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
287 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
- $600Ks
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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(959) 214-4386
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
- $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$500Ks
- $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]()
$800Ks
- $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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(959) 214-4386
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
- $300Ks
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
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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Questions? Call us:
(959) 214-4386
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
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
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]()
$600Ks
- $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
Meadowbrook Pointe Links & Spa
![42 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|1,534 sq ft
|Condo
42 AUGUSTA DR, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 841734 • Signature Premier Properties, Matthe...
Westhampton Pines
![42 KIMBERLY DR # 42, WESTHAMPTON, NY, 11..., Westhampton, NY 11977]()
2 beds
|3 baths
|2,350 sq ft
|Condo
42 KIMBERLY DR # 42, WESTHAMPTON, NY, 11...
Community: Westhampton Pines
MLS 860124 • Kerrigan Country Realty, Elaine S. B...
Encore at Lake Grove
![10 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755]()
2 beds
|2 baths
|1,390 sq ft
|Condo
10 SYMPHONY DR, LAKE GROVE, NY, 11755
Community: Encore at Lake Grove
MLS 853018 • RE/MAX Integrity Leaders, Robert J....
Encore Atlantic Shores
![82 BALLAD CT, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|3 baths
|2,150 sq ft
|Condo
82 BALLAD CT, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 855947 • Gateway to The Hamptons R E, Vivian ...
Westhampton Pines
![69 SAMANTHA CIR # 69, WESTHAMPTON, NY, 1..., Westhampton, NY 11977]()
2 beds
|2 baths
|1,944 sq ft
|Condo
69 SAMANTHA CIR # 69, WESTHAMPTON, NY, 1...
Community: Westhampton Pines
MLS 854491 • Kerrigan Country Realty, Bruce C. Ph...
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
Heritage Hills
![480 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,468 sq ft
|Condo
480 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 837074 • William Raveis-New York, LLC, Gerald...
The Greens at Half Hollow
![1069 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|2 baths
|1,140 sq ft
|Condo
1069 SAVOY DR, MELVILLE, NY, 11747
Community: The Greens at Half Hollow
MLS 844110 • Douglas Elliman Real Estate, Cynthia...
Founders Village
![2555 YOUNGS AVE 7D, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|Condo
2555 YOUNGS AVE 7D, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 808158 • Signature Premier Properties, Timoth...
New
The Waterways at Moriches
![497 OAK BLUFF CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|3 baths
|1,988 sq ft
|Condo
497 OAK BLUFF CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 873131 • Signature Premier Properties, Dorrie...
New
Greenwood Village
![5148 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,350 sq ft
|Condo
5148 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 874689 • Gateway to The Hamptons R E, Vivian ...
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.
Dutchgate
![1011 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580]()
MLS 864009 • North Star Homes Inc, Nimisha Baball
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...
Meadowbrooke Pointe East Meadow
![417 EMANUEL WAY # 417, EAST MEADOW, NY, ..., East Meadow, NY 11554]()
2 beds
|2 baths
|961 sq ft
|Condo
417 EMANUEL WAY # 417, EAST MEADOW, NY, ...
Community: Meadowbrooke Pointe East Meadow
MLS 841635 • Cosmo Group Realty, Jessica Alejo
Stone Ridge Estates
![156 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746]()
2 beds
|2 baths
|1,700 sq ft
|Condo
156 CHRISTINE DR, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
MLS 859377 • Howard Hanna Coach, Susan Catik
Glenwood Village
![1661 OLD COUNTRY RD UNIT 521, RIVERHEAD,..., Riverhead, NY 11901]()
MLS L3593702 • Moriches Bay Realty, Geraldine S. ...
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
Glenwood Village
![1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,270 sq ft
|Mobile Home
1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 827152 • Douglas Elliman Real Estate, Allison...
Jefferson Village
![60 KIRBY CLOSE F, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|910 sq ft
|Condo
60 KIRBY CLOSE F, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
MLS 866227 • HomeSmart Homes & Estates, Christoph...
New
Leisure Village
![231 BLACKPOOL CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 874532 • Daniel Gale Sothebys Intl Rlty, Nico...
Leisure Knoll
![209 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 861828 • Coldwell Banker American Homes, Kath...
Greenwood Village
![24 LIMETREE DR # 24, MANORVILLE, NY, 119..., Manorville, NY 11949]()
2 beds
|2 baths
|1,100 sq ft
|Condo
24 LIMETREE DR # 24, MANORVILLE, NY, 119...
Community: Greenwood Village
MLS L3554128 • Signature Premier Properties, Meli...
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.
Greenwood Village
![21 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,100 sq ft
|Condo
21 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 866101 • Signature Premier Properties, Meliss...
Leisure Village
![232 BLACKPOOL CT F, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|833 sq ft
|Condo
232 BLACKPOOL CT F, RIDGE, NY, 11961
Community: Leisure Village
MLS 873804 • Realty Connect USA LI, Margaret Tsou...
The Bel Aire at East Meadow
![50 MERRICK AVE 313, EAST MEADOW, NY, 115..., East Meadow, NY 11554]()
2 beds
|2 baths
|1,000 sq ft
|Condo
50 MERRICK AVE 313, EAST MEADOW, NY, 115...
Community: The Bel Aire at East Meadow
MLS 865749 • BERKSHIRE HATHAWAY, Michael J. Fink ...
Vineyards at Blue Point
![125 HALLEY DR, BLUE POINT, NY, 11772, Blue Point, NY 11772]()
2 beds
|2 baths
|1,619 sq ft
|Condo
125 HALLEY DR, BLUE POINT, NY, 11772
Community: Vineyards at Blue Point
MLS 845282 • Signature Premier Properties, Renee ...
Leisure Village
![28 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 869368 • Signature Premier Properties, Jose A...
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
Jefferson Village
![143 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,200 sq ft
|Condo
143 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 867675 • RE/MAX Town & Country, James D'Amato
Knickerbocker Bay Club
![433 MAIN ST 203, PORT WASHINGTON, NY, 11..., Port Washington, NY 11050]()
2 beds
|2 baths
|1,323 sq ft
|Condo
433 MAIN ST 203, PORT WASHINGTON, NY, 11...
Community: Knickerbocker Bay Club
MLS 865024 • Douglas Elliman Real Estate, Kristin...
Leisure Village
![374 WOODBRIDGE DR UNIT A A, RIDGE, NY, 1..., Ridge, NY 11961]()
2 beds
|1 baths
|1,187 sq ft
|Condo
374 WOODBRIDGE DR UNIT A A, RIDGE, NY, 1...
Community: Leisure Village
MLS 872874 • Coldwell Banker American Homes, Joy ...
Leisure Village
![119 EXMORE CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 872112 • Leisure Living Realty Inc, Paulina R...
Strathmore Gate East
![9 FORGE LN, CORAM, NY, 11727, Coram, NY 11727]()
MLS 871943 • New Door Properties LLC, Gerald Wood
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.
Fairfield at St. James
![1204 GOTHAM DR # 1204, SAINT JAMES, NY, ..., Saint James, NY 11780]()
1 beds
|2 baths
|750 sq ft
|Condo
1204 GOTHAM DR # 1204, SAINT JAMES, NY, ...
Community: Fairfield at St. James
MLS 871909 • Signature Premier Properties, Rowena...
The Waterways at Moriches
![276 DOCKSIDE CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|1,875 sq ft
|Condo
276 DOCKSIDE CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 866339 • Douglas Elliman Real Estate, Jo Ann ...
Heritage Hills
![304 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|3 baths
|1,700 sq ft
|Condo
304 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 866789 • Coldwell Banker Realty, Kelly Castig...
Foxwood Village
![1407 MIDDLE RD 203, CALVERTON, NY, 11933, Calverton, NY 11933]()
3 beds
|2 baths
|1,568 sq ft
|Manufactured Home
1407 MIDDLE RD 203, CALVERTON, NY, 11933
Community: Foxwood Village
MLS 866087 • Joanne Kane Gigantiello, Joanne Giga...
Country Village Estates
![192 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727]()
2 beds
|2 baths
|1,308 sq ft
|Condo
192 THEODORE DR, CORAM, NY, 11727
Community: Country Village Estates
MLS 865313 • Realty Connect USA L I Inc, Bonnie S...
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
Heritage Hills
![116 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,144 sq ft
|Condo
116 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 863774 • Houlihan Lawrence Inc., David J. Hov...
Leisure Knoll
![140A LAURANCE LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 857230 • Coldwell Banker American Homes, Mary...
Meadowbrook Pointe Athletic Club & Spa
![100 SHADY LN # 100, WESTBURY, NY, 11590, Westbury, NY 11590]()
2 beds
|2 baths
|1,353 sq ft
|Condo
100 SHADY LN # 100, WESTBURY, NY, 11590
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 866039 • Daniel Gale Sothebys Intl Rlty, Dawn...
Plymouth Estates at Mount Sinai
![211 POND CIR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,662 sq ft
|Condo
211 POND CIR, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 862739 • Yes Homes Realty Ltd, Philip W. Alba
Leisure Village
![312C WOODBRIDGE DR 312C, BROOKHAVEN, NY,..., Brookhaven, NY 11961]()
1 beds
|1 baths
|679 sq ft
|Condo
312C WOODBRIDGE DR 312C, BROOKHAVEN, NY,...
Community: Leisure Village
MLS 842478 • Leisure Living Realty Inc, Laura Ruh...
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?
287
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