Middlebury Condos for Sale

Middlebury Condos for Sale

Welcome to Middlebury, Connecticut, a hidden gem nestled in New Haven County that perfectly blends suburban charm with natural beauty. Known for its picturesque landscapes, this quaint town is characterized by its rolling hills, serene lakes, and lush green spaces, making it an ideal place for families and nature enthusiasts alike. With a rich history dating back to the 18th century, Middlebury boasts a tight-knit community and a welcoming atmosphere, where neighbors become friends and local events bring everyone together.

Middlebury is conveniently located, offering easy access to major highways and the vibrant cities of Waterbury and New Haven. Residents enjoy a peaceful lifestyle while being just a short drive away from urban amenities, shopping, dining, and cultural attractions. The town is also home to excellent schools and recreational facilities, ensuring a high quality of life for all its residents.

For those looking to make Middlebury their home, the market for condos for sale is thriving. These modern and stylish condominiums provide the perfect balance of comfort and convenience, often featuring open floor plans, contemporary finishes, and community amenities such as pools and fitness centers. Whether you're a first-time buyer, downsizing, or seeking a second home, Middlebury's condos offer a fantastic opportunity to enjoy a low-maintenance lifestyle in a beautiful setting.

Explore the charm of Middlebury today and discover your dream condo in this delightful Connecticut town, where every day feels like a retreat!

Newest Middlebury Condos for Sale

203 Sugar Maple Way Unit 203, Middlebury
$589,900
2 Beds ⋅ 3 Baths ⋅ 24213697 MLS ⋅ Benson Woods BLDG.
Experience maintenance-free living at its finest in Benson Woods, a premier 55+ community in Middlebury. This townhome features an open, main-level layout highlighted by a sun-drenched great room with soaring ceilings, hardwood floors, and a natural gas fireplace. The eat-in kitchen comes well-appointed with rich wood cabinetry, granite countertops, and stainless steel appliances. Retreat to the main-floor primary suite, complete with tray ceiling, dual walk-in closets, and a spa-like bath featuring dual sinks, makeup vanity, and a walk-in shower. A versatile den, half bath, laundry room, and access to the attached two-car garage complete the main level. Upstairs, a spacious loft with a private balcony overlooks the great room, alongside a second bedroom, huge closet, and full bath. The expansive, unfinished basement offers ample ceiling height, natural light, yard-access walk up hatch, active radon mitigation system, and rough-in plumbing for a future bathroom. This unit was completed in 2013.

203 Sugar Maple Way Unit 203, Middlebury
104 Periwinkle Dr Unit 104, Middlebury
$530,000
2 Beds ⋅ 3 Baths ⋅ 24214764 MLS ⋅ Benson Woods BLDG.
Welcome to Benson Woods, a desirable 55+ community! This beautiful freestanding Hopkins Model offers spacious rooms, soaring ceilings, and stylish features throughout. The spacious kitchen is a standout, featuring rich wood cabinetry, stainless steel appliances, abundant counter space, and an oversized center island with seating-perfect for casual dining and entertaining. The kitchen opens to the impressive Living and Dining Room, where soaring ceilings and beautiful hardwood floors create a bright, airy atmosphere. The first-floor primary suite offers two walk-in closets and a private bath with a double-sink vanity, large walk-in shower, and generous soaking tub. A second bedroom, convenient half bath, and laundry room complete the main level, providing comfortable one-floor living. Upstairs, a sun-filled loft overlooks the Living and Dining Room below. A second full bath and separate bonus room offer flexible space for a home office, hobby room, or guests. Additional highlights include hardwood floors in the Living Room, Dining Room, and hallway, a gas range, and a gas hookup on the back deck for convenient grilling-no propane tanks needed! With its inviting layout, spacious kitchen, and versatile living spaces, this lovely Hopkins Model offers the perfect opportunity to enjoy comfortable, low-maintenance living in Benson Woods. Come see all this wonderful home has to offer!

104 Periwinkle Dr Unit 104, Middlebury
16 Caveson Court, Unit 16, Middlebury
$575,000
3 Beds ⋅ 3 Baths ⋅ 24191400 MLS ⋅ Steeplechase BLDG.
Welcome to this beautifully updated three-bedroom Cape in the desirable Steeplechase community. Hardwood flooring flows throughout the home, complemented by custom plantation shutters and window treatments in most rooms. The flexible floor plan includes an additional room off the eat-in kitchen. Upstairs, you'll find three spacious bedrooms, two updated baths, and conveniently located laundry. The primary suite features two walk-in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

16 Caveson Court, Unit 16, Middlebury
35 Nutmeg Rd Unit B2, Middlebury
$219,900
1 Beds ⋅ 1 Baths ⋅ 24202228 MLS ⋅ Middlebury Commons BLDG.
BEST DEAL IN MIDDLEBURY! Motivated seller! 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. Den could be used as second bedroom. New deck. central air. heat pump furnace. Clubhouse on property. Conveniently located close to town center.

35 Nutmeg Rd Unit B2, Middlebury
3 Brookside Dr Unit 3, Middlebury
$599,900
4 Beds ⋅ 4 Baths ⋅ 24145711 MLS ⋅ Brookside Of Middlebury BLDG.
Discover refined comfort and timeless elegance in this beautifully appointed Cheshire model, nestled within the highly sought-after Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home is truly move-in ready. Open-concept floor plan that instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the main living areas-perfect for hosting family and friends. First-floor primary suite, complete with a luxurious jacuzzi tub and two spacious walk-in closets. Through elegant glass French doors, you'll find a dream dressing room or home office, outfitted with a PAX wardrobe system, dressing table, and desk. The dramatic two-story foyer leads to the upper level, offering three additional bedrooms and a full bath, all overlooking the stunning two-story living room with a cozy fireplace. The finished walk-out basement expands your living space with endless possibilities-ideal for a home office, gym, media room, or game area. An additional 600+ sq ft of storage with a tool bench provides ample space for hobbies and organization. Enjoy peaceful mornings or relaxing evenings on the expansive deck, taking in tranquil views of the lush, protected preserve. This is more than just a house-it's a place to be a truly home. AS IS SALE (INSPECTIONS ARE INFOMATIONAL PURPOSES ONLY )

3 Brookside Dr Unit 3, Middlebury
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