Lakeville, CT Classified Ad Listings

Lake Mansfield Rd. Lake Mansfield Lakefront Lot. Rare chance to live on a private road, on the prettiest of Lakes, minutes to downtown Great Barrington. Over 3 Acres with 175 feet of frontage in the most bucolic of settings. Make your dreams come true.

392-394 Park St. Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic ho...

162 Amenia Union Rd. This spectacular, light-filled, tastefully furnished four-bedroom, four-and-a-half-bath modern farmhouse offers an exceptional opportunity for an idyllic academic-year rental. Set on a quiet country road with complete privacy and breathtaking 360-degree views, the home enjoys an extraordinary setting where every room captures sweeping vistas of the surrounding countryside. ...

530 Milton Rd. Spectacular. Turn key. Authentic Salt Box circa 1756. One of the largest in Connecticut. It is in mint condition, with many recent updates. New mechanical systems, new kitchen and baths. A large generator is also a recent addition. A beautifully restored barn and a two car's garage are an additional bonus. The landscaped beds and garden, enhanced with stone walls add to the charm...

4 Gilmore Ave. Set on two-thirds of an acre in a residential area, walkable to all Great Barrington has to offer, this versatile home offers 4+ bedrooms and 3 bathrooms. The main floor boasts two bedrooms, a dedicated office or guest space, one and a half baths, laundry, as well as the main living, dining, and kitchen areas. Upstairs you will find 2 additional bedrooms and another half bath. Wo...

162 Hutchinson Pkwy. Built c. 1780, this distinguished center-hall Colonial was once part of the larger Butternut Brook Farm. Today, it is offered on 2 lots totaling 22.2 +/- acres on a quiet street in a coveted location w/open meadow views and 3 historically significant barns: a massive c. 1840 gambrel bank barn once used for hay, cattle, and later dairy operations, a smaller English barn whos...

594 Shunpike Rd. Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access...

145 Cornwall Hollow Rd. Nestled on five tranquil acres in historic Cornwall, this custom Lindal Cedar home presents an exceptional blend of New England charm and simple modern elegance, surrounded by nature in the incomparably beautiful Litchfield Hills. Soaring cathedral ceilings, rich timber framework, and warm hardwood floors define the open-concept living space, awash in natural light and a...

125 Taconic Creek Rd. Experience the quintessential Hudson Valley retreat in this private, 4-bedroom, 3-bathroom country home. Located just minutes from the slopes of Catamount Mountain Resort, this residence offers a seamless blend of rustic charm and modern convenience. The interior features a well-appointed kitchen and a living area anchored by a cozy wood stove--all complemented by tasteful...

155 Canaan Valley Rd. A DRILLED WELL, A COMPLETE 6 BEDROOM SEPTIC SYSTEM, A HORSE BARN AND A SHED COMES WITH THIS FABULOUS 42 PLUS ACRE PARCEL. BEAUTIFUL STONE WALLS SURROUND THE BUILDING SITE AND ACROSS FROM PROTECTED LAND

31 Sharon Rd Unit 2. Experience sophisticated country living in this exceptional, fully furnished residence overflowing with natural light and elegant finishes. Located on the ground floor of this historic building, this two-bedroom, two-and-a-half-bath dwelling is designed for immediate, effortless occupancy. The unit features a sweeping open-concept living and dining area with warm wood floor...

209 Route 343. A great opportunity to escape to your own private retreat in Millbrook. This property is for rent on an annual basis and offers 3200 sq ft of living space on 10 acres of beautiful land. Featuring 3 bedrooms, 2 full baths, and 1 half bath, this residence provides ample room for comfortable living. The first floor creates an inviting atmosphere for gatherings, with spacious formal ...

19 Robin Hill Ln. Fully Furnished Two-Bedroom Residence on Four Scenic Acres Experience the perfect balance of comfort, style, and countryside tranquility in this beautifully maintained, fully furnished two-bedroom, two-bath residence, privately situated above a three-bay garage on approximately four picturesque acres. Designed with an inviting open-concept layout, the home is filled with natur...

15 Hopkins Rd. AVAILABLE SEPT 3 2026 - MAY 2027@$5,750/Month. Classic European Farmhouse overlooking beautiful Lake Waramaug with deeded beach rights to the lake. This property is walking distance to the lake, a winery and restaurant. The amenities in the area include; hiking, kayaking, biking around the lake, shared access to Lake Waramaug, swimming and much more. Large bedroom with full bath ...

9 Park Ln. Single level living with room for everyone. This well loved Ranch House sits in a quiet park like neighborhood on a cul-de-sac. Livingroom with Fireplace, Eat-in Kitchen, 3 Bedrooms + a Bonus Bedroom that may double as an ADU (accessory dwelling unit), Rental or In-law suite. Large yard. Private Deck. Well located near shopping and schools. Truly a special home.. 4 Bedrooms. 3 Bathro...

86-90 West St. 86-90 West Street, Litchfield, CT offers the beauty of a character-filled antique home and the possibilities of three residential buildings, all in the center of historic town. A gracious covered porch, columned entrance, bay windows, and distinctive arched windows create an inviting architectural presence. With village shops, restaurants, and the historic Green nearby, this is a...

402 Park St. This well-maintained mixed-use property offers excellent flexibility for both commercial and residential use. The building is currently configured as two separate units. The first floor features a bright commercial space with large front-facing windows that provide excellent visibility and natural light--ideal for office or retail use. The space includes a private bathroom, dedicat...

310 Litchfield Rd. Known as "The Bungalow", this spectacular Tudor-inspired estate set on 43.8 private acres is one of architect Alfredo S.G. Taylor's finest designs. Built in 1908 for a Remington Arms heiress, the home seamlessly blends Gilded Age grandeur with exceptional modern luxury. The dramatic great hall features soaring 40-foot timber ceilings, a monumental stone fireplace, and exquisi...

107 S Main St. The Hatfield House: A rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character with modern systems; including a new sealed basement. A separate one-bedroom apartment with its own entrance provides income or guest flexibility. Plans for new 2nd floor bathroom! Set on 1.5 acres with protected wetland ...

264 And 260 Main Rd. A rare offering of 118 acres in the highly sought-after Tyringham Valley. Sage Hill Farm encompasses an exceptional landscape of rolling meadows and woodlands, mature landscaping, exquisite gardens, beautifully crafted hardscape and handsome barns. Dating to 1817, the main house retains many of its original architectural details and is complemented by a partially renovated ...