Middlebury, CT Homes

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  $717,000

  • 3 Beds
  • 2.5 Baths
  • 3,212 Sq Ft

  111 Dwyer Rd, Middlebury, CT 06762

  Elegant Saltbox Colonial in Sought-After Middlebury, Nestled on 2.44 secluded acres, this tasteful saltbox colonial boasts park-like grounds with a private, tree-lined driveway leading to professionally landscaped gardens. Enjoy blooming trees and bushes from spring to fall, creating a picturesque setting. Outdoor living is enhanced with a slate patio, built-in barbecue, and bocce court, perfect

  

  Mary Ann Hebert

  BHGRE Gaetano Marra Homes

  (203) 693-8485

  111 Dwyer Rd, Middlebury, CT 06762
• Explore Middlebury

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  /21

  $2,600 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,266 Sq Ft
  • House for Rent

  253 Porter Ave, Middlebury, CT 06762

  Fabulous rental featuring a bright, open floor plan with hardwood floors throughout. The updated kitchen boasts stainless steel appliances, granite countertops and a huge island-perfect for meal prep and casual dining. First-floor convenience includes laundry and half bath. Upstairs, three generous bedrooms and a beautifully renovated full bath await. Entertain with ease on the newly built Trex

  Maria Formanek William Pitt Sotheby's Int'l

  253 Porter Ave, Middlebury, CT 06762
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  $409,000 Sold Nov 25, 2025

  • 1,498 Sq Ft
  • $273/SF
  • 39 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  115 Porter Ave, Middlebury, CT 06762

  PRICED RIGHT FOR IMMEDIATE SALE! SNOOZE YOU LOSE! THIS IS "NATURES LOVERS DREAM HOME", PERFECT FOR BIRD WATCHERS, ON OPEN & GLORIOUS 1.80 ACRES WITH MATURE FRUIT/NUTS/BERRIES/BUSHES & WILLOW TREES, TO NAME A FEW! ALMOST 1500 S.F. OF LIVING! A BEAUTIFUL BABBLING BROOK. FOR PEACE AND SERENITY CAN BE SEEN FROM THE OVERSIZED COVERED DECK, AS YOU ENJOY YOUR MORNING COFFEE OR STRESS-FREE EVENING

  Judith Caputo Advantage Realty Group, Inc.

  115 Porter Ave, Middlebury, CT 06762
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  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762
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  $75,000 Pending

  • Land
  • 1.64 Acres
  • $45,732 per Acre

  0 Ferndale Ave, Middlebury, CT 06762

  For Sale: Unique Development Opportunity Offering a rare opportunity to acquire a three-lot subdivision in Middlebury. This property consists of three separate parcels that must be sold together. While previously approved, buyers are responsible for verifying the current status of approvals and conducting their own due diligence. The site presents some challenges due to significant ledge, which

  

  Ken Demirs

  Regency Real Estate, LLC

  (475) 258-7617

  0 Ferndale Ave, Middlebury, CT 06762
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  $17,000 total monthly price

  • 5 Beds
  • 7 Baths
  • 6,600 Sq Ft
  • House for Rent

  372 Tucker Hill Rd, Middlebury, CT 06762

  5 bedrooms 4,3 baths cape house set on 3.5 acres.

  Naima Mazouzi Eagle Eye Realty PLLC

  372 Tucker Hill Rd, Middlebury, CT 06762
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  $695,000 Sold Nov 21, 2025

  • 4,051 Sq Ft
  • $172/SF
  • 36 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 2014

  18 Winding Trail, Middlebury, CT 06762

  Welcome to this luxury home w/ custom features never seen before! This 4000+ sqft, 3 BEDROOM SUITES, 3.2 bath has elegance and comfort, built w/ never seen upgrades. On the most sought-after private cul-de-sac St. and the best location in the complex. Enter through a grand two-story foyer with gleaming hardwood floors, cathedral ceilings & soaring windows that fill the home with natural light.

  Jay Irvine Serhant Connecticut, LLC

  18 Winding Trail, Middlebury, CT 06762
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  Not Listed For Sale

  6 Burr Hall Rd, Middlebury, CT 06762

  6 Burr Hall Rd, Middlebury, CT 06762
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  $465,000

  • 3 Beds
  • 2.5 Baths
  • 2,364 Sq Ft

  105 Jericho Rd, Middlebury, CT 06762

  This beautifully maintained home offers the perfect blend of comfort and space with 3 bedrooms and 2.5 bathrooms. A thoughtfully designed living space welcomes you with a bright and open living room centered around a wood-burning fireplace, creating a warm and inviting atmosphere. A spacious eat-in kitchen provides plenty of room for cooking, dining, and gathering with loved ones. The fully

  Jimmy Edwards Redfin Corporation

  105 Jericho Rd, Middlebury, CT 06762
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  /21

  $3,950 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Townhouse for Rent

  175 Ridgewood Dr Unit 175, Middlebury, CT 06762

  Experience the perfect blend of comfort and luxury in this stunning Ridgewood condominium. Just 3 years young, this 1,812 sq ft home offers a spacious and stylish layout with 3 bedrooms and 2.1 baths. Light-filled interiors showcase modern finishes and an inviting open floor plan designed for today's lifestyle. Enjoy access to outstanding community amenities including tennis court, an indoor half

  Claudine McHugh Klemm Real Estate Inc

  175 Ridgewood Dr Unit 175, Middlebury, CT 06762
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  $200,000 Sold Nov 20, 2025

  • Land
  • 4.56 Acres
  • $43,860 per Acre

  • 22 Days On Market

  1070 Long Meadow Rd, Middlebury, CT 06762

  Welcome to the perfect location for your dream home in beautiful Middlebury, CT. This level, build-ready lot is ideally situated on a quiet private cul-de-sac road, offering the peace and privacy you've been looking for. Backing up to protected open space, the property provides a serene natural setting surrounded by mature trees and nature. The lot has already been cleared, saving you time and

  Alana Wall-Galvin Suburban Homes & Condos

  1070 Long Meadow Rd, Middlebury, CT 06762
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  Est $1,514,288 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,363 Sq Ft

  397 White Deer Rock Rd, Middlebury, CT 06762

  397 White Deer Rock Rd, Middlebury, CT 06762
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  $649,900

  • 4 Beds
  • 3 Baths
  • 2,878 Sq Ft

  72 Carriage Dr, Middlebury, CT 06762

  A grand Cape Cod-style home, nestled in a wonderful and convenient neighborhood. The interior has been freshly painted, and the main level features primarily hardwood flooring. Just off the foyer, you'll find a sunken living room that welcomes you. The spacious eat-in kitchen has been remodeled and opens to the formal dining room, making it perfect for entertaining. Adjacent to the kitchen is a

  Justin Bette Joseph Bette REALTORS Inc

  72 Carriage Dr, Middlebury, CT 06762
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  $449,900 Sold Nov 19, 2025

  • 1,744 Sq Ft
  • $258/SF
  • 162 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1969

  190 Allerton Farms Rd, Middlebury, CT 06762

  Custom-Built Ranch - A Rare Find in Middlebury! Discover this exceptional custom-built ranch featuring 2 bedrooms and 2.5 baths. A large country kitchen, formal dining room, sunken living room and great room complete the main level of the home. The walk-out lower level is finished, offering a summer kitchen, spacious family room, and convenient laundry area-perfect for entertaining or extended

  Mary Ann Hebert BHGRE Gaetano Marra Homes

  190 Allerton Farms Rd, Middlebury, CT 06762
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  Est $549,076 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  436 Judd Rd, Southbury, CT 06488

  436 Judd Rd, Southbury, CT 06488
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  $750,000

  • 4 Beds
  • 3.5 Baths
  • 2,806 Sq Ft

  80 Pine Hollow Dr, Middlebury, CT 06762

  Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting

  Gina Farra Keller Williams Realty

  80 Pine Hollow Dr, Middlebury, CT 06762
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  $380,000 Sold Nov 17, 2025

  • 1,499 Sq Ft
  • $254/SF
  • 38 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1940

  146 Richardson Dr, Middlebury, CT 06762

  Timeless charm and warmth fill this beautifully maintained 3 bed, 1.5 bath Middlebury home. The main level showcases original hardwood floors, custom built-ins, and a spacious living room centered around a working Heatilator fireplace - an inviting spot to gather and unwind. The formal dining room features elegant built-ins and a picturesque bay window that fills the space with natural light,

  Nicholas Greene eXp Realty

  146 Richardson Dr, Middlebury, CT 06762
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  Est $1,792,155 Not Listed For Sale

  • 4 Beds
  • 6.5 Baths
  • 4,954 Sq Ft

  40 Winthrop Dr, Middlebury, CT 06762

  40 Winthrop Dr, Middlebury, CT 06762
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  $785,000

  • 4 Beds
  • 4 Baths
  • 3,360 Sq Ft

  200 N Farm Rd, Middlebury, CT 06762

  Nestled in the serene & sought-after North Farm Road neighborhood of Middlebury, this property offers approximatley 3,360 sq ft of living space on a generous 2.54 acre lot! This custom designed home will have you living in your own VT style home with a blend of privacy & convenient access to town! As you enter the home you will notice the great room with the floor to ceiling custom stone hearth

  Jackie Desmarais Showcase Realty, Inc.

  200 N Farm Rd, Middlebury, CT 06762
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  $975,000 Sold Nov 17, 2025

  • 3,471 Sq Ft
  • $281/SF
  • 4 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1995

  82 Mirey Dam Rd, Middlebury, CT 06762

  Welcome to 82 Mirey Dam Road, Middlebury, CT, a stunning colonial oasis tucked away on 2.74 acres of mature, peaceful landscaping in one of the area's most sought-after neighborhoods. From the moment you arrive, you'll feel the sense of calm this property conveys. Lush landscaping, mature trees, and careful design grant privacy and serenity. The heated saltwater inground pool and outdoor spaces

  Jetlir Kulla Coldwell Banker Realty

  82 Mirey Dam Rd, Middlebury, CT 06762
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  Est $630,727 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft

  740 Whittemore Rd, Middlebury, CT 06762

  740 Whittemore Rd, Middlebury, CT 06762
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  $889,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,220 Sq Ft

  383 Leonard Rd, Middlebury, CT 06762

  Welcome to your dream home...just for holidays-a beautifully designed 3220 sq ft NEW CONSTRUCTION offering warmth, space and flexibility for today's modern family. With 4 generous bedrooms and 3.5 bathrooms, this home invites you to live, laugh and grow in comfort. You have to see in person to appreciate the design of each of the bedrooms with their one full bath and double closet space. The

  Koco Pela William Raveis Real Estate

  383 Leonard Rd, Middlebury, CT 06762
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  $456,000 Sold Nov 17, 2025

  • 1,340 Sq Ft
  • $340/SF
  • 54 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1975

  18 E Ridge Dr, Middlebury, CT 06762

  Lovingly Maintained Home in Desirable Middlebury Location Nestled in one of Middlebury's most sought-after neighborhoods, this lovingly maintained home offers comfort, convenience, and timeless charm on a level, private lot-perfect for relaxing or entertaining. Located in a top-rated, award-winning school district, this home is ideal for families seeking both community and quality education.

  Beth Santos Showcase Realty, Inc.

  18 E Ridge Dr, Middlebury, CT 06762
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  Est $546,032 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,611 Sq Ft

  212 Breakneck Hill Rd, Middlebury, CT 06762

  212 Breakneck Hill Rd, Middlebury, CT 06762
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  $925,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,878 Sq Ft

  22 Somerset Dr, Middlebury, CT 06762

  TO BE BUILT. One of the most desirable neighborhoods in Middlebury! The Avalon Farms community is comprised of lovely homes, manicured lawns, and beautiful gardens resulting in a unique aesthetic. The Cambridge model showcases a classic design combined with today's "must haves" that will meet all your expectations of an open floor plan. The great room with a cathedral ceiling, fireplace, and

  Ellie Gollenberg BHGRE Gaetano Marra Homes

  22 Somerset Dr, Middlebury, CT 06762
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  $238,700 Sold Nov 17, 2025

  • 1,136 Sq Ft
  • $210/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

  3 Pommel Ln, Middlebury, CT 06762

  Fantastic opportunity to own this well-maintained 2-bedroom, 2-bath duplex with a 1-car garage in the desirable Steeplechase community! This is one of the affordable units, subject to income restrictions and an application process through the Town of Middlebury (application attached). Pride of ownership shows-original owners have lovingly cared for this home and completed many updates, including

  Heather Dever Showcase Realty, Inc.

  3 Pommel Ln, Middlebury, CT 06762
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  Est $591,685 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  108 White Ave, Middlebury, CT 06762

  108 White Ave, Middlebury, CT 06762
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  $899,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,878 Sq Ft

  294 Christian Rd, Middlebury, CT 06762

  New construction designed to impress the most discerning buyer. The Cambridge Model with 2,878 sq. ft. offers a grand two-story foyer leading to the great room with majestic soaring ceilings, fireplace and beautiful windows giving the space a light and airy feeling. The kitchen and heart of the home has an expansive island, granite countertops, stainless steel appliances and white shaker style

  Ellie Gollenberg BHGRE Gaetano Marra Homes

  294 Christian Rd, Middlebury, CT 06762
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  $600,000 Sold Nov 14, 2025

  • 3,382 Sq Ft
  • $177/SF
  • 110 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2004

  39 Independence Cir, Middlebury, CT 06762

  Set your eyes on this gorgeous home which features 4 bedrooms, 2 full baths & 2 1/2 baths in Middlebury! This beautifully maintained home boasts classic architecture with modern updates, offering the perfect blend of charm and sophistication. You are welcomed as you enter through the front door by a beautiful family room with charming fireplace and high ceilings. From the family room you have an

  Arben Belica William Raveis Real Estate

  39 Independence Cir, Middlebury, CT 06762
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  Est $478,789 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,552 Sq Ft

  28 Jensen Dr, Middlebury, CT 06762

  28 Jensen Dr, Middlebury, CT 06762
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  $721,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  3 Pine Ridge Unit 23, Middlebury, CT 06762

  Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods

  Robert Michaud Michaud Real Estate

  3 Pine Ridge Unit 23, Middlebury, CT 06762
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  $669,900 Sold Nov 12, 2025

  • 3,488 Sq Ft
  • $192/SF
  • 60 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2005

  117 Periwinkle Dr Unit 117, Middlebury, CT 06762

  No detail has been overlooked in the stunning remodel of this elegant home in Benson Woods, Middlebury's premier active adult community. Perched on a premium lot with serene views of the Eight Mile River, this residence offers 3-4 bedrooms, 2 full baths, and 2 half baths across a thoughtfully designed layout. Step inside to discover custom interior trim, rich wood flooring, and a chef's kitchen

  Mary Ann Hebert BHGRE Gaetano Marra Homes

  117 Periwinkle Dr Unit 117, Middlebury, CT 06762
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  Est $419,536 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  109 Yale Ave, Middlebury, CT 06762

  109 Yale Ave, Middlebury, CT 06762
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  $548,828 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,462 Sq Ft

  0 N Benson Rd Unit 55 24086408, Middlebury, CT 06762

  An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

  Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 55 24086408, Middlebury, CT 06762
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  $480,000 Sold Nov 07, 2025

  • 2,496 Sq Ft
  • $192/SF
  • 113 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2011

  30 Nick Rd, Middlebury, CT 06762

  Wake up with a smile in this spacious 2-3 bedroom cape style home in a quiet neighborhood. Originally built in 1950, it was re built and expanded in 2011, and it has a great deal to offer, including an expansive 17' X 9' entry that leads to the 26' X 16' living room. In addition the eat in kitchen has access to the deck overlooking the private yard. This home also features a dining room, a

  Donna Bannon BHGRE Gaetano Marra Homes

  30 Nick Rd, Middlebury, CT 06762
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  Est $437,739 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,236 Sq Ft

  145 Algin Dr, Middlebury, CT 06762

  145 Algin Dr, Middlebury, CT 06762
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  $545,400 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,206 Sq Ft

  0 N Benson Rd Unit 64 24077175, Middlebury, CT 06762

  An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

  Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 64 24077175, Middlebury, CT 06762
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  $575,000 Sold Nov 06, 2025

  • 3,477 Sq Ft
  • $165/SF
  • 216 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2007

  1 Dogwood Ct Unit 1, Middlebury, CT 06762

  Wow-this is it! The original model home is back on the market for the first time, offering exceptional quality and design. This desirable Dickinson-style home, originally built as the model, is impeccably finished on all three levels. The spacious dining area flows seamlessly into a vaulted living room with a cozy fireplace and sliders leading to a private deck. The light-filled kitchen features

  Joyce Drakeley Drakeley Real Estate, Inc.

  1 Dogwood Ct Unit 1, Middlebury, CT 06762
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  Est $547,671 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,908 Sq Ft

  18 Jericho Rd, Middlebury, CT 06762

  18 Jericho Rd, Middlebury, CT 06762
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  /2

  $699,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,877 Sq Ft

  14 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 14 Deer Run Rd(aka Lot 19) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

  Jodi Dawley Real Estate Two

  14 Deer Run Rd, Middlebury, CT 06762

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