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$774,900
3 Beds ⋅ 2 Baths ⋅ 24160275 MLS
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 20 Hunting Ridge Road (aka Lot 11) is to be built. It is one level living at its finest! Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office in addition to 3 bedrooms and a 2 car attached garage. The primary bedroom boasts walk-in closet with custom shelving and private full bath. There are several other lots and plans to choose from or will build to suit! City water and sewer. Pictures are of previous house built.

20 Hunting Ridge Rd, Middlebury
$520,000
3 Beds ⋅ 2 Baths ⋅ 24191194 MLS
Experience the beauty of waterfront living in this charming 3-bedroom, 2-bath Cape Cod-style home nestled along Long Meadow Pond. Combining timeless character with thoughtful updates, this inviting home offers the perfect balance of comfort, convenience, and year-round recreation. Inside, you'll find warm and welcoming living spaces highlighted by a cozy fireplace-perfect for relaxing on cool New England evenings. The functional floor plan offers three comfortable bedrooms, two full bathrooms, and abundant natural light throughout. Recent improvements provide peace of mind and added value, including a new roof, new sewer connection, and a spacious new deck overlooking the water. Step outside to enjoy stunning pond views, entertain guests on the deck, or head down to your private dock for kayaking, fishing, paddleboarding, or simply taking in the tranquil surroundings. Whether you're looking for a full-time residence or a peaceful weekend escape, this waterfront gem offers a rare opportunity to enjoy the natural beauty of Long Meadow Pond while remaining just minutes from shopping, restaurants, parks, and major commuter routes.

326 Lake Shore Dr, Middlebury
$499,900
3 Beds ⋅ 2 Baths ⋅ 24195720 MLS
Welcome home to this beautifully updated property located in one of Middlebury's quiet and sought after neighborhoods. This move in ready home features a stylish kitchen with granite countertops, a gas range, and smart appliances, including a refrigerator, washer and dryer. Gleaming hardwood floors in living room, hallway and bedrooms. Enjoy year-round comfort with central air conditioning and peace of mind with a generator hookup and included generator. Fresh paint throughout and a completely renovated lower level provide modern, versatile living space. Step outside to a low-maintenance Trex deck and almost a half acre yard, perfect for relaxing or entertaining. Conveniently located near schools, parks, walking trails, and major highways, with local vineyards, fine dining, and all that Middlebury has to offer just minutes away.

112 Joy Rd, Middlebury
$499,000
3 Beds ⋅ 2 Baths ⋅ 24193863 MLS
Completely renovated and thoughtfully designed, this stunning 3-bedroom Cape offers modern style, quality craftsmanship, and a glimpse of lake views. The open floor plan is perfect for today's lifestyle, featuring newly refinished hardwood floors, detailed custom woodwork, wood ceilings, and a spacious living area that flows seamlessly into the beautifully updated kitchen. The kitchen is a cook's dream, showcasing a large center island, stylish finishes, and two sliding doors that open to an expansive wraparound slate patio, creating the ideal indoor/outdoor entertaining space. The flexible floor plan includes a bonus room that can serve as a formal dining room, home office, or cozy den. The spacious primary suite overlooks the professionally landscaped backyard and features a large walk-in closet with a custom California Closet organization system. Renovated bathrooms, propane heat, central air, a tankless hot water heater, and a high efficiency furnace provide comfort and efficiency. The home is also whole house generator ready for added peace of mind. The finished lower level offers additional living space with a fireplace, perfect for a family room, game room, or home gym. Outside, enjoy a beautifully landscaped yard, a one car garage, a large storage shed, and the added value of an included extra lot, providing exceptional outdoor space and privacy.

251 Lake Shore Dr, Middlebury
$479,900
4 Beds ⋅ 2 Baths ⋅ 24200006 MLS
Welcome Home to this nicely updated New England Cape style home with a comfortable and convenient layout. This move-in ready home offers 4 bedrooms and 2 full bathrooms. An inviting living room showcases a fireplace creating a warm and cozy gathering space for the whole family, adjoining dining area leads to The large kitchen includes ample workspace, lots of cabinets and tile flooring, with easy access to the large deck, and back yard-perfect for all your outdoor entertaining. Two bedrooms, and recently renovated full bath and hardwood floors complete the main level. As you walk upstairs you will find a Full remodeled bathroom, A bedroom and A large primary bedroom, with vaulted ceilings, slider to balcony overlooking your landscaped back yard, A large closet, hardwood floors and fresh paint finish out this fabulous space. Added bonuses include full walk out basement into one car garage, ample storage, large shed and parking for the whole family. Don't miss out on the chance to make this move-in ready home yours! It is close to Route 84 and Middlebury walking trail. Welcome to Middlebury and their award- winning region 15 school.

106 Steinmann Ave, Middlebury
$474,500
2 Beds ⋅ 2 Baths ⋅ 24194436 MLS
Cottage Colonial close to town center, parks and more in beautiful Middlebury CT! This 1929 build charmer has stunning details both inside and out. Lovingly cared for, the pride of ownership of this property is evident upon arrival. Note the unique features including: Hardwood flooring throughout main and upper levels, sunken family room w/wood panel vaulted ceiling and slider to deck, wood burning fireplace in the Parlor/Living room. Kitchen boasts granite countertops, stainless appliances (newer Dishwasher & Range) and breakfast bar. Stunning Dining room with corner built ins reminiscent of bygone days offers a special gathering spot. Combo Laundry/Powder room and Office also on main level. Upstairs there are 2 good sized bedrooms with hall bath. Then a surprise 3rd level finished room w/electric heat. Ideal extra space to enjoy (play room, music room, reading room, you choose!). Step outside to enjoy the lovely wraparound deck with Pergola and Garage/Shed for lawn equipment, tools or even a possible gardening shed! Generator hook-up in place. City water and sewer too. Book your appt. and see this gem of a home for yourself soon!

47 Middlebury Ter, Middlebury
$350,000
3 Beds ⋅ 2 Baths ⋅ 24203915 MLS
This charming 3-bedroom, 2-full-bath home offers 1,466 square feet of comfortable living space on nearly half an acre, tucked away in a peaceful neighborhood in one of Connecticut's most sought-after communities. Step inside to a welcoming living room featuring hardwood flooring and a generous 6'x3' walk-in closet. The main-level primary bedroom offers the same warmth of hardwood flooring, along with an impressive 6'x5' walk-in closet. A full bathroom with a convenient shower stall is also included on the main level. The eat-in kitchen features hardwood flooring and recessed lighting and flows naturally into a spacious family room designed for relaxing and entertaining. Here, an impressive stone fireplace creates a warm focal point, while brand-new carpeting and two skylights add comfort and natural light. Just beyond the family room, enjoy two covered outdoor spaces-an expansive 19'x16' covered patio on one side and a 17'x7' covered patio on the other-providing plenty of room for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The second level offers two additional bedrooms, each featuring hardwood flooring, along with another full bathroom enhanced by a skylight that brings in wonderful natural light. A full walk-out basement provides excellent additional space and flexibility, with a newer water heater already in place. This home offers charm, functionality, generous living spaces, and an opportunity to make it your own in beautiful Middlebury!

138 Steinmann Ave, Middlebury
$349,900
3 Beds ⋅ 2 Baths ⋅ 24196102 MLS
Nestled on a quiet, picturesque street in one of Middlebury's classic New England neighborhoods, this warm and inviting Cape Cod offers a rare opportunity to own a move-in ready home in this highly sought-after community, at an exceptional price point. Built in 1982, this charming home features 3 bedrooms, 2 full baths, and 1,469 square feet of comfortable living space filled with bright, sunlit rooms and timeless character. Major improvements provide peace of mind, including a brand-new roof and brand-new central air conditioning, both completed in 2026. Heating system is serviced on a yearly basis. Set back from the road where it's quiet and private, You'll enjoy plenty of front yard space for gardening, safe play or entertaining, while in back you'll have the expansive deck in a private setting. The spacious, dry walk-out basement offers outstanding storage and endless possibilities for hobbies, a workshop, or future expansion, while generous closet and attic storage add to the home's functionality. This home is clean, welcoming, and full of potential. While it could benefit from cosmetic updates and is being sold in as-is condition, it presents an outstanding opportunity to build equity and make it your own. Located in desirable Middlebury, you'll enjoy the town's renowned New England charm, scenic beauty, and highly acclaimed Region 15 School District. If you've been waiting for an affordable opportunity to call Middlebury home, this is one you won't want to miss!

24 Yale Ave, Middlebury
$324,900
2 Beds ⋅ 2 Baths ⋅ 24193924 MLS
Welcome to this Middlebury home offering the perfect blend of comfort, functionality, and a desirable location. The home's refreshed interior provides move-in-ready feel designed for everyday living. The property is an excellent opportunity for buyers looking for a home that is ready to enjoy. The home sits on a level lot and is situated directly next to a small brook.

125 Shadduck Rd, Middlebury

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