not an image

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

Middletown, MD 55+ active adult communities & homes for sale - Page 10

572 homes near Middletown

Sort by:

Relevance

Relevance

5 rating (1 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
4.3 rating (11 reviews) Amblebrook
$300ks - $700ks
Amblebrook, Gettysburg, PA
New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes
5 rating (2 reviews) Trilogy® at Lake Frederic...
- $900ks
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Willow Run
$500ks - $600ks
Willow Run, Winchester, VA
New Construction | 55+ age-restricted | 300 homes
Cameron Grove
$200ks - $400ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 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
The Flats at Northside
$600ks - $1Ms
The Flats at Northside, Potomac, MD
New Construction | Age-targeted | Built 2025 - present | 143 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 (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 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
Beechfield Manors
$200ks - $400ks
Beechfield Manors, Bowie, MD
New Construction | 55+ age-restricted | Built 2024 - present
Penn National
$100ks - $600ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
The Village at Cabin Bran...
$500ks
The Village at Cabin Bran..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2021 - present
The Atrium at MetroWest
$600ks - $700ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 homes
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 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 Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, MD
New Construction | 55+ age-restricted | Built 2026 - present
5 rating (1 reviews) Four Seasons at Historic ...
$400ks - $600ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
5 rating (1 reviews) Gatherings at Wellington
$300ks - $400ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes
5 rating (2 reviews) Potomac Green
$400ks - $800ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
Spring Valley Estates
$300ks - $400ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
5 rating (1 reviews) Carroll Vista
$200ks - $300ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 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) Two Rivers
$500ks - $700ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
Cedar Ridge at Piney Orch...
$200ks - $300ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
Winifred Manor
$200ks
Winifred Manor, Eldersburg, MD
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 152 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
Blue Ridge
$300ks - $400ks
Blue Ridge, Harrisburg, PA
New and Resale | Age-targeted | Built 2020 - present | 130 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Carroll's Creek
$300ks
Carroll's Creek, Gambrills, MD
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 162 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 homes
Signature Club at Greenvi...
$400ks - $500ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
Traditions of America at ...
$400ks - $600ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 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) Gatherings at Lyndwood
$300ks - $400ks
Gatherings at Lyndwood, Elkridge, MD
Resale Only | 55+ age-restricted | Built 2005 - 2008 | 216 homes
Four Seasons at Virginia ...
$400ks - $500ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 homes
Sagebrook
$300ks - $400ks
Sagebrook, Dover, PA
New and Resale | 55+ age-restricted | Built 2020 - present | 194 homes
The Crest of Alexandria
$400ks - $800ks
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
The Village at Freedom Hi...
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
5 rating (1 reviews) Crestwood Village
$200ks - $500ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
123...4
Penn National 6195 MERION DR, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222
$599,900

4 beds

|

3 baths

|

2,706 sq ft

6195 MERION DR, FAYETTEVILLE, PA, 17222
Community: Penn National
Amblebrook 321 HIGHLAND WAY 160, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$449,900

2 beds

|

2 baths

|

1,409 sq ft

321 HIGHLAND WAY 160, GETTYSBURG, PA, 17...
Community: Amblebrook
Regency at Dominion Valley 15110 HEATHER MILL LN 402, HAYMARKET, VA..., Haymarket, VA 20169
$465,000

2 beds

|

2 baths

|

1,551 sq ft

|

Condo

15110 HEATHER MILL LN 402, HAYMARKET, VA...
Leisure World® of Maryland 15011 CANDOVER CT 280-D, SILVER SPRING, ..., Silver Spring, MD 20906
$259,000

2 beds

|

3 baths

|

1,359 sq ft

|

Condo

15011 CANDOVER CT 280-D, SILVER SPRING, ...
Leisure World® of Maryland 3703 LIVERPOOL PL 37-A, SILVER SPRING, M..., Silver Spring, MD 20906
$399,900

2 beds

|

2 baths

|

1,100 sq ft

3703 LIVERPOOL PL 37-A, SILVER SPRING, M...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Birchwood at Brambleton 23631 HAVELOCK WALK TER 302, ASHBURN, VA..., Ashburn, VA 20148
$449,900

2 beds

|

2 baths

|

1,244 sq ft

|

Condo

23631 HAVELOCK WALK TER 302, ASHBURN, VA...
Rosehill Manor Villas 19604 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$374,900

2 beds

|

2 baths

|

1,767 sq ft

19604 LAVENDER LN, HAGERSTOWN, MD, 21742
Willow Run 121 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602
$609,990

4 beds

|

3 baths

|

2,818 sq ft

121 SCENTED ROSE WAY, WINCHESTER, VA, 22...
Community: Willow Run
Willow Run 117 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602
$599,990

4 beds

|

3 baths

|

2,865 sq ft

117 SCENTED ROSE WAY, WINCHESTER, VA, 22...
Community: Willow Run
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.
Trilogy® at Lake Frederick 109 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$425,000

3 beds

|

4 baths

|

2,304 sq ft

109 BAYHILL TER, LAKE FREDERICK, VA, 226...
The Flats at Northside 1135 POLARIS RD EDINBURGH 82, POTOMAC, M..., Potomac, MD 20854
$1,349,900

4 beds

|

3 baths

|

2,840 sq ft

1135 POLARIS RD EDINBURGH 82, POTOMAC, M...
The Flats at Northside 1135 POLARIS RD CAMBRIDGE 78, POTOMAC, M..., Potomac, MD 20854
$999,900

4 beds

|

3 baths

|

2,350 sq ft

1135 POLARIS RD CAMBRIDGE 78, POTOMAC, M...
Carroll Vista 413 CLUBSIDE DR 299, TANEYTOWN, MD, 2178..., Taneytown, MD 21787
$365,000

2 beds

|

2 baths

|

1,697 sq ft

|

Condo

413 CLUBSIDE DR 299, TANEYTOWN, MD, 2178...
Community: Carroll Vista
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Cadence at Lansdowne 18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176
$739,800

3 beds

|

3 baths

|

2,649 sq ft

18989 CORAL REEF SQ, LEESBURG, VA, 20176
Amblebrook 395 QUIET CREEK DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$798,900

2 beds

|

3 baths

|

2,809 sq ft

395 QUIET CREEK DR, GETTYSBURG, PA, 1732...
Community: Amblebrook
Cameron Grove 14040 NEW ACADIA LN 406, UPPER MARLBORO,..., Upper Marlboro, MD 20774
$324,500

2 beds

|

2 baths

|

1,280 sq ft

|

Condo

14040 NEW ACADIA LN 406, UPPER MARLBORO,...
Community: Cameron Grove
The Atrium at MetroWest 2960 VADEN DR 2N-602, FAIRFAX, VA, 22031, Fairfax, VA 22031
$824,500

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

2960 VADEN DR 2N-602, FAIRFAX, VA, 22031
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.
Gatherings at Cabin Branch 13516 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$545,000

3 beds

|

3 baths

|

1,590 sq ft

13516 GOLDENEYE CIR, CLARKSBURG, MD, 208...
The Village at Cabin Branch 13516 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$545,000

3 beds

|

3 baths

|

1,590 sq ft

13516 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Leisure World® of Maryland 15115 INTERLACHEN DR 3-812, SILVER SPRIN..., Silver Spring, MD 20906
$249,900

2 beds

|

2 baths

|

1,225 sq ft

|

Condo

15115 INTERLACHEN DR 3-812, SILVER SPRIN...
Cameron Grove 14000 NEW ACADIA LN 106, UPPER MARLBORO,..., Upper Marlboro, MD 20774
$260,000

1 beds

|

1 baths

|

1,020 sq ft

|

Condo

14000 NEW ACADIA LN 106, UPPER MARLBORO,...
Community: Cameron Grove
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 203, SILVER SP..., Silver Spring, MD 20906
$325,000

2 beds

|

2 baths

|

1,495 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 203, SILVER SP...
Leisure World® of Maryland 3506 FISKE TER 153-A, SILVER SPRING, MD,..., Silver Spring, MD 20906
$325,000

2 beds

|

1 baths

|

960 sq ft

|

Condo

3506 FISKE TER 153-A, SILVER SPRING, MD,...
Country Manor 95 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$209,900

2 beds

|

2 baths

|

1,544 sq ft

95 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
The Reserve at New Windsor 2845 UNION SQUARE RD 66, NEW WINDSOR, MD..., New Windsor, MD 21776
$450,000

3 beds

|

3 baths

|

2,264 sq ft

|

Condo

2845 UNION SQUARE RD 66, NEW WINDSOR, MD...
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 3200 N LEISURE WORLD BLVD 1007, SILVER S..., Silver Spring, MD 20906
$299,900

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 1007, SILVER S...
Amblebrook 63 RUSTIC WOOD DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$384,900

2 beds

|

2 baths

|

1,514 sq ft

63 RUSTIC WOOD DR, GETTYSBURG, PA, 17325
Community: Amblebrook
Trilogy® at Lake Frederick 117 PINTAIL WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$857,900

4 beds

|

4 baths

|

4,804 sq ft

117 PINTAIL WAY, LAKE FREDERICK, VA, 226...
Snowden Overlook 8781 ENDLESS OCEAN WAY 58, COLUMBIA, MD,..., Columbia, MD 21045
$699,000

3 beds

|

5 baths

|

4,565 sq ft

|

Condo

8781 ENDLESS OCEAN WAY 58, COLUMBIA, MD,...
Community: Snowden Overlook
Leisure World® of Maryland 3661 S LEISURE WORLD BLVD 15-K, SILVER S..., Silver Spring, MD 20906
$235,000

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

3661 S LEISURE WORLD BLVD 15-K, SILVER S...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Eden Brook 2602 CLARION CT 404, ODENTON, MD, 21113, Odenton, MD 21113
$369,900

2 beds

|

2 baths

|

1,603 sq ft

|

Condo

2602 CLARION CT 404, ODENTON, MD, 21113
Community: Eden Brook
Fairway Overlook 5936 DEBORAH JEAN DR, ELKRIDGE, MD, 2107..., Elkridge, MD 21075
$919,990

4 beds

|

3 baths

|

2,784 sq ft

5936 DEBORAH JEAN DR, ELKRIDGE, MD, 2107...
Community: Fairway Overlook
Trilogy® at Lake Frederick 109 TUTELO LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$599,999

2 beds

|

3 baths

|

3,505 sq ft

109 TUTELO LN, LAKE FREDERICK, VA, 22630
Spring Hill 8970 FASCINATION CT 111, LORTON, VA, 220..., Lorton, VA 22079
$475,000

2 beds

|

2 baths

|

1,367 sq ft

|

Condo

8970 FASCINATION CT 111, LORTON, VA, 220...
Community: Spring Hill
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.
Birchwood at Brambleton 23630 HAVELOCK WALK TER 305, ASHBURN, VA..., Ashburn, VA 20148
$435,000

2 beds

|

2 baths

|

1,060 sq ft

|

Condo

23630 HAVELOCK WALK TER 305, ASHBURN, VA...
Rosehill Manor Villas 13354 SNAPDRAGON WAY, HAGERSTOWN, MD, 21..., Hagerstown, MD 21742
$379,990

3 beds

|

2 baths

|

1,466 sq ft

13354 SNAPDRAGON WAY, HAGERSTOWN, MD, 21...
Rosehill Manor Villas 13352 SNAPDRAGON WAY, HAGERSTOWN, MD, 21..., Hagerstown, MD 21742
$397,646

3 beds

|

2 baths

|

1,687 sq ft

13352 SNAPDRAGON WAY, HAGERSTOWN, MD, 21...
Winchester Landing 116 MAURY, WINCHESTER, VA, 22602, Winchester, VA 22602
$395,000

3 beds

|

3 baths

|

1,630 sq ft

116 MAURY, WINCHESTER, VA, 22602
Community: Winchester Landing
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Crawfords Ridge 620 CRAWFORDS RIDGE RD, ODENTON, MD, 211..., Odenton, MD 21113
$749,900

4 beds

|

4 baths

|

2,808 sq ft

620 CRAWFORDS RIDGE RD, ODENTON, MD, 211...
Community: Crawfords Ridge
Amblebrook 134 GENTLE SLOPE WAY, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$680,000

2 beds

|

2 baths

|

2,811 sq ft

134 GENTLE SLOPE 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
572 homes
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.
© 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: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top