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Middletown, MD 55+ active adult communities & homes for sale - Page 15
142 communities near Middletown
627 homes near Middletown
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2.3 rating (3 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
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
4.3 rating (11 reviews)
![Amblebrook]()
$300ks
- $700ks
Amblebrook, Gettysburg, PA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
2,000 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
$300ks
- $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2026 - present
|
500 homes
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$300ks
- $500ks
Parklands, White Plains, MD
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
586 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
$100ks
- $600ks
Penn National, Fayetteville, PA
New and Resale
|
Age-targeted
|
Built 1968 - present
|
1,100 homes
5 rating (1 reviews)
![Two Rivers]()
$500ks
- $700ks
Two Rivers, Odenton, MD
New and Resale
|
55+ age-restricted
|
Built 2015 - present
|
800 homes
$600ks
- $1Ms
The Flats at Northside, Potomac, MD
New Construction
|
Age-targeted
|
Built 2025 - present
|
143 homes
Download the Ultimate 55+ Homebuying Guide
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5 rating (3 reviews)
![Heritage Hunt]()
$400ks
- $600ks
Heritage Hunt, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2009
|
1,863 homes
$400ks
- $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
135 homes
$500ks
The Village at Cabin Bran..., Clarksburg, MD
New Construction
|
55+ age-restricted
|
Built 2021 - present
$300ks
- $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
122 homes
$200ks
- $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
- $500ks
Central Parke at Victoria..., Laurel, MD
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
609 homes
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(240) 663-8229
$400ks
- $600ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
517 homes
$500ks
- $600ks
Willow Run, Winchester, VA
New Construction
|
55+ age-restricted
|
300 homes
$500ks
- $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2025
|
565 homes
5 rating (1 reviews)
![Snowden Overlook]()
$300ks
- $600ks
Snowden Overlook, Columbia, MD
Resale Only
|
55+ age-restricted
|
Built 2005 - 2010
|
350 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.
$600ks
- $700ks
The Atrium at MetroWest, Fairfax, VA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
206 homes
$300ks
- $400ks
Spring Valley Estates, Waynesboro, PA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
140 homes
$400ks
- $500ks
Signature Club at Greenvi..., New Market, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
233 homes
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
$700ks
- $800ks
Bloomfields 55+, Frederick, MD
New Construction
|
55+ age-restricted
|
Built 2026 - present
$300ks
- $500ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
177 homes
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$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2024
|
74 homes
$300ks
Carroll's Creek, Gambrills, MD
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
162 homes
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
66 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.
$300ks
- $900ks
Cromwell 55+, Ijamsville, MD
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
488 homes
$300ks
- $400ks
Winchester Landing, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2023 - 2025
$400ks
- $500ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
185 homes
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
$200ks
- $400ks
Beechfield Manors, Bowie, MD
New Construction
|
55+ age-restricted
|
Built 2024 - present
3 rating (2 reviews)
![Dunbarton]()
$300ks
- $500ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 homes
$200ks
Country Manor, Shippensburg, PA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2018
|
130 homes
5 rating (1 reviews)
![Willow Lawn Cottages]()
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2004
|
120 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(240) 663-8229
$300ks
- $400ks
Sagebrook, Dover, PA
New and Resale
|
55+ age-restricted
|
Built 2020 - present
|
194 homes
$300ks
- $1Ms
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.
Trilogy® at Lake Frederick
![107 YELLOW BIRCH CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630]()
3 beds
|5 baths
|4,465 sq ft
107 YELLOW BIRCH CT, LAKE FREDERICK, VA,...
Community: Trilogy® at Lake Frederick
MLS VAFV2039876 • HomeZu.com of Virginia, Jason P... • HomeZu.com of Virginia
Trilogy® at Lake Frederick
![124 CHECKERSPOT WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630]()
4 beds
|4 baths
|2,508 sq ft
124 CHECKERSPOT WAY, LAKE FREDERICK, VA,...
Community: Trilogy® at Lake Frederick
MLS VAFV2039798 • Realty FC, Gloria J Ryan • Realty FC
Cameron Grove
![13310 NEW ACADIA LN 206, UPPER MARLBORO,..., Upper Marlboro, MD 20774]()
2 beds
|2 baths
|1,287 sq ft
|Condo
13310 NEW ACADIA LN 206, UPPER MARLBORO,...
Community: Cameron Grove
MLS MDPG2193206 • Taylor Properties, Kara J Ellis • Taylor Properties
Amblebrook
![371 QUIET CREEK DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325]()
MLS PAAD2022042 • Joy Daniels Real Estate Group, ... • Joy Daniels Real Estate Group, Ltd
Leisure World® of Maryland
![3005 S LEISURE WORLD BLVD 702, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,093 sq ft
|Condo
3005 S LEISURE WORLD BLVD 702, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2218188 • EXP Realty, LLC, Daniel A Linar... • EXP Realty, LLC
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Cindy Certified
Trilogy® at Lake Frederick
![136 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630]()
2 beds
|2 baths
|2,089 sq ft
136 MALLARD DR, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2039502 • MarketPlace REALTY, Kimberly D ... • MarketPlace REALTY
Willow Run
![228 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2039560 • D R Horton Realty of Virginia L... • D R Horton Realty of Virginia LLC
Cindy Certified
Birchwood at Brambleton
![23631 HAVELOCK WALK TER 421, ASHBURN, VA..., Ashburn, VA 20148]()
3 beds
|2 baths
|1,906 sq ft
|Condo
23631 HAVELOCK WALK TER 421, ASHBURN, VA...
Community: Birchwood at Brambleton
MLS VALO2113380 • Real Broker, LLC, Peter B Knapp • Real Broker, LLC
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.
Rosehill Manor Villas
![19604 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742]()
2 beds
|2 baths
|1,767 sq ft
19604 LAVENDER LN, HAGERSTOWN, MD, 21742
Community: Rosehill Manor Villas
MLS MDWA2033864 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
Cindy Certified
Cadence at Lansdowne
![18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176]()
3 beds
|3 baths
|2,649 sq ft
18989 CORAL REEF SQ, LEESBURG, VA, 20176
Community: Cadence at Lansdowne
MLS VALO2114652 • Pearson Smith Realty, LLC, Mage... • Pearson Smith Realty, LLC
The Flats at Heathcote Village by Del Webb
![6033 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,763 sq ft
6033 SUNSTONE LN, HAYMARKET, VA, 20169
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2111662 • Monument Sotheby's Internationa... • Monument Sotheby's International Realty
Country Manor
![95 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2050102 • Coldwell Banker Realty, Brian M... • Coldwell Banker Realty
Cindy Certified
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(240) 663-8229
Rosehill Manor Villas
![13354 SNAPDRAGON WAY, HAGERSTOWN, MD, 21..., Hagerstown, MD 21742]()
3 beds
|2 baths
|1,466 sq ft
13354 SNAPDRAGON WAY, HAGERSTOWN, MD, 21...
Community: Rosehill Manor Villas
MLS MDWA2033772 • DRB Group Realty, LLC, Chaquia ... • DRB Group Realty, LLC
Rosehill Manor Villas
![13352 SNAPDRAGON WAY, HAGERSTOWN, MD, 21..., Hagerstown, MD 21742]()
3 beds
|2 baths
|1,687 sq ft
13352 SNAPDRAGON WAY, HAGERSTOWN, MD, 21...
Community: Rosehill Manor Villas
MLS MDWA2033770 • DRB Group Realty, LLC, Chaquia ... • DRB Group Realty, LLC
Cindy Certified
The Village at Cabin Branch
![13230 PETREL ST 2301, CLARKSBURG, MD, 20..., Clarksburg, MD 20871]()
2 beds
|2 baths
|1,702 sq ft
|Condo
13230 PETREL ST 2301, CLARKSBURG, MD, 20...
Community: The Village at Cabin Branch
MLS MDMC2214556 • Keller Williams Realty Centre, ... • 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.
Gatherings at Cabin Branch
![13230 PETREL ST 2301, CLARKSBURG, MD, 20..., Clarksburg, MD 20871]()
2 beds
|2 baths
|1,702 sq ft
|Condo
13230 PETREL ST 2301, CLARKSBURG, MD, 20...
Community: Gatherings at Cabin Branch
MLS MDMC2214556 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
Leisure World® of Maryland
![15320 PINE ORCHARD DR 83-C1, SILVER SPRI..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,043 sq ft
|Condo
15320 PINE ORCHARD DR 83-C1, SILVER SPRI...
Community: Leisure World® of Maryland
MLS MDMC2213952 • Samson Properties, Catherine So... • Samson Properties
Gatherings at Wellington
![10275 FOUNTAIN CIR 201, MANASSAS, VA, 20..., Manassas, VA 20110]()
2 beds
|2 baths
|1,441 sq ft
|Condo
10275 FOUNTAIN CIR 201, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2009920 • Keller Williams Realty, Jennife... • Keller Williams Realty
The Village at Freedom Hills
![13948 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740]()
2 beds
|2 baths
|1,430 sq ft
13948 PATRIOT WAY, HAGERSTOWN, MD, 21740
Community: The Village at Freedom Hills
MLS MDWA2033432 • Samson Properties, Megan Harnis... • Samson Properties
Leisure World® of Maryland
![15311 PINE ORCHARD DR 87-1H, SILVER SPRI..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,043 sq ft
|Condo
15311 PINE ORCHARD DR 87-1H, SILVER SPRI...
Community: Leisure World® of Maryland
MLS MDMC2208124 • Weichert, REALTORS, Robert J Fo... • Weichert, REALTORS
Cameron Grove
![1 CAMERON GROVE BLVD 202, UPPER MARLBORO..., Upper Marlboro, MD 20774]()
2 beds
|2 baths
|1,208 sq ft
|Condo
1 CAMERON GROVE BLVD 202, UPPER MARLBORO...
Community: Cameron Grove
MLS MDPG2187388 • Express Brokers Realty LLC, Anj... • Express Brokers Realty LLC
Leisure World® of Maryland
![15211 ELKRIDGE WAY 94-3C, SILVER SPRING,..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,030 sq ft
|Condo
15211 ELKRIDGE WAY 94-3C, SILVER SPRING,...
Community: Leisure World® of Maryland
MLS MDMC2211240 • The Agency DC, Michael Konstant... • The Agency DC
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(240) 663-8229
Amblebrook
![207 GRAND OVERLOOK DR, GETTYSBURG, PA, 1..., Gettysburg, PA 17325]()
MLS PAAD2021056 • Kelly and Co Realty, LLC, Kelly... • Kelly and Co Realty, LLC
Cindy Certified
Carroll's Creek
![1412 WIGEON WAY 101, GAMBRILLS, MD, 2105..., Gambrills, MD 21054]()
3 beds
|2 baths
|1,777 sq ft
|Condo
1412 WIGEON WAY 101, GAMBRILLS, MD, 2105...
Community: Carroll's Creek
MLS MDAA2132658 • Berkshire Hathaway HomeServices... • Berkshire Hathaway HomeServices PenFed Realty
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 Atrium at MetroWest
![9555 SAINTSBURY DR 503, FAIRFAX, VA, 220..., Fairfax, VA 22031]()
2 beds
|2 baths
|1,546 sq ft
|Condo
9555 SAINTSBURY DR 503, FAIRFAX, VA, 220...
Community: The Atrium at MetroWest
MLS VAFX2280722 • Libra Realty, LLC, Rong Ma • Libra Realty, LLC
Cameron Grove
![14040 NEW ACADIA LN 107, UPPER MARLBORO,..., Upper Marlboro, MD 20774]()
2 beds
|2 baths
|1,122 sq ft
|Condo
14040 NEW ACADIA LN 107, UPPER MARLBORO,...
Community: Cameron Grove
MLS MDPG2185304 • Taylor Properties, Trent Rawls • Taylor Properties
Cindy Certified
Traditions of America at Silver Spring
![153 JAMES MADISON DR, MECHANICSBURG, PA,..., Mechanicsburg, PA 17050]()
3 beds
|3 baths
|2,293 sq ft
|Condo
153 JAMES MADISON DR, MECHANICSBURG, PA,...
Community: Traditions of America at Silver Spring
MLS PACB2048366 • Iron Valley Real Estate of Cent... • Iron Valley Real Estate of Central PA
Beechfield Manors
![4003 SEASIDE ALDER RD 0201 - ROSE, BOWIE..., Bowie, MD 20720]()
2 beds
|2 baths
|1,294 sq ft
|Condo
4003 SEASIDE ALDER RD 0201 - ROSE, BOWIE...
Community: Beechfield Manors
MLS MDPG2182012 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
Parklands
![10628 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695]()
MLS MDCH2048808 • Samson Properties, John Michael... • Samson Properties
Snowden Overlook
![8656 VAST ROSE DR 23, COLUMBIA, MD, 2104..., Columbia, MD 21045]()
4 beds
|5 baths
|3,719 sq ft
|Condo
8656 VAST ROSE DR 23, COLUMBIA, MD, 2104...
Community: Snowden Overlook
MLS MDHW2060718 • RE/MAX Advantage Realty, Timoth... • RE/MAX Advantage Realty
The Gatherings at Lakeview Community
![600 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136]()
3 beds
|3 baths
|1,569 sq ft
|Condo
600 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
Community: The Gatherings at Lakeview Community
MLS MDBC2143586 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
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Leisure World® of Maryland
![3200 N LEISURE WORLD BLVD 514, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,035 sq ft
|Condo
3200 N LEISURE WORLD BLVD 514, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2204194 • Weichert, REALTORS, Eileen K Ka... • Weichert, REALTORS
The Atrium at MetroWest
![2960 VADEN DR 2-406, FAIRFAX, VA, 22031, Fairfax, VA 22031]()
2 beds
|2 baths
|1,391 sq ft
|Condo
2960 VADEN DR 2-406, FAIRFAX, VA, 22031
Community: The Atrium at MetroWest
MLS VAFX2274800 • Pearson Smith Realty, LLC, Jiun... • Pearson Smith Realty, LLC
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?
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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: Aug 24, 2026.
This application does not include information on all of the properties available for sale at this time.
