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287 W Main St, North Canaan
$299,000
3 Beds ⋅ 1 Baths ⋅ 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

469 Platt Hill Rd, Winchester
$895,000
4 Beds ⋅ 2 Baths ⋅ 24172121 MLS
HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 , 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors, to the 12 over 12 Windows and Fireplaces, Displays the Charm & Character in this Residence! For a more Modern Twist, there is a Fully Remodeled Eat-in Kitchen with Quartz Counters, as well as Remodeled Bathrooms. 4 TO 5 Bedrooms, 3 Full Baths, Formal Dining Room & Comfortable Living Room. Spacious Sunken 20' x 21' Family Room with Cathedral Ceiling. Unique Loft offers a Birdseye View to the Family Room. Level 7 Acre Lot Enhanced by Stone Walls and Nice Plantings. Outbuildings include a 30' x 35' 4 Stall Horse Barn with Tack Room & Hayloft. 2 paddocks and a 25' X 30' Storage Building. Mechanicals include Oil Hot-Air Furnace, New propane heat in the sunken living room,200 AMP Electrical Service, Well Water & Septic System. A Quaint and Rural Atmosphere, but within Close Proximity to Major Shopping, access to State Parks, Lakes, Golf Courses, Ski Areas, and Local Arts and Cultural Venues. The Photo Library Partially tells the Story, but prospective Buyers need to Visit / Tour this Lovely Property in order to Appreciate its Attributes!!

469 Platt Hill Rd, Winchester

117-118 Dibble Hill Rd, Cornwall
$1,945,000
4 Beds ⋅ 5 Baths ⋅ 24161510 MLS
The Stonewall Estate at Dibble Hill: Set across three distinct parcels totaling 19 private acres, this property offers a rare combination of architectural character, natural beauty, and long-term flexibility bordering protected land held by the Cornwall Conservation Trust. At its center, a 4,800+ sq ft contemporary barn-style residence is perfectly sited on 5 acres overlooking a spring-fed pond, framed by classic New England stone walls and thoughtfully designed gardens that evolve with the seasons. A sun-drenched glass entry foyer creates a striking sense of arrival, leading into expansive living spaces designed for both relaxed country living and sophisticated entertaining. The French country kitchen is exceptionally appointed with dual Sub-Zero refrigeration, multiple freezer drawers, and a six-burner Wolf range. The great room is dramatic featuring soaring beam ceilings, a commanding fieldstone fireplace, and four sets of French doors opening to a raised bluestone terrace. A fully enclosed glass solarium offers year-round connection to the surrounding landscape. The home includes 4 bedrooms, 4.5 baths with Waterworks fixtures, Travertine and wide-plank hardwood flooring. Beyond the main residence, a 11.5-acre buildable parcel directly behind the home for privacy and a 1.6-acre parcel across the street; Detached four-car garage with an additional space below. A rare opportunity to create a weekend or full time legacy estate in the Litchfield Hills.

117-118 Dibble Hill Rd, Cornwall

8 Red Mountain Rd, Salisbury
$500,000
24169493 MLS
The Ridge at Red Mountain: Own the land. Imagine the possibilities. Build on your timeline. Set along the foot of Red Mountain in Salisbury's desirable Lakeville area, this exceptional 5.42-acre approved building parcel offers a rare opportunity to secure a private country setting with long-range north and western views toward the Berkshires. Gently rolling terrain, neighboring farmland, and conservation-protected land adjoining the property to the north create a peaceful backdrop for a future residence. Whether you envision a sophisticated weekend retreat, a year-round country home, or a property to hold while planning your next chapter, The Ridge at Red Mountain offers the freedom to create something distinctly your own. The architect-owners have thoughtfully designed a proposed residence specifically for this setting, with architectural plans included in the land offering. Purchasers may explore that vision or pursue an entirely different design, subject to applicable approvals. Conveniently situated near the village centers of Salisbury and Lakeville, with access to dining, shopping, recreation, and Metro-North rail service. An opportunity to secure an exceptional homesite today and bring your vision to life when the time is right.

8 Red Mountain Rd, Salisbury

168 Fern Ave, Litchfield
$1,499,000
4 Beds ⋅ 4 Baths ⋅ 24166479 MLS
Welcome to Fern House at 168 Fern Avenue-an extraordinary private country estate set on 3.71 picturesque acres in one of Litchfield's most coveted enclaves. Perfectly tucked behind mature landscaping and approached by a graceful circular drive, this quintessential New England retreat offers the rare combination of luxury living, equestrian amenities, and resort-style outdoor spaces just moments from the storybook charm of downtown Litchfield. Spanning more than 3,600 square feet, this expansive contemporary residence is filled with natural light, soaring ceilings, and oversized windows that frame lush views in every direction. A dramatic double-height foyer opens to an airy, open-concept main living area anchored by a stunning floor-to-ceiling fireplace-creating both warmth and architectural impact. Designed for elevated everyday living and effortless entertaining, the chef's kitchen is beautifully appointed with premium appliances including double KitchenAid wall ovens, a five-burner cooktop, dishwasher, pantry, and dedicated office nook, all flowing seamlessly into gracious gathering spaces and a formal dining room. The flexible and thoughtfully designed floor plan offers four bedrooms and three-and-a-half baths, including a desirable first-floor primary suite option.

168 Fern Ave, Litchfield

202 Crane Hollow Rd, Bethlehem
$699,000
2 Baths ⋅ 24171303 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem

202 Crane Hollow Rd, Bethlehem
$699,000
24171301 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem

202 Crane Hollow Rd, Bethlehem
$699,000
5 Beds ⋅ 3 Baths ⋅ 24171297 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem

202 Crane Hollow Rd, Bethlehem
$699,000
3 Beds ⋅ 2 Baths ⋅ 24171289 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem

55 Ranney Hill Rd, Roxbury
$2,000,000
24170752 MLS
If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS! Bring your plans and build in a most beautiful part of the world in a sought after Connecticut town. Litchfield County is rural and beautiful. Enjoy farmers markets and country fairs. Visit any number of great restaurants in the area. There are many art shows, antique shops and boutiques to visit. As for outdoor activities, there are thousands of acres of land trust and hiking trails in Roxbury and surrounding towns. The Shepard River offers great fishing. There are ski areas close by as well as lakes for boating, fishing and swimming. Located under 2 hours from NYC! Taxes are based on 490 farming designation.

55 Ranney Hill Rd, Roxbury

436 Main St, Winchester
$250,000
24170540 MLS
One-of-a-Kind Opportunity! Don't miss your chance to own this turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location.-Owner Financing Available! This well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year track record of success and a loyal customer base, this restaurant has earned recognition in top publications including the New York Times, Wall Street Journal, Hartford Courant, CT Magazine, and numerous local publications - Sale includes the business only (real estate excluded) and comes fully equipped with all infrastructure items. This is a rare opportunity to step into a thriving, reputable restaurant with an exceptional reputation-ready to operate from day one - Numerous infrastructure items are included in the sale totaling well over 100k (See list in attached docs)

436 Main St, Winchester

Chestnut Land Road, New Milford
$1,300,000
24170226 MLS
An exceptional offering awaits with this one of a kind 61.54 acre parcel ideally positioned in a prime New Milford location, bordering the charming village of Washington Depot. This property is designated prime agricultural land, while also offering exceptional potential for a variety of future uses, including subdivision, a vineyard, equestrian estate, or private country retreat, solar farm. Featuring sweeping views with substantial level, usable land, the setting provides a beautiful and versatile landscape with endless possibilities. Originally subdivided in 1990 for 26 lots, any future subdivision would require new approvals, offering the opportunity to reimagine the property to today's standards. Enjoy the best of Litchfield County living with close proximity to downtown New Milford, as well as the scenic beauty of Lake Waramaug and surrounding towns. Maps and additional information available. A rare opportunity to bring your vision to life. Close to schools, shopping, dining, commuting with the ambience of New Milford and surrounding charming town of Washington Depot.

Chestnut Land Road, New Milford

221 Segar Mountain Rd, Kent
$915,000
4 Beds ⋅ 3 Baths ⋅ 24160643 MLS
Beautifully renovated antique colonial on 4.5 private acres with a tumbling brook. Hardwood floors and original beams throughout, two wood- burning fireplaces, custom lighting, original wide-plank floors in some rooms, and a gorgeous, country kitchen with built-in appliances, including a warming drawer. The formal dining room anchors the heart of the home, with a small private study for multiple uses on one side, and a large living room on the other side. Every room shows loving attention to detail and comfort. Added onto throughout the years, the house flows comfortably. The original cottage, connected by a light-filled inner hallway with hardwood floors, offers a lovely family room or second living room, with a wood fireplace, a full bath that includes an imported English claw-foot soaking tub, and a cozy upstairs bedroom for guests. There are two large barns: one is a combination garage, tool shed, and wood shed. The other, built using the chestnut beams from the original barn on the property, is capacious, with a cement floor and truly endless possibilities. Gorgeous antique stone walls and perennial gardens abound, and the property is private and protected in the back by its natural landscape. Split air conditioning and a generator assist with comfort without sacrificing authenticity. Close to town and 20 minutes to the Ten Mile River Train Station. This home has been beautifully maintained, and will be standing long after any of our new houses are long gone. Turn Key!

221 Segar Mountain Rd, Kent

130 Sharon Mountain Rd, Sharon
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 24168858 MLS
Lovingly named "Nid D'Alcyon," French for Kingfisher Nest, by the current owner, this truly enchanting home is rich in history. This beautiful four-bedroom antique, dating to circa 1745, is set on one of Sharon's most scenic roads and tells a captivating story of life, travel, and love. Nestled within exquisite gardens and surrounded by a serene pond, mature trees, and perennial plantings, the setting is both peaceful and picturesque. The current owner has lovingly stewarded the property for 37 years, thoughtfully enhancing it while honoring its character. With great care, the home was renovated to maximize natural light-an exceptional quality for an antique-through raised ceilings where possible and thoughtfully designed additions that invite sunlight throughout the day. Improvements include central air conditioning, a full-house generator, and an expansion of the original petite footprint typical of antique homes. A first-floor primary suite with vaulted ceiling and en-suite bath featuring a custom fireplace was added, along with a mudroom, sunroom, and chef's eat-in kitchen. The formal living room offers another fireplace and beautifully crafted built-ins, creating a warm and inviting retreat. Every corner reflects exceptional care, seamlessly blending antique charm with modern comfort. This rare offering also includes a heated Gunite pool and barn, all set on five acres overlooking a dreamy pond.

130 Sharon Mountain Rd, Sharon

184b Kent Rd, Warren
$179,900
24169359 MLS
Build your private getaway on 10.56 acres of woodland located between the two quaint New England towns of Kent and Warren in beautiful Litchfield County. Abutting hundreds of acres of Land Trust. Beautiful new access road has just been completed which provides entry to the front of the property from the road. Additional 14"+ added to driveway for proper drainage. Also replaced existing drain with a new plastic pipe under the driveway. The beginning of the driveway is shared with another lot. Buyer will need to extend the driveway to the back building envelop which is very private. There is an easement on this lot to the adjacent lot (184 Kent Rd., Parcel A) Kent Rd. is a main road but the lots are long, fairly level and deep so the building site could be situated well off the road. Approx 150 feet of road frontage. Close to chic shops and fine dining in New Preston and Kent. Access to the town beach on Lake Waramaug! 20 minutes to skiing at Mohawk mountain.

184b Kent Rd, Warren

134 Roulin St, Torrington
$295,000
3 Beds ⋅ 2 Baths ⋅ 24163896 MLS
A charming and sun-filled split-level ranch ideally situated on a quiet cut-de-sac. Though it does require some TLC to reach its full potential, it has three bedrooms and two and a half baths. This inviting home features gleaming hardwood floors and an abundance of natural light throughout. The open-concept living and dining area creates an easy, comfortable flow - perfect for both everyday living and entertaining. Sliding glass doors from the dining room lead to a spacious deck overlooking an above-ground pool, providing a great setting for outdoor gatherings. The lower level showcases striking black and white tile flooring and a generously sized room with a half bath, offering excellent potential for an in-law setup with walk out access. Set on a gently sloped, lightly wooded lot, the property offers a sense of privacy while still being conveniently located. There are two storage sheds and a new hot water heater as well. Easy access to I-84.

134 Roulin St, Torrington

30 Hollow Rd, Woodbury
$1,395,000
5 Beds ⋅ 5 Baths ⋅ 24168618 MLS
Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow Rd, Woodbury

12 Saville Dam Rd, Barkhamsted
$274,000
3 Beds ⋅ 2 Baths ⋅ 24169055 MLS
To settle an Estate. Dream location! 1008 SQ FT 3 Bedroom 1.5 Bath Ranch set on a Gorgeous .93 Acre Level Lot with Apple Trees! No issues with septic, well, furnace and roof.ADDED FEATURES: BASEMENT GARAGE! no more shoveling your car out.REAL WOOD BURNING FIREPLACE! BEAUTIFUL BAY WINDOW IN LIVING ROOM, ALL REAL HARDWOOD FLOORS, 100 AMP SERVICE, HOOK UP FOR AN EMERGENCY GENERATOR. DECK TO BACKYARD. POTENTIAL TO FINISH BASEMENT. Asphalt Driveway with convenient parking for at least 6 Vehicles. Close by to People's State Forest, Farmington River, Ski Sundown and the Ultimate Scenic Barkhamsted Reservoir. Close to Shopping and Medical Services in Winchester / New Hartford. 30 Minutes to Bradley International Airport. Property is being Sold in "AS IS" Condition. Any inspections done will be for informational purposes only! Cash or Conventional Financing.

12 Saville Dam Rd, Barkhamsted

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