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Explore Similar Homes Within 10 Miles of Windsor, MA

  • /12

    $1,600 total monthly price

    • 2 Beds
    • 1 Bath
    • 776 Sq Ft
    • Apartment for Rent

    30 Danforth Ave Unit 2, Pittsfield, MA 01201

    Updated 2 Bedroom 1 Bathroom. All Rooms Freshly Painted. New Kitchen Appliances: Refrigerator, Range, Stove. Bathroom Updated. Extra Space for Storage inBasement. Plenty of Parking. Large Yard. East to Show!

    Agent Photo

    Dawn Bongiorno

    Keller Williams Realty Boston South West

    (413) 366-3447

    30 Danforth Ave Unit 2, Pittsfield, MA 01201
  • /9

    $1,175 total monthly price

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    1 Edward Ave, Adams, MA 01220

    This 1 bed 1 bath apartment around the corner from the Forest Park Country Club is waiting for you! Property is owner-occupied. Minimum 1 year lease. First months rent and security is required to move in. Owner is responsible for lawn care, garbage pick up, heat, water and sewer. Tenant is responsible for electric, cable and internet. This is a NON smoking property. No pets (proper documentation

    Agent Photo

    Syrah Bradley

    BISHOP WEST REAL ESTATE

    (413) 366-3519

    1 Edward Ave, Adams, MA 01220
  • /8

    $1,500 per month plus fees

    7 North Street, Pittsfield MA

    1 Bed

    7 North St, Pittsfield, MA 01201

    Nicely updated, spacious apartment, Heat and Basic Cable included!Contact: or X 24Live in Pittsfields premier 7 North St. building, where architectural details of the past meet contemporary desires of today. This apartment, with updated kitchen and bathroom, has lots closet space, plenty of natural light with high ceilings, a dishwasher, and a WASHER AND DRYER RIGHT IN YOUR

    7 North St, Pittsfield, MA 01201
  • /7

    $1,075 total monthly price

    • 1 Bed
    • 1 Bath
    • Property for Rent

    235 East St Unit 27, Pittsfield, MA 01201

    Eastview Apartments. Featuring a studio apartment on the basement level with updated kitchen, and bathroom. Clean and move-in ready. Coin-op laundry, off street parking, and security on site. First months rent, last months rent, and half (1/2) security deposit due at lease signing. 2.6-3x Income required. Credit/Background checks (Minimum credit score of 660). Application fee of $45 is required

    Cory Evangelisto NOCHER REALTY

    235 East St Unit 27, Pittsfield, MA 01201
  • /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
  • /23

    $2,300 total monthly price

    • Condo for Rent

    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

    18 Morgan St Unit 1, Lenox, MA 01240
  • /17

    $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
  • /13

    $2,250 total monthly price

    • 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
  • /5

    $1,950 per month plus fees

    • 2 Beds
    • 1 Bath
    • 3,696 Sq Ft
    • Condo for Rent

    55 Worthen St Unit Left, Pittsfield, MA 01201

    Property Id: 2353540 A delightful 2-bedroom, 1-bathroom multi-family home nestled in the heart of Pittsfield, MA. This spacious property, boasting 3,696 square feet, features a blend of historic charm and modern convenience. The home showcases beautiful hardwood floors and cozy carpeted areas, creating a warm and inviting atmosphere. Enjoy the convenience of an in-unit washer and dryer,

    55 Worthen St Unit Left, Pittsfield, MA 01201
  • /8

    $1,800 total monthly price

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

    1 Fenn St, Pittsfield, MA 01201

    Most desirable ground floor, 1700 sqft office location located on the corner of North and Fenn Streets, in the heart of downtown Pittsfield. BRIGHT OPEN SPACE-GROUND FLOOR- TWO ENTRANCES- KITCHENETTE-PROFESSIONALLY MANAGED- ONE PRIVATE GATED PARKING SPACE

    Buddy Lewis BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    1 Fenn St, Pittsfield, MA 01201
  • /9

    $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
  • /28

    $1,400 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Property for Rent

    35 Livingston Ave, Pittsfield, MA 01201

    Well maintained and immaculately clean 2 bedroom, 1 bath apartment located on the first floor of an owner-occupied duplex. The unit offers comfortable layout with great natural light throughout. Bedroom 2 is on the smaller side but well suited for a sleeping space, guest bedroom or home office. The main living area and both bedrooms feature beautiful hardwood floors, adding warmth and character

    Stacy Hebb NOCHER REALTY

    35 Livingston Ave, Pittsfield, MA 01201
  • /30

    $1,850 total monthly price

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

    22 Allessio St Unit 22, 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 In-unit laundryEnclosed sunroom porchGreat water pressureBasement storage7 minutes from Berkshire Medical Center, 5 minutes from General

    22 Allessio St Unit 22, Pittsfield, MA 01201
  • /18

    $500 total monthly price

    • 0.5 Baths
    • 1,200 Sq Ft
    • Property for Rent

    212 South St, Pittsfield, MA 01201

    Incredible location for your business. Corner of South and Henry ave. just a short walk south of the busy North Street corridor. Four office spaces for lease. Rates are as follows: (Suite 1: 170 sq.ft./$700 mo., Suite 2: 100 sq.ft./$600 mo., Suite 3: 90 sq.ft./$500 mo., Suite 4: 250 sq.ft./$800/mo.) All utilities, including internet, is included. Private, off-street parking.

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    212 South St, Pittsfield, MA 01201
  • /2

    $1,600 - $1,800 total monthly price

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

    44 Robbins Ave, 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, Pittsfield, MA 01201
  • /14

    $1,200 total monthly price

    • 2 Beds
    • 1 Bath
    • Property for Rent

    19 Pleasant St Unit 2B, Adams, MA 01220

    Experience the perfect blend of historic charm and modern convenience in this beautifully refreshed 2-bedroom apartment. Located in the heart of downtown Adams, this apartment features gleaming hardwood floors and bright windows that flood the space with natural light. Every room has been updated with fresh paint, offering a clean, contemporary feel that's ready for you to move in. Living here

    Jason Nocher NOCHER REALTY

    19 Pleasant St Unit 2B, Adams, MA 01220
  • /7

    $1,750 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,050 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, new kitchen, full bath, a living room and offers off street parking.

    100 Church St Unit Cheshire, Cheshire, MA 01225
  • /16

    $2,100 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,215 Sq Ft
    • Condo for Rent

    49 Park St Unit 2, Adams, MA 01220

    Welcome to your new two-bedroom apartment, located in a charming historic downtown building in Adams. These thoughtfully designed apartments blend modern convenience with historic character, featuring soaring high ceilings, abundant natural light, hardwood floors, and contemporary finishes that complement the building's original charm. The kitchens offer stainless steel appliances, stylish

    Erin Vincent BISHOP WEST REAL ESTATE

    49 Park St Unit 2, Adams, MA 01220
  • /2

    $1,800 total monthly price

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

    44 Robbins Ave, 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, Pittsfield, MA 01201
  • /37

    $3,500 total monthly price

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

    1745 Massachusetts 2, Charlemont, MA 01370

    Location, Location!! Capture the energy of the iconic Mohawk Trail with this rare restaurant space located directly on Route 2. Boasting breathtaking river views and 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, and ample seating make it ideal for everything from nightly dining to

    Nicole Vadnais KELLER WILLIAMS REALTY

    1745 Massachusetts 2, Charlemont, MA 01370
  • /15

    $1,550 total monthly price

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

    319 Fenn St Unit 1, Pittsfield, MA 01201

    319 Fenn St Unit 1, Pittsfield, MA 01201
  • /24

    $2,150 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Apartment for Rent

    527 Main St Unit 1, Ashfield, MA 01330

    Charming 2/3 Bedroom Apartment in a Classic New England Village Home. Enjoy quintessential Main Street living in this inviting 1st floor apartment within a spacious Victorian home in the heart of a rural New England village. The unit features beautiful natural light from large windows, the warmth of wood floors and classic woodwork, and two generous bedrooms with one full bath. Recent updates

    Richard Binns Naples Realty Group

    527 Main St Unit 1, Ashfield, MA 01330
  • /26

    $1,300 total monthly price

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

    51 Orchard St Unit 1, Pittsfield, MA 01201

    51 Orchard St Unit 1, Pittsfield, MA 01201
  • /36

    $3,700 total monthly price

    • 5 Beds
    • 2 Baths
    • 2,416 Sq Ft
    • House for Rent

    527 Main St, Ashfield, MA 01330

    Charming 5-Bedroom Home in a Classic New England Village. Enjoy quintessential Main Street living in this welcoming New England residence, featuring abundant natural light from large windows, the warmth of wood floors and classic woodwork, and five spacious bedrooms with two full baths. Pellet stove in living room. Recent updates include fresh interior paint, and the grounds offer space for

    Richard Binns Naples Realty Group

    527 Main St, Ashfield, MA 01330
  • /10

    $2,000 total monthly price

    • 4 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    60 Cliff St Unit C, North Adams, MA 01247

    60 Cliff St Unit C, North Adams, MA 01247
  • /27

    $2,150 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,150 Sq Ft
    • Apartment for Rent

    527 Main St Unit 2, Ashfield, MA 01330

    Charming 2/3 Bedroom Apartment in a Classic New England Village Home. Enjoy quintessential Main Street living in this inviting 2nd-floor apartment within a spacious Victorian home in the heart of a rural New England village. The unit features beautiful natural light from large windows, the warmth of wood floors and classic woodwork, and two generous bedrooms with one full bath. Recent updates

    Richard Binns Naples Realty Group

    527 Main St Unit 2, Ashfield, MA 01330
  • /8

    $1,400 total monthly price

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

    59 Bartlett Ave Unit 5, Pittsfield, MA 01201

    59 Bartlett Ave is a well-maintained multi-unit rental property located in a residential area of Pittsfield. The building features several updated apartments, each offering clean finishes, practical layouts, and comfortable living spaces. With consistent upkeep and professional management, this property provides a stable and reliable housing option for quality tenants.Property

    59 Bartlett Ave Unit 5, Pittsfield, MA 01201
  • /19

    $2,600 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Apartment for Rent

    1 Rolling Hills Unit 10, Lenox, MA 01240

    Unique opportunity to rent a beautifully updated unit at the beautiful Rolling Hills in Lenox. 2 bathrooms and 2 full bathrooms. Gorgeous kitchen and finished room in the basement. Also two porches/patios. This unit could come furnished. 3 month minimum rental. November-March is $2,600 and April-October is $6,000

    Michele Purcell Lamacchia Realty, Inc.

    1 Rolling Hills Unit 10, Lenox, MA 01240
  • /8

    $1,350 total monthly price

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

    57 Bartlett Ave Unit 4, Pittsfield, MA 01201

    Welcome to 57 Bartlett Ave, a clean, updated, and well-maintained multi-unit property located in a quiet residential neighborhood of Pittsfield. This building offers a peaceful living environment while keeping you close to everything — grocery stores, bus routes, downtown conveniences, parks, and major roadways.Each unit in the building has been thoughtfully refreshed to provide

    57 Bartlett Ave Unit 4, Pittsfield, MA 01201
  • /8

    $1,800 total monthly price

    • 3 Beds
    • 1.5 Baths
    • 1,150 Sq Ft
    • Property for Rent

    170 Bracewell Ave Unit 1, North Adams, MA 01247

    Newly renovated apartment with new appliances, very spacious with an open floor plan, light interior color, and many windows offering a lot of natural light. Right next to Uno park and close to Mass Moca and MCLA college. Comes with a stack washer and dryer. Utilities not included. Cats are okay.

    Michael Hernandez 360BERKSHIRE REALTY GROUP

    170 Bracewell Ave Unit 1, North Adams, MA 01247
  • /11

    $900 total monthly price

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Apartment for Rent

    160 Main St Unit 2, Charlemont, MA 01339

    Nice 1st floor 1 bedroom apartment for rent on Main St in Charlemont. Freshly painted. Hardwood floors. No dogs. No smoking. $900 plus utilities. Landlord will do full background, CORI, and credit check.

    Josh Smith Ruggeri Real Estate

    160 Main St Unit 2, Charlemont, MA 01339
  • /10

    $1,500 total monthly price

    • 0.5 Baths
    • 682 Sq Ft
    • Property for Rent

    1404 North St, Pittsfield, MA 01201

    Lovely Lakeview Commercial Rental - Flexible Terms. Set your business up for success with this beautifully appointed commercial space featuring breathtaking sunset views over Pontoosuc Lake. Located on high-visibility Route 7, directly across from the newly revitalized Pontoosuc Park, this prime location offers maximum exposure and unbeatable charm. Inside, you'll find a thoughtfully designed

    Laiken Rapisarda LAMACCHIA REALTY, INC

    1404 North St, Pittsfield, MA 01201
  • /23

    $3,500 total monthly price

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

    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

    34 Galway Ct, Lenox, MA 01240
  • /14

    $1,900 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Condo for Rent

    49 Park St Unit 3, Adams, MA 01220

    If you're seeking a blend of historic charm and modern comfort, in a renovated one-two bedroom apartment in Adams, this is the perfect choice. With high ceilings, exposed ductwork, and a prime downtown location, these apartments offer a unique living experience that is both stylish and convenient.

    Erin Vincent BISHOP WEST REAL ESTATE

    49 Park St Unit 3, Adams, MA 01220
  • /16

    $395 total monthly price

    • Studio
    • 2 Baths
    • Property for Rent

    34 Depot St, Pittsfield, MA 01201

    Four (4) Modern Downtown Office Spaces for Lease ranging from 150 to 240 sq.ft. Two can be turned into connecting suites. Prices range from $395-$450 with everything included. Discover your next workspace in the heart of downtown Pittsfield! These modern office suites offer a bright, professional setting ideal for small businesses, startups, or solo professionals. Prime downtown location with

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    34 Depot St, Pittsfield, MA 01201
  • /9

    $1,000 total monthly price

    • 2 Baths
    • 1,300 Sq Ft
    • Property for Rent

    34 Depot St, Pittsfield, MA 01201

    Professional office (Suite L1) with 2 private entrances off of the private, main parking lot. Bright street level windows with 2 in suite bathrooms. Private, employee kitchenette, large, open common area with 3 semi-private offices. Great location within walking distance to North Street as well as restaurants and financial district of Downtown. Free parking in dedicated lot. Rate includes

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    34 Depot St, Pittsfield, MA 01201
  • /12

    $3,125 total monthly price

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

    34 Depot St, Pittsfield, MA 01201

    Well designed professional space that offers a reception area/desk, employee kitchen, 3 private offices, with common area meeting room with 2 shared bathrooms. Private and public parking available. Utilities are separate. Walking distance to ''North Street'' corridor in the financial district. Close to restaurants, court house, and everything downtown has to offer.

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    34 Depot St, Pittsfield, MA 01201
  • /6

    $450 total monthly price

    • 2 Baths
    • 240 Sq Ft
    • Property for Rent

    34 Depot St, Pittsfield, MA 01201

    Perfect for the professional who needs a private office located conveniently downtown, within walking distance to North Street corridor. Has a common area/waiting room shared with other professionals. Office directly off waiting room. Shared bathrooms down the hall. Private off-street parking.

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    34 Depot St, Pittsfield, MA 01201
  • /13

    $3,000 total monthly price

    • Condo for Rent

    257 S Main St, Hancock, MA 01237

    Charming and fully furnished country apartment available immediately featuring 2 beds and 1.5 baths. Warm and cozy in a well-cared for Owner occupied home, nestled in a serene rural area of Northern Berkshire. Close to Pittsfield and South Berkshire, it's just a few minutes away from Jiminy Peak skiing, with easy access to many other activities. Not only furnished, but heat, electric and internet

    Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

    257 S Main St, Hancock, MA 01237
  • /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 3/1/2026 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

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 neighborhoods in Windsor, MA for renters?
The most popular neighborhoods in Windsor, MA for renters are Ashfield and Florence.
What are the most popular zip codes in Windsor, MA for renters?
The most popular zip codes in Windsor, MA for renters include 01225, 01220, 01237, 01201 and 01330.
How to Rent a Home