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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. 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 Village at Cabin Branch 13516 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$499,900

3 beds

|

3 baths

|

1,590 sq ft

13516 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Gatherings at Cabin Branch 13516 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$499,900

3 beds

|

3 baths

|

1,590 sq ft

13516 GOLDENEYE CIR, CLARKSBURG, MD, 208...
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...
Four Seasons at Millville 121 COTTAGE ST, MILLVILLE, NJ, 08332, Millville, NJ 08332
$339,900

2 beds

|

2 baths

|

1,594 sq ft

121 COTTAGE ST, MILLVILLE, NJ, 08332
Leisure World® of Maryland 15101 INTERLACHEN DR 1-1002, SILVER SPRI..., Silver Spring, MD 20906
$159,000

1 beds

|

1 baths

|

860 sq ft

|

Condo

15101 INTERLACHEN DR 1-1002, SILVER SPRI...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Leisure World® of Maryland 15430 BRAMBLEWOOD DR 22-B, SILVER SPRING..., Silver Spring, MD 20906
$459,000

2 beds

|

2 baths

|

1,346 sq ft

|

Condo

15430 BRAMBLEWOOD DR 22-B, SILVER SPRING...
Virginia Heritage at Lee's Parke 9722 BIG BETHEL RD, FREDERICKSBURG, VA, ..., Fredericksburg, VA 22407
$529,900

4 beds

|

3 baths

|

2,618 sq ft

9722 BIG BETHEL RD, FREDERICKSBURG, VA, ...
Brittany Hills 4 N HENLEY DR, AVONDALE, PA, 19311, Avondale, PA 19311
$499,999

3 beds

|

3 baths

|

3,300 sq ft

4 N HENLEY DR, AVONDALE, PA, 19311
Community: Brittany Hills
Four Seasons at Historic Virginia 3770 CHINA GRV, DUMFRIES, VA, 22025, Dumfries, VA 22025
$679,950

4 beds

|

3 baths

|

4,055 sq ft

3770 CHINA GRV, DUMFRIES, VA, 22025
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER 615, LEESBURG, V..., Leesburg, VA 20176
$485,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19365 CYPRESS RIDGE TER 615, 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.
Venue at Winchelsea 3164 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709
$445,559

3 beds

|

3 baths

|

2,443 sq ft

3164 PETT LEVEL DR, MIDDLETOWN, DE, 1970...
Community: Venue at Winchelsea
The Parke at Ocean Pines 6 FEDERAL HL, BERLIN, MD, 21811, Berlin, MD 21811
$499,900

3 beds

|

3 baths

|

2,422 sq ft

6 FEDERAL HL, BERLIN, MD, 21811
The Village of Cinderberry 3 BAYBERRY ST 2, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$314,999

2 beds

|

2 baths

|

1,518 sq ft

3 BAYBERRY ST 2, GEORGETOWN, DE, 19947
Summerlake 11317 SAVANNAH DR, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22407
$367,500

2 beds

|

2 baths

|

1,570 sq ft

11317 SAVANNAH DR, FREDERICKSBURG, VA, 2...
Community: Summerlake
Holiday City at Monroe 526 TRINIDAD BLVD, WILLIAMSTOWN, NJ, 080..., Williamstown, NJ 08094
$315,000

2 beds

|

2 baths

|

1,260 sq ft

526 TRINIDAD BLVD, WILLIAMSTOWN, NJ, 080...
Four Seasons at Kent Island 201 SWITCHGRASS WAY 34, CHESTER, MD, 216..., Chester, MD 21619
$859,500

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

201 SWITCHGRASS WAY 34, CHESTER, MD, 216...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Foxfield 1638 BOXWOOD RD, GARNET VALLEY, PA, 1906..., Garnet Valley, PA 19060
$485,000

2 beds

|

2 baths

|

2,047 sq ft

1638 BOXWOOD RD, GARNET VALLEY, PA, 1906...
Community: Foxfield
Leisure World® of Maryland 3250 GLENEAGLES DR 104-B, SILVER SPRING,..., Silver Spring, MD 20906
$225,000

2 beds

|

3 baths

|

1,445 sq ft

|

Condo

3250 GLENEAGLES DR 104-B, SILVER SPRING,...
Virginia Heritage at Lee's Parke 10006 WOFFORD WAY, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22407
$625,000

4 beds

|

3 baths

|

4,081 sq ft

10006 WOFFORD WAY, FREDERICKSBURG, VA, 2...
Four Seasons at Saint Margaret's 1501 BROADNECK PL 303, ANNAPOLIS, MD, 21..., Annapolis, MD 21409
$392,500

2 beds

|

2 baths

|

1,235 sq ft

|

Condo

1501 BROADNECK PL 303, ANNAPOLIS, MD, 21...
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 320 BAYBERRY DR, CHESTER, MD, 21619, Chester, MD 21619
$897,750

3 beds

|

2 baths

|

2,331 sq ft

320 BAYBERRY DR, CHESTER, MD, 21619
Noble's Pond 334 CARPER DR, DOVER, DE, 19904, Dover, DE 19904
$384,900

3 beds

|

3 baths

|

2,142 sq ft

334 CARPER DR, DOVER, DE, 19904
Community: Noble's Pond
Liberty Place 40 LIBERTY RD T, SYKESVILLE, MD, 21784, Sykesville, MD 21784
$320,000

2 beds

|

2 baths

|

1,186 sq ft

|

Condo

40 LIBERTY RD T, SYKESVILLE, MD, 21784
Community: Liberty Place
Noble's Pond 20 LACEY LN, DOVER, DE, 19904, Dover, DE 19904
$449,990

3 beds

|

3 baths

|

2,386 sq ft

20 LACEY LN, DOVER, DE, 19904
Community: Noble's Pond
Cindy Certified
3 STATIONMASTER ST 201, LEESBURG, VA, 20..., Leesburg, VA 20175
$980,000

2 beds

|

2 baths

|

1,818 sq ft

|

Condo

3 STATIONMASTER ST 201, LEESBURG, VA, 20...
Cascades at Embrey Mill 223 SMOKEBUSH DR, STAFFORD, VA, 22554, Stafford, VA 22554
$669,000

4 beds

|

4 baths

|

3,591 sq ft

|

Condo

223 SMOKEBUSH DR, STAFFORD, VA, 22554
Spicer Estates 419 WOODRUFF TRL, MULLICA HILL, NJ, 0806..., Mullica Hill, NJ 08062
$370,000

2 beds

|

2 baths

|

1,435 sq ft

419 WOODRUFF TRL, MULLICA HILL, NJ, 0806...
Community: Spicer Estates
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
McKinsey Park 600 MCKINSEY PARK DR 502, SEVERNA PARK, ..., Severna Park, MD 21146
$420,000

2 beds

|

2 baths

|

1,231 sq ft

|

Condo

600 MCKINSEY PARK DR 502, SEVERNA PARK, ...
Community: McKinsey Park
Symphony Village 214 HARMONY WAY, CENTREVILLE, MD, 21617, Centreville, MD 21617
$439,900

3 beds

|

2 baths

|

1,972 sq ft

214 HARMONY WAY, CENTREVILLE, MD, 21617
Community: Symphony Village
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 7, HAYMARKET, VA, 201..., Haymarket, VA 20169
$474,990

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

5800 MOONSTONE WAY 7, HAYMARKET, VA, 201...
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 6, HAYMARKET, VA, 201..., Haymarket, VA 20169
$374,990

1 beds

|

2 baths

|

995 sq ft

|

Condo

5800 MOONSTONE WAY 6, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 5, HAYMARKET, VA, 201..., Haymarket, VA 20169
$609,990

3 beds

|

2 baths

|

1,850 sq ft

|

Condo

5800 MOONSTONE WAY 5, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 4, HAYMARKET, VA, 201..., Haymarket, VA 20169
$549,990

2 beds

|

2 baths

|

1,520 sq ft

|

Condo

5800 MOONSTONE WAY 4, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 3, HAYMARKET, VA, 201..., Haymarket, VA 20169
$599,990

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

5800 MOONSTONE WAY 3, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 2, HAYMARKET, VA, 201..., Haymarket, VA 20169
$424,990

2 beds

|

2 baths

|

1,345 sq ft

|

Condo

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 1, HAYMARKET, VA, 201..., Haymarket, VA 20169
$494,990

2 beds

|

2 baths

|

1,475 sq ft

|

Condo

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201...
Four Seasons at Kent Island 123 FLYCATCHER WAY, CHESTER, MD, 21619, Chester, MD 21619
$1,100,000

3 beds

|

3 baths

|

2,789 sq ft

123 FLYCATCHER WAY, CHESTER, MD, 21619
Four Seasons at Kent Island 117 FLYCATCHER WAY, CHESTER, MD, 21619, Chester, MD 21619
$1,200,000

3 beds

|

4 baths

|

2,930 sq ft

117 FLYCATCHER WAY, CHESTER, MD, 21619
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Four Seasons at Kent Island 111 FLYCATCHER WAY, CHESTER, MD, 21619, Chester, MD 21619
$1,200,000

5 beds

|

5 baths

|

3,225 sq ft

111 FLYCATCHER WAY, CHESTER, MD, 21619
Carroll's Creek 1405 WIGEON WAY 101, GAMBRILLS, MD, 2105..., Gambrills, MD 21054
$455,000

3 beds

|

2 baths

|

1,777 sq ft

|

Condo

1405 WIGEON WAY 101, GAMBRILLS, MD, 2105...
Community: Carroll's Creek
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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