Refine Search
Sort by
$2,195,000
3 Beds 3 Baths 24169624 MLS
Tucked along Big Cove on Lake Quassapaug, this custom architect designed Arts & Crafts bungalow is privately set on 14.85 serene acres with a path to your own cove frontage. Thoughtfully designed with the current owner's many updates and improvements and timeless materials, the home features a living room with a stone fireplace crafted from the property, a well-appointed kitchen with Custom Point cabinetry, honed granite, Wolf and Bosch appliances, and a Sub-Zero refrigerator, all opening to terraces, gardens, and a conservatory. The main-level primary suite offers two walk-in closets, a full bath, and terrace access. Upstairs includes a family room, office nook, two bedrooms, and full bath. Additional highlights include quarter-sawn white oak floors, 9' ceilings, radiant heat (kitchen, conservatory, baths), a walk-out lower-level heated recreation space, wine room and gym, plus Viessmann mechanicals and Unico A/C (5 zones). Outbuildings include two garages --one heated and cooled with epoxy floors, an equipment barn with greenhouse, and potting and wood sheds. Gated drive, magnificent stone outdoor fireplace and shower, electric awnings, and buried cistern irrigation complete this turnkey offering. Rarely does a property balance artistry, privacy, and livability so gracefully. This is a place to slow down, to gather, and to stay.

397 White Deer Rock Rd, Middlebury

$879,900
3 Beds 4 Baths 24184419 MLS
Located in one of Middlebury's most desirable and beautifully maintained subdivisions Avalon Farms with streetlights and Belgian block lined streets, this impressive 3 bedroom, 3 full and 1 half bath Colonial offers 3,494 square feet of refined and flexible living. Set on a premium, fully usable flat lot surrounded by mature pines for year round privacy, the home features Hardie Plank siding and extensive stone veneer. A grand two story foyer opens to a spacious, light filled interior designed for comfortable main level living. The first floor primary suite offers an oversized closet and spa like bath, complemented by main level laundry, pantry, eat in kitchen, great room, large study with its own fireplace, and attached garage. The soaring great room features a second fireplace and an inviting gathering space. The kitchen includes a Bertazzoni gas cooktop, new under counter ZLINE microwave, new refrigerator, new dishwasher, double oven, and updated hardware. Upstairs are two generous bedrooms with full bath access and a spacious loft that could easily serve as a fourth bedroom, office, or additional living area. Updates include refinished hardwood floors, fresh interior paint, updated hardware, select new lighting, and many more chic updates. A paver patio, established gardens, landscape lighting, central vacuum, generator plug, EV charging capability, and unfinished lower level, ready for you to finish for additional living space, complete this exceptional home.

25 Avalon 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

$649,900
3 Beds 3 Baths 24185515 MLS
MAKE OFFER! Nestled on 1.22 acres of park-like grounds, this large custom designed home offers privacy & serenity you've been searching for, lovingly maintained by its original owners. Step inside and be greeted by a sunken, front-to-back living room anchored by a fireplace, setting the tone for the thoughtful design found throughout. Entertain in style in the formal dining room with elegant French doors or gather in the huge family room- another fireplace and generous proportions make it the heart of the home. The eat-in kitchen features a breakfast bar, perfect for casual mornings. Three bedrooms, 2.5 baths, and 3 fireplaces offer the comfort and warmth your family deserves. And, when you want to escape, a finished mancave with wet bar is all yours. Outside, a 54-foot deck provides the ultimate backdrop for outdoor entertaining, overlooking your own private retreat. Three oversized garages and newly paved driveway add convenience and curb appeal alike. Oh, and by the way, please do not forget to walk up a couple of steps behind the deck to a beautiful level lot adjacent to a tree lined area. Perfect for incorporating your very own fire pit or gazebo, for further relaxation and enjoyment. Peace of mind comes built-in with recent updates including a new whole-house generator (1 yr), deck (3 yrs), electric hot water heater (3 yrs), paved driveway (2 yr), and a 15-year roof. Located in the New England town of Middlebury, known for its small-town character and top-rated schools.

70 Pine Hollow Dr, Middlebury

$600,000
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

$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

$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

$575,000
3 Beds 3 Baths 24190906 MLS
Tucked into Middlebury's desirable Three Mile Hill neighborhood, this beautifully maintained split-level blends everyday comfort with tasteful, modern updates throughout. A welcoming foyer opens to an expansive, light-filled living room anchored by one of the home's two floor-to-ceiling fireplaces - a warm focal point for gatherings large and small. Just off the living space, the generous eat-in kitchen showcases updated stainless steel appliances and flows through sliding glass doors to a spacious back deck, an effortless setting for morning coffee, summer grilling, or weekend entertaining. Upstairs, two well-proportioned bedrooms provide a quiet retreat, served by two full baths newly remodeled with a clean, contemporary finish. The primary is located on its own level and provides all the area you ever wished for. Additional highlights include the convenience of city water and city sewer, recessed lighting throughout, and thoughtful updates that make this home genuinely move-in ready. All of this in one of Middlebury's most established neighborhoods, with quick access to Route 64 and I-84 for an easy commute toward Waterbury, Southbury, and beyond, plus shopping, dining, and everyday amenities close at hand. A rare opportunity to own a turnkey home in a location that truly delivers. Schedule your private showing today. Porch is now painted black.

2 Northwood Dr, Middlebury

$539,000
3 Beds 3 Baths 24191913 MLS
Step into this beautifully maintained 3-bedroom, 2.5-bath split-level home where comfort and functionality come together. Gleaming hardwood floors extend throughout the entire home. The living room features a cozy fireplace, creating the perfect space to relax. The bright kitchen opens seamlessly into the dining room, making everyday living and entertaining a breeze. From the kitchen, step out onto the backyard deck overlooking the spacious backyard-ideal for summer barbecues, morning coffee, or simply enjoying the outdoors. The finished lower level offers valuable additional living space and features a walkout to a beautiful patio, providing even more room for entertaining, a family room, home office, or recreation area. With expansive front and back yards, this home offers plenty of outdoor space for gardening, play, or relaxing. Thoughtfully designed with inviting indoor and outdoor living spaces, this home is ready for its next chapter.

123 Northwood Dr, Middlebury

$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
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

$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

$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

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.