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

$4,050,000
6 Beds ⋅ 4 Baths ⋅ 24131596 MLS
SUPERB LAKE PROPERTY. First time on the market, this 4,811 sf shingle-style home on 6.99 acres in Lake Quassapaug's estate area offers 195 feet of direct waterfront with a private dock and small beach. Designed by renowned architect Rick Moisan and built in 2000, the residence blends timeless design with modern comfort, enjoying complete privacy and pastoral views of permanently protected neighboring hayfields and vineyards. This rare offering combines architectural pedigree, serene natural beauty, and versatile living spaces-a true sanctuary for lakefront living. TWO PARCELS. Includes the main residence and a charming two-bedroom cottage sold together. MAIN RESIDENCE. Classic shingle-style architecture with a bright, open layout for today's lifestyle. The living room, dining area, and kitchen flow together beautifully; the kitchen features high-end appliances and opens to an inviting sunroom capturing passive solar warmth. Every room enjoys a full or partial landscape view. A deep covered porch spans the lake side for gracious entertaining, sunsets, and al fresco dining. Large Doric columns frame the space, and a majestic oak anchors the open lawn. COTTAGE. Originally the caretaker's residence for historic Tranquillity Farm, this two-bedroom, 1,005 sf cottage on a separate parcel offers wonderful flexibility as a guesthouse, writer's retreat, or rental.

7-11 Sandy Beach Rd, Middlebury
$1,750,000
5 Beds ⋅ 7 Baths ⋅ 170507932 MLS
Exquisite Country Cape situated along one of Middlebury's most picturesque roads. This 5800 sq.ft. Cape is a true gem, boasting a gunite pool, acres of open meadow bounded by stone walls, distant city views & beautiful backyard w/ patio, perfect for hosting summer soirees. Recently renovated, this sprawling home offers a fabulous eat-in kitchen w/ spacious island and a generous dining area featuring a vaulted ceiling w/ exposed hand-hewn beams & FP. A cased opening leads to a sun porch with 3 walls of glass offering seamless access to a private patio.The main level is a showcase of elegance & functionality featuring a formal LR w/ FP & built-ins, a gracious DR w/ corner built-ins, a paneled 1st floor office complete w/ FP & wet bar & a sumptuous primary BR suite. Almost every room treats you to breathtaking distant views of the patio & inviting in-ground pool. The upper level offers a quaint loft area & 3 beautifully appointed BR’s, two of which have en suite baths, resulting in a total of 3 full baths on this floor. The pristine exterior boasts the hallmark Middlebury stone walls adorning the front, fencing, terraced patios, in-ground pool, practice golf range for enthusiasts & acres of lush meadow for your enjoyment. Additional amenities include a 2nd first-floor BR suite, an attached 3 car garage & a drive-under garage that provides multi-car storage space in the basement. Situated in the highly sought-after South Street location, this property is an exceptional find.

700 South St, Middlebury
$1,750,000
4 Beds ⋅ 7 Baths ⋅ 24020405 MLS
Stunning all brick home w/ heated in-ground pool, covered outdoor dining/entertaining space and main level master set on a private lot on a cul-de-sac of similar homes. In-ground pool w/ spa, fully applianced and covered outdoor kitchen w/ entertaining area, bar, fireplace and ample room for sitting. Poolhouse. Putting greens. Gorgeous patio w/ pergula. Inside, remodeled eat-in-kitchen w/ granite countertops, large center island, Stainless Steel appliances including 6 burner Wolf stove, Subzero fridge, wine fridge, potfiller, pantry and 2 sinks. Family room w/ fireplace open to kitchen area. 2-story formal living room w/ applianced wetbar and fireplace. Grand dining room. Study w/ rich wood paneling and ceiling. Main level master suite w/ fireplace, trey ceiling, walk-in closet w/ built-ins, and attached full bath w/ marble floor, tile surround shower, double sink and jetted tub. Main level laundry room w/ granite. 2 main level powder rooms. 3 additional bedrooms upstairs all with an attached bath and ample closet space. Bonus room upstairs. Tastefully finished lower level with gorgeous trimwork and fireplace, wine room, home gym, and potential for even more finished space. High ceilings and beautiful trimwork throughout. Mechanicals include central air, propane heat, audio, generator, sec system, central vac. New roof and many very recent updates. The facade, curb appeal and entertaining area are absolutely striking. Don't miss the chance to have your own private estate!

40 Winthrop Dr, 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.