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

162 communities 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

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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

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

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

1 2 3 4...5

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

$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...

Community: Four Seasons at Kent Island

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...

Community: Four Seasons at Kent Island

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

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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

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 ...

Community: Leisure World® of Maryland

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

Community: Four Seasons at Kent Island

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...

Community: Four Seasons at Kent Island

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 ...

Community: Leisure World® of Maryland

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...

Community: Leisure World® of Maryland

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

Community: The Village at Foxfield

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

Community: The Village at Foxfield

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...

Community: Regency at Dominion Valley

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 ...

Community: Leisure World® of Maryland

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...

Community: Leisure World® of Maryland

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

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 ...

Community: Leisure World® of Maryland

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...

Community: Birchwood at Brambleton

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 ...

Community: Leisure World® of Maryland

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...

Community: Leisure World® of Maryland

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...

Community: Lansdowne Woods of Virginia

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, ...

Community: Leisure World® of Maryland

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...

Community: Leisure World® of Maryland

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 1086 days. The average price of homes for sale in this community is approximately $434,500, 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 $434,500.

Want more information about active adult communities around New Windsor?

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

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162 communities

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REIN updates its listings on a daily basis. Data last updated: Jul 30, 2026.
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New Windsor, MD 55+ active adult communities & homes for sale

162 communities near New Windsor

608 homes near New Windsor

3 beds

3 baths

2,300 sq ft

Condo

2 beds

2 baths

1,292 sq ft

Condo

3 beds

3 baths

2,602 sq ft

Condo

2 beds

3 baths

2,003 sq ft

Condo

2 beds

2 baths

2,130 sq ft

2 beds

3 baths

2,036 sq ft

2 beds

2 baths

1,661 sq ft

2 beds

2 baths

1,409 sq ft

3 beds

4 baths

2,332 sq ft

2 beds

2 baths

1,208 sq ft

2 beds

2 baths

1,408 sq ft

2 beds

2 baths

953 sq ft

Condo

2 beds

2 baths

1,046 sq ft

Condo

3 beds

2 baths

1,736 sq ft

3 beds

5 baths

4,208 sq ft

Condo

2 beds

3 baths

2,010 sq ft

2 beds

3 baths

2,003 sq ft

Condo

4 beds

4 baths

4,605 sq ft

2 beds

2 baths

1,138 sq ft

Condo

3 beds

2 baths

1,789 sq ft

Condo

2 beds

2 baths

1,359 sq ft

3 beds

3 baths

2,208 sq ft

2 beds