Middle Quarter Homes for Sale

Welcome to Middle Quarter, a hidden gem nestled in the picturesque town of Woodbury, Connecticut. This charming neighborhood, located in Litchfield County, seamlessly blends the tranquility of rural living with the conveniences of modern life. With its lush landscapes, historic architecture, and a tight-knit community, Middle Quarter is the perfect place for families, retirees, and anyone seeking a serene lifestyle.

As you stroll through the tree-lined streets, you'll be captivated by the unique character of each home. From classic New England colonials to contemporary designs, the properties in Middle Quarter boast an array of styles that cater to diverse tastes. With homes for sale that range in size and price, you’re sure to find the perfect fit for your needs. Many residences feature spacious yards, ideal for outdoor gatherings, gardening, or simply enjoying the beauty of nature.

The neighborhood is not only about stunning homes; it offers a rich tapestry of local amenities. Residents can enjoy nearby parks, boutique shops, and delightful dining options that highlight the best of Woodbury’s charm. The community is also known for its excellent schools, making it a desirable area for families.

Whether you're looking to settle down or invest in a vacation home, Middle Quarter presents an inviting opportunity. Explore the homes for sale today and discover the lifestyle that awaits you in this enchanting neighborhood. Embrace the warmth of community and the beauty of Connecticut living—Middle Quarter is ready to welcome you home!

Newest Middle Quarter Homes for Sale

$999,900

3 Beds ⋅ 3 Baths ⋅ 24146826 MLS

Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury!

27 Middle Quarter Rd, Woodbury

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.