Call us at (240) 663-8229 to learn more about active adult communities near Middletown
Middletown, MD 55+ active adult communities & homes for sale
133 communities near Middletown
440 homes near Middletown
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$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
- $500Ks
Amblebrook, Gettysburg, PA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
2,000 homes
5 rating (3 reviews)
![Heritage Hunt]()
$400Ks
- $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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5 rating (2 reviews)
![Potomac Green]()
$600Ks
- $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
- $400Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2017
|
1,200 homes
$200Ks
- $600Ks
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
- $700Ks
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
Four Seasons at Historic ..., Dumfries, VA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
801 homes
5 rating (1 reviews)
![Two Rivers]()
$500Ks
- $700Ks
Two Rivers, Odenton, MD
New and Resale
|
55+ age-restricted
|
Built 2015 - present
|
800 homes
$200Ks
- $500Ks
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
$600Ks
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
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
$500Ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
517 homes
$400Ks
- $700Ks
Carter's Mill, Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
480 homes
3 rating (2 reviews)
![Dunbarton]()
$600Ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 homes
$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
$300Ks
- $400Ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
450 homes
$600Ks
- $1Ms
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
$300Ks
- $400Ks
Village Crest, Ellicott City, MD
New and Resale
|
55+ age-restricted
|
Built 2005 - 2010
|
406 homes
$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:
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5 rating (1 reviews)
![Snowden Overlook]()
$400Ks
- $700Ks
Snowden Overlook, Columbia, MD
Resale Only
|
55+ age-restricted
|
Built 2005 - 2010
|
350 homes
$100Ks
- $200Ks
Creek View, Carlisle, PA
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
305 homes
$100Ks
- $200Ks
Longstown Village, York, PA
Resale Only
|
Age-targeted
|
Built 1997 - 2000
|
304 homes
$400Ks
Heritage at St. Charles, White Plains, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
300 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
The Villages At Woodholme, Baltimore, MD
Resale Only
|
55+ age-restricted
|
Built 2002 - 2007
|
286 homes
$500Ks
- $800Ks
Spring Hill, Lorton, VA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2014
|
282 homes
$300Ks
- $600Ks
The Enclave at Ellicott H..., Ellicott City, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
280 homes
$800Ks
- $900Ks
Regency at Ashburn, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2013 - 2020
|
268 homes
$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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(240) 663-8229
$300Ks
- $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$400Ks
Colonial Charles, Waldorf, MD
Resale Only
|
55+ age-restricted
|
Built 2006 - 2018
|
240 homes
$500Ks
- $700Ks
River Ridge, Woodbridge, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2002
|
238 homes
$400Ks
- $900Ks
Signature Club at Greenvi..., New Market, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
233 homes
Carroll Vista
![101 BUTTERFLY DR # 106, TANEYTOWN, MD, 2..., Taneytown, MD 21787]()
2 beds
|2 baths
|1,410 sq ft
|Condo
101 BUTTERFLY DR # 106, TANEYTOWN, MD, 2...
Community: Carroll Vista
MLS MDCR2029168 • Berkshire Hathaway HomeServices...
Two Rivers
![1508 ORCHARD GRASS CT, ODENTON, MD, 2111..., Odenton, MD 21113]()
MLS MDAA2126024 • Realty Navigator, Petra Quinn
Carroll Vista
![17 HAYRIDE LN # 204, TANEYTOWN, MD, 2178..., Taneytown, MD 21787]()
3 beds
|3 baths
|3,130 sq ft
|Condo
17 HAYRIDE LN # 204, TANEYTOWN, MD, 2178...
Community: Carroll Vista
MLS MDCR2031360 • Berkshire Hathaway HomeServices...
Leisure World® of Maryland
![3630 GLENEAGLES DR 8-2B, SILVER SPRING, ..., Silver Spring, MD 20906]()
1 beds
|1 baths
|800 sq ft
|Condo
3630 GLENEAGLES DR 8-2B, SILVER SPRING, ...
Community: Leisure World® of Maryland
MLS MDMC2200936 • Weichert, REALTORS, Marilyn E G...
Leisure World® of Maryland
![15115 INTERLACHEN DR 3-308, SILVER SPRIN..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,115 sq ft
|Condo
15115 INTERLACHEN DR 3-308, SILVER SPRIN...
Community: Leisure World® of Maryland
MLS MDMC2206898 • Weichert, REALTORS, Catherine M...
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Two Rivers
![2630 DRAGON FLY WAY, ODENTON, MD, 21113, Odenton, MD 21113]()
2 beds
|2 baths
|1,668 sq ft
|Condo
2630 DRAGON FLY WAY, ODENTON, MD, 21113
Community: Two Rivers
MLS MDAA2131174 • The Real Estate Experts, Darren...
Cedar Ridge at Piney Orchard
![8600 ROAMING RIDGE WAY UNIT 106, ODENTON..., Odenton, MD 21113]()
2 beds
|2 baths
|1,600 sq ft
|Condo
8600 ROAMING RIDGE WAY UNIT 106, ODENTON...
Community: Cedar Ridge at Piney Orchard
MLS MDAA2124846 • CENTURY 21 New Millennium, Mary...
Leisure World® of Maryland
![3330 N LEISURE WORLD BLVD 5-604, SILVER ..., Silver Spring, MD 20906]()
3 beds
|3 baths
|1,530 sq ft
|Condo
3330 N LEISURE WORLD BLVD 5-604, SILVER ...
Community: Leisure World® of Maryland
MLS MDMC2208048 • RLAH @properties, Larry B Priga...
The Village at Freedom Hills
![13946 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740]()
2 beds
|2 baths
|1,484 sq ft
13946 PATRIOT WAY, HAGERSTOWN, MD, 21740
Community: The Village at Freedom Hills
MLS MDWA2032664 • Samson Properties, Megan Harnis...
The Village at Cabin Branch
![13210 PETREL ST UNIT 3304, CLARKSBURG, M..., Clarksburg, MD 20871]()
2 beds
|2 baths
|1,529 sq ft
|Condo
13210 PETREL ST UNIT 3304, CLARKSBURG, M...
Community: The Village at Cabin Branch
MLS MDMC2132350 • Keller Williams Realty Centre, ...
Download the Ultimate 55+ Homebuying Guide
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Gatherings at Cabin Branch
![13210 PETREL ST UNIT 3304, CLARKSBURG, M..., Clarksburg, MD 20871]()
2 beds
|2 baths
|1,529 sq ft
|Condo
13210 PETREL ST UNIT 3304, CLARKSBURG, M...
Community: Gatherings at Cabin Branch
MLS MDMC2132350 • Keller Williams Realty Centre, ...
Cameron Grove
![14040 NEW ACADIA LN APT 406, UPPER MARLB..., Upper Marlboro, MD 20774]()
2 beds
|2 baths
|1,280 sq ft
|Condo
14040 NEW ACADIA LN APT 406, UPPER MARLB...
Community: Cameron Grove
MLS MDPG2182960 • Samson Properties, Aisha Holmes
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 MDFR2071582 • IMPACT Maryland Real Estate, St...
Signature Club at Greenview
![5810 WHITEROSE WAY, NEW MARKET, MD, 2177..., New Market, MD 21774]()
3 beds
|4 baths
|2,410 sq ft
5810 WHITEROSE WAY, NEW MARKET, MD, 2177...
Community: Signature Club at Greenview
MLS MDFR2072088 • Century 21 Redwood Realty, Mich...
Leisure World® of Maryland
![2921 N LEISURE WORLD BLVD 1-316, SILVER ..., Silver Spring, MD 20906]()
1 beds
|2 baths
|803 sq ft
|Condo
2921 N LEISURE WORLD BLVD 1-316, SILVER ...
Community: Leisure World® of Maryland
MLS MDMC2206918 • Nitro Realty, Megan A. Cardenas
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Leisure World® of Maryland
![3005 S LEISURE WORLD BLVD APT 209, SILVE..., Silver Spring, MD 20906]()
1 beds
|1 baths
|885 sq ft
|Condo
3005 S LEISURE WORLD BLVD APT 209, SILVE...
Community: Leisure World® of Maryland
MLS MDMC2204876 • Samson Properties, Robert J Che...
Leisure World® of Maryland
![2 FINSBURY PARK CT # 47-A, SILVER SPRING..., Silver Spring, MD 20906]()
3 beds
|2 baths
|1,193 sq ft
|Condo
2 FINSBURY PARK CT # 47-A, SILVER SPRING...
Community: Leisure World® of Maryland
MLS MDMC2198546 • Keller Williams Realty Centre, ...
Village Crest
![8135 CYPRUS CEDAR LN K, ELLICOTT CITY, M..., Ellicott City, MD 21043]()
2 beds
|2 baths
|1,330 sq ft
|Condo
8135 CYPRUS CEDAR LN K, ELLICOTT CITY, M...
Community: Village Crest
MLS MDHW2061348 • Keller Williams Lucido Agency, ...
Leisure World® of Maryland
![2901 S LEISURE WORLD BLVD 304, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,229 sq ft
|Condo
2901 S LEISURE WORLD BLVD 304, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2204244 • Weichert, REALTORS, Deborah A Y...
Leisure World® of Maryland
![3500 FOREST EDGE DR 15-2E, SILVER SPRING..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,157 sq ft
|Condo
3500 FOREST EDGE DR 15-2E, SILVER SPRING...
Community: Leisure World® of Maryland
MLS MDMC2196962 • Long & Foster Real Estate, Inc....
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.
Carroll Vista
![840 HORSESHOE LN # 171, TANEYTOWN, MD, 2..., Taneytown, MD 21787]()
3 beds
|3 baths
|1,707 sq ft
|Condo
840 HORSESHOE LN # 171, TANEYTOWN, MD, 2...
Community: Carroll Vista
MLS MDCR2027344 • Berkshire Hathaway HomeServices...
Leisure World® of Maryland
![3310 N LEISURE WORLD BLVD 627, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,138 sq ft
|Condo
3310 N LEISURE WORLD BLVD 627, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2207872 • Samson Properties, Sharlene C M...
Leisure World® of Maryland
![15210 ELKRIDGE WAY 91-3K, SILVER SPRING,..., Silver Spring, MD 20906]()
3 beds
|2 baths
|1,340 sq ft
|Condo
15210 ELKRIDGE WAY 91-3K, SILVER SPRING,...
Community: Leisure World® of Maryland
MLS MDMC2208290 • EXP Realty, LLC, Kathleen M Wor...
Leisure World® of Maryland
![3200 N LEISURE WORLD BLVD 918, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,315 sq ft
|Condo
3200 N LEISURE WORLD BLVD 918, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2201596 • Keller Williams Capital Propert...
Leisure World® of Maryland
![15300 BEAVERBROOK CT 88-2B, SILVER SPRIN..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,043 sq ft
|Condo
15300 BEAVERBROOK CT 88-2B, SILVER SPRIN...
Community: Leisure World® of Maryland
MLS MDMC2180836 • Wallach Realty, Howard Wallach
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Ellicott's Retreat
![8911 CARLS CT Q, ELLICOTT CITY, MD, 2104..., Ellicott City, MD 21043]()
2 beds
|2 baths
|1,624 sq ft
|Condo
8911 CARLS CT Q, ELLICOTT CITY, MD, 2104...
Community: Ellicott's Retreat
MLS MDHW2061868 • Realty ONE Group Capital, Sarah...
Leisure World® of Maryland
![3350 GLENEAGLES DR 70-1D, SILVER SPRING,..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,308 sq ft
|Condo
3350 GLENEAGLES DR 70-1D, SILVER SPRING,...
Community: Leisure World® of Maryland
MLS MDMC2207442 • Compass, Merilee B Paran
Liberty Place
![42 LIBERTY RD D, SYKESVILLE, MD, 21784, Sykesville, MD 21784]()
2 beds
|2 baths
|1,554 sq ft
|Condo
42 LIBERTY RD D, SYKESVILLE, MD, 21784
Community: Liberty Place
MLS MDCR2030436 • IMPACT Maryland Real Estate, St...
Winifred Manor
![2016 RUDY SERRA DR C, SYKESVILLE, MD, 21..., Sykesville, MD 21784]()
MLS MDCR2029846 • Cummings & Co. Realtors, Jason ...
Leisure World® of Maryland
![3210 N LEISURE WORLD BLVD APT 610, SILVE..., Silver Spring, MD 20906]()
3 beds
|2 baths
|1,550 sq ft
|Condo
3210 N LEISURE WORLD BLVD APT 610, SILVE...
Community: Leisure World® of Maryland
MLS MDMC2206038 • Long & Foster Real Estate, Inc....
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 Villages At Woodholme
![8402 PRAIRIE ROSE PL # 8402, PIKESVILLE,..., Pikesville, MD 21208]()
3 beds
|4 baths
|3,800 sq ft
|Condo
8402 PRAIRIE ROSE PL # 8402, PIKESVILLE,...
Community: The Villages At Woodholme
MLS MDBC2136022 • EXP Realty, LLC, Teal Clise
Cedar Ridge at Piney Orchard
![8615 FLUTTERING LEAF TRL 404, ODENTON, M..., Odenton, MD 21113]()
2 beds
|2 baths
|1,500 sq ft
|Condo
8615 FLUTTERING LEAF TRL 404, ODENTON, M...
Community: Cedar Ridge at Piney Orchard
MLS MDAA2119924 • Long & Foster Real Estate, Inc....
Watershed
![1202 CRESTED WOOD DR, LAUREL, MD, 20724, Laurel, MD 20724]()
MLS MDAA2103848 • Realty 1 Maryland, LLC, Un H Mc...
Central Parke at Victoria Falls
![13801 BELLE CHASSE BLVD 212, LAUREL, MD,..., Laurel, MD 20707]()
2 beds
|2 baths
|1,673 sq ft
|Condo
13801 BELLE CHASSE BLVD 212, LAUREL, MD,...
Community: Central Parke at Victoria Falls
MLS MDPG2162900 • Long & Foster Real Estate, Inc....
Central Parke at Victoria Falls
![13501 BELLE CHASSE BLVD 215, LAUREL, MD,..., Laurel, MD 20707]()
2 beds
|2 baths
|1,919 sq ft
|Condo
13501 BELLE CHASSE BLVD 215, LAUREL, MD,...
Community: Central Parke at Victoria Falls
MLS MDPG2181148 • Long & Foster Real Estate, Inc....
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Leisure World® of Maryland
![3310 N LEISURE WORLD BLVD 124, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,195 sq ft
|Condo
3310 N LEISURE WORLD BLVD 124, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2197148 • The Agency DC, Alejandro Luis A...
Liberty Place
![40 LIBERTY RD T, SYKESVILLE, MD, 21784, Sykesville, MD 21784]()
2 beds
|2 baths
|1,186 sq ft
|Condo
40 LIBERTY RD T, SYKESVILLE, MD, 21784
Community: Liberty Place
MLS MDCR2030664 • RE/MAX Advantage Realty, Mark C...
Gatherings at Cabin Branch
![13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871]()
3 beds
|3 baths
|1,590 sq ft
13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Community: Gatherings at Cabin Branch
MLS MDMC2204722 • King Real Estate, Inc, David N ...
The Village at Cabin Branch
![13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871]()
3 beds
|3 baths
|1,590 sq ft
13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Community: The Village at Cabin Branch
MLS MDMC2204722 • King Real Estate, Inc, David N ...
Leisure World® of Maryland
![2901 S LEISURE WORLD BLVD 524, SILVER SP..., Silver Spring, MD 20906]()
2 beds
|2 baths
|1,218 sq ft
|Condo
2901 S LEISURE WORLD BLVD 524, SILVER SP...
Community: Leisure World® of Maryland
MLS MDMC2207358 • Long & Foster Real Estate, Inc....
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?
440
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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.
© 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: Dec 10, 2025.
This application does not include information on all of the properties available for sale at this time.
