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

$324,900

2 Beds ⋅ 2 Baths ⋅ 24193924 MLS

Welcome to this Middlebury home offering the perfect blend of comfort, functionality, and a desirable location. The home's refreshed interior provides move-in-ready feel designed for everyday living. The property is an excellent opportunity for buyers looking for a home that is ready to enjoy. The home sits on a level lot and is situated directly next to a small brook.

125 Shadduck Rd, Middlebury

$649,900

3 Beds ⋅ 3 Baths ⋅ 24184080 MLS

Ideal location! Beautiful 3-bedroom, 3.5-bath colonial situated at the end of a private cul-de-sac in desirable Middlebury, just minutes from the highway. This bright, sun-filled home features hardwood floors throughout, a spacious family room, custom kitchen with quartz countertops, stainless steel gas range, plus a formal dining room with a brick fireplace. Relax in the skylit sunroom or enjoy the finished lower level with walkout, ideal for an in-law setup, recreation room, or home office. Above the two car garage there is a separate room that could be used as a possible fourth bedroom. Step outside to a spacious, two tiered deck overlooking an exceptionally private backyard with an above ground pool. This house is set on nearly 3 acres, backing directly to the Middlebury Land Trust with an additional shed. This home offers the perfect combination of comfort, privacy, and convenience. Schedule your private showing today!

130 Fairhaven Dr, Middlebury

$339,900

2 Beds ⋅ 1 Baths ⋅ 24113785 MLS

Picture-perfect and completely updated, this classic New England Cape delivers far more than its footprint suggests. A paver walkway, lamppost, and lush hosta gardens frame a storybook exterior with black shutters and stone front steps - genuine curb appeal on one of Middlebury's most established streets. Inside, the open floor plan connects a sun-filled living area to a fully renovated kitchen featuring a quartz-topped center island with seating, two-tone cabinetry with brass hardware, stainless appliances, and a wall of windows overlooking the green backdrop beyond. Crown molding, designer lighting, and thoughtful finishes carry throughout - every detail has been done, so you simply move in. Two bedrooms and a full bath complete this efficient, light-filled layout. Steps from the Middlebury Greenway Trail with easy Route 64 and I-84 access, and served by the award-winning Region 15 school district. A turnkey Connecticut gem.

12 Yale Ave, Middlebury

$479,900

3 Beds ⋅ 3 Baths ⋅ 24191937 MLS

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 was installed on 7/14/26, adding to peace of mind.

42 White Ave, Middlebury

$650,000

3 Beds ⋅ 3 Baths ⋅ 24190947 MLS

Welcome to this beautifully updated contemorary ranch offering an open floor plan, vaulted ceilings, and an inviting sense of space. Nestled among million dollar homes, this property combines comfort, style, and an exceptional location. The spacious living area features a cozy wood burning fireplace and flows seamlessly into the renovated kitchen with abundant cabinetry, a breakfast bar, a coffee station, and a convenient nook, ideal for a home office or a place to sit and relax, overlooking the patio through sliding glass doors. The renovated full bath adds modern appeal, while the private primary suite offers its own full bath, with modern cabinetry, and thoughtfully tucked away closets. Freshly painted inside and out, the home has a clean, warm feel throughout. Outside, enjoy professionally landscaped grounds highlighted by a beautiful rose garden and a brand new Kloter Farm shed. The lower level welcomes you with a foyer leading to a versatile den or flex space, while the expansive basement offers endless possibilities for future living space, a workshop, or abundant storage. Additional features include central air conditioning, new well tank and updated softener, new gutters and downspouts with leaf guards, new hot water heater, new fiberglass doors and an attached two car garage. Move in just in time for the new school year and enjoy all that the award-winning Region 15 School District has to offer!

200 Northridge Dr, Middlebury

$499,000

4 Beds ⋅ 3 Baths ⋅ 24189438 MLS

Highest and Best by Tuesday, the 21st, 5pm. Welcome to this charming four-bedroom traditional Colonial, privately tucked away on a secluded lot while offering the convenience of city sewer. This light and bright home combines timeless character with important modern updates, including a DeGiorgi roof with a transferable warranty, a new driveway, updated electrical panel, and a newer boiler. Inside, a classic center hall foyer with a graceful staircase welcomes you. The spacious eat-in kitchen is ideal for everyday living, while the formal dining room, complete with a charming swinging door, and is perfect for entertaining. The front-to-back living room features a cozy wood-burning fireplace and new sliding glass doors that open to the backyard, creating a seamless connection to outdoor living. A tucked-away office or den with built-ins provides the perfect space for working from home, reading, or relaxing. Upstairs, the generous primary suite offers a private full-bath along with his-and-hers closets. Three additional bedrooms provide ample space for family, guests, or hobbies. Hardwood floors run throughout the home, enhancing its warmth and classic appeal. Completing the property is an attached two-car garage and a private setting that offers both tranquility and convenience. This charming Colonial is the perfect blend of traditional elegance, thoughtful updates, and comfortable living.

880 Whittemore Rd, Middlebury

$675,000

4 Beds ⋅ 3 Baths ⋅ 24191383 MLS

Well-maintained, single-owner Center Hall Colonial located on a corner lot in an established neighborhood. This 4-bedroom, 2.5-bath home offers a functional floor plan, a 2-car garage and central air. The main level features a formal living room and dining room, an updated eat-in kitchen with new granite counters, tile backsplash, new stainless steel appliances, and a slider to the deck. The kitchen opens to the family room with a fireplace, creating a comfortable gathering space. A half bath completes the first floor. Upstairs you'll find 4 bedrooms, including a primary suite with two walk-in closets and a full bath with a corner tub. The second-floor laundry adds everyday convenience. The unfinished walk-out basement offers excellent storage and future expansion potential. Outside, enjoy the deck, patio, and private backyard. Conveniently located in the award-winning Region 15 school district and close to parks, schools, the library, shopping, restaurants, and major commuter routes. A move-in ready home in a sought-after neighborhood.

10 Curtis Rd, Middlebury

$520,000

3 Beds ⋅ 2 Baths ⋅ 24191194 MLS

Experience the beauty of waterfront living in this charming 3-bedroom, 2-bath Cape Cod-style home nestled along Long Meadow Pond. Combining timeless character with thoughtful updates, this inviting home offers the perfect balance of comfort, convenience, and year-round recreation. Inside, you'll find warm and welcoming living spaces highlighted by a cozy fireplace-perfect for relaxing on cool New England evenings. The functional floor plan offers three comfortable bedrooms, two full bathrooms, and abundant natural light throughout. Recent improvements provide peace of mind and added value, including a new roof, new sewer connection, and a spacious new deck overlooking the water. Step outside to enjoy stunning pond views, entertain guests on the deck, or head down to your private dock for kayaking, fishing, paddleboarding, or simply taking in the tranquil surroundings. Whether you're looking for a full-time residence or a peaceful weekend escape, this waterfront gem offers a rare opportunity to enjoy the natural beauty of Long Meadow Pond while remaining just minutes from shopping, restaurants, parks, and major commuter routes.

326 Lake Shore Dr, Middlebury

$575,000

3 Beds ⋅ 3 Baths ⋅ 24190906 MLS

Tucked into Middlebury's desirable Three Mile Hill neighborhood, this beautifully maintained split-level blends everyday comfort with tasteful, modern updates throughout. A welcoming foyer opens to an expansive, light-filled living room anchored by one of the home's two floor-to-ceiling fireplaces - a warm focal point for gatherings large and small. Just off the living space, the generous eat-in kitchen showcases updated stainless steel appliances and flows through sliding glass doors to a spacious back deck, an effortless setting for morning coffee, summer grilling, or weekend entertaining. Upstairs, two well-proportioned bedrooms provide a quiet retreat, served by two full baths newly remodeled with a clean, contemporary finish. The primary is located on its own level and provides all the area you ever wished for. Additional highlights include the convenience of city water and city sewer, recessed lighting throughout, and thoughtful updates that make this home genuinely move-in ready. All of this in one of Middlebury's most established neighborhoods, with quick access to Route 64 and I-84 for an easy commute toward Waterbury, Southbury, and beyond, plus shopping, dining, and everyday amenities close at hand. A rare opportunity to own a turnkey home in a location that truly delivers. Schedule your private showing today. Porch is now painted black.

2 Northwood Dr, Middlebury

$549,900

3 Beds ⋅ 3 Baths ⋅ 24189888 MLS

Rare Stand-Alone Home in Desirable Steeplechase Complex. Experience the perfect combination of elegance, privacy and convenience in this exceptional stand alone residence in one of Middlebury's most sought after communities. Boasting nearly 2,200 square feet, this spacious home features 3 generously sized bedrooms upstairs, 2.5 baths, and an inviting open concept floor plan designed for both everyday living and entertaining. The bright living and dining area showcase soaring ceilings, beautiful hardwood floors, and an abundance of natural light. The comfortable family room is centered around a cozy gas fireplace and opens directly to a relaxing screened in porch-perfect for enjoying your morning coffee or unwinding at the end of the day. The spacious eat-in kitchen is all white and offers ample cabinet storage, newer countertops & backsplash and tile flooring. It's nice! Additional features include a 2 car garage, a full unfinished basement with lots of space , natural gas heat, city water & sewer. Also, enjoy peace of mind with a newer roof & furnace. Conveniently located near I84 and Rte 8 for easy access and commuting. Enjoy everything this turnkey home has to offer located in a quiet, walkable community.

4 Kimberwick Ct Unit 4, Middlebury

$549,900

3 Beds ⋅ 3 Baths ⋅ 24188488 MLS ⋅ Steeplechase BLDG.

4 Kimberwick Ct Unit 4, Middlebury

$515,000

4 Beds ⋅ 3 Baths ⋅ 24188724 MLS

Welcome to this meticulously maintained and exceptional 4-bedroom, 2.5-bathroom Colonial that perfectly blends classic comfort with wonderful living space. Step inside to find a warm, welcoming interior defined by beautiful hardwood flooring. The main floor features a cozy living room anchored by a traditional wood-burning fireplace, creating the perfect focal point for quiet evenings, as well as two comfortable bedrooms and a full bathroom. Upstairs, you will find two more generously sized bedrooms and a second full bathroom, offering a highly functional layout for family or guests. The lower level expands your options significantly, boasting a spacious family room equipped with a wood-burning stove to keep the space warm and inviting. Step outside to find a fantastic, large backyard featuring a level lawn and a handy storage shed to keep tools organized. Tucked away in a peaceful Middlebury neighborhood, this home offers an exceptional location where you are just minutes away from local outdoor recreation at the Middlebury Greenway and Meadowview Park, as well as convenient neighborhood dining, shopping, and everyday amenities right down the road. This beautiful, turnkey property is ready for you to move right in and make it your own!

213 Acme Dr, Middlebury

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