Middlebury Real Estate

Welcome to Middlebury, Connecticut – a charming town nestled in the picturesque landscapes of New Haven County. With its rich history, vibrant community, and stunning natural beauty, Middlebury offers the perfect blend of small-town charm and modern conveniences.

Founded in the late 17th century, Middlebury boasts a wealth of historical significance, with beautifully preserved buildings and sites that tell the story of its past. The town is known for its friendly atmosphere and strong sense of community, where neighbors become friends, and local events bring everyone together. From seasonal festivals to farmers' markets, there’s always something happening in Middlebury that fosters a spirit of camaraderie.

Nature enthusiasts will find plenty to love in Middlebury. The town is surrounded by lush greenery, serene parks, and scenic trails, making it an ideal destination for outdoor activities. Enjoy a leisurely hike through the lush woodlands of the Mattatuck State Forest or take a relaxing stroll around Lake Quassapaug, where you can soak in the breathtaking views and enjoy a picnic by the water.

Middlebury is also conveniently located near major highways, providing easy access to nearby cities like Waterbury and New Haven. This means residents can enjoy the tranquility of suburban life while still being just a short drive away from urban amenities, shopping, and dining options.

As you explore the real estate opportunities in Middlebury, you’ll discover a range of charming homes that reflect the town’s character and appeal. Whether you’re a first-time homebuyer or looking for a peaceful retreat, Middlebury is a place where you can truly feel at home. Come experience the warmth and beauty of Middlebury, where community and nature thrive harmoniously!

Newest Listings in Middlebury

$870,000

4 Beds ⋅ 6 Baths ⋅ 24219437 MLS

Welcome to 203 North Farm Road, a retreat that perfectly captures the essence of classic New England charm blended with sophisticated luxury. Set on a sprawling, private 3.4-acre lot in one of Middlebury's most sought-after neighborhoods, this 2005-built estate offers an unparalleled sense of space and tranquility. Spanning over 4,300 square feet, the home is defined by its grand proportions and thoughtful layout. The main level is designed for both effortless entertaining and comfortable daily living, featuring exceptionally spacious rooms filled with natural light. The upper level is a rare find, boasting four generous bedrooms, each serving as a private sanctuary with its own dedicated en-suite bathroom. With a total of four full and two half baths, the home provides convenience and privacy for everyone. Outside, the expansive acreage offers a serene backdrop for outdoor enjoyment and a true escape from the everyday. This is a unique opportunity to own a stately residence in a premier location. Sale is subject to Probate Court approval.

203 N Farm Rd, Middlebury

$395,000

3 Beds ⋅ 1 Baths ⋅ 24218765 MLS

Take special note of this delightful, warm, inviting, 3-bedroom 1-bath ranch home nestled in one of Middlebury's established sub-divisions! Situated on .34 acres & serviced by public water & sewers, this home has been very well maintained. It has hosted many gatherings for decades & it is now available for the next buyer's future enjoyment! The eat-in kitchen has been previously remodeled & features oak cabinets, tile flooring, recessed lighting, a ceiling fan & access to the family room. The cozy family room features a built-in bookcase, paneled walls & w-w carpeting & is a great place to relax, read & share conversations! This family room accesses the side & rear yards. Enjoy the living room with its wood burning FP, ideal for chilly New England days! The 3 bedrooms, L.R. & hall, feature w-w carpeting over wood floors! Note the attractive crown molding in many of the rooms, along with excellent closet storage! The lower-level basement features an under-house garage with gar. door opener. It provides easy access to the main level living area. There is a laundry hook-up in the unfinished basement. The boiler & water heater are heated with oil & are upgrades! Great workshop & storage area in basement! Move in & make this your "HAPPY PLACE"!

25 Southview Ave, Middlebury

$569,900

24218144 MLS

This is an exceptional opportunity to create your dream home in an area of fine homes. Three lots, sold as a package, provide over six acres of stunning land in one of Middlebury's most desirable neighborhoods. Extending the road will be necessary for the three separate lots unless they are combined into a single parcel. Enjoy picturesque views of Mirey Pond. Builder packages are also available.

14 Mirey Dam Rd, Middlebury

203 Sugar Maple Way Unit 203, Middlebury

$589,900

2 Beds ⋅ 3 Baths ⋅ 24213697 MLS ⋅ Benson Woods BLDG.

Experience maintenance-free living at its finest in Benson Woods, a premier 55+ community in Middlebury. This townhome features an open, main-level layout highlighted by a sun-drenched great room with soaring ceilings, hardwood floors, and a natural gas fireplace. The eat-in kitchen comes well-appointed with rich wood cabinetry, granite countertops, and stainless steel appliances. Retreat to the main-floor primary suite, complete with tray ceiling, dual walk-in closets, and a spa-like bath featuring dual sinks, makeup vanity, and a walk-in shower. A versatile den, half bath, laundry room, and access to the attached two-car garage complete the main level. Upstairs, a spacious loft with a private balcony overlooks the great room, alongside a second bedroom, huge closet, and full bath. The expansive, unfinished basement offers ample ceiling height, natural light, yard-access walk up hatch, active radon mitigation system, and rough-in plumbing for a future bathroom. This unit was completed in 2013.

203 Sugar Maple Way Unit 203, Middlebury

$439,900

3 Beds ⋅ 3 Baths ⋅ 24214190 MLS

BUYERS Remorse! Don't miss out on one of Middlebury's best properties! Set on nearly half an acre in one of Middlebury's most desirable neighborhoods, this 3-bedroom, 2.5-bath Colonial blends timeless character with everyday comfort. Gleaming hardwood floors run throughout the home, anchoring an open, inviting layout built for both daily living and entertaining. The heart of the home is a spacious family room crowned by a dramatic cathedral ceiling and ceiling fan, a bright and airy retreat that flows naturally into the rest of the main level. The kitchen is ready to cook in and gather around, featuring granite countertops, a breakfast bar, and stainless appliances including a gas cooktop. Generous living and dining rooms round out the main floor, each finished in warm hardwood. Upstairs, the primary bedroom suite offers a private full bath and walk-in closet, with two additional well-sized bedrooms, one with its own walk-in closet. Central air, thermopane windows, and zoned heating add year-round comfort and efficiency. Outside, enjoy a level, open lot with plenty of room to play, garden, or relax. A full unfinished basement with garage access and a one-car under-house garage provide ample storage and expansion potential. A brand new basement system with full warranty was installed on 7/14/26, adding to peace of mind.

42 White Ave, Middlebury

$530,000

2 Beds ⋅ 3 Baths ⋅ 24214764 MLS ⋅ Benson Woods BLDG.

Welcome to Benson Woods, a desirable 55+ community! This beautiful freestanding Hopkins Model offers spacious rooms, soaring ceilings, and stylish features throughout. The spacious kitchen is a standout, featuring rich wood cabinetry, stainless steel appliances, abundant counter space, and an oversized center island with seating-perfect for casual dining and entertaining. The kitchen opens to the impressive Living and Dining Room, where soaring ceilings and beautiful hardwood floors create a bright, airy atmosphere. The first-floor primary suite offers two walk-in closets and a private bath with a double-sink vanity, large walk-in shower, and generous soaking tub. A second bedroom, convenient half bath, and laundry room complete the main level, providing comfortable one-floor living. Upstairs, a sun-filled loft overlooks the Living and Dining Room below. A second full bath and separate bonus room offer flexible space for a home office, hobby room, or guests. Additional highlights include hardwood floors in the Living Room, Dining Room, and hallway, a gas range, and a gas hookup on the back deck for convenient grilling-no propane tanks needed! With its inviting layout, spacious kitchen, and versatile living spaces, this lovely Hopkins Model offers the perfect opportunity to enjoy comfortable, low-maintenance living in Benson Woods. Come see all this wonderful home has to offer!

104 Periwinkle Dr Unit 104, Middlebury

$530,000

2 Beds ⋅ 3 Baths ⋅ 24214741 MLS

104 Periwinkle Dr Unit 104, Middlebury

$725,000

4 Beds ⋅ 3 Baths ⋅ 24213859 MLS

Located on a most desirable street in North Farms neighborhood, this well loved and beautifully tended 4 bedroom colonial offers great opportunities for comfortable living and entertaining. Filled with light, this home will dazzle you with its beautiful interior. You can prep meals and enjoy them in the updated eat in kitchen with access to a deck overlooking lush grounds. The spacious family room features a fireplace and provides a peaceful retreat after a busy day. The living and dining rooms are great spaces for entertaining and enjoying special times. You can easily relax in the primary bedroom with a recently updated spa-like bathroom and 2 walk in closets. The upper level also features 3 additional bedrooms, an updated full bath as well as a laundry area. You will also enjoy bonus space on the walk out level. The lovely landscaping contributes to the calm atmosphere that surrounds this home. Rear of property adjoins Flanders Nature, further enhancing the privacy of this property.

106 Mirey Dam Rd, Middlebury

$725,000

5 Beds ⋅ 3 Baths ⋅ 24213699 MLS

At 783 Whittemore Road, beautifully detailed living spaces are paired with something rarely found in a residential property: an expansive garage with room for far more than everyday parking. Extensively rebuilt in 2010, this Middlebury home offers five bedrooms, three full baths, and remarkable flexibility across its living and utility spaces. Beneath the main living level, the multi-vehicle garage offers substantial room for automobile collections, restoration projects, recreational equipment, and a personal workshop. It's a defining feature for a property where practicality and distinctive design share equal billing. Upstairs, vaulted ceilings, exposed beams, skylights, and blue and green zinc paneling lend architectural character throughout. The kitchen features solid wood cabinetry, a professional gas range, French-door wall oven, convection oven, dual Sub-Zero refrigerators, a separate freezer, and two dishwashers, opening to the dining and family rooms. Radiant-heated hardwood floors distinguish the family room. The primary suite includes a sitting area, two walk-in closets, and a bath with heated floors, soaking tub, oversized shower, and heated towel bars. Additional rooms provide flexibility for living or working, complemented by built-in storage and dedicated laundry. A distinctive combination of craftsmanship, comfortable living, and exceptional space for the things that matter beyond the front door.

783 Whittemore Rd, Middlebury

$479,900

3 Beds ⋅ 2 Baths ⋅ 24211870 MLS

Welcome to this inviting Middlebury home, beautifully situated on 1.6 private acres directly along the Greenway and across from picturesque Fenn's Pond. Offering a wonderful combination of privacy, natural beauty, and convenient living, this property is ideal for those who enjoy walking, outdoor activities, and entertaining. A long private driveway leads to the home, providing plenty of parking for family and guests. The fenced backyard features a dedicated play area, creating a wonderful outdoor space for children, pets, or simply enjoying the peaceful surroundings. Inside, the home is filled with natural light, and well-proportioned living spaces. The upper level features a spacious primary bedroom with a private full bath, along with two additional generously sized bedrooms, all with hardwood flooring. A second full bath includes both a tub and separate shower stall. The formal dining room is perfect for hosting and features hardwood flooring and a fireplace, while the oversized Great Room makes an impressive everyday gathering space with its cathedral ceiling and abundance of windows overlooking the private, natural setting. The home's open and light-filled perfect for entertaining. The eat-in kitchen features warm wood cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. Lower level provides additional space, laundry room, garage, and unfinished space for storage. Recent updates include Newer Roof, Septic, Windows, and hot water heater.

961 Middlebury Rd, Middlebury

$485,000

3 Beds ⋅ 2 Baths ⋅ 24209861 MLS

Custom finishes throughout, down to the smart toilet, in this move-in ready 1941 Cape with original character. The kitchen has custom cabinetry, black stone counters, bamboo floors and a sunlit bay window, and original hardwood floors run through the living and dining rooms. Both full baths have black-stone finishes; the primary bath has a double vanity, warm wood, perimeter floor lighting and a waterfall/body-jet shower. Custom built-ins add storage upstairs. The finished lower level offers a second living area, office/gym space, laundry and storage. Out back, the deck opens to a large, tree-lined 0.34-acre yard. Multi-zone ductless heat and AC, with an oil boiler as backup heat. Roof approx. 10 years old. Detached garage. One-year home warranty included, extendable to three. Region 15 schools and convenient I-84 access.

314 Porter Ave, Middlebury

$499,900

4 Beds ⋅ 3 Baths ⋅ 24209000 MLS

For the antique lover, the one with vision and a desire to bring this fabulous home back to its original glory, this is the place for you. Set on over 2 acres within walking distance to Lake Quassapaug, this is a fabulous property. It offers a main house with approximately 1900 s.f.. You'll love the wide board floors, plaster walls and so many details that reflect a fabulous past. In addition to the main house, there is a detached, oversized 2 car garage with a workshop and a finished artist's loft. Enjoy the opportunity for gardens, more fruit trees and a lovely enclosed screened porch. So many original features. This is a spot for the artist, antique lover, the ones who appreciate history and have a desire to own a piece of history. The house is not air conditioned, but the area over the garage has a split system for heat and air conditioning.

802 Charcoal Ave, Middlebury

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Middlebury Real Estate

Newest Listings in Middlebury

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