Middlebury, CT Homes for Sale under $600,000

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

Lauren Cavallo Lauren Ashley Homes LLC

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,

Justin Cabral West View Properties, LLC

Welcome to 24 Steinmann Avenue, where charm, thoughtful updates, and exceptional outdoor living come together in one of Middlebury's most desirable locations. This inviting Cape offers a flexible layout that lives larger than expected. The renovated kitchen features butcher block countertops, updated appliances, hardwood floors, recessed lighting, a breakfast bar, and a GE Kitchen Hub, flowing

Michael Mastronardi Keller Williams Realty

Welcome to this charming Cape Cod home, situated on a 0.34-acre corner lot in the highly desirable town of Middlebury. This home offers 1,855 square feet of comfortable living space with 4 bedrooms and 2.5 baths. The heart of the home features updated oversized country kitchen, with cabinets galore, stainless steel refrigerator, dishwaher and microwave and a gas range. Formal Living Room and

Deb Smolley Dave Jones Realty, LLC

Welcome to this charming four-bedroom traditional Colonial, privately tucked away on a secluded lot while offering the convenience of city water and 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

Christina Zainc BHGRE Gaetano Marra Homes

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

Heidi Lester KW Legacy Partners

Charming Cape on Over 5 Acres in Middlebury Discover the perfect blend of character, comfort, and country living in this enchanting Cape-style home set on more than 5 picturesque acres in Middlebury. Rich with original charm, the home features beautiful hardwood floors throughout, 3 bedrooms, and 1.5 baths. Outside, the property truly shines. Equestrian enthusiasts will appreciate the horse

Arben Belica William Raveis Real Estate

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

David Scolpino Nationwide Homes

Welcome to 57 Mistywood Lane. This home is located on a cul de sac which is private and quiet. It's like your own private oasis. The back yard is a wild life haven. The wildlife is phenomenal! Half of the property is in Naugatuck and half is in Middlebury. This spacious contemporary boasts four bedrooms and two and a half baths. There are nearby hiking and horseback trails. Hop Brook State Park

Carolyn Butkevich Regency Real Estate, LLC

Tucked away on a quiet cul-de-sac, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of comfort, functionality, and entertaining space. The inviting layout offers an open concept lower level and features a primary suite complete with a walk-in closet and private ensuite bath. The finished basement adds exceptional versatility with an additional bedroom and full bath making it ideal

Madison Ouellet K. Fortuna Realty