 12 13…14

Frequently Asked Questions

What size 55+ communities are there in New Windsor?

In New Windsor, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in New Windsor?

The smallest 55+ community in New Windsor has 83 homes, the largest has 83 homes, and the average community consists of 83 homes.

Are there gated 55+ communities in New Windsor?

No, there are no gated 55+ communities in New Windsor.

How long do listings in 55+ communities in New Windsor typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in New Windsor stay on the market for around 791 days. The average price of homes for sale in this community is approximately $429,495, though prices can range widely based on the size, location, and amenities of the community. For example, homes in The Reserve at New Windsor average around $429,495.

Want more information about active adult communities around New Windsor?

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Want to learn more about 55+ communities in New Windsor?

Call us: (443) 647-4690

544 homes near New Windsor

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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
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REIN updates its listings on a daily basis. Data last updated: Nov 17, 2025.
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New Windsor, MD 55+ active adult communities & homes for sale

152 communities near New Windsor

544 homes near New Windsor

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,190 sq ft

Condo

2 beds

2 baths

1,394 sq ft

2 beds

2 baths

1,601 sq ft

Condo

3 beds

3 baths

2,600 sq ft

Condo

3 beds

4 baths

3,800 sq ft

Condo

2 beds

2 baths

1,136 sq ft

Condo

2 beds

2 baths

1,043 sq ft

Condo

2 beds

2 baths

1,030 sq ft

Condo

2 beds

3 baths

1,900 sq ft

Condo

2 beds

3 baths

1,900 sq ft

Condo

2 beds

2 baths

980 sq ft

Condo

2 beds

3 baths

1,359 sq ft

Condo

2 beds

2 baths

1,460 sq ft

Condo

2 beds

3 baths

2,358 sq ft

Condo

2 beds

2 baths

1,116 sq ft

Condo

3 beds

4 baths

2,410 sq ft

4 beds

4 baths

4,619 sq ft

3 beds

3 baths

3,123 sq ft

Condo

2 beds

1 baths

1,035 sq ft

Condo