Call us at (860) 238-3620 to learn more about active adult communities near Winchester Area
Winchester Area, CT 55+ active adult communities & homes for sale - Page 2
92 communities near Winchester Area
246 homes near Winchester Area
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![O'Meara Farm]()
$400Ks
- $500Ks
O'Meara Farm, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 1998 - 2005
|
104 homes
No reviews yet
![The Bridges at Oxford Gre...]()
$600Ks
- $600Ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
99 homes
No reviews yet
![Liberty at Newtown]()
$300Ks
- $400Ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
No reviews yet
![Applegate Estates]()
$500Ks
- $400Ks
Applegate Estates, Southington, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - 2025
|
94 homes
No reviews yet
![Founders Village]()
$500Ks
- $600Ks
Founders Village, Southold, NY
Resale Only
|
55+ age-restricted
|
Built 1981 - 1985
|
92 homes
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No reviews yet
![Pond Spring Village]()
$300Ks
- $300Ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 homes
No reviews yet
![The Vineyards at Mount Si...]()
$800Ks
- $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
91 homes
No reviews yet
![Glassbury Court at Cold S...]()
$500Ks
- $700Ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
5 rating (1 reviews)
![Paris Square]()
$400Ks
- $700Ks
Paris Square, Northvale, NJ
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
88 homes
No reviews yet
![Castle Heights of Cheshir...]()
$500Ks
- $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 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
![The Vineyards at Miller P...]()
$600Ks
- $600Ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
85 homes
No reviews yet
![Bartlett Hill]()
$500Ks
- $500Ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
82 homes
No reviews yet
![Baldwin Station]()
$400Ks
- $400Ks
Baldwin Station, Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2001 - 2003
|
82 homes
5 rating (2 reviews)
![Benson Woods]()
$400Ks
- $600Ks
Benson Woods, Middlebury, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
79 homes
No reviews yet
![Shaker Heights]()
$400Ks
- $500Ks
Shaker Heights, Enfield, CT
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
77 homes
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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
No reviews yet
![Long Hill Village]()
$300Ks
- $400Ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 homes
No reviews yet
![Regency at Woodbridge]()
$600Ks
- $700Ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
No reviews yet
![The Village at Hunt Glen]()
$300Ks
- $300Ks
The Village at Hunt Glen, Granby, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
69 homes
No reviews yet
![Sonoma Woods]()
$300Ks
- $300Ks
Sonoma Woods, Middletown, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2015
|
68 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
![Stoneleigh Woods at Carme...]()
$400Ks
- $400Ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2012 - 2017
|
68 homes
No reviews yet
![Hopmeadow Place]()
$200Ks
- $300Ks
Hopmeadow Place, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
66 homes
No reviews yet
![Glassbury Court at Hunter...]()
$500Ks
- $700Ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2014
|
64 homes
No reviews yet
![Whitney Glen]()
$500Ks
- $600Ks
Whitney Glen, Westport, CT
Resale Only
|
55+ age-restricted
|
Built 1982 - 1982
|
62 homes
No reviews yet
![RiverWalk]()
$500Ks
- $600Ks
RiverWalk, Branford, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
60 homes
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Questions? Call us:
(860) 238-3620
No reviews yet
![Woodcrest at Jacobs Hill]()
$300Ks
- $300Ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2006
|
58 homes
No reviews yet
![The Village at Buckingham]()
$500Ks
- $600Ks
The Village at Buckingham, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
56 homes
No reviews yet
![The Atrium of Portland]()
<$100k
- $100Ks
The Atrium of Portland, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2004
|
56 homes
No reviews yet
![Autumn Fields]()
$200Ks
- $300Ks
Autumn Fields, Enfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2006
|
56 homes
No reviews yet
![77 Sunset Lane]()
$400Ks
- $700Ks
77 Sunset Lane, Ridgefield, CT
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
54 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
![Evergreen]()
$400Ks
- $500Ks
Evergreen, Cromwell, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
52 homes
No reviews yet
![Regency Meadows]()
$500Ks
- $500Ks
Regency Meadows, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
51 homes
No reviews yet
![Gloria Commons]()
$400Ks
- $400Ks
Gloria Commons, Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2015
|
50 homes
No reviews yet
![Villas at Seminary Hill]()
$400Ks
- $400Ks
Villas at Seminary Hill, Carmel, NY
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
50 homes
No reviews yet
![The Residences at Butterf...]()
$500Ks
- $600Ks
The Residences at Butterf..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2023
|
49 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
No reviews yet
![Bramble Ridge]()
$400Ks
- $500Ks
Bramble Ridge, Suffield, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2015
|
47 homes
No reviews yet
![Chimney Hill]()
$500Ks
- $700Ks
Chimney Hill, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
44 homes
No reviews yet
![Village Vistas]()
$800Ks
- $1Ms
Village Vistas, Port Jefferson, NY
Resale Only
|
55+ age-restricted
|
Built 2013 - 2017
|
43 homes
No reviews yet
![Forest Mews]()
$300Ks
- $400Ks
Forest Mews, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
40 homes
No reviews yet
![Bidwell Village]()
$300Ks
- $400Ks
Bidwell Village, Coventry, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
37 homes
New
Stoneleigh Woods at Riverhead
![4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|2,175 sq ft
|Condo
4 HAVERTON CT, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 928263 • Exit Realty Liberty, Maureen A. Kler...
New
Leisure Village
![280 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 927775 • Coldwell Banker M&D Good Life, Micha...
Leisure Village
![65 ENFIELD CT UNIT A A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
65 ENFIELD CT UNIT A A, RIDGE, NY, 11961
Community: Leisure Village
MLS 926534 • Leisure Living Realty Inc, Laura Ruh...
Heritage Hills
![348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,428 sq ft
|Condo
348 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 925161 • William Raveis Real Estate, Cynthia ...
Jefferson Village
![2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10..., Yorktown Heights, NY 10598]()
1 beds
|1 baths
|800 sq ft
|Condo
2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10...
Community: Jefferson Village
MLS 902554 • Houlihan Lawrence Inc., Jo-Ella Deli...
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
Leisure Village
![98 A EASTBOURNE, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,486 sq ft
|Condo
98 A EASTBOURNE, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 906713 • Coldwell Banker American Homes, Mary...
Leisure Knoll
![190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 863784 • Coldwell Banker American Homes, Bonn...
Overlook
![1019 COTTAGE DR # 9, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 923664 • Toll Brothers Real Estate Inc., Thom...
Overlook
![4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512]()
3 beds
|3 baths
|1,914 sq ft
|Condo
4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...
Community: Overlook
MLS 925922 • Toll Brothers Real Estate Inc., Thom...
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 Hills
![504 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,483 sq ft
|Condo
504 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 919796 • Houlihan Lawrence Inc., Linda Crispi...
New
Heritage Hills
![688 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,909 sq ft
|Condo
688 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 928674 • Houlihan Lawrence Inc., Karen Fixler
Leisure Knoll
![147 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 904637 • Howard Hanna Coach, Kalliopi C. Suar...
Overlook
![1042 COTTAGE DR # 25, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 911920 • Toll Brothers Real Estate Inc., Thom...
Overlook
![4057 FAIRWAYS DR # 129, CARMEL, NY, 1051..., Carmel, NY 10512]()
3 beds
|4 baths
|2,131 sq ft
|Condo
4057 FAIRWAYS DR # 129, CARMEL, NY, 1051...
Community: Overlook
MLS 902722 • Toll Brothers Real Estate Inc., Thom...
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
Overlook
![1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 889837 • Toll Brothers Real Estate Inc., Thom...
Overlook
![1040 COTTAGE DR # 26, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 913789 • Toll Brothers Real Estate Inc., Thom...
Overlook
![4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 920677 • Toll Brothers Real Estate Inc., Thom...
The Villages at Mount Sinai Park
![109 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,736 sq ft
|Condo
109 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 887250 • Douglas Elliman Real Estate, Nancy D...
The Villages at Mount Sinai Park
![25 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|3 baths
|2,229 sq ft
|Condo
25 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 906234 • Douglas Elliman Real Estate, Nancy D...
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 Hills
![137 HERITAGE HLS # B B, SOMERS, NY, 1058..., Somers, NY 10589]()
1 beds
|1 baths
|955 sq ft
|Condo
137 HERITAGE HLS # B B, SOMERS, NY, 1058...
Community: Heritage Hills
MLS 924626 • Keller Williams NY Realty, Margaret ...
Glenwood Village
![1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,144 sq ft
|Mobile Home
1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 923306 • NGC Realty Group, Allison Diem
Heritage Hills
![247 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|1 baths
|955 sq ft
|Condo
247 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 900231 • eXp Realty, Mark Snyder
Glassbury Court at Cold Spring
![5 NORWEGIAN WOOD, COLD SPRING, NY, 10516, Cold Spring, NY 10516]()
2 beds
|2 baths
|1,974 sq ft
|Condo
5 NORWEGIAN WOOD, COLD SPRING, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 921030 • Houlihan Lawrence Inc., Abbie Carey
Glassbury Court at Cold Spring
![43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516]()
2 beds
|3 baths
|2,620 sq ft
|Condo
43 YESTERDAY DR, COLD SPRING, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 912195 • Coldwell Banker Realty, Audra Maccar...
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Questions? Call us:
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Heritage Hills
![798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,296 sq ft
|Condo
798 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 899317 • Houlihan Lawrence Inc., Donna O'Conn...
Jefferson Village
![34 WARWICK PL C, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,000 sq ft
|Condo
34 WARWICK PL C, YORKTOWN HEIGHTS, NY, 1...
Community: Jefferson Village
MLS 922352 • RE/MAX Classic Realty, George Campo...
Glassbury Court at Cold Spring
![11 REVOLUTION RD, COLD SPRING, NY, 10516, Cold Spring, NY 10516]()
2 beds
|3 baths
|1,806 sq ft
|Condo
11 REVOLUTION RD, COLD SPRING, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 902732 • Robert A. McCaffrey Realty Inc, Bill...
New
Jefferson Village
![148 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,159 sq ft
|Condo
148 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 927464 • My Seasons Realty LLC, Richard Dutra
Heritage Hills
![150 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,427 sq ft
|Condo
150 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 923969 • Houlihan Lawrence Inc., Cathy Weissm...
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 Hills
![627 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|1,098 sq ft
|Condo
627 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 915665 • William Raveis Real Estate, Geraldin...
Heritage Hills
![438 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,470 sq ft
|Condo
438 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 911228 • Keller Williams Realty Partner, Mark...
Sunken Pond Estates
![1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|3 baths
|1,350 sq ft
|Condo
1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
MLS 856851 • Signature Premier Properties, Ryan F...
Heritage Hills
![523 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,468 sq ft
|Condo
523 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 926725 • Giner Real Estate Inc., Peter Giner
Jefferson Village
![41 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
41 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 824285 • Houlihan Lawrence Inc., Barbara J. N...
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
Leisure Knoll
![304 KINGSTON CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 888419 • Northshore Properties Realty, Mary B...
Regency at Fishkill
![423 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,450 sq ft
|Condo
423 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 917650 • eXp Realty, Dvora E. Price
Leisure Village
![329 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,130 sq ft
|Condo
329 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
MLS 905779 • Realty Connect USA L I Inc, Sandi M....
Jefferson Village
![108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,200 sq ft
|Condo
108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
MLS 884476 • William Raveis Real Estate, Heather ...
Glenwood Village
![1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|2 baths
|924 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...
Community: Glenwood Village
MLS 927346 • Keystone Realty USA Corp, Cynthia Mc...
Frequently Asked Questions
In the Winchester Area, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in the Winchester Area has 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.
Yes, there is new 55+ home available in the Winchester Area. The most recent communities started in the Winchester Area include Oak Meadow Estates, Clockmaker's Hill. There is also 1 communities in the Winchester Area that offers new construction homes, including Oak Meadow Estates.
No, there are no gated 55+ communities in the Winchester Area.
On average, listings in 55+ communities in the Winchester Area stay on the market for around 788 days. The average price of homes for sale in these communities is approximately $389,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $389,900.
Want to learn more about 55+ communities in the Winchester Area?
- Insights and market stats
- Instant new home alerts
- Answers from local 55+ experts
Want to learn more about 55+ communities in Winchester Area?
92
communities
near Winchester Area
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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 29, 2025.
This application does not include information on all of the properties available for sale at this time.
