125

Recently Sold Middlebury, CT Homes

Section Image
  • 27 Sandy Beach 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 Bannon & Hebert

    27 Sandy Beach Rd, Middlebury, CT 06762
  • 25 Carriage Dr, 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 Bannon & Hebert

    25 Carriage Dr, Middlebury, CT 06762
  • 111 Acme 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
  • 61 Carriage 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
  • 117 Bronson 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
  • 70 Steinmann Ave, 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
  • 22 Yale 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 Bannon & Hebert

    22 Yale Ave, Middlebury, CT 06762
  • 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 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
  • 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
  • 122 Northridge Dr, 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
  • 31 Stony Brook Rd, 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
  • 48 Steinmann Ave, 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
  • 141 Camp Rd, 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
  • 450 Long Meadow 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
  • 9 Caveson Ct, 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 Bannon & Hebert

    9 Caveson Ct, Middlebury, CT 06762
  • 40 Winthrop Dr, 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
  • 110 Periwinkle Dr Unit 19, 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
  • 35 Nutmeg Rd Unit B5, 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 Bannon & Hebert

    35 Nutmeg Rd Unit B5, Middlebury, CT 06762
  • 4 Highridge Rd Unit 4, Middlebury, CT 06762

    $565,000 Sold Sep 18, 2024

    • 2,798 Sq Ft
    • $202/SF
    • 75 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2019

    4 Highridge Rd Unit 4, Middlebury, CT 06762

    Discover your dream home, a turn-key masterpiece exuding luxury and comfort. This stunning property features over $100K in upgrades, including fresh paint, custom plantation shutters, new hardwood floors in the primary bedroom and upper level, recessed lighting, custom closets, new stainless steel appliances, a new washer/dryer, a finished lower level, a freshly painted garage floor, and a Level

    Shelley Drakeley Drakeley Real Estate, Inc.

    4 Highridge Rd Unit 4, Middlebury, CT 06762
  • 185 Porter Ave, Middlebury, CT 06762

    $331,900 Sold Sep 16, 2024

    • 1,218 Sq Ft
    • $272/SF
    • 33 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1953

    185 Porter Ave, Middlebury, CT 06762

    REQUESTING HIGHEST AND BEST BY 8/16 AT 6:00PM. Charming Middlebury Cape in a desirable neighborhood close to the Greenway walking path and town center w /hiking trails right behind your private fenced in backyard. This home features 3 bedrooms, 1 full bathroom, public sewer and water, a new furnace and a Generac generator. Perfect home for those seeking comfort convenience and a welcoming

    Beth Santos Showcase Realty, Inc.

    185 Porter Ave, Middlebury, CT 06762
  • 90 Saint Joseph Ave, Middlebury, CT 06762

    $435,000 Sold Sep 11, 2024

    • 1,717 Sq Ft
    • $253/SF
    • 54 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1948

    90 Saint Joseph Ave, Middlebury, CT 06762

    Welcome to this stunning 4-bedroom, 2-full bath ranch located in a highly desirable neighborhood. This beautifully updated home features a gorgeous kitchen equipped with granite countertops and stainless steel appliances. The gleaming hardwood floors throughout the home add warmth and elegance to the spacious living areas. Both bathrooms are completely remodeled, offering modern fixtures and

    Robert Marucci Better Living Realty, LLC

    90 Saint Joseph Ave, Middlebury, CT 06762
  • 67 Algin Dr, Middlebury, CT 06762

    $440,000 Sold Sep 09, 2024

    • 2,376 Sq Ft
    • $185/SF
    • 80 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1965

    67 Algin Dr, Middlebury, CT 06762

    Meticulously maintained Middlebury Ranch on quiet dead end street. One owner home has been lovingly maintained. 3 bedrooms, 2.1 baths, primary w/ half bath, all bedrooms w/ hard flrs,full bath, living room w/ hard flrs with fireplace w/pellet insert. Eat in kitchen w/ stainless appliances leads to family room w/ laminate flooring. Large deck overlooks pristine level backyard with woods for

    Beth Santos Showcase Realty, Inc.

    67 Algin Dr, Middlebury, CT 06762
  • 150 Carriage Dr, Middlebury, CT 06762

    $620,000 Sold Aug 30, 2024

    • 2,492 Sq Ft
    • $249/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1963

    150 Carriage Dr, Middlebury, CT 06762

    Welcome home to this spacious 4 bedroom, 21/2 bath Colonial located on a lovely desirable Middlebury neighborhood. A perfect blend of functionality and desirable living in region 15 school district. This floor plan offers great flow for entertaining. A formal foyer leads to a front to back living room with oversized windows, hardwood floors and a wood burning fireplace. The remodeled kitchen with

    Colleen Burne Coldwell Banker Realty

    150 Carriage Dr, Middlebury, CT 06762
  • 28 Brookside Dr, Middlebury, CT 06762

    $660,000 Sold Aug 29, 2024

    • 3,512 Sq Ft
    • $188/SF
    • 127 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2005

    28 Brookside Dr, Middlebury, CT 06762

    Welcome to your dream colonial home nestled within the picturesque Brookside Development! This stunning residence boasts timeless elegance and modern comforts throughout, offering a lifestyle of luxury and convenience. Step inside and be greeted by the grandeur of the dramatic two-story family room, adorned with a captivating stone-faced fireplace featuring a woodstove insert, perfect for cozy

    Heather Crabtree Coldwell Banker Realty

    28 Brookside Dr, Middlebury, CT 06762
  • 3 Oakwood Dr Unit 2, Middlebury, CT 06762

    $695,831 Sold Aug 27, 2024

    • 2,290 Sq Ft
    • $304/SF
    • 71 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2023

    3 Oakwood Dr Unit 2, 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

    3 Oakwood Dr Unit 2, Middlebury, CT 06762
  • 129 Glenwood Ave, Middlebury, CT 06762

    $292,500 Sold Aug 20, 2024

    • 986 Sq Ft
    • $297/SF
    • 39 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1930

    129 Glenwood Ave, Middlebury, CT 06762

    This adorable and quaint home is perfect for those starting out or for anyone looking to downsize. Full of charm and character both inside and out this home features beautiful wood flooring, fireplace, dining room, eat in kitchen and two bedrooms upstairs with full bath. Outside enjoy the beautiful yard with the gardens and patio. The living room has a door to the upper level patio complete with

    Susan Hotchkiss Realty ONE Group Connect

    129 Glenwood Ave, Middlebury, CT 06762
  • 8 Oakwood Dr Unit 10, Middlebury, CT 06762

    $695,521 Sold Aug 13, 2024

    • 2,290 Sq Ft
    • $304/SF
    • 83 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2023

    8 Oakwood Dr Unit 10, 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

    8 Oakwood Dr Unit 10, Middlebury, CT 06762
  • 2 Northwood Dr, Middlebury, CT 06762

    $465,000 Sold Aug 09, 2024

    • 1,876 Sq Ft
    • $248/SF
    • 54 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1962

    2 Northwood Dr, Middlebury, CT 06762

    This wonderful Split Level is located in the heart of the charming Three Mile Hill neighborhood. Let's start with what makes this home so special! City Water and City Sewers, 2 Full and Newly Remodeled Baths, Updated Stainless Steel Kitchen Appliances, 2 Floor to Ceiling Fireplaces (on the main and lower levels), Large Lower Level Family Room, and Recessed Lighting. If that isn't enough to make

    Michael Magas BHGRE Bannon & Hebert

    2 Northwood Dr, Middlebury, CT 06762
  • 420 Bioski Rd, Middlebury, CT 06762

    $425,000 Sold Aug 07, 2024

    • 1,900 Sq Ft
    • $224/SF
    • 414 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2020

    420 Bioski Rd, Middlebury, CT 06762

    Welcome to your new home in beautiful historic Middlebury CT. Built in 2020, 420 Bioski Road is a 5-bedroom 3 Full Bath beauty that sits on just under one acre of land. The open concept main level with living room access to the deck is perfect for entertaining. The main level also has 2 bedrooms, perfect for guests or a home office. The kitchen which can also be accessed from the attached 2 car

    Yosheka Robinson Century 21 Scala Group

    420 Bioski Rd, Middlebury, CT 06762
  • 14 Dogwood Ct, Middlebury, CT 06762

    $610,000 Sold Aug 06, 2024

    • 3,477 Sq Ft
    • $175/SF
    • 149 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2006

    14 Dogwood Ct, Middlebury, CT 06762

    CHOICE LOCATION WITH GORGEOUS VIEWS! This home was one of the first ones to be built by Ginsburg Development and it was built with quality, care and craftsmanship. Desirable Dickinson style home with an open floor plan and just a quick walk to the pool and clubhouse. This lovely home features an open floor plan. Living room has a gas fireplace with a custom mantel, hardwood floors and leads to a

    Marian Van Egas Berkshire Hathaway NE Prop.

    14 Dogwood Ct, Middlebury, CT 06762
  • 183 Three Mile Hill Rd, Middlebury, CT 06762

    $571,000 Sold Aug 01, 2024

    • 2,114 Sq Ft
    • $270/SF
    • 26 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1941

    183 Three Mile Hill Rd, Middlebury, CT 06762

    Discover Your Dream Home: Nestled on a 2-acre lot, this well-maintained Cape-style home offers an idyllic retreat with 4 bedrooms, 2 full baths, and a 2-car garage, plus city water and sewers. Indulge in luxury in the remodeled eat-in kitchen featuring updated cabinets, quartz countertops, double ovens, and an electric cooktop, complemented by an island with a prep sink and french doors leading

    Nancy Addessio Showcase Realty, Inc.

    183 Three Mile Hill Rd, Middlebury, CT 06762
  • 138 Regan Rd, Middlebury, CT 06762

    $430,026 Sold Aug 01, 2024

    • 1,713 Sq Ft
    • $251/SF
    • 56 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1941

    138 Regan Rd, Middlebury, CT 06762

    Large Cape in in an excellent location, less than 1/4 mile to Middlebury Rd and the Middlebury Greenway. This 3 bedroom 1.5 bath has been kept in excellent condition. The 3 bedrooms upstairs all have hardwood floors, and you will find original built ins and a full bath. Dining and living rooms are hardwood floors as well. The eat in kitchen has a breakfast nook, granite counters and exits to the

    David Landau RE/MAX Right Choice

    138 Regan Rd, Middlebury, CT 06762
  • 294 Porter Ave, Middlebury, CT 06762

    $335,000 Sold Aug 01, 2024

    • 1,109 Sq Ft
    • $302/SF
    • 4 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1949

    294 Porter Ave, Middlebury, CT 06762

    Attention cape lovers!!! This cozy, well maintained cape offers an open and inviting main level with a large living room, french doors leading out to the backyard and private garden patio with cascading waterfall, an updated kitchen with hickory cabinets, granite countertops, stainless steel appliances, and a breakfast bar which extends to the sun-filled dining room. Hardwood floors throughout

    Michelle Pavia William Raveis Real Estate

    294 Porter Ave, Middlebury, CT 06762
  • 405 Chestnut Cir Unit 77, 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
  • 407 Chestnut Cir Unit 78, 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
  • 403 Chestnut Cir Unit 76, 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
  • 401 Chestnut Cir Unit 75, 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
  • 409 Chestnut Cir Unit 79, Middlebury, CT 06762

    $710,000 Sold Mar 07, 2025

    • 2,292 Sq Ft
    • $310/SF
    • 17 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 2024

    409 Chestnut Cir Unit 79, Middlebury, CT 06762

    Construction is now underway on the final homesite in the highly sought-after Phase 3 of Chestnut Circle, featuring 5 exclusive Simsbury Elite homes on a private cul-de-sac! This particular home boasts numerous upgrades, including a walkout basement with 9-foot foundation walls, an expanded kitchen with a center island, prefinished hardwood floors on the main level, a spacious 10x20 deck off the

    Jodi Dawley Real Estate Two

    409 Chestnut Cir Unit 79, Middlebury, CT 06762
  • 185 Curtis Farms Rd, Middlebury, CT 06762

    $570,000 Sold Oct 01, 2024

    • 2,240 Sq Ft
    • $254/SF
    • 1 Day On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    185 Curtis Farms Rd, Middlebury, CT 06762

    Welcome to 185 Curtis Farms Road in Middlebury! This beautiful home sits on 2.3 acres and features 4 bedrooms, 2.5 baths, and a finished basement. Enjoy the spaciousness of an oversized two-car garage and a 480 sq ft outdoor patio, perfect for entertaining. With a newer roof and modern amenities, this home offers convenience and comfort. Located in the award-winning Region 15 School District, it

    Ricky Cotton Century 21 AllPoints Realty

    185 Curtis Farms Rd, Middlebury, CT 06762
  • 173 Krodel Rd, Naugatuck, CT 06770

    $360,000 Sold Jul 25, 2025

    • 1,318 Sq Ft
    • $273/SF
    • 182 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1954

    173 Krodel Rd, Naugatuck, CT 06770

    This charming 3-bedroom house is a must see! Recently updated with a brand new kitchen and bathroom. It also boosts new floors throughout, giving the interior a modern and fresh look. Step outside to the inviting back yard, where a sparkling in ground pool awaits your enjoyment. The entire house has been freshly painted, adding to its appeal. Don't miss the opportunity to make this move in ready

    Tanya Silva YellowBrick Real Estate LLC

    173 Krodel Rd, Naugatuck, CT 06770

Showing Results 81 - 120, Page 3 of 4

Connecticut Middlebury

Recently Sold Real Estate & Homes in Middlebury, CT

How to Buy a Home How to Sell a Home How to Rent a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group