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Middletown, MD 55+ active adult communities & homes for sale - Page 2
141 communities near Middletown
561 homes near Middletown
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$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
66 homes
- $600ks
Bethany Glen, Ellicott City, MD
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
116 homes
$600ks
- $700ks
Ellicott Meadows, Ellicott City, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
160 homes
$400ks
- $500ks
The Villages At Woodholme, Baltimore, MD
Resale Only
|
55+ age-restricted
|
Built 2002 - 2007
|
286 homes
3 rating (2 reviews)
![Dunbarton]()
$300ks
- $500ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 homes
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$400ks
- $500ks
Hawthorne Greene, La Plata, MD
Resale Only
|
55+ age-restricted
|
Built 2018 - 2022
|
74 homes
$500ks
- $900ks
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
$200ks
- $300ks
Eden Brook, Odenton, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
224 homes
$300ks
Village Crest, Ellicott City, MD
New and Resale
|
55+ age-restricted
|
Built 2005 - 2010
|
406 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.
$400ks
- $600ks
Spring Hill, Lorton, VA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2014
|
282 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$200ks
Country Manor, Shippensburg, PA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2018
|
130 homes
$400ks
Patapsco Overlook, Catonsville, MD
Resale Only
|
55+ age-restricted
|
Built 2010 - 2017
|
80 homes
$400ks
- $600ks
HiddenBrooke, West Springfield, VA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
91 homes
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$500ks
- $600ks
Crawfords Ridge, Odenton, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2006
|
27 homes
$300ks
- $400ks
Winchester Landing, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2023 - 2025
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$300ks
- $800ks
Regency at Ashburn, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2013 - 2020
|
268 homes
4 rating (2 reviews)
![Carmella]()
- $400ks
Carmella, Mechanicsburg, PA
Resale Only
|
55+ age-restricted
|
Built 2007 - 2017
|
190 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.
$100ks
- $200ks
Creek View, Carlisle, PA
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
305 homes
$300ks
- $600ks
Cortland Park, Mechanicsburg, PA
New and Resale
|
55+ age-restricted
|
Built 2020 - present
|
104 homes
$600ks
- $700ks
Robinson Manor, Gainesville, VA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
50 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$800ks
- $1Ms
Lexington Square, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
23 homes
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$300ks
- $400ks
Liberty Place, Sykesville, MD
Resale Only
|
55+ age-restricted
|
Built 2023 - present
|
54 homes
$900ks
- $800ks
Maple Highlands, Fulton, MD
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
34 homes
$400ks
The Reserve at New Windso..., New Windsor, MD
Resale Only
|
55+ age-restricted
|
Built 2016 - 2021
|
83 homes
$500ks
- $600ks
Walden Woods, Laurel, MD
Resale Only
|
55+ age-restricted
|
Built 2015 - 2020
|
97 homes
Want to learn more about 55+ rental communities in Middletown?
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$700ks
- $800ks
Scot's Glen, Columbia, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2012
|
73 homes
5 rating (1 reviews)
![Snowden Overlook]()
$300ks
- $600ks
Snowden Overlook, Columbia, MD
Resale Only
|
55+ age-restricted
|
Built 2005 - 2010
|
350 homes
$300ks
- $1Ms
The Courtyards at Waverly..., Marriottsville, MD
Resale Only
|
55+ age-restricted
|
Built 2012 - 2018
|
462 homes
$300ks
Gatherings at Forest Glen, Odenton, MD
Resale Only
|
55+ age-restricted
|
Built 2008 - 2013
|
189 homes
$500ks
Colonial Charles, Waldorf, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2018
|
240 homes
Want to learn more about 55+ communities in Middletown?
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$300ks
- $600ks
The Enclave at Ellicott H..., Ellicott City, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
280 homes
$300ks
- $500ks
Heritage at St. Charles, White Plains, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
300 homes
5 rating (1 reviews)
![Ellicott's Retreat]()
$300ks
- $400ks
Ellicott's Retreat, Ellicott City, MD
Resale Only
|
55+ age-restricted
|
Built 2017 - 2022
|
160 homes
$200ks
- $300ks
Washington Square, La Plata, MD
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
78 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
- $600ks
Nells Acres, Sykesville, MD
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
103 homes
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$300ks
- $600ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2010
|
383 homes
$400ks
- $500ks
Fairway Overlook, Elkridge, MD
Resale Only
|
55+ age-restricted
|
Built 2005 - 2006
|
25 homes
$200ks
- $300ks
Woodbrook Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2001
|
81 homes
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(240) 663-8229
$400ks
- $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
82 homes
New
Leisure World® of Maryland
![3210 N LEISURE WORLD BLVD 416, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,505 sq ft
|Condo
3210 N LEISURE WORLD BLVD 416, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2218842 • Weichert, REALTORS, Raquel Silv...
New
The Village at Harvest Ridge
![126 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601]()
3 beds
|2 baths
|2,834 sq ft
126 HARVEST RIDGE DR, WINCHESTER, VA, 22...
Community: The Village at Harvest Ridge
MLS VAFV2040774 • Long & Foster Real Estate, Inc....
New
Trilogy® at Lake Frederick
![104 GROSBEAK CT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,933 sq ft
104 GROSBEAK CT, LAKE FREDERICK, VA, 226...
Community: Trilogy® at Lake Frederick
MLS VAFV2039340 • Keller Williams Realty, Matt Bo...
New
CobbleStone Estates
![9723 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740]()
2 beds
|2 baths
|2,260 sq ft
9723 COBBLE STONE CT, HAGERSTOWN, MD, 21...
Community: CobbleStone Estates
MLS MDWA2035426 • Real Estate Innovations, Susan ...
New
Spring Hill
![8970 FASCINATION CT 215, LORTON, VA, 220..., Lorton, VA 22079]()
2 beds
|2 baths
|1,558 sq ft
|Condo
8970 FASCINATION CT 215, LORTON, VA, 220...
Community: Spring Hill
MLS VAFX2295904 • Samson Properties, Georgina P W...
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New
Heritage Hunt
![13520 NORWICK PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155]()
MLS VAPW2111482 • Samson Properties, Natalie H Mc...
New
Village Crest
![8270 STONE CROP DR A, ELLICOTT CITY, MD,..., Ellicott City, MD 21043]()
2 beds
|2 baths
|1,574 sq ft
|Condo
8270 STONE CROP DR A, ELLICOTT CITY, MD,...
Community: Village Crest
MLS MDHW2066694 • RE/MAX Advantage Realty, Greg M...
New
The Woodlands of Urbana
![3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704]()
3 beds
|3 baths
|1,816 sq ft
3225 THORNAPPLE DR, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2079850 • IMPACT Maryland Real Estate, St...
New
Parklands
![3908 GLACIER BAY PL, WHITE PLAINS, MD, 2..., White Plains, MD 20695]()
MLS MDCH2053244 • Keller Williams Preferred Prope...
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
Cedar Ridge at Piney Orchard
![8601 ROAMING RIDGE WAY 304, ODENTON, MD,..., Odenton, MD 21113]()
2 beds
|2 baths
|1,500 sq ft
|Condo
8601 ROAMING RIDGE WAY 304, ODENTON, MD,...
Community: Cedar Ridge at Piney Orchard
MLS MDAA2140798 • RE/MAX Leading Edge, Sandra K W...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New
Leisure World® of Maryland
![3330 N LEISURE WORLD BLVD 5-1027, SILVER..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,138 sq ft
|Condo
3330 N LEISURE WORLD BLVD 5-1027, SILVER...
Community: Leisure World® of Maryland
MLS MDMC2225782 • RLAH @properties, Jayme E Park
New
Carmella
![1006 WINTERGREEN DR, MECHANICSBURG, PA, ..., Mechanicsburg, PA 17050]()
3 beds
|3 baths
|2,538 sq ft
|Condo
1006 WINTERGREEN DR, MECHANICSBURG, PA, ...
Community: Carmella
MLS PACB2052408 • Iron Valley Real Estate of Cent...
New
Heritage Hunt
![6852 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155]()
MLS VAPW2115964 • Keller Williams Realty Advantag...
Want to learn more about 55+ communities in Middletown?
55places can help!
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New
Cameron Grove
![13506 MISSOULA CT, UPPER MARLBORO, MD, 2..., Upper Marlboro, MD 20774]()
MLS MDPG2198084 • Tek-Align Realty, LLC, Minassie...
New
Leisure World® of Maryland
![15020 EARDLEY CT 281G, SILVER SPRING, MD..., Silver Spring, MD 20906]()
1 beds
|1 baths
|666 sq ft
|Condo
15020 EARDLEY CT 281G, SILVER SPRING, MD...
Community: Leisure World® of Maryland
MLS MDMC2225842 • Weichert, REALTORS, Joseph D Pe...
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New
Potomac Green
![20598 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147]()
MLS VALO2120322 • Long & Foster Real Estate, Inc....
New
The Crest of Alexandria
![7753 BELVALE DR, ALEXANDRIA, VA, 22315, Alexandria, VA 22315]()
4 beds
|4 baths
|2,888 sq ft
7753 BELVALE DR, ALEXANDRIA, VA, 22315
Community: The Crest of Alexandria
MLS VAFX2296586 • Redfin Corporation, Matthew Dav...
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
The Highlands at Blue Ridge Shadows
![48 HICKORY SHAFT CT, FRONT ROYAL, VA, 22..., Front Royal, VA 22630]()
3 beds
|2 baths
|1,763 sq ft
48 HICKORY SHAFT CT, FRONT ROYAL, VA, 22...
Community: The Highlands at Blue Ridge Shadows
MLS VAWR2013914 • Keller Williams Realty, Alicia ...
New
Ballenger Run
![6443 AUTUMN OLIVE DR, FREDERICK, MD, 217..., Frederick, MD 21703]()
MLS MDFR2079720 • RE/MAX Results, Sue P Collins
New
Leisure World® of Maryland
![14801 PENNFIELD CIR 206, SILVER SPRING, ..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,312 sq ft
|Condo
14801 PENNFIELD CIR 206, SILVER SPRING, ...
Community: Leisure World® of Maryland
MLS MDMC2224690 • NextHome Envision, Catelin Schw...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New
Lansdowne Woods of Virginia
![19355 CYPRESS RIDGE TER 219, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,500 sq ft
|Condo
19355 CYPRESS RIDGE TER 219, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2119234 • Compass, Karen A Miller
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New
Heritage Hunt
![13700 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2114682 • Pearson Smith Realty, LLC, Cher...
New
Leisure World® of Maryland
![3210 N LEISURE WORLD BLVD 519, SILVER SP..., Silver Spring, MD 20906]()
1 beds
|2 baths
|885 sq ft
|Condo
3210 N LEISURE WORLD BLVD 519, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2225530 • Samson Properties, Eve R Marini...
New
Leisure World® of Maryland
![3411 S LEISURE WORLD BLVD 90-E, SILVER S..., Silver Spring, MD 20906]()
2 beds
|3 baths
|1,600 sq ft
|Condo
3411 S LEISURE WORLD BLVD 90-E, SILVER S...
Community: Leisure World® of Maryland
MLS MDMC2225508 • RE/MAX Realty Services, Charles...
New
Lansdowne Woods of Virginia
![19350 MAGNOLIA GROVE SQ 403, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,168 sq ft
|Condo
19350 MAGNOLIA GROVE SQ 403, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2120272 • Keller Williams Realty, Suzanne...
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New
Amblebrook
![102 WOOLGRASS LN, GETTYSBURG, PA, 17325, Gettysburg, PA 17325]()
MLS PAAD2022742 • RE/MAX Advantage Realty, Charle...
New
Patapsco Overlook
![17 CLAY LODGE LN 304, CATONSVILLE, MD, 2..., Catonsville, MD 21228]()
2 beds
|2 baths
|1,422 sq ft
|Condo
17 CLAY LODGE LN 304, CATONSVILLE, MD, 2...
Community: Patapsco Overlook
MLS MDBC2157864 • Cummings & Co. Realtors, Morgan...
New
Four Seasons at Historic Virginia
![17322 FOUR SEASONS DR, DUMFRIES, VA, 220..., Dumfries, VA 22025]()
3 beds
|2 baths
|1,802 sq ft
17322 FOUR SEASONS DR, DUMFRIES, VA, 220...
Community: Four Seasons at Historic Virginia
MLS VAPW2114982 • Samson Properties, Ashley Kopec...
New
Birchwood at Brambleton
![42920 FIREFLY SONATA TER 203, ASHBURN, V..., Ashburn, VA 20148]()
3 beds
|2 baths
|1,712 sq ft
|Condo
42920 FIREFLY SONATA TER 203, ASHBURN, V...
Community: Birchwood at Brambleton
MLS VALO2120184 • Samson Properties, Meg Elizabet...
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New
Lansdowne Woods of Virginia
![19375 CYPRESS RIDGE TER 1111, LEESBURG, ..., Leesburg, VA 20176]()
3 beds
|2 baths
|1,475 sq ft
|Condo
19375 CYPRESS RIDGE TER 1111, LEESBURG, ...
Community: Lansdowne Woods of Virginia
MLS VALO2116242 • Samson Properties, Andrew M Nor...
New
Trilogy® at Lake Frederick
![104 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,457 sq ft
104 RHODODENDRON CT, LAKE FREDERICK, VA,...
Community: Trilogy® at Lake Frederick
MLS VAFV2040680 • Keller Williams Realty, Matt Bo...
New
Amblebrook
![74 GRAND OVERLOOK DR, GETTYSBURG, PA, 17..., Gettysburg, PA 17325]()
MLS PAAD2022492 • Tesla Realty Group, LLC, Mary Y...
New
Leisure World® of Maryland
![15401 BASSETT LN 45-2C, SILVER SPRING, M..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,237 sq ft
|Condo
15401 BASSETT LN 45-2C, SILVER SPRING, M...
Community: Leisure World® of Maryland
MLS MDMC2225408 • Weichert, REALTORS, Colleen M C...
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
![3200 N LEISURE WORLD BLVD 803, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,495 sq ft
|Condo
3200 N LEISURE WORLD BLVD 803, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2225460 • RE/MAX Realty Services, John P....
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New
Walden Woods
![9837 WILDERNESS LN, LAUREL, MD, 20723, Laurel, MD 20723]()
MLS MDHW2066628 • Cummings & Co. Realtors, Janet ...
Liberty Grove
![8610 LIBERTY TRL 305, MANASSAS, VA, 2011..., Manassas, VA 20110]()
2 beds
|3 baths
|1,518 sq ft
|Condo
8610 LIBERTY TRL 305, MANASSAS, VA, 2011...
Community: Liberty Grove
MLS VAMN2010576 • Keller Williams Realty, Jennife...
Parklands
![10071 SHENANDOAH LN, WHITE PLAINS, MD, 2..., White Plains, MD 20695]()
MLS MDCH2053060 • Builder Solutions Realty, Terri...
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Amblebrook
![96 ELDERBERRY WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325]()
MLS PAAD2022756 • D.R. Horton Realty of Pennsylva...
Vistas at Lansdowne
![19400 LANSDOWNE WOODS BLVD 101, LEESBURG..., Leesburg, VA 20176]()
2 beds
|2 baths
|2,041 sq ft
|Condo
19400 LANSDOWNE WOODS BLVD 101, LEESBURG...
Community: Vistas at Lansdowne
MLS VALO2120042 • Samson Properties, Phyllis Ann ...
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 58 days. The average price of homes for sale in this community is approximately $550,000, 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 $550,000.
Want more information about active adult communities around Middletown?
Want to learn more about 55+ communities in Middletown?
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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: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
