The agencies at Winchester
These agencies offer a selection of luxury properties vente at Winchester. Feel free to contact them for personalized assistance.
Breathtaking water views and master craftsmanship await in this pristine Colonial offering nearly 3,000 SF overlooking serene Highland Lake. This entertainer's dream home opens from an inviting two-story foyer into an airy, open layout where the living and dining rooms are joined by a floor-to-ceiling fieldstone fireplace. The spacious dining room easily accommodates large gatherings and flows seamlessly onto a delightful screened-in porch to enjoy the calm, serene setting with distant lake views. The gourmet kitchen is a master craftsman renovation featuring custom white birch cabinetry, rich soapstone countertops, stone subway tile backsplash, a farmhouse sink with a view, and a Sub-Zero refrigerator. Dedicated home office off front foyer, mudroom, laundry room, and half bath complete the main level. Upstairs features an en-suite primary bedroom, two additional nice-sized bedrooms, and a full guest bath. Accessed via a private second staircase off the kitchen, the expansive 27' x 21' "Skybox" family room (finished over the garage in 2017) boasts its own heating/cooling system, surround sound, and live music performance hook-ups. Property is flanked by a magnificent stone wall, emerald green meadows including a two-stall run-in shed with tack room. Hardwood floors main level, bamboo engineered floors upper level, oversized 2 car garage, walk-out basement. New well pump 2020, new whole house generator 2023. EZ commute to NYC & Boston from this ideal retreat. Rare opportunity.
…By William Pitt Sotheby's International Realty
YANKEE BARN AMERICANA Post and Beam. Renovation coming into completion. Newly renovated and refreshed - ready for the next chapter. Lovely and charming post and beam cape with soaring ceilings, massive beams, and lower level in-law apartment (or recreation / guest area) with kitchenette. Extensive deck overlooking private rear yard and woodlands. Quick walk to Sunset Beach for fishing, swimming, boating, lounging. WOODRIDGE LAKE: Private Lake Community offering miles of shoreline, 4 beaches, clubhouse, fitness center, tennis, pickleball, pool, basketball and playground, boat launch and marina.
…By William Pitt Sotheby's International Realty
Goshen, CT- This 4 bedroom, two and a half bath Colonial offers classic New England charm with modern comfort. The inviting living room features a fireplace and hardwood floors, opening to a deck overlooking landscaped lawn and garden. An ideal setting for relaxing and viewing the sunsets. A fully equipped eat-in kitchen, with breakfast area, separate dining room and a convenient first floor office make daily living easy. Upstairs, the primary suite includes a private full bath, large walk-in closet. There are three additional bedrooms with generous space. Additional amenities include a two car attached garage and a peaceful setting on a quiet street. This well-maintained home offers the perfect combination of comfort, space and location. Nearby activities include Farmers Markets, Agricultural Fairs, miles of walking trails and nearby Mohawk Ski area for winter fun. Sale is contingent upon Seller finding home of choice. Property be sold "As Is".
…By William Pitt Sotheby's International Realty
Introducing Butternut Brook House; a Majestic, Luxurious Country Estate commanding stunning 360-degree views of the Litchfield Hills. Representing a masterful fusion of absolute privacy, consummate sophistication and breathtaking natural beauty, this legacy property spans over 36 pristine acres of rolling countryside. The palatial main residence encompasses an impressive 13,056 square feet, including a recently appointed lower level. Accommodations are lavish, with seven principal bedrooms, each distinguished by its own fireplace and six & a half sumptuous baths. Inside, discover character-filled living spaces designed for grand entertaining and intimate repose. A spacious open plan kitchen / dining / family room flows into the formal Dining Room with custom millwork adjoining the elegant Living Room and screened porch. Luxury amenities abound, including an elevator to all 4 levels, a serene spa, dedicated billiards room and a timeless wood-paneled library/study. The second floor hosts dual primary suites and four supplementary bedrooms, while the third floor is home to a dedicated bunk room and a state-of-the-art home theater. The finished lower level is an entertainer's dream, offering a spacious recreation room, climate-controlled wine cellar, wet bar, two additional fireplaces, gym area and a half bath. The estate's auxiliary structures elevate the property to a luxurious, multifaceted estate and gathering complex. Comprising a generous two-bedroom guest house, private one-bedroom caretaker's cottage, an ample five-bay heated garage, separate tractor garage and two dedicated greenhouses. Further amenities include a Lit Tennis Court, heated gunite pool incorporating a spa, private tranquil pond, an extensive network of secluded walking trails and meticulously manicured, professionally landscaped grounds. All while remaining supremely convenient-just five minutes from the center of Litchfield for shopping and fine dining. This extraordinary Butternut Brook estate presents a rare opportunity to acquire a premier Litchfield County retreat, serving as the ultimate elegant full-time residence or a peerless luxury weekend escape.
…By William Pitt Sotheby's International Realty
Welcome to your private sanctuary-a stunning Mid-Century Modern retreat set on just under nine acres. This rare architectural gem blends timeless design with natural beauty and breathtaking scenic views. Step inside to discover classic details, including a three story center atrium, solid wood doors, rich architectural character with cathedral ceilings, multiple skylights and an exceptional amount of closet space throughout This home boasts a light-filled, open-concept living area with expansive windows capturing panoramic outdoor views. There is seamless flow into the dining space and kitchen, ideal for everyday living and effortless entertaining. This zen retreat with it's wrap-around mahogany deck provides direct access to the outdoors, perfect for taking in the tranquil surroundings. A massive upper-level primary retreat featuring generous proportions, a dedicated en-suite bath, and extensive closet storage. The three other spacious bedrooms on the lower level offer ample closet space and flexibility. Additionally, there is a flex space over the second 2 car detached garage Unbeatable convenience: peaceful retreat atmosphere while being mere minutes from Route 44, top-rated dining and the popular Shops at Farmington Valley.This unique estate offers the perfect balance of iconic design, modern comfort, and ultimate privacy without sacrificing proximity to everyday amenities. Schedule your private showing today
…By William Pitt Sotheby's International Realty
Escape to timeless Litchfield County living on coveted Pine St. with this extraordinary Cornwall estate, where classic New England charm meets modern versatility. Offering nearly 3,000 sq ft of sun-drenched living space, the main residence features an open-concept island kitchen flowing seamlessly into an expansive living room designed to capture sweeping western views and spectacular sunsets. Gentle morning sun filtering through mature hardwoods keeps the home naturally cool in summer. The main-level primary suite serves as a serene sanctuary with a generous walk-in closet and en-suite bath. Upstairs, you will find an additional bedroom, full bath, and a flexible library or office easily adaptable as a third bedroom. Outside, a screened deck lets you immerse yourself in every season. Above the attached two-bay garage sits a self-contained one-bedroom guest apartment-ideal for generating rental income, hosting long-term guests, or establishing an inspiring work refuge. Beneath the main level, an expansive walk-out basement awaits a custom workshop or extra living area. Uniquely combining a peaceful retreat with functional adaptability, this property is minutes from village centers, top schools, hiking trails, fly-fishing on the Housatonic River, and the historic West Cornwall Covered Bridge. Generator ready with a new roof installed in August 2026. Motivated seller-bring all offers to claim your dream home! New roof 2026
…By William Pitt Sotheby's International Realty
Introducing: Sage Hill The approach to this property is a slow one. Down a curved country road lined with evergreens that shade your path and allow dappled sunlight to light the way. A stone wall curves along the landscape, welcoming you to a drive anchored by a classic red barn. This 1890 farmhouse sits elegantly on a rolling lot, its large front porch making it easy to imagine long evenings watching the sun set with friends nearby. The foyer welcomes you with practicality and warmth. A bench for sitting while removing your boots, hooks for your coat. To the right is a sitting room with a wood-burning fireplace and large surrounding windows, making it a favorite room for humans and plants alike. To the left is the living room, with ample space for entertaining. Bookshelves line the far wall and a fireplace flanks them, making this a natural gathering spot after dinner parties. The dining room is a showstopper: soaring ceilings and detailed molding create a gracious space for holiday gatherings. The kitchen features a large walk-in pantry, a propane stove, a gorgeous decorative antique cookstove, and enough space for a dining table. The room opens beautifully to the pool area, with bluestone surrounding the space and a newly built gunite pool offering respite just steps away. The first floor also offers a full en-suite bedroom that could serve as the primary suite, guest quarters, or an in-law suite. In addition to the bedroom and bath, it includes a large living room with access to the outdoors. Upstairs, three additional bedrooms and two full baths plus a flexible extra room, ready to be transformed into an artist's studio, or a playroom.. The primary bedroom features two large walk-in closets and an en-suite bath. The property spans over nine acres. In true New England fashion, it includes meandering stone walls, and a red barn. Giving you every reason to explore. A fenced area surrounding the pool keeps all creatures, large and small, safely corralled. Located in the darling village of Cornwall. Home to Mohawk Ski Mountain, adored shops and restaurants, excellent fly fishing on the Housatonic, and the famous covered red bridge. Sage Hill is an elegant and graceful antique home, cared for deeply by her stewards of yesteryear. She now seeks her next steward in this lovely Litchfield County setting.
…By William Pitt Sotheby's International Realty
Introducing Cora, a Litchfield County jewel. Understated and quaint from the outside, this inviting home opens to a lovely landscape of stone walls, a wrought-iron gate, and stone steps leading to the front door. Inside, the living room makes an immediate impression with soaring ceilings and abundant natural light. Designed for both living and dining, the open-concept space is made for easy entertaining. French doors open to a bluestone patio overlooking a picturesque pond, framed by trees beginning to turn for the season and providing privacy in the summer months. It's easy to imagine long summer afternoons on a picnic blanket overlooking the spring fed pond reading your favorite book. The updated kitchen pairs modern fixtures with generous marble countertops and stainless-steel appliances. Down the hall, the primary suite includes an en-suite bath and a spacious walk-in closet. Upstairs, two additional bedrooms and a full bath with soaking tub provide flexible space for guests, work, or everyday living. Set on a lovely parcel in Cornwall Village, Cora is close to scenic views, local events, Mohawk Mountain, hiking, lakes, and all that Litchfield County has to offer.
…By William Pitt Sotheby's International Realty
Brand-new architecture that actually gets it right. 10+ private acres on a river in Litchfield, where cutting-edge design meets the kind of nature you thought didn't exist anymore. Single-level living done right: wide hallways, High ceilings, clean lines, polished concrete floors with radiant heat underfoot. Open concept living currently presented as a spacious dining area and two distinct living spaces leading to deck access perfect for outdoor entertaining. Well appointed Kitchen with breakfast bar seating and all the high-end touches you'd expect (and a few you wouldn't). Two primary suites one with a separate entrance, pre-plumbed for an additional kitchen, with laundry - perfect for parents / family. The other Primary suite features a top-tier infrared sauna. Two more bedrooms round things out. Tons of storage. Large family bathroom with claw foot tub. Step outside and it's your own private playground with direct water access and views of the river. Trails run into state land right from your backyard! Mohawk Mountain for winter ski weekends, access to Bantam Lake for summer days and the kind of privacy that makes you forget the world exists-yet you're minutes from refined dining and culture, quintessential New England villages, Litchfield's farm-to-table scene and Bantam's local charm. Furniture could be included if you want a totally turn key option!
…By William Pitt Sotheby's International Realty
Situated along a picturesque country lane, this private 4 BDR home is a light-filled sanctuary offering the perfect blend of gracious and serene country living. A welcoming front porch invites you into a spacious foyer, flanked by a quiet home study on one side and a large, sun-drenched living room anchored by a cozy fireplace on the other. A bright kitchen effortlessly connects a formal dining room to an expansive family room with vaulted ceilings and a second fireplace, creating a seamless flow for entertaining. Outstanding indoor amenities include a private sauna near the kitchen and a dedicated staircase leading to a versatile upper-level study or exercise room. Another set of stairs from the main entrance leads to the second floor featuring 3 generous bedrooms and a luxurious primary ensuite retreat, complete with its own private dressing/reading room and a balcony overlooking the grounds and distant views towards the Catskills. Outside, a lovely wood deck on the main level leads to a swimming pool and a classic barn, making this secluded estate an extraordinary haven inside and out. Close to Cream Hill Lake, Mohawk Ski Area, hiking and biking trails, area private schools, farm to table restaurants, fly fishing on the Housatonic and other unique treasures in the Litchfield Hills. 2 hours to NYC.
…By William Pitt Sotheby's International Realty
PHENOMENAL PANORAMIC VIEWS!!! This spacious, light-filled contemporary home features a 1400 sf legal in-law apartment just perfect for multi-generational living. Step inside this entirely renovated custom home with expansive windows atop Taine Mountain and enjoy peace and tranquility, sunsets and sunrises, every day of the year. Living room boasts gas fireplace & wood stove as well as the drama of soaring ceilings filled w light. Expansive renovated kitchen w/ granite countertops, tons of cabinet space, large island and access to balcony is a chef's dream. Cozy knotted pine family room w/ wide plank hardwood floors right off kitchen is grounded by a stone fireplace with gas insert. Generous 1st floor primary suite complete with walk-in closet and spa bath is your serene, peaceful retreat. Upstairs are 2 large bedrooms w Jack and Jill bath. There is also a large L shaped flex space w oversized windows, sliding doors and balcony perfect for office, gym, movie night or extra BR! Downstairs in finished lower level is a separate entrance that leads to a gorgeous in-law/au pair pad with separate bedroom, big kitchen, family room and rustic wood knotted pine den w fireplace & separate laundry room. Storage abounds upstairs and down. Unique property with new mechanicals, electrical systems, dual propane tanks (1 leased, 1 owned) updated heated & cooling & whole house generator. Wow! Fruit trees, gardens, berry bushes, a/c in the chicken coop! 2 hours to NYC & Boston. Extraordinary!
…By William Pitt Sotheby's International Realty
Exceptional custom residence set on 2 beautifully landscaped acres with sweeping lawns, stone walls, and stunning views of Heublein Tower and the surrounding hills. Designed with both elegance and everyday comfort in mind, this light-filled home features expansive windows, architectural details, and a thoughtfully designed floor plan. The chef's kitchen is centered around a 10' island and offers high-end appliances, gas cooktop with copper hood, pot filler, farmhouse sink, two dishwashers, and a sunny breakfast area overlooking the grounds. The spacious great room features a beamed ceiling and stone fireplace, while the formal dining room and private study enjoy beautiful views. A luxurious first-floor primary suite includes two custom walk-in closets and a beautifully appointed bath. A second main-level ensuite provides ideal guest accommodations. Upstairs are two additional bedrooms with hardwood floors, a Jack-and-Jill bath, sitting area, and access to a unique third-floor crow's nest that is ideal for an office or quite study showcasing incredible views. Additional features include a mudroom with built-ins, first-floor exercise/flex room, and walk-out lower level offering future finishing potential. Enjoy the private grounds, built-in firepit, and exceptional setting in a desirable location within the Town of Simsbury and the Simsbury school district, with an Avon postal address.
…By William Pitt Sotheby's International Realty
Welcome to Spring Path Farm-a serene and sophisticated 15+ acre gentleman's estate offering a rare blend of timeless country elegance, privacy, and endless possibility. Approached by a long, winding private drive, the stately 7,698 sq ft Colonial residence has been thoughtfully renovated and expanded with exceptional craftsmanship. Inside, classic millwork, four warm stone fireplaces, and floor-to-ceiling windows framed by stunning nature views set a refined tone. Designed for both relaxation and grand entertaining, the main house features a primary bedroom suite with a private deck for quiet mornings, a vast back deck built for summer gatherings, and a lower-level billiard and media room designed for lively hosting. Beyond the main residence, the lush grounds evoke quintessential New England charm. Meandering stone walls, stockade fencing, open meadows, and vibrant gardens filled with perennials and blueberry bushes offer a picturesque backdrop for equestrian pursuits, organic farming, or peaceful retreat. Exceptional outbuildings-including a magnificent barn, stables, and a 6-car detached garage-provide versatile space for livestock, equipment, or hobbyists. Meticulously loved and maintained, Spring Path Farm is a true sanctuary waiting for its next dreamer. Invite your guests for the weekend-they will never want to leave!
…By William Pitt Sotheby's International Realty
Situated on 10.94 private acres across Litchfield and Morris, this updated and charming Cape Cod home offers a perfect blend of comfort and scenic tranquility. The main level features a remodeled kitchen complete with quartz and soapstone countertops and a pantry with a dedicated coffee bar. The cozy living room highlights a wood-burning fireplace, flowing seamlessly into a sunroom overlooking the serene pond and professionally landscaped backyard. The main-floor primary suite boasts an updated bathroom, walk-in closet and a slider leading directly to the back deck. Convenience is the key with a main-floor laundry area, mudroom and half bath leading to the attached three-car garage, plus a versatile office/gym with a separate entrance. Hardwood flooring runs throughout both the main and upper levels. Upstairs you will find two comfortable guest bedrooms-one with a walk-in closet and a full bath. The finished lower level provides additional living space with a large family room and full bath, offering easy access to the patio and in-ground Gunite pool. An additional one-car under-house garage space provides ample storage for equipment or hobbies. Outside, enjoy the ultimate privacy featuring classic stonewalls and a dedicated garden area. Conveniently located just minutes from fine dining, shopping, golf courses, private schools and all the charm of the Litchfield area.
…By William Pitt Sotheby's International Realty
Designed to adapt effortlessly to daily routines and festive gatherings, this light-filled contemporary home located in the highly sought after neighborhood of Devonwood offers an intuitive layout across every level. The main floor centers around connected living spaces, where a dramatic two-story foyer and continuous hardwood floors guide you into the formal living and updated dining room. The heart of the home is the updated eat-in kitchen overlooking a cozy family room with bookshelves and a warm fireplace. Glass doors lead outside to an expansive bluestone patio with stone retaining walls perfect for outdoor dining and entertaining overlooking the private backyard. Every room prioritizes functional comfort. A study off the kitchen provides a quiet workspace while a sunroom retreat complete with a dry bar offers a peaceful escape with patio access. Everyday transitions are effortless thanks to a side mudroom entry featuring cubbies, hooks, storage and the first of two laundry rooms. Upstairs four bedrooms offer a quiet retreat anchored by a primary suite with generous his-and-hers walk-in closets and a dedicated second-floor laundry room. Situated above the garage is a versatile space with a full bath that adapts easily as a second family room, media space, or guest suite. The finished lower level provides even more living area with full bath, exercise room and space to play. Conveniently located to 184, Uconn Med Center and West Hartford Center 2 hours from NYC and Boston
…By William Pitt Sotheby's International Realty
The sellers built this cottage in the woods in 1987 and have kept it beautifully ever since. It sits well back from the road under towering oaks, nearly surrounded by New England stone walls, on a lane most people don't know exists. Permanently protected land is across the way, and no other house can be seen. Wind moves through the trees, birds are everywhere, and turkeys, deer, foxes and hummingbirds cross the yard. Inside, a wood stove anchors one large open room, with two bedrooms and a full bath on the first floor. A screened porch keeps the evenings bug free, and the newer two-car garage has a finished room above. The Otis beach on Big Pond is a 0.7 mile walk, and Tanglewood for music is about 30 minutes away. Priced within reach for year-round residents and part-timers alike. The first floor is easy to live in. One large room of warm pine walls holds the kitchen, dining and sitting areas around a wood stove, with windows that look into the trees. Two bedrooms and a full bath are on the same level. The floors are carpet and linoleum today. Wood floors throughout would suit the pine and the light, and it is an easy project to take on. A screened porch runs along the side of the house. It is where the sellers sit to listen to the birds and the wind, without bugs or weather. Below is a full walkout lower level, unfinished, with nearly three sides above grade, so there is a real opportunity to add space to the house later. The detached two-car garage is newer. The room above it, about 400 finished square feet, works for guests, a studio or a game room. That space is part of the 1,480 square feet in the listing, so the house itself is closer to 1,080. The land is 1.19 acres of wooded ground, a mown lawn around the house, a drive lined with hostas, and perennial plantings. The Town of Otis owns the land to the north, south and east. Across the country lane is permanently conserved Massachusetts Wildlife Management Area, and only one home lies beyond before the road ends and where more protected land begins. Wild turkeys, deer, foxes, bobcats and porcupines pass through, hummingbirds visit the yard, and the birds are constant. The wind in the trees is the loudest sound you will hear. With no city lights, the stars and the Milky Way are clear overhead.
…By William Pitt Sotheby's International Realty
Morris Gem! This solid and charming cape, built in 1956 when they knew how to build a solid house, has been loved by it's current owner for almost 35 years and is ready for a new chapter. Set back from the road behind a beautiful stone wall on 4.5 flat, gorgeous acres, it was recently outfitted with a new roof and a fresh coat of exterior paint. The furnace was replaced in 2024, oil tank in 2026 so you don't have to worry about the mechanicals! There is also an automatic on demand generator. The current dining room has a closet and adjacent full bathroom, so it's easily usable as a bedroom, which is how it was marketed when they bought it. The outside is where this property really shines, with several flat, open acres lined by stone walls. There is a pine grove perfect for picnicking, but you can enjoy the best of both worlds in the amply sized screened in porch. The partially finished basement is perfect for a workshop, gym or hobby room. Two acre residential zoning.
…By William Pitt Sotheby's International Realty
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These agencies offer a selection of luxury properties vente at Winchester. Feel free to contact them for personalized assistance.