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.

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All Recently Sold in Middlebury, CT

$610,000
3 Beds 3 Baths 24004579 MLS
What a versatile and charming home to spend quality time with friends and family! Set in a quiet cul de sac neighborhood this home offers the opportunity for outdoor activities like walking or riding bikes without traffic concerns. It sits on a half of an acre of flat 100% useable yard with a fenced in back yard and a beautiful stone patio. The large front yard is great for outdoor games like soccer or football. Step inside to discover a warm, welcoming, and modernized interior. The main-level family room is bathed in natural light, providing ample space for various seating arrangements. The eat-in kitchen and separate dining room cater to both casual and formal dining needs. With two primary bedrooms, homeowners have the option of choosing between the convenience of the main level, or the seclusion of the second floor. Both primary bedrooms are spacious with updated en-suite bathrooms. While the basement remains unfinished, it offers a bright and clean space ideal for storage or the realization of a finished area, should a buyer want more living space. Additional features such as access to public water and sewer, central air conditioning, and propane heating further enhance the appeal of this home. Conveniently located just five minutes away from shopping and dining options, and a mere 10-minute drive from I84, this home offers a highly desirable blend of accessibility and tranquility. Embrace the lifestyle you've been longing for and make this your new home this spring!

40 Dorothy Dr, Middlebury

$610,000
3 Beds 4 Baths 24059462 MLS
Benson Woods is the perfect place for active adults seeking a serene and carefree lifestyle. The blend of condo and single-family living offers the best of both worlds. This home, offered by the original owner, boasts many custom features and a premium location that is both private and convenient. The open floor plan with hardwood floors throughout creates a warm and inviting atmosphere. The living room and dining room combination, with a vaulted ceiling and gas fireplace, offers flexible furniture placement options. The eat-in kitchen is a chef's delight, featuring a large center island, custom pantry, cherry cabinets, granite countertops, and a roomy dining area. The primary suite is a luxurious retreat with a large walk-in shower, double closets, and a custom bath cabinet. The main floor also includes a second bedroom, another full bath, and a laundry room. The second floor provides additional space for guests, grandchildren, or working from home, with a third bedroom, an office or den, a loft, and another full bath. The finished basement is a versatile space, complete with a half bath, kitchen, media room, living room, and workshop. The two-car attached garage adds to the convenience and functionality of this beautiful home. Living in Benson Woods means enjoying the beauty of nature, the convenience of nearby shopping and dining, and the comfort of a well-maintained community. The perfect place to call home!

107 Periwinkle Dr Unit 107, Middlebury

$610,000
3 Beds 4 Baths 24002272 MLS Ridgewood At Middlebury BLDG.
CHOICE LOCATION WITH GORGEOUS VIEWS! This home was one of the first ones to be built by Ginsburg Development and it was built with quality, care and craftsmanship. Desirable Dickinson style home with an open floor plan and just a quick walk to the pool and clubhouse. This lovely home features an open floor plan. Living room has a gas fireplace with a custom mantel, hardwood floors and leads to a very large deck overlooking lush gardens and breathtaking views. The kitchen is sunny and bright and has a custom bay window with custom window treatments. There is a classy ceiling above the dining area for an elegant look. Primary bedroom is on the first floor with a large walkin closet with California type closet organizer and drawers. Primary bath has dual sink,a separate shower, walk in tub and separate toilet. The second floor features a loft, perfect for reading room, or game room. There are 2 large bedrooms on the second floor with ample closet space and a shared full bath. The lower level is fully finished off with gorgeous, custom wood paneling and custom trim. There is a family room with builtins and sliders to a patio, a sitting area, full bath and beautiful wood paneled office with recess lighting, wet bar, builtins and French Doors. Lower level is perfect for an inlaw or guests. Ridgewood a desirable community with a wonderful clubhouse for movies, basketball, friendly gatherings, pool and exercise room. Easy commute to NYC (90mins) and excellent schools and restaurants

14 Dogwood Court, Unit 14, Middlebury

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