Impressive short term rental history. Enjoy quick access to ALL Berkshire attractions! Don't miss this move-in ready cabin on 1 acre, just a short walk to downtown Great Barrington and Lake Mansfield's lovely beach. Gaze at breathtaking city and distant mountain views from your spacious living room with vaulted ceilings and a stunning free-standing stone gas fireplace. The open kitchen features an eat-in area and deck access for grilling. Enjoy one level living w/ a primary suite on the first floor. A half bath w/laundry completes the main level. Upstairs, two bedrooms boast tall ceilings and windows looking out onto trees & letting in natural light. The bonus loft area has the best view in the house! Ample storage in the partially finished basement and heated two-car garage.

Let's begin with the location which is nestled high in the hills of Spencertown. Some may say it's the crown jewel of Columbia County, given its knockout country charm, quaint town square, ten minute drive to Chatham's well curated main street, and easy access to the Berkshires, skiing and the great outdoors.With the stage set you can now focus on a choice 10-acre setting, graced with boundless mountain views and picture-perfect sunsets, a massive star gazing sky, privacy, peace, quiet, plus a pond and stream. Focus in a bit closer and you now take in the classic, warm, gracious, well built, modern log home paired with a generous, finished three car garage. Upon entering you will be captivated by the stunning stone fireplace, open floor plan with gourmet kitchen, great room

Country Living-private & quiet - Equine Property. Just under 3 private, gated & fenced acres. Beautifully updated & freshly painted this Contemporary Cape Home open floor plan is bright & roomy as kitchen opens up to cathedral ceiling living/dining area w/ wood burning fireplace. 1st floor Primary Bedroom w/ en-suite, 2 story foyer leading up to the spacious 2nd floor bedrooms. Entertain-cooking with Pizza oven in the GREAT Room that includes a kitchen/bar area.Outdoors enjoy the enclosed front porch views or relax in the Hot Tub on the back deck. This property also has an 1800 Sq.ft heated Barn that is meticulous & can be used for anything that suits you, as well as paddocks for Horses, or other loved animals4 miles from center of town, walking distance to State Forest

WELL MAINTAINED FARM HOUSE WITH THE BONUS OF A SEPARATE APARTMENT! Ideal for friends, family or to benefit from rental income. The backyard is an oasis to find peace after a busy day. Extensive perennials, and a beautiful mountain and pasture view.. Simplicity defined when relaxing on the rocking chair front porch. Detached barn and workshop. Close proximity to the Waldorf School, Simon's Rock College, and Main Street Restaurants and Shops. So much potential and plenty of room for home office.

Sunny Contemporary Home with 60' Pool on 1.3 Beautifully Landscaped Acres!Sunlight, privacy, and style. This architect-designed house is exceptionally located in a light-filled lot with a wonderful pool and impeccably kept gardens. This home is move-in ready and allows for one-level living. Relax in the stunning screened porch that overlooks mature gardens and a private backyard. The modern and updated kitchen, with stone countertops opens, marble floor, stainless steel appliances, opens to a spacious living room with fireplace, dining area, vaulted ceilings, skylights, and a large deck. The first floor primary bedroom features an ensuite bath, large soaking tub, skylight, and fireplace.

Enjoy total peace and quiet in a park like setting yet a few minute drive to Main St GB. Property sits high on the hill with mountain views. Perfect flow for entertaining and easy living. 1st floor primary bedroom with en suite bath & jetted tub, central A/C, living room fireplace, screened-in porch off of eat-in kitchen, vaulted ceilings, hardwood floors, and ceramic tiles. New carpeting throughout and a large cedar closet in one of the bedrooms. In-home office with separate entry, large dry basement with high ceilings perfect for in home gym. Insulated garage with long paved driveway. If your looking for a solid newer built home this is it! The average home price in this location is in the million dollar plus range

On a little over 1.6 acres in Southfield, with access to an HOA's private tennis court, pickleball court, and pool, this delightful property has been carefully updated and is turnkey. The stunning screen porch and new terraced stonework anchor the house as a trueindoor/ outdoor Berkshire retreat. Look out over a dramatic gully and stream from yourfarmhouse sink and earthy soapstone counters, with oak floors underfoot. Sit fireside inthe cooler seasons in the living room which has been modernized to incorporate theflow from kitchen to porch, maximizing a sense of space and expanding the footprint of the house to complement its four bedrooms and three full bathrooms, all of which have been redesigned with modern tile workThere is a full basement with separate storage and workshop.

Embrace the timeless elegance of this 1800s antique home nestled in the quaint village of Egremont. Offering a prime location, and situated on nearly 2 acres of lush, manicured grounds, this enchanting property offers a rare opportunity to own a piece of history in a picturesque setting. As you approach the residence, you'll be captivated by its historic charm and character, from the classic architecture to the meticulously maintained perennial beds and apple trees that adorn the landscape. A screened porch provides the perfect vantage point to admire the scenic views, along with the large carriage barn which provides additional storage and space. Inside, the home features 5 bedrooms with multiple inviting living spaces that beckon you to unwind and relax.

Birch Brook Lodge! Own a Piece of History! Exceptional Location on Prestigious Tyringham Road, Immerse yourself in the Charm of this Historic (8) Bedrooms, (3) Kitchens, (4) Full Baths Gem Spanning 3,740 sq. ft., on .96 acres, Cozy Fireplace w/Woodstove Insert, Offering Unparalleled Character and Brook Access and Your Own Clean Private Trout-Stocked Haven! An 1850's Wells Fargo Stagecoach Inn! Embrace Tranquility with Acres of Protected Land. The Carriage Barn Opens Doors to Endless Possibilities, Oversized One Car Garage, Excellent Investment Opportunities for Seasonal Short-Term or Long-Term Rental, Perfect for Family Reunions, Events or Owner Occupied w/In-Law or Rental Income Opportunities, etc., A Timeless Blend of Elegance & History!

Nestled at the end of Brett Rd at the base of bear mountain. This 29-acre parcel includes a charming home with rolling hills, a natural pond, staggered wooded plots leading way to large open hay fields for agriculture or development. The 3-story home includes 3 bedrooms 2 baths. All the bedrooms are downstairs with an island kitchen and large open space on the main floor. The main floor features high ceilings, wood grained walls, slider doors, bay windows and access to wrap around deck. Vast stunning views from the deck feature Bear Mountain all the way to Butter Nut. This property has dual zoning for industrial, commercial residential and agriculture. Property has recently been tested and failed to title 5 Owner acknowledges this is a contingency that shall be addressed prior to closeing

1836 Colonial in the Village of Kinderhook. Set back from the road with a private yard planted with specimen trees and lovely gardens. Freshly painted exterior and interior. Covered rocking porch extra deep for summer nights. Double doors welcome up to a lovely staircase and banister. Double parlors with high ceilings and wonderful detail. Wood burning fireplace. Wood floors throughout. Butler's pantry with original built ins and wainscoting . Perfect for coffee bar, wine bar or plants. New kitchen with handmade Dutch tiles, white cabinetry and great working island. Pantry with new penny tile. Four bedrooms upstairs. Large primary with upstairs balcony perfect for morning coffee. Office and dressing room in primary. Lovely gardens. Post and beam barn. Backs up to preserved land

Welcome to this winery and tasting room located in the beautiful southern Berkshires! This business/farm is located right on Rt 7 which is considered the ultimate New England road trip. Capture tourists year round with nearby Tanglewood, the botanical gardens, Butternut ski resort and so much more! This spacious post and beam building consists mainly of two large rooms both with lofts. One, currently a tasting room with a wrap around loft, floor to ceiling windows for abundant light, a dramatic center staircase and french doors leading to the patio and outdoor space. The second room is currently an event center with loft. The tiled lobby has access to storage and a handicapped bathroom. The opportunity exists to live on site with the attached apartment; kitchen, full bath, small

On these hot summer days you may refresh in your own (heated) in-ground pool, or inside with AC in South Egremont. On a cold winter day, cozy up by the large woodstove in the Great Room of this spotless chalet. With three bedrooms and three full baths, along with extra rooms for sleeping guests, there's plenty of room to fill the house with family and friends. Located in a quiet area, enjoy the peaceful views over the nature pond and the lovely gardens around the house and the planting boxes on the large deck. The porch and deck become a summer living area as the house spills out to them from multiple sliding doors. A terrific house for weekend or year 'round living - convenient to both CT and NY, and currently owned by Bostonians moving to a condo. Call today for a viewing appointment.

C1780 CLASSIC COLONIAL RESIDENCE WITH A SCENIC VIEW OF A QUAINT BERKSHIRES VILLAGE. The Ledgehurst estate sits atop a hill overlooking the village of Monterey. Owned by the Bidwell family, founders of Monterey, and run as a boarding house in the 1900s. Later returned to a private estate with a grand indoor pool surrounded by sliding glass doors, a master bedroom balcony, heated brick floor, bar, grill, and sauna. The original horse barn remains, now filled with classic automobiles, plus a de- tached garage and a home garage. 4 bedrooms, 3.5 baths. Sunny living, dining, and office spaces. Central fireplace. Bucolic setting yet a 2 minute walk to the village and one mile to Lake Garfield. Close to Tanglewood, Jacobs Pillow, theater, art galleries, swimming, boating, hiking, biking and more.

Welcome to Colesbrook Manor, an ash timber frame construction masterpiece set alongside lively Coles Brook on 4.4 acres in the southeastern slopes of Crane Hill. Built in 1984 and solely occupied by joiner, carpenter and Heartwood School (of timber framing and energy-efficient house design) co-founder Andy Inganni, this home takes advantage of the microclimates of its setting and the energy and lifestyle benefits of traditional craftsmanship and construction. Beyond 3 bedrooms and 2 full bathrooms, this home features an expansive open floor plan on its main level, inclusive of a living room, dining room, kitchen, indoor raised garden bed with symbiotic drainage, and a screened entry porch. The split level features an in-law suite with bedroom, bathroom, sauna, and screened back porch.

Incredible Berkshire Mountain Home - Frank Lloyd Wright inspired architecture capturing Berkshire mountain views. Its magical set on a hilltop enveloped in mature landscape, secret gardens with waterfalls and a coy pond surrounding the inground pool. Grandiose two story stone pillared entry welcomes you into the stain glassed door dramatic entry. Notice soaring ceilings, archways curved flooring to the sunken living room with walls of glass framing the beautiful outdoors. Formal dining open to this light filled entry. Central air makes the yearround sunroom perfect for relaxation, pool and bird watching. Thoughtful and easy one level floorplan flows to everyday dining, kitchen and floor to ceiling stone fireplaced family room. Saunter to the stone patio for outside dining, wade in

WATERFRONT on the STOCKBRIDGE BOWLIdyllic Four-Season EscapeDiscover the charm of lakeside living with this captivating cottage nestled on the shores of the beloved Stockbridge Bowl. Situated on a peaceful road, this beautifully kept sanctuary sprawls across a generous lot, culminating in a stretch of private waterfront complete with your own secluded dock.This sweet cottage boasts a significant stretch of lake frontage, offering a personal gateway into a world of natural beauty and calm. The cottage, re-envisioned with care in 2001, strikes the perfect balance between contemporary convenience and classic country allure.Step inside to find

Investment MONEY MAKER! This multi-unit Ultra-Luxe property has been completely transformed. 4 units: Two 1 bed/1 bath, & 2 bed/2 bath plus a separate 3 bed/3 bath residence with a Bed-Stuy loft-like feel with brick, metal and wood accents. Located adjacent to the Barrington Stage Co. any investor will enjoy the 5 month summer residency this theater gives the current owner. New everything, separate utilities, tiled showers, and even a covered 4 bay garage for off-street parking. Looking to expand? Current zoning will allow for up to 3 stories (could be built above the existing garage) of apartment units. Be a pioneer and take control of your future and your legacy. Call today for your private showing.

Idyllic, bright cottage, recently renovated and expanded, situated on an inlet of Lake Garfield. Drop your kayak in the water and be on the lake in minutes, or relax on your private screened porch. This home has so much to offer and was renovated with great thought and attention to detail, with high end finishes throughout.An open floor plan encourages gathering, while adding to the ease of the home. Three bedrooms and a sleeping loft provide ample space for guests, while the cozy feel of the home also makes it a perfect getaway from the hustle and bustle of daily life.To top it off, the property has deeded rights to Lad's beach association, with the opportunity to apply for a boat slip, and access to the sandy beach and swimming.Come see this absolute gem for yourself!

Welcome to Blue Spruce Farm, a magnificent 23-acre estate rich in history and brimming with enchanting features. Nestled in a serene setting, this certified wildlife habitat offers a sanctuary for nature lovers and a retreat from the bustle of everyday life. Enjoy leisurely walks on the maintained trails that meander through the 23 acres, offering tranquil views and a connection with nature. A low-maintenance wild garden of perennial flowers and shrubs produce a kaleidoscope of colors during the spring and summer seasons; a string trimmer allows garden paths to be cleared and plant invasions to be managed with minimal effort.