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50 Photos
LAMACCHIA REALTY, INC
$599,000
3 BD | 3 BA
Residential - Single Family

Welcome to this spacious and light-filled home just moments from scenic Pontoosuc Lake! Enjoy breathtaking sunrises and sunsets from your open-concept upper level, featuring soaring ceilings and expansive windows that fill the space with natural light. The beautifully updated kitchen offers ample room for dining and entertaining, complete with a breakfast bar and generous seating options--all perfectly positioned to enjoy the peaceful surroundings. The oversized primary bedroom boasts a flowing layout and a large walk-in closet, creating a serene retreat. Downstairs, the expansive lower level offers endless potential--ready to be finished to suit your style and needs.


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WILLIAM PITT SOTHEBY'S - LENOX
$600,000
3 BD | 4 BA
Residential - Single Family

Waterfront living at it's finest at desirable Long Lake. The main reason owners love Long Lake is because it is truly the only waterfront community in Columbia County which offers maintenance free living. The HOA takes care of all exterior maintenance such as snow plowing, landscaping, pool and amenities upkeep which leaves you with the job of enjoying your free time on the screen porch, kayaking, swimming, or enjoying the Hudson Valley and the Berkshires. This 3 bedroom 3 bath property is also quite special because it is an end unit and it is close to all of the amenities such as swimming, tennis, and the community beach. Beautifully designed by architect Steve Haas, this home features two levels of floor to ceiling windows, a sublime screened porch with cathedral ceiling, and large


32 Photos
LANCE VERMEULEN RE, INC
$630,000
4 BD | 3 BA
Residential - Single Family

Fantastic 4 BR Otis Wood Lands Contemporary situated at the end of a cul-de-sac close to all community amenities! This spacious home has great spaces for family and friends. Price includes furniture. Community amenities include pool, tennis/pickleball courts, fitness room, playground, lodge, lake and beach. New septic in 2023, new hot water heater 06/2025, new roof 2003. $4,000 reserve fund fee due from buyer at closing.


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PREFERRED COUNTRY PROPERTIES
$695,000
3 BD | 3 BA
Residential - Single Family

Modern Country FarmhouseBuilt to pamper its proud owner by offering a quiet, peaceful and very private get away w/ cathedral ceiling living room semi open to wonderfully equipped kitchen and breakfast area. Primary ensuite is spacious and bright -- offers all amenities you would ever wish for from a walk in closet, to bath with double vanity, Jacuzzi soaking tub, separate shower, separate toilet rm... a big plus is it's on the first floor, separate from guest areas. Second floor w/Loft library, two ample size guest rooms, bath and an extra spacious room for a studio/ creative room or spill over for overnight guests.. You will be amazed by the finished walk out space on the lower level.. it's use is yours to define. I envision a private work space or spacious game room which can fit a h


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WILLIAM PITT SOTHEBY'S - LENOX
$699,000
3 BD | 2 BA
Residential - Single Family

Discover your dream retreat in this stunning log home, nestled on 37 acres of breathtaking land that adjoins over 1,000 acres of serene state forest. This oasis offers an unmatched blend of tranquility and natural beauty, allowing you to escape from the hustle and bustle of everyday life. Imagine sipping your morning coffee on the wrap-around deck, soaking in the picturesque mountain views. Indulge in the ultimate relaxation experience with a soak in your wood-fired hot tub or a rejuvenating session in your outdoor sauna. Step inside and be captivated by the charming open floor plan. The chef's kitchen is a culinary enthusiast's dream, featuring a large island, elegant granite countertops, and a high-end Viking stove, perfect for entertaining guests or creating culinary masterpieces.


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WILLIAM RAVEIS REAL ESTATE
$719,000
3 BD | 4 BA
Residential - Single Family

Set along a historic road and just a stone's throw from Otis Reservoir, this stunning 3-bedroom, 3.5-bath home offers over 2,000 square feet of light-filled living space on more than 4 acres of natural beauty. Designed for both comfort and elegance, the home features three private ensuite bedrooms, including two conveniently located on the first floor, making it ideal for guests, family, or multigenerational living. The spacious primary suite offers a spa-inspired bath and peaceful views. The main living area is bathed in natural light, created by the walls of windows that frame the surrounding landscape and bring the outdoors in. Enjoy the warmth and comfort of the wood-burning fireplace that is the centerpiece of the main living area. Beautifully crafted with high-end finishes through


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STONE HOUSE PROPERTIES, LLC
$749,900
3 BD | 2 BA
Residential - Single Family

Classic lakefront cottage with frontage on quiet Benton Pond plus deeded rights to Big Pond. Four season contemporary Cape with an open plan featuring a window wall facing the lake and a brick fireplace. There are three bedrooms and two full baths plus a small loft. The screened porch is next to the kitchen, convenient for al fresco dining. Exterior access to the basement is perfect for storage of your canoes and kayaks. The home is located on over an acre and is the 2nd to the last on the road so very quiet. Less than 3 hours to NYC and 2 1/2 to Boston, near Tanglewood, Jacobs Pillow and most other Berkshire cultural attractions, as well as several state forests. If you have been looking for a reasonably priced lake home, this is your chance.


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THE KINDERHOOK GROUP - PITTSFIELD
$750,000
4 BD | 4 BA
Residential - Condo/Townhouse

Beautifully redone unit at desirable South Pond. Great views from all windows. Freshly remodeled kitchen and baths. Many association amenities like pool, Richmond Pond access and tennis.


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COHEN & WHITE ASSOCIATES
$759,000
3 BD | 3 BA
Residential - Condo/Townhouse

Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a gracious entry with custom flooring and cedar hall closet that flows beautifully into the great room with vaulted ceilings, gas fireplace and glass doors to the screened porch and deck with a scenic view of the woods. The lovely updated kitchen is open to the dining area and great room for comfortable open common spaces. The primary bedroom has wood flooring, walk-in fitted closet and tastefully renovated en-suite bath with custom finishes. Included on the main level is the charming half bath, garage with storage and laundry room. The second floor features a large loft flex space with oversized closet, two guest bedrooms and stunning full bath. The lower level walkout is


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MACCARO REAL ESTATE
$760,000
4 BD | 3 BA
Residential - Single Family

Renovated beautifully in 2023, this contemporary home is on 3.31 acres , includes a .22-acre parcel on Lake Garfield. Built in 1987 this four bedroom, 3 bath contemporary home is nestled in a wooded grove approximately 1/2 mile from the public beach at Lake Garfield. Enter the light filled living area with 1/2 cathedral ceiling and fireplace. There is an efficient kitchen layout with access to a charming, screened porch and an incredibly spacious deck. Two bedrooms and a full bath complete this main floor. The second floor consists of two spacious bedrooms each with its own bath. The primary bedroom has a large walk-in closet and a Juliet balcony overlooking the backyard. Please read the Supplemental Remarks to learn more about the house & lake lo


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LANCE VERMEULEN RE, INC
$775,000
3 BD | 2 BA
Residential - Single Family

Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful surroundings. Conveniently located just minutes from Sheffield village, Canaan (CT), and Great Barrington, this versatile property works beautifully as a full-time residence, vacation retreat, or investment opportunity in the heart of the Berkshires. This is a new build, and taxes have not yet been determined.


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COHEN & WHITE ASSOCIATES
$789,000
2 BD | 3 BA
Residential - Condo/Townhouse

This White Pines Garden Unit is a must see if you are considering condominium living in this sought after community. Open living Great Room/kitchen/dining with double volume glass to take in the view, fireplace & guest bath on main level. The lower level greets you with a tiled floor sunroom w/direct access to the spacious decking w/private courtyard outdoor space. The primary ensuite, guest bedroom w/full bath & laundry & office/flex space complete this level. This unit boasts a most convenient covered carport space. Assoc. amenities include a clubhouse w/exercise rm, indoor heated pool, 2 Har Tru tennis courts, hiking and walking trails, private beachfront on the Stockbridge Bowl with swimming and kayak & canoe storage or anchor your boat... ..all this and only minutes to Tanglewood


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$795,000
3 BD | 2 BA
Residential - Single Family

OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This Timber Fame (open floor plan) contemporary home features beautiful (wide-plank) pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the main level, and a wood stove on the lower level, add warmth and charm. Ready to move right in? With relatively low inventory level, particularly in Monterey, this listing is a lucky strike extra. Schedule your showing today.


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LANCE VERMEULEN RE, INC
$796,000
2 BD | 2 BA
Residential - Single Family

Architectural gem with lots of glass perched like a treehouse on the backside of Monument Mountain. The open, mid-century modern home was built in 2012 for maximum light, efficiency, and provides glittering views through the trees of the Housatonic River! 2 bedroom, 2 full baths-both ensuite + central AC, and a Scandinavian soapstone wood stove, permit included! Minutes from hiking trails, Taft Farm, Berkshire Mountain Bakery and downtown GB. Also close to town schools, Butternut, Tanglewood, and other Berkshire cultural centers. So quiet, yet close to everything. Design by AIA recognized architect Steve Dietemann.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$799,000
3 BD | 3 BA
Residential - Single Family

Stunning contemporary sanctuary in Ashley Falls offering perfect blend of modern design & natural surroundings. 3BR/2.5BA residence bathed in natural light. The first floor features a comfortable den, eat-in kitchen and gracious living room with marble wood burning fireplace. A thoughtfully designed floor plan flows seamlessly to outdoor spaces including large deck for al fresco dining & expansive screened room extending living into every season. Attached oversized 2-car garage and 2 finished rooms on the lower level. Meticulously maintained gardens, beautiful heated pool, multi-zone central A/C in an incredibly private setting. Perfect retreat minutes to Salisbury/Lakeville CT & Columbia County NY, close proximity to all Berkshire cultural & outdoor attractions.


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HARSCH ASSOCIATES
$842,500
3 BD | 3 BA
Residential - Single Family

MOTIVATED SELLER! MAJOR PRICE REDUCTION! This brand new contemporary in a quiet prime in-town location is now offered with a $50,000 buyer incentive towards closing costs and downpayment! Tucked away on a peaceful cul-de-sac just moments from the heart of town, this stunning new construction offers the rare combination of modern living within a well-established, highly desirable neighborhood. Originally a modest single-level home, this property has been thoughtfully reimagined and meticulously expanded over the past year. Now boasting over 1,700 square feet of stylish living space, it features three bedrooms, two and a half baths, and a spacious, insulated two-car garage. See More ..


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WILLIAM PITT SOTHEBY'S - LENOX
$875,000
3 BD | 2 BA
Residential - Single Family

Welcome to this exceptional 3-bedroom, 2-bathroom lakefront retreat w/an in-ground pool,located in the highly sought-after Otis Woodlands community. Perfectly situated on OWL Lake, this home offers a rare combination of natural beauty, modern upgrades, and an array of resort-style amenities, making it the ideal country escape or full-time residence.Step inside to an open-concept living area with soaring vaulted ceilings and abundant natural light streaming through large windows. The spacious kitchen boasts gleaming granite countertops, newer appliances, and custom cabinetry, creating the perfect space for entertaining or quiet meals. The living room, with its inviting warmth and charm, seamlessly flows into the dining area, making this home perfect for gatherings with family and friends.


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COHEN & WHITE ASSOCIATES
$875,000
3 BD | 3 BA
Residential - Single Family

Discover the perfect blend of comfort and charm with this stunning contemporary situated on two acres. There is a full-house Generac generator for comfort and peace of mind and central air. The great room is washed with natural light from the wall of windows and has a beautiful gas fireplace to provide additional warmth on cold Winter days. There is a circular flow into the spacious dining room and the updated kitchen making this home ideal for entertaining. A full bath and two charming guest bedrooms welcome visitors and offer opportunities for a home office. The oversized four-season sunroom offers magnificent light that takes in the picturesque landscaped surroundings and woodlands. It features an efficient gas stove for chillier days and screen inserts to help capture Summer breezes.


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COMPASS MASSACHUSETTS , LLC GB
$895,000
3 BD | 3 BA
Residential - Condo/Townhouse

Welcome to The Vanna Building at Winden Hill. An excuisite example of Period living, this sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.


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BISHOP WEST REAL ESTATE
$950,000
3 BD | 4 BA
Residential - Single Family

First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first level, is a charming screened porch for dining or just taking in the sounds of nature. An open deck on the backside of the main level awaits your enjoyment. The 2nd level contains two VERY large bedrooms Ensuite; both with walk-in closets along with more locations for maximizing the distant views. The finished lower/walkout level has a full bath for a possible 4th Ensuite and living space

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