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Explore Similar Homes Within 10 Miles of Windsor, MA

  • /7

    $850 total monthly price

    • 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) 216-3649

    86 N Summer St, Adams, MA 01220
  • /7

    $2,800 total monthly price

    • 0.5 Baths
    • 3,356 Sq Ft
    • Property for Rent

    101 Howland Ave, Adams, MA 01220

    High Visible Commercial Garage For Lease! Ideal for automotive, contractor, or mechanical use. Flexible layout with high ceilings. Featuring 3 working bays, two 10' x 10' garage doors and one oversized 13' x 12' door. Two additional bays are framed in and could be opened back up for additional garage doors totaling 5 bays. Large section of the building is heated with a waste oil burner. The

    Agent Photo

    Corey Bishop

    BISHOP WEST REAL ESTATE

    (413) 287-7789

    101 Howland Ave, Adams, MA 01220
  • /2

    $3,400 total monthly price

    • 2 Beds
    • 1.5 Baths
    • 850 Sq Ft
    • Condo for Rent

    34 Church St Unit 2B, Lenox, MA 01240

    Downtown Lenox!!Located in the heart of downtown Lenox, Unit 2B is a newly renovated condo nestled within shops, boutiques and numerous restaurants that are a staple to the Berkshires. This condo features 2 bedrooms, 1 full bathroom and an additional half bathroom. The spacious and open kitchen, living and dining area allows for plenty of gathering space. Living area has a beautiful working

    34 Church St Unit 2B, Lenox, MA 01240
  • /20

    $3,000 total monthly price

    • 2 Baths
    • 4,500 Sq Ft
    • Property for Rent

    17 Taconic Park Dr, Pittsfield, MA 01201

    4,500 sf FOR LEASE. Available for 1/1/2026 occupancy. With 2 ground level drive-in access doors, 2 offices and 2 bathrooms. Ample power. In addition to base rent of $3,000/mo tenant pays for heat, electricity, security, trash removal, telecommunications and renter's liability insurance. Landlord pays for taxes, insurance, water & sewer, snow removal and landscaping. Minimum 5-year lease.

    Rich Aldrich WILLIAM PITT SOTHEBY'S - LENOX

    17 Taconic Park Dr, Pittsfield, MA 01201
  • /18

    $1,595 total monthly price

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

    105 Parker St Unit 3, Pittsfield, MA 01201

    FREE!!!!! HEAT, HOT WATER, AND WIFI Spacious (800 sq. ft.) one bedroom apartment in a quiet Pittsfield neighborhood. In addition, to the indoor living space, it has an enclosed 4 season front porch and basement area for laundry. There is a patio in the backyard which is equip with a gas grill for private entertaining or family gatherings. A Washer and Dryer are available and located in

    105 Parker St Unit 3, Pittsfield, MA 01201
  • /12

    $1,800 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,425 Sq Ft
    • Property for Rent

    241 Second St, Pittsfield, MA 01201

    Available immediately: newly painted and renovated spacious ground floor three bedroom with tons of character conveniently located to shops, restaurants and hospitals in Pittsfield. Washer and dryer hook ups are in basement. The apartment has lots of light and parking, huge kitchen with lots of storage and a large, dry basement for additional storage. There is a front porch and back porch, and

    Heather Kelley GILCREST PROPERTIES

    241 Second St, Pittsfield, MA 01201
  • /4

    $1,305 - $3,447 per month plus fees

    Forge

    1 - 3 Beds

    66 Brushwood Way, Lenox, MA 01240

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

    66 Brushwood Way, Lenox, MA 01240
  • /6

    $1,500 total monthly price

    • 700 Sq Ft
    • Property for Rent

    19 Williamstown Rd, Lanesborough, MA 01237

    This new commercial property offers 2 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 both spaces unlimited potential. Need more space, an additional 11 units are planned for this facility.

    Matt Jarck WILLIAM PITT SOTHEBY'S - LENOX

    19 Williamstown Rd, Lanesborough, MA 01237
  • /25

    $1,082 per month plus fees

    Lenox Schoolhouse Apartments

    Studio

    109 Housatonic St, Lenox, MA 01240

    The Berkshires' newest community is NOW OPEN!!! Newly renovated studios and one bedrooms with ALL UTILITIES INCLUDED* - Spacious open layouts, brand new interiors, plush carpet, sunlit windows, abundant closet space. Lenox Schoolhouse Apartments is within walking distance to the center of town. Enjoy the local shops, art galleries, restaurants and entertainment. You'll be sure to experience

    109 Housatonic St, Lenox, MA 01240
  • /7

    $400 total monthly price

    • 2 Baths
    • 320 Sq Ft
    • Property for Rent

    80 Church St, Cheshire, MA 01225

    The town of Cheshire is offering this third floor double connecting room for rent. Offering approximately 320 square feet of space, making it suitable for a variety of office spaces or operations. The rental agreement is inclusive, covering the costs of heat, hot water, electricity, trash removal, and grounds maintenance. This simplifies budgeting and ensures predictable monthly expenses for

    Jason Nocher NOCHER REALTY

    80 Church St, Cheshire, MA 01225
  • /13

    $3,300 per month plus fees

    • 4 Beds
    • 2.5 Baths
    • House for Rent

    59 Longview Terrace, Williamstown, MA 01267

    Property Id: 2153399Furnished 4-bedroom house (2,650 square feet) plus office available for rent available starting October 15, 2025. Located on a quiet residential street in one of Williamstown's prettiest neighborhoods 2 miles from the Williams campus, offering spacious front and back yards as well as a stunning view of Mt. Prospect. Details: - 4 sizable bedrooms (1 queen bed, 2 full

    59 Longview Terrace, Williamstown, MA 01267
  • /30

    $500 total monthly price

    • Studio
    • 2 Baths
    • 1,857 Sq Ft
    • Property for Rent

    20 Bank Row, Pittsfield, MA 01201

    MULTIPLE PROFESSIONAL OFFICE SPACES READY FOR IMMEDIATE TENANCY. Located in the historic Bank Row Building above Patrick's Pub, mere steps from the Berkshire District Courthouse. Perfect for Attorneys! Conference room, private restrooms, hardwood floors, exposed brick walls. Central A/C in the front of the building and electric baseboard heat in the back. Electric cost will be figured into the

    John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    20 Bank Row, Pittsfield, MA 01201
  • /8

    $1,100 per month plus fees

    • 1 Bed
    • 1 Bath
    • House for Rent

    5 Dewey Ave, Pittsfield, MA 01201

    Property Id: 1335178Recently renovated.Looking for First and Last Month's Rent.Prospect tenants must pass background check:No evictions No criminal recordIncome must be three times monthly rent.Preferably no pets but exceptions can be made.Please call

    5 Dewey Ave, Pittsfield, MA 01201
  • /10

    $3,000 total monthly price

    • 1 Bed
    • 0.5 Baths
    • 2,700 Sq Ft
    • Property for Rent

    110 Union St, North Adams, MA 01247

    Prime Commercial Lease Opportunity in North Adams! This 3,000 sq ft metal garage offers four spacious bays, an office area, and a bathroom--perfect for your business headquarters. Features include concrete floors, forced hot air heat, two 14' garage doors and two 10' doors for easy access. Ideal for auto repair, equipment storage, furniture restoration, or tree service base. Clean, functional,

    Christine Girard STEEPLEVIEW REALTY - N. ADAMS

    110 Union St, North Adams, MA 01247
  • /11

    $1,300 per month plus fees

    • 1 Bed
    • 1 Bath
    • 1,647 Sq Ft
    • House for Rent

    284 Dalton Division Rd, Pittsfield, MA 01201

    Welcome to your new home in Pittsfield, MA! This inviting property offers a comfortable living space with the convenience of being just a short 10-minute drive from Berkshire Medical Center.Key property features include central heating and cooling, ensuring year-round comfort. Additionally, the home is equipped with air conditioning and ceiling fans, providing a refreshing atmosphere

    284 Dalton Division Rd, Pittsfield, MA 01201
  • /15

    $2,500 total monthly price

    • 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
  • /30

    $1,900 total monthly price

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

    20 Allessio St Unit 20, Pittsfield, MA 01201

    Enjoy this beautifully renovated 2-bed, 1-bath apt in the quiet and safe Lakewood neighborhood of Pittsfield! This bright and modern space features:Brand-new kitchen with all new appliances and a sleek marble countertop fully equipped with everything you need.In-unit laundryCozy living room with a 65-in TV + full-size pull-out couchEnclosed sunroom porchGreat water

    20 Allessio St Unit 20, Pittsfield, MA 01201
  • /34

    $5,500 total monthly price

    • 2 Baths
    • 6,370 Sq Ft
    • Property for Rent

    41 North St, Pittsfield, MA 01201

    Rare opportunity to become part of the vibrant downtown corridor with prominent location on the south end of North Street. Close to hotels, banking, retail and professional offices. In addition to many potential uses, it is currently set up as a restaurant and bar. Plenty of seating in the main dining room with an adjacent space to expand seating, game room, lounge or pool tables. Additional

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    41 North St, Pittsfield, MA 01201
  • /12

    $2,250 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    12 Applewood Ln Unit 12, Pittsfield, MA 01201

    Very quiet end unit in cul de sac. Only 12 units in development. Fully furnished renovated two bedroom two bath condo. Hardwood floors, carpets, freshly painted. One car garage with additional parking available on street. Convenient to shopping and cultural events in Berkshire County. Minutes from Pittsfield State Forest and downtown Pittsfield. Applicants are required to complete

    12 Applewood Ln Unit 12, Pittsfield, MA 01201
  • /4

    $1,000 total monthly price

    • Studio
    • 0.5 Baths
    • 1,100 Sq Ft
    • Property for Rent

    152 American Dr, North Adams, MA 01247

    1100 sq/ft retail, office, creative workspace located in the downtown business district.

    Michael Hernandez 360BERKSHIRE REALTY GROUP

    152 American Dr, North Adams, MA 01247
  • /6

    $1,800 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Condo for Rent

    100 Church St Unit Cheshire, Cheshire, MA 01225

    Easy access in desirable Cheshire, this 2nd floor remodeled unit features 3 bedrooms, brand new kitchen, full bath, living room and offers off street parking. No laundry.

    100 Church St Unit Cheshire, Cheshire, MA 01225
  • /5

    $700 total monthly price

    • 2 Baths
    • 600 Sq Ft
    • Property for Rent

    85 Main Suite 202 St, North Adams, MA 01247

    Unit #202 is centrally located on the second floor of 85 Main St. Benefit from the bustling foot traffic from the wide variety of professional offices that occupy this cornerstone of Main St. North Adams

    Michael Hernandez 360BERKSHIRE REALTY GROUP

    85 Main Suite 202 St, North Adams, MA 01247
  • /20

    $2,300 total monthly price

    • 3 Beds
    • 1.5 Baths
    • 1,122 Sq Ft
    • Condo for Rent

    83 Sadler Ave Unit 83 sadler, Pittsfield, MA 01201

    Property DescriptionWelcome to 83 Sadler Avenue in Pittsfield, MA — a spacious unfurnished three-bedroom, 1.5-bathroom apartment perfect for families or professionals. Priced at $2,300/month, this home includes heat and hot water, offering both comfort and value.All three bedrooms and the full bathroom are located upstairs, creating a private retreat, while the main floor features a

    83 Sadler Ave Unit 83 sadler, Pittsfield, MA 01201
  • /5

    $18 total monthly price

    • 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
  • /24

    $3,000 total monthly price

    • 2 Beds
    • 2.5 Baths
    • 1,650 Sq Ft
    • Condo for Rent

    1-6 Meadow Ln Unit 7-4, Lenox, MA 01240

    Recently renovated condo with hardwood floors, wonderful, spacious living/dining rooms, 2 bedrooms, each with its own bathroom. Newly renovated kitchen with quartz countertops. The living room has a sliding door opening to a balcony with steps that will take you to a 50 acre woodland interspersed by hiking trails and a brook. The lower level of the condo has a large room which can make a great

    1-6 Meadow Ln Unit 7-4, Lenox, MA 01240
  • /36

    $11 total monthly price

    • 2 Baths
    • 142,518 Sq Ft
    • Property for Rent

    703 W Housatonic St, Pittsfield, MA 01201

    703 West Housatonic Street is one of Pittsfield's most unique, multi-use buildings, perfect for a wide variety of businesses and organizations. Located on Route 20, it's ideally situated for easy access to Berkshires and nearby New York state. The property has been upgraded in every department. It's powered by its own solar field, has large parking lots, a tenant garden, fresh landscaping, and an

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    703 W Housatonic St, Pittsfield, MA 01201
  • /6

    $1,700 total monthly price

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

    18 Bay State Rd, Pittsfield, MA 01201

    This property located at 18 Bay State Rd features 3 bedrooms and 1 bathroom within a total of 1,600 square feet. The living room offers ample space for relaxation and entertaining. The bathroom is equipped with standard fixtures and provides essential amenities. Each bedroom is designed to accommodate various furniture arrangements, suitable for both individuals and families. The property is

    18 Bay State Rd, Pittsfield, MA 01201
  • /4

    $14 total monthly price

    • 1.5 Baths
    • 1,597 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
  • /13

    $1,435 - $1,685 total monthly price

    • 1 - 2 Beds
    • 1 Bath
    • 648 Sq Ft
    • Condo for Rent

    5 Highview Dr, Pittsfield, MA 01201

    Colonial Gardens is a lovely apartment complex currently offering 1 and 2-bedroom apartments. Rent includes the cost of heat, hot water and electricity, making this apartment an unbeatable deal! We require first and last month's rent prior to move in, and all applicants must pass credit, criminal and reference screening checks. Apartments are shown by appointment only. Rents subject

    5 Highview Dr, Pittsfield, MA 01201
  • /2

    $1,600 total monthly price

    • 2 Baths
    • Property for Rent

    21 Blackinton St, North Adams, MA 01247

    This 2-bedroom, 2-bath apartment offers comfort and convenience in the heart of North Adams. Features include new flooring, off-street parking, and medium to large windows for great natural light.Located within walking distance to Mass MoCA, MCLA, local schools, shops, restaurants, and gas stations. Ideal for students, professionals, or anyone looking to live close to downtown amenities.

    Michael Hernandez 360BERKSHIRE REALTY GROUP

    21 Blackinton St, North Adams, MA 01247
  • /13

    $1,435 - $1,685 total monthly price

    • 1 - 2 Beds
    • 1 Bath
    • 648 Sq Ft
    • Condo for Rent

    5 Highview Dr, Pittsfield, MA 01201

    Colonial Gardens is a lovely apartment complex currently offering 1 and 2-bedroom apartments. Rent includes the cost of heat, hot water and electricity, making this apartment an unbeatable deal! We require first and last month's rent prior to move in, and all applicants must pass credit, criminal and reference screening checks. Apartments are shown by appointment only. Rents subject

    5 Highview Dr, Pittsfield, MA 01201
  • /2

    $800 total monthly price

    • 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.

    Michael Hernandez 360BERKSHIRE REALTY GROUP

    85 Main St, North Adams, MA 01247
  • /13

    $1,435 - $1,685 total monthly price

    • 1 - 2 Beds
    • 1 Bath
    • 648 Sq Ft
    • Condo for Rent

    5 Highview Dr, Pittsfield, MA 01201

    Colonial Gardens is a lovely apartment complex currently offering 1 and 2-bedroom apartments. Rent includes the cost of heat, hot water and electricity, making this apartment an unbeatable deal! We require first and last month's rent prior to move in, and all applicants must pass credit, criminal and reference screening checks. Apartments are shown by appointment only. Rents subject

    5 Highview Dr, Pittsfield, MA 01201
  • /2

    $1,100 total monthly price

    • Studio
    • 1,400 Sq Ft
    • Property for Rent

    85 Main St, North Adams, MA 01247

    Unit #200C is centrally located on the second floor of 85 Main St. Benefit from the bustling foot traffic from the wide variety of professional offices that occupy this cornerstone of Main St. North Adams

    Michael Hernandez 360BERKSHIRE REALTY GROUP

    85 Main St, North Adams, MA 01247
  • /2

    $42,000 total monthly price

    • 6,000 Sq Ft
    • Property for Rent

    5 Whipple St, Pittsfield, MA 01201

    St Luke's Square. Entrance to lower level space from 1st level parking lot or rear, Whipple St.

    James McRory BERKSHIRE COUNTY REALTY

    5 Whipple St, Pittsfield, MA 01201
  • /2

    $60,000 total monthly price

    • Studio
    • 2 Baths
    • 3,060 Sq Ft
    • Property for Rent

    81 Linden St, Pittsfield, MA 01201

    Second floor of Sioga Club- Separate entrance + elevatorLandlord will break up 3500 sf into smaller spaces

    James McRory BERKSHIRE COUNTY REALTY

    81 Linden St, Pittsfield, MA 01201
  • /2

    $1 total monthly price

    • Property for Rent

    185 Columbia St, Adams, MA 01220

    Commercial Property for Lease. 8200 sq/ft located on busy route 8. Solid daily traffic count.

    Michael Hernandez 360BERKSHIRE REALTY GROUP

    185 Columbia St, Adams, MA 01220

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, 01238 and 01027.
How to Rent a Home