Middlebury Homes for Sale

Welcome to Middlebury, Connecticut—a charming town nestled in the heart of New Haven County, where picturesque landscapes meet a vibrant community spirit. Known for its rolling hills, lush greenery, and serene lakes, Middlebury offers an idyllic setting for those seeking a peaceful retreat while still being conveniently located near urban amenities.

Middlebury is rich in history and culture, boasting a variety of recreational activities and local attractions. The town is home to beautiful parks, including the scenic Lake Quassapaug, perfect for fishing, boating, and picnicking. Residents can also enjoy the extensive hiking and biking trails that weave through the area, making it a haven for outdoor enthusiasts. With a strong sense of community, Middlebury hosts numerous events throughout the year, from farmers' markets to seasonal festivals, ensuring there's always something to enjoy.

For those considering a move to this charming town, Middlebury offers an array of homes for sale that cater to various lifestyles and preferences. Whether you're looking for a cozy single-family home, a spacious colonial, or a modern townhouse, you'll find properties that embody both comfort and style. Many homes are situated on generous lots, providing ample space for outdoor activities and gatherings. The local real estate market is thriving, making it an excellent time to invest in your dream home in Middlebury.

With its friendly atmosphere, excellent schools, and convenient access to neighboring cities, Middlebury is not just a place to live—it's a place to call home. Explore the homes for sale today and discover the possibilities that await you in this delightful Connecticut town!

Newest Middlebury Homes for Sale

$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

$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

$599,900

3 Beds ⋅ 3 Baths ⋅ 24203901 MLS

Welcome to 58 Shadduck Road, a renovated Colonial in one of Middlebury's most desirable locations. This move-in-ready home seamlessly blends timeless charm with modern updates, featuring gleaming hardwood floors and a bright open-concept layout. The main level offers a spacious living room with sliders to a large patio, a dining room, a sun-filled kitchen with center island, and a versatile office or sitting area. The second-floor primary suite serves as a private retreat with a luxurious en-suite bath and walk-in closet. Two additional bedrooms and a full bath complete the upper level. Extensive improvements include a newer roof, windows, siding, driveway, electrical, plumbing, central air, propane heating, generator-ready setup, and updated mechanicals. The full basement provides abundant storage. A rare highlight is the detached 3-car garage, offering endless possibilities for car enthusiasts, hobbyists, or additional living space. With its generous footprint and utilities, it presents an excellent opportunity for a future in-law suite, guest quarters, home office, or workshop. A newer storage shed provides additional space. Situated on a picturesque, level lot bordered by mature trees and a charming brook, the property features a private patio perfect for entertaining. Conveniently located just minutes from Middlebury's town center, shopping, restaurants, major highways, and Routes 8 and I-84, this exceptional home combines privacy, flexibility, and convenience.

58 Shadduck Rd, Middlebury

$819,000

4 Beds ⋅ 3 Baths ⋅ 24203733 MLS

Welcome to Hunting Ridge Estates! This stunning 2,700 sq. ft. Colonial, built in 2025 and just 14 months young, is located in a desirable 23-home Middlebury subdivision. Offering the ease and feel of new construction, this 4-bedroom, 4-bath home features an open floor plan and hardwood flooring throughout both levels. The bright, stylish kitchen showcases white shaker cabinetry, off-white quartz countertops, stainless steel appliances, a large center island, and walk-in pantry. It opens to the dining area and spacious family room with gas fireplace and sliders to the 17' x 15' rear patio. A formal dining room and flexible main-level bedroom/half bath add versatility. Upstairs, the spacious primary suite is a true retreat, featuring a beautifully finished ensuite with dual quartz-topped vanities, elegant oval sinks, and a 4' x 5' glass-enclosed walk-in shower. The suite includes two walk-in closets, highlighted by an impressive 12' x 14' dream closet/changing room-perfect for anyone who has always wanted exceptional wardrobe space. An upper-level laundry closet and additional full bath with double vanity, granite, tile flooring, and glass-enclosed tub/shower complete the second floor. Enjoy all that Middlebury and the surrounding area have to offer, from parks, trails, recreation, dining, and shopping to convenient access to neighboring communities. Beautifully designed, thoughtfully finished, and ideally situated, this is a home designed for modern living and enjoying life

18 Hunting Ridge Rd, 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

$999,000

4 Beds ⋅ 4 Baths ⋅ 24203121 MLS

Exceptional opportunity to build a brand-new Colonial-style home at 135 Washington Drive in desirable Middlebury. This proposed 3,485 sq. ft. residence is thoughtfully designed to feature 10 rooms, 4 bedrooms, 3 full baths and 1 half bath, a dedicated home office, fireplace, and 2-car garage, all situated on a beautiful 0.92-acre lot. Home to be built upon buyer contract, offering the opportunity to personalize select finishes and features in consultation with the builder. Final details and specifications subject to approved plans and buyer selections.

135 Washington Dr, Middlebury

$675,000

4 Beds ⋅ 4 Baths ⋅ 24202816 MLS

Welcome to this fabulous one-owner custom-built Cape Cod offering 4 bedrooms, 3.5 baths, and exceptional living space throughout. Beautiful tile and hardwood floors, vaulted ceilings, and a spacious great room with a fireplace and pellet stove create a warm and inviting atmosphere. The first-floor primary suite features a private ensuite bath, while the second floor offers two additional bedrooms, a full bath, and a huge bonus room with endless possibilities for a home office, recreation room, or additional living space. The finished lower level includes an in-law setup with a walkout, providing excellent flexibility for extended family, guests, or additional living space. Enjoy beautiful views across to Long Meadow Pond from the covered rear deck off the great room, or relax and entertain on the expansive patio area. A three-car garage provides plenty of room for vehicles, storage, and hobbies. Additional features include a whole-house propane generator and newer roofs on both the house and shed, installed in 2023. Ideally located in a great setting, this meticulously maintained custom home offers comfort, space, versatility, and beautiful views-truly a special property you'll want to see!

46 Washington Dr, Middlebury

$600,000

3 Beds ⋅ 3 Baths ⋅ 24202542 MLS

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

$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

$829,900

3 Beds ⋅ 3 Baths ⋅ 24200862 MLS

Welcome to Avalon Farms community. This home is located in Middlebury's most desirable and beautifully maintained subdivision, which is known for its unique Cotswold inspired architecture and beautifully preserved and manicured settings. This turnkey home has been so lovingly cared for. There is nothing you need to do but make this space yours. Everything feels fresh and new! Walk in the door and feel instantly relaxed by the neutral colors carefully chosen throughout the home which showcase all the many updates this home provides with beautifully maintained hardwood floors throughout the first floor. The convenience of having a first-floor primary suite with so many added touches, such as tray ceiling, 2 spacious walk-in closets, and a beautifully updated master bath with towel warmers complete this bedroom oasis. The kitchen truly serves as the heart of the home, featuring an oversized center island with granite countertops that complement the updated Jenn Air stainless steel appliances. This kitchen is an entertainer's dream for everything from casual mornings to hosting holidays with family and friends. First floor laundry adds everyday convenience, while soaring cathedral ceilings create an open, airy feeling throughout the living room. Step outside to the expansive 18x30 mahogany rear deck where privacy and serenity await as you enjoy views of Avalon Farm Pond from afar throughout much of the year.

29 Cambridge Ct, Middlebury

$1,399,900

4 Beds ⋅ 4 Baths ⋅ 24200152 MLS

This custom-built classic brick colonial sits in one of Middlebury's most desirable neighborhoods. A private drive leads to a circular driveway with Belgian block accents, welcoming you into a gracious foyer with a sweeping staircase, on the left a formal living room and on the right a beautiful dining room-both ideal for entertaining. The two-story great room with a fireplace opens to a spacious kitchen featuring custom wood cabinetry, a breakfast bar, and a dining area. Off the kitchen, an all-season sunporch offers the perfect spot for morning coffee or evening drinks. The main floor primary suite includes a bath with a stall shower, jetted tub, and ample cabinet space, along with a walk-in closet and exercise room. Upstairs, you'll find a charming library, a second fireplace, an additional office, a loft and three more bedrooms-one ensuite and two sharing a bath. Outside, enjoy a new raised patio with a hot tub, surrounded by vibrant perennial flowers and bushes. Walking distance to beautiful Lake Quassapaug, minutes to restaurants and shops. 90 min to NYC.

67 Abbott Farms Rd, 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

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