Call us at (240) 663-8229 to learn more about active adult communities near Middletown

Middletown, MD 55+ active adult communities & homes for sale

489 homes near Middletown

Sort by:

Relevance

Relevance

No reviews yet The Village at Foxfield
$300Ks - $500Ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
5 rating (1 reviews) Leisure World® of Marylan...
<$100k - $500Ks
Leisure World® of Marylan..., Silver Spring, MD
Resale Only | 55+ age-restricted | Built 1966 - 2009 | 5,600 homes
4.3 rating (11 reviews) Amblebrook
$300Ks - $1Ms
Amblebrook, Gettysburg, PA
New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes
5 rating (3 reviews) Heritage Hunt
$600Ks - $800Ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
5 rating (2 reviews) Potomac Green
$700Ks - $800Ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
5 rating (31 reviews) Lansdowne Woods of Virgin...
$300Ks - $500Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes
No reviews yet Penn National
$200Ks - $800Ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
5 rating (2 reviews) Trilogy® at Lake Frederic...
$400Ks - $1Ms
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
5 rating (1 reviews) Regency at Dominion Valle...
$400Ks - $800Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 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 (1 reviews) Four Seasons at Historic ...
$600Ks - $700Ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes
5 rating (1 reviews) Two Rivers
$500Ks - $800Ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
No reviews yet Cameron Grove
$300Ks - $400Ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 homes
5 rating (2 reviews) Central Parke at Victoria...
$300Ks - $600Ks
Central Parke at Victoria..., Laurel, MD
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes
No reviews yet The Woodlands of Urbana
$600Ks - $700Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
5 rating (1 reviews) Crestwood Village
$300Ks - $300Ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
No reviews yet Traditions of America at ...
$400Ks - $500Ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 homes
No reviews yet Carter's Mill
$400Ks - $700Ks
Carter's Mill, Haymarket, VA
New Construction | 55+ age-restricted | Built 2020 - present | 480 homes
3 rating (2 reviews) Dunbarton
$600Ks - $600Ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
No reviews yet The Courtyards at Waverly...
$300Ks - $600Ks
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 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 (1 reviews) Carroll Vista
$300Ks - $500Ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 homes
No reviews yet Cedar Ridge at Piney Orch...
$300Ks - $400Ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
No reviews yet Montebello
$600Ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
No reviews yet Village Crest
$400Ks - $600Ks
Village Crest, Ellicott City, MD
New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 homes
No reviews yet Courtyards at Waverly Woo...
$300Ks - $400Ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 383 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
5 rating (1 reviews) Snowden Overlook
$400Ks - $700Ks
Snowden Overlook, Columbia, MD
Resale Only | 55+ age-restricted | Built 2005 - 2010 | 350 homes
No reviews yet Creek View
$100Ks - $200Ks
Creek View, Carlisle, PA
New and Resale | 55+ age-restricted | Built 2004 - present | 305 homes
No reviews yet Longstown Village
$100Ks - $200Ks
Longstown Village, York, PA
Resale Only | Age-targeted | Built 1997 - 2000 | 304 homes
No reviews yet Heritage at St. Charles
$400Ks - $500Ks
Heritage at St. Charles, White Plains, MD
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 300 homes
No reviews yet The Villages At Woodholme
$400Ks - $500Ks
The Villages At Woodholme, Baltimore, MD
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 286 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.
No reviews yet Spring Hill
$500Ks - $800Ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
No reviews yet The Enclave at Ellicott H...
$400Ks - $400Ks
The Enclave at Ellicott H..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 280 homes
No reviews yet Regency at Ashburn
$500Ks - $600Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
No reviews yet Emerald Pointe
$300Ks - $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
No reviews yet The Crest of Alexandria
$900Ks - $900Ks
The Crest of Alexandria, Alexandria, VA
New and Resale | 55+ age-restricted | Built 2017 - present | 250 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
No reviews yet Colonial Charles
$400Ks - $400Ks
Colonial Charles, Waldorf, MD
Resale Only | 55+ age-restricted | Built 2006 - 2018 | 240 homes
No reviews yet River Ridge
$600Ks - $600Ks
River Ridge, Woodbridge, VA
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes
No reviews yet Signature Club at Greenvi...
$400Ks - $900Ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
No reviews yet Eden Brook
$300Ks - $300Ks
Eden Brook, Odenton, MD
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 224 homes
No reviews yet Roth's Farm Village
$200Ks - $200Ks
Roth's Farm Village, Spring Grove, PA
New and Resale | 55+ age-restricted | Built 2006 - present | 224 homes
New Crestwood Village 7043 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703
$339,999

2 beds

|

2 baths

|

1,225 sq ft

7043 BASSWOOD RD, FREDERICK, MD, 21703
Community: Crestwood Village
Two Rivers 1240 BEAVER TREE DR, ODENTON, MD, 21113, Odenton, MD 21113
$749,900

3 beds

|

4 baths

|

3,144 sq ft

1240 BEAVER TREE DR, ODENTON, MD, 21113
Community: Two Rivers
New Leisure World® of Maryland 15418 BRAMBLEWOOD DR # 20-C, SILVER SPRI..., Silver Spring, MD 20906
$525,000

3 beds

|

2 baths

|

1,251 sq ft

|

Condo

15418 BRAMBLEWOOD DR # 20-C, SILVER SPRI...
Cameron Grove 13502 LEESBURG PL, UPPER MARLBORO, MD, 2..., Upper Marlboro, MD 20774
$435,000

2 beds

|

2 baths

|

1,518 sq ft

13502 LEESBURG PL, UPPER MARLBORO, MD, 2...
Community: Cameron Grove
Leisure World® of Maryland 3005 S LEISURE WORLD BLVD APT 702, SILVE..., Silver Spring, MD 20906
$289,900

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

3005 S LEISURE WORLD BLVD APT 702, SILVE...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Two Rivers 1508 ORCHARD GRASS CT, ODENTON, MD, 2111..., Odenton, MD 21113
$824,000

4 beds

|

3 baths

|

3,384 sq ft

1508 ORCHARD GRASS CT, ODENTON, MD, 2111...
Community: Two Rivers
New Leisure World® of Maryland 15101 INTERLACHEN DR 1-123, SILVER SPRIN..., Silver Spring, MD 20906
$234,900

2 beds

|

2 baths

|

1,225 sq ft

|

Condo

15101 INTERLACHEN DR 1-123, SILVER SPRIN...
Leisure World® of Maryland 15524 PRINCE FREDERICK WAY # 118-A, SILV..., Silver Spring, MD 20906
$499,000

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

15524 PRINCE FREDERICK WAY # 118-A, SILV...
Heritage at St. Charles 4909 KESWICK CT, WHITE PLAINS, MD, 20695, White Plains, MD 20695
$499,000

4 beds

|

3 baths

|

2,081 sq ft

4909 KESWICK CT, WHITE PLAINS, MD, 20695
New Leisure World® of Maryland 3320 CHISWICK CT 61-2B, SILVER SPRING, M..., Silver Spring, MD 20906
$149,000

2 beds

|

1 baths

|

1,035 sq ft

|

Condo

3320 CHISWICK CT 61-2B, SILVER SPRING, M...
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.
Leisure World® of Maryland 15011 CANDOVER CT # 280-D, SILVER SPRING..., Silver Spring, MD 20906
$165,000

2 beds

|

3 baths

|

1,359 sq ft

|

Condo

15011 CANDOVER CT # 280-D, SILVER SPRING...
Leisure World® of Maryland 3500 FOREST EDGE DR 15-2F, SILVER SPRING..., Silver Spring, MD 20906
$185,000

1 beds

|

2 baths

|

946 sq ft

3500 FOREST EDGE DR 15-2F, SILVER SPRING...
The Courtyards at Waverly Woods 2231 JOHN GRAVEL RD L, MARRIOTTSVILLE, M..., Marriottsville, MD 21104
$397,000

2 beds

|

2 baths

|

1,438 sq ft

|

Condo

2231 JOHN GRAVEL RD L, MARRIOTTSVILLE, M...
Courtyards at Waverly Woods East 11100 CHAMBERS CT K, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$420,000

2 beds

|

2 baths

|

1,610 sq ft

|

Condo

11100 CHAMBERS CT K, WOODSTOCK, MD, 2116...
Leisure World® of Maryland 3352 CHISWICK CT 57-3E, SILVER SPRING, M..., Silver Spring, MD 20906
$103,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

3352 CHISWICK CT 57-3E, SILVER SPRING, M...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
New Gatherings at Cabin Branch 13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$499,000

3 beds

|

3 baths

|

1,590 sq ft

13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
New The Village at Cabin Branch 13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$499,000

3 beds

|

3 baths

|

1,590 sq ft

13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Gatherings at Lyndwood 6150 SHADYWOOD RD UNIT 401, ELKRIDGE, MD..., Elkridge, MD 21075
$425,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

6150 SHADYWOOD RD UNIT 401, ELKRIDGE, MD...
Ellicott's Retreat 8960 CARLS CT A, ELLICOTT CITY, MD, 2104..., Ellicott City, MD 21043
$430,000

2 beds

|

2 baths

|

1,502 sq ft

8960 CARLS CT A, ELLICOTT CITY, MD, 2104...
Community: Ellicott's Retreat
New Eden Brook 2605 CLARION CT APT 303, ODENTON, MD, 21..., Odenton, MD 21113
$370,000

2 beds

|

2 baths

|

1,611 sq ft

|

Condo

2605 CLARION CT APT 303, ODENTON, MD, 21...
Community: Eden Brook
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.
Snowden Overlook 8879 WARM GRANITE DR # 27, COLUMBIA, MD,..., Columbia, MD 21045
$650,000

4 beds

|

5 baths

|

4,196 sq ft

|

Condo

8879 WARM GRANITE DR # 27, COLUMBIA, MD,...
Community: Snowden Overlook
Hawthorne Greene 6 GRAMBY CT, LA PLATA, MD, 20646, La Plata, MD 20646
$425,000

2 beds

|

2 baths

|

1,549 sq ft

6 GRAMBY CT, LA PLATA, MD, 20646
Community: Hawthorne Greene
Carroll Vista 102 BUTTERFLY DR # 55, TANEYTOWN, MD, 21..., Taneytown, MD 21787
$379,900

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

102 BUTTERFLY DR # 55, TANEYTOWN, MD, 21...
Community: Carroll Vista
Leisure World® of Maryland 15115 INTERLACHEN DR 3-815, SILVER SPRIN..., Silver Spring, MD 20906
$230,000

2 beds

|

2 baths

|

1,115 sq ft

|

Condo

15115 INTERLACHEN DR 3-815, SILVER SPRIN...
Leisure World® of Maryland 15107 INTERLACHEN DR 2-119, SILVER SPRIN..., Silver Spring, MD 20906
$235,000

2 beds

|

2 baths

|

950 sq ft

|

Condo

15107 INTERLACHEN DR 2-119, SILVER SPRIN...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Leisure World® of Maryland 15300 BEAVERBROOK CT 88-2E, SILVER SPRIN..., Silver Spring, MD 20906
$289,000

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15300 BEAVERBROOK CT 88-2E, SILVER SPRIN...
Leisure World® of Maryland 2901 S LEISURE WORLD BLVD 304, SILVER SP..., Silver Spring, MD 20906
$299,900

2 beds

|

2 baths

|

1,229 sq ft

|

Condo

2901 S LEISURE WORLD BLVD 304, SILVER SP...
Heritage at St. Charles 11257 YELLOWSTONE CT, WHITE PLAINS, MD, ..., White Plains, MD 20695
$479,990

3 beds

|

2 baths

|

2,235 sq ft

11257 YELLOWSTONE CT, WHITE PLAINS, MD, ...
The Enclave at Ellicott Hills 2520 KENSINGTON GDNS UNIT 401, ELLICOTT ..., Ellicott City, MD 21043
$400,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

2520 KENSINGTON GDNS UNIT 401, ELLICOTT ...
Hawthorne Greene 9 GRAMBY CT, LA PLATA, MD, 20646, La Plata, MD 20646
$509,000

2 beds

|

2 baths

|

1,983 sq ft

9 GRAMBY CT, LA PLATA, MD, 20646
Community: Hawthorne Greene
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.
Winifred Manor 2010 RUDY SERRA DR C, SYKESVILLE, MD, 21..., Sykesville, MD 21784
$275,000

2 beds

|

2 baths

|

1,080 sq ft

|

Condo

2010 RUDY SERRA DR C, SYKESVILLE, MD, 21...
Community: Winifred Manor
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 115, SILVER SP..., Silver Spring, MD 20906
$300,000

3 beds

|

2 baths

|

1,489 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 115, SILVER SP...
Villas at Cattail Creek 15124 PLAYERS WAY 7, GLENWOOD, MD, 21738, Glenwood, MD 21738
$609,000

4 beds

|

4 baths

|

4,297 sq ft

|

Condo

15124 PLAYERS WAY 7, GLENWOOD, MD, 21738
New Crestwood Village 5765 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703
$335,000

2 beds

|

1 baths

|

1,113 sq ft

5765 BOX ELDER CT, FREDERICK, MD, 21703
Community: Crestwood Village
Cameron Grove 13006 BRICE CT, UPPER MARLBORO, MD, 2077..., Upper Marlboro, MD 20774
$485,000

3 beds

|

3 baths

|

2,601 sq ft

13006 BRICE CT, UPPER MARLBORO, MD, 2077...
Community: Cameron Grove
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
The Villages At Woodholme 8325 MEADOWSWEET RD # 8325, BALTIMORE, M..., Baltimore, MD 21208
$500,000

3 beds

|

3 baths

|

3,144 sq ft

|

Condo

8325 MEADOWSWEET RD # 8325, BALTIMORE, M...
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 918, SILVER SP..., Silver Spring, MD 20906
$309,500

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 918, SILVER SP...
Leisure World® of Maryland 15310 PINE ORCHARD DR 84-3K, SILVER SPRI..., Silver Spring, MD 20906
$269,000

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15310 PINE ORCHARD DR 84-3K, SILVER SPRI...
Leisure World® of Maryland 15211 ELKRIDGE WAY 94-2F, SILVER SPRING,..., Silver Spring, MD 20906
$264,875

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15211 ELKRIDGE WAY 94-2F, SILVER SPRING,...
Leisure World® of Maryland 15300 WALLBROOK CT 47-2C, SILVER SPRING,..., Silver Spring, MD 20906
$220,000

2 beds

|

2 baths

|

1,237 sq ft

|

Condo

15300 WALLBROOK CT 47-2C, SILVER SPRING,...

Frequently Asked Questions


Want more information about active adult communities around Middletown?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Middletown?

Call us: (240) 663-8229
489 homes near Middletown
Remove Boundaries ×
Map Satellite

Reinmlsx

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.
© 2025 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: Oct 24, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top