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35 Emmons Ln, North Canaan
$1,135,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24192466 MLS
CANAAN VALLEY HOME WITH POOL & STUDIO Indulge in Litchfield County luxury at this homestead, proudly situated in Canaan Valley, offering picturesque views of fields from both the front and back of this 4-Bedroom, 3-Bath residence, plus a Studio with its own Half Bath. This property features a spacious single-level living home, a separate studio, and an inground pool. The home has undergone comprehensive updates, presenting a modern and welcoming interior supported by robust system and structural enhancements, which include: well, septic, roof, siding, and heating and cooling systems, automatic generator. The inviting interior harmoniously blends indoor and outdoor spaces, ensuring a solid foundation for years to come, where cherished memories can be created in this new chapter. The desirable Canaan Valley area in Litchfield County is conveniently located just a short drive from Great Barrington as well as the lakes of Salisbury. Enjoy nearby skiing at Butternut and Catamount, hiking throughout the region, including the Appalachian Trail, and dining in the charming villages that decorate the area.

35 Emmons Ln, North Canaan

11 College Hill Rd, North Canaan
$799,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24170495 MLS
Welcome to Owls Nest - a peaceful and private retreat tucked away on over 5 acres in the hills of Canaan in the foothills of the Berkshires. This beautifully maintained colonial offers 4 bedrooms, 3.5 bathrooms, and timeless charm throughout. Upstairs, all bedrooms feature hardwood floors, while the main level boasts 2 wood-burning fireplaces, a spacious living room, a formal dining room, and a cozy study with a stunning stone hearth. The kitchen includes an informal dining area and plenty of storage, making it perfect for both everyday meals and entertaining. It is a chef's delight. Dual ovens w air fryer, induction cook top, stainless hood and a natural live edge wood top. Step outside to enjoy your screened-in porch with ceiling fans, a large private deck w a hot tub, and a tranquil backyard surrounded by nature. The walkout lower level is finished with a full bath, an extra kitchen, and a bonus storage room ideal for a wine cellar. Additional features include a walk-up attic, central vacuum, ceiling fans, and garden spaces that attract gentle wildlife like deer, owls, and turkeys. Located on a quiet street and just minutes from skiing, golf, Lime Rock Park, fine dining, and cultural events, this home offers year-round enjoyment or a perfect weekend getaway. Lovingly cared for and thoughtfully updated by its current owners.Don't miss the chance to own one of Canaan's most serene and special properties. SqFt includes 1340 sqft in finished/heated lower level

11 College Hill Rd, North Canaan

25 27 Railroad St, North Canaan
$695,000
ACTIVE Status ⋅ 24183458 MLS
A landmark cultural anchor for over a century, The Colonial Theatre has stood proud in the heart of downtown North Canaan since 1923. Commissioned by a prominent local hotelier as a grand gesture for his wife, who had grown weary of quiet country living, this majestic three-level entertainment center was built to bring world-class vibrant energy to the Litchfield Hills. While its specific uses have evolved over the decades, its core purpose as a celebratory gathering place for the community remains beautifully unchanged. What truly sets this landmark commercial property apart is its remarkable versatility. In addition to housing approximately 400 guests across its two primary floors, the building features completely separate, high-visibility commercial retail units along the street-front facade, offering immediate income potential. Standing outside, you are immediately struck by the iconic, retro marquee; its brilliant neon lights perfectly set the stage for the magic that lies within. Meticulously maintained, the building underwent a comprehensive $1M+ restoration in the early 2000s that faithfully revived its original Art Deco details. Upon entering, a striking custom mural greets you, leading seamlessly to the vintage ticket booth and concession stand. Pass through the double doors into the massive main theatre, where you are met with soaring ceilings, flat tiered flooring, and structural seating for approximately 120 guests (with ample room to add seating).

25 27 Railroad St, North Canaan

27 Railroad St, North Canaan
$595,000
ACTIVE Status ⋅ 24178306 MLS
A landmark cultural anchor for over a century, The Colonial Theatre has stood proud in the heart of downtown North Canaan since 1923. Commissioned by a prominent local hotelier as a grand gesture for his wife, who had grown weary of quiet country living, this majestic three-level entertainment center was built to bring world-class vibrant energy to the Litchfield Hills. While its specific uses have evolved over the decades, its core purpose as a celebratory gathering place for the community remains beautifully unchanged. What truly sets this landmark commercial property apart is its remarkable versatility. In addition to housing approximately 400 guests across its two primary floors, the building features completely separate, high-visibility commercial retail units along the street-front facade, offering immediate income potential. Standing outside, you are immediately struck by the iconic, retro marquee; its brilliant neon lights perfectly set the stage for the magic that lies within. Meticulously maintained, the building underwent a comprehensive $1M+ restoration in the early 2000s that faithfully revived its original Art Deco details. Upon entering, a striking custom mural greets you, leading seamlessly to the vintage ticket booth and concession stand. Pass through the double doors into the massive main theatre, where you are met with soaring ceilings, flat tiered flooring, and structural seating for approximately 120 guests (with ample room to add seating).

27 Railroad St, North Canaan

136 Lower Rd, North Canaan
$575,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24184970 MLS
Blackberry River Oasis! With 1,100 feet of frontage on the Blackberry River and thousands of acres of protected state land as its backdrop, Stirling Farm offers a rare sense of privacy and tranquility. Cross a charming bridge with views of historic Beckley Furnace and its rushing spillway, then follow a private drive to a circa 1890 farmhouse nestled in a sunlit meadow. The home offers 3 bedrooms, 2 baths, and 1,500 square feet of living space. An updated kitchen with stainless steel appliances and a six-burner gas range complements original fir floors rich with patina, while a native stone fireplace anchors the spacious living room. Full of character and ready for its next chapter, the home presents an opportunity for thoughtful updates and personal touches to make it your own. The landscape is equally enchanting, with two magnificent mature Black Walnut trees, lovely apple trees, and a rare Rainier cherry tree offering its prized blush-colored fruit each June. Newly planted river birch, magnolias, and a graceful weeping willow add to the beauty of this ever-evolving setting. Private and serene, spend your days casting a line from the riverbank, listening to the gentle sound of the water, or simply unwinding as the Blackberry River sets the pace. With exceptional frontage and direct access, this is a place where nature, recreation, and quiet beauty come together.

136 Lower Rd, North Canaan

50 New St, North Canaan
$550,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24208063 MLS
Location, Location, Location! Welcome to this charming 3-bedroom Cape set on 3.5 beautiful acres in scenic Canaan Valley. Perched on the hillside, the home overlooks the open field below, offering a peaceful country setting and plenty of room to enjoy the outdoors. Inside, the spacious kitchen features a dining area and hardwood floors that flow throughout the main living spaces. The living room offers a cozy fireplace, built-ins, and large picture windows that fill the room with natural light. The dining area also features expansive windows showcasing the beautiful surroundings. A screened porch provides the perfect spot to relax and take in the views. The first floor includes a den with a full bath and a laundry room, offering excellent flexibility as a first-floor primary suite, guest space, or home office. Upstairs are three bedrooms and a full bath. The lower level adds even more usable space with a large finished living area and a workshop area, providing room for hobbies, recreation, or additional storage. Outside, a barn with stalls offers versatility for animals, equipment, or storage. A large two-car garage provides plenty of space for vehicles and gear, while a portable generator adds peace of mind. With its beautiful acreage, versatile floor plan, outbuildings, and peaceful Canaan Valley setting, this property offers a wonderful opportunity to enjoy country living with room to make it your own. All room sizes are approximate.

50 New St, North Canaan

53 Orchard Rd, North Canaan
$499,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214550 MLS
Welcome to this beautifully renovated and professionally decorated 3-bedroom, 2-full-bath ranch, offering the perfect combination of style, comfort, and easy one-level living! Thoughtfully updated throughout, this home features a spacious, flowing floor plan, abundant closet space, and tasteful finishes that create a warm and inviting atmosphere. The beautifully landscaped, level lot provides a wonderful setting for outdoor enjoyment, while the gorgeous rear stone patio is perfect for entertaining or simply relaxing. Recent improvements include new appliances, new windows, a new oil burner, updated electrical panel, totally renovated bathroom, and the addition of a third bedroom, adding valuable living space and functionality. The flexible layout also offers potential for an in-law arrangement, providing options for extended family or guests. Truly move-in ready, this exceptional home offers the charm of ranch-style living with the benefits of extensive modern updates.

53 Orchard Rd, North Canaan

37 Foote Ave, North Canaan
$489,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215629 MLS
Welcome to 37 Foote Avenue! Tucked away on a quiet dead-end street just minutes from downtown Canaan, this spacious 5-bedroom, 2.5-bath home offers 2,276 square feet of living space on a 0.39-acre lot. Featuring an updated kitchen and bathrooms, this home combines modern improvements with warmth, character, and plenty of potential. A wood stove provides an additional source of heat, while convenient main-level laundry adds to the home's functionality. The walk-up attic, already equipped with electricity, offers excellent potential for additional living space, a home office, or recreation area, subject to necessary approvals. Outside, a detached two-car garage provides ample parking, storage, or workshop space. The home is currently livable, with many updates already completed, while some finishing work remains, including select windows, exterior eaves, and interior ceiling panels. An excellent opportunity to enjoy a generously sized home while completing the remaining improvements to your personal taste. Conveniently located near downtown Canaan's shops, restaurants, and everyday amenities!

37 Foote Ave, North Canaan

125 S Canaan Rd, North Canaan
$469,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24186839 MLS
Back on the market due to previous buyer being unable to move forward with the purchase. Perched above the main road for added privacy, this newly remodeled home combines timeless charm with modern updates throughout. Beautiful engineered hardwood floors flow seamlessly through the living spaces, creating a warm and inviting atmosphere. The spacious living and dining room features a striking stone fireplace and French doors that open to an outdoor patio, providing an ideal setting for both everyday living and entertaining. The main level offers a desirable primary suite complete with a walk-in closet and an updated en-suite bath featuring a walk-in shower. A versatile den, also with French doors leading to the patio, provides the perfect space for a home office, family room, or guest retreat. A convenient powder room and generously sized laundry room complete the first floor. Upstairs, you'll find two additional bedrooms and a full bathroom, offering comfortable accommodations for family and guests. The beautifully updated kitchen is the heart of the home, featuring stainless steel appliances, expansive counter space, and a butcher block breakfast bar that is perfect for casual dining and gathering with friends and family. With its thoughtful floor plan, stylish finishes, and inviting indoor-outdoor living spaces, this move-in-ready home offers comfort, functionality, and exceptional appeal. All room sizes are approximate.

125 S Canaan Rd, North Canaan

287 W Main St, North Canaan
$320,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24172528 MLS
Nestled on a level in-town lot, this classic Colonial offers timeless charm, solid construction, and endless potential. Featuring three bedrooms and beautiful hardwood flooring, the home provides a warm and inviting layout ready for your personal touch. The front porch is THE perfect seasonal place to unwind after a long day or start your day with coffee! The adorable galley kitchen with convenient main-level laundry adds to the home's functionality, while a detached two-car garage offers additional storage and versatility. While the property could benefit from some cosmetic updates, it has been well maintained and stands on a strong foundation-making it the perfect opportunity to build equity and create your dream home. Located in the heart of Canaan, you'll enjoy the best of small-town living with the convenience of being able to walk right into town. Known for its scenic beauty and rich history, this charming Litchfield Hills community is home to the stunning Great Falls and the unique New England Accordion Connection & Museum Company. Surrounded by nature, outdoor recreation, local dining, and a peaceful rural atmosphere, Canaan offers a lifestyle that's hard to leave once you experience it. Whether you're looking for your first home, a weekend retreat, or a place to put down roots, this property is a rare opportunity to become part of a truly special community.

287 W Main St, North Canaan

335 Norfolk Rd, North Canaan
$279,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24178614 MLS
Built in 1910, this charming Colonial is currently configured as a two-family home, featuring a 2-bedroom apartment on the first floor and a 1-bedroom apartment on the second floor. With its flexible layout, the property could easily be converted back into a spacious single-family residence. The first floor offers a large country-style eat-in kitchen with a fireplace and pantry, a generous living room, and two bedrooms. Upstairs, the second-floor apartment includes a kitchen, living room, bedroom, and full bath. Additional features include a screened porch, a nice backyard, and plenty of potential throughout. Priced to sell, this home is ready for someone with vision to restore it to its full charm and character. All room sizes are approximate.

335 Norfolk Rd, North Canaan

335 Norfolk Rd, North Canaan
$279,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24178605 MLS
Built in 1910, this charming Colonial is currently configured as a two-family home, featuring a 2-bedroom apartment on the first floor and a 1-bedroom apartment on the second floor. With its flexible layout, the property could easily be converted back into a spacious single-family residence. The first floor offers a large country-style eat-in kitchen with a fireplace and pantry, a generous living room, and two bedrooms. Upstairs, the second-floor apartment includes a kitchen, living room, bedroom, and full bath. Additional features include a screened porch, a nice backyard, and plenty of potential throughout. Priced to sell, this home is ready for someone with vision to restore it to its full charm and character. All room sizes are approximate.

335 Norfolk Rd, North Canaan

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