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

$750,000
4 Beds ⋅ 3 Baths ⋅ 24147892 MLS
Elegant cape with refined main-level living in Middlebury. Timeless charm and thoughtful design come together in this classic home that lives beautifully like a ranch with expanded main level. The main level offers a spacious primary bedroom with a full bath and walk-in shower, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the home features a large living room, formal dining room, and an updated kitchen with a butler's pantry. Also on the main level is a sunroom that is an inviting year-round heated with electric, living space. A well-appointed mudroom with laundry sits just off the attached 2 car garage and the kitchen, adding function without sacrificing style. Throughout the home, classic architectural details shine, including custom built-in curios and bookshelves, hardwood floors, and two fireplaces that enhance the home's warmth and character. Four bedrooms in all and set on 1.7 acres with a level yard in a sought-after Middlebury location, abuts Middlebury Land Trust's Crest Rd. Preserve. Recent improvements include a new roof in 2025. Ideally situated close to dining, parks, library, town amenities, private school, and commuter routes, this home presents a rare blend of quality craftsmanship, location, and lifestyle. Middlebury residents can also join the Middlebury Recreation Association annually for a small fee and have access to a beach on Lake Quassapaug and a pavilion at the park.

117 Crest Rd, Middlebury
$749,900
4 Beds ⋅ 4 Baths ⋅ 24193938 MLS
Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters, reading nooks, and a finished attic, while thoughtful updates include a recently painted interior, updated baths, upgraded electrical, central air, gas fireplace insert, and a chef's kitchen with quartz countertops, double ovens, and stainless-steel appliances. Picture windows overlook the private backyard oasis featuring two Bluestone patios, a Belgian block patio, and a renovated Gunite saltwater pool with waterfall, newer mechanicals, and fencing. Exterior improvements include newer siding, roof, chimney, barn-style lighting, and professional landscaping. Surrounded by protected woodlands and the sounds of nearby church bells, this one-of-a-kind home offers the perfect blend of historic character, modern updates, and peaceful New England living.

77 Crest Rd, Middlebury
$724,900
4 Beds ⋅ 4 Baths ⋅ 24161366 MLS
Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting dinner parties. The entertaining continues into a well-lit living room and a separate, cozy family room-offering plenty of space for everyone to relax. Upstairs, you'll find the home's private sleeping quarters, featuring three bedrooms and two full bathrooms. Need more room? Then travel downstairs to a highly versatile area that can function as additional bedrooms, a dedicated office space, or even a perfect in-law suite thanks to an additional full bathroom. The partially finished basement is an entertainer's dream, complete with a dedicated media room and storage galore. The unfinished portion offers even more practicality, serving as a workshop for tools and crafts, along with abundant extra storage. Step outside to your private yard, a true outdoor oasis! The landscaped pool area is an entertainer's delight, offering the perfect backdrop for summer barbecues and weekend relaxation. With plenty of parking, hosting friends and family is always a breeze. This distinctive property truly is a must-see!

80 Pine Hollow Dr, Middlebury
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