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77 Crest Rd, Middlebury
$699,900
4 Beds ⋅ 4 Baths ⋅ 24193938 MLS
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.

77 Crest Rd, Middlebury

47 Middlebury Ter, Middlebury
$474,500
2 Beds ⋅ 2 Baths ⋅ 24194436 MLS
Cottage Colonial close to town center, parks and more in beautiful Middlebury CT! This 1929 build charmer has stunning details both inside and out. Lovingly cared for, the pride of ownership of this property is evident upon arrival. Note the unique features including: Hardwood flooring throughout main and upper levels, sunken family room w/wood panel vaulted ceiling and slider to deck, wood burning fireplace in the Parlor/Living room. Kitchen boasts granite countertops, stainless appliances (newer Dishwasher & Range) and breakfast bar. Stunning Dining room with corner built ins reminiscent of bygone days offers a special gathering spot. Combo Laundry/Powder room and Office also on main level. Upstairs there are 2 good sized bedrooms with hall bath. Then a surprise 3rd level finished room w/electric heat. Ideal extra space to enjoy (play room, music room, reading room, you choose!). Step outside to enjoy the lovely wraparound deck with Pergola and Garage/Shed for lawn equipment, tools or even a possible gardening shed! Generator hook-up in place. City water and sewer too. Book your appt. and see this gem of a home for yourself soon!

47 Middlebury Ter, Middlebury

10 Curtis Rd, Middlebury
$650,000
4 Beds ⋅ 3 Baths ⋅ 24191383 MLS
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.

10 Curtis Rd, Middlebury

326 Lake Shore Dr, 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

70 Pine Hollow Dr, Middlebury
$619,900
3 Beds ⋅ 3 Baths ⋅ 24185515 MLS
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!

70 Pine Hollow Dr, Middlebury

700 Watertown Rd, Middlebury
$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, 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

700 Watertown Rd, Middlebury

66 Artillery Rd, Middlebury
$535,000
4 Beds ⋅ 4 Baths ⋅ 24164662 MLS
A piece of New England History on Fenn Pond. Circa 1803 "Todt Farm" is a truly distinctive center-hall Colonial set in an extraordinary Middlebury setting overlooking and adjacent to Fenn Pond. Surround by Middlebury Land Trust land, with preserved Brookdale Farm across the road, the property offers a rare sense of privacy, beauty and permanence. Inside, centuries-old character takes center stage with wide-board floors, seven fireplaces, rich horizontal paneling, built-ins, classic 12-over-12 windows and beautifully preserved front and rear staircases. The 11-room, 4-bedroom home pairs authentic architectural detail with the comforts of today, including a welcoming sunroom, stone patio, attached two-bay garage and 20kW Generac generator. Mature trees, gardens, stone walls and rolling lawns frame the home, while the pond setting creates an unmistakable sense of place. A rare opportunity to own an authentic piece of Connecticut history in one of Middlebury's most picturesque settings.

66 Artillery Rd, Middlebury

1140 Southford Rd, Middlebury
$399,000
24162191 MLS
Exceptional opportunity to acquire a 1.5-acre industrial development parcel located along the highly visible Southford Road corridor in Middlebury. Situated within the IG-40 (Gateway Industrial Design District), this property is ideally suited for flex industrial, contractor headquarters, light manufacturing, or office-warehouse development. The site benefits from access to public water and public sewer, a significant advantage that reduces development costs and increases allowable building density compared to typical septic-dependent parcels in the region. Positioned just minutes from Interstate 84, the property offers convenient regional access to Waterbury, Danbury, and the greater western Connecticut market. Existing Site allows for placement of a 2-story building consisting of 6850 S.F. per floor [13,750 S.F. total with 55 Parking Spaces. Due diligence required regarding changes to underlying zone

1140 Southford Rd, Middlebury

775 South St, 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

3 Brookside Dr Unit 3, 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

3 Brookside Dr Unit 3, Middlebury
$599,900
4 Beds ⋅ 4 Baths ⋅ 24145711 MLS ⋅ Brookside Of Middlebury BLDG.
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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