Middlebury Real Estate

Welcome to Middlebury, Connecticut – a charming town nestled in the heart of New Haven County, where small-town charm meets modern convenience. With its picturesque landscapes, friendly community, and rich history, Middlebury offers an idyllic setting for families, professionals, and retirees alike.

Founded in the 18th century, Middlebury boasts a rich tapestry of history, evident in its well-preserved architecture and local landmarks. The town is known for its stunning natural beauty, featuring lush parks, serene lakes, and scenic trails that invite outdoor enthusiasts to explore. Whether you're hiking in the nearby Mattatuck State Forest or enjoying a leisurely afternoon at Lake Quassapaug, the great outdoors is just a stone's throw away.

Middlebury's community spirit shines through its vibrant local events and festivals, fostering connections among residents. The town is home to a variety of shops, eateries, and services that cater to all needs, making it easy to enjoy the best of both worlds – a tranquil suburban lifestyle with access to urban amenities.

Education is a top priority in Middlebury, with highly-rated schools that provide excellent learning opportunities for children. Families will appreciate the town's commitment to creating a safe and nurturing environment for their kids to thrive.

With its convenient location just a short drive from major highways, Middlebury offers easy access to nearby cities like Waterbury and New Haven, where you can enjoy a plethora of cultural attractions, dining, and entertainment options.

Discover the charm of Middlebury – a place where community, nature, and history come together to create a truly special place to call home.

Newest Listings in 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

BUYER UNABLE TO OBTAIN FINANCING-BACK ON MARKET! 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. A cozy fireplace, 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

$849,900

3 Beds ⋅ 3 Baths ⋅ 24209615 MLS

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) 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.

6 Deer Run Rd, Middlebury

$850,000

3 Beds ⋅ 4 Baths ⋅ 24209325 MLS

Welcome to this beautifully maintained ranch, ideally situated on a quiet cul-de-sac in one of Middlebury's desirable neighborhoods. Set on a private, level 1 acre lot, this 3 bedroom, 3.5 bath home offers comfort, character, and exceptional space for everyday living and entertaining. The inviting open floor plan features a stunning sunken living room, three fireplaces, and a spacious family room. The kitchen and living spaces flow seamlessly to a screened-in porch and newly remodeled deck, creating a wonderful indoor-outdoor entertaining experience. Additional highlights include an attached 3 car garage, partially finished basement, central air, city water and sewer, oil and electric heat, and an auto-start Generac generator. This home is conveniently located minutes from shopping, grocery stores, and major highways. A special home offering privacy, space, and convenience-don't miss it!

25 Juniper Rd, Middlebury

$139,999

24208480 MLS

I'm not just a piece of land - I'm a head start. Imagine arriving at your future home knowing that much of the work that normally comes before construction has already been done. Set on approximately 0.38 acres in desirable Middlebury, I'm ready for someone to bring the vision to life. My survey has been completed, test borings have been performed, and I come with a full set of blueprints and engineering plans for an approximately 2,200 SF home. Instead of starting from scratch, you can start with a plan. WHAT I ALREADY HAVE: * Approximately 0.38 acres * Updated survey completed * Full architectural plans & engineering included * Approved design for approximately 2,200 SF home * Test borings completed * Appraisal available * Permit-ready opportunity * Supporting documentation available upon request Whether you're a builder, investor, or future homeowner, I offer something valuable: time saved and a significant amount of the preliminary work already completed. There's no need to simply imagine what could be here. The vision has already been put on paper. Now it's time to build it. Come take a look at the land, review the plans, and start imagining the home that could soon stand here. LET'S HOME

271 Steinmann Ave, Middlebury

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Middlebury Real Estate

Newest Listings in Middlebury

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