Call us at (860) 909-8066 to learn more about active adult communities near Winsted
Winsted, CT 55+ active adult communities & homes for sale - Page 2
76 communities near Winsted
166 homes near Winsted
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![Regency at Woodbridge]()
$500Ks
- $500Ks
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
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55+ age-restricted
|
Built 2003 - 2006
|
69 homes
No reviews yet
![Sonoma Woods]()
$300Ks
- $300Ks
Sonoma Woods, Middletown, CT
Resale Only
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55+ age-restricted
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Built 2005 - 2015
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68 homes
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
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No reviews yet
![Glassbury Court at Hunter...]()
$500Ks
- $700Ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only
|
55+ age-restricted
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Built 2007 - 2014
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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
No reviews yet
![Woodcrest at Jacobs Hill]()
$300Ks
- $300Ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only
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55+ age-restricted
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Built 2005 - 2006
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58 homes
No reviews yet
![Autumn Fields]()
$200Ks
- $300Ks
Autumn Fields, Enfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2006
|
56 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 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
![77 Sunset Lane]()
$400Ks
- $700Ks
77 Sunset Lane, Ridgefield, CT
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
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54 homes
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
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Questions? Call us:
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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
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
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
![Forest Mews]()
$300Ks
- $400Ks
Forest Mews, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
40 homes
No reviews yet
![Billingsgate]()
$400Ks
- $600Ks
Billingsgate, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
37 homes
No reviews yet
![Bidwell Village]()
$300Ks
- $400Ks
Bidwell Village, Coventry, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
37 homes
No reviews yet
![Boulder Brook]()
$200Ks
- $200Ks
Boulder Brook, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2006
|
35 homes
No reviews yet
![Eden Park]()
$500Ks
- $600Ks
Eden Park, Clarkstown, NY
Resale Only
|
55+ age-restricted
|
Built 2011 - 2011
|
34 homes
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
(860) 909-8066
No reviews yet
![The Woods at Dunham Pond]()
$400Ks
- $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2015
|
33 homes
No reviews yet
![Oak Meadow Estates]()
$200Ks
- $400Ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
No reviews yet
![Autumn Estates]()
$500Ks
- $600Ks
Autumn Estates, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2011 - 2017
|
30 homes
No reviews yet
![The Coach Homes at Ridgef...]()
$200Ks
- $500Ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
30 homes
No reviews yet
![Bartlett Hollow]()
$200Ks
- $400Ks
Bartlett Hollow, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2015 - 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.
No reviews yet
![RiverBend Estates]()
$400Ks
- $400Ks
RiverBend Estates, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2012 - present
|
25 homes
No reviews yet
![Granite Woods]()
$600Ks
- $700Ks
Granite Woods, Middlebury, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
24 homes
No reviews yet
![Summer Wind Estates]()
$300Ks
- $400Ks
Summer Wind Estates, North Haven, CT
New Construction
|
55+ age-restricted
|
Built 2015 - present
|
18 homes
No reviews yet
![Park Glen]()
$500Ks
- $600Ks
Park Glen, New Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2015
|
17 homes
No reviews yet
![Newington Ridge Preserve]()
$300Ks
- $400Ks
Newington Ridge Preserve, Newington, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
16 homes
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
No reviews yet
![Cobblestone Court]()
$400Ks
- $500Ks
Cobblestone Court, Essex, CT
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
8 homes
The Gardens of Wilbraham
![116 CHERRY DR # 116, WILBRAHAM, MA, 0109..., Wilbraham, MA 01095]()
2 beds
|2 baths
|1,634 sq ft
|Condo
116 CHERRY DR # 116, WILBRAHAM, MA, 0109...
Community: The Gardens of Wilbraham
MLS 73441478 • Coldwell Banker Realty - Western M...
Heritage Hills
![247 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|1 baths
|967 sq ft
|Condo
247 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 900231 • eXp Realty, Mark Snyder
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...
New
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...
Heritage Hills
![971 HERITAGE HLS E, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,559 sq ft
|Condo
971 HERITAGE HLS E, SOMERS, NY, 10589
Community: Heritage Hills
MLS 912609 • RE/MAX Prestige Properties, Maria O'...
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
Overlook
![1019 COTTAGE DR # 9, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 923664 • Toll Brothers Real Estate Inc., Thom...
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 ...
New
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
New
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
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
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.
Overlook
![1042 COTTAGE DR # 25, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 911920 • Toll Brothers Real Estate Inc., Thom...
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...
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 ...
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...
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
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
(860) 909-8066
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
Founders Village
![2555 YOUNGS AVE 17D, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|Condo
2555 YOUNGS AVE 17D, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 927213 • Douglas Elliman Real Estate, Barbara...
New
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...
New
Harvest Pointe
![32 MILLSTONE LN 16, CUTCHOGUE, NY, 11935, Cutchogue, NY 11935]()
2 beds
|3 baths
|1,600 sq ft
|Condo
32 MILLSTONE LN 16, CUTCHOGUE, NY, 11935
Community: Harvest Pointe
MLS 921257 • Douglas Elliman Real Estate, Melissa...
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...
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.
Jefferson Village
![84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...
Community: Jefferson Village
MLS 877595 • Coldwell Banker Realty, Maureen Conn...
Regency at Fishkill
![736 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,543 sq ft
|Condo
736 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 915698 • Joncar Realty Inc, Margaret R Rose
Overlook
![1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 889837 • 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...
Overlook
![1040 COTTAGE DR # 26, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 913789 • Toll Brothers Real Estate Inc., Thom...
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
Overlook
![4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 920677 • 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...
Jefferson Village
![159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,300 sq ft
|House
159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 914751 • Glilos, Yoel Schwartz
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
![711 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|1,098 sq ft
|Condo
711 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 923997 • Houlihan Lawrence Inc., Donna O'Conn...
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
![468 HERITAGE HLS E, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,265 sq ft
|Condo
468 HERITAGE HLS E, SOMERS, NY, 10589
Community: Heritage Hills
MLS 913543 • Coldwell Banker Realty, Lois Hanley
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...
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...
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
![45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 916000 • Compass Greater NY, LLC, Anna Priski...
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
Jefferson Village
![129C COLUMBIA CT, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
129C COLUMBIA CT, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
MLS 910437 • Exit Realty Connections, Susan T Ale...
Regency at Fishkill
![326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,543 sq ft
|Condo
326 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 890462 • RE/MAX Town & Country, Spyros Spyrou
Heritage Hills
![788 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,296 sq ft
|Condo
788 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 916529 • William Raveis-New York LLC, Hope Ro...
Heritage Hills
![489 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,483 sq ft
|Condo
489 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 915507 • Keller Williams Realty Partner, Pame...
Jefferson Village
![15 ESSEX PL 15K, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|1 baths
|1,000 sq ft
|Condo
15 ESSEX PL 15K, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 903883 • Keller Williams Realty Group, Erin E...
Frequently Asked Questions
In Winsted, there is 1 small community with less than 500 homes.
The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.
No, there are no gated 55+ communities in Winsted.
Want more information about active adult communities around Winsted?
Want to learn more about 55+ communities in Winsted?
76
communities
near Winsted
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REIN updates its listings on a daily basis. Data last updated: Oct 25, 2025.
This application does not include information on all of the properties available for sale at this time.
