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Maryland 55+ active adult communities & homes for sale - Page 17

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.
Belmont Bay 680 WATERMANS, WOODBRIDGE, VA, 22191, Woodbridge, VA 22191
$399,900

2 beds

|

3 baths

|

1,413 sq ft

|

Condo

680 WATERMANS, WOODBRIDGE, VA, 22191
Community: Belmont Bay
Cindy Certified
6765 AZALEA GARDEN LN, HAYMARKET, VA, 20..., Haymarket, VA 20169
$725,000

2 beds

|

2 baths

|

1,609 sq ft

6765 AZALEA GARDEN LN, HAYMARKET, VA, 20...
Two Rivers 2719 ORCHARD ORIOLE WAY, ODENTON, MD, 21..., Odenton, MD 21113
$999,000

4 beds

|

5 baths

|

5,042 sq ft

2719 ORCHARD ORIOLE WAY, ODENTON, MD, 21...
Community: Two Rivers
Cadence at Lansdowne 43928 MARITIME SONG TER, LEESBURG, VA, 2..., Leesburg, VA 20176
$945,000

5 beds

|

5 baths

|

3,969 sq ft

43928 MARITIME SONG TER, LEESBURG, VA, 2...
Heritage Hunt 13919 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$769,000

4 beds

|

4 baths

|

4,779 sq ft

13919 CHELMSFORD DR, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Chesapeake 29720 LYONS DR, EASTON, MD, 21601, Easton, MD 21601
$465,000

2 beds

|

2 baths

|

1,940 sq ft

29720 LYONS DR, EASTON, MD, 21601
Community: Chesapeake
The Village at Foxfield 7 DERR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$600,000

3 beds

|

3 baths

|

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769
The Woodlands of Urbana 3231 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$700,000

3 beds

|

3 baths

|

2,612 sq ft

3231 THORNAPPLE DR, FREDERICK, MD, 21704
Celebrate 212 DENISON ST, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$449,900

2 beds

|

2 baths

|

1,595 sq ft

212 DENISON ST, FREDERICKSBURG, VA, 2240...
Community: Celebrate
River Crossing at Spring Arbor 5714 SPRING ARBOR CIR, FREDERICKSBURG, V..., Fredericksburg, VA 22407
$525,000

3 beds

|

3 baths

|

2,484 sq ft

5714 SPRING ARBOR CIR, FREDERICKSBURG, V...
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 8729 SAGE BRUSH WAY 63, COLUMBIA, MD, 21..., Columbia, MD 21045
$695,000

3 beds

|

5 baths

|

4,620 sq ft

|

Condo

8729 SAGE BRUSH WAY 63, COLUMBIA, MD, 21...
Community: Snowden Overlook
Two Rivers 1536 YELLOW SAND LN, ODENTON, MD, 21113, Odenton, MD 21113
$712,000

2 beds

|

4 baths

|

3,590 sq ft

1536 YELLOW SAND LN, ODENTON, MD, 21113
Community: Two Rivers
Four Seasons at Historic Virginia 3994 MELTING SNOW PL, DUMFRIES, VA, 2202..., Dumfries, VA 22025
$655,000

4 beds

|

3 baths

|

3,422 sq ft

3994 MELTING SNOW PL, DUMFRIES, VA, 2202...
Leisure World® of Maryland 3321 S LEISURE WORLD BLVD 98-1A, SILVER ..., Silver Spring, MD 20906
$93,000

1 beds

|

1 baths

|

635 sq ft

|

Condo

3321 S LEISURE WORLD BLVD 98-1A, SILVER ...
The Ponds at Bayberry 4534 CAGNEY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709
$585,000

4 beds

|

3 baths

|

3,025 sq ft

4534 CAGNEY LN, MIDDLETOWN, DE, 19709
Suffield Meadows 6727 HOLLY FARM LN, WARRENTON, VA, 20187, Warrenton, VA 20187
$659,000

4 beds

|

3 baths

|

3,066 sq ft

|

Condo

6727 HOLLY FARM LN, WARRENTON, VA, 20187
Community: Suffield Meadows
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
The Courtyards at Waverly Woods 2420 WALKING JANELLE WAY, MARRIOTTSVILLE..., Marriottsville, MD 21104
$675,000

4 beds

|

4 baths

|

3,612 sq ft

2420 WALKING JANELLE WAY, MARRIOTTSVILLE...
Chesapeake 29833 HILLARY AVE, EASTON, MD, 21601, Easton, MD 21601
$485,000

3 beds

|

3 baths

|

2,800 sq ft

29833 HILLARY AVE, EASTON, MD, 21601
Community: Chesapeake
The Village Grande at Camelot 111 WEATHERBY LN, GLASSBORO, NJ, 08028, Glassboro, NJ 08028
$549,900

3 beds

|

3 baths

|

2,613 sq ft

111 WEATHERBY LN, GLASSBORO, NJ, 08028
Heritage Hunt 13890 CHELMSFORD DR 305, GAINESVILLE, VA..., Gainesville, VA 20155
$425,000

2 beds

|

2 baths

|

1,388 sq ft

|

Condo

13890 CHELMSFORD DR 305, GAINESVILLE, VA...
Community: Heritage Hunt
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.
Leisure World® of Maryland 15301 BEAVERBROOK CT 92-3G, SILVER SPRIN..., Silver Spring, MD 20906
$225,000

2 beds

|

2 baths

|

1,122 sq ft

|

Condo

15301 BEAVERBROOK CT 92-3G, SILVER SPRIN...
Leisure World® of Maryland 3005 S LEISURE WORLD BLVD 211, SILVER SP..., Silver Spring, MD 20906
$357,000

2 beds

|

2 baths

|

1,446 sq ft

|

Condo

3005 S LEISURE WORLD BLVD 211, SILVER SP...
Leisure World® of Maryland 15100 INTERLACHEN DR 4-117, SILVER SPRIN..., Silver Spring, MD 20906
$224,000

2 beds

|

2 baths

|

1,317 sq ft

|

Condo

15100 INTERLACHEN DR 4-117, SILVER SPRIN...
Cindy Certified
8111 RIVER RD 122, BETHESDA, MD, 20817, Bethesda, MD 20817
$1,875,000

2 beds

|

2 baths

|

2,481 sq ft

|

Condo

8111 RIVER RD 122, BETHESDA, MD, 20817
The Cascades 678 MAYFIELD FALLS DR, NEWARK, DE, 19702, Newark, DE 19702
$514,900

3 beds

|

2 baths

|

1,904 sq ft

678 MAYFIELD FALLS DR, NEWARK, DE, 19702
Community: The Cascades
Cameron Grove 14040 NEW ACADIA LN 405, UPPER MARLBORO,..., Upper Marlboro, MD 20774
$315,000

2 beds

|

2 baths

|

1,195 sq ft

|

Condo

14040 NEW ACADIA LN 405, UPPER MARLBORO,...
Community: Cameron Grove
Venue at Winchelsea 3034 IVYHOUSE LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709
$599,018

3 beds

|

4 baths

|

2,151 sq ft

3034 IVYHOUSE LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Emerald Pointe 19418 PEARL DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$435,000

2 beds

|

2 baths

|

2,735 sq ft

19418 PEARL DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Four Seasons at Kent Island 111 MARSHGRASS WAY 41, CHESTER, MD, 2161..., Chester, MD 21619
$998,000

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

111 MARSHGRASS WAY 41, CHESTER, MD, 2161...
Legacy Woods 11730 LEGACY WOODS DR, FREDERICKSBURG, V..., Fredericksburg, VA 22407
$430,000

3 beds

|

2 baths

|

1,895 sq ft

11730 LEGACY WOODS DR, FREDERICKSBURG, V...
Community: Legacy Woods
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.
Leisure World® of Maryland 15311 BEAVERBROOK CT 90-3K, SILVER SPRIN..., Silver Spring, MD 20906
$239,000

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15311 BEAVERBROOK CT 90-3K, SILVER SPRIN...
The Village of Cinderberry 14 MULBERRY ST, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$339,000

2 beds

|

2 baths

|

1,591 sq ft

14 MULBERRY ST, GEORGETOWN, DE, 19947
Birchwood at Brambleton 23665 HAVELOCK WALK TER 406, ASHBURN, VA..., Ashburn, VA 20148
$480,000

1 beds

|

2 baths

|

1,229 sq ft

|

Condo

23665 HAVELOCK WALK TER 406, ASHBURN, VA...
Venue at Winchelsea 3314 ROOKERY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709
$601,272

3 beds

|

4 baths

|

2,151 sq ft

3314 ROOKERY LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
Signature Club at Greenview 10521 EDWARDIAN LN 142, NEW MARKET, MD, ..., New Market, MD 21774
$609,900

3 beds

|

3 baths

|

2,549 sq ft

|

Condo

10521 EDWARDIAN LN 142, NEW MARKET, MD, ...
Tanyard Shores 7605 CHERT CT, GLEN BURNIE, MD, 21060, Glen Burnie, MD 21060
$555,000

3 beds

|

4 baths

|

2,582 sq ft

7605 CHERT CT, GLEN BURNIE, MD, 21060
Community: Tanyard Shores
Celebrate 12 PENSACOLA ST, FREDERICKSBURG, VA, 224..., Fredericksburg, VA 22406
$447,000

2 beds

|

2 baths

|

1,502 sq ft

12 PENSACOLA ST, FREDERICKSBURG, VA, 224...
Community: Celebrate
Bishop's Landing 38652 LONGS CHAPEL LN, MILLVILLE, DE, 19..., Millville, DE 19967
$674,900

5 beds

|

3 baths

|

2,900 sq ft

38652 LONGS CHAPEL LN, MILLVILLE, DE, 19...
Community: Bishop's Landing
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Chesapeake 29692 MARIBEL LN, EASTON, MD, 21601, Easton, MD 21601
$505,000

3 beds

|

3 baths

|

2,342 sq ft

29692 MARIBEL LN, EASTON, MD, 21601
Community: Chesapeake
The Villages at Red Mill Pond 18680 GOLDEN SUNRISE PL, LEWES, DE, 1995..., Lewes, DE 19958
$799,900

5 beds

|

4 baths

|

3,902 sq ft

18680 GOLDEN SUNRISE PL, LEWES, DE, 1995...
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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© 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.
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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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