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$534,900
3 Beds ⋅ 3 Baths ⋅ 24189888 MLS
Rare Stand-Alone Home in Desirable Steeplechase Complex. Experience the perfect combination of elegance, privacy and convenience in this exceptional stand alone residence in one of Middlebury's most sought after communities. Boasting nearly 2,200 square feet, this spacious home features 3 generously sized bedrooms upstairs, 2.5 baths, and an inviting open concept floor plan designed for both everyday living and entertaining. The bright living and dining area showcase soaring ceilings, beautiful hardwood floors, and an abundance of natural light. The comfortable family room is centered around a cozy gas fireplace and opens directly to a relaxing screened in porch-perfect for enjoying your morning coffee or unwinding at the end of the day. The spacious eat-in kitchen is all white and offers ample cabinet storage, newer countertops & backsplash and tile flooring. It's nice! Additional features include a 2 car garage, a full unfinished basement with lots of space , natural gas heat, city water & sewer. Also, enjoy peace of mind with a newer roof & furnace. Conveniently located near I84 and Rte 8 for easy access and commuting. Enjoy everything this turnkey home has to offer located in a quiet, walkable community.

4 Kimberwick Ct Unit 4, Middlebury
$534,900
3 Beds ⋅ 3 Baths ⋅ 24188488 MLS ⋅ Steeplechase BLDG.
Rare Stand-Alone Home in Desirable Steeplechase Complex. Experience the perfect combination of elegance, privacy and convenience in this exceptional stand alone residence in one of Middlebury's most sought after communities. Boasting nearly 2,200 square feet, this spacious home features 3 generously sized bedrooms upstairs, 2.5 baths, and an inviting open concept floor plan designed for both everyday living and entertaining. The bright living and dining area showcase soaring ceilings, beautiful hardwood floors, and an abundance of natural light. The comfortable family room is centered around a cozy gas fireplace and opens directly to a relaxing screened in porch-perfect for enjoying your morning coffee or unwinding at the end of the day. The spacious eat-in kitchen is all white and offers ample cabinet storage, newer countertops & backsplash and tile flooring. It's nice! Additional features include a 2 car garage, a full unfinished basement with lots of space , natural gas heat, city water & sewer. Also, enjoy peace of mind with a newer roof & furnace. Conveniently located near I84 and Rte 8 for easy access and commuting. Enjoy everything this turnkey home has to offer located in a quiet, walkable community.

4 Kimberwick Ct Unit 4, Middlebury
$529,900
3 Beds ⋅ 3 Baths ⋅ 24186753 MLS ⋅ Ridgewood At Middlebury BLDG.
Welcome to 10 Ridgewood Drive in Middlebury, located in the highly sought-after Ridgewood community, offering exceptional amenities including a clubhouse, swimming pool & tennis courts. This beautifully maintained townhouse is being offered for sale by its original owner and has been extensively remodeled throughout. The main level features an open-concept floor plan designed for today's lifestyle, with gleaming hardwood floors and a convenient first-floor half bath. The updated eat-in kitchen boasts granite countertops, stainless steel appliances and direct access to a private deck perfect for relaxing or entertaining. The second floor offers 3 generously sized bedrooms and 2 full baths. The spacious primary suite features a walk-in closet, double vanity, soaking tub, and separate shower. A conveniently located second-floor laundry area with washer and dryer adds to the home's functionality. Need even more living space? The finished third-floor loft provides endless possibilities as a home office, fitness area, or guest suite. Additional features includes a 1-car garage, full basement offering abundant storage, and an efficient three-zone heating and cooling system, allowing you to maximizing energy efficiency. Ideally situated near the community clubhouse and pool, and just minutes from shopping, restaurants, walking trails and major highways, this exceptional home offers the perfect combination of comfort, style, and convenience in one of Middlebury's premier communities.

10 Ridgewood Dr Unit 10, 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
2 Beds ⋅ 1 Baths ⋅ 24203525 MLS
Rare opportunity to own direct waterfront on beautiful Lake Quassapaug! Located in the desirable Tylers Cove community, this charming two-bedroom cottage sits just 50 feet from the water and features its own private dock and yard with direct lake frontage. The cottage is ready for a new owner to bring their ideas and updates-renovate the existing home, explore the possibilities of rebuilding, or simply enjoy it as a classic summer retreat. A special opportunity to experience lakefront living, boating, swimming, and relaxing by the water on one of the area's most beautiful lakes.

89 Sandy Beach Road Unit 89, 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
$499,000
4 Beds ⋅ 3 Baths ⋅ 24188724 MLS
Welcome to this meticulously maintained and exceptional 4-bedroom, 2.5-bathroom Colonial that perfectly blends classic comfort with wonderful living space. ADDED BONUS - Solar panels that have no monthly fee and very low usage expense! Winter months around $60 month, Summer bill typically no more than $180. Annual average $1530!! Step inside to find a warm, welcoming interior defined by beautiful hardwood flooring. The main floor features a cozy living room anchored by a traditional wood-burning fireplace, creating the perfect focal point for quiet evenings, as well as two comfortable bedrooms and a full bathroom. Upstairs, you will find two more generously sized bedrooms and a second full bathroom, offering a highly functional layout for family or guests. The lower level expands your options significantly, boasting a spacious family room equipped with a wood-burning stove to keep the space warm and inviting. Step outside to find a fantastic, large backyard featuring a level lawn and a handy storage shed to keep tools organized. Tucked away in a peaceful Middlebury neighborhood, this home offers an exceptional location where you are just minutes away from local outdoor recreation at the Middlebury Greenway and Meadowview Park, as well as convenient neighborhood dining, shopping, and everyday amenities right down the road. This beautiful, turnkey property is ready for you to move right in and make it your own!

213 Acme Dr, Middlebury
$474,900
3 Beds ⋅ 3 Baths ⋅ 24200565 MLS
Move-in ready and thoughtfully renovated this 7-room, 3-bedroom, 2.5-bath home offers 1,357 sq ft of stylish living space plus an additional 480 sq ft finished walkout lower level, set on a quiet cul-de-sac. The open-concept main level features a spacious Living Room and Dining Room flowing into an expansive Eat-In Kitchen, with direct access to a large deck overlooking a private backyard-ideal for outdoor dining, entertaining, or relaxing. Three bedrooms and two fully renovated full baths complete the main level. The finished walkout lower level adds valuable flexibility with a large Family/Recreation Room, laundry room with half bath, and abundant storage. Additional highlights include Central Air Conditioning, attached 2-car garage, maintenance-free vinyl siding, and convenient access to shopping, dining, recreation, and major commuter routes. Beautifully updated and ready to enjoy, this home offers the perfect blend of comfort, functionality, and lifestyle convenience. A wonderful opportunity to make this inviting property your own and enjoy a place to call home.

133 Algin Dr, 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
$469,900
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
$449,900
3 Beds ⋅ 3 Baths ⋅ 24191937 MLS
Set on nearly half an acre in one of Middlebury's most desirable neighborhoods, this 3-bedroom, 2.5-bath Colonial blends timeless character with everyday comfort. Gleaming hardwood floors run throughout the home, anchoring an open, inviting layout built for both daily living and entertaining. The heart of the home is a spacious family room crowned by a dramatic cathedral ceiling and ceiling fan, a bright and airy retreat that flows naturally into the rest of the main level. The kitchen is ready to cook in and gather around, featuring granite countertops, a breakfast bar, and stainless appliances including a gas cooktop. Generous living and dining rooms round out the main floor, each finished in warm hardwood. Upstairs, the primary bedroom suite offers a private full bath and walk-in closet, with two additional well-sized bedrooms, one with its own walk-in closet. A cozy fireplace, central air, thermopane windows, and zoned heating add year-round comfort and efficiency. Outside, enjoy a level, open lot with plenty of room to play, garden, or relax. A full unfinished basement with garage access and a one-car under-house garage provide ample storage and expansion potential. A brand new basement system was installed on 7/14/26, adding to peace of mind.

42 White Ave, 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
$339,900
2 Beds ⋅ 1 Baths ⋅ 24113785 MLS
Picture-perfect and completely updated, this classic New England Cape delivers far more than its footprint suggests. A paver walkway, lamppost, and lush hosta gardens frame a storybook exterior with black shutters and stone front steps - genuine curb appeal on one of Middlebury's most established streets. Inside, the open floor plan connects a sun-filled living area to a fully renovated kitchen featuring a quartz-topped center island with seating, two-tone cabinetry with brass hardware, stainless appliances, and a wall of windows overlooking the green backdrop beyond. Crown molding, designer lighting, and thoughtful finishes carry throughout - every detail has been done, so you simply move in. Two bedrooms and a full bath complete this efficient, light-filled layout. Steps from the Middlebury Greenway Trail with easy Route 64 and I-84 access, and served by the award-winning Region 15 school district. A turnkey Connecticut gem.

12 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
$300,000
2 Beds ⋅ 1 Baths ⋅ 24205239 MLS
Totally renovated and completely move-in ready! This charming Cape is located in the wonderful town of Middlebury and offers a fantastic alternative to condo living-without the monthly HOA fees. Step inside to a bright, fresh interior where all the work has already been done for you. The updated kitchen features stainless steel appliances, modern finishes, and plenty of natural light. Thoughtfully renovated throughout, this home offers the perfect blend of comfort, style, and low-maintenance living. Whether you're a first-time buyer, looking to downsize, or simply searching for a beautifully updated home in a desirable community, this Middlebury gem is ready for you to move right in and enjoy!

327 Steinmann Ave, Middlebury
$224,900
1 Beds ⋅ 1 Baths ⋅ 24202228 MLS ⋅ Middlebury Commons BLDG.
Perfect Unit For active 55+ Individual close to the walking trails and a short drive to private recreation beach for swimming, kayaking or canoeing. Nestled in secluded area cul de sac this Middlebury, 55+ community is in Excellent Condition. All appliances included. Small complex. Bright and Well kept Second floor Unit. Living room dining room combo. New deck. central air. heat pump furnace. Clubhouse on property. Conveniently located close to town center.

35 Nutmeg Rd Unit B2, Middlebury

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