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FAIRGROUND REAL ESTATE, INC

Wooded Rural building site minutes away from Otis center; close to Skiing, Resturants, and more. This 2 acre lot is a fresh slate to build a small Cabin or country getaway; Great area to catch nature all around you. Stone walls that boarder the property will ensure your boundry lines and privacy from neighboring lots. Maintained road with no assoication fee, enjoy all the peace and quiet the Berkshires has to offer!


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BISHOP WEST REAL ESTATE

Discover the possibilities nestled in the heart of the Berkshires--just 20 minutes from the charm and culture of Great Barrington. This picturesque lot offers a rare combination of natural beauty and practical readiness, with a completed perc test and engineered septic designs already in place. Whether you're envisioning a peaceful weekend escape or a cozy, year-round haven, this is the perfect canvas to bring your plans to life. Surrounded by rolling hills, quiet woodlands, and nearby attractions, you'll enjoy the best of both serenity and convenience in one of New England's most beloved regions.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Discover the perfect blend of tranquility and convenience with this exceptional cleared building lot in a picturesque country setting. Boasting seasonal views and situated within a peaceful association of beautiful homes, this property is an ideal getaway spot for your dream country home.With a drilled well and a leach field for a 3-bedroom septic system installed within the last three years, you can build with confidence knowing the essential infrastructure is already in place. Stay connected with high-speed internet available through fiber optics, ensuring modern convenience in your serene retreat.Just a 20-minute drive from the vibrant town of Great Barrington, you'll have easy access to shopping, dining, & cultural attractions while enjoying the peace and quiet of the countryside.


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BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD
$289,000
4 BD | 4 BA
Multi-Family

Great owner occupied opportunity- as one apartment is vacant or add to your portfolio and rent all 3 apartments.This well maintained property offers a beautiful setting and many updates such as a NEW septic system 2012, blown in insulation 2013, NEW vinyl siding and windows 2020, New water filter system 2019, New water heaters from 2019-2021 and blown in insulation 2013 to name a few. 3 CAR DETACHED GARAGE!!!!! 48hour notice with all appointments.


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LANCE VERMEULEN RE, INC
$499,000
3 BD | 1 BA
Residential - Single Family

Rustic Contemporary in Otis Wood Lands that abuts the State Forest! This great home has an open concept kitchen/living/dining area with vaulted ceilings. Access the screened-in porch and deck from the sunken living room. Primary bedroom with skylight and deck access. Detached two-car garage with storage above. This great house won't last long! Association amenities include tennis/pickleball courts, pool, fitness room, clubhouse, playground, lake and beach area. $4,000 reserve fund fee due from buyer at closing. Wood stove disconnected prior to closing.


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HELEN MULLANY REAL ESTATE, LLC
$515,000
3 BD | 2 BA
Residential - Single Family

Experience the tranquility of Sandisfield--surrounded by lakes, trails, and natural beauty--just minutes from Great Barrington, Lee, and NW Connecticut, and a little over 2 hours from Boston or NYC. This beautifully renovated 1843 Greek Revival home blends historic charm with modern comfort: 3 bedrooms, 2 updated baths, and a bright open-concept kitchen/dining/family room with marble counters, new appliances, and A/C. Enjoy peace of mind with a 50-year metal roof, new insulation, and updated electrical. A classic red Bank Barn offers studio/workshop potential. Just 6 minutes to the Farmington River General Store and close to skiing, fine dining, and top Berkshire attractions.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$595,000
4 BD | 2 BA
Residential - Single Family

HISTORIC JABEZ BOSWORTH INN & TAVERN: AUTHENTIC BERKSHIRE COUNTRY LIVINGSet quietly in the heart of Sandisfield, Massachusetts, the historic Jabez Bosworth House & Inn, circa 1798, offers a genuinely rare opportunity to own an iconic piece of New England history just 14 miles from the vibrant town of Great Barrington. Originally home to Revolutionary War Captain Jabez Bosworth, this Federal-style home once served as a welcoming stagecoach inn on the Hartford-to-Albany route. The expansive living room stretching the width of the home, features a wood-burning fireplace, and provides an open palette to make the home your own. A thoughtfully designed country kitchen includes a charming breakfast nook with window seats overlooking the picturesque meadow.


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LANCE VERMEULEN RE, INC
$595,000
3 BD | 3 BA
Residential - Single Family

This beautiful 3-bed, 3-bath contemporary home in the Otis Wood Lands offers modern comforts in a serene setting. This property boasts a screen porch, sun deck, and 2 wood burning fireplaces! The sunlit great room, with floor-to-ceiling windows, is perfect for entertaining with it's open concept living room, dining room, and kitchen area. The primary suite features a wood burning fireplace, walk-in closet, and en suite bath with walk-in shower. Down the hall you'll discover bedroom #2, a full bath, office/bonus room and bedroom #3, which includes its own en suite bath and 2 closets. OWL offers fantastic amenities: a lake, sandy beach, heated pool, fitness center, 4 tennis courts, 2 pickleball courts, a playground, trails, and a clubhouse. $4,000 reserve fund fee due from buyer at closing.


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RE/MAX COMPASS
$599,000
4 BD | 3 BA
Residential - Single Family

The property is ideal for active families (with tennis and basketball on site and swimming and hiking minutes away). A quicker, more traffic free, less fussy destination than the Hamptons and tons and tons of space and fresh air! The home is just about 15 minutes from affordable family skiing and about 30 minutes from world class music at Tanglewood and dance at Jacob's Pillow. Excellent dining (both upscale and casual family friendly options) are nearby in Great Barrington. The home is also set up as a rental with a reliable efficient team in place to help offset a significant amount of carrying costs. A year round easily accessible destination to make family memories that will last a lifetime!


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COMPASS MASSACHUSETTS , LLC GB
$825,000
4 BD | 3 BA
Residential - Single Family

VIEWS! VIEWS! VIEWS! Built in 1923, this home with stunning views brings a blend of yesteryear's charm with todays modern expectations. Set in a private location on 15 acres of natural beauty with a running brook and outbuildings that have boundless possibilities, this is the country escape most people dream of. The original home with its wide plank flooring, stone fireplace and three cosy bedrooms brings you back in time, but now with high speed internet and forced hot air! The newer addition in 2017 is bright and airy bringing a seamless transition from the old to the new with stainless steel appliances and marble accents. A kitchen/dining area with a wood burning fireplace, primary bedroom, an office space and first floor full bath completed this extension.


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LANCE VERMEULEN RE, INC
$1,145,000
3 BD | 2 BA
Residential - Single Family

Welcome to a place to gather, unwind and recharge. Just 5 minutes from the heart of Monterey, this serene property spans over 13 acres of peaceful woodlands at the end of a quiet country road, providing a true haven for family and friends. Surrounded by perennial gardens, a natural pond, and an expansive forest, this home embraces both indoor and outdoor living. The Great Room is perfect for gatherings and features a grand stone fireplace, a cozy sleeping loft and a wall of windows and doors that lead to a stone patio. A second, more intimate living area with its own fireplace and exposed beams is situated just off the kitchen and dining room, opening onto a deck and a screened porch. The entire length of the house enjoys westerly views of a lush pond fed by the Buck River.


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BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$4,999,999
3 BD | 6 BA
Residential - Single Family

Atwater Pond is a remarkable 321-acre waterfront retreat in southern Berkshire County. An immaculately renovated mid-century house and 1920's guest cottage sit on the edge of a 32-acre, spring-fed pond, surrounded by hundreds of acres of pristine forest. Year-round recreational opportunities abound and a 4+ mile trail system winds through the property. Additional features include multiple docks, historic boathouse, deep water swimming hole, paddock with run-in shed, Truly the best of both worlds, the property is supremely private, yet conveniently located to take full advantage of everything the Berkshires offer. Boston and New York City can be reached in 2.5 hours or less, Bradley International Airport is only 45 min away. Offered turnkey.