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Maryland 55+ active adult communities & homes for sale - Page 8

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 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
Four Seasons at Historic Virginia 17451 FOUR SEASONS DR, DUMFRIES, VA, 220..., Dumfries, VA 22025
$724,900

4 beds

|

3 baths

|

3,872 sq ft

17451 FOUR SEASONS DR, DUMFRIES, VA, 220...
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
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 408, LEESBURG, V..., Leesburg, VA 20176
$379,999

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

19355 CYPRESS RIDGE TER 408, LEESBURG, V...
Leisure World® of Maryland 14601 DEERHURST TER, SILVER SPRING, MD, ..., Silver Spring, MD 20906
$425,000

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

14601 DEERHURST TER, SILVER SPRING, MD, ...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Leisure World® of Maryland 15107 INTERLACHEN DR 2-621, SILVER SPRIN..., Silver Spring, MD 20906
$139,500

2 beds

|

2 baths

|

990 sq ft

|

Condo

15107 INTERLACHEN DR 2-621, SILVER SPRIN...
The Courtyards at Waverly Woods 2420 WALKING JANELLE WAY, MARRIOTTSVILLE..., Marriottsville, MD 21104
$700,000

4 beds

|

4 baths

|

3,612 sq ft

2420 WALKING JANELLE WAY, MARRIOTTSVILLE...
Chesapeake 29833 HILLARY AVE, EASTON, MD, 21601, Easton, MD 21601
$495,000

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
$559,900

3 beds

|

3 baths

|

2,613 sq ft

111 WEATHERBY LN, GLASSBORO, NJ, 08028
Crestwood Village 5679 BARBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703
$414,900

2 beds

|

2 baths

|

1,148 sq ft

5679 BARBERRY CT, FREDERICK, MD, 21703
Community: Crestwood Village
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 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
Montebello 21630 HAWKSBILL HIGH CIR 406, STERLING, ..., Sterling, VA 20164
$734,999

3 beds

|

2 baths

|

1,825 sq ft

|

Condo

21630 HAWKSBILL HIGH CIR 406, STERLING, ...
Community: Montebello
Village of Eastridge 197 LUPINE DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$525,000

3 beds

|

4 baths

|

3,331 sq ft

197 LUPINE DR, SMYRNA, DE, 19977
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...
Barley Woods 6603 GOLDEN PHEASANT RUN, FREDERICKSBURG..., Fredericksburg, VA 22407
$465,000

3 beds

|

2 baths

|

1,904 sq ft

6603 GOLDEN PHEASANT RUN, FREDERICKSBURG...
Community: Barley Woods
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
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
Greenvale Mews 186 GREENVALE MEWS DR 11, WESTMINSTER, M..., Westminster, MD 21157
$489,500

3 beds

|

3 baths

|

2,416 sq ft

|

Condo

186 GREENVALE MEWS DR 11, WESTMINSTER, M...
Community: Greenvale Mews
The Enclave at Ellicott Station 2608 QUEENSLAND DR, ELLICOTT CITY, MD, 2..., Ellicott City, MD 21042
$677,000

4 beds

|

4 baths

|

3,425 sq ft

2608 QUEENSLAND DR, ELLICOTT CITY, MD, 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 Woodlands of Urbana 3226 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704
$625,000

3 beds

|

4 baths

|

2,226 sq ft

3226 STARLIGHT ST, FREDERICK, MD, 21704
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
Longacre Village 108 N RED HVN, DOVER, DE, 19901, Dover, DE 19901
$465,000

3 beds

|

2 baths

|

2,176 sq ft

108 N RED HVN, DOVER, DE, 19901
Community: Longacre Village
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
$595,000

3 beds

|

4 baths

|

2,151 sq ft

3034 IVYHOUSE LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
Celebrate 35 BATTERY POINT DR, FREDERICKSBURG, VA,..., Fredericksburg, VA 22406
$599,000

3 beds

|

3 baths

|

3,026 sq ft

35 BATTERY POINT DR, FREDERICKSBURG, VA,...
Community: Celebrate
Four Seasons at Baymont Farms 112 AUSTRIAN PINE CT, MIDDLETOWN, DE, 19..., Middletown, DE 19709
$639,990

3 beds

|

4 baths

|

2,441 sq ft

112 AUSTRIAN PINE CT, MIDDLETOWN, DE, 19...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Four Seasons at Baymont Farms 13 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1..., Middletown, DE 19709
$624,900

3 beds

|

3 baths

|

1,859 sq ft

13 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1...
The Courtyards at Waverly Woods 2121 JOHN STUART RD E, MARRIOTTSVILLE, M..., Marriottsville, MD 21104
$369,000

2 beds

|

2 baths

|

1,436 sq ft

|

Condo

2121 JOHN STUART RD E, MARRIOTTSVILLE, M...
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
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 111 MARSHGRASS WAY 41, CHESTER, MD, 2161..., Chester, MD 21619
$998,000

3 beds

|

3 baths

|

Condo

111 MARSHGRASS WAY 41, CHESTER, MD, 2161...
Legacy Woods 11730 LEGACY WOODS DR, FREDERICKSBURG, V..., Fredericksburg, VA 22407
$440,000

3 beds

|

2 baths

|

1,895 sq ft

11730 LEGACY WOODS DR, FREDERICKSBURG, V...
Community: Legacy Woods
Leisure World® of Maryland 3498 GLENEAGLES DR 79-F, SILVER SPRING, ..., Silver Spring, MD 20906
$215,000

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

3498 GLENEAGLES DR 79-F, SILVER SPRING, ...
Leisure World® of Maryland 15311 BEAVERBROOK CT 90-3K, SILVER SPRIN..., Silver Spring, MD 20906
$245,000

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15311 BEAVERBROOK CT 90-3K, SILVER SPRIN...
Saintsbury Plaza 2907 SAINTSBURY PLZ 404, FAIRFAX, VA, 22..., Fairfax, VA 22031
$249,990

2 beds

|

1 baths

|

892 sq ft

|

Condo

2907 SAINTSBURY PLZ 404, FAIRFAX, VA, 22...
Community: Saintsbury Plaza
The Village of Cinderberry 14 MULBERRY ST, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$342,000

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
$499,900

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
$593,250

3 beds

|

4 baths

|

2,151 sq ft

3314 ROOKERY 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
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, ...
Leisure World® of Maryland 15100 INTERLACHEN DR 4-124, SILVER SPRIN..., Silver Spring, MD 20906
$239,000

2 beds

|

2 baths

|

1,195 sq ft

15100 INTERLACHEN DR 4-124, SILVER SPRIN...
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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