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Middletown, MD 55+ active adult communities & homes for sale - Page 3
143 communities near Middletown
663 homes near Middletown
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$300ks
- $400ks
The Signature at Broadlan..., Ashburn, VA
Resale Only
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55+ age-restricted
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Built 2018 - 2020
|
45 homes
$600ks
- $700ks
Walhaven at Kingstowne, Franconia, VA
Resale Only
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55+ age-restricted
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Built 2018 - 2019
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32 homes
$600ks
- $700ks
Ellicott Meadows, Ellicott City, MD
Resale Only
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55+ age-restricted
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Built 2003 - 2006
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160 homes
$300ks
- $500ks
The Villas of Rock Oak, Odenton, MD
Resale Only
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55+ age-restricted
|
Built 2004 - 2006
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38 homes
$400ks
Patapsco Overlook, Catonsville, MD
Resale Only
|
55+ age-restricted
|
Built 2010 - 2017
|
80 homes
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$400ks
- $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction
|
55+ age-restricted
|
Built 2023 - 2024
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55 homes
$300ks
- $400ks
JerMae Estates, Thurmont, MD
Resale Only
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55+ age-restricted
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Built 2003 - 2008
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108 homes
5 rating (1 reviews)
![Carroll Vista]()
$300ks
Carroll Vista, Taneytown, MD
Resale Only
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55+ age-restricted
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Built 2004 - 2017
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453 homes
$300ks
Gatherings at Ellicott Mi..., Ellicott City, MD
Resale Only
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55+ age-restricted
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Built 2013 - 2018
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127 homes
$300ks
- $600ks
Cortland Park, Mechanicsburg, PA
New and Resale
|
55+ age-restricted
|
Built 2020 - present
|
104 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
Colonial Charles, Waldorf, MD
Resale Only
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55+ age-restricted
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Built 2006 - 2018
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240 homes
1 rating (1 reviews)
![Legacy at Cherry Tree]()
$400ks
- $500ks
Legacy at Cherry Tree, Laurel, MD
Resale Only
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55+ age-restricted
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Built 2010 - 2015
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120 homes
$300ks
- $500ks
Heritage at St. Charles, White Plains, MD
Resale Only
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55+ age-restricted
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Built 2006 - 2016
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300 homes
$500ks
- $600ks
Boxwood Villas, Urbana, MD
Resale Only
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55+ age-restricted
|
Built 2019 - 2021
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92 homes
$200ks
- $300ks
Washington Square, La Plata, MD
Resale Only
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55+ age-restricted
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Built 1999 - 2006
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78 homes
$300ks
- $600ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2010
|
383 homes
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$400ks
- $500ks
Fairway Overlook, Elkridge, MD
Resale Only
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55+ age-restricted
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Built 2005 - 2006
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25 homes
$300ks
- $500ks
The Village at Foxfield, Middletown, MD
Resale Only
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55+ age-restricted
|
Built 2003 - 2012
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81 homes
$300ks
- $400ks
Sagebrook, Dover, PA
New and Resale
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55+ age-restricted
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Built 2020 - present
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194 homes
- $600ks
Bethany Glen, Ellicott City, MD
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
116 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
- $500ks
Hickory Crest, Columbia, MD
Resale Only
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55+ age-restricted
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Built 2000 - 2002
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88 homes
$400ks
- $500ks
Greenvale Mews, Westminster, MD
Resale Only
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55+ age-restricted
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Built 2013 - 2016
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65 homes
5 rating (1 reviews)
![Gatherings at Lyndwood]()
$300ks
- $400ks
Gatherings at Lyndwood, Elkridge, MD
Resale Only
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55+ age-restricted
|
Built 2005 - 2008
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216 homes
5 rating (1 reviews)
![Villas at Cattail Creek]()
$500ks
- $1Ms
Villas at Cattail Creek, Glenwood, MD
Resale Only
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55+ age-restricted
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Built 2004 - 2006
|
93 homes
3.5 rating (4 reviews)
![Bent Creek Crossing]()
$300ks
Bent Creek Crossing, Mechanicsburg, PA
Resale Only
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55+ age-restricted
|
Built 1998 - 2004
|
110 homes
$400ks
- $500ks
Abrams Chase, Winchester, VA
New Construction
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55+ age-restricted
|
Built 2020 - present
|
13 homes
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2022
|
219 homes
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$400ks
- $700ks
Carter's Mill, Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
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480 homes
$300ks
Villas at Cattail, Hanover, PA
Resale Only
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55+ age-restricted
|
Built 2007 - 2013
|
48 homes
$300ks
- $400ks
Saintsbury Plaza, Fairfax, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2006
|
111 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
- $300ks
Cherry Tree, Hanover, PA
New Construction
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55+ age-restricted
|
Built 2018 - present
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100 homes
$700ks
- $900ks
Railroad Cottages, Falls Church, VA
Resale Only
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55+ age-restricted
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Built 2019 - 2021
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10 homes
$100ks
- $200ks
Longstown Village, York, PA
Resale Only
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Age-targeted
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Built 1997 - 2000
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304 homes
$400ks
Cottage Glen, Winchester, VA
New and Resale
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Age-targeted
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Built 2018 - present
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25 homes
$400ks
- $500ks
Gatherings® at Quarry Pla..., Reisterstown, MD
Resale Only
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55+ age-restricted
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Built 2014 - 2017
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135 homes
4 rating (2 reviews)
![Carmella]()
$400ks
Carmella, Mechanicsburg, PA
Resale Only
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55+ age-restricted
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Built 2007 - 2017
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190 homes
$500ks
- $600ks
Enclave at Park Forest, Elkridge, MD
Resale Only
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55+ age-restricted
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Built 2016 - 2018
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45 homes
$200ks
- $300ks
Amesbury, Harrisburg, PA
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
106 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(240) 663-8229
$400ks
- $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale
|
55+ age-restricted
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Built 2015 - present
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66 homes
$900ks
- $1Ms
Trotter's Retreat, Clarksville, MD
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
25 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.
Amblebrook
![371 QUIET CREEK DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325]()
MLS PAAD2026018 • Iron Valley Real Estate of Cent... • Iron Valley Real Estate of Central PA
Amblebrook
![44 ROLLING HLS, GETTYSBURG, PA, 17325, Gettysburg, PA 17325]()
MLS PAAD2025758 • Iron Valley Real Estate of Cent... • Iron Valley Real Estate of Central PA
Amblebrook
![59 BIRDSEYE LN, GETTYSBURG, PA, 17325, Gettysburg, PA 17325]()
MLS PAAD2025578 • Iron Valley Real Estate of Cent... • Iron Valley Real Estate of Central PA
Trilogy® at Lake Frederick
![100 SCOTER CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
3 beds
|4 baths
|4,247 sq ft
100 SCOTER CT, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2044118 • Colony Realty, Paul J Gallagher... • Colony Realty
Heritage Hunt
![7065 HERITAGE HUNT DR 108, GAINESVILLE, ..., Gainesville, VA 20155]()
2 beds
|2 baths
|1,292 sq ft
|Condo
7065 HERITAGE HUNT DR 108, GAINESVILLE, ...
Community: Heritage Hunt
MLS VAPW2125268 • MYVAHOME.COM LLC, Curtis Scott • MYVAHOME.COM LLC
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Trilogy® at Lake Frederick
![109 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630]()
4 beds
|4 baths
|3,859 sq ft
109 EMPEROR DR, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2041588 • Colony Realty, Paul J Gallagher... • Colony Realty
Amblebrook
![321 HIGHLAND WAY 160, GETTYSBURG, PA, 17..., Gettysburg, PA 17325]()
MLS PAAD2021796 • Iron Valley Real Estate of Cent... • Iron Valley Real Estate of Central PA
New
Leisure World® of Maryland
![3100 N LEISURE WORLD BLVD 612, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,325 sq ft
3100 N LEISURE WORLD BLVD 612, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2258094 • Compass, Leslie C Friedson • Compass
New
Heritage Hunt
![6900 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2132024 • REALTYPEOPLE, Michael T Gorman • REALTYPEOPLE
New
Lansdowne Woods of Virginia
![19355 CYPRESS RIDGE TER 905, LEESBURG, V..., Leesburg, VA 20176]()
1 beds
|2 baths
|874 sq ft
|Condo
19355 CYPRESS RIDGE TER 905, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2137996 • AMPLUS REALTY, LLC., Young-ae B... • AMPLUS 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.
New
Amblebrook
![117 ELDERBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325]()
MLS PAAD2026088 • D.R. Horton Realty of Pennsylva... • D.R. Horton Realty of Pennsylvania
New
![1761 OLD MEADOW RD 102, MCLEAN, VA, 2210..., Mclean, VA 22102]()
Cindy Certified
New
Potomac Green
![20630 HOPE SPRING TER 303, ASHBURN, VA, ..., Ashburn, VA 20147]()
2 beds
|2 baths
|1,347 sq ft
|Condo
20630 HOPE SPRING TER 303, ASHBURN, VA, ...
Community: Potomac Green
MLS VALO2137546 • Keller Williams Realty, Nancy L... • Keller Williams Realty
New
![210 E SECOND ST 401, FREDERICK, MD, 2170..., Frederick, MD 21701]()
Cindy Certified
New
The Flats at Heathcote Village by Del Webb
![5988 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,625 sq ft
5988 SUNSTONE LN, HAYMARKET, VA, 20169
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2131924 • Monument Sotheby's Internationa... • Monument Sotheby's International Realty
New
![1611 POTOMAC SHORES PKWY 402, DUMFRIES, ..., Dumfries, VA 22026]()
Cindy Certified
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(240) 663-8229
New
Leisure World® of Maryland
![14905 PENNFIELD CIR 2A, SILVER SPRING, M..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,391 sq ft
|Condo
14905 PENNFIELD CIR 2A, SILVER SPRING, M...
Community: Leisure World® of Maryland
MLS MDMC2258846 • Weichert, REALTORS, Ledio Baboc... • Weichert, REALTORS
New
Crestwood Village
![6874 BUTTONWOOD CT, FREDERICK, MD, 21703, Frederick, MD 21703]()
2 beds
|2 baths
|1,164 sq ft
6874 BUTTONWOOD CT, FREDERICK, MD, 21703
Community: Crestwood Village
MLS MDFR2090268 • Maryland Elite Realtors, Cassan... • Maryland Elite Realtors
New
Leisure World® of Maryland
![2921 N LEISURE WORLD BLVD 1-216, SILVER ..., Silver Spring, MD 20906]()
1 beds
|2 baths
|803 sq ft
|Condo
2921 N LEISURE WORLD BLVD 1-216, SILVER ...
Community: Leisure World® of Maryland
MLS MDMC2258802 • RLAH @properties, Larry B Priga... • RLAH @properties
New
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 VAFV2045274 • Keller Williams Realty, Karl Ac... • Keller Williams 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.
New
Birchwood at Brambleton
![42724 CUSHING TER, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|4 baths
|3,735 sq ft
42724 CUSHING TER, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2137794 • Samson Properties, Tracy A Weng... • Samson Properties
Maple Highlands
![8547 LALLYBROCH LN, FULTON, MD, 20759, Fulton, MD 20759]()
4 beds
|4 baths
|4,939 sq ft
|Condo
8547 LALLYBROCH LN, FULTON, MD, 20759
Community: Maple Highlands
MLS MDHW2074770 • The KW Collective, Charlotte Sa... • The KW Collective
Regency at Dominion Valley
![15508 HAGEN WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|4,050 sq ft
15508 HAGEN WAY, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2131846 • Samson Properties, Allie Chambe... • Samson Properties
Colonial Charles
![10652 SHADOW PARK CT, WALDORF, MD, 20603, Waldorf, MD 20603]()
MLS MDCH2059892 • The Agency DC, Cher L Castillo • The Agency DC
Ballenger Run
![5312 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703]()
MLS MDFR2089976 • Compass, Janelle Harwood • Compass
Leisure World® of Maryland
![3330 N LEISURE WORLD BLVD 5-422, SILVER ..., Silver Spring, MD 20906]()
1 beds
|2 baths
|930 sq ft
|Condo
3330 N LEISURE WORLD BLVD 5-422, SILVER ...
Community: Leisure World® of Maryland
MLS MDMC2258412 • Weichert, REALTORS, Richard D W... • Weichert, REALTORS
Cindy Certified
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Birchwood at Brambleton
![42874 FIREFLY SONATA TER 409, ASHBURN, V..., Ashburn, VA 20148]()
3 beds
|2 baths
|2,149 sq ft
|Condo
42874 FIREFLY SONATA TER 409, ASHBURN, V...
Community: Birchwood at Brambleton
MLS VALO2137190 • Keller Williams Realty, Jean K ... • Keller Williams Realty
Willow Run
![225 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2045242 • D R Horton Realty of Virginia L... • D R Horton Realty of Virginia LLC
Bloomfields 55+
![2641 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702]()
MLS MDFR2090174 • 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.
Bloomfields 55+
![2603 - C BLAZING STAR ST, FREDERICK, MD,..., Frederick, MD 21702]()
4 beds
|4 baths
|4,062 sq ft
2603 - C BLAZING STAR ST, FREDERICK, MD,...
Community: Bloomfields 55+
MLS MDFR2089890 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
Bloomfields 55+
![2603 - D BLAZING STAR ST, FREDERICK, MD,..., Frederick, MD 21702]()
4 beds
|4 baths
|4,501 sq ft
2603 - D BLAZING STAR ST, FREDERICK, MD,...
Community: Bloomfields 55+
MLS MDFR2089884 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
Bloomfields 55+
![2603 - B BLAZING STAR ST, FREDERICK, MD,..., Frederick, MD 21702]()
3 beds
|3 baths
|3,821 sq ft
2603 - B BLAZING STAR ST, FREDERICK, MD,...
Community: Bloomfields 55+
MLS MDFR2089864 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
Bloomfields 55+
![2603 - A BLAZING STAR ST, FREDERICK, MD,..., Frederick, MD 21702]()
3 beds
|3 baths
|3,387 sq ft
2603 - A BLAZING STAR ST, FREDERICK, MD,...
Community: Bloomfields 55+
MLS MDFR2089862 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
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 MDMC2258542 • EXP Realty, LLC, Daniel A Linar... • EXP Realty, LLC
Trilogy® at Lake Frederick
![121 FOAM FLOWER DR, LAKE FREDERICK, VA, ..., Lake Frederick, VA 22630]()
3 beds
|2 baths
|2,089 sq ft
121 FOAM FLOWER DR, LAKE FREDERICK, VA, ...
Community: Trilogy® at Lake Frederick
MLS VAFV2045202 • Samson Properties, Yvonne R Hol... • Samson Properties
Leisure World® of Maryland
![3210 N LEISURE WORLD BLVD 301, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,544 sq ft
|Condo
3210 N LEISURE WORLD BLVD 301, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2258218 • Weichert, REALTORS, Richard D W... • Weichert, REALTORS
Cindy Certified
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Cindy Certified
Leisure World® of Maryland
![15115 INTERLACHEN DR 3-601, SILVER SPRIN..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,115 sq ft
|Condo
15115 INTERLACHEN DR 3-601, SILVER SPRIN...
Community: Leisure World® of Maryland
MLS MDMC2258388 • Real Broker, LLC, James Michael... • 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.
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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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: Oct 09, 2026.
This application does not include information on all of the properties available for sale at this time.
