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.

Be the First to Know About New Middlebury Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Middlebury Real Estate Map Search

Search by Lifestyle
Search by Price
Search by Bedrooms
Search by Bathrooms

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.

  Advanced Search   Market Reports   Home Value   Connect

Newest Homes for Sale in Middlebury, CT

$2,850,000
8 Beds ⋅ 8 Baths ⋅ 24151632 MLS
Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the house and related garden cottages, grounds and surrounding landscapes of fields and woodlands, drape across the gentle hilltops of Middlebury with magnificent vistas east, west and north. It constitutes one of the most beautiful and historically significant properties in the area. The estate encompasses the seventeen room main house and three guest cottages: converted stables with unique industrial accents, classic cape, and pool side studio. The main home features magnificently scaled formal and informal settings, exquisite millwork, hardwood floors. Chefs' quality kitchen with sensational marble, large butler's pantry, breakfast nook, informal dining room, 800 bottle temperature controlled wine room complete this area. This opens to the library and raised paneled great room with vaulted ceilings and stone fireplace. Pass by the sweeping free-standing staircase which leads to the second level and enter the formal dining room and living room both with fireplaces adjacent to a mahogany paneled office. The wonderful conservatory overlooking the beautiful gardens, sauna room, two half baths

775 South St, Middlebury
$2,195,000
3 Beds ⋅ 3 Baths ⋅ 24169624 MLS
Tucked along Big Cove on Lake Quassapaug, this custom architect designed Arts & Crafts bungalow is privately set on 14.85 serene acres with a path to your own cove frontage. Thoughtfully designed with the current owner's many updates and improvements and timeless materials, the home features a living room with a stone fireplace crafted from the property, a well-appointed kitchen with Custom Point cabinetry, honed granite, Wolf and Bosch appliances, and a Sub-Zero refrigerator, all opening to terraces, gardens, and a conservatory. The main-level primary suite offers two walk-in closets, a full bath, and terrace access. Upstairs includes a family room, office nook, two bedrooms, and full bath. Additional highlights include quarter-sawn white oak floors, 9' ceilings, radiant heat (kitchen, conservatory, baths), a walk-out lower-level heated recreation space, wine room and gym, plus Viessmann mechanicals and Unico A/C (5 zones). Outbuildings include two garages --one heated and cooled with epoxy floors, an equipment barn with greenhouse, and potting and wood sheds. Gated drive, magnificent stone outdoor fireplace and shower, electric awnings, and buried cistern irrigation complete this turnkey offering. Rarely does a property balance artistry, privacy, and livability so gracefully. This is a place to slow down, to gather, and to stay.

397 White Deer Rock Rd, Middlebury
$1,399,900
4 Beds ⋅ 4 Baths ⋅ 24200152 MLS
This custom-built classic brick colonial sits in one of Middlebury's most desirable neighborhoods. A private drive leads to a circular driveway with Belgian block accents, welcoming you into a gracious foyer with a sweeping staircase, on the left a formal living room and on the right a beautiful dining room-both ideal for entertaining. The two-story great room with a fireplace opens to a spacious kitchen featuring custom wood cabinetry, a breakfast bar, and a dining area. Off the kitchen, an all-season sunporch offers the perfect spot for morning coffee or evening drinks. The main floor primary suite includes a bath with a stall shower, jetted tub, and ample cabinet space, along with a walk-in closet and exercise room. Upstairs, you'll find a charming library, a second fireplace, an additional office, a loft and three more bedrooms-one ensuite and two sharing a bath. Outside, enjoy a new raised patio with a hot tub, surrounded by vibrant perennial flowers and bushes. Walking distance to beautiful Lake Quassapaug, minutes to restaurants and shops. 90 min to NYC.

67 Abbott Farms Rd, Middlebury
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.