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Explore Similar Homes Within 10 Miles of Windsor, MA

  • /7

    $850 Per Month

    • 0.5 Baths
    • 1,215 Sq Ft
    • Property for Rent

    86 N Summer St, Adams, MA 01220

    Inexpensive retail/ office opportunity in the business district of the town of Adams. This space is just over 1,200 SQFT with street level access. Offering a gross lease with minimal responsibilities and minimal annual increases. With it's ease of entry, this could be a great place to start your new business endeavor or relocate from your current location to size up or down.

    Agent Photo

    Corey Bishop

    BISHOP WEST REAL ESTATE

    (413) 779-8544

    86 N Summer St, Adams, MA 01220
  • /17

    $1,750

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Condo for Rent

    18 Harris St Unit Central Pittsfield Apt., Pittsfield, MA 01201

    This property at 18 Harris St features 3 bedrooms and 1 bathroom, totaling 1,600 square feet of living space. The living room provides ample space for relaxation and entertainment, while the bedrooms are designed for comfort and privacy. The bathroom is equipped with essential fixtures and provides convenient access from the main living areas. Additional amenities include a smoke-free

    18 Harris St Unit Central Pittsfield Apt., Pittsfield, MA 01201
  • /6

    $950 Per Month

    • 0.5 Baths
    • 500 Sq Ft
    • Property for Rent

    644 North St, Pittsfield, MA 01201

    Welcome to your new business location at 644 North Street in the vibrant city of Pittsfield, Massachusetts! This prime first-floor retail/office space offers an exceptional opportunity to establish your presence in a bustling commercial district. This space is ideally suited for a boutique shop, professional office, or any other entrepreneurial venture you envision. Its location on a busy main

    Agent Photo

    Syrah Bradley

    BISHOP WEST REAL ESTATE

    (413) 553-1142

    644 North St, Pittsfield, MA 01201
  • /20

    Starting at $1,082 Plus Fees

    • Studio

    109 Housatonic St, Lenox, MA 01240

    **INCOME RESTRICTIONS: Studio, minimum income requirement $38,700. One-bedroom, minimum income requirement $51,600. Two-bedroom, minimum income requirement $58,980. Welcome to Lenox Schoolhouse Apartments — newly renovated apartment living in the heart of the Berkshires. Offering thoughtfully updated studio and one-bedroom apartment homes, this charming community combines historic

    Lenox Schoolhouse Apartments

    (413) 553-1971

    109 Housatonic St, Lenox, MA 01240
  • /2

    $800 Per Month

    • 700 Sq Ft
    • Property for Rent

    85 Main St, North Adams, MA 01247

    Office 208B is located on Main St which is consistent of much foot traffic and surrounded by popular local businesses. Mass Moca and the Massachusetts College of Liberal Arts is close by bringing a diverse group of people.

    Agent Photo

    Michael Hernandez

    360BERKSHIRE REALTY GROUP

    (413) 923-6308

    85 Main St, North Adams, MA 01247
  • /17

    Starting at $1,570 Plus Fees

    • 2 - 3 Beds

    66 Brushwood Way, Lenox, MA 01240

    Forge is a brand new mixed-income housing community in Lenox, MA. The development includes 65 apartments within 13 townhome-style buildings, and a community clubhouse. Each building at Forge contains 5-6 apartments, with a mix of one-, two-, and three-bedroom apartments available at various income tiers (30, 60, 120% AMI). Apartments have their own entrances at a new road loop, which is

    Forge

    (413) 728-1844

    66 Brushwood Way, Lenox, MA 01240
  • /14

    $1,956 Per Month

    • Studio
    • 2 Baths
    • 1,745 Sq Ft
    • Property for Rent

    195 South St, Pittsfield, MA 01201

    An exceptional opportunity to secure a highly visible, ground-floor commercial space in the heart of the city. Formerly occupied by a medical practice, this well-maintained suite offers layout suited to a broad spectrum of professional, wellness, and service-oriented uses. The space features a welcoming reception area, multiple private offices or treatment rooms, Tenants will benefit from an

    Agent Photo

    Peter West

    BISHOP WEST REAL ESTATE

    (413) 338-8133

    195 South St, Pittsfield, MA 01201
  • /13

    $1,900 Plus Fees

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    278 E Main St Unit 2, North Adams, MA 01247

    Property Id: 2503603Large apartment on upper two floors within charming Victorian House located within walking distance to library, downtown, MCLA and Mass MoCA. Two bedrooms, one office, fully furnished kitchen, two bathrooms, one storage room, dining area and living room with a view for watching sunsets. Water & Trash included. Credit Score of 670 or better, income 3 x rent,

    (781) 303-7318

    278 E Main St Unit 2, North Adams, MA 01247
  • /13

    $2,800 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,250 Sq Ft
    • Condo for Rent

    520 State Rd Unit 207, North Adams, MA 01247

    Set within the region's most celebrated mill conversion, Loft 207 at Greylock WORKS is a beautifully scaled 1BR | 1.5BA + Study Berkshires residence offering 1,250 SF of luminous, corner-exposure living. With 12.5-foot ceilings, expansive proportions, and oversized windows drawing natural light from two sides, this refined home blends industrial authenticity with contemporary design, creating a

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 307-3468

    520 State Rd Unit 207, North Adams, MA 01247
  • /4

    $18 Per Month

    • 4 Baths
    • 10,125 Sq Ft
    • Property for Rent

    10 Wendell Avenue Extension, Pittsfield, MA 01201

    Office suites available for lease in ideal downtown Pittsfield location! There currently two suites on the second level and two on the first floor available. Heat, Electric and AC included. Building is very well kept and features renovated bathrooms and key card access. High traffic area with on-street parking.

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    10 Wendell Avenue Extension, Pittsfield, MA 01201
  • /2

    $1,800

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Condo for Rent

    90 Lincoln St Unit 92 Lincoln St, Pittsfield, MA 01201

    Classic Duplex style Apartment Unit. This big apartment host 3-4 bedrooms, 2 bath, eat-in kitchens, large living rooms, and laundry hook-ups. Separated basements and utilities. Off-street parking. Nice large yard.

    90 Lincoln St Unit 92 Lincoln St, Pittsfield, MA 01201
  • /7

    $1,000 Per Month

    • 700 Sq Ft
    • Property for Rent

    19 Williamstown Rd, Lanesborough, MA 01237

    available soon. This new commercial property offers 4 available spaces for lease, 700 sq ft per space, easy access, visibility to road, radiant heat, security cameras, fiber optics, 3 phase power, custom buildout options like a mezzanine, bathroom or kitchen potential, lease 1 or all 4 spaces with unlimited potential. Need more space, an additional 9 units are planned for this facility.

    Matt Jarck WILLIAM PITT SOTHEBY'S - LENOX

    19 Williamstown Rd, Lanesborough, MA 01237
  • /10

    $2,000

    Total Monthly Price

    • 1 Bed
    • 1.5 Baths
    • 864 Sq Ft
    • House for Rent

    108 Lindsay Hill Rd, Worthington, MA 01098

    This is a NEW complete building renovation on 25 acres of forest in a beautiful and quiet hill town between Pittsfield and Northampton. This lovely property is on a gravel road with neighbors down the road, but not in sight. The whole second floor is a very large bedroom. Everything in the house is new: gas range, dishwasher, refrigerator, washer and dryer and mini splits. Farmhouse sink, heated

    108 Lindsay Hill Rd, Worthington, MA 01098
  • /33

    $3,200 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    181 Park Ave Unit A, Dalton, MA 01226

    Spacious and bright remodeled unit offering four bedrooms and 2.5 bathrooms. First floor features and expansive living room and and kitchen with new granite countertops. Along with a formal dining room, half bathroom, laundry room, and bedroom. Second floor included a primary bedroom with en-suite and two additional bedrooms and another full bathroom. All rooms have new flooring, fresh paint, and

    Cory Evangelisto NOCHER REALTY

    181 Park Ave Unit A, Dalton, MA 01226
  • /27

    $1,550

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Condo for Rent

    53 Orchard St Unit 53 Orchard St. #1, Pittsfield, MA 01201

    Charming, light-filled 2 bedroom 1 bath, first-floor apartment. Newly remodeled kitchen with newer appliances and newly remodeled bathroom. Wood floors throughout. Outdoor deck & fenced backyard. Includes your very own off-street reserved parking space in front of building. The property is well-maintained and includes snow removal, lawn care & trash service. Around the corner from BMC &

    53 Orchard St Unit 53 Orchard St. #1, Pittsfield, MA 01201
  • /15

    $1,800 Per Month

    • 2,346 Sq Ft
    • Property for Rent

    324 North St, Pittsfield, MA 01201

    Available for immediate occupancy, this freshly renovated, open-concept commercial space offers approximately 4,500 square feet in the heart of downtown Pittsfield. A blank slate, perfect for a wide range of uses like retail, office space, art gallery, wellness/fitness studio, boutique, or a creative space. Features include street-level storefront with large display windows, front & rear

    Patricia Molina CENTURY 21 NORTHEAST

    324 North St, Pittsfield, MA 01201
  • /2

    $1,600

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    44 Robbins Ave Unit 46-2, Pittsfield, MA 01201

    Outstanding 4-Apartments ! Unit 44-1 ( 2 bedrooms) 44-2 ( 3 bedrooms) 46-1 ( 2 bedrooms) and 46-2 (3 bedrooms)This well-maintained multifamily property features four spacious units, each renovated, offering strong rental appeal.

    44 Robbins Ave Unit 46-2, Pittsfield, MA 01201
  • /23

    $3,500 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,867 Sq Ft
    • House for Rent

    34 Galway Ct, Lenox, MA 01240

    AVAILABLE TO RENT FROM 10/1/2026 TO MAY 30, 2027. 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

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    34 Galway Ct, Lenox, MA 01240
  • /21

    $1,999

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    195 Francis Ave Unit 3 and 4, Pittsfield, MA 01201

    -Fresh Paint and hardwood floors -Basement for storage -free laundry hook it in basement

    195 Francis Ave Unit 3 and 4, Pittsfield, MA 01201
  • /17

    $1,000 Per Month

    • 2 Baths
    • 1,250 Sq Ft
    • Property for Rent

    34 Depot (Ste L1) St, Pittsfield, MA 01201

    Positioned in a convenient and accessible location, this ground level office space offers a practical and professional setting for a variety of business uses. The space features a large entry room and depending on your use, could have 2/3 offices and a conference room. This unit includes interior and exterior access, two private half bathrooms, and off-street parking adds to the overall

    Cory Evangelisto NOCHER REALTY

    34 Depot (Ste L1) St, Pittsfield, MA 01201
  • /6

    $1,200

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    43 John St Unit 2, Pittsfield, MA 01201

    This is a 1-bedroom unit. It is a second-floor apartment located in quiet neighborhood and includes stove, refrigerator. Tenant pays own utilities and it heats by electric. No pets of any kind allowed. No smoking. Ten minutes to downtown, banking, groceries, pharmacy, shopping and entertainment. On bus line. Shown by appointment. Must complete online application.

    43 John St Unit 2, Pittsfield, MA 01201
  • /2

    $1,500 Per Month

    • Studio
    • 0.5 Baths
    • 3,500 Sq Ft
    • Property for Rent

    106 Church St, Cheshire, MA 01225

    Large commercial space for lease. Versatile layout, suitable for retail, restaurant, office/meeting space. Endless possibilities to customize for your business needs.3 phase electric in place.Bring your business to Cheshire or start your dream business!

    Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

    106 Church St, Cheshire, MA 01225
  • /27

    $1,345

    Total Monthly Price

    • Studio
    • 1 Bath
    • 350 Sq Ft
    • Condo for Rent

    3401 Hancock Rd Unit 3W, Williamstown, MA 01267

    This property located at 3401 Hancock Rd features a studio layout with 0 bedrooms and 1 bathroom, encompassing a total of 350 square feet. The living space is efficiently designed, offering essential amenities such as air conditioning, a dishwasher, and in-unit washer/dryer for convenience. The bathroom is equipped with standard fixtures and provides necessary privacy. The unit comes furnished,

    3401 Hancock Rd Unit 3W, Williamstown, MA 01267
  • /15

    $3,449 Per Month

    • Property for Rent

    9 Brushwood Way Unit 9, Lenox, MA 01240

    Discover elevated living in this brand new 3 bedroom apartment at Lenox's newest community. Designed with modern finishes and bright, open layouts, this home offers comfort, style, and space to truly settle in. Step outside your door and enjoy resort style amenities, including a clubhouse with a welcoming community room, fitness center, and expansive outdoor deck. Wander scenic walking trails,

    Keyla Girard LAMACCHIA REALTY, INC

    9 Brushwood Way Unit 9, Lenox, MA 01240
  • /11

    $1,450

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • 2 Bedroom Apartment for Rent – Pittsfield, MA – $1,450/month

    456 Fenn St Unit 4, Pittsfield, MA 01201

    Freshly updated first-floor 2-bedroom apartment available now in Pittsfield! This move-in ready unit features fresh paint throughout and brand-new flooring, giving it a clean and modern feel.Conveniently located near downtown, you'll have easy access to shops, restaurants, and local amenities.Rent is $1,450 per month for a 2 bedroom, 1 bathroom unit. The apartment has fresh paint

    456 Fenn St Unit 4, Pittsfield, MA 01201
  • /37

    $2,500 Per Month

    • 2 Baths
    • 6,680 Sq Ft
    • Property for Rent

    1745 Massachusetts 2, Charlemont, MA 01370

    3 Months Free! Location, Location!! Capture the energy of the iconic Mohawk Trail with this rare restaurant space located directly on Route 2. Boasting breathtaking river views & endless potential, this expansive space with a fully equipped commercial kitchen is ready for your culinary vision. The full bar, live-music stage, dance floor, & ample seating make it ideal for everything from nightly

    Nicole Vadnais KELLER WILLIAMS REALTY

    1745 Massachusetts 2, Charlemont, MA 01370
  • /15

    $1,450

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    132 E Quincy St Unit 3, North Adams, MA 01247

    132 E Quincy St Unit 3, North Adams, MA 01247
  • /6

    $14 Per Month

    • 1.5 Baths
    • 1,274 Sq Ft
    • Property for Rent

    99 Hawthorne Ave, Pittsfield, MA 01201

    The industrial aesthetic of this classic New England mill offers a unique space for your organization or business to call home. The office space has terrific light and height, new windows, exposed brick, hardwood floors and updated systems including smart LED lighting. This suite is one of three tenant spaces in the building, all of which share a common area with a kitchen and two bathrooms.

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    99 Hawthorne Ave, Pittsfield, MA 01201
  • /7

    $1,200

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Spacious 1–2 Bedroom Apartment for Rent – Adams, MA

    12-14 E Hoosac St Unit 5, Adams, MA 01220

    Now available – a clean and well-maintained 1–2 bedroom apartment in Adams, MA. This third-floor unit is suitable for individuals, couples, or roommates, with space that can easily accommodate a second bedroom or home office.The apartment features gas heat and a gas stove for efficient heating and cooking, along with a brand-new refrigerator. A laundry center is located in the building,

    12-14 E Hoosac St Unit 5, Adams, MA 01220
  • /17

    $2,300 Per Month

    • 4 Beds
    • 1.5 Baths
    • 1,292 Sq Ft
    • House for Rent

    88 Wahconah St, Pittsfield, MA 01201

    Fully furnished 3-bedroom home with an additional room set up as a dedicated office—perfect for remote work or extended stays. This property includes all utilities, cable, and high-speed internet for a seamless, move-in-ready experience. Two off-street parking spaces are available. Conveniently located just minutes from Berkshire Medical Center and close to downtown Pittsfield, with easy access

    Patricia Molina Century 21 North East

    88 Wahconah St, Pittsfield, MA 01201
  • /21

    $2,000

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • 117-119 Lincoln St

    117-119 Lincoln St Unit 117, Pittsfield, MA 01201

    117-119 Lincoln St Unit 117, Pittsfield, MA 01201
  • /3

    $1,690 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    14,16,20 W Shore Dr Unit 1,2,4, Goshen, MA 01032

    This rate is by the WEEK not the month. The cottages are on the premier summer vacation lake in the valley. Swim, kayak(5), paddle board(1), trampoline raft, canoe(1), or sail on this this beautiful 100 acre private lake(no motor boats allowed) that is adjacent to the 1500 acre DAR with it's wonderful hiking and biking trails! Great fishing as well! All three cottages have their unique features

    Robert Raymond Hampshire Realty Company

    14,16,20 W Shore Dr Unit 1,2,4, Goshen, MA 01032
  • /2

    $1,500

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 2/4 Franco Terrace

    2-4 Franco Terrace Unit 4 Franco Terrace, Pittsfield, MA 01201

    2-4 Franco Terrace Unit 4 Franco Terrace, Pittsfield, MA 01201
  • /13

    $1,250 Per Month

    • Condo for Rent

    7 Albert St Unit 1, Adams, MA 01220

    Recently renovated first floor apartment with a widened bathroom. Features an open-concept kitchen with stove and refrigerator included. One bedroom has been updated with brand new carpeting.Convienient 2 Bedroom - 1 Bath First floor apartment. Close to downtown Adams, MA

    Christian Garner NOCHER REALTY

    7 Albert St Unit 1, Adams, MA 01220
  • /2

    $2,895

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,906 Sq Ft
    • COMING SOON - Lovely Single Family Home

    25 Yarmouth St, Pittsfield, MA 01201

    Charming three-bedroom, two-bath home in Pittsfield offering lake views and a private back yard. The spacious kitchen features stainless steel appliances and is complemented by a separate dining room—ideal for everyday meals and entertaining. Step outside to an entertainment deck overlooking the yard space, with convenient off-street parking included. Located in a neighborhood setting, this home

    25 Yarmouth St, Pittsfield, MA 01201
  • /13

    $2,250 Per Month

    • 1 Bath
    • 750 Sq Ft
    • Property for Rent

    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

    27 Housatonic St, Lenox, MA 01240
  • /13

    $1,550

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • Beautifully Updated 3-Bedroom First Floor Apartment – North Adams, MA – $1,600/month

    55-57-57 South St Unit 55, North Adams, MA 01247

    Welcome home to this freshly updated 3-bedroom, first-floor apartment in North Adams. Thoughtfully refreshed and move-in ready, this space offers a bright, modern feel with freshly painted hardwood flooring, updated lighting, fresh, neutral paint throughout, and a brand-new gas boiler just installed—providing efficient and reliable heating.The layout is both practical and comfortable,

    55-57-57 South St Unit 55, North Adams, MA 01247
  • /10

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    4 Pleasant St, Adams, MA 01220

    Fully furnished downtown house for rent. 2 bedrooms, 1 full bath, kitchen, living, dining.Each room has it's own heating/cooling unit.Centrally located, on the Ashwillticook Bike Trail.

    Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

    4 Pleasant St, Adams, MA 01220
  • /5

    $1,700

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • Charming 3-Bedroom Apartment in a Prime Location

    28 Merriam St, Pittsfield, MA 01201

    This spacious and character filled 3 bedrooms; 1 bath duplex is located in a highly desirable area. This home blends classic charm with functional living space, featuring beautiful hardwood floors, original woodwork, and abundant natural light throughout. The large living and dining areas offer a warm, inviting atmosphere, complete with oversized windows and timeless architectural details. The

    28 Merriam St, Pittsfield, MA 01201
  • /4

    $21 Per Month

    • 2 Baths
    • 18,986 Sq Ft
    • Property for Rent

    1450 East St, Pittsfield, MA 01201

    Position your business for success in this well-maintained commercial building at 1450 East St. Now available: Suite 6J-L (618 sf) with two existing plumbing fixtures, as well as 6G (356 sf) 6C (302sf). in a high-traffic location, perfect for attracting clients and boosting brand exposure. The freshly paved parking lot offers ample parking in both the front and rear of the building, making it

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    1450 East St, Pittsfield, MA 01201

Why Live in Windsor

Windsor, Massachusetts, nestled in the tranquil Berkshires, offers residents a rural lifestyle surrounded by trees and natural beauty. Located 20 miles south of the Vermont border, Windsor is characterized by its quiet, slow-paced environment, ideal for those seeking a peaceful retreat. Home styles in Windsor range from off-grid cottages to expansive hillside retreats, with ranch-style homes, saltboxes, and farmhouses dotting the landscape. Outdoor recreation is abundant, with the Hoosac Range providing opportunities for hiking, snowshoeing, and snowmobiling. Tamarack Hollow Nature & Cultural Center offers guided hikes, while Wahconah Falls State Park features a dog-friendly trail leading to a stunning 40-foot waterfall. Windsor State Forest spans 1,800 acres, offering year-round activities such as hunting and hiking. Notchview, a Trustees of Reservations property, is popular for cross-country skiing and biking.

Residents are zoned for Central Berkshire Public Schools, which have high ratings and graduation rates between 94% and 97%. Windsor is a car-dependent area, with Berkshire Trail connecting it to other communities. Emergency care is available 30 minutes away at North Adams Regional Hospital, and Bradley International Airport is about an hour and 20 minutes south. Shopping and dining options are at least 20 minutes away, with local favorites like homemade samosas at Sanger General Store and groceries at Old Creamery Co-Op in Cummington. Dining in Dalton includes Shire Tavern, known for its farmhouse-style ambiance. Nearby Cummington hosts agricultural events and fairs, including the Hampshire County 4-H Fair and the Massachusetts Sheep and Woolcraft Fair, providing family-friendly entertainment.

Frequently Asked Questions

What are the most popular zip codes in Windsor, MA for renters?
The most popular zip codes in Windsor, MA for renters include 01220, 01201, 01247, 01240 and 01267.
How to Rent a Home