luxury houses for sale Winchester, United States

Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at your fingertips. The property's outdoor allure is undeniable. Multiple walking or riding trails invite adventure, and the gardens, barn, carriage house and stone outbuilding offer endless possibilities for outdoor enjoyment. Step inside and be greeted by the warm embrace of rich hardwood floors, two fireplaces, French doors, and meticulously crafted woodwork that tell tales of yesteryear. The updated kitchen, equipped with a premium Wolf gas stove and a convenient butler's pantry, offers a perfect stage for culinary exploration. The living room, anchored by a cozy fireplace, formal dining room, and library, are infused with great natural light that dances across the spaces. The primary bedroom suite, a sanctuary of comfort, boasts its own fireplace, ensuring a restful retreat at day's end. Accommodate guests in style with four additional bedrooms, including a secluded guest room with a private stairway. Located in the heart of nature's playground in Litchfield county. Close to skiing, hiking, restaurants, and parks in Norfolk and Barkhamsted, and near the Farmington River.

Welcome home. This three-bedroom, one and a half bath property is located on a quiet road enjoying both convenience and privacy. The first floor features a modern kitchen that looks onto a formal dining area, which opens to a beautiful outdoor deck and yard, equipped with a new spacious storage shed. The light-filled living room makes for an intimate and welcome setting. The main floor living space sits adjacent to a full bath with separate laundry. On the upper level, a primary bedroom and two additional bedrooms share a half bathroom. A wonderful opportunity to own just minutes to downtown Torrington offering restaurants, community, culture and more.

Fresh, timeless and custom crafted. Build your dream home in the picturesque town of New Hartford. Beautiful, energy efficient 4 bedroom, 2 1/2 bath farmhouse Colonial on a private, serene 4.3 acre lot. This exquisitely appointed home boasts luxury, meticulous style and unparalleled craftsmanship in every detail. Spacious light filled kitchen with large center island opens to a lovely breakfast area and nice sized family room w gorgeous hardwood floors and gas log fireplace, perfect for hosting holiday events, family gatherings and more! Upstairs you will find the luxurious Primary bedroom suite w fabulous walk-in closet, luxe bath, double sinks and tile walk-in shower. There are also three good sized bedrooms and an additional media/game -anything you can imagine- room making this home a cut above the rest. CUSTOMIZE THE FLOOR PLAN! Construction has not yet started so there is plenty of time to make it your own. Whatever is on your wish list this sun filled, gorgeous 4.30 acre home site is your canvas. Country living at its best just minutes to Route 44 and the town center, where you will find boutique shops, great restaurants, the Farmington River. Just a stone's throw away from Ski Sundown and all kinds of outdoor recreation and fun. Live life to the fullest in the home of your dreams. Images are from renderings or photos of builder's previous homes, similar to what is planned. Still time to choose everything!

Nestled in the heart of the completely private 1700 acres of the Doolittle Lake Company woods on 2 parcels, this 100 acre 5,670 sq ft beautifully maintained 1780 center hall colonial boasts colonial & art deco architectural details. Moved to its current location in the 1930s NY architect Robert Carrere renovations include generous reception rooms, wide red pine floors, high ceilings, 2 wet bars, 9 wood burning fireplaces. Rotary dial phones, butler bells, & other period details capture the charm of the 1930s. Gourmet kitchen with fireplace custom cabinetry, a fish sink on the back porch for cleaning trout! Elegant sunny dining room & breakfast terrace with herb garden. Sun porch glass doors open to stone walled perennial gardens & pool. Dramatic arches & vaulted ceiling adorn the poolhouse with kitchenette, 1/2 bath, dressing rooms & outdoor shower. Custom oval gunite heated pool. Main bedroom with private sitting area, fireplace & steam shower, 3 large ensuite bedrooms with fireplaces, playroom and laundry on upper floor. Ensuite studio above heated garage. Ownership includes all benefits of hunting, fishing, boating, hiking in this private community on pristine lake & pond. Available caretaking service make maintaining this beautiful home stress free. Enjoy year round peaceful lake area living on unique private estate in gorgeous Doolittle Lake Woods located 2 1/2 hours from Boston or NY. Agent Owned.

NEW CONSTRUCTION!! Don't miss this once in a lifetime opportunity to build your DREAM home in the picturesque town of New Hartford by one of Litchfield County's leading luxury home builders. Fresh, timeless, custom crafted. Beautiful, energy efficient, 4 bedroom/3 1/2 bath/3 car garage, custom built Farmhouse with knock-your-socks-off primary bedroom suite on 1st floor. 2 + glorious acres at end of a quiet cul-de-sac in a lovely, sought after, neighborhood. Spacious, light filled home is the perfect spot for hosting holiday events, family gatherings and more! Exquisitely appointed, home boast luxury, meticulous style and unparalleled craftsmanship in every detail. Chef's kitchen with expansive center island open to a sunny dining area and great room with cathedral ceiling, gas log fireplace and sliders to an enormous open porch/back patio. Marvin windows, solid core doors, gorgeous hardwood floors throughout. Cathedral and 9 foot ceilings on 1st floor and private office tucked away behind the chef's kitchen. Upstairs you will find a fantastic loft and 3 additional good sized bedrooms and 2 full baths. Enormous expansion potential with space that could be a media/exercise room over a huge 3 car garage. Construction has not yet started so there is plenty of time to make it your own! Whatever is on your wish list this sun filled, gorgeous 2+ acre home site is your canvas. Minutes to town center, shops, fine dining, Farmington River, Ski Sundown. Still time to choose EVERYTHING!

NEW CONSTRUCTION! GORGEOUS, TRADITIONAL FARM HOUSE COLONIAL TO BE BUILT on private 2+ acre lot in New Hartford at the end of a quiet cul-de-sac. +/- 2675 SF, 4 Bedrooms, 2 1/2 Baths, additional Game Room over 2 Car Attached Garage. This one has it all. Open floor plan that has great flow is an entertainer's dream. Spacious, energy efficient sunlit home with oversized windows to be built to the highest quality standards. Featuring nine foot ceilings on the first floor, natural hardwood floors, beautiful millwork and trim detail. Stunning chef's kitchen with WHITE cabinetry opens to light and bright breakfast room and nice sized family room perfect for hosting holiday events, family gatherings and more. Relax and unwind in your luxurious Primary Bedroom suite with large walk-in closet, spa-like primary bath and European tile shower, granite tops and double sinks. Upstairs laundry, sparkling white hall bath and three additional good sized bedrooms AND game room complete the upstairs. Exterior features low maintenance vinyl clapboard siding for a classic, New England look. Hiking, biking and Farmington River just minutes away. Great location in close proximity to Bradley International Airport and Ski Sundown. All renderings and photos are of homes built by the custom builder. CUSTOMIZE THE FLOOR PLAN & BUILD YOUR DREAM HOME! Whatever is on your wish list, this sun filled, gorgeous 2+ acre home site is your canvas. Time to choose everything!

Escape to the hills! This is a rare opportunity to own a unique, 87 acre property in the foothills of Litchfield County. Possible subdivide. The property, graced by an antique Colonial home built in 1838, offers stunning views, meandering stone walls, an apple orchard, open fields and beautiful woodlands. Home features large sun porch, living room, 4 bedrooms, kitchen area, upstairs family room, 2 full baths, antique hardwood wide board floors and 3 fireplaces. If you are a craftsman or handy looking for an opportunity to put some hard work in to bring this historic home back to life, this place is certainly a diamond in the rough with so much potential. The home has an outdoor wood burning home heating/hot water system installed under a town approved special permit- not easy to obtain. In these uncertain times, having near free heat and hot water is comforting. Living off the land can be obtained from gardening and hunting if desired. The mixed-use property has several possible sources of income, with two town approved businesses including woodworking shop and firewood business. Property has highly valued red oak timber that can also be used as source of income. Superb location in close proximity to Bradley International airport and Ski Sundown. If you are looking for privacy with beautiful surroundings – this is the one. Don't miss this great opportunity!

This quintessential country property is what everyone wants. Located in the Southern Berkshires close to the towns of Great Barrington, New Marlborough and Southfield and Norfolk, CT. This sleek historic and beautifully restored home is conveniently located for skiing, hiking, arts and culture, restaurants and all other Berkshire offerings. This home is beautifully restored and includes a stunning 'party ' barn, and separate garage/storage shed. The house glows, filled with light and sun. A large living room with fireplace and several seating areas has views to fields and flowers. A cook's kitchen with a counter-height fireplace looks out onto a stone patio with fire pit. The library, tv/ media room and powder room complete the 1st floor. Four.bedrooms, 2.5 baths. Restored barn.

NEW CONSTRUCTION! TO BE BUILT. Gorgeous 2675 SF Farmhouse Colonial, 4 Bedrooms w Upstairs Game Room, 2 1/2 Baths, attached 2 car garage on private, level nearly 4 acre lot on beautiful cul-de-sac. GREAT neighborhood. Open floor plan is an entertainer's dream. Spacious, energy efficient sunlit home with oversized windows built to the highest quality standards. Featuring 9 foot ceilings on 1st floor and natural hardwood floors on entire 1st floor and upstairs hallway. Stunning chef's kitchen with white cabinetry opens to a sunny breakfast room and nice sized family room perfect for hosting holiday events, family gatherings and more. Relax and unwind in the luxurious Master Bedroom suite with huge walk-in closet, spa-like bath with Euro tile shower, granite tops and double sinks. Upstairs laundry room, sparkling white hall bath, 3 additional good sized bedrooms and rarely available exercise/media/game room complete the upstairs. High end finishes. Master craftsmanship. Attention to detail. Exterior features low maintenance vinyl clapboard siding for a classic, New England look. Hiking, biking & waterfalls at Enders State Forest just minutes away. Superb location in close proximity to Bradley International airport & Ski Sundown. All renderings & photos are of homes Brook View Developers built. CUSTOMIZE THE FLOOR PLAN! BUILD THE DREAM! Whatever is on your wish list, this sun filled, glorious nearly 4 acre home site is your canvas. Still TIME to choose everything!

Discover the perfect blend of contemporary style and natural beauty in this newly renovated riverfront home. With 1,600 square feet of living space, this residence features three bedrooms and two brand-new bathrooms. The hip, newly renovated kitchen is a true design statement and now opens to the great room, with its high ceilings and large windows that fill the space with natural light. The kitchen's Classic Retro appliances, including a 24'' gas range with convection oven and an energy-efficient refrigerator with LED lighting, add a touch of iconic nostalgia with modern functionality. White quartz countertops complete the sleek look. This riverfront retreat reimagines modern living with style and serenity. The great room's wood-burning fireplace, and the home's new high-efficiency hot water hydronic heating system ensures cozy winters, while mini-split air source heat pumps keep things cool in summer. The newly finished lower level offers a versatile walk-out family room, and an additional living area. The new baths include a walk-in shower on the first floor and a soaking tub on the second. Outside, the property features 136 feet of Clam River frontage, with the option to expand to 500 feet with the purchase of additional land. The 1.26-acre lot includes open lawn, a deck for outdoor relaxation or entertaining, and direct river access for summer fun. Located in peaceful Sandisfield, MA, this home is near cultural amenities like Jacob's Pillow and Tanglewood, offering both tranquility and convenience. An abundance of hiking trails, state forests, lakes and rivers are throughout Sandisfield and its neighboring towns.

Nestled in the picturesque landscape of Litchfield County, this extraordinary Contemporary Home offers a blend of natural beauty and refined craftsmanship. A stunning vaulted entryway sets the tone for the elegance found throughout. The well-appointed kitchen features large central island, craftsmanship cabinetry, stainless steel appliances, farmhouse sink, additional prep sink and amenities fit for a cooking enthusiast. Adjacent to the kitchen is a dining area with full glass doors to the outside wrap-around deck. Every window throughout the home frames the wooded beauty, bringing the outdoors inside. A few steps down lead to the sunken living room with cozy fireplace. The home also features a beautiful stone fireplaced family/entertainment room on the main level. The primary bedroom suite is a sanctuary unto itself, highlighted by a vaulted wood ceiling and loft area with private outdoor deck. The bathroom boasts double sinks, a spacious walk-in shower and heated towel rack. A spiral staircase leads to a sunroom retreat which is also accessed from the family room. The property includes a total of 4 garage bays. The lower level basement presents a blank canvas for expanded living space or storage providing an additional 2015 square feet. This home exemplifies a harmonious blend of sophistication and comfort within a highly desirable neighborhood. Don't miss the opportunity to experience the serenity and luxury of this exceptional residence.

Discover waterfront living in this stunning contemporary residence, boasting an idyllic setting with direct lake access. Step inside to find an open-concept main level, where the kitchen, dining room and family room converge into an entertainer's dream. There is an additional family room with a wood burning fireplace on the main level. Transition effortlessly to the outdoors where the expansive lake view deck awaits. A hot tub offers a private oasis to unwind under the stars, framed by the tranquil sounds of the water's edge. Ascend to the second level where the primary bedroom serves as a personal retreat, complete with an ensuite bath designed for pampering. Two additional bedrooms offer comfort for family and guests, while a versatile bonus room provides space for your lifestyle needs.

On the crest of Woodruff Mountain, moments from The Southfield Store, York Lake, and area amenities, a classic country estate awaits. Its centerpiece is a stately 5BR, 5000sf, c. 1798, Georgian-Federal home, set on a 232-acre property encompassing a 3,550sf historic barn, smaller barns & run-ins, gardens & green house, Gunite pool & pool house, tennis court, fields, pastures, stream, mile-long trail abutting Sandisfield State Forest, and 5-acre spring-fed pond, all arranged for maximum livability and delight. You'll be pleased with the elevator, generator, & other mod cons, and charmed by historic details, stunning vistas, & untrammeled view of the star-studded night sky. Not enough? A 6,000sf guest house with four apartments suggests myriad uses for guests or income. Perfectly beautiful. The origins of East Hill Farm date to the 1740s, when New Marlborough was first settled, and Thomas Shepard came from Cambridge, Massachusetts, to establishe a home in Southfield. In 1798, he built a grander residence signifying his prosperity and stature in the community. Shepard's new home boasted a facade and interior details in the latest neoclassical style, eight rooms including four bedrooms, five fireplaces, and expansive views across pasture and fields to the south. Now on the market for the first time in 55 years, East Hill Farm awaits a new steward to write a new chapter in its rich history. Throughout its 226-years, the now 232-acre property has been enhanced and adapted to meet the needs and wishes of many generations. The property's new owner will benefit from a classic vision of what a gracious country home should be, with tennis court, Gunite swimming pool, pool house, green house, spring-fed pond and streams, historic three-story barn, two smaller barns, woodlands and trails, perennial gardens, pastures, run-in sheds, and an expansive guest house with four apartments and totaling nine bedrooms. A three-bedroom caretaker's house, set on five acres, though not part of this listing, is being offered separately to the buyer of East Hill Farm. Classic, too, is the landscape design: gardens near the house lead the eye to pasture, hedgerow, and pond, and, beyond that, to a distant west view. Sight lines are punctuated by towering sugar maples, stone walls. The property abuts both Sandisfield State Forest and New Marlborough Land Trust acreage, connecting the two. About 2.5 hours drive from New York and Boston and 60 minutes from Bradley International Airport, East Hill Farm offers privacy as well as unparalleled access to culinary, recreational, and cultural amenities, including Sandisfield State Forest, York Lake, 1,000-acre Pond, Southfield Store, Old Inn on the Green, Butternut ski resort, and Great Barrington's shops, restaurants, and performance venues. Tanglewood, five Equity theaters, Jacob's Pillow Dance Festival, and amenities in northwest Connecticut are within easy reach. New Marlborough is a low-tax town of artists, writers, craftspeople, and second-home owners, attracted by its laid-back, sophisticated rural atmosphere. Its meeting house is the venue for the Music & More series and exhibits by painters, sculptors, ceramicists, and photographers, while its village green is the setting for a vibrant Saturday morning farmers' market. The Thomas Shepard House Listed in the National Register of Historic Places, the Thomas Shepard House was built by Connecticut housewright John Collar who did many homes in the southern Berkshires; one of his design trademarks was the creation of passages and closets next to the chimneys between rooms. In 1798, the Georgian architectural style was transitioning into the lighter, brighter Federal fashion; for instance, the home's fireplace surrounds feature both Georgian bolection moldings and Federal mantels. One unique detail is its enclosed staircase, which is thought to be original and reflect an early use of the house as a meeting place for a progressive Christian community. Subsequent owners have honored the home's original features: millwork and chair rails, chimney cupboards, hardware, wide-board flooring with original T-nails, the dining room's cooking fireplace with oversized beehive oven, and 12-over-12 window sash crafted of dense, durable first-growth wood, containing hand-blown 18th-century glass, and fitted with storms for maximum R-value. Subsequent owners have also added features for comfortable modern living. In the 1930s, a rear ell was added. The sellers enlarged this, bringing the home's size to an estimated 5,000sf and allowing for radiant heat, modernized kitchen, five bathrooms, large mudroom with laundry, family room with kitchenette and full bath, four-car garage, plus a second-floor sunroom, library, and additional bedroom. An elevator connects the library to the family room, a generator keeps things running whatever the weather, and the basement incorporates a wine cellar. The home's cedar shake roof was put on in 2021, there is high-speed Internet, a security system, a drilled well, and the heating fuel is oil. The National Register report is available upon request. Lifestyle Amenities On the north side of East Hill Road, the current owners created a tennis court, 20'x40' Gunite swimming pool, pool house, greenhouse, and 1,960sf barn. Behind it, a mile-long woodland loop road connects the main compound with the guest house to the east and pond to the west. Just west of the home's roofed flagstone patio and ancient apple tree, parterre gardens brim with perennials, annuals, and herbs, blueberry bushes, irises, peonies, and heritage roses. A picturesque 280sf garden shed provides a sweet focal point there, while a broad, mowed path leads to a stone wall and rustic gate, pasture, large spring-fed pond, estimated to be five acres in size for boating, fishing, and swimming. On the road's south side are pastures and woodlands, a stream with charming footbridge, and two barns. The current owners brought in a three-story, 3,550sf, 18th-century barn, dismantled in Vermont and reconstructed on site; this contains a number of large bays and two work rooms. They also built a smaller barn near the stream. Each of the pastures has a water source. In addition, there are two run-in sheds with electricity and running water, and three utility sheds. A portion of the property is in Massachusetts Chapter 61A, which provides for reduced taxes on agricultural properties. The Guest House The guest house is a 6,000sf structure, built in the 1930s as a barn for Arabian horses. Reimagined circa 1990, it contains four duplex apartments, each with radiant heat, independent exterior entrance, living/dining room with fireplace and cathedral ceiling, workable kitchen, first- and second-floor baths, generous closet space, and garage and storage space. It has a new oil/wood furnace, a fire security system, and a shared laundry room off the hallway that connects the apartments to the garage. Apartment 1: Spacious first-floor living/dining room with fireplace and French doors opening to a large, private terrace, den with built-ins, full bath; kitchen, and gracious good-morning staircase leading to the upper floor, which has three bedrooms with one en suite and one shared bath. Apartment 2: Spacious first-floor living/dining room with fireplace and doors onto a large, private terrace, den with built-ins, half bath, and kitchen, and staircase leading to two bedrooms with shared bath. Apartment 3: Spacious first-floor living/dining room with fireplace and French doors to the lawn, den with built-ins, kitchen, half bath, and staircase leading to the two bedrooms and shared bath on the second floor. Apartment 4: Spacious first-floor living/dining room with fireplace and built-ins, den with built in shelving, full bath with claw-foot tub, kitchen, and staircase to two bedrooms and shared bath on the second floor.

Location! Collinsville home with Farmington River views! Life is good when you can walk to shops, cafes, the farmers market, rail-trail and the river. Updated windows, 2 full baths, and peaceful water views through the trees to enjoy from your deck. Just a little bit of love and attention will go a long way to make this adorable village home all your own!

A Charming Colonial with Scenic Views Welcome to this beautifully maintained 8-room colonial, a perfect blend of comfort and convenience, nestled on a picturesque corner lot. This inviting home offers a spectacular newly renovated kitchen, 4 bedrooms and 2.5 baths. a spacious living room that opens to a generous deck perfect for enjoying the quiet surroundings and open views.

Estate Sale. Ideally sited on top of the hill on 3.5 acres in the northwest corner of Litchfield County in Harwinton sits this one-of-a-kind stone/ranch home. Features of this unique home include a great room/living room with cathedral ceiling, wood burning fireplace and hardwood flooring; kitchen with dining area and cathedral ceiling; primary bedroom with wood burning fireplace, full bath and wall to wall carpeting; two guest bedrooms and a full bath. A two car garage is under this fine home along with a detached garage/workshop. Bring your creativity and updating ideas to transform this special home into your magical dream home. Enjoy all that Harwinton and Litchfield County has to offer including the local fair, area golfing and horseback riding. Easy commuting to Hartford County and beyond within close proximity to Routes 118, 4 and 8.

Perched atop a gentle hill on a sprawling 1.3 acre lot, this classic brick Cape Cod home exudes traditional charm and solid construction. The residence welcomes you with a cozy kitchen featuring a quaint breakfast nook, perfect for savoring morning coffee. A convenient mudroom keeps daily clutter at bay, while the formal dining room and living room beckon with their warm hardwood floors, setting the stage for memorable gatherings. The main level features two comfortable bedrooms with hardwood flooring, serviced by a full bath, ensuring comfort and ease of living. Ascend to the upper level to discover a versatile primary bedroom, complete with a sitting room or office space, and an additional full bath, providing a private retreat within the home. The partially finished lower level has a rustic bath with shower and ample storage space for all of life's extras. Step outside to the private deck , an ideal haven for relaxation or entertaining amidst the backdrop of your own private grounds, complete with a handy storage shed. A detached two-car garage sits at the end of the driveway, offering both convenience and utility. Located in an ideal spot for easy commuting to the towns of Litchfield and Torrington, this home is a gateway to the region's abundant outdoor activities, including hiking, golfing, swimming horseback riding and tennis. Embrace the opportunity to own a slice of serenity with this well-crafted home, where tradition meets an active lifestyle.