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

$520,000
3 Beds ⋅ 3 Baths ⋅ 24085206 MLS ⋅ Ridgewood At Middlebury BLDG.
Beautiful luxury Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath built by Toll Brothers, nestled on a private cul-de-sac in unique location. Over 2,100 sqft designed modern living space, this home includes a 4-foot bump-out for added size. Entering the home, the first floor features an open floor plan w/ hardwood floors, white cabinetry, stainless steel appliances, perfect for modern living, an upgraded skylight in kitchen floods the space with natural light. Off the kitchen is a private deck with wooded views & a large living room w/ a gas fireplace. Upstairs the spacious primary suite offers a walk-in closet and a luxurious bath with a double vanity, shower, and tub. The second bedroom also includes a walk-in closet, while the third bedroom showcases custom millwork/ built-ins for both function and style for additional utility and architectural interest. Enjoy the privacy of a wooded backyard and the convenience of a walk-out basement w/ custom storage shelves and two workbenches, woodworkers dream! Right next to the home is the "Great Meadow Lawn" adding a huge yard to play games, entertain or take a scenic stroll. Very rare location, big upgrade here $$$ . Ridgewood amenities include an outdoor pool, gym, indoor basketball court, tennis courts, a movie theater, and a clubhouse lounging area-all within walking distance. Plenty of upgrades, prime location and privacy. Don't miss this resort style must-see property! Can't build for this price!

29 Winding Trail, Unit 29, Middlebury
$520,000
3 Beds ⋅ 3 Baths ⋅ 24098549 MLS
First Time on the Market - Classic 1930s Colonial in Prime In-Town Location Step into timeless elegance with this rare, stately 1930s Colonial, offered to the open market for the first time. Full of classic charm, the home features original moldings, custom built-ins, and enduring craftsmanship throughout. The main level offers a spacious front-to-back living room with a fireplace and gleaming hardwood floors, a formal dining room perfect for entertaining, a cozy eat-in kitchen, and a thoughtfully added family room providing extra space for everyday living. Upstairs, you'll find three generously sized bedrooms, two full baths, and a bright second-floor landing with additional built-ins. A walk-up attic offers abundant storage or potential future expansion. Set in a hidden gem of a neighborhood, this home sits along the historic trolley bed trail, offering direct access to local shops, restaurants, and all the amenities of in-town living.

1 Stevens Rd, Middlebury
$515,000
4 Beds ⋅ 3 Baths ⋅ 24189438 MLS
Highest and Best by Tuesday, the 21st, 5pm. Welcome to this charming four-bedroom traditional Colonial, privately tucked away on a secluded lot while offering the convenience of city sewer. This light and bright home combines timeless character with important modern updates, including a DeGiorgi roof with a transferable warranty, a new driveway, updated electrical panel, and a newer boiler. Inside, a classic center hall foyer with a graceful staircase welcomes you. The spacious eat-in kitchen is ideal for everyday living, while the formal dining room, complete with a charming swinging door, and is perfect for entertaining. The front-to-back living room features a cozy wood-burning fireplace and new sliding glass doors that open to the backyard, creating a seamless connection to outdoor living. A tucked-away office or den with built-ins provides the perfect space for working from home, reading, or relaxing. Upstairs, the generous primary suite offers a private full-bath along with his-and-hers closets. Three additional bedrooms provide ample space for family, guests, or hobbies. Hardwood floors run throughout the home, enhancing its warmth and classic appeal. Completing the property is an attached two-car garage and a private setting that offers both tranquility and convenience. This charming Colonial is the perfect blend of traditional elegance, thoughtful updates, and comfortable living.

880 Whittemore Rd, Middlebury
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