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Maryland 55+ active adult communities & homes for sale - Page 5

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. Social Security…

Maryland offers the best of both worlds for retirees — proximity to Washington D.C. and Baltimore with suburban and rural communities just minutes away. Social Security benefits are exempt from state income tax, and the state is home to major academic health systems, including Johns Hopkins Medicine and the University of Maryland Medical System, both headquartered in Baltimore. According to the Maryland State Climatologist Office, Maryland has well-defined seasons, and winters in central and eastern Maryland fall between the colder Northeast and the milder South. Senior living communities in Maryland on 55places center on independent retirement living for active adults.

Maryland is home to 249 active adult communities, with homes ranging from the low $200Ks to over $1M and averaging about $518K. Leisure World of Maryland in Silver Spring is a gated community with more than 5,600 homes, according to the community. 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


254 communities near Maryland

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5 rating (1 review) Whitehall Gardens
$300ks - $400ks
Whitehall Gardens, Williamstown, NJ
New Construction | 55+ age-restricted | Built 2020 - present | 225 homes
The Courtyards at Waverly...
$300ks - $1Ms
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 homes
Village of Red Lion Creek
$200ks - $300ks
Village of Red Lion Creek, Bear, DE
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 85 homes
5 rating (1 review) Villas at Cattail Creek
$500ks - $1Ms
Villas at Cattail Creek, Glenwood, MD
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 93 homes
Fairway Overlook
$400ks - $500ks
Fairway Overlook, Elkridge, MD
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 25 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Gatherings at Potomac Sta...
$400ks - $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes
Little Falls Village
$300ks - $400ks
Little Falls Village, Wilmington, DE
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 107 homes
River Crossing at Spring ...
$300ks - $400ks
River Crossing at Spring ..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2014 - present | 63 homes
Whispering Woods
$300ks - $400ks
Whispering Woods, Middletown, DE
New and Resale | 55+ age-restricted | Built 2017 - present | 178 homes
Four Seasons at Saint Mar...
$300ks - $400ks
Four Seasons at Saint Mar..., Annapolis, MD
Resale Only | 55+ age-restricted | Built 2006 - 2011 | 166 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.
Hearthstone at Wedgewood
$300ks
Hearthstone at Wedgewood, Berlin, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2010 | 104 homes
Regency at Ashburn
$300ks - $800ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
Albert Courts
$100ks - $200ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes
Fieldstone Village
$200ks - $300ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes
Saintsbury Plaza
$300ks - $400ks
Saintsbury Plaza, Fairfax, VA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 111 homes
Boyers Retreat at Creeksi...
$400ks - $500ks
Boyers Retreat at Creeksi..., Bel Air, MD
New Construction | 55+ age-restricted | Built 2026 - present
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Hickory Crest
$400ks - $500ks
Hickory Crest, Columbia, MD
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 88 homes
The Reserve at New Windso...
$400ks
The Reserve at New Windso..., New Windsor, MD
Resale Only | 55+ age-restricted | Built 2016 - 2021 | 83 homes
Regency at Chancellorsvil...
$400ks - $500ks
Regency at Chancellorsvil..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2004 - 2019 | 225 homes
Gatherings at Ellicott Mi...
$300ks
Gatherings at Ellicott Mi..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2013 - 2018 | 127 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.
Regency at Creekside
$700ks - $800ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
The Villages at Broadland...
$400ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
Four Seasons at Abbey Cre...
$400ks - $500ks
Four Seasons at Abbey Cre..., Middletown, DE
55+ age-restricted | Built 2026 - present
Grace Woods 55+
$400ks
Grace Woods 55+, Aberdeen, MD
New Construction | 55+ age-restricted | Built 2025 - present | 96 homes
5 rating (1 review) Four Seasons at Vint Hill
$600ks
Four Seasons at Vint Hill, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes
Castlefield
$400ks
Castlefield, Manchester, MD
Resale Only | 55+ age-restricted | Built 2008 - 2022 | 53 homes
JerMae Estates
$300ks - $400ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Scot's Glen
$700ks - $800ks
Scot's Glen, Columbia, MD
Resale Only | 55+ age-restricted | Built 2006 - 2012 | 73 homes
Ellicott Meadows
$600ks - $700ks
Ellicott Meadows, Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 160 homes
The Signature at Broadlan...
$300ks - $400ks
The Signature at Broadlan..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 45 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.
Railroad Cottages
$700ks - $900ks
Railroad Cottages, Falls Church, VA
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 10 homes
4.5 rating (2 reviews) Southern Meadow
$100ks - $200ks
Southern Meadow, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 homes
5 rating (1 review) The Courtyards at Brandyw...
$400ks - $500ks
The Courtyards at Brandyw..., Wilmington, DE
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 184 homes
Montebello
$300ks - $600ks
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
Lexington Square
$800ks - $1Ms
Lexington Square, Ashburn, VA
New Construction | 55+ age-restricted | Built 2024 - present | 23 homes
The Village of Hershey Ru...
$200ks
The Village of Hershey Ru..., Wilmington, DE
Resale Only | 55+ age-restricted | Built 1990 - 1998 | 192 homes
Milltown Village
$500ks
Milltown Village, Wilmington, DE
Resale Only | 55+ age-restricted | Built 2008 - 2017 | 115 homes
Village of Long Creek
$400ks
Village of Long Creek, Newark, DE
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 100 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Cedar Bay
$200ks - $300ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 homes
The Village of Rocky Run
$400ks - $500ks
The Village of Rocky Run, Wilmington, DE
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 96 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.
Heritage Shores 89 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1..., Bridgeville, DE 19933
$429,900

4 beds

|

3 baths

|

2,042 sq ft

89 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1...
Community: Heritage Shores
Verona Woods 66 KALLISTO CT, DOVER, DE, 19901, Dover, DE 19901
$399,000

3 beds

|

2 baths

|

1,576 sq ft

66 KALLISTO CT, DOVER, DE, 19901
Community: Verona Woods
Twin Lake Villas 35031 MANSOURS DR, LOCUST GROVE, VA, 225..., Locust Grove, VA 22508
$395,000

3 beds

|

2 baths

|

1,369 sq ft

35031 MANSOURS DR, LOCUST GROVE, VA, 225...
Community: Twin Lake Villas
Noble's Pond 18 MATISSE PL, DOVER, DE, 19904, Dover, DE 19904
$610,000

3 beds

|

3 baths

|

2,727 sq ft

18 MATISSE PL, DOVER, DE, 19904
Community: Noble's Pond
Heritage Shores 1 HARLEQUIN LOOP, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$339,900

3 beds

|

2 baths

|

1,733 sq ft

1 HARLEQUIN LOOP, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Shores 85 EMILYS PINTAIL DR, BRIDGEVILLE, DE, 1..., Bridgeville, DE 19933
$314,900

2 beds

|

2 baths

|

1,574 sq ft

85 EMILYS PINTAIL DR, BRIDGEVILLE, DE, 1...
Community: Heritage Shores
New Montebello 6 COPLEY CIR, WEST BERLIN, NJ, 08091, West Berlin, NJ 08091
$819,000

4 beds

|

3 baths

|

2,871 sq ft

6 COPLEY CIR, WEST BERLIN, NJ, 08091
Community: Montebello
New Heritage Harbour 940 ASTERN WAY 101, ANNAPOLIS, MD, 21401, Annapolis, MD 21401
$450,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

940 ASTERN WAY 101, ANNAPOLIS, MD, 21401
Community: Heritage Harbour
New Auburn Meadows 799 VIRDIN DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$414,000

2 beds

|

2 baths

|

2,151 sq ft

799 VIRDIN DR, SMYRNA, DE, 19977
Community: Auburn Meadows
New Winifred Manor 2023 RUDY SERRA DR 3-B, ELDERSBURG, MD, ..., Eldersburg, MD 21784
$264,900

2 beds

|

2 baths

|

Condo

2023 RUDY SERRA DR 3-B, ELDERSBURG, MD, ...
Community: Winifred Manor
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.
New Heritage Harbour 2900 SHIPMASTER WAY 108, ANNAPOLIS, MD, ..., Annapolis, MD 21401
$355,000

2 beds

|

2 baths

|

1,048 sq ft

|

Condo

2900 SHIPMASTER WAY 108, ANNAPOLIS, MD, ...
Community: Heritage Harbour
New Venue at Winchelsea 3156 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709
$419,259

3 beds

|

3 baths

|

2,443 sq ft

3156 PETT LEVEL DR, MIDDLETOWN, DE, 1970...
Community: Venue at Winchelsea
New Cedar Ridge at Piney Orchard 8608 WANDERING FOX TRL 307, ODENTON, MD,..., Odenton, MD 21113
$519,000

3 beds

|

2 baths

|

1,900 sq ft

|

Condo

8608 WANDERING FOX TRL 307, ODENTON, MD,...
New Potomac Green 20579 ROSEWOOD MANOR SQ, ASHBURN, VA, 20..., Ashburn, VA 20147
$660,000

2 beds

|

2 baths

|

1,667 sq ft

20579 ROSEWOOD MANOR SQ, ASHBURN, VA, 20...
Community: Potomac Green
New Brittany Hills 346 CARLISLE DR, AVONDALE, PA, 19311, Avondale, PA 19311
$445,000

3 beds

|

3 baths

|

2,022 sq ft

346 CARLISLE DR, AVONDALE, PA, 19311
Community: Brittany Hills
New Cameron Grove 12900 FOX BOW DR 207, UPPER MARLBORO, MD..., Upper Marlboro, MD 20774
$275,000

2 beds

|

2 baths

|

928 sq ft

|

Condo

12900 FOX BOW DR 207, UPPER MARLBORO, MD...
Community: Cameron Grove
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
New Heritage Shores 12 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1..., Bridgeville, DE 19933
$428,000

3 beds

|

2 baths

|

1,902 sq ft

12 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1...
Community: Heritage Shores
New Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 219, LEESBURG, V..., Leesburg, VA 20176
$329,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19385 CYPRESS RIDGE TER 219, LEESBURG, V...
New Falls Run 20 DAYTON CIR, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$545,000

4 beds

|

4 baths

|

3,767 sq ft

20 DAYTON CIR, FREDERICKSBURG, VA, 22406
Community: Falls Run
New Leisure World® of Maryland 3111 BECKENHAM CT 254-A, SILVER SPRING, ..., Silver Spring, MD 20906
$289,900

2 beds

|

2 baths

|

998 sq ft

|

Condo

3111 BECKENHAM CT 254-A, SILVER SPRING, ...
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.
New Leisure World® of Maryland 3418 CHISWICK CT 46-E, SILVER SPRING, MD..., Silver Spring, MD 20906
$240,000

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

3418 CHISWICK CT 46-E, SILVER SPRING, MD...
New Riverbend 569 ARROWGRASS LN, NEW CASTLE, DE, 19720, New Castle, DE 19720
$399,990

3 beds

|

3 baths

|

2,278 sq ft

569 ARROWGRASS LN, NEW CASTLE, DE, 19720
Community: Riverbend
New Heritage Creek 216 HAY ST, MILTON, DE, 19968, Milton, DE 19968
$519,000

4 beds

|

4 baths

|

3,274 sq ft

216 HAY ST, MILTON, DE, 19968
Community: Heritage Creek
New Celebrate 35 MEARES WAY, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$649,500

3 beds

|

3 baths

|

3,006 sq ft

35 MEARES WAY, FREDERICKSBURG, VA, 22406
Community: Celebrate
New Bishop's Landing 38652 LONGS CHAPEL LN, MILLVILLE, DE, 19..., Millville, DE 19967
$675,000

5 beds

|

3 baths

|

2,988 sq ft

38652 LONGS CHAPEL LN, MILLVILLE, DE, 19...
Community: Bishop's Landing
New Carroll Vista 602 CLUBSIDE DR 404, TANEYTOWN, MD, 2178..., Taneytown, MD 21787
$350,000

2 beds

|

2 baths

|

1,548 sq ft

|

Condo

602 CLUBSIDE DR 404, TANEYTOWN, MD, 2178...
Community: Carroll Vista
New Parks Edge at Bayberry 0002 EDGAR DEGAS LN, MIDDLETOWN, DE, 197..., Middletown, DE 19709
$524,900

2 beds

|

2 baths

|

1,910 sq ft

0002 EDGAR DEGAS LN, MIDDLETOWN, DE, 197...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
New Venue at Winchelsea 005 EDGAR DEGAS LN, MIDDLETOWN, DE, 1970..., Middletown, DE 19709
$559,900

3 beds

|

2 baths

|

2,746 sq ft

005 EDGAR DEGAS LN, MIDDLETOWN, DE, 1970...
Community: Venue at Winchelsea
New
Cindy Certified
1650 SILVER HILL DR 1706, MCLEAN, VA, 22..., Mclean, VA 22102
$1,299,900

2 beds

|

2 baths

|

1,617 sq ft

|

Condo

1650 SILVER HILL DR 1706, MCLEAN, VA, 22...
New Parks Edge at Bayberry 0004 EDGAR DEGAS LN, MIDDLETOWN, DE, 197..., Middletown, DE 19709
$539,900

3 beds

|

2 baths

|

2,189 sq ft

0004 EDGAR DEGAS LN, MIDDLETOWN, DE, 197...
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.
New Parklands 10617 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$440,000

3 beds

|

3 baths

|

2,320 sq ft

10617 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
New Doroly Gardens 1705 BOTANICAL CT 13, SYKESVILLE, MD, 21..., Sykesville, MD 21784
$699,900

3 beds

|

3 baths

|

2,513 sq ft

|

Condo

1705 BOTANICAL CT 13, SYKESVILLE, MD, 21...
Community: Doroly Gardens
New Leisure World® of Maryland 3556 FISKE TER 146-B, SILVER SPRING, MD,..., Silver Spring, MD 20906
$349,000

2 beds

|

1 baths

|

850 sq ft

|

Condo

3556 FISKE TER 146-B, SILVER SPRING, MD,...
New
Cindy Certified
2907 BLEEKER ST 3-206, FAIRFAX, VA, 2203..., Fairfax, VA 22031
$650,000

2 beds

|

2 baths

|

1,506 sq ft

|

Condo

2907 BLEEKER ST 3-206, FAIRFAX, VA, 2203...
New Gerst Farm 9403 FOUNDERS LN, PERRY HALL, MD, 21128, Perry Hall, MD 21128
$679,990

4 beds

|

4 baths

|

3,337 sq ft

9403 FOUNDERS LN, PERRY HALL, MD, 21128
Community: Gerst Farm
New Auburn Meadows 129 DAVENPORT RD, SMYRNA, DE, 19977, Smyrna, DE 19977
$444,995

2 beds

|

2 baths

|

1,866 sq ft

129 DAVENPORT RD, SMYRNA, DE, 19977
Community: Auburn Meadows
New Holiday City at Monroe 521 BARBADOS DR, WILLIAMSTOWN, NJ, 08094, Williamstown, NJ 08094
$350,000

2 beds

|

2 baths

|

1,434 sq ft

521 BARBADOS DR, WILLIAMSTOWN, NJ, 08094
New Leisure World® of Maryland 3100 N LEISURE WORLD BLVD 919, SILVER SP..., Silver Spring, MD 20906
$280,000

2 beds

|

2 baths

|

1,035 sq ft

|

Condo

3100 N LEISURE WORLD BLVD 919, SILVER SP...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
New The Flats at Heathcote Village by Del Webb 5992 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$732,845

3 beds

|

3 baths

|

2,625 sq ft

5992 SUNSTONE LN, HAYMARKET, VA, 20169
New Keswick Villas 7734 HARLOW CIR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$406,506

3 beds

|

4 baths

|

2,189 sq ft

7734 HARLOW CIR, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
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: Nov 13, 2026.
This application does not include information on all of the properties available for sale at this time.

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