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

$415,000
3 Beds ⋅ 2 Baths ⋅ 24071697 MLS
Price Improvement!! DIRECT WATER FRONT PROPERTY with water access and rights just waiting for new owners right in time for Spring! This 3 bed, 2 full bath recently remodeled home boasts custom cabinets, granite counters & island with a breakfast bar, stainless steel appliances, custom built-ins and views of the private Long Meadow Pond. Hiking trails abound with Larkin State Park as your backdrop which sweeps around the pond abutting the cul-de-sac street the home sits on. The top floor has a small office or bedroom and generous sized Primary Suite, walk-in closet, full bath and sliders leading to a TREX terrace with SOARING views. The 2nd floor is an open concept living/dining/kitchen with side entrance, sliders leading to another Trex Deck with a large pantry. Another FULL Bathroom w/ tub finish out the level. The third floor houses the 3rd bedroom or family room/playroom, a dedicated laundry room and utility closet with door to yet ANOTHER TREX deck and walkway to an oversized double landing wood deck and planting beds leading to the cleared land down to the water. Detached garage, wired electric with a workshop and lower room for an in-law or extra living space. Minutes to Southbury/Middlebury Hamlet or Naugatuck for shopping & entertaining yet feels worlds away from civilization. Bring your fishing boat, canoe, kayak for years of summer memories and evenings relaxing on your VERY OWN PRIVATE BEACH with TWO fire p

460 Lake Shore Dr, Middlebury
$410,000
3 Beds ⋅ 2 Baths ⋅ 24069534 MLS
Charming 1920's 3 bedroom, 2 bath Cape nestled in a desirable Middlebury neighborhood. This home boasts modern mechanical updates, including split systems air conditioning for year-round comfort. Hardwood floors flow throughout the inviting living space. Outdoors, you'll find beautifully maintained perennial gardens and a private patio, perfect for relaxation or entertaining. Conveniently located near walking path and popular restaurants, this property combines character, comfort and an unbeatable location. HIGHEST AND BEST BY Monday 2/3 at 5 pm!

197 White Ave, Middlebury
$410,000
2 Beds ⋅ 1 Baths ⋅ 24062344 MLS ⋅ Tyler's Cove Association,Inc. BLDG.
Set among the trees offering a tranquil, waterfront setting! Single family condo at Tyler's Cove. Galley kitchen with an abundance of cabinets. Enjoy your morning coffee in this lovely dining room with wall of windows affording you natural light and scenic views of the lake! Cozy living room with French doors to dining room. 2 bedrooms & bathroom. All on main level with hardwood flooring thru-out! Open second level with expansion possibilities! Brand new, cedar impressions vinyl shakes! Private dock. Boating, kayaking, swimming and more for year round fun! Low Annual HOA fees of $800.

81 Sandy Beach 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.