Before you enter this charming oversized cape, take a look beyond the covered deck at 2.5 parklike acres that just happen to sit adjacent to 19 acres of Middlebury Land Trust. Imagine yourself relaxing there ... and then enter the house. The kitchen was remodeled with white cabinets, matching appliances, and Corian countertops that have a drainboard scored into the top by the sink, and a metal trivet next to the stove that allows you to put hot pots & pans on the counter without damaging it. Between the dining and living rooms is a fireplace with a propane insert to supplement the hot water baseboard heat. Mini splits provide a/c as well as an additional heat source for the first floor. The town card says 4 bedrooms, but a small room on the main level, currently used as a laundry room offers many options to fit your needs. The first floor includes a primary with a walk-in closet, and full bath with a jetted tub/shower, plus a 2nd bedroom currently used as a music room. Upstairs, 2 huge bedrooms with built-ins, large closets, & storage in the eaves are separated by a generously sized landing for max privacy, and share the 2nd full bath with its updated Fiberglass surround tub/shower and a skylight that provides natural light no matter the time of day. A full basement provides access to the 2 car garage, and lots of storage. Schedule your showing and come fall in love with this well loved and well maintained home in Middlebury.
Nestled on 1.22 acres of park-like grounds, this 2,734 sq ft contemporary offers the 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.
Welcome to this impressive 3,512-square-foot Colonial offering 10 spacious rooms 4 bedrooms 3.5 baths and a 2 car attached garage. Thoughtfully maintained and updated this home features newer mechanicals installed in 2023 including a furnace and water heater. Large deck for convenient outdoor grilling The elegant interior showcases hardwood flooring throughout crown molding and chair rail detailing throughout much of the main level The formal dining room is enhanced by a beautiful tray ceiling and leading off to a serving bar while the stunning kitchen features granite countertops, a center island tile backsplash and abundant cabinetry making it ideal for both everyday living and entertaining The inviting family room offers a soaring vaulted ceiling and a cozy gas fireplace creating a warm and welcoming gathering space The luxurious primary suite includes a spacious sitting room or dressing area that could easily be converted into an expansive walk-in closet. The en-suite bath features a Jacuzzi tub, dual vanities, private water closet and a separate glass-enclosed shower. Three additional bedrooms are located on the second floor, including two connected by a convenient Jack-and-Jill bathroom. The home also offers a main level laundry and mudroom Basement features additional cabinetry and excellent storage The large unfinished 1,795-square-foot basement with 8-foot ceilings presents endless possibilities for future expansion recreation space city water/sewer, and 2 car garage
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.
This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates throughout. Set on 1.25 meticulously landscaped acres, this 5-bedroom, 3-bath home offers warmth, space, and versatility. Built-in equity is an added bonus, with a recent appraisal valuing the home at $715,000. The stunning grounds feature mature plantings, classic New England stone walls, and inviting patio spaces that create a private outdoor retreat ideal for relaxing or entertaining. Easily accessed from the kitchen, the outdoor living areas offer seamless flow for gatherings, dining, and enjoying the peaceful setting. Inside, the updated eat-in kitchen features a fireplace with pellet stove insert, while the formal living room offers a second fireplace and the bright sunroom provides flexible living space. A separate outbuilding/studio expands the possibilities-perfect for an artist, home office, workshop, guest space, or easily converted into a detached in-law setup. Extensive updates include newer windows, updated plumbing, replaced well pump and pressure tank, newer oil tank, furnace burner replacement, exterior painting, new appliances, renovated studio/office, and a full first-floor bath. The main level has been updated with sheetrock replacing original plaster walls and ceilings, while the upper level retains its original plaster craftsmanship and antique character. A rare opportunity to own historic beauty, modern function, and value-without historic district restrictions.
Charming Cape on Over 5 Acres in Middlebury Discover the perfect blend of character, comfort, and country living in this enchanting Cape-style home set on more than 5 picturesque acres in Middlebury. Rich with original charm, the home features beautiful hardwood floors throughout, 3 bedrooms, and 1.5 baths. Outside, the property truly shines. Equestrian enthusiasts will appreciate the horse stable with a dedicated tack room, while the in-ground pool creates a private retreat ideal for relaxing and entertaining all summer long. A whole-house generator provides added convenience and peace of mind year-round. Offering exceptional space, unique amenities, and endless possibilities, this rare property presents a wonderful opportunity to own a special piece of Middlebury countryside.
SUBJECT TO PROBATE APPROVAL, AS-IS, WHERE-IS CONDITION NO FHA, CHFA OR VA LENDING AVAILABLE. NEEDS WORK. LOTS OF HARDWOOD FLOORS, DETACHED 2 CAR GARAGE WORKSHOP AND STORAGE LOFT. LARGE ROOMS, SHARED DRIVEWAY,
Nestled in the highly sought-after North Farm neighborhood, this exceptional 4BR, 3.5 bath Colonial is beautifully situated on 2.34 private acres offering the perfect blend of classic charm and comfortable living. A generous entry foyer welcomes you into a thoughtfully designed home featuring a formal living room with fireplace, elegant formal dining room and a spacious eat-in kitchen complete with pantry and breakfast bar. The inviting family room is the heart of the home, showcasing vaulted ceilings, exposed wood beams, wide plank hardwood floors and a dramatic floor-to ceiling fireplace. A dedicated study/office with built-in bookcases and a versatile bonus room provide flexible space for today's lifestyle needs. Outdoor living is equally impressive with double decks overlooking an expansive pool and serene backyard, ideal for entertaining and relaxing all summer long. This is a rare opportunity to own a beautiful property in one of the area's most desirable neighborhoods.
Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewood community of Middlebury. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of elegance, comfort, and low-maintenance living across 4 finished levels, including a sun-filled walk-out lower level. From the moment you step inside, you'll appreciate the gleaming hardwood floors, natural light throughout, spacious layout, and updated kitchen featuring granite countertops, stainless steel appliances, and ample space for entertaining. The spacious primary suite offers a peaceful retreat, while the additional finished spaces provide incredible flexibility for a family room, home office, gym, playroom, or guest area. Step outside to your private deck and patio surrounded by peaceful wooded views - perfect for relaxing or entertaining. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, and fitness center, all within minutes of shopping, dining, and major commuter routes. Move-in ready and located in one of Middlebury's most sought-after communities, this is a rare opportunity you won't want to miss.
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.
The home you have been waiting for is waiting for you at 90 Fenn Road, Middlebury. Need room for inlaws? teens? an office? You can have it right here, tucked on 1.67 acres in a desirable Middlebury location. As you enter the spacious tiled foyer and look around, a formal sunken living room greets you on one side and a formal dining room on the other. You will notice the oak flooring in both rooms. You can then make your wy to the oversized kitchen with separate dining area, featuring updated quartz counters and newer appliances. The kitchen is open to the family room and on cool nights you can enjoy the fireplace from both rooms. Upstairs the four bedrooms and two full baths create comfortable living quarters. In addition, an unfinished 21'x22 over the office is a fabulous opportunity for the new owner to add more space to this already spacious home. There is more than enough storage area provided by the walk up attic and the full basement that offers an overhead garage door for easy access. The current owner had converted the former 600 sq. ft garage as a dentist office after acquiring a certificate of zoning compliance.
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.
A private hilltop retreat at the end of a quiet cul-de-sac, this stunning 8-room contemporary is set well back from the road on a picturesque knoll, offering exceptional privacy and a peaceful natural setting. Custom built and proudly maintained by its original owner, the home features soaring ceilings, expansive rooms, and walls of windows that flood the interior with natural light. The open, airy design creates an inviting atmosphere perfect for both everyday living and entertaining. Step outside onto the brand-new deck overlooking the beautifully private surroundings-an ideal setting for relaxing, dining, or hosting gatherings. A circular driveway and attached 3-car garage add to the home's impressive presence and convenience. Distinctive architecture, privacy, and space come together to create a truly special property.
Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the house and related garden cottages, grounds and surrounding landscapes of fields and woodlands, drape across the gentle hilltops of Middlebury with magnificent vistas east, west and north. It constitutes one of the most beautiful and historically significant properties in the area. The estate encompasses the seventeen room main house and three guest cottages: converted stables with unique industrial accents, classic cape, and pool side studio. The main home features magnificently scaled formal and informal settings, exquisite millwork, hardwood floors. Chefs' quality kitchen with sensational marble, large butler's pantry, breakfast nook, informal dining room, 800 bottle temperature controlled wine room complete this area. This opens to the library and raised paneled great room with vaulted ceilings and stone fireplace. Pass by the sweeping free-standing staircase which leads to the second level and enter the formal dining room and living room both with fireplaces adjacent to a mahogany paneled office. The wonderful conservatory overlooking the beautiful gardens, sauna room, two half baths
Elegant cape with refined main-level living in Middlebury. Timeless charm and thoughtful design come together in this classic home that lives beautifully like a ranch with expanded main level. The main level offers a spacious primary bedroom with a full bath and walk-in shower, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the home features a large living room, formal dining room, and an updated kitchen with a butler's pantry. Also on the main level is a sunroom that is an inviting year-round heated with electric, living space. A well-appointed mudroom with laundry sits just off the attached 2 car garage and the kitchen, adding function without sacrificing style. Throughout the home, classic architectural details shine, including custom built-in curios and bookshelves, hardwood floors, and two fireplaces that enhance the home's warmth and character. Four bedrooms in all and set on 1.7 acres with a level yard in a sought-after Middlebury location, abuts Middlebury Land Trust's Crest Rd. Preserve. Recent improvements include a new roof in 2025. Ideally situated close to dining, parks, library, town amenities, private school, and commuter routes, this home presents a rare blend of quality craftsmanship, location, and lifestyle. Middlebury residents can also join the Middlebury Recreation Association annually for a small fee and have access to a beach on Lake Quassapaug and a pavilion at the park.
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is ready to move in to!! This home is a 2400+ sq ft 4 bedroom colonial. Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.
Middlebury is located in Connecticut. Middlebury, Connecticut has a population of 7,617. Middlebury is more family-centric than the surrounding county with 37.06% of the households containing married families with children. The county average for households married with children is 26.84%.
The median household income in Middlebury, Connecticut is $124,619. The median household income for the surrounding county is $75,043 compared to the national median of $69,021. The median age of people living in Middlebury is 46.2 years.
The average high temperature in July is 83.8 degrees, with an average low temperature in January of 15.2 degrees. The average rainfall is approximately 51.9 inches per year, with 37.8 inches of snow per year.
