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$590,000
4 Beds 3 Baths 24184437 MLS
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, 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

700 Watertown Rd, Middlebury

$649,900
4 Beds 4 Baths 24178550 MLS
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.

168 N Farm Rd, Middlebury

$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

$660,000
4 Beds 4 Baths 24167501 MLS
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.

90 Fenn Rd, Middlebury

$585,000
4 Beds 4 Baths 24164662 MLS
Circa 1803 "Todt Farm," is a historically significant center hall Colonial set on 1.06 picturesque acres overlooking and adjacent to Fenn Pond. This 11-room home offers 2,691 sq ft with 4 bedrooms and 3.1 baths. Rich with authentic vintage details including wide board floors, 7 fireplaces, horizontal board paneling, built-ins, and classic 12-over-12 windows and front and rear stairwells. The charming sunroom opens to a stone patio, ideal for enjoying the serene setting of mature trees, gardens, stone walls and rolling and level lawns. The property is surrounded by Middlebury Land Trust land, including the preserved Brookdale farm across the street. Additional features include an attached 2-bay garage and a 20kW Generac generator.Pool is being sold "as-is." Middlebury offers an extensive variety of outdoor enjoyment such as the Middlebury Rec Area, Quassy Amusement Park, Lake Quassapaug, the 4.5 paved Greenway walking trail, Meadowview Park and the John Largay Preserve. Come take a look!

66 Artillery Rd, Middlebury

$724,900
4 Beds 4 Baths 24161366 MLS
Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting dinner parties. The entertaining continues into a well-lit living room and a separate, cozy family room-offering plenty of space for everyone to relax. Upstairs, you'll find the home's private sleeping quarters, featuring three bedrooms and two full bathrooms. Need more room? Then travel downstairs to a highly versatile area that can function as additional bedrooms, a dedicated office space, or even a perfect in-law suite thanks to an additional full bathroom. The partially finished basement is an entertainer's dream, complete with a dedicated media room and storage galore. The unfinished portion offers even more practicality, serving as a workshop for tools and crafts, along with abundant extra storage. Step outside to your private yard, a true outdoor oasis! The landscaped pool area is an entertainer's delight, offering the perfect backdrop for summer barbecues and weekend relaxation. With plenty of parking, hosting friends and family is always a breeze. This distinctive property truly is a must-see!

80 Pine Hollow Dr, Middlebury

$2,850,000
8 Beds 8 Baths 24151632 MLS
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

775 South St, Middlebury

$750,000
4 Beds 3 Baths 24147892 MLS
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.

117 Crest Rd, Middlebury

$599,900
4 Beds 4 Baths 24146182 MLS
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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