Call us at (443) 647-4690 to learn more about active adult communities in New Windsor

New Windsor, MD 55+ active adult communities & homes for sale - Page 5

608 homes near New Windsor

Sort by:

Relevance

Relevance

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.
1234...5
The Flats at Heathcote Village by Del Webb 6156 AMBER LN 2, HAYMARKET, VA, 20169, Haymarket, VA 20169
$739,990

3 beds

|

3 baths

|

3,424 sq ft

6156 AMBER LN 2, HAYMARKET, VA, 20169
The Flats at Heathcote Village by Del Webb 6152 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$709,990

3 beds

|

3 baths

|

2,763 sq ft

6152 AMBER LN, HAYMARKET, VA, 20169
The Flats at Heathcote Village by Del Webb 6152 AMBER LN 2, HAYMARKET, VA, 20169, Haymarket, VA 20169
$749,990

3 beds

|

3 baths

|

3,531 sq ft

6152 AMBER LN 2, HAYMARKET, VA, 20169
Leisure World® of Maryland 3505 S LEISURE WORLD BLVD 29-2E, SILVER ..., Silver Spring, MD 20906
$160,000

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

3505 S LEISURE WORLD BLVD 29-2E, SILVER ...
Traditions of America at Silver Spring 298 FOUNDERS WAY, MECHANICSBURG, PA, 170..., Mechanicsburg, PA 17050
$519,000

2 beds

|

2 baths

|

2,463 sq ft

|

Condo

298 FOUNDERS WAY, MECHANICSBURG, PA, 170...
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Birchwood at Brambleton 23639 GOLDEN EMBERS SQ 302, ASHBURN, VA,..., Ashburn, VA 20148
$675,000

3 beds

|

2 baths

|

1,972 sq ft

|

Condo

23639 GOLDEN EMBERS SQ 302, ASHBURN, VA,...
Signature Club at Greenview 10619 NATHANIEL WAY 20, NEW MARKET, MD, ..., New Market, MD 21774
$549,999

4 beds

|

4 baths

|

2,752 sq ft

10619 NATHANIEL WAY 20, NEW MARKET, MD, ...
Arbor Gate 6 ROSEMONT DR, MYERSTOWN, PA, 17067, Myerstown, PA 17067
$287,000

2 beds

|

2 baths

|

1,747 sq ft

6 ROSEMONT DR, MYERSTOWN, PA, 17067
Community: Arbor Gate
Legacy at Fallston Commons 331 TUFTON CIR 102, FALLSTON, MD, 21047, Fallston, MD 21047
$520,000

3 beds

|

4 baths

|

3,526 sq ft

|

Condo

331 TUFTON CIR 102, FALLSTON, MD, 21047
Vistas at Lansdowne 44239 SILVERPALM GROVE TER, LEESBURG, VA..., Leesburg, VA 20176
$889,000

3 beds

|

4 baths

|

3,933 sq ft

44239 SILVERPALM GROVE TER, LEESBURG, VA...
Community: Vistas at Lansdowne
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 Villages At Woodholme 4415 SUMMER GRAPE 4415, PIKESVILLE, MD, ..., Pikesville, MD 21208
$500,000

3 beds

|

4 baths

|

4,378 sq ft

|

Condo

4415 SUMMER GRAPE 4415, PIKESVILLE, MD, ...
Leisure World® of Maryland 14805 PENNFIELD CIR 307, SILVER SPRING, ..., Silver Spring, MD 20906
$299,000

2 beds

|

2 baths

|

1,152 sq ft

|

Condo

14805 PENNFIELD CIR 307, SILVER SPRING, ...
The Village at Freedom Hills 13862 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740
$475,000

4 beds

|

2 baths

|

3,107 sq ft

13862 PATRIOT WAY, HAGERSTOWN, MD, 21740
Briar Lake 869 WATER EDGE CT L-0062 CT, LEBANON, PA..., Lebanon, PA 17046
$459,900

3 beds

|

2 baths

|

1,715 sq ft

869 WATER EDGE CT L-0062 CT, LEBANON, PA...
Community: Briar Lake
Four Seasons at Kent Island 230 SWITCHGRASS WAY 12, CHESTER, MD, 216..., Chester, MD 21619
$525,000

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

230 SWITCHGRASS WAY 12, CHESTER, MD, 216...
Traditions of America at Silver Spring 225 LOYAL DR, MECHANICSBURG, PA, 17050, Mechanicsburg, PA 17050
$564,900

4 beds

|

3 baths

|

2,563 sq ft

|

Condo

225 LOYAL DR, MECHANICSBURG, PA, 17050
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Heritage Hunt 7055 HERITAGE HUNT DR 111, GAINESVILLE, ..., Gainesville, VA 20155
$450,000

2 beds

|

2 baths

|

1,421 sq ft

|

Condo

7055 HERITAGE HUNT DR 111, GAINESVILLE, ...
Community: Heritage Hunt
The Atrium at MetroWest 2960 VADEN DR 2-413, FAIRFAX, VA, 22031, Fairfax, VA 22031
$749,900

2 beds

|

2 baths

|

1,391 sq ft

|

Condo

2960 VADEN DR 2-413, FAIRFAX, VA, 22031
Heritage Hunt 6845 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$740,000

4 beds

|

3 baths

|

2,068 sq ft

6845 SADDLE RUN WAY, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Spring Hill 8970 FASCINATION CT 112, LORTON, VA, 220..., Lorton, VA 22079
$465,000

2 beds

|

2 baths

|

1,367 sq ft

|

Condo

8970 FASCINATION CT 112, LORTON, VA, 220...
Community: Spring Hill
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.
Snowden Overlook 8893 SHINING OCEANS WAY 15, COLUMBIA, MD..., Columbia, MD 21045
$640,000

3 beds

|

4 baths

|

3,480 sq ft

|

Condo

8893 SHINING OCEANS WAY 15, COLUMBIA, MD...
Community: Snowden Overlook
Four Seasons at Kent Island 233 PEREGRINE DR, CHESTER, MD, 21619, Chester, MD 21619
$749,900

4 beds

|

3 baths

|

3,151 sq ft

233 PEREGRINE DR, CHESTER, MD, 21619
Heritage Harbour 2900 SHIPMASTER WAY 119, ANNAPOLIS, MD, ..., Annapolis, MD 21401
$285,000

2 beds

|

2 baths

|

1,018 sq ft

|

Condo

2900 SHIPMASTER WAY 119, ANNAPOLIS, MD, ...
Community: Heritage Harbour
Gerst Farm 9430 GERST RD, PERRY HALL, MD, 21128, Perry Hall, MD 21128
$529,990

3 beds

|

3 baths

|

2,690 sq ft

9430 GERST RD, PERRY HALL, MD, 21128
Community: Gerst Farm
Spring Valley Estates 11797 MYSTIC ROCK LN, WAYNESBORO, PA, 17..., Waynesboro, PA 17268
$364,900

3 beds

|

3 baths

|

1,850 sq ft

11797 MYSTIC ROCK LN, WAYNESBORO, PA, 17...
Leisure World® of Maryland 3330 N LEISURE WORLD BLVD 5-102, SILVER ..., Silver Spring, MD 20906
$315,000

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

3330 N LEISURE WORLD BLVD 5-102, SILVER ...
Vistas at Lansdowne 44238 SILVERPALM GROVE TER, LEESBURG, VA..., Leesburg, VA 20176
$865,000

3 beds

|

5 baths

|

3,891 sq ft

44238 SILVERPALM GROVE TER, LEESBURG, VA...
Community: Vistas at Lansdowne
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
Four Seasons at Kent Island 1000 HERONS NEST WAY 23, CHESTER, MD, 21..., Chester, MD 21619
$490,000

2 beds

|

3 baths

|

Condo

1000 HERONS NEST WAY 23, CHESTER, MD, 21...
Leisure World® of Maryland 2904 N LEISURE WORLD BLVD 308, SILVER SP..., Silver Spring, MD 20906
$300,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

2904 N LEISURE WORLD BLVD 308, SILVER SP...
Amblebrook 185 LIVELY STREAM WAY, GETTYSBURG, PA, 1..., Gettysburg, PA 17325
$519,900

2 beds

|

3 baths

|

2,356 sq ft

185 LIVELY STREAM WAY, GETTYSBURG, PA, 1...
Community: Amblebrook
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 Forest Glen 8609 WINTERGREEN CT 208, ODENTON, MD, 21..., Odenton, MD 21113
$369,900

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

8609 WINTERGREEN CT 208, ODENTON, MD, 21...
Spring Hill 8406 MOUNTAIN LARKSPUR DR DR, LORTON, VA..., Lorton, VA 22079
$867,000

3 beds

|

3 baths

|

2,546 sq ft

8406 MOUNTAIN LARKSPUR DR DR, LORTON, VA...
Community: Spring Hill
Carmella 425 CARMELLA DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050
$485,000

3 beds

|

3 baths

|

2,479 sq ft

|

Condo

425 CARMELLA DR, MECHANICSBURG, PA, 1705...
Community: Carmella
Leisure World® of Maryland 3310 N LEISURE WORLD BLVD 108-6, SILVER ..., Silver Spring, MD 20906
$188,000

2 beds

|

2 baths

|

1,195 sq ft

|

Condo

3310 N LEISURE WORLD BLVD 108-6, SILVER ...
Ballenger Run 5307 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703
$529,900

3 beds

|

4 baths

|

2,669 sq ft

5307 CRAPE MYRTLE DR, FREDERICK, MD, 217...
Community: Ballenger Run
Alden Place 1012 BRANDYWINE DR, LEBANON, PA, 17042, Lebanon, PA 17042
$549,000

2 beds

|

2 baths

|

2,298 sq ft

1012 BRANDYWINE DR, LEBANON, PA, 17042
Community: Alden Place
Heritage Harbour 2608 QUIET WATER CV 26, ANNAPOLIS, MD, 2..., Annapolis, MD 21401
$499,000

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

2608 QUIET WATER CV 26, ANNAPOLIS, MD, 2...
Community: Heritage Harbour
Carroll's Creek 1403 WIGEON WAY 302, GAMBRILLS, MD, 2105..., Gambrills, MD 21054
$375,000

2 beds

|

2 baths

|

1,343 sq ft

|

Condo

1403 WIGEON WAY 302, GAMBRILLS, MD, 2105...
Community: Carroll's Creek
Want to learn more about 55+ communities in New Windsor? 55places can help!
Questions? Call us: (443) 647-4690
The Preserves at Cumberland Village 33 BOBOLINK DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$389,900

3 beds

|

3 baths

|

2,046 sq ft

33 BOBOLINK DR, GETTYSBURG, PA, 17325
Dunbarton 12904 FETLAR WAY, BRISTOW, VA, 20136, Bristow, VA 20136
$589,500

2 beds

|

2 baths

|

2,008 sq ft

12904 FETLAR WAY, 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.

Frequently Asked Questions


Want more information about active adult communities around New Windsor?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

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

Call us: (443) 647-4690
608 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

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.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Jul 30, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top