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Middletown, MD 55+ active adult communities & homes for sale - Page 7
141 communities near Middletown
582 homes near Middletown
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3 rating (2 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...]()
$300ks
- $1Ms
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
$300ks
- $500ks
Parklands, White Plains, MD
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
586 homes
$300ks
- $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2026 - present
|
500 homes
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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
5 rating (3 reviews)
![Heritage Hunt]()
$400ks
- $600ks
Heritage Hunt, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2009
|
1,863 homes
$200ks
- $400ks
Cameron Grove, Upper Marlboro, MD
Resale Only
|
55+ age-restricted
|
Built 1999 - 2013
|
740 homes
$100ks
- $600ks
Penn National, Fayetteville, PA
New and Resale
|
Age-targeted
|
Built 1968 - present
|
1,100 homes
$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.
$500ks
The Village at Cabin Bran..., Clarksburg, MD
New Construction
|
55+ age-restricted
|
Built 2021 - present
5 rating (1 reviews)
![Two Rivers]()
$500ks
- $700ks
Two Rivers, Odenton, MD
New and Resale
|
55+ age-restricted
|
Built 2015 - present
|
800 homes
$500ks
- $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2025
|
565 homes
$400ks
- $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
135 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
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$300ks
- $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
122 homes
$300ks
- $400ks
Spring Valley Estates, Waynesboro, PA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
140 homes
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
177 homes
$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.
$200ks
- $400ks
Beechfield Manors, Bowie, MD
New Construction
|
55+ age-restricted
|
Built 2024 - present
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
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2024
|
74 homes
$400ks
- $500ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
185 homes
$300ks
- $500ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$700ks
- $800ks
Bloomfields 55+, Frederick, MD
New Construction
|
55+ age-restricted
|
Built 2026 - present
$300ks
- $400ks
Sagebrook, Dover, PA
New and Resale
|
55+ age-restricted
|
Built 2020 - present
|
194 homes
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5 rating (1 reviews)
![Snowden Overlook]()
$300ks
- $600ks
Snowden Overlook, Columbia, MD
Resale Only
|
55+ age-restricted
|
Built 2005 - 2010
|
350 homes
$400ks
- $800ks
The Crest of Alexandria, Alexandria, VA
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
250 homes
$600ks
- $700ks
The Atrium at MetroWest, Fairfax, VA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
206 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)
![Central Parke at Victoria...]()
$300ks
- $500ks
Central Parke at Victoria..., Laurel, MD
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
609 homes
$300ks
Carroll's Creek, Gambrills, MD
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
162 homes
3 rating (2 reviews)
![Dunbarton]()
$300ks
- $500ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 homes
5 rating (1 reviews)
![Willow Lawn Cottages]()
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2004
|
120 homes
$500ks
- $1Ms
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
5 rating (2 reviews)
![Potomac Green]()
$400ks
- $800ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 homes
5 rating (1 reviews)
![Carroll Vista]()
$300ks
Carroll Vista, Taneytown, MD
Resale Only
|
55+ age-restricted
|
Built 2004 - 2017
|
453 homes
$300ks
- $400ks
Winchester Landing, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2023 - 2025
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(240) 663-8229
$300ks
- $600ks
Cortland Park, Mechanicsburg, PA
New and Resale
|
55+ age-restricted
|
Built 2020 - present
|
104 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.
Leisure World® of Maryland
![3365 S LEISURE WORLD BLVD 95-2D, SILVER ..., Silver Spring, MD 20906]()
1 beds
|1 baths
|990 sq ft
|Condo
3365 S LEISURE WORLD BLVD 95-2D, SILVER ...
Community: Leisure World® of Maryland
MLS MDMC2235684 • Long & Foster Real Estate, Inc....
Lansdowne Woods of Virginia
![19370 MAGNOLIA GROVE SQ 403, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,168 sq ft
|Condo
19370 MAGNOLIA GROVE SQ 403, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2126658 • Samson Properties, Andrew M Nor...
Heritage Hunt
![13452 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2121320 • CENTURY 21 New Millennium, Sand...
Gatherings at Lyndwood
![6150 SHADYWOOD RD 401, ELKRIDGE, MD, 210..., Elkridge, MD 21075]()
2 beds
|2 baths
|1,500 sq ft
|Condo
6150 SHADYWOOD RD 401, ELKRIDGE, MD, 210...
Community: Gatherings at Lyndwood
MLS MDHW2068428 • Winning Edge, Jim Bim
Heritage Hunt
![6943 CUMBERSTONE PL, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2121230 • CENTURY 21 New Millennium, Mich...
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Cadence at Lansdowne
![19006 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176]()
3 beds
|5 baths
|3,679 sq ft
19006 CORAL REEF SQ, LEESBURG, VA, 20176
Community: Cadence at Lansdowne
MLS VALO2125364 • Hunt Country Sotheby's Internat...
Trilogy® at Lake Frederick
![145 COWBIRD, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
3 beds
|2 baths
|1,771 sq ft
145 COWBIRD, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2042204 • Keller Williams Realty, Karl Ac...
The Village at Cabin Branch
![13240 PETREL ST 5306, CLARKSBURG, MD, 20..., Clarksburg, MD 20871]()
3 beds
|2 baths
|1,887 sq ft
|Condo
13240 PETREL ST 5306, CLARKSBURG, MD, 20...
Community: The Village at Cabin Branch
MLS MDMC2237608 • Keller Williams Realty Centre, ...
Gatherings at Cabin Branch
![13240 PETREL ST 5306, CLARKSBURG, MD, 20..., Clarksburg, MD 20871]()
3 beds
|2 baths
|1,887 sq ft
|Condo
13240 PETREL ST 5306, CLARKSBURG, MD, 20...
Community: Gatherings at Cabin Branch
MLS MDMC2237608 • Keller Williams Realty Centre, ...
Gatherings at Cabin Branch
![13240 PETREL ST 5407, CLARKSBURG, MD, 20..., Clarksburg, MD 20871]()
3 beds
|2 baths
|2,031 sq ft
|Condo
13240 PETREL ST 5407, CLARKSBURG, MD, 20...
Community: Gatherings at Cabin Branch
MLS MDMC2237606 • Keller Williams Realty Centre, ...
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 at Cabin Branch
![13240 PETREL ST 5407, CLARKSBURG, MD, 20..., Clarksburg, MD 20871]()
3 beds
|2 baths
|2,031 sq ft
|Condo
13240 PETREL ST 5407, CLARKSBURG, MD, 20...
Community: The Village at Cabin Branch
MLS MDMC2237606 • Keller Williams Realty Centre, ...
Meadowview Village
![130 LEONARD LN, HARRISBURG, PA, 17111, Harrisburg, PA 17111]()
2 beds
|2 baths
|1,312 sq ft
|Condo
130 LEONARD LN, HARRISBURG, PA, 17111
Community: Meadowview Village
MLS PADA2060542 • Real of Pennsylvania, Collin Mi...
Amblebrook
![18 BROOMSEDGE LN, GETTYSBURG, PA, 17325, Gettysburg, PA 17325]()
MLS PAAD2023648 • Iron Valley Real Estate of Cent...
The Gatherings at Lakeview Community
![552 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136]()
3 beds
|3 baths
|2,475 sq ft
|Condo
552 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
Community: The Gatherings at Lakeview Community
MLS MDBC2164614 • Keller Williams Realty Centre, ...
The Gatherings at Lakeview Community
![586 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136]()
3 beds
|3 baths
|1,569 sq ft
|Condo
586 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
Community: The Gatherings at Lakeview Community
MLS MDBC2164606 • Keller Williams Realty Centre, ...
The Retreat at Poland Hill
![43489 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152]()
4 beds
|4 baths
|3,567 sq ft
43489 BETTYS FARM DR, CHANTILLY, VA, 201...
Community: The Retreat at Poland Hill
MLS VALO2126324 • EXP Realty, LLC, Barbara Y Blum...
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Questions? Call us:
(240) 663-8229
Leisure World® of Maryland
![3200 N LEISURE WORLD BLVD 1018, SILVER S..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,315 sq ft
|Condo
3200 N LEISURE WORLD BLVD 1018, SILVER S...
Community: Leisure World® of Maryland
MLS MDMC2236908 • Samson Properties, Karyn P Keat...
Amblebrook
![99 RUSTIC WOOD DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325]()
MLS PAAD2023654 • Monument Sotheby's Internationa...
Leisure World® of Maryland
![15100 INTERLACHEN DR 4-702, SILVER SPRIN..., Silver Spring, MD 20906]()
1 beds
|1 baths
|850 sq ft
|Condo
15100 INTERLACHEN DR 4-702, SILVER SPRIN...
Community: Leisure World® of Maryland
MLS MDMC2237356 • Coldwell Banker Realty, Rowena ...
Penn National
![6029 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222]()
MLS PAFL2034956 • Coldwell Banker Realty, Kevin R...
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.
Traditions of America at Silver Spring
![112 JAMES MADISON DR, MECHANICSBURG, PA,..., Mechanicsburg, PA 17050]()
2 beds
|2 baths
|1,289 sq ft
|Condo
112 JAMES MADISON DR, MECHANICSBURG, PA,...
Community: Traditions of America at Silver Spring
MLS PACB2054486 • Iron Valley Real Estate of Cent...
Leisure World® of Maryland
![15115 INTERLACHEN DR 3-311, SILVER SPRIN..., Silver Spring, MD 20906]()
1 beds
|1 baths
|945 sq ft
|Condo
15115 INTERLACHEN DR 3-311, SILVER SPRIN...
Community: Leisure World® of Maryland
MLS MDMC2237162 • RE/MAX Realty Services, Charles...
Cameron Grove
![14000 NEW ACADIA LN 308, UPPER MARLBORO,..., Upper Marlboro, MD 20774]()
2 beds
|2 baths
|1,429 sq ft
|Condo
14000 NEW ACADIA LN 308, UPPER MARLBORO,...
Community: Cameron Grove
MLS MDPG2204602 • Next Step Realty, LLC., Lauren ...
Spring Valley Estates
![11740 MYSTIC ROCK LN, WAYNESBORO, PA, 17..., Waynesboro, PA 17268]()
3 beds
|3 baths
|1,951 sq ft
11740 MYSTIC ROCK LN, WAYNESBORO, PA, 17...
Community: Spring Valley Estates
MLS PAFL2035052 • Real Estate Teams, LLC, Ashley ...
Leisure World® of Maryland
![3451 S LEISURE WORLD BLVD 83-G, SILVER S..., Silver Spring, MD 20906]()
2 beds
|3 baths
|1,600 sq ft
|Condo
3451 S LEISURE WORLD BLVD 83-G, SILVER S...
Community: Leisure World® of Maryland
MLS MDMC2236710 • RE/MAX Realty Group, Sally B Fr...
Greenvale Mews
![118 GREENVALE MEWS DR 24, WESTMINSTER, M..., Westminster, MD 21157]()
3 beds
|5 baths
|3,463 sq ft
|Condo
118 GREENVALE MEWS DR 24, WESTMINSTER, M...
Community: Greenvale Mews
MLS MDCR2035044 • Brook-Owen Real Estate, Denise ...
Leisure World® of Maryland
![14805 PENNFIELD CIR 412, SILVER SPRING, ..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,354 sq ft
|Condo
14805 PENNFIELD CIR 412, SILVER SPRING, ...
Community: Leisure World® of Maryland
MLS MDMC2236882 • Samson Properties, Isabel Carre...
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Heritage at St. Charles
![4614 DIAMOND RIDGE LN, WHITE PLAINS, MD,..., White Plains, MD 20695]()
3 beds
|3 baths
|2,541 sq ft
4614 DIAMOND RIDGE LN, WHITE PLAINS, MD,...
Community: Heritage at St. Charles
MLS MDCH2055190 • EXP Realty, LLC, Jonathan S Lah...
Trilogy® at Lake Frederick
![107 WAKE ROBIN CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|2,487 sq ft
107 WAKE ROBIN CT, LAKE FREDERICK, VA, 2...
Community: Trilogy® at Lake Frederick
MLS VAFV2042078 • Samson Properties, Katherine La...
Spring Hill
![8932 PINK CARNATION CT, LORTON, VA, 2207..., Lorton, VA 22079]()
MLS VAFX2315136 • Compass, Julie U Do
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
![14809 PENNFIELD CIR 314, SILVER SPRING, ..., Silver Spring, MD 20906]()
1 beds
|2 baths
|946 sq ft
|Condo
14809 PENNFIELD CIR 314, SILVER SPRING, ...
Community: Leisure World® of Maryland
MLS MDMC2236038 • Realty Advantage of Maryland LL...
Heritage Hunt
![6005 PINEY GROVE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2118996 • Compass, Catherine M Davidson
Suffield Meadows
![6708 STREAM VIEW LN, WARRENTON, VA, 2018..., Warrenton, VA 20187]()
3 beds
|3 baths
|3,701 sq ft
|Condo
6708 STREAM VIEW LN, WARRENTON, VA, 2018...
Community: Suffield Meadows
MLS VAFQ2022010 • Long & Foster Real Estate, Inc....
Regency at Dominion Valley
![15508 HAGEN WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|3,810 sq ft
15508 HAGEN WAY, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2120766 • KW United, Keith Herrmann
Cortland Park
![770 AURORA DR, MECHANICSBURG, PA, 17055, Mechanicsburg, PA 17055]()
MLS PACB2054390 • RE/MAX Realty Associates, Jenni...
The Courtyards at Waverly Woods
![2241 JOHN GRAVEL RD M, MARRIOTTSVILLE, M..., Marriottsville, MD 21104]()
2 beds
|2 baths
|1,438 sq ft
|Condo
2241 JOHN GRAVEL RD M, MARRIOTTSVILLE, M...
Community: The Courtyards at Waverly Woods
MLS MDHW2068894 • Fairfax Realty Premier, EUN M S...
Birchwood at Brambleton
![23640 BOLTON CRESCENT TER 403, ASHBURN, ..., Ashburn, VA 20148]()
3 beds
|2 baths
|1,908 sq ft
|Condo
23640 BOLTON CRESCENT TER 403, ASHBURN, ...
Community: Birchwood at Brambleton
MLS VALO2125616 • Compass, Scotti S Sellers
Heritage at St. Charles
![11271 YELLOWSTONE CT, WHITE PLAINS, MD, ..., White Plains, MD 20695]()
3 beds
|2 baths
|2,066 sq ft
11271 YELLOWSTONE CT, WHITE PLAINS, MD, ...
Community: Heritage at St. Charles
MLS MDCH2055360 • JPAR Real Estate Professionals,...
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HiddenBrooke
![7880 ROLLING WOODS CT 2103, SPRINGFIELD,..., Springfield, VA 22152]()
2 beds
|2 baths
|1,366 sq ft
|Condo
7880 ROLLING WOODS CT 2103, SPRINGFIELD,...
Community: HiddenBrooke
MLS VAFX2314738 • Coldwell Banker Realty, Tracy L...
Snowden Overlook
![8633 VAST ROSE DR 14, COLUMBIA, MD, 2104..., Columbia, MD 21045]()
2 beds
|4 baths
|3,542 sq ft
|Condo
8633 VAST ROSE DR 14, COLUMBIA, MD, 2104...
Community: Snowden Overlook
MLS MDHW2068786 • RE/MAX Advantage Realty, Timoth...
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.
Frequently Asked Questions
In Middletown, there is 1 small community with less than 500 homes.
The smallest 55+ community in Middletown has 81 homes, the largest has 81 homes, and the average community consists of 81 homes.
No, there are no gated 55+ communities in Middletown.
On average, listings in 55+ community in Middletown stay on the market for around 111 days. The average price of homes for sale in this community is approximately $600,106, though prices can range widely based on the size, location, and amenities of the community. For example, homes in The Village at Foxfield average around $600,106.
Want more information about active adult communities around Middletown?
Want to learn more about 55+ communities in Middletown?
582
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© 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: Jul 10, 2026.
This application does not include information on all of the properties available for sale at this time.
