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Maryland 55+ active adult communities & homes for sale - Page 9

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


1,011 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.
5 rating (2 reviews) Heritage Shores
$300ks - $500ks
Heritage Shores, Bridgeville, DE
New and Resale | 55+ age-restricted | Built 2004 - present | 1,816 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
The Flats at Heathcote Vi...
$300ks - $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction | 55+ age-restricted | Built 2026 - present | 500 homes
3.1 rating (7 reviews) Celebrate
$300ks - $600ks
Celebrate, Fredericksburg, VA
New and Resale | 55+ age-restricted | Built 2008 - present | 1,100 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
Parklands
$300ks - $500ks
Parklands, White Plains, MD
New Construction | 55+ age-restricted | Built 2025 - present | 586 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
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
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
Chesapeake
$300ks - $400ks
Chesapeake, Easton, MD
Resale Only | 55+ age-restricted | Built 2002 - 2011 | 452 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
5 rating (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
Holiday City at Monroe
$200ks
Holiday City at Monroe, Williamstown, NJ
Resale Only | 55+ age-restricted | Built 1989 - 2007 | 682 homes
The Flats at Northside
$600ks - $1Ms
The Flats at Northside, Potomac, MD
New Construction | Age-targeted | Built 2025 - present | 143 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
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Four Seasons at Hatteras ...
$400ks - $500ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 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.
Sundance Club
$500ks - $800ks
Sundance Club, Frankford, DE
New Construction | 55+ age-restricted | Built 2026 - present | 180 homes
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
Four Seasons at Baymont F...
$400ks - $500ks
Four Seasons at Baymont F..., Middletown, DE
New Construction | Age-targeted | Built 2019 - present | 288 homes
The Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
Liberty West
$400ks
Liberty West, Georgetown, DE
New Construction | Age-targeted | Built 2025 - present | 181 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
Longacre Village
$300ks
Longacre Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 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
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (1 reviews) Keswick Villas
$300ks - $500ks
Keswick Villas, Spotsylvania, VA
New Construction | 55+ age-restricted | Built 2020 - present | 84 homes
Venue at Winchelsea
$400ks - $600ks
Venue at Winchelsea, Middletown, DE
New Construction | 55+ age-restricted | Built 2024 - present | 336 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 Preserve at Weatherby 602 VAN BUREN CT, SWEDESBORO, NJ, 08085, Swedesboro, NJ 08085
$649,990

3 beds

|

3 baths

|

2,387 sq ft

602 VAN BUREN CT, SWEDESBORO, NJ, 08085
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 905, LEESBURG, V..., Leesburg, VA 20176
$349,000

1 beds

|

2 baths

|

874 sq ft

|

Condo

19355 CYPRESS RIDGE TER 905, LEESBURG, V...
Tanyard Shores 7605 CHERT CT, GLEN BURNIE, MD, 21060, Glen Burnie, MD 21060
$565,000

3 beds

|

4 baths

|

2,582 sq ft

7605 CHERT CT, GLEN BURNIE, MD, 21060
Community: Tanyard Shores
Four Seasons at Historic Virginia 3941 SOLSTICE LN, DUMFRIES, VA, 22025, Dumfries, VA 22025
$700,000

4 beds

|

3 baths

|

3,600 sq ft

3941 SOLSTICE LN, DUMFRIES, VA, 22025
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
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
The Flats at Northside 1121 FORTUNE TER 6, POTOMAC, MD, 20854, Potomac, MD 20854
$874,990

2 beds

|

2 baths

|

1,566 sq ft

|

Condo

1121 FORTUNE TER 6, POTOMAC, MD, 20854
The Flats at Northside 1121 FORTUNE TER 2, POTOMAC, MD, 20854, Potomac, MD 20854
$884,990

2 beds

|

2 baths

|

1,534 sq ft

|

Condo

1121 FORTUNE TER 2, POTOMAC, MD, 20854
Silver Woods 309 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$487,990

3 beds

|

3 baths

|

2,088 sq ft

309 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Bishop's Landing 38652 LONGS CHAPEL LN, MILLVILLE, DE, 19..., Millville, DE 19967
$699,900

5 beds

|

3 baths

|

2,900 sq ft

38652 LONGS CHAPEL LN, MILLVILLE, DE, 19...
Community: Bishop's Landing
Element at Mill Creek 78 OLD MILL BOTTOM RD 209, ANNAPOLIS, MD..., Annapolis, MD 21409
$439,500

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

78 OLD MILL BOTTOM RD 209, ANNAPOLIS, MD...
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.
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...
The Flats at Northside 1121 FORTUNE TER 1, POTOMAC, MD, 20854, Potomac, MD 20854
$849,990

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

1121 FORTUNE TER 1, POTOMAC, MD, 20854
Silver Woods 321 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$460,990

3 beds

|

3 baths

|

2,088 sq ft

321 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Heritage Hunt 13972 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$745,000

4 beds

|

4 baths

|

3,256 sq ft

13972 REAL QUITE CT, GAINESVILLE, VA, 20...
Community: Heritage Hunt
The Courtyards at Waverly Woods 2415 ANDERSON HILL ST, MARRIOTTSVILLE, M..., Marriottsville, MD 21104
$925,000

3 beds

|

3 baths

|

5,380 sq ft

|

Condo

2415 ANDERSON HILL ST, MARRIOTTSVILLE, M...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Four Seasons at Kent Island 102 BOATSWAIN WAY 2943, CHESTER, MD, 216..., Chester, MD 21619
$919,990

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

102 BOATSWAIN WAY 2943, CHESTER, MD, 216...
Four Seasons at Kent Island 102 BOATSWAIN WAY 2932, CHESTER, MD, 216..., Chester, MD 21619
$819,990

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

102 BOATSWAIN WAY 2932, CHESTER, MD, 216...
Silver Woods 317 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$451,990

3 beds

|

3 baths

|

2,088 sq ft

317 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 333 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$435,990

3 beds

|

3 baths

|

2,088 sq ft

333 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver 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.
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER 1105, LEESBURG, ..., Leesburg, VA 20176
$365,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19365 CYPRESS RIDGE TER 1105, LEESBURG, ...
Silver Woods 315 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$439,990

3 beds

|

3 baths

|

2,267 sq ft

315 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 329 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$447,990

3 beds

|

3 baths

|

2,267 sq ft

329 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Leisure World® of Maryland 15300 BEAVERBROOK CT 88-2K, SILVER SPRIN..., Silver Spring, MD 20906
$264,000

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15300 BEAVERBROOK CT 88-2K, SILVER SPRIN...
Celebrate 9 LUDINGTON LN, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$439,000

2 beds

|

2 baths

|

1,476 sq ft

9 LUDINGTON LN, FREDERICKSBURG, VA, 2240...
Community: Celebrate
The Gatherings at Lakeview Community 546 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136
$349,990

3 beds

|

3 baths

|

1,569 sq ft

|

Condo

546 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
The Gatherings at Lakeview Community 548 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136
$474,990

3 beds

|

3 baths

|

2,475 sq ft

|

Condo

548 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Chesapeake 7466 KAREN AVE, EASTON, MD, 21601, Easton, MD 21601
$510,000

3 beds

|

3 baths

|

2,342 sq ft

7466 KAREN AVE, EASTON, MD, 21601
Community: Chesapeake
Tanyard Shores 812 TEACHER MITCHELL RD, GLEN BURNIE, MD..., Glen Burnie, MD 21060
$530,000

4 beds

|

4 baths

|

2,000 sq ft

812 TEACHER MITCHELL RD, GLEN BURNIE, MD...
Community: Tanyard Shores
Lansdowne Woods of Virginia 19370 MAGNOLIA GROVE SQ L04, LEESBURG, V..., Leesburg, VA 20176
$589,900

2 beds

|

2 baths

|

1,708 sq ft

|

Condo

19370 MAGNOLIA GROVE SQ L04, LEESBURG, 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.
Whitehall Gardens 3700 CASTLETON DR, WILLIAMSTOWN, NJ, 080..., Williamstown, NJ 08094
$475,000

3 beds

|

2 baths

3700 CASTLETON DR, WILLIAMSTOWN, NJ, 080...
Community: Whitehall Gardens
Two Rivers 2446 HEATH ASTER CT, ODENTON, MD, 21113, Odenton, MD 21113
$799,000

4 beds

|

3 baths

|

1,802 sq ft

2446 HEATH ASTER CT, ODENTON, MD, 21113
Community: Two Rivers
Keswick Villas 7734 HARLOW CIR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$468,550

3 beds

|

4 baths

|

2,189 sq ft

7734 HARLOW CIR, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
Keswick Villas 7742 HARLOW CIR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$461,000

3 beds

|

4 baths

|

2,189 sq ft

7742 HARLOW CIR, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
JerMae Estates 5 GEOLEY CT, THURMONT, MD, 21788, Thurmont, MD 21788
$474,999

4 beds

|

3 baths

|

2,038 sq ft

5 GEOLEY CT, THURMONT, MD, 21788
Community: JerMae Estates
Stirling Glen 228 KIPPEN DR, WILLIAMSTOWN, NJ, 08094, Williamstown, NJ 08094
$525,000

3 beds

|

3 baths

|

2,564 sq ft

228 KIPPEN DR, WILLIAMSTOWN, NJ, 08094
Community: Stirling Glen
Falls Run 22 CHANTILLY PL, FREDERICKSBURG, VA, 224..., Fredericksburg, VA 22406
$488,800

4 beds

|

3 baths

|

2,541 sq ft

22 CHANTILLY PL, FREDERICKSBURG, VA, 224...
Community: Falls Run
Ovations at Elk View 207 HENDRICKSON LN, WEST GROVE, PA, 1939..., West Grove, PA 19390
$515,000

3 beds

|

3 baths

|

2,874 sq ft

207 HENDRICKSON LN, WEST GROVE, PA, 1939...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Chesapeake 29689 LYONS DR, EASTON, MD, 21601, Easton, MD 21601
$475,000

2 beds

|

2 baths

|

1,878 sq ft

29689 LYONS DR, EASTON, MD, 21601
Community: Chesapeake
Cindy Certified
100 CAMDEN CIR, LA PLATA, MD, 20646, La Plata, MD 20646
$369,950

2 beds

|

2 baths

|

1,550 sq ft

100 CAMDEN CIR, LA PLATA, MD, 20646
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: Aug 23, 2026.
This application does not include information on all of the properties available for sale at this time.

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