Welcome to this stunning, completely updated home located in one of Middlebury's highly desirable neighborhoods! Offering 3 bedrooms and 2.5 bathrooms, this exceptional property showcases high-end finishes, quality craftsmanship, and thoughtful upgrades throughout. No detail has been overlooked in creating a home that perfectly blends luxury, comfort, and modern convenience. Step inside to discover beautiful hardwood floors, custom built-in closets, and an inviting propane fireplace that adds warmth and elegance. The impressive list of improvements includes a new roof (2021), updated plumbing and HVAC systems (2021), central air conditioning (2021), and enhanced spray foam insulation for improved energy efficiency. A whole-house generator provides additional peace of mind, while smart thermostats and a security system offer modern convenience. The beautifully finished lower level takes this home to another level, featuring luxurious heated floors and a temperature-controlled wine cellar, perfect for wine enthusiasts and entertaining. Outside, enjoy professionally landscaped grounds, an elegant paver walkway, and a beautiful paver patio ideal for outdoor gatherings or quiet relaxation. Additional highlights include city water, city sewer, and a prime location offering convenient access to major highways, restaurants, local vineyards, and Middlebury's highly regarded schools. Truly move-in ready!!
Welcome to 203 North Farm Road, a retreat that perfectly captures the essence of classic New England charm blended with sophisticated luxury. Set on a sprawling, private 3.4-acre lot in one of Middlebury's most sought-after neighborhoods, this 2005-built estate offers an unparalleled sense of space and tranquility. Spanning over 4,300 square feet, the home is defined by its grand proportions and thoughtful layout. The main level is designed for both effortless entertaining and comfortable daily living, featuring exceptionally spacious rooms filled with natural light. The upper level is a rare find, boasting four generous bedrooms, each serving as a private sanctuary with its own dedicated en-suite bathroom. With a total of four full and two half baths, the home provides convenience and privacy for everyone. Outside, the expansive acreage offers a serene backdrop for outdoor enjoyment and a true escape from the everyday. This is a unique opportunity to own a stately residence in a premier location. Sale is subject to Probate Court approval.
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.
BUYERS Remorse! Don't miss out on one of Middlebury's best properties! 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. 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 with full warranty was installed on 7/14/26, adding to peace of mind.
Located on a most desirable street in North Farms neighborhood, this well loved and beautifully tended 4 bedroom colonial offers great opportunities for comfortable living and entertaining. Filled with light, this home will dazzle you with its beautiful interior. You can prep meals and enjoy them in the updated eat in kitchen with access to a deck overlooking lush grounds. The spacious family room features a fireplace and provides a peaceful retreat after a busy day. The living and dining rooms are great spaces for entertaining and enjoying special times. You can easily relax in the primary bedroom with a recently updated spa-like bathroom and 2 walk in closets. The upper level also features 3 additional bedrooms, an updated full bath as well as a laundry area. You will also enjoy bonus space on the walk out level. The lovely landscaping contributes to the calm atmosphere that surrounds this home. Rear of property adjoins Flanders Nature, further enhancing the privacy of this property.
Custom finishes throughout, down to the smart toilet, in this move-in ready 1941 Cape with original character. The kitchen has custom cabinetry, black stone counters, bamboo floors and a sunlit bay window, and original hardwood floors run through the living and dining rooms. Both full baths have black-stone finishes; the primary bath has a double vanity, warm wood, perimeter floor lighting and a waterfall/body-jet shower. Custom built-ins add storage upstairs. The finished lower level offers a second living area, office/gym space, laundry and storage. Out back, the deck opens to a large, tree-lined 0.34-acre yard. Multi-zone ductless heat and AC, with an oil boiler as backup heat. Roof approx. 10 years old. Detached garage. One-year home warranty included, extendable to three. Region 15 schools and convenient I-84 access.
For the antique lover, the one with vision and a desire to bring this fabulous home back to its original glory, this is the place for you. Set on over 2 acres within walking distance to Lake Quassapaug, this is a fabulous property. It offers a main house with approximately 1900 s.f.. You'll love the wide board floors, plaster walls and so many details that reflect a fabulous past. In addition to the main house, there is a detached, oversized 2 car garage with a workshop and a finished artist's loft. Enjoy the opportunity for gardens, more fruit trees and a lovely enclosed screened porch. So many original features. This is a spot for the artist, antique lover, the ones who appreciate history and have a desire to own a piece of history. The house is not air conditioned, but the area over the garage has a split system for heat and air conditioning.
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 to this beautifully maintained ranch, ideally situated on a quiet cul-de-sac in one of Middlebury's desirable neighborhoods. Set on a private, level 1 acre lot, this 3 bedroom, 3.5 bath home offers comfort, character, and exceptional space for everyday living and entertaining. The inviting open floor plan features a stunning sunken living room, three fireplaces, and a spacious family room. The kitchen and living spaces flow seamlessly to a screened-in porch and newly remodeled deck, creating a wonderful indoor-outdoor entertaining experience. Additional highlights include an attached 3 car garage, partially finished basement, central air, city water and sewer, oil and electric heat, and an auto-start Generac generator. This home is conveniently located minutes from shopping, grocery stores, and major highways. A special home offering privacy, space, and convenience-don't miss it!
New construction designed to impress! The Cambridge Model offers 2,878 sq. ft. of thoughtfully designed living space. A grand two-story foyer leads to the stunning great room with soaring ceilings, fireplace and beautiful windows creating a light and airy feel. The heart of the home is the spacious kitchen featuring an expansive island, granite countertops, stainless steel appliances and white shaker-style cabinetry. A breakfast nook with French doors opens to the back deck, while the formal dining room is perfect for entertaining. The first-floor primary suite offers two walk-in closets and a luxurious bath with oversized shower and double vanities. A private first-floor den provides the ideal space for a home office, homeschooling or quiet retreat. Hardwood floors run throughout the main level, which also includes laundry and a mudroom. Upstairs, two generously sized bedrooms share a Jack-and-Jill bath. Additional features include a 2-car attached garage, central air, underground utilities and sprinklers, private well and public sewer. Set on just over an acre in the desirable Avalon Farms community with limited seasonal views of the pond. Photos are of similar construction; pictured lighting is not included. Floor plans, elevations and proposed site plan are attached.
MOTIVATED SELLER - Looking for a QUIET, SECLUDED location? Welcome to 182 Green Hill Road, where space, privacy, and an exceptional Curtis Farms setting come together. Set at the end of a long private driveway on almost 3 acres, this spacious 4-bedroom, 2.5-bath Colonial offers over 3,000 square feet of living space with an incredible grand living-room with fireplace and vaulted ceiling, perfect for entertaining or relaxing with the family. The main level features hardwood flooring, generous formal living and dining areas, a private office, and a spacious eat-in kitchen with granite countertops and stainless appliances. The primary suite includes a private en-suite bath with Whirlpool tub, separate shower and double vanity. Three additional bedrooms provide plenty of room for family and guests. Enjoy the privacy of the expansive grounds from the large deck, along with a two-car garage, large unfinished basement space, generator hookup, and brand-new central air system. The rooftop solar system also offers a favorable locked-in lease rate with for transfer to the next owner. Located in one of Middlebury's most sought-after residential neighborhoods, this home offers the space and privacy of an acreage property while remaining convenient to local amenities, and surrounding communities plus the property is within the desirable Region 15 school district.
Welcome to this extraordinary 4,261-square-foot home, truly one of a kind within the complex. This 4 bedroom, 3 full baths & 2 half baths is thoughtfully designed for both elegant entertaining and comfortable everyday living. This exceptional residence offers a first-floor primary suite and an impressive open-concept layout. The luxurious primary suite is a private retreat, featuring a newly remodeled spa-inspired bathroom with beautiful fixtures & elegant, white marble throughout and a relaxing soaking tub. Dual walk-in closets with custom-built organizers provide exceptional storage and organization. For effortless entertaining, the home features a generously sized kitchen, opened to a spectacular, 2 story great room. A substantial center island creates the perfect gathering space, while an abundance of rich cherry cabinetry provides both warmth and exceptional storage. The seamless connection between the kitchen and great room makes entertaining and everyday life feel effortless. The impressive great room creates a dramatic focal point, filling the home with an abundance of natural light and offering a wonderful sense of openness yet providing warmth with the grand, stone, gas fireplace. A dedicated dining room with French doors, creating an inviting connection to the surrounding living spaces both for family and friends.
REDUCED AND PRICED FOR IMMEDIATE SALE! 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!
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. The full walk-out basement includes a brand, new boiler (2026), and a newer water heater. This home offers charm, functionality, generous living spaces, and an opportunity to make it your own in beautiful Middlebury.
Experience uncompromised interior luxury with zero yard-maintenance stress at 18 Hunting Ridge Road. Nestled in a quiet Middlebury cul-de-sac with a natural wooded privacy hill out back, this 2025-built custom Colonial trades endless weekend lawn-mowing chores for spectacular, turn-key indoor living. Step inside to a sprawling, open-concept main floor highlighted by dramatic open-beam ceilings and an abundance of natural light. The chef's kitchen is an absolute showstopper, featuring an oversized quartz island, premium finishes, and a seamless flow into the primary family room. Upstairs, the luxury primary suite serves as a true sanctuary, boasting a massive, dedicated 12' x 14' custom dressing room/changing suite that must be seen to be believed. A flexible main-level bedroom and full bath offer the perfect layout for multigenerational living, long-term guests, or a quiet executive home office. Forget spending your weekends managing sprawling acreage-the rear topography creates a magnificent, maintenance-free natural privacy barrier with absolutely no rear neighbors looking in. Enjoy quiet mornings or evening entertaining on your expansive 17' x 15' rear patio, perfectly curated for an upscale outdoor lounge experience. Equipped with public water, public sewer, and an expansive unfinished full basement ready for future expansion. Perfect for busy professionals, downsizers, or anyone seeking premium custom spaces without the upkeep of a massive lawn.
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.
Exceptional 1855 Greek Revival set in a prestigious Middlebury neighborhood, surrounded by the natural beauty of Flanders Preserve and Middlebury Land Trust land. This 5-bedroom, 31/2-bath architectural stunner is sited on 3.21 beautifully landscaped acres with mature trees, stone walls, perennial gardens and rolling open lawn, offering privacy and a feeling of escape and tranquility. The home includes wide-board floors, three fireplaces and a remarkable series of covered porches and "piazzas" capturing the romance of 19th-century country living. There is effortless flow from the gorgeous sunroom, with walls of windows, into the formal living room, dining room and large entertaining kitchen. A main-floor laundry room, enormous utility room, pantry and powder room add convenience. The primary suite offers a private retreat, with an en-suite bath and adjoining sitting room or study, flanked by two covered porches. Outside, a charming secluded wading pool with fountain provides a wonderfully relaxed setting for summer gatherings, cocktails and afternoons spent enjoying the gardens. A detached 2-car garage with bonus unfinished loft space invites a future artist studio. An exceptional opportunity to bring this distinctive home to the next level. 2 hrs to NYC. Subject to Probate.
Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters, reading nooks, and a finished attic, while thoughtful updates include a recently painted interior, updated baths, upgraded electrical, central air, gas fireplace insert, and a chef's kitchen with quartz countertops, double ovens, and stainless-steel appliances. Picture windows overlook the private backyard oasis featuring two Bluestone patios, a Belgian block patio, and a renovated Gunite saltwater pool with waterfall, newer mechanicals, and fencing. Exterior improvements include newer siding, roof, chimney, barn-style lighting, and professional landscaping. Surrounded by protected woodlands and the sounds of nearby church bells, this one-of-a-kind home offers the perfect blend of historic character, modern updates, and peaceful New England living.
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.
Pride of ownership and tasteful updates shine throughout this lovingly maintained, one-owner Colonial in the desirable Curtis Farms subdivision. Set on a corner lot in an established dead-end neighborhood, this 4-bedroom, 2.5-bath home offers a welcoming setting close to schools, parks, and major highways. The main level features formal living and dining rooms and an updated eat-in kitchen with new granite counters, a tile backsplash, and new stainless steel appliances. The kitchen opens to a comfortable family room with a fireplace, while sliding doors lead to the deck for easy outdoor dining and entertaining. A half bath completes the first floor. Upstairs, the primary suite offers two walk-in closets and a full bath with a corner tub. Three additional bedrooms and second-floor laundry provide space and everyday convenience. Central air and a 2-car garage add to the home's appeal, while the unfinished walk-out basement offers generous storage and potential for future finished space. Enjoy the deck, patio, and private backyard, along with a location in the Region 15 school district near schools, parks, the library, shopping, and restaurants. A move-in-ready home offering comfort, thoughtful updates, and convenient commuter access in sought-after Curtis Farms.
MOTIVATED SELLERS! MAKE OFFER! Nestled on 1.22 acres of park-like grounds, a large custom designed home offering privacy & serenity and 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. 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. MOTIVATED SELLERS! MAKE OFFER!
This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates. Built-in equity! Recent appraisal values this home at $715,000. Set on 1.25 meticulously landscaped acres, this 4-bedroom, 3-bath home offers warmth, space, and versatility with a huge finished attic space. 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, new well pressure tank and jet pump, newer oil tank, furnace burner replaced, 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
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 8 Deer Run Road (aka Lot 16) is just beginning construction. 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. 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.
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
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.
