Middlebury, CT Houses for Sale

Exceptional Craftsmanship & Refined Luxury. Welcome to 76 Three Mile Hill Rd, where modern updates meet timeless elegance. Completely renovated in 2024, this stunning home is a true masterpiece of design, featuring intricate millwork-like coffered ceilings and thoughtful detailing that infuse warmth and character throughout. The craftsmanship and luxury are felt throughout this home featuring 4

Lisa Clarke Dave Jones Realty, LLC

Middlebury Modern. Authentic c.1962 Mid-Century Modern Designed by Noted Architect Andrew S Cohen as his Personal Residence. This Largely Untouched Modernist is Set Quietly on Nearly 1-Acre. Walls of Glass & Dark Stone Floors Showcase the Signature Elements of the Era. 4 Bedrooms, 2.5 Baths Include an en-suite Primary Bedroom with Dressing Room & Balcony. Large Eat-in Kitchen Adjacent to Family

Graham Klemm Klemm Real Estate Inc

Built in 1911, this four square colonial has so many fabulous vintage qualities including a beautiful, generously sized front entry, arched doorways, custom moldings and so much more. The main level offers a spacious eat in kitchen, formal living and dining rooms as well as a 21 x 13 heated sunroom overlooking rolling hills and distant views. On the second level, 2 bedrooms and a beautifully

Donna Bannon BHGRE Bannon & Hebert

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

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 Bannon & Hebert

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 Bannon & Hebert

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) 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

Lake Shore Drive is just a short walk from the beautifully preserved Long Meadow Pond, a 117-plus acre body of water known for its fishing and kayaking. This home is perfectly in keeping with this idyllic setting, as it is a quintessentially charming ranch, a style of home known for its open and inviting floor plan. There is a confidence in your investment that comes with purchasing a newly

Michael Caporizzo William Pitt Sotheby's Int'l

Highest and Best By Saturday, April 26th at midnight. Offers will be reviewed Sunday the 27th. Beautifully maintained by its original owners, this stunning home offers a peaceful retreat with thoughtful design throughout. The bright, open-concept floor plan is perfect for entertaining, spending time with loved ones, or enjoying quiet moments at home. Expansive windows and the back deck offer

Christina Zainc BHGRE Bannon & Hebert

Charming Move-In Ready Ranch in the Heart of Middlebury Welcome home to this beautifully updated ranch-style gem, ideally located in the heart of Middlebury. Set on a quiet street just steps from the scenic Middlebury Greenway Trail, this home offers comfort, style, and convenience all in one. The recently renovated eat-in kitchen is a showstopper, featuring granite countertops, subway tile

Jonna Dibble BHGRE Bannon & Hebert

This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn with 2 garage doors, loft area & an attached green house! The main house features a grand foyer with granite flooring, a very large, formal dining room & a generous sized formal living room/music room. The eat-in kitchen area is large enough to hold an 8 seat table & chairs & has slider access to the deck.

Jackie Desmarais Showcase Realty, Inc.

Welcome to 115 Marney Drive! This spacious split level home has so much to offer to a family of any size! Not only does it have 3 bedrooms and 2.5 baths, it also has a large living room and dining area great for entertainment. The lower level has a finished bedroom and den with fireplace for additional guests. This house has had many updates since 2018 including a new roof and gutters with gutter

Allysa DeRosa Mapleridge Realty

Three bedroom Cape Cod style home in the heart of Middlebury, CT! Sitting on a corner lot, this cozy Cape offers a first floor bedroom connected to a half bath, formal living and dining rooms, and spacious eat-in kitchen. Immediately off the living room is an enclosed porch that provides additional space for a future home office. Upstairs find two additional bedrooms with shared full bath. Plenty

Katherine Parlato Drakeley Real Estate, Inc.

Welcome to 138 Skyline Dr, Middlebury, CT a beautifully maintained ranch-style home with a finished basement and in-law suite! This home offers the perfect blend of comfort, convenience, and versatility. Step inside the main level to find three spacious bedrooms, that include a primary bedroom with ensuite bathroom, plus a bonus office space, a bright living area, and a well-appointed kitchen.

Diana Mashni RE/MAX One

Welcome to 28 Maple Drive, a classic gem in the heart of Middlebury, Connecticut, where charm and comfort meet timeless design. This meticulously maintained single-family home, built in 1950, offers 1,596 square feet of thoughtfully designed living space. With 3 spacious bedrooms, 3.5 bathrooms, and a warm, inviting layout, this home is perfect for both entertaining and everyday living. A fully

Dean Giatas William Raveis Real Estate

Antique lovers alert! Enjoy this quintessential 1803 Colonial on 1.026 acres, nestled within the picturesque conservation protected 7.3 acre land containing Fenn Pond. You'll own a piece of history, with the privacy, character and tradition of its era, including wide board floors, 7 fireplaces, and front and back staircases. Delightful finds everywhere! The magical setting contains stone walls,

Mary Helen Levine Mary Helen Levine Real Estate LLC

* TO BE BUILT * WATERBURY ADDRESS, BUT WITH THE AMBIANCE OF MIDDLEBURY! THIS VERY PRIVATE 1 ACRE REAR LOT YIELDS A SUBURBAN FEEL, BUT W/ THE CONVENIENCES OF PROXIMITY TO HIGHWAYS AND SERVICE OF PUBLIC UTILITIES! TRULY A REAR OFFERING! 3/4 BED, 2.5 BATH RSD RANCH W/ VAULTED CEILING & ALL OF TODAY'S DESIGN FLAIR! LOOKING FOR A FAMILY COMPUND? THERE IS A 3/4 ACRE SISTER LOT ADJACENT TO THIS ONE

Scott Tedesco Tedesco Real Estate

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

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is ready to move in to!! This home is a 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

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

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run Road (aka Lot 13) 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