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Cheshire Homes for Sale

Newest Sailsbury Homes For Sale

5 Prospect Mountain Rd, Salisbury
$100,000
24215757 MLS
Salisbury Building Lot 2+/- acres just east of the Village of Salisbury with potential for Western views. The septic plans for a 3-Bedroom home have been drawn. Abuts Town of Salisbury forest land which connects to USA land. Close to the Village of Salisbury, CT, the private schools, and Twin Lakes and just minutes to Sheffield and Great Barrington, MA, in the Berkshires.

5 Prospect Mountain Rd, Salisbury
70 Lincoln City Rd, Salisbury
$995,000
3 Beds ⋅ 3 Baths ⋅ 24207752 MLS
The best of both worlds: close enough to town for local shops and restaurants in moments, yet set high on Lincoln City Road with long views toward the distant Taconic Range. This darling neighborhood is steeped in local history. Lincoln City Road earned its name during the 1860 Lincoln Presidential Election, adding another layer of character to an already special setting. From the outside, Willa is a classic New England Colonial with charm and curb appeal in equal measure. Step inside, though, and the home takes on a more contemporary feel, with light-filled spaces and an easy, welcoming flow. At the heart of the home is the dining room, complete with gleaming hardwood floors, a wood-burning fireplace, and a wall of glass opening to the outdoors. Natural light pours in from every direction. The open dining area flows into an efficient kitchen with ample cabinetry, an electric cooktop, and wall oven, making it easy to entertain while staying part of the gathering. The oversized living room is made for board-game nights, watching the game, or simply settling in. A whitewashed chimney adds texture and character, while direct access to the deck extends the living space outdoors. The first-floor primary suite offers a private retreat, with a recently renovated bath featuring a double vanity, large tiled shower, and striking stone slabs. The walk-in closet is generously sized, with ample hanging space and custom built-in shelving.

70 Lincoln City Rd, Salisbury
48 Preston Ln, Salisbury
$699,000
2 Beds ⋅ 3 Baths ⋅ 24211378 MLS
Motivated Seller! Create your dream home on 3.12 private acres with access to Lake Washinee (Twin Lakes). This 2-bedroom home offers a spacious primary suite with laundry, an inground pool, and a large covered deck overlooking the yard and pool. The septic is sized for 3 bedrooms, and the lower level offers plenty of room for expansion. A private-road setting and room to grow make this a true blank canvas with endless possibilities! All room sizes are approximate.

48 Preston Ln, Salisbury
55-57 Brinton Hill Rd, Salisbury
$5,375,000
4 Beds ⋅ 3 Baths ⋅ 24206034 MLS
Renegade Farm is a breathtaking 85+ acre luxury countryside estate where the romance of farm-to-table living meets the indulgence of a private resort. The sprawling grounds feature a beautifully appointed 4-bedroom main house(4,504 sq ft) & a completely separate, spacious 4-bedroom guest house(4,074 sq.ft) making it an unmatched haven for multi-generational gatherings and high-end entertaining. The Main house features a dreamy chef's kitchen with mountain views, wood-burning fireplaces in the living room and family room are among many of the home's special attributes. The guest house is almost identical in size to the main house and also boasts two wood-burning fireplaces-one in the living room and the other in the family/recreational room-and two kitchens, one on each floor. Both homes enjoy large screened-in porches and outdoor courtyards, and total privacy between the 2 homes. Outside, a large garden retreat offers a true estate lifestyle, while wide, manicured trails wind through the vast acreage to reveal stunning, panoramic mountain views. The property includes a custom gunite pool, a newly resurfaced private tennis court, and a large fruit and vegetable garden. Renegade Farm is more than just a property; it is a magical, self-contained oasis designed for absolute privacy, active leisure, and serene natural beauty. Nearby - Catamount & Butternut, private & public schools, Twin Lakes & Lakeville Lake, and charming towns of Lakeville, Salisbury,Sharon & Great Barrington

55-57 Brinton Hill Rd, Salisbury
15 Walton St, Salisbury
$595,000
3 Beds ⋅ 2 Baths ⋅ 24207788 MLS
Classic Lakeville Colonial with Beautiful Gardens, Detached Studio & Walk-to-Village Location. Welcome to 15 Walton Street, a charming Colonial originally built in 1890 and thoughtfully renovated in 2000. This special home blends classic New England character with comfortable modern living and is ideally located within easy walking distance of the Lakeville village center. The approximately 1,173-square-foot home features 3 bedrooms and 2 full baths, traditional clapboard siding, and a welcoming front porch. The 2000 renovation complements the home's original character while providing a comfortable setting for today's lifestyle. Beautiful established gardens surround the property, creating a picturesque and peaceful setting throughout the seasons. The backyard offers space for gardening, outdoor dining, entertaining, or simply relaxing and enjoying the tranquil surroundings. A standout feature is the detached studio, currently used as a pottery studio. This versatile space is ideal for an artist, craftsperson, gardener, or hobbyist and could continue as a pottery or art studio, workshop, or creative retreat. A detached studio is a wonderful and uncommon addition to a village property. A convenient carport provides covered parking, while the front porch and intimate grounds create inviting spaces to enjoy the outdoors. The location is truly special. Just a short walk to Lakeville village. Whether a year-round residence or weekend retreat this home is truly special.

15 Walton St, Salisbury
250 Belgo Rd, Salisbury
$6,500,000
5 Beds ⋅ 6 Baths ⋅ 24208047 MLS
Clouds - An Architectural Retreat in Lakeville Set within 41 protected acres of rolling fields, wildflower meadows, and private trails, Clouds is an extraordinary contemporary country residence conceived in constant dialogue with its landscape. Approached along a winding drive through a cherry orchard-spectacular when awash in pink blossoms each spring-the house occupies the crest of a gentle bluff, commanding long views across meadows and to the distant Litchfield Hills. From a distance, the approximately 6,000-square-foot 5 bed and 5 full bath three level residence has the elemental simplicity of a refined agricultural building. Weathered cedar shake siding, a standing-seam stainless-steel roof, and a substantial stone chimney give the architecture a quiet permanence within its rural setting. Along the southwestern elevation, nearly 60 feet of windows transform the landscape into a living panorama, capturing rolling fields, wildflowers, mature trees, and the changing light from sunrise through magnificent south western views and sunsets. Inside, scale and light create an immediate sense of drama. The entrance opens to a remarkable 65-foot gallery with ceilings rising more than 20 feet. A ribbon of clerestory windows introduces eastern light from above, illuminating the walls and creating an exceptional setting for contemporary art. The principal rooms unfold enfilade along the western view, each with soaring ceilings and expansive glass framing the

250 Belgo Rd, Salisbury
87 Canaan Rd Unit 1D, Salisbury
$495,000
2 Beds ⋅ 3 Baths ⋅ 24208623 MLS ⋅ Lion's Head BLDG.
Set within the sought-after Lion's Head community, this refined condominium offers a rare blend of light, privacy, and architectural charm. The main level centers around an expansive living room bathed in natural light, anchored by a focal fireplace and framed by generous windows. The streamlined kitchen opens directly onto a private, patio set beneath the canopy of a weeping willow-an ideal backdrop for morning coffee or outdoor dining. Just off the kitchen, a formal dining space is wrapped in built-in bookcases, lending a warm, library-like atmosphere. A powder room, dedicated laundry, and abundant storage closets complete the main floor. Upstairs, two well-appointed en-suite bedrooms offer complete privacy and comfort. The primary suite features soaring ceilings that lend an airy, expansive feel, while the second en-suite bedroom is flanked by custom built-in shelving, making it equally suited as a guest suite or quiet reading retreat. It would be possible to convert dining room to first floor primary and and build a connecting first floor full bath. Lion's Head delivers an effortless, low-maintenance lifestyle with amenities that include a community pool and tennis courts. Perfectly positioned just moments outside of town, the property offers ultimate convenience to local dining, boutiques, and the nearby rail trail.

87 Canaan Rd Unit 1D, Salisbury
106 Farnum Rd, Salisbury
$459,000
3 Beds ⋅ 1 Baths ⋅ 24207808 MLS
Enchanted escape, loaded with charm! This lovely vintage 3 bedroom cape is shrouded with mature trees, flowering shrubbery and nestled privately on 1.08 acres. The old world stonework was cut and formed into the rock outcroppings decades ago by a master stone mason. This well built gem is solid as a rock. Turn key, with modern updates, hardwood floors, wood burning fireplace, built in dining hutch, an abundance of windows for cross breezes and plenty of sunlight. Serviced by town water and sewer is a real plus! There is a walk out from the one car basement garage. Our Tri-State area, beautiful Litchfield Hills, Berkshires MA and Hudson Valley NY are rich in culture, offering fine arts, restaurants with farm-to-table fare. Private and Public schools, medical facilities, golfing, skiing, hiking the AT, all within minutes. Come play, kayak, fish in out many lakes, rivers and streams. Less than 2 hrs and 1.25 hrs to NYC & Bradley Int airports respectively

106 Farnum Rd, Salisbury
87 Canaan Rd Unit 2G, Salisbury
$575,000
2 Beds ⋅ 3 Baths ⋅ 24208061 MLS ⋅ Lion's Head BLDG.
Here it is! Just what you have been waiting for. An updated unit in desirable Lions Head Condominium. Elegantly refreshed throughout from top to bottom. Recently redone hardwood floors, fresh interior paint & stylish new wallpaper create a clean, modern aesthetic. The gourmet eat-in kitchen with granite countertops, ample cabinet space, & stainless steel appliances beckon you to whip up a delicious meal on the 5 burner propane range. Step outside through the sliding glass doors to your private outdoor oasis-a beautiful flagstone patio surrounded by mature plantings providing a serene setting with a privacy fence & an open adjacent yard. The inviting LR has copious amounts of sunlight streaming in from the 3 sided end-unit position. Cozy up to the newly serviced wood burning fireplace & entertain guests with a separate wet bar in the LR. Main level half bath powder room. Second floor has 2 generously sized bedrooms - each with en suite baths. Primary bedroom w/skylight. Washer & dryer upstairs. New mini splits on both levels providing A/C. New hot water heater. Large one car detached garage w/shelving. Comfortable, easy living in a complex with well maintained landscaping, swimming pool, tennis courts, & responsible neighbors. Nothing more to do but relax & enjoy all Litchfield County has to offer - scenic beauty, cultural events, gourmet restaurants, antique shopping with prestigious private schools, & metro north train station nearby. Schedule now to appreciate this beauty!

87 Canaan Rd Unit 2G, Salisbury
10 Prospect Mountain Rd, Salisbury
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 24207746 MLS
Welcome to Forest's Edge. Set along a quiet country road traveled only by those with a reason to be there, this 1950s farmhouse presents that rare, elusive balance: complete sanctuary without isolation. Following a comprehensive, top-to-bottom renovation in 2021, every surface has been lovingly reimagined with an emphasis on quiet luxury and timeless craft. Arrival begins along a classic peastone driveway edged in Belgian block. A deep, welcoming front porch sets the scene generously scaled for classic Adirondack chairs, crisp afternoon breezes, and effortless entertaining. Inside, the main floor unfolds with natural light with windows surrounding the space. The living room serves as a cozy anchor, centered around a focal stone fireplace with a convenient propane insert and flanked by windows that invite sunlight to stream through all day. Just beyond, the dining area catches lovely views of the side porch stretching toward the pool. The kitchen is a beautiful balance of form and function: custom-paneled appliances, elegant marble countertops, a center island with an integrated breakfast bar, and a six-burner Wolf range equipped with a griddle and double ovens. Completing the main level is a powder room and a flexible front office that could seamlessly transition into a mudroom or playroom. The second floor hosts three spacious bedrooms, a full bath, and a dedicated laundry room that makes daily routines feel entirely luxurious.

10 Prospect Mountain Rd, Salisbury
348350 Main St, Salisbury
$949,000
3 Baths ⋅ 24207844 MLS
TURNKEY INVESTMENT OPPORTUNITY in downtown Lakeville. Step into a rare and lucrative investment opportunity in the vibrant heart of downtown Lakeville. This premier offering features two exceptional buildings boasting a combined 10 fully occupied units, seamlessly blending high-demand retail and professional office spaces. Designed for stability and immediate cash flow, this turnkey asset allows investors to acquire a fully stabilized property with established tenants already in place. Both buildings feature beautifully appointed common lounge areas, public restrooms, and handicap accessible ramps. Enjoy the added convenience of ample parking for tenants and customers, plus secure additional storage space in the basement.

348350 Main St, Salisbury
18 Burton Rd, Salisbury
$879,000
3 Beds ⋅ 3 Baths ⋅ 24208002 MLS
A Rare Find in an Exceptional Setting. Opportunities like this are few and far between - a beautifully located property with a Main House and a secondary studio-guest house. The two bedroom, two full bath main house radiates classic New England warmth, with hand-crafted oak kitchen cabinetry, pine-paneled ceilings, and a wood-burning stove that anchors the home in cozy, timeless charm. The main house has a semi open floor plan, the center of which is a spacious gourmet kitchen. The primary bedroom has its own adjacent office, and there is a second excellent office-bedroom on the main floor. The studio is a sun-drenched open concept loft with vaulted ceilings, offering wonderful flexibility - ideal for guests or extended family. This space would also serve as an incredible artist studio, offering endless possibilities. The lower level of the guest house has its own office, bath, and laundry. Set on a private parcel, yet just moments from the Salisbury Central School and the charming hamlets of Lakeville and Salisbury, the location is truly special. It sits in the heart of a highly sought-after area known for its excellent cultural and educational institutions, and serves as a gateway to the unspoiled beauty of Litchfield County, the Berkshires, and the Hudson Valley. The region is now widely considered one of the best places to live in the continental United States, and is prized for its proximity to New York City and the artistic hallmarks of the Berkshires.

18 Burton Rd, Salisbury
144 Salmon Kill Rd, Salisbury
$3,175,000
4 Beds ⋅ 4 Baths ⋅ 24207013 MLS
Set on prestigious Salmon Kill Road, this exceptional four-bedroom property blends refined luxury with the beauty and tranquility of its natural setting. With a seamless flow of indoor and outdoor living, this exceptional home pairs high-end finishes with an inviting sense of warmth throughout. The main level is designed for both everyday living and effortless entertaining, featuring a gracious living room with a fireplace, a comfortable family room with a woodstove, and a charming three-season porch that wraps around the eat-in kitchen. Abundant gathering spaces and a natural flow to the outdoors create an atmosphere that is both elevated and welcoming. The stunning primary suite is a private sanctuary, featuring two generous closets and a luxurious bath with a soaking tub overlooking the river-a truly special setting to begin and end the day. Two additional bedrooms and a full bath complete the second floor, one of which includes a private loft. A separate guest cottage provides exceptional flexibility, with a studio or workshop space below and a dramatic glass garage door opening toward the yard, ideal for an artist's studio, home office, or entertaining space. A heated in-ground saline pool anchors the beautifully landscaped grounds, surrounded by expansive lawns, mature trees, and meandering river views that create a private enclave.

144 Salmon Kill Rd, Salisbury
471 4 Undermountain Rd, Salisbury
$650,000
24201395 MLS
Imagine building your new home on a 7 acre lot in the very northwest corner of CT with a mountain view. It's less than 10 minutes to the town center of Salisbury, and less than half a mile to the Massachusetts border, which means that you're only a little more than 15 minutes to the happening town of Great Barrington. The lot features a picturesque rock outcrop in the middle (some clearing needed), and a subtle rolling terrain with a very nice high point as a home site. The driveway would be directly off a town road. Salisbury currently has one of the lowest property tax rates in the state. Don't let this one pass by!

471 4 Undermountain Rd, Salisbury
471 3 Undermountain Rd, Salisbury
$310,000
24201398 MLS
This affordable lot is just under 3.5 acres in Salisbury. The only clearing that's needed is for a driveway off the main road and to open up a potential view to the Taconic Range to the west if desired. Otherwise this lot is wide open and flat. There are a few possibilities here for a homesite, so the prospects are wide open. There's plenty of room for a pool, a garage, a guest house - whatever you might desire! It's about 8 minutes to downtown Salisbury and under 20 minutes to Great Barrington, MA - one of the coolest towns in the Berkshires. This property is a "must see" if you're hunting for the right spot in the Litchfield Hills!

471 3 Undermountain Rd, Salisbury
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