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Apartment for Rent
1 Bed
207 Pleasant St, Great Barrington, MA 01230
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Apartment for Rent
1 Bed
207 Pleasant St, Great Barrington, MA 01230
$3,000 total monthly price
123 Main St, Great Barrington, MA 01230
High Visibility - High Traffic former Gas Station Building on Route 7 in the heart of the Berkshires. Ready for a creative new use. Pop-up shop? Antique Store? Art Gallery? Cafe? Bar? Ideal for Brand advertisement (Great signage on Rt 7 !) Funky and fabulous with 2 large spaces for your vision. Tanks are gone, property cleaned, on site Parking, and views of the Housatonic. Act fast!*Property also
Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON
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Lenox Schoolhouse Apartments
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$2,300 total monthly price
18 Morgan St Unit 1, Lenox, MA 01240
Fully renovated, fully furnished, like new Studio Apartment with 1 full bath. Must be seen to be appreciated. Location, location, location. It does not get any better than this. Just minutes from the heart of downtown Lenox and the world class music at Tanglewood. Features include modern finishes and a rare private garage stall.
Jim Moir WILLIAM PITT SOTHEBY'S - GT BARRINGTON
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LUXURY 2BR Lenox, ALL Utilities included!
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68 Kemble St, Lenox, MA 01240
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27 Housatonic St, Lenox, MA 01240
Make your dreams come true! Perhaps one of the best retail locations in Historic downtown Lenox. This highly sought after space is centrally located with high foot traffic count and is located on the corner of Church St. and Housatonic. The 750 sq.ft. has two great large window wells along the sidewalk entrance and includes your own bathroom and kitchenette. Nestled amongst dozens of small shops,
Tim Gallagher STONE HOUSE PROPERTIES, LLC
$2,100 per month plus fees
Mahaiwe Building
1 Bed
4 Castle St, Great Barrington, MA 01230
$2,250 total monthly price
44 Main St Unit 3, Stockbridge, MA 01262
Totally Renovated, Newly Furnished, Stockbridge In-Town Location. Truly a ''renter's dream come true.''Must be seen!Rent is $2,250/Month September to June and $4500/month for July and August.No pets.
George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON
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The Garage
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343 Main St, Great Barrington, MA 01230
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33 S Main Rd, Otis, MA 01253
Nicely renovated and beautifully furnished Colonial rental located in the heart of Otis. The updated eat-in kitchen is enhanced by attractive wood floors that exist throughout the home. The bathrooms, the propane furnace, and the windows have also been updated. The town has provided high speed broadband service throughout the community so if you need to work from home, the required technology is
George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,305 - $3,447 per month plus fees
Forge
1 - 3 Beds
66 Brushwood Way, Lenox, MA 01240
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44 Main St Unit 1, Stockbridge, MA 01262
STOCKBRIDGE IN-TOWN LOCATION. Fully Renovated as of April 1, 2025, Fully Furnished, Like New. 3 Bedroom Apartment. Must be seen to be appreciated. Location, Location, Location. It doesn't get any better than this. JULY AND AUGUST RENTS ARE $8000 per Month. Monthly rents outside of July and August will be $4,250 per month.
George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$3,500 total monthly price
165 Stockbridge Rd, Lee, MA 01238
Modern 2bdrm guesthouse w/ private porch with sweeping views on historic property. Price does not include utilities, but we can offer an all-inclusive monthly rate. Primary bedroom and the living room have skylights (sun-filled daytime). Primary bdrm has door to porch. Bathroom has Rain-shower and tub. Top of line W/D. Kitchen used and loved by chefs. Farmhouse dining table + kitchen
$1,900 total monthly price
402 Park St, Great Barrington, MA 01230
Looking for the perfect space to grow your business? This exceptional first-floor commercial property in the charming village of Housatonic checks all the boxes. Step into a spacious, open-concept layout, ideal for retail, office, or creative ventures. With both heating and air conditioning, you'll have year-round comfort to keep your team and customers happy. Need a little extra privacy? The
Suzann Ward HOUSATONIC REAL ESTATE
$2,500 - $9,000 total monthly price
1579 Pleasant St, South Lee, MA 01260
Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.
$1,900 total monthly price
402 Park St Unit 1St Floor, Great Barrington, MA 01230
Looking for the perfect space to grow your business? This exceptional first-floor commercial property in the charming village of Housatonic checks all the boxes. Step into a spacious, open-concept layout, ideal for retail, office, or creative ventures. With both heating and air conditioning, you'll have year-round comfort to keep your team and customers happy. Need a little extra privacy? The
Suzann Ward HOUSATONIC REAL ESTATE
$2,500 - $3,600 total monthly price
1579 Pleasant St, South Lee, MA 01260
Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.
$41,500 total monthly price
310 Twin Lakes Rd, Salisbury, CT 06068
This charming lake house on Twin Lakes delivers the quintessential year-round summer retreat experience in the picturesque Litchfield Hills of Connecticut. "The Lodge" combines 4 bedrooms, 2.5 baths, and an open floor plan perfect for family gatherings and friendly get-togethers, creating a nostalgic and inviting atmosphere full of character and charm. The spacious interior centers around
Tracy Macgowan Elyse Harney Real Estate
$2,500 - $3,600 total monthly price
1579 Pleasant St, South Lee, MA 01260
Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.
$30,000 total monthly price
261 Taconic Rd, Salisbury, CT 06068
***Available 5/23/26 through 9/8/26, summer full term*** Taconic Waterfront Carriage House. Step through the Living Room French doors to the terrace and gardens overlooking the Channel from Twin Lakes, or enjoy serene, landscaped rock vistas from any room in this turn-of-the-century Carriage House. Master Bedroom suite, plus two Bedrooms with Bath on the first floor; fourth Bedroom and Bath on
Colleen Vigeant Elyse Harney Real Estate
$2,750 total monthly price
3 Meadow St, Housatonic, MA 01236
This property at 3 Meadow St. features 1 bedroom and 1 full bathroom, with a downstairs den that can work as a second bedroom and office space. This old storefront offers an open floor plan with a chefs kitchen that provides ample room for relaxation and entertainment. The bathroom includes a deep soaking tub and waterfall shower as well as another fun loft space through a large walk in closet.
$2,000 per month
3191 New York 23 Unit 3, Hillsdale, NY 12529
Well-maintained 2-bedroom, 1-bath apartment offering comfortable living with a functional layout. The unit features a bright living area, an updated kitchen with ample cabinetry, and two well-sized bedrooms with good natural light. The bathroom is clean and modern, with a full tub/shower. Enjoy easy access and sliding glass doors that open to a covered outdoor space—perfect for fresh air and
Greg Berardi Berardi Realty
$3,500 per month
230 Middle Rd, Austerlitz, NY 12017
Tucked along a winding country road, this 3-4 bedroom Cape feels worlds away from everything—yet close to all that makes the Berkshires & Hudson Valley special. Set on two wooded acres where light filters through old maples and the seasons feel close at hand, it's a home that invites you to slow down and breathe. Step inside and you'll sense the calm immediately. The living room gathers around a
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3191 New York 23 Unit 1, Hillsdale, NY 12529
Well-maintained 2-bedroom, 1-bath ground-floor apartment (with limited steps) offering comfortable living with a functional layout. The unit features a bright living area, an updated kitchen with ample cabinetry, and two well-sized bedrooms with good natural light. The bathroom is clean and modern, with a full tub/shower. Enjoy easy access with ground-level entry and sliding glass doors that open
Greg Berardi Berardi Realty
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474 East St, Mount Washington, MA 01258
$4,200 total monthly price
266 Old Forge Rd, Riverton, CT 06065
Secluded Contemporary Retreat on 3+ Acres | 4 Bed / 4 Bath Rare rental opportunity in the Litchfield Hills! Escape to privacy in this stunning 3,229 sq. ft. Contemporary home set on 3.11 level, wooded acres. Light-filled open floor plan features soaring cathedral ceilings, skylights, and oversized windows framing serene forest views. The main level offers a spacious living area with a cozy wood
Valerie Nash KW Legacy Partners
$1,950 total monthly price
167 Norfolk Rd Unit Southfield Village #2, Southfield, MA 01259
Lovely 2 bedroom apt with lots of light and beautiful views. There is an additional loft space that is perfect for an office or yoga studio. Decks upstairs and downstairs with a large shared yard. Next door to cozy cafe in a quaint rural village surrounded by forests, farms, lakes & waterfalls. 20 Minutes to Great Barrington and15 minutes to ski area. Washer & Dryer provided in the unit. Rent
$2,700 per month
11449 New York 22, Austerlitz, NY 12017
Wonderful 2 bedroom 2 bath home in beautiful Austerlitz. Enjoy mountain views, a big back yard and privacy. 3000 per month plus utilities. No pets.
Andrea Gabel Gabel Real Estate
$7,500 total monthly price
320 Lakeshore Dr, Sandisfield, MA 01253
Wow! You must see to fully appreciate how special this home truly is. The construction quality is not only exceptional, but it is also new this year. The open floor plan log home features impactful vaulted ceilings, a spacious eat-in kitchen and pantry, a bright dining area, and an eye-catching Great Room with an effective wood burning stove. Four attractive bedrooms, 3 1/2 bathrooms, an office
George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$3,500 total monthly price
34 Galway Ct, Lenox, MA 01240
Perfectly located within 10 minutes to Tanglewood, this all one floor Ranch home is fully furnished and nicely appointed. The Galway Court neighborhood experiences limited traffic situations while making the trip to the center of Lenox and its shops and restaurants an easy bike ride for anyone so inclined. Like to golf? The Miraval Country Club is just five minutes away. The house features a very
George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$11,667 per month
Unlisted Address
EXCEPTIONAL WINTER RENTAL. Escape to this private 280-acre Berkshire estate just 10 min. from downtown Great Barrington. This 5,300 sq ft, 4BR/3BA historic home (c.1803) blends antique charm w/ modern luxury and features wide-plank floors, exposed beams, 4 fireplaces, radiant heat, skylights & vaulted ceilings. Wonderful chef's kitchen, formal dining room, sunroom, art studio, home office &
Claire Pollart LANCE VERMEULEN RE, INC
$32 total monthly price
73 W Center St, Lee, MA 01238
Be Part of the Vibrant Lee Community. Restored Historic Mill Machine Shop Building is a Commercial Condominium available for Lease, occupancy in 2027. Tenant responsible for cost of improvements which can be amortized over the life of the lease and built into monthly lease payment. Rentable space is 8,955 sf on two levels, 5,809 sf first floor, 3,146 sf second floor plus basement. Gallery,
Rich Aldrich WILLIAM PITT SOTHEBY'S - LENOX
$18,000 total monthly price
36 Millard Rd, Egremont, MA 01230
The perfect Berkshire country retreat for large gatherings awaits you. Bring your family andfriends to enjoy this stunning home and property on 18+ acres perched atop the Berkshire hillswith panoramic views. This generous and tasteful home offers endless spaces to relax andentertain. Lounge on the expansive deck with gorgeous views all around.Take a swim in yourown pond overlooking the
Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX
$4,500 total monthly price
261 Taconic Rd, Salisbury, CT 06068
Available 11/01/2025-4/08/2026 Taconic Waterfront Carriage House. Step through the Living Room French doors to the terrace and gardens overlooking the peaceful waterway that meanders by from Twin Lakes, or enjoy serene, landscaped rock vistas from any room in this magical turn-of-the-century Carriage House. A Primary Bedroom Suite, plus Two Bedrooms with shared Full Bath on the first floor;
Colleen Vigeant Elyse Harney Real Estate
$5,500 total monthly price
310 Twin Lakes Rd, Salisbury, CT 06068
This charming lake house on Twin Lakes delivers the quintessential year-round summer retreat experience in the picturesque Litchfield Hills of Connecticut. "The Lodge" combines 4 bedrooms, 2.5 baths, and an open floor plan perfect for family gatherings and friendly get-togethers, creating a nostalgic and inviting atmosphere full of character and charm. The spacious interior centers around
Tracy Macgowan Elyse Harney Real Estate
$5,500 total monthly price
308 Twin Lakes Rd Unit 312, Salisbury, CT 06068
Camp House Rental On Twin Lakes in Salisbury, Connecticut, is the quintessential summer getaway. This spacious 6 bedroom, 3 bathroom house offers a comfortable and inviting setting, perfect for a family vacation or gathering of friends. The main living area includes a kitchen, dining room, and living room with a cozy fireplace. The large screened porch provides ample outdoor seating and space for
Tracy Macgowan Elyse Harney Real Estate
$2,200 total monthly price
5 Glendale Rd, Stockbridge, MA 01262
Very sweet cottage on the grounds of a larger estate. graciously sized living / dining area with sliders to patio. Large bedroom with leafy views of flowering trees. Separate bath and dressing room. Excellent location in Stockbridge.
Martha Piper THE KINDERHOOK GROUP
$11,000 per month
Unlisted Address
Escape to this private 280-acre Berkshire estate just 10 min. from downtown Great Barrington. This 5,300 sq ft, 4BR/3BA historic home (c.1803) blends antique charm w/ modern luxury featuring wide-plank floors, exposed beams, 4 fireplaces, radiant heat, skylights, & vaulted ceilings. A chef's kitchen, formal dining room, sunroom, art studio, home office, & finished basement offer space for
Claire Pollart LANCE VERMEULEN RE, INC
$13,000 total monthly price
37 Kalliste Hill, Great Barrington, MA 01230
PRISTINE Rental with Wonderful Views! Seeing is believing. This picture perfect home has it all. First floor en suite primary bedroom, 2 en suite guest bedrooms, a fabulous family room, a living room with fireplace and mountain views, a country kitchen, a delightful screened porch and a deck that simply says ''Wow.'' This rental is available on a multi-month basis from March 2026. If you are
George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$9,500 total monthly price
44 Main St Unit 4, Stockbridge, MA 01262
Outstanding fully renovated 3 Bedroom, 2 bathroom apartment in the heart of Stockbridge. Walk to restaurants, shops, library, etc. The best apartment in the building even though it is on the third level. Fully furnished with all new quality appointments. Must be seen to be appreciated. Terrific Summer Rental! No pets. AVAILABLE JULY 1, 2026. Summer rent reduces to $4500 per month on September 1,
George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON
Monterey, MA, nestled in the southern Berkshires, is a mountain town known for its natural beauty and strong community ties. The area boasts numerous hiking trails and fishing lakes, including the popular Lake Garfield, which offers year-round activities such as swimming, kayaking, fishing, and ice skating. Beartown State Forest provides 12,000 acres for hiking, camping, mountain biking, and winter sports. Monterey's housing market features early 20th-century cottages and lakefront properties, with many being converted into larger year-round homes. The Southern Berkshire Regional School District, which includes Mount Everett Regional School, is noted for its smaller class sizes and individual attention. Residents often travel to nearby towns like Lee and Great Barrington for shopping and dining, with Great Barrington offering a variety of bakeries, cheese shops, and international cuisine. Cultural attractions are abundant, with the Boston Symphony Orchestra's summer home at Tanglewood in Lenox, just 15 miles north, and local art exhibitions at the Monterey Library. Despite its rural charm, Monterey is car-dependent, with main roads like Route 23 and Route 57 connecting to larger highways. The town is about 50 miles west of Springfield and 20 miles south of Pittsfield.