Introducing 444 Pomeroy Ave, a true neighborhood icon! This one ticks all the boxes: Curb appeal to the max with mature perennial plantings, gracious front yard, private side yard with hot tub, and the true star of the show--the screened porch, which you won't want to leave in the summer. The home is spacious with a cooks kitchen and dining room, ample fire placed living room w/ built-ins galore. First floor 1/2 bath, & period details & charm that cannot be replicated today. Upstairs, 3 sizable bedrooms, & a fully renovated bathroom w/ Italian marble counters, tiled walk-in shower & radiant heat. The partially finished lower level features another bedroom for extended family and guests. A large two car garage was added, with exceptional loft storage space above. Be ready to fall in love!

Welcome to 99 Buxton Hill, a beautifully renovated home nestled on a tranquil cul-de-sac street in one of Williamstown's most sought-after neighborhoods. Thoughtfully renovated throughout in 2015, the home features new windows, a new heating system, a new roof, a stunning kitchen, renovated baths, cathedral ceilings and hardwood flooring. A new deck adds to the home's appeal, providing an inviting space to enjoy the peaceful surroundings. Combining modern updates with a welcoming setting, this exceptional property offers the opportunity to enjoy the best of Williamstown living in a quiet and desirable location.

Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full bath. This is perfect for a multi generational family. The basement has plenty of storage and a dry, carpeted rec room with a wet bar and a half bath. The grounds feature mature landscaping and privacy. The roof, skylights, and gas fireplace are newer (installed in 2016). Home is on a private street with a cul-de-sac and is within walking distance to BCC and the state forest. Bosquet and Jiminy Pe

Thoughtfully crafted custom home offering timeless New England character, quality craftmanship, and beautiful eastern mountain views. Rich natural woodwork and exposed beams create a warm, inviting atmosphere throughout. The custom kitchen with granite, marble and butcher block countertops opens to the dining area with French doors leading to a screened in sunroom. Enjoy the expansive deck, stone patio with firepit, and beautifully landscaped grounds. Spacious living and family rooms with woodburning fireplace and generous mudroom/office. Offering three bedrooms, three baths, plus a versatile creative space, studio/sitting room, endless possibilities. Minutes to downtown Lee, Stockbridge, Lenox, Tanglewood, shopping, dining and all that the Berkshires has to offer for year-round living.

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 to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals--just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train.

Brand new, never occupied, pristine new build on over 4 acres in beautiful Sandisfield. This home was built with a keen eye for detail and a focus on beautiful finishes and materials that harmonize with the landscape. Bright, airy, and filled with positive energy, the space invites you in and makes you feel right at home. There are soaring ceilings in the great room and a cozy gas fireplace, which leads to a stone patio overlooking the peaceful woodland setting. A cook's kitchen with stunning marble counters, stainless steel appliances and a walk through pantry will awaken your inner chef. Each floor has a full bath, providing options for a first floor bedroom if so desired. Upstairs, there is a large loft space with tons of light, and a lovely primary bedroom with luxurious ensuite

Originally built in the 19th century, this Egremont schoolhouse has undergone a radical,''down-to-the-studs'' transformation, and has been thoughtfully designed to create a high-performance home for modern living, while honoring its historic character. Sound structural integrity, with state of the art insulation, custom engineered windows, a new HVAC system, and a solar array for near zero energy overhead make this home immensely comfortable and sustainable for decades to come. The Great Room features dramatic vaulted ceilings anchored by original exposed beams and a new, high-efficiency propane free standing stove. The chef's kitchen has custom cabinetry topped with honed marble counters. The bath features custom tile work and radiant heated floors.

Steeped in history and rich with character, this remarkable 1767 residence is the oldest home still standing on its original site in Williamstown.Thoughtfully expanded over time, it preserves its historic integrity while offering comfort for modern living.Set on nearly five meticulously maintained acres in one of the town's most desirable neighborhoods, the property feels both private and timeless, with mature plantings, perennial gardens, and sweeping lawns.The classic Cape Cod-style architecture features a wood shake roof, enhancing its New England charm. Inside are 5 bedrooms and 3.5 baths, blending intimate period rooms with light-filled living spaces. A dramatic living room with cathedral ceilings and French doors opens to beautiful Goshen stone patios, ideal for outdoor entertaining.

Uncommonly Superb View -- A Vermont Meadow Retreat Tucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival, privacy, and permanence that is difficult to replicate. The architect designed home blends natural materials inside and out, offering a calming, organic environment that feels inseparable from the land around it. One of the sellers' guiding goals the architect skillfully interpreted, was harmony with the landscape, expressed most beautifully in the roofline: ... (see more)

Fabulous historic church. Located in the Stockbridge hamlet of Interlaken. Quiet and exclusive neighborhood just off Rt.183. Stylishly decorated by a renowned architect and designer. High ceilings, huge windows, and mahogany fittings. Beautifully restored kitchen with many original details. Marble topped sink/counter. Walk through to the magnificent living area to step back in time to an earlier era. Then on to the nave to enjoy soaring ceilings, oversized windows and room for entertaining. Enjoy this 'party space.' Or use for an artist studio, recording studio or any pastime that needs space. Minutes to Berkshire Botanical Garden, Tanglewood and the center of Historic Stockbridge.

Originally a gift from Williams College President Harry A. Garfield, the son of United States President James Garfield, to his daughter, this elegant and gracious South Street home is available for the first time in over thirty years. Fine architectural details abound with beautiful crown moldings and woodwork, six panel doors, gleaming oak flooring, abundant built-in shelving and cabinetry, and large, light-filled floor-to-ceiling windows. The spacious entrance hall opens on your left to a stunning wood-paneled library lined with ample book-shelving and warmed by a corner fireplace with wood mantel and slate hearth. Ahead, the lovely living room, with another handsome fireplace with decorative mantel, side pilasters and marble hearth, provides access to a covered slate side terrace.

CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2 car garage completes the first floor. The second floor offers 3 addition bedrooms, full bath, built-in bookcase with window seat. Kick back and relax on the front porch! A fabulous Berkshire house close to all Berkshire cultural venues, skiing, shopping, restaurants and, just plain fun!

Just outside the charming village of South Egremont, this thoughtfully designed home offers three levels of beautifully finished living. An open plan blends formal and informal spaces with gleaming wood floors, a chef's kitchen and a first-floor primary suite. Spacious living and family rooms offer wonderful spaces for gathering and entertaining. a lovely front porch and screened porch and listen to the babbling brook for relaxed Berkshire evenings or morning coffee. Upstairs offers two bedrooms, a full bath and versatile bonus rooms. The walkout lower level provides private guest or in-law quarters with its own kitchen, bedroom and bath. Walk to The Old Mill and enjoy Great Barrington and Sheffield just minutes away. Egremont with low taxes and close to all Berkshire County attractions.

Just beyond New Marlborough Village this architectural gem showcases 5,653 square feet of superior craftsmanship along the Umpachene River. Built in 1989, this 5-bedroom home was designed by internationally renowned architect Paul Bierman-Lytle, a pioneer in sustainable development and healthy home design known for championing non-toxic climate adaptive building materials. Distinctive circular towers, curved walls, arched windows and premium natural finishes harmonize with the surrounding natural landscape. The grand foyer opens to an expansive kitchen, living, & dining space anchored by a striking Finnish soapstone wood stove and marble fireplace. A sun-filled breakfast room leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment.

Perfetto. A pebbled, willow-shaded drive welcomes you to a classical villa elegantly and privately set in a coveted location minutes from Great Barrington. Taking design cues from ancient Rome and built to exacting standards, its light filled interiors yield fully protected views of fields, meadows and mountains. Sophisticated details and quality craftsmanship are everywhere evident--19 sets of French doors for ideal indoor-outdoor flow, varied ceiling heights, living room with custom mantel, serene primary suite, guest wing, central courtyard with formal gardens and reflecting pool, pergola and lap pool, and chef-ready kitchen, central AC, and generator. Privacy, ease, and expansive views, all in a 2,716-square-foot sanctuary on Baldwin Hill.

A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is more than a residence, it is an irreplaceable American landmark

Set on 30 private acres bordering Beartown State Forest, this exceptional Berkshire estate offers a rare combination of timeless farmhouse architecture, refined craftsmanship, and complete privacy. Built in 2018, the 4,700-square-foot residence is thoughtfully designed to blend seamlessly into its surroundings, creating a home that feels both elegant and deeply connected to the landscape. Filled with natural light and beautifully proportioned throughout, the home offers four bedrooms, five bathrooms, and inviting spaces designed for both everyday living and effortless entertaining. At the heart of the home, the chef's kitchen features Vermont Danby marble countertops, a spacious pantry, and an inviting breakfast nook that opens to the surrounding gathering spaces.

Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with an en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An oversized three-car garage and finished lower level provide ample storage, while expansive windows showcase the surrounding landscape. Just down the road from Tanglewood and close to downtown Lenox and Stockbridge, the location is ideal for enjoying the best of the Berkshires. Available furnished, this exceptional property is move-in ready and an ideal Berkshire retreat.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury. MORE

SUN DRENCHED MODERN HOME WITH POOL AND PRIVACY, ON ONE OF THE MOST COVETED ROADS IN THE BERKSHIRES. This gorgeous property consists of 2 separate lots and sits on the loveliest quiet road ideal for walking and biking, and only 7 minutes drive to Guido's. The house, which has been recently completely reimagined and added onto, is an ode to sophistication, beauty, and practicality. 4+ bedrooms, 3.5 baths, Open plan sun filled kitchen/dining/living, walk in pantry, generous entry with built in benches and storage, TV room with custom shelving, bright office, and a loft like studio above the 3 car garage. For outdoor living, the mahogany deck runs along the back of the house and connects to a comfortable screened porch with plenty of room for dining and lounging. A welcoming family retreat!