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49 Reed St, North Canaan
$165,000
3 Beds ⋅ 2 Baths ⋅ 24211798 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, formal dining room, kitchen, full bathroom, and two generously sized bedrooms. Upstairs offers a third bedroom, den, possible fourth bedroom, second full bathroom, and convenient kitchenette, providing flexible space for guests, a home office, hobbies, or additional living areas. Set on a large, level yard with plenty of room for gardening, outdoor entertaining, recreation, or future improvements, this property offers tremendous potential both inside and out. Ideally located within walking distance of the town center, the home combines small town charm with everyday convenience. Just 20 minutes from Great Barrington and convenient to Salisbury, Lakeville, Falls Village, Lime Rock, Norfolk, the Berkshires, the Appalachian Trail, and the Housatonic River, the property is surrounded by the natural beauty, outdoor recreation, dining, shopping, and cultural attractions that make the Northwest Corner such a desirable place to live or escape to. An excellent opportunity for owner occupants, investors, or those seeking a weekend retreat, this home is being sold as is and is ready for its next owner to renovate, restore, and make it their own!

49 Reed St, North Canaan

15 Locust Hill Rd, North Canaan
$339,000
5 Beds ⋅ 2 Baths ⋅ 24196917 MLS
Nestled in a peaceful, secluded setting just off Route 44, this well-maintained two-family property offers an excellent opportunity for both investors and owner-occupants. The first unit features three bedrooms, including a convenient first-floor bedroom, a full bathroom with stackable laundry, and a functional layout designed for comfortable living. The second unit offers two upstairs bedrooms and in-unit laundry, with the washer and dryer owned by the current tenant. Each unit enjoys its own private deck, providing a comfortable outdoor space to relax or entertain. The property also features separate utilities, making management simple and efficient. Currently tenant-occupied, this income-producing property combines privacy, convenience, and strong rental appeal in a desirable location with easy access to Route 44.

15 Locust Hill Rd, North Canaan

348 Norfolk Rd, North Canaan
$349,000
3 Beds ⋅ 1 Baths ⋅ 24175854 MLS
Charming 1935 Cape full of character and timeless craftsmanship on 2.87 acres! This well-built home features custom carpentry throughout, including beautiful built-ins, classic woodworking details, and a built-in dining room hutch that adds warmth and charm. The flexible first-floor layout offers a possible bedroom or den, along with a full bath, kitchen, dining room, and inviting living room. Upstairs you'll find three nicely sized bedrooms, including two with custom window seats and additional built-ins that showcase the home's original character. Major exterior and mechanical updates have already been completed, including vinyl siding with added 2" insulation, replacement windows, roof, deck, covered front porch, and propane furnace/hot water system. Outside, enjoy a large level yard with abundant parking and a spacious 23x23 workshop - ideal for hobbies, storage, or projects. A river runs through the back section of the property, adding to the peaceful setting. With the big-ticket improvements already done, this home is ready for someone to bring the interior back to life and restore it into a true gem. All room sizes are approximate.

348 Norfolk Rd, North Canaan

22 Raymond Ave, North Canaan
$369,500
2 Beds ⋅ 2 Baths ⋅ 24193811 MLS
Rare Riverfront Cottage located directly along the scenic banks of the Housatonic River, this enchanting 2-bedroom, 1.5-bathroom cottage offers the perfect blend of rustic charm, timeless architectural details, and uninterrupted nature views. Two bedrooms have been thoughtfully built around the center great room with soaring cathedral ceilings. The dramatic exposed volume creates an airy, light-filled atmosphere that instantly feels expansive allowing for open concept living and dining. Effortlessly entertain or enjoy comfortable daily living in this lounging space, anchored with a vast stone fireplace. The prime riverfront location lets you enjoy immediate access to the Housatonic River right out your back door-ideal for kayaking, fishing, or simply taking in the wildlife. The massive enclosed porch is the absolute crown jewel of the home. Enjoy panoramic, unobstructed water views in year-round comfort, while you're sipping morning coffee or hosting evening sunset drinks. Whether you're searching for a peaceful weekend retreat, or a picturesque year-round home, this riverfront haven is ready to impress.

22 Raymond Ave, North Canaan

121 Railroad 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

49 Reed St, North Canaan
$158,500
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

315 Salisbury Rd, North Canaan
$190,000
3 Beds ⋅ 1 Baths ⋅ 24170905 MLS
Opportunity knocks! This 2-story Cape Cod is set on .67 acres and offers strong potential for investors, contractors, "ideal for those looking to add value over time." Being sold as-is, the home currently offers 3 bedrooms and 1 full bath, while town records reflect 4 bedrooms and 2 baths. The layout has been opened to create a more spacious living area and features a functional floor plan ready for your vision and updates. Interior highlights include some original hardwood flooring and laminate, along with radiant floor heat on the first level. The previous deck has been removed, and exterior improvements are needed-making this an ideal opportunity to customize and add value. Additional features include private septic, public water, oil heat with hot water baseboard, and a central air system that is not currently connected, with existing duct-work already in place. The unfinished basement provides utility access and exterior entry. Shared driveway. The property is taxed as one parcel and includes a small section extending across the road, which is non-buildable. This is a solid opportunity to improve and occupy. Cash or Conventional financing preferred. Schedule today!

315 Salisbury Rd, North Canaan

15 Honey Hill Rd, North Canaan
$735,000
4 Beds ⋅ 3 Baths ⋅ 24152723 MLS
Oh, My Darling: Clementine. This 1752 Georgian Colonial is the missing piece in your New England dream. Lovingly and thoughtfully renovated by its current steward, no detail has been overlooked yet the home's original character remains beautifully intact: hand forged hardware, hand hewn beams, and wide plank floors. Enter through the gracious mudroom, which opens into the living room, where exposed beams immediately draw the eye. Lime plastered walls and floors refreshed with a soft white finish create a space that feels both historic and quietly modern, the perfect room for welcoming guests. The dining room offers generous proportions, easily accommodating a large table for gatherings with family and friends. Just beyond, a cozy first floor office provides a convenient and secluded workspace. The kitchen is bathed in natural light from abundant windows. Tasteful updates, including new appliances and quartz countertops, lend a clean, modern serenity while remaining true to the home's character. A full bath is tucked just off the kitchen for added ease. At the front of the house, an additional living room features built-in bookcases, hand hewn beams, and ample space to settle in with a good book. Upstairs, four bedrooms are thoughtfully arranged across two staircases. One wing holds the primary bedroom, gracious in scale and filled with natural light, a true country retreat along with another bedroom and a full bath.

15 Honey Hill Rd, North Canaan

22 Pease St, North Canaan
$315,000
3 Beds ⋅ 2 Baths ⋅ 24174432 MLS
Surprisingly spacious and full of charm, this well-maintained home offers comfortable living on a small in-town lot in a highly convenient sidewalk neighborhood. Enter through the welcoming enclosed porch into a warm and inviting interior featuring beautifully refinished hardwood floors throughout and freshly painted rooms. The main living area includes a bright living room with built-in shelving that gently separates the dining room, creating both character and functionality. A cozy den, half bath, and spacious eat-in kitchen provide plenty of room for everyday living and entertaining. The kitchen, porch and bathrooms feature new flooring for a fresh, updated feel. Beyond the original kitchen area, a hallway leads to three nicely sized bedrooms and a full bath, offering a practical layout with privacy from the main living spaces. Additional highlights include a whole-house generator, carport, paved driveway, and a sweet rear yard with a small deck overlooking a peaceful stream bordering the property. Perennials and mature shrubs surround the home, adding seasonal color and curb appeal. Conveniently located within the town sidewalk district, this property is close to the ball field, town pool, and elementary school, making it an ideal location for enjoying community amenities and in-town living. Subject to Probate Approval. All room sizes are approximate.

22 Pease St, North Canaan

70 Church St Unit D-1, North Canaan
$198,500
2 Beds ⋅ 2 Baths ⋅ 24164638 MLS ⋅ Church Street Condo BLDG.
Skip the renovations and move straight into this chic, end-unit townhouse where "new" is the recurring theme. Every inch of this 2BR condo has been curated for modern tastes, featuring all-new flooring, sleek cabinetry, and stone counters. The open, light-filled layout is complemented by a fresh designer palette and brand-new stainless appliances. The dry basement level with high ceilings is ideal for a home gym. Beyond the stylish interior, life here is all about convenience. Leave the car at home and walk to the center of town in minutes to enjoy local shops and dining. With a private rear deck for morning coffee and a full basement for all your storage needs, this home offers the perfect blend of in-town proximity and residential comfort.

70 Church St Unit D-1, North Canaan

16 Browns Ln, North Canaan
$345,000
2 Beds ⋅ 1 Baths ⋅ 24167306 MLS
This comfortable 2-bedroom Cape offers a bright and open living, kitchen, and dining area, highlighted by a soaring cathedral ceiling that creates an airy, welcoming feel. A cozy loft sitting area with brand-new carpeting overlooks the main living space, providing the perfect spot to relax or work from home. The flexible layout includes one bedroom on the main level and a second upstairs, offering privacy and versatility. A woodstove in the living room serves as an efficient and inviting heat source, while solar panels add energy efficiency and long-term savings. Recent updates include a new gas stove in the kitchen and a new propane hot water heater. Freshly painted interior. The spacious first-floor laundry/mudroom adds everyday convenience and offers potential for a home office setup, along with additional workspace options in the loft. Outside, enjoy a level yard with plenty of parking, a two-car garage, patio, and storage shed. Mature pear and peach trees add charm and a touch of nature to this well-rounded property. All room sizes are approximate.

16 Browns Ln, North Canaan

26 Granite Ave, North Canaan
$595,000
5 Beds ⋅ 3 Baths ⋅ 24153529 MLS
This North Canaan home in town boasts a spacious Main Home along with a Guest House situated on a 1.32-acre lot. The 5-Bedroom Main House is bathed in sunlight and features a lovely flow on the main floor that seamlessly connects a formal Living Room with a fireplace, a Media Room, an Office, the Dining Room, and a Kitchen with a Breakfast Bar that overlooks the backyard. The generous ceiling height and an inviting front entry hall enhance the ambiance of this beautifully crafted 1882 homestead. The Media Room has access to the adjoining Full Bath, making it a versatile First Floor En Suite Bedroom as well. Upstairs, you'll find an additional Primary Bedroom Suite complete with its own Bathroom, along with three other Bedrooms that share a hall Bath featuring a separate shower and a clawfoot soaking tub. All Bathrooms have been tastefully updated. The Carriage House at the rear of the property has also been carefully updated to take advantage of the expansive backyard and the abundant sunshine that graces the property. The Main Floor includes a Kitchen, Living Room, and a full bath that opens to a private back deck. The upper-level loft captures the essence of a true Carriage House. This presents a fantastic opportunity for an income-generating cottage or an exceptional Guest House for hosting friends and enjoying the charm of Litchfield County.

26 Granite Ave, North Canaan

143 E Canaan Rd, North Canaan
$1,000,000
6 Beds ⋅ 3 Baths ⋅ 24152414 MLS
Exceptional country estate on 16.65 pristine acres offering the ultimate in privacy and convenience without isolation. This remarkable North Canaan property features a 3 car garage-ideal for automotive enthusiasts to enjoy nearby Lime Rock Park. Inside, the chef's kitchen with commercial prep area is an entertainer's paradise, designed to accommodate everything from intimate dinners to large-scale catered events with ease. The expansive grounds provide endless possibilities for grand-scale entertaining, intimate gatherings, or peaceful countryside retreats. An additional parcel conveys with the sale, ensuring maximum privacy and future flexibility. Perfectly positioned between Connecticut's Northwest Corner and the cultural richness of the Berkshires, you're moments from Tanglewood's world-class performances and direct access to the Appalachian Trail for hiking and outdoor adventure. This property is ready for its next steward to reimagine it and make it their own for the finest country estate living.

143 E Canaan Rd, North Canaan

37 Greene Ave, North Canaan
$370,000
3 Beds ⋅ 1 Baths ⋅ 24155171 MLS
Welcome home to this beautifully maintained 1,332 sq ft, 7-room gem nestled in the charming town of North Canaan. Set on a lightly wooded half-acre lot, this sun-filled home offers the perfect blend of comfort, style, and space. Step inside to find neutral tones and elegant decor that create a warm, inviting atmosphere throughout. In addition to three comfortable bedrooms and one full updated bath, the home features a living room highlighted by a beautiful bay window that fills the space with natural light. The spacious family room addition, featuring a vaulted ceiling and pellet stove, provides an ideal setting for gatherings and entertaining. The thoughtfully designed kitchen features newer appliances, an abundance of cabinetry, and an open layout that flows effortlessly into the casual dining area and family room. Natural light pours in through plentiful windows and sliders lead to a covered deck-perfect for morning coffee or evening relaxation. An exterior door provides easy access to the expansive, private backyard offering plenty of room for outdoor fun. Enjoy added comfort with central air, an attached one car garage, newer driveway and newer stone walls.The walk out basement offers excellent potential for additional living space - perfect for a home office/home gym etc .This delightful property combines charm, functionality, and comfort--an exceptional opportunity in a welcoming community. Presented in move-in-ready condition with convenient location!

37 Greene Ave, North Canaan

182 Church St, North Canaan
$300,000
3 Beds ⋅ 2 Baths ⋅ 24103146 MLS
Welcome to this classic 3-bedroom Colonial, ideally situated on the outskirts of town yet just a short stroll to the sidewalk district. This home blends timeless charm with functional living spaces, perfect for families or anyone looking for a comfortable setting with easy access to town amenities. Step inside to discover hardwood floors that flow throughout the home, adding warmth and character to every room. The dining room features crown molding and a built-in hutch. Upstairs, you'll find three bedrooms and a full bath. One bedroom opens to a large enclosed porch-perfect for a cozy sleeping porch, sunroom, or playful retreat. A convenient half-bath is located on the main floor for guests. Enjoy your morning coffee on the welcoming front porch, or unwind after a long day. Two car detached garage with extra space in the back previously used for chickens. New house roof. This home is full of potential and charm-don't miss the chance to make it your own! New septic will be installed prior to closing. All room measurements are approximate.

182 Church St, North Canaan

246 Ashley Falls Rd, North Canaan
$280,000
4 Beds ⋅ 2 Baths ⋅ 24140480 MLS
Welcome to this Spacious 4-bedroom, 2-bathroom Colonial offering 2,214 sq. ft of inviting living space on a .44-acre in-town lot in the heart of North Canaan. Step inside to a spacious country kitchen, perfect for family gatherings. The bright and airy floor plan features multiple living areas with plenty of natural light and traditional charm throughout. Upstairs, you will find generous bedrooms, ample space for family and guest. This traditional home blends charm with comfortable living and an opportunity to update and make it your own. Additional highlights include a single-car garage that provides convenient parking and storage, as well as level yard with room for outdoor enjoyment. Set on a peaceful lot surrounded by the beauty of Northwest Connecticut and the Litchfield Hills. This property combines small-town serenity, with close access to local amenities, schools, and area recreation. Close proximity to Wassaic Train Station, 2 Hour trip to NY City and a quick trip to enjoy all the arts and entertainment the Berkshires have to offer.

246 Ashley Falls Rd, North Canaan

33 Granite Ave, North Canaan
$475,000
5 Beds ⋅ 2 Baths ⋅ 24122249 MLS
Charming 5-Bed Village Colonial in the Heart of North Canaan Set in a desirable sidewalk neighborhood, this fully renovated Colonial blends timeless charm with modern comfort. Updates include new electrical, plumbing, replastered walls, refinished main-level floors, all-new baths, and a stunning kitchen. Freshly painted throughout, it's move-in ready. A welcoming front porch opens to a light-filled foyer and airy layout, ideal for family living and entertaining. Sun-drenched rooms flow into the modern kitchen with access to a deck and patio-perfect for outdoor dining. A flexible first-floor study offers a great home office option. The walk-up attic provides room to expand or create a studio. Outside, the landscaped backyard is a private retreat with lawn, gardens, fruit trees, and blooms year-round. Close to ski resorts in MA and within walking distance to the pharmacy, post office, library, grocery, playgrounds, and lifeguarded town beach, this home offers both convenience and tranquility. Recent upgrades include a new furnace (installed 1/15/25). Room sizes approximate.

33 Granite Ave, North Canaan

123 Lower Rd, North Canaan
$385,000
3 Beds ⋅ 3 Baths ⋅ 24100824 MLS
This is an amazing opportunity to own a completely renovated home offering a private yard and a fabulous location! Step inside to a spacious living room that flows seamlessly into the dining area, creating the perfect space for entertaining. Just off the main living area is a versatile bonus room-ideal for a home office, playroom, or first-floor guest bedroom. The first floor also features a brand-new full bathroom and a high-end kitchen equipped with stainless steel appliances, a large central island with seating and storage, custom cabinetry, and sleek quartz countertops. Upstairs, you'll find two generously sized guest bedrooms that share a beautifully updated full bathroom. The stunning primary suite includes a walk-in closet and a luxurious en suite bathroom with double shower heads and body jets. Additional highlights include: Brand new gleaming hardwood floors, New well pump, Energy-efficient mini-split heating and cooling systems, all new electrical, plumbing, and electrical panel, new siding, roof, windows, and insulation, first-floor laundry room with direct access to the backyard & large outdoor shed for extra storage. Every detail has been thoughtfully updated-just move in and enjoy a modern, turnkey home with style, space, and comfort.

123 Lower Rd, North Canaan

46 Old Turnpike Rd N, North Canaan
$450,500
3 Beds ⋅ 2 Baths ⋅ 24141602 MLS
Welcome to this inviting log cabin set on 7 peaceful acres in a highly desirable location. Warm pine accents carry throughout the home, enhancing its rustic charm and comfortable atmosphere. The spacious open living and dining area features a striking cathedral ceiling, a fireplace with a woodstove insert, and dual sliding doors that extend to a wrap-around covered porch-perfect for enjoying the surrounding natural beauty in any season. The kitchen offers excellent counterspace and a bright skylight that fills the room with natural light. This home provides abundant storage and a well-designed layout, offering two bedrooms and a full bath in addition to a generous primary suite. The suite includes a large walk-in closet, a convenient laundry area, a second full bath, and a nicely sized bedroom. The lower level adds even more versatility with a large finished room ideal for play, entertainment, or hobbies. Additional features include a two-car garage under the home, a separate storage room, and a well-appointed workshop with double steel doors providing easy access from the garage. A paved driveway completes the property. Embrace the privacy, space, and character this exceptional log cabin has to offer. All room sizes are approximate.

46 Old Turnpike Rd N, North Canaan

72 N Elm St Unit APT 2E, North Canaan
$146,500
1 Beds ⋅ 1 Baths ⋅ 24137178 MLS ⋅ Meadow Wood Village BLDG.
Nicely renovated and move-in ready! This bright one-bedroom, one-bath second-floor condo offers comfortable and efficient living close to town and within the sidewalk district. The updated kitchen features stainless steel appliances and a smart, functional workspace. Beautiful bamboo floors flow throughout the open living area. The nicely sized bedroom includes a slider leading to a small landing with rear stairs. Convenient in-unit laundry hookups with an appliance included. Furniture shown in photos is included with the sale, making this a truly turnkey opportunity. New windows and slider. HOA covers trash removal, lawn care, snow plowing and locked mail boxes. Room sizes are approximate. Subject to Probate Approval.

72 N Elm St Unit APT 2E, North Canaan

338 Salisbury Rd, North Canaan
$280,000
3 Beds ⋅ 1 Baths ⋅ 24129562 MLS
Welcome to this beautifully maintained three-bedroom home located on the peaceful outskirts of town. Step inside to discover a stunning remodeled kitchen featuring granite countertops, stainless steel appliances, and a premium Viking 4-burner propane stove. French doors lead out to an inviting patio complete with a pergola - perfect for relaxing or entertaining guests. The impeccably landscaped and fully fenced backyard offers both privacy and charm, creating an ideal space for outdoor gatherings. Inside, the cozy living room is highlighted by a wood stove, adding warmth and character. Upstairs, you'll find three comfortable bedrooms, a convenient laundry area, and a newly remodeled bathroom. Additional highlights include new replacement windows throughout, a new oil tank in the basement, and the potential to add a first-floor bathroom. The property also features a one-car garage with an overhead door opener and additional barn doors on the side, offering extra storage or workshop space. measurements are approximate. Don't miss the opportunity to make this charming, move-in-ready home yours!

338 Salisbury Rd, North Canaan

101-10 Sand Rd, North Canaan
$310,000
4 Beds ⋅ 2 Baths ⋅ 24133150 MLS
Set back from the road on a shared driveway, this 4-bedroom, 2-bath Cape offers a peaceful setting with a large, mostly wooded lot and plenty of space to expand your private yard area. The main level features two bedrooms, a full bath, and a freshly painted living room with beautiful cherry plank flooring. The kitchen and dining spaces flow nicely, providing a comfortable layout for everyday living. Upstairs are two additional bedrooms and another full bath. One of the upstairs bedrooms, highlighted by a large Palladian window, makes an ideal den or cozy retreat and features a pellet stove for added charm. The home includes a second pellet stove on the main level, though they have not been used in some time. The large, dry basement with hatchway access offers great storage or workshop potential. Recent updates include a newer roof and gutters. With a little TLC, this home has wonderful potential to shine. Conveniently located close to town amenities while offering privacy and space to enjoy nature. All room sizes are approximate.

101-10 Sand Rd, North Canaan

19 Ryan Ave, North Canaan
$654,000
2 Beds ⋅ 3 Baths ⋅ 24124468 MLS
This stunning 2,299 sq ft log cabin-inspired Beaver Mountain home on 4.42 private acres in North Canaan has been meticulously cared for by its original owners. Built in 2005, this exceptional property showcases rustic charm with modern comfort while delivering breathtaking panoramic views across the rolling Litchfield Hills. Featuring 2 bedrooms, den, loft, 2.5 baths, soaring timber details, and expansive windows that frame the ever-changing vista like living artwork. The thoughtful siting maximizes optimal views from multiple vantage points throughout the property. Located in North Canaan's peaceful setting with ultimate privacy, you're perfectly positioned for small-town charm while remaining convenient to outdoor recreation and Litchfield Hills amenities. This home is your front-row seat to nature's daily masterpiece.

19 Ryan Ave, North Canaan

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