Recently Sold Middlebury, CT Homes

• 

  $682,921 Sold Dec 20, 2024

  • 2,290 Sq Ft
  • $298/SF
  • 86 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2023

  7 Oakwood Dr Unit 4, Middlebury, CT 06762

  Welcome to Granite Woods, a unique, brand new in-town 55+ home community featuring 24 Cape-style classic homes in the heart of tranquil Middlebury Village, walkable to restaurants, coffee shops, shopping, and direct access to the popular Middlebury Greenway Trail. Phase One is currently underway offering five unique designs that make living in style easy for years of family enjoyment while

  Robert Michaud Michaud Real Estate

  7 Oakwood Dr Unit 4, Middlebury, CT 06762
• 

  $629,000 Sold Dec 13, 2024

  • 3,508 Sq Ft
  • $179/SF
  • 39 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1957

  706 Charcoal Ave, Middlebury, CT 06762

  Welcome to 706 Charcoal Ave! Here you'll find an impeccably kept 5 BR / 3 bath home that provides a versatile floor plan to suit your family's needs. This home underwent an extensive renovation and expansion in 2013. The main level boasts a light filled "open plan" which encompasses the living room, dining and the eat in kitchen. The lower-level w/walk out presents 1,300 sq. ft. of living

  Kathleen Conetta Berkshire Hathaway NE Prop.

  706 Charcoal Ave, Middlebury, CT 06762
• 

  $715,000 Sold Dec 11, 2024

  • 3,253 Sq Ft
  • $220/SF
  • 165 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1982

  122 Crest Rd, Middlebury, CT 06762

  Recently Refreshed! Ready for new owner(s) to Customize and Enjoy! Charming, comfortable and private home with elegant details. Located in the area of Westover School. Light filled rooms - new Anderson windows throughout. Living room with wide board pine floors and wood burning fireplace. Well equipped kitchen with counter seating. Formal dining room with French doors to a delightful screened

  Jacki Hornish W. Raveis Lifestyles Realty

  122 Crest Rd, Middlebury, CT 06762
• 

  $480,000 Sold Dec 11, 2024

  • 1,854 Sq Ft
  • $259/SF
  • 325 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2022

  106 Periwinkle Dr Unit 17, Middlebury, CT 06762

  Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Durham style is our single level attached home. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car

  Jodi Dawley Real Estate Two

  106 Periwinkle Dr Unit 17, Middlebury, CT 06762
• 

  $25,000 Sold Dec 04, 2024

  • Land
  • 0.92 Acre
  • $27,174 per Acre

  • 63 Days On Market

  135 Washington Dr, Middlebury, CT 06762

  contaminated lot, paperwork from deep, being sold as is. buyer to do due diligence with contaminations and utilities available.

  Richard Pavlik Pavlik Real Estate LLC

  135 Washington Dr, Middlebury, CT 06762
• 

  $515,000 Sold Dec 04, 2024

  • 2,083 Sq Ft
  • $247/SF
  • 69 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1941

  133 1/2 Steinmann Ave, Middlebury, CT 06762

  Welcome to Middlebury and this well-maintained Oversized Cape. This house is full of charm. It has all of the timeless appeals such as multi arches and hardwood floors but with modern updates. The formal living room, complete with a gas fireplace has access to an arched portico. The perfect place to relax. The kitchen has granite counters and stainless-steel appliances with access to both the

  Karen Griffin Coldwell Banker Realty

  133 1/2 Steinmann Ave, Middlebury, CT 06762
• 

  $1,300,000 Sold Dec 04, 2024

  • 9,981 Sq Ft
  • $130/SF
  • 372 Days On Market

  • 4 Beds
  • 7 Baths
  • Built 1999

  7 E Farm Rd, Middlebury, CT 06762

  Come enjoy a unique, elegant, old-world experience designed with artful accents and architectural accentuations throughout. The grand sweeping foyer with porcelain & marble tile flooring, the curved custom stairway, and the 20’ ceiling mirrors that of the grande European Manors. The authentic reproduction of the French porcelain flooring, coupled with multiple French & English influences elevates

  Your Home Group Keller Williams Realty

  7 E Farm Rd, Middlebury, CT 06762
• 

  $440,000 Sold Dec 03, 2024

  • 1,963 Sq Ft
  • $224/SF
  • 19 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2008

  23 Ridgewood Dr Unit 23, Middlebury, CT 06762

  Experience luxury living Middlebury with this maintenance-free luxury condo at Ridgewood! This light-filled end unit offers 4 levels of spacious living, starting with an eat-in kitchen featuring granite countertops, a breakfast bar, gas range, and ample storage. The large bay window floods the space with natural light. Adjacent is an open-concept living and dining room with a cozy gas fireplace

  Jay Irvine Serhant Connecticut, LLC

  23 Ridgewood Dr Unit 23, Middlebury, CT 06762
• 

  $300,000 Sold Dec 02, 2024

  • 1,568 Sq Ft
  • $191/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1945

  326 Lake Shore Dr, Middlebury, CT 06762

  Discover your dream retreat with this 3-bedroom, 2-bathroom home nestled on the serene shores of Lake Shore Dr. Offering direct waterfront access, this property provides stunning views and endless potential to create your ideal lakeside haven. With some TLC, this gem could truly shine-whether you're envisioning a cozy weekend getaway or a year-round residence. Imagine enjoying morning coffee

  Jason Arcuri eXp Realty

  326 Lake Shore Dr, Middlebury, CT 06762
• 

  $660,000 Sold Nov 27, 2024

  • 3,356 Sq Ft
  • $197/SF
  • 104 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1979

  570 Park Road Extension, Middlebury, CT 06762

  This charming Middlebury Dutch Colonial boasts 4+ bedrooms, 3 baths, 2 fireplaces. Walking into the front entrance, you're greeted by a beautiful staircase/two-story foyer flanked by a large dining room with fireplace and crown molding, and a living room with crown molding, both with oversized windows, all with refinished hardwood floors. Through the living room and into the kitchen with dining

  Tom Slekis Berkshire Hathaway NE Prop.

  570 Park Road Extension, Middlebury, CT 06762
• 

  $485,000 Sold Nov 27, 2024

  • 2,492 Sq Ft
  • $195/SF
  • 80 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1959

  213 Steinmann Ave, Middlebury, CT 06762

  Welcome to 213 Steinmann Ave! This exceptional property offers a rare opportunity in Middlebury, featuring a single-family home with a legal accessory apartment (2-family), making it perfect for owner-occupants looking to offset living expenses or a large family desiring separate spaces within one home. This renovated, turn-key property boasts modern amenities and thoughtful design. The top unit

  Konstantinos Milas Milas Realty Advisors

  213 Steinmann Ave, Middlebury, CT 06762
• 

  $485,000 Sold Nov 27, 2024

  • 2,492 Sq Ft
  • $195/SF
  • 82 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1959

  213 Steinmann Ave, Middlebury, CT 06762

  Welcome to 213 Steinmann Ave! This exceptional property offers a rare opportunity in Middlebury, featuring a single-family home with a legal accessory apartment (2-family), making it perfect for owner-occupants looking to offset living expenses or a large family desiring separate spaces within one home. This renovated, turn-key property boasts modern amenities and thoughtful design. The top unit

  Konstantinos Milas Milas Realty Advisors

  213 Steinmann Ave, Middlebury, CT 06762
• 

  $499,000 Sold Nov 27, 2024

  • 2,384 Sq Ft
  • $209/SF
  • 387 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2022

  108 Periwinkle Dr Unit 18, Middlebury, CT 06762

  Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Durham Elite style is our single level attached home with the loft option. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint

  Jodi Dawley Real Estate Two

  108 Periwinkle Dr Unit 18, Middlebury, CT 06762
• 

  $650,000 Sold Nov 21, 2024

  • 2,950 Sq Ft
  • $220/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  6 Colonial Ct, Middlebury, CT 06762

  This gorgeous home with exceptional curb appeal, located on a quiet cul de sac in a great neighborhood, truly exemplifies style and grace from the moment you step inside. The beautiful two-story foyer greets you with an open floor plan that seamlessly flows from the elegant dining room to the fabulous well-appointed kitchen complete with SS appliances, wall oven, granite counter tops and high bar

  Norinne Byrne Calcagni Real Estate

  6 Colonial Ct, Middlebury, CT 06762
• 

  $545,000 Sold Nov 20, 2024

  • 2,442 Sq Ft
  • $223/SF
  • 81 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2006

  203 Sugar Maple Way Unit 203, Middlebury, CT 06762

  Move right into this expansive well-appointed home completed in 2013 of Benson Woods development. Phase 1 and 3 are completely sold out. Phase 2 to be built. This is a rare opportunity to own a larger, upgraded Phase 1 unit. With an attached two car garage opening to the main level with a sunny great room with soaring ceiling height, gas fireplace, ceiling fan and open flow to the dining room and

  Constance Trolle Litchfield Hills Properties LLC

  203 Sugar Maple Way Unit 203, Middlebury, CT 06762
• 

  $818,266 Sold Nov 12, 2024

  • 2,290 Sq Ft
  • $357/SF
  • 281 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2023

  6 Oakwood Dr Unit 11, Middlebury, CT 06762

  Welcome to Granite Woods, a unique, brand new in-town 55+ home community featuring 24 Cape-style classic homes in the heart of tranquil Middlebury Village, walkable to restaurants, coffee shops, shopping, and direct access to the popular Middlebury Greenway Trail. Phase One is currently underway offering five unique designs that make living in style easy for years of family enjoyment while

  Robert Michaud Michaud Real Estate

  6 Oakwood Dr Unit 11, Middlebury, CT 06762
• 

  $645,000 Sold Nov 08, 2024

  • 3,895 Sq Ft
  • $166/SF
  • 186 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1979

  150 Burr Hall Rd, Middlebury, CT 06762

  Price improved and ready to sell! Welcome to your dream home! This contemporary residence offers the perfect blend of modern elegance and comfortable living. Situated on a large, level, and private 2 acre lot on a dead-end road. The home features 4 bedrooms, 2 full baths upstairs and 1 half bath on the main level. Vaulted ceilings offer an open, airy feel. The living room features a floor to

  Heather Dever Showcase Realty, Inc.

  150 Burr Hall Rd, Middlebury, CT 06762
• 

  $660,000 Sold Nov 07, 2024

  • 1,509 Sq Ft
  • $437/SF
  • 143 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  27 Sandy Beach Rd, Middlebury, CT 06762

  Lakefront home in Middlebury on gorgeous Lake Quassapaug! The very special home that you have been waiting for. An architectural beauty, this stone and shingle home has direct water frontage on pristine Lake Quassapaug! Improved with care so that the natural beauty of this home has not been compromised. You will love the beadboard walls and ceilings along with hardwood floors and a gorgeous stone

  Donna Bannon BHGRE Gaetano Marra Homes

  27 Sandy Beach Rd, Middlebury, CT 06762
• 

  $605,000 Sold Nov 04, 2024

  • 2,284 Sq Ft
  • $265/SF
  • 47 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1966

  25 Carriage Dr, Middlebury, CT 06762

  A beautiful home just waiting for new owners. Lovingly maintained, this 3-bedroom home features a front-to-back living room with a fireplace and hardwood floors. The living room opens to a heated sunroom with views of the park-like, private backyard. The French doors lead to a brick patio. Kitchen with high-end appliances including double ovens, gas cooktop, and subzero fridge. Custom cabinets

  Mary Ann Hebert BHGRE Gaetano Marra Homes

  25 Carriage Dr, Middlebury, CT 06762
• 

  $370,000 Sold Nov 01, 2024

  • 1,064 Sq Ft
  • $348/SF
  • 12 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1973

  111 Acme Dr, Middlebury, CT 06762

  You will be very happy living in this well maintained Ranch on a Pretty and Level lot. This home is a perfect condo alternative and more!! Situated on a level .60 acre lot in a desirable subdivision in Middlebury. There is a large, eat in kitchen with a bay window which brings in the nice sunshine. There is a new Stainless Steel Refrigerator and Oven/Range, plenty of cabinet space and a tiled

  Marian Van Egas Berkshire Hathaway NE Prop.

  111 Acme Dr, Middlebury, CT 06762
• 

  $577,000 Sold Nov 01, 2024

  • 2,311 Sq Ft
  • $250/SF
  • 39 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1966

  61 Carriage Dr, Middlebury, CT 06762

  Location, location, location! Perfectly nestled on a lovely Middlebury cul-de-sac. Welcome home to this 4 bedroom, 2 1/2 bath, well maintained colonial. A standout feature is a suitable main floor in-law suite which gives flexibility for owners to use as den, a family room. In addition, upon entering, you will find a comfortable, bright, formal living room with bay window, hardwood flooring,

  Colleen Burne Coldwell Banker Realty

  61 Carriage Dr, Middlebury, CT 06762
• 

  $587,500 Sold Nov 01, 2024

  • 2,522 Sq Ft
  • $233/SF
  • 50 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1952

  117 Bronson Dr, Middlebury, CT 06762

  Rare opportunity in Middlebury! Charming Colonial featuring over 2500 square feet of living space, 4 bedrooms, 2.1 baths, a 2 car garage, an eat-in kitchen with granite countertops and stainless steel appliances, dining area, living room with fireplace and built-ins, sunroom, and first floor primary suite with full bath. The second floor offers three spacious bedrooms, and a walk up attic. The

  Robert Perriello Century 21 AllPoints Realty

  117 Bronson Dr, Middlebury, CT 06762
• 

  $330,000 Sold Nov 01, 2024

  • 1,486 Sq Ft
  • $222/SF
  • 112 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1971

  70 Steinmann Ave, Middlebury, CT 06762

  Welcome to this impeccably updated 4-bedroom, 2-bath ranch-style home, where modern luxury meets eco-friendly efficiency. Located in a peaceful neighborhood, this home showcases a seamless open concept design that blends the stylish kitchen, boasting maple cabinet and a convenient breakfast bar, with expansive living and dining areas. The spacious primary suite serves as a serene retreat with a

  Heather Crabtree Coldwell Banker Realty

  70 Steinmann Ave, Middlebury, CT 06762
• 

  $370,000 Sold Oct 31, 2024

  • 1,053 Sq Ft
  • $351/SF
  • 49 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1926

  22 Yale Ave, Middlebury, CT 06762

  Simple living at its finest! This completely renovated ranch offers the ease of one floor living with many upgrades. The open floor plans welcomes an open space to entertain. The ample kitchen hosts plenty cabinet space for all of your cooking essentials, with a brand new center island, granite countertops, newer cabinets that reach the tall ceilings, newer appliances, plus a large picture window

  Christina Zainc BHGRE Gaetano Marra Homes

  22 Yale Ave, Middlebury, CT 06762
• 

  $535,000 Sold Oct 28, 2024

  • 2,003 Sq Ft
  • $267/SF
  • 17 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1997

  17 Kimberwick Ct Unit 17, Middlebury, CT 06762

  Enjoy a wonderful Lifestyle at the desirable Steeplechase of Middlebury. Free standing home in a planned community with lovely, private grounds, perfect for taking a nice walk in. This home is the Osborn model with two primary bedrooms, one on first floor and one on second floor. Family room with fireplace and a wonderful enclosed seasonal porch. Open living room and dining room with hardwood

  Marian Van Egas Berkshire Hathaway NE Prop.

  17 Kimberwick Ct Unit 17, Middlebury, CT 06762
• 

  $535,000 Sold Oct 28, 2024

  • 2,003 Sq Ft
  • $267/SF
  • 17 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1997

  17 Kimberwick Ct Unit 17, Middlebury, CT 06762

  Enjoy a wonderful Lifestyle at the desirable Steeplechase of Middlebury. Free standing home in a planned community with lovely, private grounds, perfect for taking a nice walk in. This home is the Osborn model with two primary bedrooms, one on the first floor and one on the second floor. Family room with fireplace and off of the kitchen is a wonderful enclosed seasonal porch. The living room and

  Marian Van Egas Berkshire Hathaway NE Prop.

  17 Kimberwick Ct Unit 17, Middlebury, CT 06762
• 

  $895,000 Sold Oct 24, 2024

  • 5,582 Sq Ft
  • $160/SF
  • 80 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1982

  122 Northridge Dr, Middlebury, CT 06762

  Welcome to your dream home! This one-owner custom-built residence is nestled in the heart of one of Middlebury's most sought-after neighborhoods. Offering the perfect blend of luxury, comfort, and convenience, this stunning property features a large and luxurious light filled primary bedroom and bathroom suite. There are 3 additional bedrooms on the second floor and 2 full baths. The first floor

  Heather Dever Showcase Realty, Inc.

  122 Northridge Dr, Middlebury, CT 06762
• 

  $440,000 Sold Oct 23, 2024

  • 2,002 Sq Ft
  • $220/SF
  • 54 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1969

  31 Stony Brook Rd, Middlebury, CT 06762

  Set on a private road, this move in ready 3 bedroom Raised Ranch has plenty of space for living both inside and out. The eat in kitchen features pullout cabinets and pantry, space for meal prep and has tastefully been redone. Access to the private two tier rear deck from the kitchen. Bright living room with wood fireplace adjoins the dining room for a great open feel. On the main level, there are

  Deana Daponte Dave Jones Realty, LLC

  31 Stony Brook Rd, Middlebury, CT 06762
• 

  $445,000 Sold Oct 21, 2024

  • 1,730 Sq Ft
  • $257/SF
  • 34 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1930

  48 Steinmann Ave, Middlebury, CT 06762

  Do not miss the opportunity to own this Rare Two-Family home in beautiful Middlebury, CT. Picturesque views and walking distance to the Middlebury Greenway, Hiking Trails, Restaurants, and more. Pomperaug Regional 15 School District. Whether you are an Investor or looking to Owner Occupy and offset costs with rental income. Two Units.. Each contains 2 bedrooms and 1 full bath with in-unit

  Ardita Vinca Dave Jones Realty, LLC

  48 Steinmann Ave, Middlebury, CT 06762
• 

  $528,000 Sold Oct 21, 2024

  • 2,218 Sq Ft
  • $238/SF
  • 21 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  141 Camp Rd, Middlebury, CT 06762

  Discover your serene retreat in the heart of Middlebury! This stunning contemporary home is nestled amidst lush woods, offering the perfect blend of modern comfort and natural beauty. The spacious living room is bathed in natural light, thanks to expansive skylights, creating an inviting atmosphere for relaxation and entertaining. The primary bedroom is a true sanctuary, featuring a private hot

  Olivia Hardt Berkshire Hathaway NE Prop.

  141 Camp Rd, Middlebury, CT 06762
• 

  $540,000 Sold Oct 18, 2024

  • 3,450 Sq Ft
  • $157/SF
  • 107 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2002

  450 Long Meadow Rd, Middlebury, CT 06762

  Welcome Home! This beautiful 4-bedroom, 2.5-bathroom gem boasts everything you've been looking for. Step inside to find a spacious and inviting floor plan and hardwood flooring throughout the main level. The kitchen is the heart of this home and features a Viking gas cooktop, double wall ovens, and sleek stainless steel appliances. The kitchen is open to the living room with sliders to the deck

  Heather Dever Showcase Realty, Inc.

  450 Long Meadow Rd, Middlebury, CT 06762
• 

  $560,000 Sold Oct 09, 2024

  • 2,050 Sq Ft
  • $273/SF
  • 64 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1996

  9 Caveson Ct, Middlebury, CT 06762

  Steeplechase of Middlebury is a most desirable neighborhood where you can combine the privacy of detached single-family living in a lovely community. This particular house offers a professionally landscaped property with stone walls and plantings and is located at the end of a cul de sac overlooking the pond. The setting is both lush and private. On the interior, a spacious living/dining room

  Donna Bannon BHGRE Gaetano Marra Homes

  9 Caveson Ct, Middlebury, CT 06762
• 

  $1,750,000 Sold Sep 27, 2024

  • 4,954 Sq Ft
  • $353/SF
  • 94 Days On Market

  • 4 Beds
  • 6.5 Baths
  • Built 2001

  40 Winthrop Dr, Middlebury, CT 06762

  Stunning all brick home w/ heated in-ground pool, covered outdoor dining space & main level master set on a private lot on a cul-de-sac of similar homes. In-ground pool w/ spa, fully applianced and covered outdoor kitchen, entertaining area, bar, fireplace. Gorgeous patio w/ pergula. Inside, remodeled eat-in-kitchen, large center island, Stainless Steel appliances including 6 burner Wolf stove,

  John Donato Jr Showcase Realty Tristate

  40 Winthrop Dr, Middlebury, CT 06762
• 

  $609,000 Sold Sep 27, 2024

  • 1,762 Sq Ft
  • $346/SF
  • 325 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2022

  110 Periwinkle Dr Unit 19, Middlebury, CT 06762

  Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Simsbury style is our single level detached home. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car

  Jodi Dawley Real Estate Two

  110 Periwinkle Dr Unit 19, Middlebury, CT 06762
• 

  $232,500 Sold Sep 19, 2024

  • 890 Sq Ft
  • $261/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1984

  35 Nutmeg Rd Unit B5, Middlebury, CT 06762

  This sought-after first-floor unit in Middlebury Commons features a bright kitchen with granite countertops. The primary bedroom boasts a walk-in closet, while the second bedroom or den is equally bright and welcoming. The combined dining and living room area includes a French door that opens to the patio and backyard, perfect for relaxation. With newer carpeting, a heat pump, and central air,

  Mary Ann Hebert BHGRE Gaetano Marra Homes

  35 Nutmeg Rd Unit B5, Middlebury, CT 06762
• 

  $740,000 Sold Aug 06, 2025

  • 2,466 Sq Ft
  • $300/SF
  • 136 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  17 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 17 Deer Run Road (aka Lot 22) is ready to move in to! It is 2400+ sq ft 4 bedroom colonial. 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

  17 Deer Run Rd, Middlebury, CT 06762
• 

  $649,500 Sold Jul 25, 2025

  • 2,292 Sq Ft
  • $283/SF
  • 99 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 2025

  405 Chestnut Cir Unit 77, Middlebury, CT 06762

  Welcome to our final phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

  Jodi Dawley Real Estate Two

  405 Chestnut Cir Unit 77, Middlebury, CT 06762
• 

  $710,500 Sold Jun 20, 2025

  • 2,292 Sq Ft
  • $310/SF
  • 520 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2023

  407 Chestnut Cir Unit 78, Middlebury, CT 06762

  Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

  Jodi Dawley Real Estate Two

  407 Chestnut Cir Unit 78, Middlebury, CT 06762
• 

  $702,500 Sold May 23, 2025

  • 2,292 Sq Ft
  • $307/SF
  • 533 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2023

  403 Chestnut Cir Unit 76, Middlebury, CT 06762

  Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

  Jodi Dawley Real Estate Two

  403 Chestnut Cir Unit 76, Middlebury, CT 06762
• 

  $707,200 Sold Apr 04, 2025

  • 2,292 Sq Ft
  • $309/SF
  • 535 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2023

  401 Chestnut Cir Unit 75, Middlebury, CT 06762

  Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

  Jodi Dawley Real Estate Two

  401 Chestnut Cir Unit 75, Middlebury, CT 06762

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