Call us at (959) 214-4386 to learn more about active adult communities in Middlebury
Middlebury, CT 55+ active adult communities & homes for sale - Page 3
137 communities near Middlebury
306 homes near Middlebury
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![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
No reviews yet
![Kensington Estates]()
$1Ms
- $1Ms
Kensington Estates, Woodbury, NY
New Construction
|
55+ age-restricted
|
Built 2019 - 2021
|
80 homes
No reviews yet
![Shaker Heights]()
$400Ks
- $500Ks
Shaker Heights, Enfield, CT
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
77 homes
Want to learn more about 55+ communities in Middlebury?
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Questions? Call us:
(959) 214-4386
No reviews yet
![Stone Ridge Estates]()
$500Ks
- $600Ks
Stone Ridge Estates, Dix Hills, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2013
|
76 homes
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
![The Polo Club at Islandia]()
$600Ks
- $600Ks
The Polo Club at Islandia, Islandia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
No reviews yet
![Breton Hills]()
$500Ks
Breton Hills, Glen Cove, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
No reviews yet
![Long Hill Village]()
$300Ks
- $400Ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 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
![Regency at Woodbridge]()
$500Ks
- $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
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
![Eagles Walk at East Quogu...]()
$500Ks
- $500Ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
67 homes
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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
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
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
![Autumn Fields]()
$200Ks
- $300Ks
Autumn Fields, Enfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2006
|
56 homes
No reviews yet
![The Village at Buckingham]()
$300Ks
- $400Ks
The Village at Buckingham, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
56 homes
No reviews yet
![The Views at Pomona]()
$200Ks
- $400Ks
The Views at Pomona, Pomona, NY
Resale Only
|
55+ age-restricted
|
Built 2011 - 2011
|
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
|
54 homes
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Questions? Call us:
(959) 214-4386
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
![Eastport Meadows]()
$400Ks
- $400Ks
Eastport Meadows, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2016
|
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
![Gloria Commons]()
$200Ks
- $300Ks
Gloria Commons, Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2015
|
50 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 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
No reviews yet
![Wolfe Landing]()
$500Ks
- $600Ks
Wolfe Landing, Clarkstown, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
43 homes
No reviews yet
![Village Vistas]()
$800Ks
- $1Ms
Village Vistas, Port Jefferson, NY
Resale Only
|
55+ age-restricted
|
Built 2013 - 2017
|
43 homes
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
No reviews yet
![Forest Mews]()
$300Ks
- $400Ks
Forest Mews, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
40 homes
No reviews yet
![Harbor View Estates]()
$400Ks
- $600Ks
Harbor View Estates, Copiague, NY
New Construction
|
55+ age-restricted
|
Built 2017 - 2018
|
40 homes
No reviews yet
![Hidden Harbor Estates]()
$500Ks
- $600Ks
Hidden Harbor Estates, Copiague, NY
Resale Only
|
55+ age-restricted
|
Built 2010 - 2015
|
38 homes
No reviews yet
![Clockmaker's Hill]()
$100Ks
- $100Ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
38 homes
No reviews yet
![Billingsgate]()
$400Ks
- $600Ks
Billingsgate, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
37 homes
Jefferson Village
![40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,350 sq ft
|Condo
40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 850226 • Coldwell Banker Realty, Mary Anne M....
Meadowbrook Pointe Links & Spa
![65 PACIFIC DUNES CT, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|2,006 sq ft
|Condo
65 PACIFIC DUNES CT, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 861507 • Signature Premier Properties, Matthe...
HarborView
![100 HARBOR VIEW DR 249, PORT WASHINGTON,..., Port Washington, NY 11050]()
2 beds
|3 baths
|1,493 sq ft
|Condo
100 HARBOR VIEW DR 249, PORT WASHINGTON,...
Community: HarborView
MLS 840770 • Douglas Elliman Real Estate, Melanie...
Heritage Hills
![234 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,427 sq ft
|Condo
234 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 828326 • Keller Williams Rlty Landmark, Maria...
Woodridge Strathmore Terrace
![16 HEARTHSIDE DR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
1 beds
|1 baths
|924 sq ft
|Condo
16 HEARTHSIDE DR, MOUNT SINAI, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 850667 • Mazzella Realty Services, Michael A....
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
Greenwood Village
![77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|1 baths
|1,000 sq ft
|Condo
77 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 853523 • Gateway to The Hamptons R E, Janet R...
Greenwood Village
![22 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|920 sq ft
|Condo
22 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 841313 • Gateway to The Hamptons R E, Vivian ...
Dutchgate
![812 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580]()
MLS 862193 • Winzone Realty Inc, Ka Yeung MRP SFR
Heritage Hills
![196A HERITAGE HLS # 196A, SOMERS, NY, 10..., Somers, NY 10589]()
2 beds
|2 baths
|1,427 sq ft
|Condo
196A HERITAGE HLS # 196A, SOMERS, NY, 10...
Community: Heritage Hills
MLS 840157 • Julia B Fee Sothebys Int. Rlty, Zebe...
Country Pointe Plainview
![34203 WINTERBERRY DR, PLAINVIEW, NY, 118..., Plainview, NY 11803]()
2 beds
|2 baths
|1,335 sq ft
|Condo
34203 WINTERBERRY DR, PLAINVIEW, NY, 118...
Community: Country Pointe Plainview
MLS 861969 • Signature Premier Properties, Janice...
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.
Leisure Village
![419 WEYMOUTH CT F, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 812541 • Howard Hanna Coach, Linda Stowell
Sunrise Village
![133 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782]()
2 beds
|1 baths
|1,000 sq ft
|Condo
133 REVERE DR, SAYVILLE, NY, 11782
Community: Sunrise Village
MLS 862832 • Triple Crown Real Estate Assoc, Jaso...
Sunrise Village
![14 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782]()
MLS 860801 • Douglas Elliman Real Estate, Lisa F....
Jefferson Village
![92 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598]()
1 beds
|1 baths
|800 sq ft
|Condo
92 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,...
Community: Jefferson Village
MLS 855989 • Compass Greater NY, LLC, Daniel McKe...
Jessup's Landing
![25 JESSUPS LANDING CT UNIT E, QUOGUE, NY..., Quogue, NY 11959]()
5 beds
|5 baths
|2,807 sq ft
|Condo
25 JESSUPS LANDING CT UNIT E, QUOGUE, NY...
Community: Jessup's Landing
MLS 860480 • Douglas Elliman Real Estate, Enzo Mo...
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
Leisure Village
![332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ..., Ridge, NY 11961]()
2 beds
|1 baths
|1,000 sq ft
|Condo
332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ...
Community: Leisure Village
MLS 861217 • Howard Hanna Coach, Linda Stowell
Greenwood Village
![87 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|1 baths
|992 sq ft
|Condo
87 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 859704 • Douglas Elliman Real Estate, Juliana...
Leisure Village
![277 BERWICK CT UNIT D, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
277 BERWICK CT UNIT D, RIDGE, NY, 11961
Community: Leisure Village
MLS 858082 • Island Advantage Realty LLC, Jennife...
Leisure Village
![258 NEWCASTLE CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
258 NEWCASTLE CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 856345 • Coldwell Banker American Homes, Nord...
Foxwood Village
![1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119..., Riverhead, NY 11933]()
2 beds
|2 baths
|1,280 sq ft
|House
1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119...
Community: Foxwood Village
MLS 855435 • Signature Premier Properties, Jason ...
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.
Encore Atlantic Shores
![68 ENCORE, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941]()
2 beds
|3 baths
|3,000 sq ft
|Condo
68 ENCORE, BROOKHAVEN, NY, 11941
Community: Encore Atlantic Shores
MLS 851829 • Realty Connect USA LI Inc, Deanna Em...
Leisure Village
![156 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
156 FALMOUTH CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 848587 • Baez Real Estate, Inc., Alex V. Baez
The Seasons at East Meadow
![315 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554]()
2 beds
|2 baths
|1,272 sq ft
|Condo
315 SPRING DR, EAST MEADOW, NY, 11554
Community: The Seasons at East Meadow
MLS 848654 • Caruso & Boughton Realty Inc, Peter ...
HarborView
![100 HARBOR VIEW DR 230, PORT WASHINGTON,..., Port Washington, NY 11050]()
3 beds
|3 baths
|2,395 sq ft
|Condo
100 HARBOR VIEW DR 230, PORT WASHINGTON,...
Community: HarborView
MLS 843935 • Keller Williams Points North, Barry ...
Heritage Hills
![239 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,689 sq ft
|Condo
239 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 815679 • Coldwell Banker Realty, Debra DeMeli...
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
The Waterways at Moriches
![107 E MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955]()
2 beds
|2 baths
|2,141 sq ft
|Condo
107 E MIDLAND POND CT, MORICHES, NY, 119...
Community: The Waterways at Moriches
MLS 829455 • Douglas Elliman Real Estate, Jo Ann ...
The Polo Club at Islandia
![1239 OLD NICHOLS RD # 51, ISLANDIA, NY, ..., Islandia, NY 11749]()
2 beds
|3 baths
|1,654 sq ft
|Condo
1239 OLD NICHOLS RD # 51, ISLANDIA, NY, ...
Community: The Polo Club at Islandia
MLS L3591817 • Daniel Gale Sothebys Intl Rlty, Fe...
Leisure Village
![425 BRIDGEWATER DR UNIT A A, RIDGE, NY, ..., Ridge, NY 11961]()
2 beds
|2 baths
|966 sq ft
|Condo
425 BRIDGEWATER DR UNIT A A, RIDGE, NY, ...
Community: Leisure Village
MLS 840625 • Leisure Living Realty Inc, Laura Ruh...
Glenwood Village
![1661-563 OLD COUNTRY RD 563, RIVERHEAD, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,500 sq ft
|Manufactured Home
1661-563 OLD COUNTRY RD 563, RIVERHEAD, ...
Community: Glenwood Village
MLS 839070 • Keystone Realty USA Corp, Cynthia Mc...
Country Pointe Plainview
![18205 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803]()
2 beds
|2 baths
|1,474 sq ft
|Condo
18205 ASPENWOOD DR, PLAINVIEW, NY, 11803
Community: Country Pointe Plainview
MLS 842891 • Thomas S. Hennerty, Thomas S. Henner...
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.
Leisure Village
![135 EASTBOURNE CT UNIT C, RIDGE, NY, 119..., Ridge, NY 11961]()
2 beds
|1 baths
|1,118 sq ft
|Condo
135 EASTBOURNE CT UNIT C, RIDGE, NY, 119...
Community: Leisure Village
MLS 854336 • Coldwell Banker American Homes, Joy ...
Leisure Knoll
![460 SUMMERWOOD CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 841946 • Realty Connect USA L I Inc, Michele ...
Leisure Village
![269 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,048 sq ft
|Condo
269 BERWICK CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 856130 • Oversouth LLC, Deniz Ozgur
The Polo Club at Islandia
![1239 OLD NICHOLS RD # 46, ISLANDIA, NY, ..., Islandia, NY 11749]()
2 beds
|3 baths
|1,654 sq ft
|Condo
1239 OLD NICHOLS RD # 46, ISLANDIA, NY, ...
Community: The Polo Club at Islandia
MLS 855948 • Daniel Gale Sothebys Intl Rlty, Dani...
Jefferson Village
![156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
1 beds
|1 baths
|850 sq ft
|Condo
156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 823393 • Houlihan Lawrence Inc., Nancy Kenned...
Want to learn more about 55+ communities in Middlebury?
55places can help!
Questions? Call us:
(959) 214-4386
Meadowbrook Pointe Athletic Club & Spa
![450 PACING WAY, WESTBURY, NY, 11590, Westbury, NY 11590]()
2 beds
|2 baths
|1,328 sq ft
|Condo
450 PACING WAY, WESTBURY, NY, 11590
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 849917 • Realty Connect USA LLC, Nancy J. Pel...
Leisure Knoll
![176 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 840567 • Coldwell Banker American Homes, Donn...
Glenwood Village
![1661-308 OLD COUNTRY RD 308, RIVERHEAD, ..., Riverhead, NY 11901]()
2 beds
|1 baths
|840 sq ft
|Mobile Home
1661-308 OLD COUNTRY RD 308, RIVERHEAD, ...
Community: Glenwood Village
MLS L3583691 • Realty Connect USA L I Inc, Fengxi...
Leisure Glen
![460 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 830412 • RE/MAX Integrity Leaders, Karen L. R...
Leisure Village
![373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,171 sq ft
|Condo
373 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
MLS 845085 • Center 24 Realty Corp, Heidi S. Will...
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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