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Great Barrington, Massachusetts: Country Homes, Houses, and Rural Real Estate

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$3,950,000 250 acres
Long Pond Rd, Great Barrington, MA 01230 - Berkshire County

250 acres Great Barrington, MA

This scenic 56 acre lake and nature sanctuary can be all yours! 250+ acres of pristine water and woods. Round Pond is a private lake only 5 miles from downtown Great Barrington! The park-like setting includes a pure, spring-fed lake, hardwood forest, lovely plantings, nature trails, and sandy beach. Spectacular lake and mountain views! It just doesn't get any better than this.
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$2,395,000 63.6 acres 5 Beds | 5 Baths | 6200 sqft
Monument Valley Road Rd, Great Barrington, MA 01230 - Berkshire County

63.6 acres Great Barrington, MA

Relax & enjoy country life on a secluded 63-acre country estate near Butternut, minutes to Great Barrington village. Pastures, ponds, woods & mature landscaping create the setting for a spacious, comfortable 5-bedroom home with an expansive great room & large kitchen, in-law suite, decks, swimming pond & pool, poolhouse, greenhouse, studio & barn. An idyllic retreat for family, friends & guests!
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$2,250,000 10.19 acres 10000 sqft
325 stockbridge road Rd, Great Barrington, MA 01230 - Berkshire County

10.19 acres Great Barrington, MA

Up scale shopping center on a tripped traffic light with 4 buildings that are sub dividable.Scenic 10+/- acreage with over a quarter mile of river front! Across from major shopping center.Financing available
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$1,975,000 15.3 acres 4 Beds | 5 Baths | 5528 sqft
5 Seekonk Cross Rd, Great Barrington, MA 01230 - Berkshire County

15.3 acres Great Barrington, MA

RARE OPPORTUNITY TO OWN A PIECE OF PARADISE: EXTRAORDINARY VIEWS: A Highly desirable location minutes to the bustling downtown with just over 15 verdant and private acres. A beautifully sited and sun-filled home merging the latest amenities with impeccable design. Panoramic window walls frame the main rooms including the state-of-the-art-kitchen, great room, living room, dining room, and master.
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$1,800,000 225 acres 7099 sqft
685 EGREMONT Rd, Great Barrington, MA 01230 - Berkshire County

225 acres Great Barrington, MA

18 Hole Golf Course. Club house features include 2 dining rooms (seating 250) with fireplace and one bar, office, members room, coat room, two lavatories, a full kitchen and two wood decks off the main level. The lower level features a pro shop, two locker rooms with showers & lavatories. Maintenance building , golf cart building, storage building, utility shed & driving range. Approx. 225 acres.
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$1,800,000 225 acres
685 Egremont Rd, Great Barrington, MA 01230 - Berkshire County

225 acres Great Barrington, MA

Property currently 18 Hole Golf Course but make this your own family compound. Clubhouse has 2 dining rooms with FP & bar, office, members room, coat room, two bathrooms, full kitchen & 2 wood decks off the main level. Lower level with pro shop, 2 locker rooms with showers & bathrooms. Maintenance building, golf cart building, storage building, utility shed & driving range. Approx. 225 acres.
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$1,395,000 3.18 acres 5 Beds | 5 Baths | 3648 sqft
250 Maple Ave, Great Barrington, MA 01230 - Berkshire County

3.18 acres Great Barrington, MA

THIS RARE ANTIQUE HOME IN THE HEART OF GREAT BARRINGTON OFFERS SPACE AND CHARM. 5 BEDROOMS, 4 1/2 BATHS, 3 ORIGINAL FIREPLACES. TWO CLASSIC WELL MAINTAINED BARNS, LOFT SPACE FOR OFFICE/STUDIO. NEW 60 FOOT GUNITE AND GRANITE IN GROUND POOL, 2 BEDROOM GUEST HOUSE. 3 ORIGINAL FIREPLACES.SEASONAL VIEWS OF PROTECTED LAND AND HILLS. ALL THE CHARM THE ERA AND CONVENIENCE OF TOWN. See documents.
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$1,100,000 17.09 acres 3 Beds | 2 Baths | 2380 sqft
920 Main St, Great Barrington, MA 01230 - Berkshire County

17.09 acres Great Barrington, MA

7 Heaven. This stick built, craftsman home is a Garden of Eden with easy access to everything Gt. Barrington. 17 plus pastoral acres, zoned multi use offers a myriad of opportunities for the lucky buyer. Words cannot describe the craftsmanship or the setting. The house just needs to be experienced to understand the love.
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$995,000 2.02 acres 3 Beds | 2 Baths | 2900 sqft
15 Berkshire Heights Rd, Great Barrington, MA 01230 - Berkshire County

2.02 acres Great Barrington, MA

STUNNING CONTEMPORARY + STUDIO/GUEST HOUSE in a premier location on the ''Hill.'' Walking distance to Main Street and Lake Mansfield. Easy, one-level living. Soaring ceilings, great light. All rooms have glass doors to a deck which spans the length of the house. Two car attached garage. The studio/guest house has propane heat and a half bath and is about 800 square feet on two levels.
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$995,000 6.49 acres 3 Beds | 4 Baths
0 & 399 State Rd, Great Barrington, MA 01230 - Berkshire County

6.49 acres Great Barrington, MA

Stunning, meticulously maintained & updated 18th century colonial. Magnificent grounds w/ in-ground gunite pool, apple orchards, pear & cherry trees, & impeccable landscaping w/ mature plantings. State-of-the-art kitchen & beautiful stone fireplaces. Ideally situated 7 minutes from downtown Great Barrington & next to Ski Butternut. Perfect for true relaxation & entertaining your family & friends!
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$890,000 9.45 acres 4 Beds | 3 Baths | 3272 sqft
154 Division St, Great Barrington, MA 01230 - Berkshire County

9.45 acres Great Barrington, MA

Gracious Reproduction Saltbox on nearly 10 acres, Privacy, 5 minutes to downtown GB. Rare indeed. Updated and with wonderful details: crown moldings, 2 fireplaces, huge, classic covered porch facing landscaped gardens with zen like fountain. Ground floor master, great flow and numerous entertainment areas. 2 car attached garage and a charming post and beam red barn. Perfect.
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$829,000 3.73 acres 4 Beds | 3 Baths | 3466 sqft
145 Hurlburt Rd, Great Barrington, MA 01230 - Berkshire County

3.73 acres Great Barrington, MA

French Country house with 4 bedrooms, pool and tennis court.Formal entry from the circular driveway, with marble flooring, a large Den, powder room and renovated Living room. Lots of glass in the kitchen, formal dining room and guest wing. Upstairs is the Master bedroom suite with Jacuzzi room and 2 more guest bedrooms that share a bath.
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$775,000 75.45 acres 7 Beds | 5 Baths | 4604 sqft
11 Ramsdell Rd, Great Barrington, MA 01230 - Berkshire County

75.45 acres Great Barrington, MA

Magical Property. 75+ Acres including Pond, Babbling Brook & HikingTrails. Property abutts Protected Land. Not often does a large property with a romantic setting become available in such a convenient Location. 8 Bedrooms, 41/2 baths. 2 Porches, 3 Bay Garage, plus a very large detached Workshop/Barn..Many Possibilities,Family Campond, Artist, Car Enthusiast, B&B, Retreat Center.
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$749,000 11.31 acres 3 Beds | 2 Baths | 2080 sqft
65 Hurlburt Rd, Great Barrington, MA 01230 - Berkshire County

11.31 acres Great Barrington, MA

SET BACK OFF ONE OF THE FINEST ROADS IN THE BERKSHIRES! Wonderfully private yet mere moments from downtown Great Barrington this chic contemporary offers 3-4 bedrooms on more than 11 acres! The updated interior offers pastoral views of the property's pasture & forest, large deck, a/c, fireplace, swimming pool, 1st floor suite, and an open floor plan for modern living! PRIME LOCATION!
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$729,000 9.64 acres 5 Beds | 3 Baths | 3616 sqft
434 Stockbridge Rd, Great Barrington, MA 01230 - Berkshire County

9.64 acres Great Barrington, MA

This is the ultimate home for family and friends. The Post & Beam Great Room is magnificent with a pool table, bar and fireplace. The entire home is comfortable and cozy, kid friendly with an Art Room and finished Basement. There is a large back Deck for grilling and an amazing screened in Front Porch for relaxing. The house sits on 9+ acres, yet is walking distance to restaurants and shopping.
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$699,000 10 acres 5 Beds | 4 Baths | 4562 sqft
678 Stockbridge Rd, Great Barrington, MA 01230 - Berkshire County

10 acres Great Barrington, MA

Shaker Hill....a quirky rambling farmhouse surrounded by 10 acres of privacy and views of Monument Mountain. This five bedroom, four bath rustic, warm and sunny home has comfortable rooms with a view from almost every window. Two story Great Room with vaulted ceiling, eat-in country kitchen. 400 feet down a level drive, the location is most convenient minutes from Stockbridge & Great Barrington
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$695,000 13.97 acres 20 Beds | 18 Baths | 7130 sqft
304 State Rd, Great Barrington, MA 01230 - Berkshire County

13.97 acres Great Barrington, MA

"Comfortable, clean, quiet and very accommodating." - Tripadvisor review. 17 unit motel located near Ski Butternut with dedicated visitors year after year. This affordable motel has 8 rooms with two queens, 7 rooms with one king, one family suite, an efficiency apartment and three bedroom owner's unit. Buy now to take advantage of the booked summer season!
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$675,000 8 acres 3 Beds | 4 Baths | 2630 sqft
75 Monument Valley Rd, Great Barrington, MA 01230 - Berkshire County

8 acres Great Barrington, MA

Amazing Eastern View over Barberie Pond, Newer Contemporary Cape with beautiful finishes. This home offers an easy care open plan with gleaming wood floors, quartzite counters, cherry cabinets and a first floor master bedroom. The front porch is a place to sit and enjoy the mountain and water view. Few homes of this magnitude and view are available in this price range. Abutting conservation land.
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$665,000 3.97 acres 3 Beds | 3 Baths | 1443 sqft
119 Hurlburt Rd, Great Barrington, MA 01230 - Berkshire County

3.97 acres Great Barrington, MA

Simply Put: This is a WOW of a home! Set very privately on 4+ acres on much-admired Hurlburt Road, it's only five-minutes to our beloved Guido's and all things downtown Great Barrington! Beautifully appointed and refreshed throughout in the last 5 years with highest end choices including super-chef's kitchen goodies...Viking, Bosch and more. For details, see supplement.
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$650,000 58.44 acres
58 Monument Valley Rd, Great Barrington, MA 01230 - Berkshire County

58.44 acres Great Barrington, MA

Great Opportunity|58 Acres of beautiful land with and older house. Gentle sloping with open and mostly wooded. Just a few minutes to Great Barrington, Stockbridge and easy access to all Berkshire amenities.
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$648,000 4.13 acres 4 Beds | 5 Baths | 4129 sqft
348 Long Pond Rd, Great Barrington, MA 01230 - Berkshire County

4.13 acres Great Barrington, MA

HUGE PRICE REDUCTION!! Spacious, elegant contemporary located on quiet country road . Designer lighting and fixtures, open floor plan, soaring ceilings. Includes a private in-law suite with separate entrance, and laundry. Attached three bay garage, expansive deck. Very private 4+ acre lot. Priced well below assessed value. MOTIVATED SELLER.
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$599,000 2.17 acres 5 Beds | 4 Baths | 3560 sqft
16 Squaw Peak Rd, Great Barrington, MA 01230 - Berkshire County

2.17 acres Great Barrington, MA

Fabulous large kitchen w/ dramatic window wall & cherry cabinets in this contemporary home in Great Barrington. The Master suite impresses w/ a huge walk in closet & glass wall facing the moon rise. More space in the finished lower level w/ fireplace & full bath. A Large deck is off the kitchen and the big 2 car garage connects through the mudroom & laundry to a large family room w/ library.
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$595,000 1 acres 2 Beds | 4 Baths | 3300 sqft
924 South Main St, Great Barrington, MA 01230 - Berkshire County

1 acres Great Barrington, MA

Beautiful commercial Colonial building that was updated in 2003 and still has many original details including wood floors, fireplaces, and beams. Prime first-floor spaces offer many possibilities. Second floor consists of two, one-bedroom apartments finished with quality workmanship. Four separate heating and cooling systems.
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$585,000 8.84 acres
129 Hurlburt, Great Barrington, MA 01230 - Berkshire County

8.84 acres Great Barrington, MA

Coveted Hurlburt road land with southern views. Large mostly cleared lot with over 8 acres of total privacy yet only 4 minutes into downtown Great Barrington. An 8 bedroom septic system and a well are installed. The foundation is already poured to start the build out of your dream home. Building design plans are available to qualified buyers.
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$549,000 5.53 acres 3 Beds | 3 Baths | 2523 sqft
5 Squaw Peak Rd, Great Barrington, MA 01230 - Berkshire County

5.53 acres Great Barrington, MA

NEWLY BUILT CAPE on a quiet road convenient to Main Street. More than 5 acres of open lawn and pretty woodlands. The house is light-filled and super energy efficient, with lots of bells and whistles... including a first floor master bedroom suite, and a beautiful kitchen with granite countertops and stainless appliances. A bright, walk-out lower level is partially finished and adds real value.
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$539,000 8.6 acres 5 Beds | 3 Baths | 2688 sqft
37 Lake Buel Rd, Great Barrington, MA 01230 - Berkshire County

8.6 acres Great Barrington, MA

Enjoy the serenity of the Berkshires in this ranch inspired home. Spacious 5 Bedroom, 3 bath house with field stone fireplace. Over 8 acres of sweeping Monument Mountain views, small pond and moments from downtown Great Barrington and Ski Basin. Property includes large two car garage, gardening shed and barn. Long driveway to your own private rustic setting. Excellent rental income.
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$527,900 2.5 acres 4 Beds | 3 Baths | 2554 sqft
1 Squaw Peak Rd, Great Barrington, MA 01230 - Berkshire County

2.5 acres Great Barrington, MA

Custom built home situated on 2.5 acres, 2500 sq. ft. Include; living room with vaulted ceiling, family room with fireplace, dining room, kitchen with cherry cabinets and granite counters, 4 bedrooms 2.5 updated baths, first floor laundry, great three season porch overlooking fruit orchard and established plantings, oversized rear deck for outdoor dining, double lot, 3 garages. HWBB, central air
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$498,000 6.48 acres 3 Beds | 2 Baths | 1296 sqft
5 Lucky Ln, Great Barrington, MA 01230 - Berkshire County

6.48 acres Great Barrington, MA

SUNNY OPEN RANCH with mountain views and beautifully landscaped grounds.Open plan kitchen/living and dining, a master bed and bath plus two additional BR and bath. Fully finished lower level has den, office and laundry room. An expansive deck wraps around, overlooking fruit and specimen trees and perennial gardens.Heated 2 car garage/workshop has 1/2 bath. TOTAL PRIVACY, YET MINUTES TO TOWN.
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$479,900 3.5 acres 3 Beds | 2 Baths | 2227 sqft
8 Crimson Ln, Great Barrington, MA 01230 - Berkshire County

3.5 acres Great Barrington, MA

LOCATION, LOCATION, LOCATION. 247 ft. of frontage on beautiful, bucolic Williams River. This contemporary style Berkshire home is situated in park like setting. Located at the end of cul de sac, this home yields plenty of privacy, and yet, is not isolated. Charming gazebo for those summer evenings. Large deck in the rear of the house. Large Master Bedroom with walk-in closet. Min. from downtown GB
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$460,000 3.5 acres 3 Beds | 2 Baths | 3016 sqft
234 LONG POND Rd, Great Barrington, MA 01230 - Berkshire County

3.5 acres Great Barrington, MA

GRACIOUSLY LANDSCAPED LOFT-LIKE COMTEMPORARY This loft-like contemporary set on a historic rural road offers privacy and convenience close to the center of Great Barrington. The open plan living, dining, kitchen and screen porch were designed to enjoy the pastoral and woodland views from the second floor.