Middlebury Real Estate

Recently Sold Listings in Middlebury, CT

Welcome to your dedicated resource for viewing Sold listings in Middlebury, CT. As local Middlebury, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights home values, selling strategies, and options like cash offers. Start exploring the most recent sold properties in Middlebury, CT below, or if you are looking to sell a home in Middlebury, CT contact a local agent to discuss the possibilities.

< Back to all Homes for Sale in Middlebury, CT

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
  Advanced Search   Market Reports   Home Value   Connect

All Recently Sold in Middlebury, CT

$487,400
2 Beds ⋅ 3 Baths ⋅ 24011457 MLS ⋅ Steeplechase BLDG.
Lovely 2 bedroom stand alone home features first floor bedroom, full bath and laundry access. The living room seamlessly transitions into the dining area, creating an open space perfect for gatherings. Natural light floods through the windows, creating a bright and cheerful ambiance. The nearby eat-in kitchen is spacious and well-equipped. The family room, complete with a cozy gas fireplace, offers a relaxed setting for unwinding or hosting guests. The door leading to the deck offers a relaxing spot to enjoy the outdoors. Completing the main level is a half bathroom. The upper-level bedroom provides privacy and comfort. Adjacent to it is a full bath. The loft area offers versatility, serving as a home office, study space, or even a cozy reading nook. The spacious two-car garage provides additional storage for tools and outdoor equipment. The full basement, with its walk-out access to the backyard, offers endless possibilities. Whether it's a home gym, entertainment area, workshop or craft area.

5 Kimberwick Ct Unit 5, Middlebury
$485,000
4 Beds ⋅ 3 Baths ⋅ 24185992 MLS
Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit today's evolving lifestyle. The main home features expansive living and dining spaces, a full bath, a main-level bedroom, and an additional flexible-use room ideal for a home office, den, guest space, or hobby room. Upstairs, you'll find two generously sized bedrooms with abundant closet space and a convenient half bath. A standout feature is the potential in-law setup, complete with its own living area, bedroom, and full bath, providing endless possibilities for multi-generational living, extended guests, or added privacy. Throughout the home, you'll appreciate the details that make this property truly special-from beautiful built-ins and custom trim work to the character and craftsmanship rarely found today. Outside, enjoy a spacious backyard designed for both relaxation and entertaining, featuring a large above-ground pool with surrounding deck space, perfect for summer gatherings and enjoying the outdoors. The lower level offers additional storage, garage space, and a workshop area complete with a workbench, ideal for hobbyists, craftsmen, or anyone in need of extra room. This is not your average Cape-style home. With its generous living space, unique layout, and endless possibilities, this home it ready for its next chapter!

413 Watertown Rd, Middlebury
$485,000
3 Beds ⋅ 2 Baths ⋅ 24109477 MLS
Beautiful 3-Bedroom home with first floor Primary Suite on nearly half acre lot! Welcome to your dream home! This charming 3-bedroom, 2 Full Bath residence combines modern updates with timeless character. Step inside to discover newly, refinished hardwood floors & fresh paint throughout, creating a bright & inviting space ready for you to move right in. The first-floor primary suite offer privacy & comfort, with a spacious walk-in closet. The layout is thoughtfully designed with both a formal living room & a formal dining room perfect for entertaining. Enjoy a warm & open atmosphere in the great room with sliders that open to an oversized deck-ideal for outdoor dining & relaxation. You'll also find the perfect work-from-home space in the dedicated office. C/A, city water/sewer, 1 car garage all located in a desirable neighborhood, this home offers the perfect blend of comfort, function, & style. Don't miss your chance to own this beautifully maintained home!

101 Shadduck 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.