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Maryland 55+ active adult communities & homes for sale - Page 19

Living in Maryland

Maryland offers the best of both worlds for retirees — proximity to Washington D.C. and Baltimore with suburban and rural communities just minutes away. No tax on Social…
Maryland offers the best of both worlds for retirees — proximity to Washington D.C. and Baltimore with suburban and rural communities just minutes away. No tax on Social Security, strong healthcare access with Johns Hopkins and the University of Maryland Medical System, and four seasons with mild winters compared to the Northeast make it a top-tier retirement state on the East Coast.

Maryland is home to 244 active adult communities, with homes ranging from the low $200Ks to over $1M and averaging around $512K. Leisure World of Maryland in Silver Spring (5,600 homes) is one of the largest 55+ communities on the East Coast. Heritage Harbour near Annapolis (1,683 homes) and Cameron Grove in Upper Marlboro offer closer access to the Chesapeake Bay lifestyle. On the Eastern Shore, Four Seasons at Kent Island combines waterfront living with a quieter pace. 55places has profiled every community with verified pricing, resident reviews, and local agent connections.

Quick Facts About Retiring in Maryland


1,081 homes near Maryland

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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
5 rating (1 reviews) Snowden Overlook
$300ks - $600ks
Snowden Overlook, Columbia, MD
Resale Only | 55+ age-restricted | Built 2005 - 2010 | 350 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
3.7 rating (3 reviews) Heritage Harbour
$300ks - $800ks
Heritage Harbour, Annapolis, MD
Resale Only | 55+ age-restricted | Built 1979 - 2008 | 1,683 homes
5 rating (1 reviews) Two Rivers
$500ks - $700ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
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
Cameron Grove
$200ks - $400ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 homes
5 rating (2 reviews) The Parke at Ocean Pines
$200ks - $600ks
The Parke at Ocean Pines, Ocean Pines, MD
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 503 homes
5 rating (1 reviews) Symphony Village
$300ks - $500ks
Symphony Village, Centreville, MD
Resale Only | 55+ age-restricted | Built 2003 - 2016 | 395 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.
Parklands
$300ks - $500ks
Parklands, White Plains, MD
New Construction | 55+ age-restricted | Built 2025 - present | 586 homes
5 rating (2 reviews) Noble's Pond
$200ks - $300ks
Noble's Pond, Dover, DE
New and Resale | 55+ age-restricted | Built 2007 - present | 800 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
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 (2 reviews) Heritage Shores
$200ks - $500ks
Heritage Shores, Bridgeville, DE
New and Resale | 55+ age-restricted | Built 2004 - present | 1,816 homes
5 rating (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
3.1 rating (7 reviews) Celebrate
$300ks - $600ks
Celebrate, Fredericksburg, VA
New and Resale | 55+ age-restricted | Built 2008 - present | 1,100 homes
Chesapeake
$300ks - $400ks
Chesapeake, Easton, MD
Resale Only | 55+ age-restricted | Built 2002 - 2011 | 452 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
4.4 rating (5 reviews) Virginia Heritage at Lee'...
$300ks - $500ks
Virginia Heritage at Lee'..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2005 - 2021 | 795 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.
The Village of Cinderberr...
$200ks - $300ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 homes
1.7 rating (3 reviews) Silver Woods
$400ks - $500ks
Silver Woods, Ocean View, DE
New and Resale | Age-targeted | Built 2005 - present | 111 homes
Traditions at Whitehall
$400ks - $500ks
Traditions at Whitehall, Middletown, DE
New Construction | 55+ age-restricted | Built 2019 - present | 250 homes
5 rating (1 reviews) Keswick Villas
$300ks - $500ks
Keswick Villas, Spotsylvania, VA
New Construction | 55+ age-restricted | Built 2020 - present | 84 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
Four Seasons at Hatteras ...
$400ks - $500ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 homes
Venue at Winchelsea
$400ks - $600ks
Venue at Winchelsea, Middletown, DE
New Construction | 55+ age-restricted | Built 2024 - present | 336 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
2.8 rating (4 reviews) The Villages at Red Mill ...
$400ks - $600ks
The Villages at Red Mill ..., Lewes, DE
New and Resale | Age-targeted | Built 2009 - present | 520 homes
5 rating (3 reviews) Village of Eastridge
$300ks - $400ks
Village of Eastridge, Smyrna, DE
New Construction | 55+ age-restricted | Built 2014 - present | 189 homes
The Villas at The Preserv...
$400ks
The Villas at The Preserv..., Townsend, DE
New Construction | 55+ age-restricted | Built 2017 - present | 144 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.
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
Liberty West
$400ks
Liberty West, Georgetown, DE
New Construction | Age-targeted | Built 2025 - present | 181 homes
Sundance Club
$500ks - $800ks
Sundance Club, Frankford, DE
New Construction | 55+ age-restricted | Built 2026 - present | 180 homes
Carriages at Orchard Glen
$400ks - $500ks
Carriages at Orchard Glen, Elk Township, NJ
New Construction | 55+ age-restricted | Built 2026 - present | 250 homes
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 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
The Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
3.7 rating (3 reviews) Spring Meadow
$300ks - $400ks
Spring Meadow, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes
5 rating (1 reviews) Four Seasons at Historic ...
$400ks - $600ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 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.
Four Seasons at Kent Island 102 BOATSWAIN WAY 2933, CHESTER, MD, 216..., Chester, MD 21619
$809,990

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

102 BOATSWAIN WAY 2933, CHESTER, MD, 216...
Emerald Hills 1604 MARTHA CT 101, BEL AIR, MD, 21015, Bel Air, MD 21015
$269,900

2 beds

|

2 baths

|

1,240 sq ft

|

Condo

1604 MARTHA CT 101, BEL AIR, MD, 21015
Community: Emerald Hills
Parke Place 38 PITMAN PL, SEWELL, NJ, 08080, Sewell, NJ 08080
$395,000

2 beds

|

2 baths

|

1,518 sq ft

38 PITMAN PL, SEWELL, NJ, 08080
Community: Parke Place
Legacy at Waterford Pines 22 JOSIE LN, ATCO, NJ, 08004, Atco, NJ 08004
$465,000

3 beds

|

3 baths

|

1,966 sq ft

22 JOSIE LN, ATCO, NJ, 08004
Central Parke at Victoria Falls 13851 BELLE CHASSE BLVD 213, LAUREL, MD,..., Laurel, MD 20707
$395,000

3 beds

|

2 baths

|

1,703 sq ft

|

Condo

13851 BELLE CHASSE BLVD 213, LAUREL, MD,...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Emerald Pointe 19419 AMETHYST DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$379,000

2 beds

|

2 baths

|

2,394 sq ft

19419 AMETHYST DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Heritage Shores 336 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$429,000

3 beds

|

2 baths

|

1,507 sq ft

336 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Longacre Village 216 N RED HAVEN LN, DOVER, DE, 19901, Dover, DE 19901
$379,500

2 beds

|

2 baths

|

1,764 sq ft

216 N RED HAVEN LN, DOVER, DE, 19901
Community: Longacre Village
Crestwood Village 5603 HONEYSUCKLE CT, FREDERICK, MD, 2170..., Frederick, MD 21703
$412,000

2 beds

|

1 baths

|

1,297 sq ft

5603 HONEYSUCKLE CT, FREDERICK, MD, 2170...
Community: Crestwood Village
Chesapeake 7401 CASEY AVE, EASTON, MD, 21601, Easton, MD 21601
$534,900

3 beds

|

3 baths

|

2,342 sq ft

7401 CASEY AVE, EASTON, MD, 21601
Community: Chesapeake
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 Meadow 594 SORRELL CIR, SMYRNA, DE, 19977, Smyrna, DE 19977
$312,000

2 beds

|

2 baths

|

1,323 sq ft

594 SORRELL CIR, SMYRNA, DE, 19977
Community: Spring Meadow
Four Seasons at Kent Island 121 MERLIN DR, CHESTER, MD, 21619, Chester, MD 21619
$697,900

2 beds

|

2 baths

|

2,118 sq ft

121 MERLIN DR, CHESTER, MD, 21619
The Ponds at Bayberry 4200 CROSBY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709
$659,900

4 beds

|

3 baths

|

2,700 sq ft

4200 CROSBY LN, MIDDLETOWN, DE, 19709
Leisure World® of Maryland 15107 INTERLACHEN DR 2-115, SILVER SPRIN..., Silver Spring, MD 20906
$235,000

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

15107 INTERLACHEN DR 2-115, SILVER SPRIN...
Ashland 145 E CLARENDON DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$379,900

2 beds

|

2 baths

|

1,796 sq ft

145 E CLARENDON DR, SMYRNA, DE, 19977
Community: Ashland
Cindy Certified
1650 SILVER HILL DR 1206, MCLEAN, VA, 22..., Mclean, VA 22102
$1,325,000

2 beds

|

2 baths

|

1,617 sq ft

|

Condo

1650 SILVER HILL DR 1206, MCLEAN, VA, 22...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Leisure World® of Maryland 3330 GLENEAGLES DR 68-2D, SILVER SPRING,..., Silver Spring, MD 20906
$159,000

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

3330 GLENEAGLES DR 68-2D, SILVER SPRING,...
Regency at Dominion Valley 5416 ZOYSIA CT, HAYMARKET, VA, 20169, Haymarket, VA 20169
$824,900

4 beds

|

4 baths

|

3,962 sq ft

5416 ZOYSIA CT, HAYMARKET, VA, 20169
Leisure World® of Maryland 3466 CHISWICK CT 43-2A, SILVER SPRING, M..., Silver Spring, MD 20906
$165,000

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

3466 CHISWICK CT 43-2A, SILVER SPRING, M...
Bishop's Landing 30243 BRANDYWINE DR, MILLVILLE, DE, 1996..., Millville, DE 19967
$649,900

5 beds

|

4 baths

|

3,300 sq ft

30243 BRANDYWINE DR, MILLVILLE, DE, 1996...
Community: Bishop's Landing
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.
Cromwell 55+ 6144 BECK OVERLOOK, IJAMSVILLE, MD, 2175..., Ijamsville, MD 21754
$699,990

2 beds

|

2 baths

|

3,387 sq ft

6144 BECK OVERLOOK, IJAMSVILLE, MD, 2175...
Community: Cromwell 55+
Whispering Woods 1428 WHISPERING WOODS RD, MIDDLETOWN, DE..., Middletown, DE 19709
$423,000

2 beds

|

2 baths

|

1,275 sq ft

1428 WHISPERING WOODS RD, MIDDLETOWN, DE...
Community: Whispering Woods
Cindy Certified
636 WALLINGFORD RD 3G, BEL AIR, MD, 2101..., Bel Air, MD 21014
$398,000

2 beds

|

3 baths

|

1,671 sq ft

|

Condo

636 WALLINGFORD RD 3G, BEL AIR, MD, 2101...
The Flats at Northside 1135 POLARIS RD 90, POTOMAC, MD, 20854, Potomac, MD 20854
$1,642,700

3 beds

|

5 baths

|

3,470 sq ft

1135 POLARIS RD 90, POTOMAC, MD, 20854
The Flats at Northside 1135 POLARIS RD 75, POTOMAC, MD, 20854, Potomac, MD 20854
$1,424,100

4 beds

|

3 baths

|

2,840 sq ft

1135 POLARIS RD 75, POTOMAC, MD, 20854
The Flats at Northside 1135 POLARIS RD 101, POTOMAC, MD, 20854, Potomac, MD 20854
$1,698,975

4 beds

|

5 baths

|

3,470 sq ft

1135 POLARIS RD 101, POTOMAC, MD, 20854
The Enclave at Ellicott Hills 2649 BUCKINGHAM RD 43, ELLICOTT CITY, MD..., Ellicott City, MD 21043
$700,000

3 beds

|

4 baths

|

3,018 sq ft

|

Condo

2649 BUCKINGHAM RD 43, ELLICOTT CITY, MD...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 203, HAYMARKET, VA, 2..., Haymarket, VA 20169
$500,005

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

5800 MOONSTONE WAY 203, HAYMARKET, VA, 2...
Walhaven at Kingstowne 5951 CLAPTON CT, ALEXANDRIA, VA, 22310, Alexandria, VA 22310
$879,000

3 beds

|

4 baths

|

2,804 sq ft

|

Condo

5951 CLAPTON CT, ALEXANDRIA, VA, 22310
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 202, HAYMARKET, VA, 2..., Haymarket, VA 20169
$612,140

3 beds

|

2 baths

|

1,850 sq ft

|

Condo

5800 MOONSTONE WAY 202, HAYMARKET, VA, 2...
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 Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 104, HAYMARKET, VA, 2..., Haymarket, VA 20169
$436,065

2 beds

|

2 baths

|

1,345 sq ft

|

Condo

5800 MOONSTONE WAY 104, HAYMARKET, VA, 2...
The Flats at Heathcote Village by Del Webb 6156 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$699,990

3 beds

|

3 baths

|

2,625 sq ft

6156 AMBER LN, HAYMARKET, VA, 20169
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
Whispering Woods 529 CONTEMPLATION WAY, MIDDLETOWN, DE, 1..., Middletown, DE 19709
$559,900

3 beds

|

3 baths

|

2,375 sq ft

529 CONTEMPLATION WAY, MIDDLETOWN, DE, 1...
Community: Whispering Woods
Heritage Shores 322 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$489,990

3 beds

|

3 baths

|

2,292 sq ft

322 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Leisure World® of Maryland 3505 S LEISURE WORLD BLVD 29-2E, SILVER ..., Silver Spring, MD 20906
$140,000

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

3505 S LEISURE WORLD BLVD 29-2E, SILVER ...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Holiday City at Monroe 600 TRINIDAD BLVD, WILLIAMSTOWN, NJ, 080..., Williamstown, NJ 08094
$299,000

2 beds

|

2 baths

|

1,260 sq ft

600 TRINIDAD BLVD, WILLIAMSTOWN, NJ, 080...
Birchwood at Brambleton 23639 GOLDEN EMBERS SQ 302, ASHBURN, VA,..., Ashburn, VA 20148
$640,000

3 beds

|

2 baths

|

1,972 sq ft

|

Condo

23639 GOLDEN EMBERS SQ 302, ASHBURN, VA,...
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 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: Oct 07, 2026.
This application does not include information on all of the properties available for sale at this time.

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