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Middletown, CT 55+ active adult communities & homes for sale - Page 4
124 communities near Middletown
181 homes near Middletown
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5 rating (3 reviews)
![Founders Ridge]()
$500Ks
- $600Ks
Founders Ridge, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
75 homes
$200Ks
- $400Ks
Bartlett Hollow, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2015 - present
|
25 homes
3.6 rating (7 reviews)
![Heritage Village]()
$200Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
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$600Ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
$400Ks
- $600Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
$500Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 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.
$1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
5 rating (2 reviews)
![Fairfield at St. James]()
$400Ks
- $500Ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
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$200Ks
- $300Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $200Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
$500Ks
- $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 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
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$400Ks
- $500Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$400Ks
- $500Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
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4.6 rating (9 reviews)
![Meadowbrook Pointe Links ...]()
$300Ks
- $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
280 homes
4 rating (1 reviews)
![Vineyards at Blue Point]()
$800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
$500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
$800Ks
- $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 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
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$700Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
$600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$600Ks
- $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
228 homes
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$400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
5 rating (1 reviews)
![Sunrise Village]()
$400Ks
- $500Ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 homes
$400Ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 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
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
|
195 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
$700Ks
The Seasons at East North..., East Northport, NY
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
190 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900Ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 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)
![The Villages at Mount Sin...]()
$500Ks
- $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
Spring Lake Village
![889 GLACIER WAY # 889, SOUTHINGTON, CT, ..., Southington, CT 06489]()
3 beds
|2 baths
|1,923 sq ft
|Condo
889 GLACIER WAY # 889, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24144794 • Putnam Agency Real Estate LLC, Reb...
New
Long Hill Village
![4 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611]()
MLS 24145342 • Higgins Group Real Estate, Fredda ...
New
Spring Lake Village
![951 SWEETHEART PATH # 951, SOUTHINGTON, ..., Southington, CT 06489]()
2 beds
|3 baths
|1,550 sq ft
|Condo
951 SWEETHEART PATH # 951, SOUTHINGTON, ...
Community: Spring Lake Village
MLS 24147109 • Evjen Agency, Heidi Matusik
Newtown Woods
![433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470]()
2 beds
|2 baths
|1,504 sq ft
|Condo
433 BROOKSIDE CT 433, NEWTOWN, CT, 06470
Community: Newtown Woods
MLS 24139490 • Coldwell Banker Realty, Linda McCa...
Oronoque Village
![164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,175 sq ft
|Condo
164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24139444 • Stacy Blake Realty LLC, Celina Cuo...
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New
The Village at Oxford Greens
![520 TRADITIONS CT N # 520, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|2 baths
|1,590 sq ft
|Condo
520 TRADITIONS CT N # 520, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24146963 • William Raveis Real Estate, Debora...
Oronoque Village
![617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,438 sq ft
|Condo
617 CHEROKEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24146302 • William Raveis Real Estate, Kenny ...
Heritage Village
![825 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
825 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24124224 • Keller Williams Realty, Donna Doyl...
Fieldstone Village
![323 GOOSE LN # 323, ORANGE, CT, 06477, Orange, CT 06477]()
3 beds
|4 baths
|1,962 sq ft
|Condo
323 GOOSE LN # 323, ORANGE, CT, 06477
Community: Fieldstone Village
MLS 24146329 • Coldwell Banker Realty, Allen Grea...
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.
Heritage Village
![114 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
114 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24128139 • Telesh Realty LLC, Igor Teleshevsk...
Evergreen
![34 WOODSBORO CIR # 34, CROMWELL, CT, 064..., Cromwell, CT 06416]()
2 beds
|2 baths
|1,758 sq ft
|Condo
34 WOODSBORO CIR # 34, CROMWELL, CT, 064...
Community: Evergreen
MLS 24134359 • Century 21 North East, Joselyn Val...
Oronoque Village
![488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,438 sq ft
|Condo
488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24134368 • Higgins Group Real Estate, Carmen ...
Oronoque Village
![195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,575 sq ft
|Condo
195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24128861 • Property Choices Real Estate, Paul...
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Heritage Village
![331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
331 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24143592 • Coldwell Banker Realty, Pamela Dos...
The Village at Oxford Greens
![930 TILLINGHAST DR # 930, OXFORD, CT, 06..., Oxford, CT 06478]()
2 beds
|3 baths
|2,365 sq ft
930 TILLINGHAST DR # 930, OXFORD, CT, 06...
Community: The Village at Oxford Greens
MLS 24137749 • Real Estate Two, Karen Berwick
Heritage Village
![701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137961 • Coldwell Banker Realty, Claudia Fo...
New
Spring Lake Village
![1 COACH DR # 1, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
2 beds
|2 baths
|1,323 sq ft
|Condo
1 COACH DR # 1, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24147367 • Berkshire Hathaway NE Prop., Jacek...
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.
Heritage Village
![740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24116195 • William Raveis Real Estate, Daniel...
Regency at Woodbridge
![8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT...
Community: Regency at Woodbridge
MLS 24145805 • Thomas Jacovino, Kathy Childs
Heritage Village
![953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
953 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24142233 • Realty ONE Group Connect, Paul Duh
Spring Lake Village
![621 OVERLOOK PATH # 621, SOUTHINGTON, CT..., Southington, CT 06489]()
2 beds
|3 baths
|1,133 sq ft
|Condo
621 OVERLOOK PATH # 621, SOUTHINGTON, CT...
Community: Spring Lake Village
MLS 24146494 • eXp Realty, Mark Mermelstein
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Heritage Village
![917 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
917 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24145119 • Joseph Bette REALTORS Inc, Cynthia...
Heritage Village
![568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
568A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24129707 • Showcase Realty, Inc., Jeff Colt
Oronoque Village
![289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,620 sq ft
|Condo
289 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24138784 • Oronoque Real Estate, Monica Dalto...
Oronoque Village
![87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,454 sq ft
|Condo
87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24140020 • Oronoque Real Estate, Monica Dalto...
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.
Oronoque Village
![383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,360 sq ft
|Condo
383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24140690 • Coldwell Banker Realty, Mary Kelle...
Heritage Village
![902 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
902 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24126334 • Joseph Bette REALTORS Inc, Justin ...
Heritage Village
![191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24122871 • Joseph Bette REALTORS Inc, Justin ...
Oronoque Village
![522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
3 beds
|3 baths
|1,426 sq ft
|Condo
522 IROQUOIS LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24141511 • Fairfield County Real Estate, Terr...
Heritage Village
![123 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
123 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24145278 • Independent Realty Group, Tammi Li...
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Park Glen
![1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776, New Milford, CT 06776]()
2 beds
|2 baths
|1,880 sq ft
|Condo
1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776
Community: Park Glen
MLS 24135079 • W. Raveis Lifestyles Realty, Austi...
Oronoque Village
![133 BANNOCK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
3 beds
|3 baths
|1,438 sq ft
|Condo
133 BANNOCK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24142372 • Coldwell Banker Realty, Mark Pires
Heritage Village
![39 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
39 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24139075 • William Raveis Real Estate, Ruth Z...
The Woods at Dunham Pond
![12 HERON VIEW RD # 12, NEW FAIRFIELD, CT..., New Fairfield, CT 06812]()
1 beds
|2 baths
|1,550 sq ft
12 HERON VIEW RD # 12, NEW FAIRFIELD, CT...
Community: The Woods at Dunham Pond
MLS 24136009 • Santana Realty Group LLC, Victor S...
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 Village at Buckingham
![8 KENINGTON RD # 8, AVON, CT, 06001, Avon, CT 06001]()
3 beds
|3 baths
|2,430 sq ft
|Condo
8 KENINGTON RD # 8, AVON, CT, 06001
Community: The Village at Buckingham
MLS 24142060 • Berkshire Hathaway NE Prop., Becky...
Heritage Village
![7 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,447 sq ft
|Condo
7 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24136069 • Showcase Realty, Inc., Darlene Gel...
Bidwell Village
![94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ..., Coventry, CT 06238]()
3 beds
|3 baths
|1,717 sq ft
94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ...
Community: Bidwell Village
MLS 24128107 • ERA Blanchard & Rossetto, Cheri Tr...
Heritage Village
![761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,063 sq ft
|Condo
761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24135987 • Scalzo Real Estate, Stephanie Chap...
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Heritage Village
![865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24138526 • Showcase Realty, Inc., Gregory Bal...
Heritage Village
![25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,447 sq ft
|Condo
25 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24140617 • Berkshire Hathaway NE Prop., Kathy...
Frequently Asked Questions
In Middletown, there are no large communities, no medium communities, and 3 small communities with less than 500 homes.
The smallest 55+ communities in Middletown has 25 homes, the largest has 75 homes, and the average communities consists of 56 homes.
Yes, there are new 55+ homes available in Middletown. The most recent communities started in Middletown include Founders Ridge, Bartlett Hollow, Sonoma Woods. There are also 2 communities in Middletown that offer new construction homes, including Bartlett Hollow, Founders Ridge.
Yes, there is gated 55+ communities in Middletown. Approximately 33.3% of 55+ communities in the area are gated. For instance, Bartlett Hollow is a gated communities with 25 homes.
On average, listings in 55+ communities in Middletown stay on the market for around 237 days. The average price of homes for sale in these communities is approximately $577,386, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Sonoma Woods average around $649,900, while homes in Bartlett Hollow average around $579,139.
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: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.
