Call us at (959) 214-4386 to learn more about active adult communities in Middlebury
Middlebury, CT 55+ active adult communities & homes for sale
137 communities near Middlebury
304 homes near Middlebury
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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
![Granite Woods]()
$600Ks
- $700Ks
Granite Woods, Middlebury, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
24 homes
3 rating (2 reviews)
![Heritage Hills]()
$400Ks
- $700Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1975 - 2003
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $400Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
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No reviews yet
![The Greens at Half Hollow]()
$600Ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
No reviews yet
![Rivington]()
$400Ks
- $1Ms
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$300Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$400Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $600Ks
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.
No reviews yet
![Meadowbrook Pointe Athlet...]()
$800Ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 homes
No reviews yet
![Leisure Knoll]()
$300Ks
- $500Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
No reviews yet
![Country Pointe Plainview]()
$900Ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
5 rating (1 reviews)
![Fairfield at St. James]()
$400Ks
- $500Ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
No reviews yet
![Leisure Glen]()
$400Ks
- $500Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
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No reviews yet
![Spring Lake Village]()
$200Ks
- $200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
3.7 rating (3 reviews)
![Greenwood Village]()
<$100k
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
No reviews yet
![The Seasons at East Meado...]()
$500Ks
- $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 homes
No reviews yet
![Regency at Prospect]()
$400Ks
- $400Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 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
![Dutchgate]()
$400Ks
- $400Ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 homes
No reviews yet
![The Waterways at Moriches]()
$400Ks
- $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
No reviews yet
![The Retreat at Carmel]()
$300Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
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(959) 214-4386
4.6 rating (9 reviews)
![Meadowbrook Pointe Links ...]()
$600Ks
- $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]()
$600Ks
- $900Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
No reviews yet
![HarborView]()
$900Ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 homes
No reviews yet
![The Club at Melville]()
$500Ks
- $500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
No reviews yet
![The Seasons at Elwood]()
$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.
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $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
No reviews yet
![The Summit at Bethel]()
$700Ks
- $800Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $500Ks
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
Want to learn more about 55+ communities in Middlebury?
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Questions? Call us:
(959) 214-4386
No reviews yet
![Woodridge Strathmore Terr...]()
$300Ks
- $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
No reviews yet
![Regency at Wappinger]()
$700Ks
- $800Ks
Regency at Wappinger, Wappingers Falls, NY
New and Resale
|
55+ age-restricted
|
Built 2014 - present
|
225 homes
5 rating (1 reviews)
![Sunrise Village]()
$400Ks
- $500Ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 homes
No reviews yet
![Saddle Lakes]()
$400Ks
- $400Ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
No reviews yet
![Country Village Estates]()
$400Ks
- $400Ks
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
|
195 homes
Bartlett Hollow
![39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0..., Middletown, CT 06457]()
2 beds
|3 baths
|3,147 sq ft
|Condo
39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0...
Community: Bartlett Hollow
MLS 24100370 • William Raveis Real Estate, Siobha...
New
Heritage Village
![926 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
926 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24100579 • Joseph Bette REALTORS Inc, Cynthia...
Heritage Village
![894 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
894 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24085128 • Joseph Bette REALTORS Inc, Justin ...
New
Oronoque Village
![156 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,175 sq ft
|Condo
156 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24100780 • William Raveis Real Estate, Joseph...
Heritage Village
![79 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
79 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24091089 • Keller Williams Realty, Gabby Addi...
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Questions? Call us:
(959) 214-4386
Heritage Village
![128 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
128 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24086942 • Berkshire Hathaway NE Prop., Joan ...
Heritage Village
![687 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
687 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24099123 • Berkshire Hathaway NE Prop., Miche...
Heritage Village
![740 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
740 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24092035 • Coldwell Banker Realty, Maryanne B...
Spring Lake Village
![477 CARRIAGE DR # 477, SOUTHINGTON, CT, ..., Southington, CT 06489]()
2 beds
|2 baths
|1,188 sq ft
|Condo
477 CARRIAGE DR # 477, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24100110 • Century 21 AllPoints Realty, Betty...
Heritage Village
![78 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
78 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24098464 • Coldwell Banker Realty, Maryanne B...
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
Chatfield Farms
![3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ..., Beacon Falls, CT 06403]()
3 beds
|4 baths
|2,052 sq ft
3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ...
Community: Chatfield Farms
MLS 24101359 • Dow Della Valle, E. Tyler Della Va...
Heritage Village
![957A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
957A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24071514 • William Raveis Real Estate, Pat Ca...
New
Heritage Village
![98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24101279 • Berkshire Hathaway NE Prop., Miche...
Gloria Commons
![3 ALANA DR # 3, MILFORD, CT, 06461, Milford, CT 06461]()
MLS 24093568 • William Raveis Real Estate, Collee...
Heritage Village
![1042 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,071 sq ft
|Condo
1042 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24080741 • Berkshire Hathaway NE Prop., Miche...
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Heritage Village
![917 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
917 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24084124 • Berkshire Hathaway NE Prop., Scott...
Heritage Village
![787 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
787 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24096092 • Berkshire Hathaway NE Prop., Miche...
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 24092610 • William Raveis Real Estate, Joan K...
Heritage Village
![134 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
134 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24100995 • Berkshire Hathaway NE Prop., Miche...
Heritage Village
![151 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
151 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24097060 • Showcase Realty, Inc., Stephanie V...
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.
Liberty at Newtown
![5 FRANKLIN CT # 5, NEWTOWN, CT, 06470, Newtown, CT 06470]()
2 beds
|3 baths
|2,407 sq ft
|Condo
5 FRANKLIN CT # 5, NEWTOWN, CT, 06470
Community: Liberty at Newtown
MLS 24097058 • Blackstone Properties of CT, Annma...
Oronoque Village
![635 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,642 sq ft
|Condo
635 NORTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24095005 • Oronoque Real Estate, Monica Dalto...
The Village at Oxford Greens
![644 CHAMPIONSHIP DR # 644, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|3 baths
|2,296 sq ft
|Condo
644 CHAMPIONSHIP DR # 644, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24096492 • Coldwell Banker Realty, Joseph Pau...
Rivington
![802 CENTER MEADOW LN # 802, DANBURY, CT,..., Danbury, CT 06810]()
MLS 24098944 • Berkshire Hathaway NE Prop., Bonni...
Heritage Village
![644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
644 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24088213 • Berkshire Hathaway NE Prop., Kathy...
Want to learn more about 55+ communities in Middlebury?
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Questions? Call us:
(959) 214-4386
Oronoque Village
![588 ARAPAHO LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,438 sq ft
|Condo
588 ARAPAHO LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24091630 • Sarah Harrower Realty, Barbara Dun...
The Powder Forest Homes
![3 PROSPECT RDG, SIMSBURY, CT, 06070, Simsbury, CT 06070]()
4 beds
|4 baths
|2,557 sq ft
3 PROSPECT RDG, SIMSBURY, CT, 06070
Community: The Powder Forest Homes
MLS 24098219 • Berkshire Hathaway NE Prop., Ellen...
Heritage Village
![57 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
57 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24098902 • Berkshire Hathaway NE Prop., Bonni...
O'Meara Farm
![8 MULBERRY LN # 8, FARMINGTON, CT, 06032, Farmington, CT 06032]()
MLS 24098894 • Berkshire Hathaway NE Prop., Lyle ...
Rivington
![19 MILL RD # 19, DANBURY, CT, 06810, Danbury, CT 06810]()
MLS 24088160 • RE/MAX One, Shannon Muscara
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.
Rivington
![38 WINDING RIDGE WAY, DANBURY, CT, 06810, Danbury, CT 06810]()
3 beds
|3 baths
|1,767 sq ft
|Condo
38 WINDING RIDGE WAY, DANBURY, CT, 06810
Community: Rivington
MLS 24081996 • Houlihan Lawrence, Barbara Sawin
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 24091449 • Around Town Real Estate LLC, Andre...
Regency at Woodbridge
![7 HERITAGE LN # 67, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,486 sq ft
|Condo
7 HERITAGE LN # 67, WOODBRIDGE, CT, 0652...
Community: Regency at Woodbridge
MLS 24079730 • Thomas Jacovino, Kathy Childs
Regency at Woodbridge
![5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,006 sq ft
|Condo
5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652...
Community: Regency at Woodbridge
MLS 24097354 • Thomas Jacovino, Kathy Childs
Heritage Village
![1000 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
1000 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24091531 • Around Town Real Estate LLC, James...
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
The Summit at Bethel
![63 GREAT HILL DR # 63, BETHEL, CT, 06801, Bethel, CT 06801]()
3 beds
|3 baths
|2,743 sq ft
|Condo
63 GREAT HILL DR # 63, BETHEL, CT, 06801
Community: The Summit at Bethel
MLS 24086666 • Around Town Real Estate LLC, Danie...
Billingsgate
![2 PENNINGTON DR # 2, SIMSBURY, CT, 06070, Simsbury, CT 06070]()
2 beds
|3 baths
|2,867 sq ft
|Condo
2 PENNINGTON DR # 2, SIMSBURY, CT, 06070
Community: Billingsgate
MLS 24085860 • William Pitt Sotheby's Int'l, Dian...
Benson Woods
![112 PERIWINKLE DR # 112, MIDDLEBURY, CT,..., Middlebury, CT 06762]()
2 beds
|3 baths
|2,593 sq ft
|Condo
112 PERIWINKLE DR # 112, MIDDLEBURY, CT,...
Community: Benson Woods
MLS 24085335 • BHGRE Bannon & Hebert, Mary Ann He...
Heritage Village
![122 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
122 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24092348 • Berkshire Hathaway NE Prop., Miche...
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 24098094 • William Raveis Real Estate, Daniel...
Frequently Asked Questions
In Middlebury, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in Middlebury has 24 homes, the largest has 79 homes, and the average communities consists of 51 homes.
Yes, there are new 55+ homes available in Middlebury. The most recent communities started in Middlebury include Granite Woods, Benson Woods. There are also 2 communities in Middlebury that offer new construction homes, including Benson Woods, Granite Woods.
No, there are no gated 55+ communities in Middlebury.
On average, listings in 55+ communities in Middlebury stay on the market for around 11 days. The average price of homes for sale in these communities is approximately $569,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Benson Woods average around $569,900.
Want more information about active adult communities around Middlebury?
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