North Canaan Real Estate

4 Beds ⋅ 2 Baths ⋅ 24193487 MLS

Nestled on a quiet cul-de-sac, this beautifully maintained Cape-style home offers privacy, character, and exceptional outdoor space on a level 2.37-acre lot. Featuring an attractive chateau-inspired exterior with a combination of stucco and wood siding, this home blends timeless charm with modern updates. Inside, you'll find four bedrooms, including a convenient first-floor bedroom and three additional bedrooms on the second level. The spacious primary bedroom features a private balcony overlooking the beautiful grounds. A full bath on both the first and second floors provides added convenience for family and guests. The home offers a large combination living and dining room, an inviting eat-in kitchen, and a cozy den warmed by a propane stove-perfect for relaxing on cool evenings. The finished lower level expands the living space with a generous family room, dedicated office area, workshop, and abundant storage. Additional highlights include a detached two-car garage with pull-down attic storage, a new roof installed in 2026, and a portable generator hookup for added peace of mind. The picturesque yard is a true highlight, featuring mature fruit trees, a lush green grape arbor, and plenty of open, level space for gardening, recreation, or entertaining. This is a wonderful opportunity to enjoy peaceful country living with the convenience of a thoughtfully maintained home. All room sizes are approximate.

4 Mountain View Ln, North Canaan

$1,135,000

4 Beds ⋅ 4 Baths ⋅ 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

$535,000

2 Beds ⋅ 1 Baths ⋅ 24191291 MLS

Rare Opportunity! This charming in-town, one-level ranch is located within the desirable sidewalk district and offers exceptional potential. Included with the property is an additional 1.82-acre parcel with access to town water and sewer. A feasibility study has been completed indicating the potential for three buildable lots, making this an outstanding investment or development opportunity. The well-maintained home features a spacious living room with a cozy fireplace, an eat-in kitchen with a new range and dishwasher, a dining room, laundry room, two comfortable bedrooms, and a full bath. Recent improvements include a new roof, replacement windows, two new Roth oil tanks, upgraded 200-amp electrical service, and a chimney that has been repointed, capped, and lined for added peace of mind. Outside, you'll appreciate the beautifully landscaped yard, a heated two-car garage with propane heat, and a 12' x 16' insulated shed with electricity-perfect for a workshop, hobby space, or additional storage. Whether you're looking for a move-in-ready home with room to grow or a property with outstanding development potential, this unique offering is one you won't want to miss. All room sizes are approximate. Seller will consider selling house & additional lot separately if there are buyers for both.

119 Bragg St, North Canaan

$335,000

4 Beds ⋅ 3 Baths ⋅ 24190537 MLS

Excellent income-producing opportunity in the heart of North Canaan! This well-maintained three-unit multifamily property is connected to town water and town sewer, has separate utilities for each unit, and offers an ideal addition to any investment portfolio or an excellent owner-occupied opportunity. The property features two one-bedroom, one-bathroom apartments on the main level, providing strong rental appeal with easy, single-level living. The upper unit occupies the second and third floors and includes two bedrooms, one full bathroom, a large second-story deck overlooking the town, and a finished third floor with two additional rooms that add exceptional flexibility and value. Beautifully updated while preserving its historic character, the property offers the charm tenants appreciate with the modern conveniences they expect. Its prime in-town location places shopping, dining, schools, parks, and other everyday amenities just minutes away, contributing to consistent rental demand. Whether you're expanding your portfolio, seeking a turnkey investment, or looking to live in one unit while generating rental income from the others, this versatile multifamily property presents outstanding long-term potential.

121 Railroad St, North Canaan

$335,000

4 Beds ⋅ 3 Baths ⋅ 24188055 MLS

Excellent income-producing opportunity in the heart of North Canaan! This well-maintained three-unit multifamily property is connected to town water and town sewer, has separate utilities for each unit, and offers an ideal addition to any investment portfolio or an excellent owner-occupied opportunity. The property features two one-bedroom, one-bathroom apartments on the main level, providing strong rental appeal with easy, single-level living. The upper unit occupies the second and third floors and includes two bedrooms, one full bathroom, a large second-story deck overlooking the town, and a finished third floor with two additional rooms that add exceptional flexibility and value. Beautifully updated while preserving its historic character, the property offers the charm tenants appreciate with the modern conveniences they expect. Its prime in-town location places shopping, dining, schools, parks, and other everyday amenities just minutes away, contributing to consistent rental demand. Whether you're expanding your portfolio, seeking a turnkey investment, or looking to live in one unit while generating rental income from the others, this versatile multifamily property presents outstanding long-term potential.

121 Railroad St, North Canaan

$199,900

3 Beds ⋅ 2 Baths ⋅ 24188763 MLS

Incredible opportunity to transform this solid 3 bedroom, 2 full bath Cape into your dream home! The main level features a spacious living room with a cozy fireplace, a formal dining room, a kitchen, a full bathroom, and two generously sized bedrooms. The upper level offers a third bedroom, a den, a possible fourth bedroom, a second full bathroom, and a convenient kitchenette, providing flexible living arrangements for extended family, guests, or a home office. Situated on a large, level yard with plenty of space for gardening, outdoor entertaining, recreation, or future improvements, this property offers endless possibilities both inside and out. Ideally located within walking distance of the town center, it combines small town charm with everyday convenience. Just 20 minutes from Great Barrington and surrounded by the natural beauty, outdoor recreation, dining, shopping, and cultural attractions of Litchfield County's highly desirable northwest corner, this home presents an outstanding opportunity for owner occupants, investors, or those seeking a weekend getaway. Being sold "as-is", this property is ready for its next owner to restore, renovate, and create something truly special!

49 Reed St, North Canaan

$350,000

6 Beds ⋅ 2 Baths ⋅ 24188125 MLS

RARE MULTI FAMILY OPPORTUNITY - Side by side duplex with 3 bedrooms in each unit. All individual utilities including separate oil baseboard heat. One unit has had an extensive renovation just completed, the other needs updating. Detached two car garage, and both units have an enclosed rear porch. Convenient in town location is walking distance from dining, pharmacy, post office, library, elementary school, pool and more. Ideal for owner occupancy in one unit while the other is brought up to date.

71 Railroad St, North Canaan

$475,000

3 Beds ⋅ 3 Baths ⋅ 24186839 MLS

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

$870,000

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

$695,000

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

$599,000

3 Beds ⋅ 2 Baths ⋅ 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

$279,000

3 Beds ⋅ 2 Baths ⋅ 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

North Canaan Real Estate

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