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Middletown, MD 55+ active adult communities & homes for sale
131 communities near Middletown
489 homes near Middletown
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![The Village at Foxfield]()
$300Ks
- $500Ks
The Village at Foxfield, Middletown, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2012
|
81 homes
5 rating (1 reviews)
![Leisure World® of Marylan...]()
<$100k
- $500Ks
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
- $1Ms
Amblebrook, Gettysburg, PA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
2,000 homes
5 rating (3 reviews)
![Heritage Hunt]()
$600Ks
- $800Ks
Heritage Hunt, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2009
|
1,863 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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(240) 663-8229
5 rating (2 reviews)
![Potomac Green]()
$700Ks
- $800Ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 homes
5 rating (31 reviews)
![Lansdowne Woods of Virgin...]()
$300Ks
- $500Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2017
|
1,200 homes
No reviews yet
![Penn National]()
$200Ks
- $800Ks
Penn National, Fayetteville, PA
New and Resale
|
Age-targeted
|
Built 1968 - present
|
1,100 homes
5 rating (2 reviews)
![Trilogy® at Lake Frederic...]()
$400Ks
- $1Ms
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
5 rating (1 reviews)
![Regency at Dominion Valle...]()
$400Ks
- $800Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2017
|
855 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)
![Four Seasons at Historic ...]()
$600Ks
- $700Ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
801 homes
5 rating (1 reviews)
![Two Rivers]()
$500Ks
- $800Ks
Two Rivers, Odenton, MD
New and Resale
|
55+ age-restricted
|
Built 2015 - present
|
800 homes
No reviews yet
![Cameron Grove]()
$300Ks
- $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
- $600Ks
Central Parke at Victoria..., Laurel, MD
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
609 homes
No reviews yet
![The Woodlands of Urbana]()
$600Ks
- $700Ks
The Woodlands of Urbana, Urbana, MD
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
565 homes
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5 rating (1 reviews)
![Crestwood Village]()
$300Ks
- $300Ks
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
No reviews yet
![Traditions of America at ...]()
$400Ks
- $500Ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
517 homes
No reviews yet
![Carter's Mill]()
$400Ks
- $700Ks
Carter's Mill, Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
480 homes
3 rating (2 reviews)
![Dunbarton]()
$600Ks
- $600Ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 homes
No reviews yet
![The Courtyards at Waverly...]()
$300Ks
- $600Ks
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.
5 rating (1 reviews)
![Carroll Vista]()
$300Ks
- $500Ks
Carroll Vista, Taneytown, MD
Resale Only
|
55+ age-restricted
|
Built 2004 - 2017
|
453 homes
No reviews yet
![Cedar Ridge at Piney Orch...]()
$300Ks
- $400Ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
450 homes
No reviews yet
![Montebello]()
$600Ks
- $1Ms
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
No reviews yet
![Village Crest]()
$400Ks
- $600Ks
Village Crest, Ellicott City, MD
New and Resale
|
55+ age-restricted
|
Built 2005 - 2010
|
406 homes
No reviews yet
![Courtyards at Waverly Woo...]()
$300Ks
- $400Ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2010
|
383 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(240) 663-8229
5 rating (1 reviews)
![Snowden Overlook]()
$400Ks
- $700Ks
Snowden Overlook, Columbia, MD
Resale Only
|
55+ age-restricted
|
Built 2005 - 2010
|
350 homes
No reviews yet
![Creek View]()
$100Ks
- $200Ks
Creek View, Carlisle, PA
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
305 homes
No reviews yet
![Longstown Village]()
$100Ks
- $200Ks
Longstown Village, York, PA
Resale Only
|
Age-targeted
|
Built 1997 - 2000
|
304 homes
No reviews yet
![Heritage at St. Charles]()
$400Ks
- $500Ks
Heritage at St. Charles, White Plains, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
300 homes
No reviews yet
![The Villages At Woodholme]()
$400Ks
- $500Ks
The Villages At Woodholme, Baltimore, MD
Resale Only
|
55+ age-restricted
|
Built 2002 - 2007
|
286 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.
No reviews yet
![Spring Hill]()
$500Ks
- $800Ks
Spring Hill, Lorton, VA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2014
|
282 homes
No reviews yet
![The Enclave at Ellicott H...]()
$400Ks
- $400Ks
The Enclave at Ellicott H..., Ellicott City, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
280 homes
No reviews yet
![Regency at Ashburn]()
$500Ks
- $600Ks
Regency at Ashburn, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2013 - 2020
|
268 homes
No reviews yet
![Emerald Pointe]()
$300Ks
- $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
No reviews yet
![The Crest of Alexandria]()
$900Ks
- $900Ks
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?
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Questions? Call us:
(240) 663-8229
No reviews yet
![Colonial Charles]()
$400Ks
- $400Ks
Colonial Charles, Waldorf, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2018
|
240 homes
No reviews yet
![River Ridge]()
$600Ks
- $600Ks
River Ridge, Woodbridge, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2002
|
238 homes
No reviews yet
![Signature Club at Greenvi...]()
$400Ks
- $900Ks
Signature Club at Greenvi..., New Market, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
233 homes
No reviews yet
![Eden Brook]()
$300Ks
- $300Ks
Eden Brook, Odenton, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
224 homes
No reviews yet
![Roth's Farm Village]()
$200Ks
- $200Ks
Roth's Farm Village, Spring Grove, PA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
224 homes
Winifred Manor
![2013 RUDY SERRA DR 2D, ELDERSBURG, MD, 2..., Eldersburg, MD 21784]()
2 beds
|2 baths
|1,000 sq ft
|Condo
2013 RUDY SERRA DR 2D, ELDERSBURG, MD, 2...
Community: Winifred Manor
MLS MDCR2026992 • Keller Williams Realty Centre, ...
Cedar Ridge at Piney Orchard
![8621 FLUTTERING LEAF TRL 305, ODENTON, M..., Odenton, MD 21113]()
2 beds
|2 baths
|1,500 sq ft
|Condo
8621 FLUTTERING LEAF TRL 305, ODENTON, M...
Community: Cedar Ridge at Piney Orchard
MLS MDAA2122884 • Town Center Realty & Associates...
Leisure World® of Maryland
![3618 GLENEAGLES DR 7-2E, SILVER SPRING, ..., Silver Spring, MD 20906]()
1 beds
|1 baths
|800 sq ft
|Condo
3618 GLENEAGLES DR 7-2E, SILVER SPRING, ...
Community: Leisure World® of Maryland
MLS MDMC2194506 • EXP Realty, LLC, Ailene N Cabal...
Leisure World® of Maryland
![2921 N LEISURE WORLD BLVD APT 418, SILVE..., Silver Spring, MD 20906]()
2 beds
|2 baths
|915 sq ft
|Condo
2921 N LEISURE WORLD BLVD APT 418, SILVE...
Community: Leisure World® of Maryland
MLS MDMC2183290 • Long & Foster Real Estate, Inc....
Central Parke at Victoria Falls
![13401 BELLE CHASSE BLVD 411, LAUREL, MD,..., Laurel, MD 20707]()
2 beds
|2 baths
|1,673 sq ft
|Condo
13401 BELLE CHASSE BLVD 411, LAUREL, MD,...
Community: Central Parke at Victoria Falls
MLS MDPG2148140 • Long & Foster Real Estate, Inc....
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Leisure World® of Maryland
![3200 N LEISURE WORLD BLVD 1017, SILVER S..., Silver Spring, MD 20906]()
3 beds
|2 baths
|1,540 sq ft
|Condo
3200 N LEISURE WORLD BLVD 1017, SILVER S...
Community: Leisure World® of Maryland
MLS MDMC2190660 • EXP Realty, LLC, Karen D Rollin...
Leisure World® of Maryland
![3200 N LEISURE WORLD BLVD APT 512, SILVE..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,260 sq ft
|Condo
3200 N LEISURE WORLD BLVD APT 512, SILVE...
Community: Leisure World® of Maryland
MLS MDMC2193066 • Keller Williams Preferred Prope...
Leisure World® of Maryland
![3200 N LEISURE WORLD BLVD APT 702, SILVE..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,090 sq ft
|Condo
3200 N LEISURE WORLD BLVD APT 702, SILVE...
Community: Leisure World® of Maryland
MLS MDMC2192808 • Weichert, REALTORS, D. Lynn Pug...
Leisure World® of Maryland
![3360 GLENEAGLES DR 71-2B, SILVER SPRING,..., Silver Spring, MD 20906]()
2 beds
|1 baths
|1,200 sq ft
|Condo
3360 GLENEAGLES DR 71-2B, SILVER SPRING,...
Community: Leisure World® of Maryland
MLS MDMC2185812 • Compass, Jordan Beck
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
Heritage Hunt
![7065 HERITAGE HUNT DR 203, GAINESVILLE, ..., Gainesville, VA 20155]()
2 beds
|2 baths
|1,421 sq ft
|Condo
7065 HERITAGE HUNT DR 203, GAINESVILLE, ...
Community: Heritage Hunt
MLS VAPW2106402 • Corcoran McEnearney, Rebecca B ...
Amblebrook
![99 RUSTIC WOOD DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325]()
MLS PAAD2019844 • Keller Williams Keystone Realty...
Penn National
![5985 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222]()
MLS PAFL2029680 • White Rock, Inc., Honor A Kelle...
Four Seasons at Historic Virginia
![16837 FOUR SEASONS DR, DUMFRIES, VA, 220..., Dumfries, VA 22025]()
3 beds
|3 baths
|3,734 sq ft
16837 FOUR SEASONS DR, DUMFRIES, VA, 220...
Community: Four Seasons at Historic Virginia
MLS VAPW2103366 • TTR Sotheby's International Rea...
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Questions? Call us:
(240) 663-8229
Gatherings at Wellington
![9200 CHARLESTON DR 407, MANASSAS, VA, 20..., Manassas, VA 20110]()
3 beds
|2 baths
|2,006 sq ft
|Condo
9200 CHARLESTON DR 407, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2009268 • Samson Properties, Angel M Tigh...
Four Seasons at Historic Virginia
![16453 SPARKLING BROOK LOOP, DUMFRIES, VA..., Dumfries, VA 22025]()
3 beds
|3 baths
|2,468 sq ft
16453 SPARKLING BROOK LOOP, DUMFRIES, VA...
Community: Four Seasons at Historic Virginia
MLS VAPW2104668 • Long & Foster Real Estate, Inc....
Heritage Hunt
![13879 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155]()
MLS VAPW2101280 • Samson Properties, Jordan Muirh...
Heritage Hunt
![13737 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155]()
MLS VAPW2102602 • Corcoran McEnearney, Margarita ...
New
Heritage Hunt
![13516 NORWICK PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155]()
MLS VAPW2105690 • Samson Properties, Natalie H Mc...
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.
Cadence at Lansdowne
![43919 MARITIME SONG TER, LEESBURG, VA, 2..., Leesburg, VA 20176]()
3 beds
|3 baths
|2,396 sq ft
43919 MARITIME SONG TER, LEESBURG, VA, 2...
Community: Cadence at Lansdowne
MLS VALO2103600 • Coldwell Banker Realty, Shelley...
Four Seasons at Virginia Crossing
![3700 HAVERTILL LN # 1201, WOODBRIDGE, VA..., Woodbridge, VA 22193]()
2 beds
|2 baths
|1,415 sq ft
|Condo
3700 HAVERTILL LN # 1201, WOODBRIDGE, VA...
Community: Four Seasons at Virginia Crossing
MLS VAPW2105328 • Samson Properties, Christopher ...
Four Seasons at Virginia Crossing
![13950 ENGLEFIELD DR 3202, WOODBRIDGE, VA..., Woodbridge, VA 22193]()
2 beds
|3 baths
|1,811 sq ft
|Condo
13950 ENGLEFIELD DR 3202, WOODBRIDGE, VA...
Community: Four Seasons at Virginia Crossing
MLS VAPW2102276 • Compass, Jordan Beck
Gatherings at Potomac Station
![750 MOUNT AIRY TER NE UNIT 206, LEESBURG..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,532 sq ft
|Condo
750 MOUNT AIRY TER NE UNIT 206, LEESBURG...
Community: Gatherings at Potomac Station
MLS VALO2106434 • Pearson Smith Realty, LLC, Vick...
Gatherings at Potomac Station
![750 MOUNT AIRY TER NE UNIT 304, LEESBURG..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,532 sq ft
|Condo
750 MOUNT AIRY TER NE UNIT 304, LEESBURG...
Community: Gatherings at Potomac Station
MLS VALO2109338 • Pearson Smith Realty, LLC, Vick...
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Gatherings at Potomac Station
![700 MOUNT AIRY TER NE UNIT 403, LEESBURG..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,410 sq ft
|Condo
700 MOUNT AIRY TER NE UNIT 403, LEESBURG...
Community: Gatherings at Potomac Station
MLS VALO2106436 • Pearson Smith Realty, LLC, Vick...
Gatherings at Potomac Station
![750 MOUNT AIRY TER NE UNIT 403, LEESBURG..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,410 sq ft
|Condo
750 MOUNT AIRY TER NE UNIT 403, LEESBURG...
Community: Gatherings at Potomac Station
MLS VALO2107250 • Pearson Smith Realty, LLC, Vick...
The Retreat at Poland Hill
![43441 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152]()
4 beds
|4 baths
|3,553 sq ft
43441 BETTYS FARM DR, CHANTILLY, VA, 201...
Community: The Retreat at Poland Hill
MLS VALO2107850 • Metro House, Lizzie A Helmig
New
Trilogy® at Lake Frederick
![105 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|2,700 sq ft
105 CABBAGE WHITE DR, LAKE FREDERICK, VA...
Community: Trilogy® at Lake Frederick
MLS VAFV2037560 • EXP Realty, LLC, Thu-Nguyet Thi...
Heritage Hunt
![6868 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2104596 • Samson Properties, Earnest W Go...
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
![108 BUNTING CT, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|5,284 sq ft
108 BUNTING CT, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2035860 • Keller Williams Realty, Matt Bo...
Regency at Dominion Valley
![15691 ALDERBROOK DR, HAYMARKET, VA, 2016..., Haymarket, VA 20169]()
2 beds
|3 baths
|4,124 sq ft
15691 ALDERBROOK DR, HAYMARKET, VA, 2016...
Community: Regency at Dominion Valley
MLS VAPW2105100 • KW Metro Center, Joshua Mathews
Trilogy® at Lake Frederick
![102 PHOEBE CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
5 beds
|4 baths
|4,267 sq ft
102 PHOEBE CT, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2036120 • Keller Williams Realty, Matt Bo...
Trilogy® at Lake Frederick
![105 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|1,962 sq ft
105 BAYHILL TER, LAKE FREDERICK, VA, 226...
Community: Trilogy® at Lake Frederick
MLS VAFV2036228 • RE/MAX Roots, David K Spence
Regency at Dominion Valley
![5320 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
4 beds
|3 baths
|3,082 sq ft
5320 TREVINO DR, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2104912 • RE/MAX Gateway, LLC, Charlet H ...
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Regency at Dominion Valley
![5108 PEYTON CHAPEL DR, HAYMARKET, VA, 20..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,782 sq ft
5108 PEYTON CHAPEL DR, HAYMARKET, VA, 20...
Community: Regency at Dominion Valley
MLS VAPW2104258 • RE/MAX Gateway, Christy Brocket...
Potomac Green
![20831 ADAMS MILL PL, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2106416 • Long & Foster Real Estate, Inc....
Four Seasons at Ashburn Village
![44485 CHAMBERLAIN TER UNIT 200, ASHBURN,..., Ashburn, VA 20147]()
2 beds
|2 baths
|1,763 sq ft
|Condo
44485 CHAMBERLAIN TER UNIT 200, ASHBURN,...
Community: Four Seasons at Ashburn Village
MLS VALO2106714 • Century 21 Redwood Realty, Fran...
Trilogy® at Lake Frederick
![103 BURKWOOD TER, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,376 sq ft
103 BURKWOOD TER, LAKE FREDERICK, VA, 22...
Community: Trilogy® at Lake Frederick
MLS VAFV2036998 • RE/MAX Roots, Sheila R Pack
The Atrium at MetroWest
![2960 VADEN DR # 2-406, FAIRFAX, VA, 2203..., Fairfax, VA 22031]()
2 beds
|2 baths
|1,391 sq ft
|Condo
2960 VADEN DR # 2-406, FAIRFAX, VA, 2203...
Community: The Atrium at MetroWest
MLS VAFX2274800 • Pearson Smith Realty, LLC, Jiun...
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?
489
homes
near Middletown
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© 2025 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 24, 2025.
This application does not include information on all of the properties available for sale at this time.
