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Maryland 55+ active adult communities & homes for sale

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


246 communities 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) Noble's Pond
$200ks - $300ks
Noble's Pond, Dover, DE
New and Resale | 55+ age-restricted | Built 2007 - present | 800 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
The Flats at Heathcote Vi...
$300ks - $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction | 55+ age-restricted | Built 2026 - present | 500 homes
Parklands
$300ks - $500ks
Parklands, White Plains, MD
New Construction | 55+ age-restricted | Built 2025 - present | 586 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
1.7 rating (3 reviews) Silver Woods
$400ks - $500ks
Silver Woods, Ocean View, DE
New and Resale | Age-targeted | Built 2005 - present | 111 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Traditions at Whitehall
$400ks - $500ks
Traditions at Whitehall, Middletown, DE
New Construction | 55+ age-restricted | Built 2019 - present | 250 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 Village at Cabin Bran...
$500ks
The Village at Cabin Bran..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2021 - present
The Village of Cinderberr...
$200ks - $300ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 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.
Element at Mill Creek
$400ks - $600ks
Element at Mill Creek, Annapolis, MD
New Construction | 55+ age-restricted | Built 2022 - present | 140 homes
The Flats at Northside
$600ks - $1Ms
The Flats at Northside, Potomac, MD
New Construction | Age-targeted | Built 2025 - present | 143 homes
Chesapeake
$300ks - $400ks
Chesapeake, Easton, MD
Resale Only | 55+ age-restricted | Built 2002 - 2011 | 452 homes
Holiday City at Monroe
$200ks
Holiday City at Monroe, Williamstown, NJ
Resale Only | 55+ age-restricted | Built 1989 - 2007 | 682 homes
The Villas at The Preserv...
$400ks
The Villas at The Preserv..., Townsend, DE
New Construction | 55+ age-restricted | Built 2017 - present | 144 homes
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 homes
Four Seasons at Hatteras ...
$400ks - $500ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 homes
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
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
5 rating (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
Bay Bridge Cove
$300ks - $500ks
Bay Bridge Cove, Stevensville, MD
Resale Only | 55+ age-restricted | Built 2016 - 2022 | 273 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.
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 (1 reviews) Keswick Villas
$300ks - $500ks
Keswick Villas, Spotsylvania, VA
New Construction | 55+ age-restricted | Built 2020 - present | 84 homes
The Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
Spring Valley Estates
$300ks - $400ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 homes
Four Seasons at Baymont F...
$400ks - $500ks
Four Seasons at Baymont F..., Middletown, DE
New Construction | Age-targeted | Built 2019 - present | 288 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
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, 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
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Independence
$400ks - $800ks
Independence, Millsboro, DE
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 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.
New Whitehall Gardens 3566 PROVIDENCE CT, WILLIAMSTOWN, NJ, 08..., Williamstown, NJ 08094
$490,000

3 beds

|

2 baths

|

2,028 sq ft

3566 PROVIDENCE CT, WILLIAMSTOWN, NJ, 08...
Community: Whitehall Gardens
The Parke at Ocean Pines 6 EASTON AVE, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811
$409,000

2 beds

|

2 baths

|

1,704 sq ft

6 EASTON AVE, OCEAN PINES, MD, 21811
Heritage Hunt 7065 HERITAGE HUNT DR 108, GAINESVILLE, ..., Gainesville, VA 20155
$399,900

2 beds

|

2 baths

|

1,292 sq ft

|

Condo

7065 HERITAGE HUNT DR 108, GAINESVILLE, ...
Community: Heritage Hunt
Auburn Meadows 101 HANOVER AVE, SMYRNA, DE, 19977, Smyrna, DE 19977
$475,000

3 beds

|

3 baths

|

2,361 sq ft

101 HANOVER AVE, SMYRNA, DE, 19977
Community: Auburn Meadows
Heritage Shores 134 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$314,900

2 beds

|

2 baths

|

1,320 sq ft

134 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
Four Seasons at Kent Island 2000 HERONS NEST WAY 401, CHESTER, MD, 2..., Chester, MD 21619
$700,000

3 beds

|

3 baths

|

2,602 sq ft

|

Condo

2000 HERONS NEST WAY 401, CHESTER, MD, 2...
The Villages at Red Mill Pond 14692 PLEASANT POND WAY, LEWES, DE, 1995..., Lewes, DE 19958
$575,000

3 beds

|

2 baths

|

2,185 sq ft

14692 PLEASANT POND WAY, LEWES, DE, 1995...
Four Seasons at Kent Island 132 WHEELHOUSE WAY 11, CHESTER, MD, 2161..., Chester, MD 21619
$700,000

2 beds

|

3 baths

|

2,003 sq ft

|

Condo

132 WHEELHOUSE WAY 11, CHESTER, MD, 2161...
Twin Lake Villas 34889 MANSOURS DR, LOCUST GROVE, VA, 225..., Locust Grove, VA 22508
$418,000

3 beds

|

2 baths

|

1,369 sq ft

34889 MANSOURS DR, LOCUST GROVE, VA, 225...
Community: Twin Lake Villas
Heritage Shores 110 WINGED FOOT DR, BRIDGEVILLE, DE, 199..., Bridgeville, DE 19933
$529,000

4 beds

|

3 baths

|

2,598 sq ft

110 WINGED FOOT DR, BRIDGEVILLE, DE, 199...
Community: Heritage Shores
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 Millville 16 TORRESDALE ST, MILLVILLE, NJ, 08332, Millville, NJ 08332
$309,000

2 beds

|

2 baths

|

1,464 sq ft

16 TORRESDALE ST, MILLVILLE, NJ, 08332
Verona Woods 76 BALTHASAR DR, DOVER, DE, 19901, Dover, DE 19901
$424,000

3 beds

|

2 baths

|

1,704 sq ft

76 BALTHASAR DR, DOVER, DE, 19901
Community: Verona Woods
New Cameron Grove 1 ROSEBUD CT, UPPER MARLBORO, MD, 20774, Upper Marlboro, MD 20774
$400,000

2 beds

|

2 baths

|

1,306 sq ft

1 ROSEBUD CT, UPPER MARLBORO, MD, 20774
Community: Cameron Grove
New 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
New 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
New 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...
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
New 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
New Village of Cecil Woods 73 WOODS WAY, ELKTON, MD, 21921, Elkton, MD 21921
$125,000

2 beds

|

2 baths

|

1,176 sq ft

73 WOODS WAY, ELKTON, MD, 21921
New Venue at Winchelsea 3315 ROOKERY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709
$579,250

3 beds

|

3 baths

|

2,065 sq ft

3315 ROOKERY LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
New Venue at Winchelsea 2213 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709
$442,509

3 beds

|

3 baths

|

2,443 sq ft

2213 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...
Community: Venue at Winchelsea
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 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...
New 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
New 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...
New 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
New 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
New 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
New 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
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
New Element at Mill Creek 78 OLD MILL BOTTOM RD 209, ANNAPOLIS, MD..., Annapolis, MD 21409
$455,000

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

78 OLD MILL BOTTOM RD 209, ANNAPOLIS, MD...
New Chesapeake 29692 MARIBEL LN, EASTON, MD, 21601, Easton, MD 21601
$515,000

3 beds

|

3 baths

|

2,342 sq ft

29692 MARIBEL LN, EASTON, MD, 21601
Community: Chesapeake
New 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
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 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
New Heritage Hunt 13972 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$775,000

4 beds

|

4 baths

|

3,256 sq ft

13972 REAL QUITE CT, GAINESVILLE, VA, 20...
Community: Heritage Hunt
New 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...
New Four Seasons at Kent Island 102 BOATSWAIN WAY 2943, CHESTER, MD, 216..., Chester, MD 21619
$929,990

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

102 BOATSWAIN WAY 2943, CHESTER, MD, 216...
New Four Seasons at Kent Island 102 BOATSWAIN WAY 2932, CHESTER, MD, 216..., Chester, MD 21619
$829,990

2 beds

|

3 baths

|

1,900 sq ft

|

Condo

102 BOATSWAIN WAY 2932, CHESTER, MD, 216...
New Silver Woods 319 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$441,990

3 beds

|

3 baths

|

2,088 sq ft

319 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
New 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
New 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
Want to learn more about 55+ communities in Maryland? 55places can help!
Questions? Call us: (888) 625-4885
New Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER 1105, LEESBURG, ..., Leesburg, VA 20176
$375,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19365 CYPRESS RIDGE TER 1105, LEESBURG, ...
New Silver Woods 315 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$465,990

3 beds

|

3 baths

|

2,267 sq ft

315 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.



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