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
Willow Lawn Cottages 1818 KERSHAW LN, WINCHESTER, VA, 22601, Winchester, VA 22601
$382,500

2 beds

|

2 baths

|

1,271 sq ft

1818 KERSHAW LN, WINCHESTER, VA, 22601
Montebello 46440 BEARTOWN DR, STERLING, VA, 20164, Sterling, VA 20164
$915,000

3 beds

|

3 baths

|

2,251 sq ft

46440 BEARTOWN DR, STERLING, VA, 20164
Community: Montebello
Lexington Square 44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$818,236

3 beds

|

3 baths

|

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square
Lexington 7 44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$818,236

3 beds

|

3 baths

|

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington 7
Lexington 7 44506 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$837,656

3 beds

|

3 baths

|

2,969 sq ft

44506 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington 7
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Lexington Square 44506 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$837,656

3 beds

|

3 baths

|

2,969 sq ft

44506 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square
Four Seasons at Historic Virginia 4030 GREAT HARVEST CT, DUMFRIES, VA, 220..., Dumfries, VA 22025
$707,500

4 beds

|

3 baths

|

3,569 sq ft

4030 GREAT HARVEST CT, DUMFRIES, VA, 220...
The Crest of Alexandria 7922 ASHLAND DR, ALEXANDRIA, VA, 22315, Alexandria, VA 22315
$947,500

4 beds

|

5 baths

|

3,607 sq ft

7922 ASHLAND DR, ALEXANDRIA, VA, 22315
Four Seasons at Historic Virginia 3839 MULBERRY POINT CT, DUMFRIES, VA, 22..., Dumfries, VA 22025
$659,750

4 beds

|

3 baths

|

3,424 sq ft

3839 MULBERRY POINT CT, DUMFRIES, VA, 22...
Birchwood at Brambleton 23630 HAVELOCK WALK TER UNIT 218, ASHBUR..., Ashburn, VA 20148
$569,900

2 beds

|

2 baths

|

1,967 sq ft

|

Condo

23630 HAVELOCK WALK TER UNIT 218, ASHBUR...
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 13882 CINCH LN, GAINESVILLE, VA, 20155, Gainesville, VA 20155
$775,000

3 beds

|

4 baths

|

3,192 sq ft

13882 CINCH LN, GAINESVILLE, VA, 20155
Community: Heritage Hunt
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 1002, LEESBURG, ..., Leesburg, VA 20176
$375,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19375 CYPRESS RIDGE TER 1002, LEESBURG, ...
Regency at Dominion Valley 15218 BRIER CREEK DR, HAYMARKET, VA, 201..., Haymarket, VA 20169
$749,990

3 beds

|

3 baths

|

3,386 sq ft

15218 BRIER CREEK DR, HAYMARKET, VA, 201...
Four Seasons at Virginia Crossing 14035 MADRONA LN, WOODBRIDGE, VA, 22193, Woodbridge, VA 22193
$669,900

3 beds

|

3 baths

|

2,192 sq ft

14035 MADRONA LN, WOODBRIDGE, VA, 22193
Birchwood at Brambleton 23688 BOLTON CRESCENT TER APT 204, ASHBU..., Ashburn, VA 20148
$475,000

2 beds

|

2 baths

|

1,280 sq ft

|

Condo

23688 BOLTON CRESCENT TER APT 204, ASHBU...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Gatherings at Wellington 9202 CHARLESTON DR 307, MANASSAS, VA, 20..., Manassas, VA 20110
$421,000

3 beds

|

2 baths

|

2,006 sq ft

|

Condo

9202 CHARLESTON DR 307, MANASSAS, VA, 20...
Liberty Grove 8600 LIBERTY TRL UNIT 303, MANASSAS, VA,..., Manassas, VA 20110
$370,000

2 beds

|

3 baths

|

1,743 sq ft

|

Condo

8600 LIBERTY TRL UNIT 303, MANASSAS, VA,...
Community: Liberty Grove
Belmont Bay 680 WATERMANS DR APT 301, WOODBRIDGE, VA..., Woodbridge, VA 22191
$352,500

1 beds

|

2 baths

|

1,215 sq ft

|

Condo

680 WATERMANS DR APT 301, WOODBRIDGE, VA...
Community: Belmont Bay
Four Seasons at Virginia Crossing 3720 HAVERTILL LN UNIT 303, WOODBRIDGE, ..., Woodbridge, VA 22193
$475,000

2 beds

|

2 baths

|

1,706 sq ft

|

Condo

3720 HAVERTILL LN UNIT 303, WOODBRIDGE, ...
Four Seasons at Historic Virginia 17251 FOUR SEASONS DR, DUMFRIES, VA, 220..., Dumfries, VA 22025
$664,888

4 beds

|

4 baths

|

3,802 sq ft

17251 FOUR SEASONS DR, DUMFRIES, VA, 220...
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 Virginia Crossing 13970 ENGLEFIELD DR UNIT 303, WOODBRIDGE..., Woodbridge, VA 22193
$530,000

2 beds

|

2 baths

|

1,801 sq ft

|

Condo

13970 ENGLEFIELD DR UNIT 303, WOODBRIDGE...
The Atrium at MetroWest 2960 VADEN DR # 2-312, FAIRFAX, VA, 2203..., Fairfax, VA 22031
$788,980

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

2960 VADEN DR # 2-312, FAIRFAX, VA, 2203...
Heritage Hunt 6769 ARTHUR HILLS DR, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$849,900

4 beds

|

4 baths

|

5,410 sq ft

6769 ARTHUR HILLS DR, GAINESVILLE, VA, 2...
Community: Heritage Hunt
Liberty Grove 8600 LIBERTY TRL 102, MANASSAS, VA, 2011..., Manassas, VA 20110
$320,000

1 beds

|

2 baths

|

1,131 sq ft

|

Condo

8600 LIBERTY TRL 102, MANASSAS, VA, 2011...
Community: Liberty Grove
Trilogy® at Lake Frederick 102 BETONY CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$785,990

3 beds

|

3 baths

|

3,434 sq ft

102 BETONY CT, LAKE FREDERICK, VA, 22630
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Birchwood at Brambleton 42785 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$799,900

3 beds

|

3 baths

|

2,669 sq ft

42785 CUMULUS TER, ASHBURN, VA, 20148
Trilogy® at Lake Frederick 102 PHACELIA WAY, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$410,000

3 beds

|

4 baths

|

2,200 sq ft

102 PHACELIA WAY, LAKE FREDERICK, VA, 22...
Cadence at Lansdowne 18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176
$755,000

3 beds

|

3 baths

|

2,649 sq ft

18989 CORAL REEF SQ, LEESBURG, VA, 20176
Country Manor 21 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$194,921

2 beds

|

2 baths

|

1,322 sq ft

21 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
Penn National 6881 OLD COURSE RD, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$569,000

3 beds

|

3 baths

|

3,089 sq ft

6881 OLD COURSE RD, FAYETTEVILLE, PA, 17...
Community: Penn National
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.
Longstown Village 4117 WOODSPRING LN, YORK, PA, 17402, York, PA 17402
$225,000

2 beds

|

1 baths

|

1,104 sq ft

|

Condo

4117 WOODSPRING LN, YORK, PA, 17402
Community: Longstown Village
New North Pointe Condominiums 525 PARKVIEW LN # 113, HANOVER, PA, 1733..., Hanover, PA 17331
$289,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

525 PARKVIEW LN # 113, HANOVER, PA, 1733...
New Amblebrook 52 TULIP TREE WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$349,900

2 beds

|

2 baths

|

1,500 sq ft

52 TULIP TREE WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
Carmella 427 CARMELLA DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050
$599,000

3 beds

|

4 baths

|

3,848 sq ft

|

Condo

427 CARMELLA DR, MECHANICSBURG, PA, 1705...
Community: Carmella
New Roth's Farm Village 1302 VILLAGE DR, SPRING GROVE, PA, 17362, Spring Grove, PA 17362
$269,900

2 beds

|

2 baths

|

1,494 sq ft

|

Condo

1302 VILLAGE DR, SPRING GROVE, PA, 17362
Community: Roth's Farm Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
New Penn National 6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$339,900

4 beds

|

3 baths

|

1,536 sq ft

6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17...
Community: Penn National
New Longstown Village 4049 WOODSPRING LN # 4049, YORK, PA, 174..., York, PA 17402
$274,900

2 beds

|

2 baths

|

1,494 sq ft

|

Condo

4049 WOODSPRING LN # 4049, YORK, PA, 174...
Community: Longstown Village
Amblebrook 85 QUIET CREEK DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$615,000

2 beds

|

2 baths

|

2,220 sq ft

85 QUIET CREEK DR, GETTYSBURG, PA, 17325
Community: Amblebrook
Villas at Cattail 152 ST MICHAELS WAY, HANOVER, PA, 17331, Hanover, PA 17331
$400,000

3 beds

|

2 baths

|

2,165 sq ft

152 ST MICHAELS WAY, HANOVER, PA, 17331
Community: Villas at Cattail
Amblebrook 33 ROLLING HILLS WAY, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$450,000

2 beds

|

2 baths

|

1,852 sq ft

33 ROLLING HILLS WAY, GETTYSBURG, PA, 17...
Community: Amblebrook

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