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Cheshire Homes for Sale

Newest Sailsbury Homes For Sale

$915,000
4 Beds ⋅ 3 Baths ⋅ 24203167 MLS
Introducing: Penelope. This home unlocks a new tier of Lakeville living. Set in one of the town's most coveted, close to everything neighborhoods, it places the lake, town parades, bike path, and local dining right at your fingertips. The location is almost secondary to the house itself: this might just be the best-maintained home we've ever seen, with no detail too small to be thoughtfully reimagined. Inside, natural light floods the oversized living room, framing garden views where you can lounge on the couch and watch hummingbirds flit between flowers. The adjacent dining room provides a flexible space, accommodating a boisterous dinner parties just as easily as tea for two. In the kitchen, fresh paint, updated appliances, and pearl hexagon backsplash offer ample workspace for your resident chef. If your chef has unexpectedly retired, dinner at Fern or White Hart are just moments away. Updated floors and fresh paint enhance the main floor, anchored by a primary suite featuring generous closets. Attached is an elegantly designed bath with charming black and white penny tile. Two additional main floor bedrooms and full bath easily give you flexibility as guest quarters or a quiet home office. Downstairs is where you will likely gasp, "There's more?" Positioned right off a heated two-car garage that makes cold New England mornings officially a thing of the past, the laundry room is so cheery you'll actually volunteer for an extra load.

30 East St, Salisbury
$599,000
3 Beds ⋅ 2 Baths ⋅ 24203742 MLS
Nestled in a private setting, this home features a stunning driveway that meanders through its 1.84-acre property and is located in the sought-after Lakeville community. Enjoy the convenience of single-level living with complete updates throughout. The expansive Living Room boasts a cozy Fireplace, while the Dining Room and Kitchen seamlessly connect to a spacious Screened Porch. There are three bedrooms, including one with an en suite bathroom, while the other two share a Full Bath conveniently located off the hallway. The full basement is equipped with modern mechanicals and offers great bonus space. Experience the tranquility of nature and privacy, all just minutes away from town in this peaceful neighborhood.

27 Robin Hill Ln, 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
$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
$875,000
24201392 MLS
This is one of the most stunning medium-sized land parcels in NW Connecticut. It's primarily an open field, part of a horse farm, with a tree lined entrance and a 180 degree view of the Taconic mountain range from south to north. Set well off the main road, the building site is relatively flat, with an attractive fence at the perimeters. It's a blank canvas waiting for the right buyer with vision and a sense of pride in the surroundings. Plenty of space for a pool and/or tennis courts, barns, other outbuildings - whatever may be desired, and no tree clearing is necessary. Imagine having this view every day, especially with the colorful fall foliage!

471 2 Undermountain Rd, Salisbury
$4,275,000
4 Beds ⋅ 5 Baths ⋅ 24200461 MLS
Set on 7.06 acres in a premier Salisbury location, this custom-built modern farmhouse, completed in 2022, captures sweeping western mountain views across a beautiful pastoral landscape. Designed for exceptional one-floor living, the home is filled with natural light and thoughtfully oriented to take full advantage of its remarkable setting. At the heart of the home, a dramatic vaulted great room with exposed beams, a propane fireplace, and expansive walls of glass opens to the dining area and kitchen, creating a bright, inviting space with mountain views always in sight. The spacious kitchen features a large center island and adjoining butler's pantry, ideal for both everyday living and entertaining. The home offers four bedrooms, including a private primary suite with spectacular views and a light-filled, spa-like bath with a freestanding soaking tub and marble shower. Additional bedrooms also enjoy abundant natural light and views of the surrounding landscape. A dedicated fitness area provides additional space for recreation and wellness in the lower level. The lower level can be finished to accommodate more living space. Outside, professionally landscaped grounds surround the home, with broad lawns, open meadow, a heated gunite 16 x 50 pool and spa, and multiple areas for outdoor living-all set against an extraordinary mountain backdrop. House includes an auto-testing generator.

360 Taconic Rd, Salisbury
$2,595,000
5 Beds ⋅ 5 Baths ⋅ 24201998 MLS
The Yellow House is a warm and gracious country retreat set amid an extraordinary natural landscape at the gateway to the Berkshires. Just minutes from the charming villages of Salisbury, Lakeville, Norfolk, Sheffield and Great Barrington, the property offers easy access to the exceptional cultural, culinary, and recreational offerings of the Massachusetts-Connecticut border. Set against a backdrop of rolling hills, open meadows, gardens, and mature trees, the property was designed to embrace its spectacular surroundings. Light-filled interiors are relaxed and inviting, with expansive views. The grounds offer an exceptional country lifestyle, with an organic vegetable garden, apple orchard, and acres of meadow enclosed by a mowed walking loop. Whether enjoying a morning walk, an afternoon in the garden, or the changing beauty of the seasons, the land is as much a part of the experience as the house itself. Inside, a central kitchen serves as the heart of the home, connecting a thoughtfully arranged collection of spaces including a formal dining rm, living rm, media rm, breakfast rm, and sunroom. The floor plan offers both elegance and flexibility, with wonderful spaces for entertaining as well as comfortable living. The home is officially 5 bedrms, but has flexibility for use as 8 or more bedrms, providing generous accommodations for family and guests. Recent improvements include a new furnace, wood-shingle roof, new gym in the barn, and new hardwood floors on 3rd floor.

547 Under Mountain Rd, Salisbury
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 24199395 MLS
This newly constructed 4 bedroom 3.5 bath modern farmhouse in the Twin Lakes community enjoys shared access on Lake Washinee. The home's minimalist design melds simplicity with sophistication. Rooms are light filled with seamless vantage points to take in the natural beauty of the out-of-doors. Fresh timbered beams, two story windows, solid white oak floors, solid hemlock & mahogany doors, Carrara countertops, just some of the finishings. Whether entertaining or the desire for quietude, there are spaces to accommodate everyones needs..an Adirondack room off the kitchen, an intimate patio setting, huge deck & a delightful entertainment room with walk-out to a large patio. The great room has a 28ft ceiling, stone surround wood-burning fireplace & a ton of ambiance. Paneled walls & a gas fireplace in the 1st flr bedroom/library add a level of comfort & warmth. The primary bedroom has a beautiful ensuite bath. Open the double doors to its charming balcony & absorb the feeling of "en plein air". Private & public schools, train, medical facilities, riding trails, shopping, all within minutes. Enjoy hiking and biking trails, kayak, play, fish in our many lakes, rivers & streams. Rich in culture, our beautiful Litchfield Hills, Berkshires & the Hudson Valley have ample farm markets, country fairs & restaurants serving farm-to-table fare...just some of the perks. Less than 2 hrs & 1.25 hrs to NYC and Bradley Int airports respectively

26 Preston Ln, Salisbury
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 24188003 MLS
Tucked into a quiet, private setting just minutes from the heart of Salisbury, this distinctive Trelleborg home offers a wonderful sense of calm and connection to nature. Scandinavian in character, its clean architectural lines, warm wood details and abundant natural light create spaces that feel both relaxed and inviting. The main level flows easily from the spacious kitchen to open living and dining areas, where doors lead directly to an expansive deck overlooking the surrounding trees and gardens-an ideal setting for morning coffee, outdoor dining, or simply enjoying the peaceful surroundings. Throughout the home, wood floors and ceilings bring warmth to the architectural design, while skylights and generous windows frame the landscape and fill the rooms with natural light. Upstairs, the pitched rooflines create charming, character-filled spaces that feel intimate and distinctly Nordic. The finished lower level adds valuable flexibility, with space well suited for a home office, gym, sitting area, or a combination of all three. Outside, beautifully considered gardens are woven into the natural setting with stone paths, sculptural plantings, ornamental grasses and mature trees, creating an almost Zen-like atmosphere. This home feels wonderfully secluded without being remote. Private, peaceful and close to town, this is a home that invites a quieter rhythm of life. Find your peace in Salisbury.

24 Burton Rd, Salisbury
$2,275,000
5 Beds ⋅ 4 Baths ⋅ 24194898 MLS
Welcome to The Parsonage, the Colonial style house that was built for the Salisbury Episcopal Church pastor in 1964. It sits among a beautiful and desired stretch of New England homes on Main St. and has been very recently gut renovated both inside and out including mint 3 zone HVAC system, heated salt water pool, plumbed Carriage House to the back with Belgian Block driveway. Sitting on 1 horizontal acre in the it has gorgeous forest and Mountain views. The expansive chef's kitchen has all Bosch appliances .The dining and living rooms banked by windows and French doors open to the flagstone and stone terrace large enough for dining and sitting areas. A wood burning fireplace anchors the generously proportioned living room which includes built in shelves making it warm and cozy during the winter months. The ample foyer stretches back to an office with shelving, a full bath and downstairs bedroom. Linking it all is a dry bar which connects with the kitchen, pantry/mud room and 2 car garage to the back.

72 Main St, Salisbury
$975,000
4 Beds ⋅ 4 Baths ⋅ 24193314 MLS
Renovated Village Home, Guest House and Separate Work Studio! Located in the heart of Salisbury Village, this beautifully updated home offers 3-4 bedrooms & 3 full baths in the Main Home plus an additional 620 sq ft, 1BR, 1BA Guest home. The main home's layout is on a generous, level lot, combining classic New England character with thoughtful modern updates. The inviting chef's kitchen with a casual adjacent dining room is filled with natural light from oversized windows overlooking the expansive side and backyard. Stretching across nearly the entire front of the home, the welcoming living room features a wood-burning fireplace and opens to a spacious covered front porch-ideal for relaxing, entertaining, or enjoying every season. A renovated full bath and a first-floor office or efficiency bedroom provide flexibility for remote work, guests, or single-level living. Upstairs, a graceful original staircase leads to 3 additional bedrooms, including a generous primary suite and laundry room. Two guest bedrooms share an updated full hall bath, while the primary suite features an en suite bath ready for your personal finishing touches. The 1-BR Guest House with full kitchen, living room, full bath, & laundry is a potential source of rental income. Private backyard space makes for easy living! The newly converted shed with new windows & insulation is now a perfect Office Space or Art Studio. A rare opportunity to enjoy in-town living in the Northwest Corner of CT.

56 E Main St, Salisbury
$475,000
4 Beds ⋅ 2 Baths ⋅ 24194914 MLS
Presenting a rare and wonderful opportunity to own two utterly charming antique cottages-each featuring 2 bedrooms and 1 bath, and situated on its own separately deeded parcel. This unique setup offers tremendous flexibility to offset your living costs: live in one while renting the other, maximize your income by renting both, or keep one and sell the other. Significant capital improvements have been made over the last few years, including a new shared drilled well, extensive tree clearing, a new septic system for one cottage and structural work where needed. There are new kitchens and updated bathrooms. Both homes are filled with historic character, boasting cozy wood-burning fireplaces and airy cathedral ceilings. Located in the heart of the Lime Rock section of Salisbury, the Airbnb, VRBO, and long-term rental potential here is exceptional. You are close to the historic Lime Rock Park racetrack, three prestigious area private schools, and endless year-round cultural and outdoor activities.

And10 Forge Ln, Salisbury
$485,000
2 Beds ⋅ 3 Baths ⋅ 24190973 MLS
This 1850 Antique home has been proudly cherished and meticulously cared for by the same family for 59 years. It is ready to be passed on to the next owner to enjoy all the beauty, cultural activities & outdoor recreation the coveted NW corner of Litchfield County provides. Proximity to the renowned Lime Rock Park Racetrack is sure to please automotive enthusiasts. Nearby prestigious private schools make this an ideal primary dwelling, or a weekend escape to rest & recharge. Upon entering the large living room, one immediately feels the warmth with wall to wall carpeting and a fireplace. An additional den/sitting room w/fireplace compliments the living area. A country styled, eat-in kitchen w/pantry area, tile floor, ample cabinets & large picture window is inviting. For more lively family gatherings, there is a formal DR w/french doors leading to a spectacular sun porch with walls of windows creating a tranquil, relaxing ambiance, flooded with natural sunlight. The upper floor has a primary bedroom with large, built in closets, a full bathroom with tub and a 2nd bedroom. The concrete floor basement has a full bathroom w/shower stall, utility sink & laundry with entrance to a one car attached garage. Oil steam boiler recently rebuilt & serviced regularly, chimneys repointed, heightened & capped, new water tank 2024. There is an outdoor storage shed on the property. Come see for yourself this special property & all it has to offer!

465 Lime Rock Rd, Salisbury
$595,000
2 Beds ⋅ 2 Baths ⋅ 24192177 MLS
The Cub House Located in the coveted Twin Lakes area of Salisbury, The Cub House is all about possibility. Set on nearly six acres along a quiet gravel road, this property offers an ideal address, beautiful natural surroundings, and the chance to either improve the existing It features a functional layout with a comfortable kitchen that opens into a large living and dining room with a fireplace. The primary has an ensuite bath and the second bedroom and hall bath complete the main floor. There is also a covered porch and an open deck. The lower level has an additional semi-finished room, plus ample storage, laundry and a garage. The home offers a solid foundation for updates. Whether you're looking to modernize the existing structure, create a custom country getaway, or expand your footprint on the generous acreage, the possibilities are endless. Enjoy total seclusion surrounded by nature, while still being just minutes from lake recreation and town conveniences. Bring your contractor and your design ideas. Properties with this much land and privacy in this location do not come along often! Imagine crisp mornings on your porch, afternoons on the water, and evening walks in this coveted lake community. Dive into lake life, and never look back. Offered as-is.

149 Rocky Ln, Salisbury
$1,645,000
4 Beds ⋅ 3 Baths ⋅ 24190420 MLS
Timeless New England Charm on Coveted Wells Hill Road Dating to circa 1850, this beautifully preserved country home is a quintessential Lakeville retreat, blending historic character with the relaxed elegance of Litchfield County living. Set on two open, level acres and bordered by protected land, the property enjoys exceptional privacy, pastoral views, and a peaceful sense of permanence. Inside, the home offers four bedrooms and three baths, with warm, inviting spaces that celebrate its historic roots while accommodating modern living. Original architectural details, generous rooms, and abundant natural light create an atmosphere that is both welcoming and timeless. Outdoors, the property is designed for making the most of every season. An in-ground swimming pool anchors the landscape, while a charming gazebo provides the perfect setting for afternoon gatherings, evening cocktails, or quiet moments overlooking the expansive grounds. With protected acreage as your backdrop, the setting feels remarkably private and serene. Ideally located on one of Lakeville's most desirable country roads, 461 Wells Hill Road is just minutes from the village centers of Lakeville and Salisbury, Lake Wononscopomuc, hiking and biking trails, acclaimed private schools, and the vibrant cultural and culinary offerings of the Northwest Corner. Whether as a full-time residence or a weekend escape, this is a rare opportunity to own a classic Connecticut country property in an extraordinary setting.

461 Wells Hill Rd, Salisbury
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