Middlebury Real Estate

Middlebury, CT Homes for Sale

Middlebury, CT is a Litchfield County town of roughly 7,500 residents where single-family homes typically list between $350,000 and $750,000. Dave Jones Realty tracks the local market closely, from colonial homes near Middlebury Center to larger properties around Lake Quassapaug. Middlebury sits about 12 minutes from downtown Waterbury and offers Interstate 84 access for commuters heading toward Danbury or Hartford. Buyers here favor established neighborhoods, wooded lots, and access to Region 15 schools serving Middlebury and Southbury.

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Home Styles and Price Context

Middlebury's housing stock centers on colonial and cape cod homes built between 1950 and 1990, with prices generally ranging from $350,000 to $550,000. Larger colonials and custom homes on wooded acre-plus lots list between $600,000 and $900,000. Lot sizes across Middlebury commonly run from half an acre to two acres, reflecting the town's low-density zoning. Newer construction and updated homes near Lake Quassapaug frequently exceed $750,000.

Neighborhoods

Middlebury Center

Middlebury Center anchors the town along Route 64, near the Middlebury Public Library and Town Hall. Colonial and cape homes in Middlebury Center typically list between $375,000 and $525,000 and sit close to Memorial Middle School and Long Meadow Elementary.

Lake Quassapaug Area

Homes around Lake Quassapaug in Middlebury include both year-round residences and updated lake-access properties. Prices in the Lake Quassapaug area commonly range from $500,000 to $900,000, with the largest lots exceeding two acres.

Daily Life

Middlebury residents reach Interstate 84 in under ten minutes, connecting to Waterbury in roughly 12 minutes and Danbury in about 35 minutes. Quassy Amusement Park sits on the shore of Lake Quassapaug and operates seasonally through the summer. Region 15 serves Middlebury students through Pomperaug High School in neighboring Southbury. Larkin State Park Trail runs through Middlebury for hiking and horseback riding.

Working With a Local Agent

Dave Jones Realty has represented buyers and sellers throughout Middlebury Center and the Lake Quassapaug area, offering direct market comparisons between established colonials and larger custom properties.

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Newest Homes for Sale in Middlebury, CT

$399,000
24162191 MLS
Exceptional opportunity to acquire a 1.5-acre industrial development parcel located along the highly visible Southford Road corridor in Middlebury. Situated within the IG-40 (Gateway Industrial Design District), this property is ideally suited for flex industrial, contractor headquarters, light manufacturing, or office-warehouse development. The site benefits from access to public water and public sewer, a significant advantage that reduces development costs and increases allowable building density compared to typical septic-dependent parcels in the region. Positioned just minutes from Interstate 84, the property offers convenient regional access to Waterbury, Danbury, and the greater western Connecticut market. Existing Site allows for placement of a 2-story building consisting of 6850 S.F. per floor [13,750 S.F. total with 55 Parking Spaces. Due diligence required regarding changes to underlying zone

1140 Southford Rd, Middlebury
$350,000
3 Beds ⋅ 2 Baths ⋅ 24203915 MLS
This charming 3-bedroom, 2-full-bath home offers 1,466 square feet of comfortable living space on nearly half an acre, tucked away in a peaceful neighborhood in one of Connecticut's most sought-after communities. Step inside to a welcoming living room featuring hardwood flooring and a generous 6'x3' walk-in closet. The main-level primary bedroom offers the same warmth of hardwood flooring, along with an impressive 6'x5' walk-in closet. A full bathroom with a convenient shower stall is also included on the main level. The eat-in kitchen features hardwood flooring and recessed lighting and flows naturally into a spacious family room designed for relaxing and entertaining. Here, an impressive stone fireplace creates a warm focal point, while brand-new carpeting and two skylights add comfort and natural light. Just beyond the family room, enjoy two covered outdoor spaces-an expansive 19'x16' covered patio on one side and a 17'x7' covered patio on the other-providing plenty of room for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The second level offers two additional bedrooms, each featuring hardwood flooring, along with another full bathroom enhanced by a skylight that brings in wonderful natural light. A full walk-out basement provides excellent additional space and flexibility, with a newer water heater already in place. This home offers charm, functionality, generous living spaces, and an opportunity to make it your own in beautiful Middlebury!

138 Steinmann Ave, Middlebury
$349,900
3 Beds ⋅ 2 Baths ⋅ 24196102 MLS
Nestled on a quiet, picturesque street in one of Middlebury's classic New England neighborhoods, this warm and inviting Cape Cod offers a rare opportunity to own a move-in ready home in this highly sought-after community, at an exceptional price point. Built in 1982, this charming home features 3 bedrooms, 2 full baths, and 1,469 square feet of comfortable living space filled with bright, sunlit rooms and timeless character. Major improvements provide peace of mind, including a brand-new roof and brand-new central air conditioning, both completed in 2026. Heating system is serviced on a yearly basis. Set back from the road where it's quiet and private, You'll enjoy plenty of front yard space for gardening, safe play or entertaining, while in back you'll have the expansive deck in a private setting. The spacious, dry walk-out basement offers outstanding storage and endless possibilities for hobbies, a workshop, or future expansion, while generous closet and attic storage add to the home's functionality. This home is clean, welcoming, and full of potential. While it could benefit from cosmetic updates and is being sold in as-is condition, it presents an outstanding opportunity to build equity and make it your own. Located in desirable Middlebury, you'll enjoy the town's renowned New England charm, scenic beauty, and highly acclaimed Region 15 School District. If you've been waiting for an affordable opportunity to call Middlebury home, this is one you won't want to miss!

24 Yale Ave, Middlebury
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