Berkshire, MA Homes

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  /17

  $179,000

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  49 Access Rd Unit 3b, Windsor, MA 01270

  This charming rustic seasonal lake cottage, rebuilt in 2011 with structural enhancements, replacement windows, and a large side deck, is a cozy retreat nestled on 1.24 wooded acres by Windsor Pond. The interiors are adorned with knotty pine, giving it a warm and inviting feel harkening to an era past. With two comfy bedrooms, a wood stove to keep you warm on chilly nights, a spacious screened

  

  Lisa Carroll

  Delap Real Estate LLC

  (413) 741-2269

  49 Access Rd Unit 3b, Windsor, MA 01270
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  Explore Windsor

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  /52

  $435,000 Sold Jul 10, 2025

  • 2,444 Sq Ft
  • $178/SF
  • 95 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1850

  576 North St, Windsor, MA 01270

  Look no further, this charming farmhouse nestled on almost four acres is waiting foryou. Relax on the screened back porch or have morning coffee in the skylight drenched sunroom, you may view the wildlife that travels through the state forest, which borders the property. The home features a living room fireplace, skylights and sunroom, cedar closet and central vac. The grounds offer lots of

  John Ciepiela BISHOP WEST REAL ESTATE

  576 North St, Windsor, MA 01270
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  /34

  Est $545,772 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  140 Hill Cemetery Rd, Windsor, MA 01270

  140 Hill Cemetery Rd, Windsor, MA 01270
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  /37

  $329,900

  • 2 Beds
  • 1 Bath
  • 1,158 Sq Ft

  1621 Peru Rd, Windsor, MA 01270

  New to the Market - Here is a True Sportsman's Retreat or Vacation Home! Set on 22 Private Acres in Windsor, MA this Off-The-Grid property is ideal for the outdoor enthusiast. The unfinished home offers a solid start for a Hunting Cabin or Four Season Getaway. Surrounded by nature, the land is alive with Bear, Deer, Moose and more - Offering Prime Hunting or Snowmobiling as the trails are right

  Kim Dodge Kim Grant-Dodge

  1621 Peru Rd, Windsor, MA 01270
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  /53

  $505,000 Sold Jun 27, 2025

  • 1,562 Sq Ft
  • $323/SF
  • 27 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1993

  470 Peru Rd, Windsor, MA 01270

  Spacious 3-bedroom, 2.5-bath ranch offering over 1,500 sq. ft. of living space on 22+ peaceful acres. This well-maintained home features a finished basement with a cozy fireplace, perfect for relaxing or entertaining. The property includes a large two-bay barn, a charming sugar shack, and a network of scenic trails ideal for outdoor enjoyment. Whether you're looking for space to explore, hobby

  John Ciepiela BISHOP WEST REAL ESTATE

  470 Peru Rd, Windsor, MA 01270
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  /4

  Est $529,280 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,042 Sq Ft

  884 Cheshire Rd, Windsor, MA 01270

  884 Cheshire Rd, Windsor, MA 01270
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  /69

  $1,195,000

  • 4 Beds
  • 3 Baths
  • 3,541 Sq Ft

  1828 Flintstone Rd, Windsor, MA 01270

  Welcome to Stone Hill - Your Private Oasis with Spectacular Views overlooking the Berkshire Hill Towns. Escape to a world of tranquility and luxury where nature's beauty meets exquisite living. Nestled on a 9.45 acre property, this spectacular estate offers the ultimate retreat for those seeking privacy and serenity. Immerse yourself in the beauty of the Chalet Wildlife Management Area

  Matt Carlino MACCARO REAL ESTATE

  1828 Flintstone Rd, Windsor, MA 01270
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  /19

  $135,000 Sold Jun 05, 2025

  • 1,200 Sq Ft
  • $112/SF
  • 25 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1952

  1952 Old Route 9, Windsor, MA 01270

  An Ideal Project for the Right BuyerThis 2-bedroom, 1-bath Cape fixer-upper is an incredible opportunity for buyers who are looking for a project that will allow them to make their mark on a home while enjoying the rewards of renovation. With its solid foundation, charming features, and endless possibilities for expansion, this property offers the perfect blank canvas to bring your vision to

  Kolleen Schmitt BISHOP WEST REAL ESTATE

  1952 Old Route 9, Windsor, MA 01270
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  /38

  Est $563,112 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  1387 E Windsor Rd, Windsor, MA 01270

  1387 E Windsor Rd, Windsor, MA 01270
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  /24

  $325,000

  • 1 Bed
  • 1 Bath
  • 1,082 Sq Ft

  961 Peru Rd, Windsor, MA 01270

  Finish this super insulated house to your liking. Seller had to quit due to personal issues. High end kitchen cabinets are bought but not installed. Tub is installed. Sheet rock needs to be taped and spackled. Rough electric and plumbing are done. Super insulated tiny house for guests or separate home office has electricity but no plumbing. All work was permitted and inspected. Please see

  Carla Ness Delap Real Estate LLC

  961 Peru Rd, Windsor, MA 01270
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  /48

  $397,500 Sold Jun 03, 2025

  • 2,500 Sq Ft
  • $159/SF
  • 342 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1982

  1523 North St, Windsor, MA 01270

  NEW PRICE!!! Enjoy country living just minutes from town. Enjoy the space the privacy of every inch of this 3.75 acres and your 4 bed/2 ba New England farmhouse. Large rooms, cozy wood burning fireplace in the living/dining and woodstove in your spacious renovated kitchen (2021). Lge deck to take in the views, 3/4 bath down w/laundry. Upstairs there's 4 bedrooms & a full bath, updated floors on

  Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

  1523 North St, Windsor, MA 01270
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  /57

  Est $420,295 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft

  1600 North St, Windsor, MA 01270

  1600 North St, Windsor, MA 01270
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  /35

  $485,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  1689 E Windsor Rd, Windsor, MA 01270

  Country colonial home which has never been on the market. Built by the sellers and their family of contractors. Situated on a picturesque corner lot with a spring & brook-fed pond. Step inside from the new deck to find a cherry wood floor, updated kitchen with granite countertops and a one of a kind island. The dining room and sunny living space boast hickory wood floors and Anderson windows. A

  Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

  1689 E Windsor Rd, Windsor, MA 01270
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  /42

  $425,000 Sold May 23, 2025

  • 1,472 Sq Ft
  • $289/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  775 North St, Windsor, MA 01270

  First time on the market is this lovely ranch style home on 2.4 acres with westerly views. Bordering state land ensuring your peace & privacy for years to come. This meticulously maintained home offers one level of living combining the perfect blend of comfort and serenity. The heart of this home is the large, inviting eat-in kitchen featuring up-to-date stainless appliances, ample cabinetry,

  Cindy Carrigan Lamacchia Realty, Inc.

  775 North St, Windsor, MA 01270
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  /39

  Est $633,548 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,350 Sq Ft

  733 North St, Windsor, MA 01270

  733 North St, Windsor, MA 01270
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  /35

  $549,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 1,914 Sq Ft

  788 Flintstone Rd, Windsor, MA 01270

  Experience the ideal mix of comfort, privacy, and natural beauty on this beautifully maintained 19-acre property. Quietly tucked away, yet just minutes from the cultural and recreational attractions of the Berkshires, this move-in ready home offers serene country living with modern convenience.Built and cared for by the original owners, the home features 4 spacious bedrooms, 3 full bathrooms, and

  Laiken Rapisarda LAMACCHIA REALTY, INC

  788 Flintstone Rd, Windsor, MA 01270
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  /50

  $460,000 Sold Dec 19, 2024

  • 2,240 Sq Ft
  • $205/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2004

  130 High St Hill Rd, Windsor, MA 01270

  Discover your dream home in Windsor, set on over 5 acres of serene landscape! This charming colonial has it all, nestled in a private & efficient setting, this home is ready for its next owners. Inside, enjoy freshly painted rooms, beautiful red birch hard wood floors & high efficiency wood stove. Benefit from owned solar panels and a home generator for added efficiency & peace of mind. Enjoy

  Laiken Rapisarda LAMACCHIA REALTY, INC

  130 High St Hill Rd, Windsor, MA 01270
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  /42

  Est $519,523 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,241 Sq Ft

  1496 North St, Windsor, MA 01270

  1496 North St, Windsor, MA 01270
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  /18

  $17,000 Sold Dec 17, 2024

  • Land
  • 2.17 Acres
  • $7,834 per Acre

  • 7 Days On Market

  331 Shaw Rd, Windsor, MA 01270

  Mostly level and partially cleared 2.17 acre lot. Serene and tranquil surroundings. Berkshires camping retreat? Hunting getaway? Recreational? Great location to enjoy four season outdoor recreation and all that nature has to offer. Easy access to all cultural and natural amenities in and around the Berkshires!

  Deb Trzcinski Steepleview Realty

  331 Shaw Rd, Windsor, MA 01270
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  /35

  Est $477,521 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,500 Sq Ft

  105 High St Hill Rd, Windsor, MA 01270

  105 High St Hill Rd, Windsor, MA 01270
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  /29

  $290,000 Sold Oct 16, 2024

  • 1,014 Sq Ft
  • $286/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1965

  143 Windsor Bush Rd, Cummington, MA 01026

  Country chalet on 3+ acres with fresh water pond in the Berkshires! Take advantage of this unique opportunity to own this 2 bedroom, 2 bath home with incredible storybook-like charm. Close to route 9 for easy access to the Berkshires to the west or the 5 college area to the east. State forest lands nearby for your hiking enjoyment including Windsor Jambs at Windsor State Forest located minutes

  Altaluxre Group William Pitt Sotheby's International Realty

  143 Windsor Bush Rd, Cummington, MA 01026
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  /21

  Est $508,660 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,716 Sq Ft

  235 High St Hill Rd, Windsor, MA 01270

  235 High St Hill Rd, Windsor, MA 01270
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  /38

  $439,900 Sold Oct 15, 2024

  • 1,782 Sq Ft
  • $247/SF
  • 5 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1952

  877 Massachusetts 9, Windsor, MA 01270

  Don’t miss your chance to escape from the hubbub of life to your very own oasis set on 22+ picturesque wooded acres. The absolute BEST of what the Hilltowns and Berkshires have to offer. Sit on the Goshen stone patio and gaze into your fish pond or enjoy the stunning view of the milky way from your hot tub. This property holds unlimited potential for your garden or homestead with fruit trees,

  Holly Berry Olde Towne Realty

  877 Massachusetts 9, Windsor, MA 01270
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  /107

  Est $486,261 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  344 Worthington Rd, Windsor, MA 01270

  344 Worthington Rd, Windsor, MA 01270
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  /56

  $410,000 Sold Aug 22, 2024

  • 1,490 Sq Ft
  • $275/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  102 Monahan Rd, Windsor, MA 01270

  We are offering a Ranch style home in a peaceful country setting on a dead end road! The home is perfectly set on 8.4 acres of largely wooded land with a nicely manicured lawn that is large enough for year round enjoyment. This 3 bedroom 2 bath ranch has been tastefully renovated recently. Some of the updates include fresh paint throughout, newer laminate floors throughout and metal roof. The

  Doug Collins LAMACCHIA REALTY, INC

  102 Monahan Rd, Windsor, MA 01270
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  /52

  Est $478,507 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,080 Sq Ft

  1540 E Windsor Rd, Windsor, MA 01270

  1540 E Windsor Rd, Windsor, MA 01270
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  /24

  $210,000 Sold Aug 14, 2024

  • 975 Sq Ft
  • $215/SF
  • 42 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1975

  1430 Old Route 9, Windsor, MA 01270

  Embrace the serenity of nature as you come home to this cozy and cute 2-bedroom, 1-bath house, that offers beautiful natural wood cathedral ceiling and many updates throughout the house. Located on a quiet paved country road with bubbling river just across the street. Nestled in a peaceful setting, but only about 15 minutes to Pittsfield shopping centers. Visit to find out if this move-in-ready

  Ann Jerebtsov LAMACCHIA REALTY, INC

  1430 Old Route 9, Windsor, MA 01270
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  /34

  Est $739,206 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,102 Sq Ft

  1256 E Windsor Rd, Windsor, MA 01270

  1256 E Windsor Rd, Windsor, MA 01270
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  /2

  $439,900 Sold Oct 15, 2024

  • 1,782 Sq Ft
  • $247/SF
  • 69 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1952

  877 State Highway 9 --, Windsor, MA 01270

  Easy one level living with updated and kitchen and bath.

  Comparable Listing COMPARABLE LISTING ONLY

  877 State Highway 9 --, Windsor, MA 01270
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  /2

  Est $560,430 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft

  1411 North St, Windsor, MA 01270

  1411 North St, Windsor, MA 01270
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  /2

  $1,479,000 Sold Sep 26, 2024

  • 5,000 Sq Ft
  • $296/SF
  • 55 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1984

  249 Bates Rd, Windsor, MA 01270

  Discover Westview, a stunning retreat spanning 76 acres adjacent to Notchview Reservation, offering panoramic views.This contemporary hideaway boasts exceptional craftsmanship and thoughtful design.Inside, two kitchens feature expansive layouts, abundant natural light, and custom-built cabinets that adorn every room. The integration of granite, marble, and quartz countertops enhances elegance

  Elisha Poirier STONE HOUSE PROPERTIES, LLC

  249 Bates Rd, Windsor, MA 01270
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  /25

  Not Listed For Sale

  • 1 Bed
  • 350 Sq Ft

  1555 Bush Rd, Windsor, MA 01270

  1555 Bush Rd, Windsor, MA 01270
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  /42

  Est $618,195 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,596 Sq Ft

  696 River Rd, Windsor, MA 01270

  696 River Rd, Windsor, MA 01270
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  /25

  Est $46,560 Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /11

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /11

  Not Listed For Sale

  0 High Street Hill Rd Unit 73096931, Windsor, MA 01270

  0 High Street Hill Rd Unit 73096931, Windsor, MA 01270
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  /7

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
• 

  

  /42

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  140 Windigo Rd, Windsor, MA 01270

  140 Windigo Rd, Windsor, MA 01270
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  /4

  Est $87,185 Not Listed For Sale

  1136 Flintstone Rd, Windsor, MA 01270

  1136 Flintstone Rd, Windsor, MA 01270
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  /2

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,900 Sq Ft

  2065 River Rd, Windsor, MA 01270

  2065 River Rd, Windsor, MA 01270

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