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Explore Similar Condos Within 10 Miles of Windsor, MA

  • 189 Red Barn Rd, Dalton, MA 01226
    189 Red Barn Rd, Dalton, MA 01226
    189 Red Barn Rd, Dalton, MA 01226
    /69

    $975,000

    • 4 Beds
    • 4 Baths
    • 3,876 Sq Ft

    189 Red Barn Rd, Dalton, MA 01226

    189 Red Barn Road is 3876 square feet of easy living. Solid oak floors, gas range, granite counter tops, custom cherry kitchen cabinets, surround sound, primary suite is located on the first level. The garden level, features two en-suite bedrooms and a wet bar. The home has private panoramic views and is a short walk to the sports complex.Silver Maple Farm is arguably the best and most desirable

    Buddy Lewis BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    189 Red Barn Rd, Dalton, MA 01226
  • 770 Summer St Unit 3A, Lee, MA 01238
    770 Summer St Unit 3A, Lee, MA 01238
    770 Summer St Unit 3A, Lee, MA 01238
    /43

    $759,000

    • 3 Beds
    • 2.5 Baths
    • 2,135 Sq Ft

    770 Summer St Unit 3A, Lee, MA 01238

    Welcome home to Lakeside condominiums at Foxhollow! An established condo community perfectly positioned between Lee/Lenox/Stockbridge close to all area attractions! Desirable ground level unit features easy living. Enjoy morning coffee on your spacious deck taking in open rolling lawns and mountain views. Open living/dining with fireplace, updated kitchen w quartz counters, stainless

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    770 Summer St Unit 3A, Lee, MA 01238
  • 770 Summer St Unit 5D, Lee, MA 01238
    770 Summer St Unit 5D, Lee, MA 01238
    770 Summer St Unit 5D, Lee, MA 01238
    /48

    $640,000

    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    770 Summer St Unit 5D, Lee, MA 01238

    Welcome to 5D Lakeside at Foxhollow - a beautifully updated 3-bedroom, 3-full-bath condo offering the perfect blend of modern comfort and classic Berkshire charm.Enjoy seasonal views of sparkling Laurel Lake from your enclosed summer porch, the ideal spot for morning coffee or evening gatherings. Inside, you'll find a thoughtfully updated kitchen and baths, a cozy wood-burning fireplace, and

    Paula McLean PAULA MCLEAN REALTORS INC.

    770 Summer St Unit 5D, Lee, MA 01238
  • 33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    /52

    $765,000

    • 5 Beds
    • 4.5 Baths
    • 3,381 Sq Ft

    33 Alpine Trail, Pittsfield, MA 01201

    Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and

    Cortney Dupont COHEN & WHITE ASSOCIATES

    33 Alpine Trail, Pittsfield, MA 01201
  • 19 Aspen Way, Pittsfield, MA 01201
    19 Aspen Way, Pittsfield, MA 01201
    19 Aspen Way, Pittsfield, MA 01201
    /41

    $989,000

    • 3 Beds
    • 3 Baths
    • 4,024 Sq Ft

    19 Aspen Way, Pittsfield, MA 01201

    Live the lifestyle you deserve in this stunning 4-year-young detached single family condominium offering over 4,000 square feet of luxury! This 3-bed, 3-bath home features a gourmet kitchen with quartz counters, custom cooktop and hood and double ovens. Perfect for the Chef of the family. The home gym with sauna, and a spacious walkout lower level with game room and bar is the perfect space for

    Victoria Standring LAMACCHIA REALTY, INC

    19 Aspen Way, Pittsfield, MA 01201
  • 520 State Rd Unit 202, North Adams, MA 01247
    520 State Rd Unit 202, North Adams, MA 01247
    520 State Rd Unit 202, North Adams, MA 01247
    /30

    $520,000

    • 1 Bed
    • 1 Bath
    • 990 Sq Ft

    520 State Rd Unit 202, North Adams, MA 01247

    Greylock WORKS is the mixed-use redevelopment of the historic Greylock Mills, originally built between 1872 and 1914. Located at the foot of Mt. Greylock, just three miles from Mass MoCA, the Clark Art Institute, and Williams College Museum of Art, amidst the cultural and recreational hub where Massachusetts, New York, and Vermont converge. The 240,000 square foot revitalization already features

    Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

    520 State Rd Unit 202, North Adams, MA 01247
  • 37 Corey Rd Unit 843, Hancock, MA 01237
    37 Corey Rd Unit 843, Hancock, MA 01237
    37 Corey Rd Unit 843, Hancock, MA 01237
    /26

    $429,900

    • 2 Beds
    • 2 Baths
    • 1,004 Sq Ft

    37 Corey Rd Unit 843, Hancock, MA 01237

    Totally turnkey opportunity for a beautifully updated unit in the heart of Village Center. Located on the second floor of the Welcome Center building, this much-loved unit offers two spacious bedrooms, two full bathrooms, a well-equipped kitchen, washer dryer, dedicated parking spot and private ski locker. Walk out your front door to skiing, dining, hiking, gym, hot tubs and pools. Staying in?

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 843, Hancock, MA 01237
  • 37 Corey Rd Unit 862, Hancock, MA 01237
    37 Corey Rd Unit 862, Hancock, MA 01237
    37 Corey Rd Unit 862, Hancock, MA 01237
    /27

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,130 Sq Ft

    37 Corey Rd Unit 862, Hancock, MA 01237

    Looking for a corner unit at JJ's lodge? This 3 bedroom 2 full bath unit is literally steps away from the private locker room and walk out to the Berkshire Express. Beautiful distant Mountain vistas and views of the bunny hill where you can watch your kids learn how to ski and snowboard all from your private balcony! Multiple beds for family and friends. The unit has central AC and Heating with

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 862, Hancock, MA 01237
  • 1052 Beaver Pond Meadows, Hancock, MA 01237
    1052 Beaver Pond Meadows, Hancock, MA 01237
    1052 Beaver Pond Meadows, Hancock, MA 01237
    /38

    $299,000 Open Sun 10AM - 11:30AM

    • 3 Beds
    • 2 Baths
    • 1,634 Sq Ft

    1052 Beaver Pond Meadows, Hancock, MA 01237

    Charming 3-Bedroom Country Condo with Scenic ViewsEscape the hustle and embrace the tranquility of country living with this beautifully maintained 3-bedroom, 2-bathroom condo, nestled in a peaceful rural setting. Perfect for families, retirees, or weekend getaways, this home offers a perfect blend of comfort, style, and natural beauty.Spacious Open Floor Plan: Enjoy a sun-filled living and dining

    Lisa Mendel BURNHAM GOLD REAL ESTATE, LLC

    1052 Beaver Pond Meadows, Hancock, MA 01237
  • 37 Corey Rd Unit 85, Hancock, MA 01237
    37 Corey Rd Unit 85, Hancock, MA 01237
    37 Corey Rd Unit 85, Hancock, MA 01237
    /31

    $265,000

    • 2 Beds
    • 1 Bath
    • 842 Sq Ft

    37 Corey Rd Unit 85, Hancock, MA 01237

    Welcome to your idyllic escape in the Berkshires. This elegant 2 bedroom 1 bath Country Village residence is located at Jiminy Peak Mountain Resort. Designed with vaulted ceilings and a wood burning fireplace, this inviting space is perfect for cozy winter evenings after a day on the slopes or a summer hike. Step outside to your own deck for summer BBQ's, morning yoga with a fresh cup of coffee,

    Laura Arseneau PAULA MCLEAN REALTORS INC.

    37 Corey Rd Unit 85, Hancock, MA 01237
  • 37 Corey Rd Unit 526, Hancock, MA 01237
    37 Corey Rd Unit 526, Hancock, MA 01237
    37 Corey Rd Unit 526, Hancock, MA 01237
    /18

    $154,000

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 526, Hancock, MA 01237

    At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 526, Hancock, MA 01237
  • 25 Taft St, North Adams, MA 01247
    25 Taft St, North Adams, MA 01247
    25 Taft St, North Adams, MA 01247
    /18

    $300,000

    • 2 Beds
    • 1.5 Baths
    • 1,568 Sq Ft

    25 Taft St, North Adams, MA 01247

    Experience maintenance-free living in this stunning 3-bedroom, 1.5-bath townhouse, meticulously renovated to blend contemporary design with practicality. The open floor plan showcases exposed brick and stunning wood laminate flooring, complemented by energy-efficient stainless-steel appliances that enhance everyday living. Enjoy the convenience of flat, easy parking with a covered carport and

    Gary Fuls Jr RE/MAX Transitions

    25 Taft St, North Adams, MA 01247
  • 9074 Mountainside Dr, Hancock, MA 01237
    9074 Mountainside Dr, Hancock, MA 01237
    9074 Mountainside Dr, Hancock, MA 01237
    /25

    $390,000

    • 2 Beds
    • 2 Baths
    • 1,035 Sq Ft

    9074 Mountainside Dr, Hancock, MA 01237

    Your Ultimate Year-Round Escape Awaits at Jiminy Peak!Move-in ready, adventure-ready! This pristine 2-bed, 2-bath end-unit condo at Jiminy Peak Mountain Resort isn't just a home--it's your passport to four seasons of Berkshires fun.Ideally located just 30 minutes to Tanglewood in Lenox, 20 minutes to the Clark in Williamstown, and 10 minutes to the base of Mount Greylock, this mountain retreat

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    9074 Mountainside Dr, Hancock, MA 01237
  • 14 Alpine Trail Unit 14, Pittsfield, MA 01201
    14 Alpine Trail Unit 14, Pittsfield, MA 01201
    14 Alpine Trail Unit 14, Pittsfield, MA 01201
    /29

    $692,000

    • 4 Beds
    • 3.5 Baths
    • 3,296 Sq Ft

    14 Alpine Trail Unit 14, Pittsfield, MA 01201

    Welcome to your dream mountain retreat! This stunning end unit in a community of 96 units offers an unparalleled lifestyle for outdoor enthusiasts. With effortless access to ski trails right from your back screened-in porch, you can hit the slopes at Bousquet Mountain anytime you desire.Spanning over 3,200 square feet, this 4-bedroom, 3.5-bath condo has a spacious three-level layout. Step inside

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    14 Alpine Trail Unit 14, Pittsfield, MA 01201
  • 1541 Green River Rd Unit 1, Williamstown, MA 01267
    1541 Green River Rd Unit 1, Williamstown, MA 01267
    1541 Green River Rd Unit 1, Williamstown, MA 01267
    /31

    $624,900

    • 3 Beds
    • 1.5 Baths
    • 1,986 Sq Ft

    1541 Green River Rd Unit 1, Williamstown, MA 01267

    Welcome to 1541 Green River Road -- where classic construction meets modern living! This beautifully updated condo offers the best of both worlds: the solid craftsmanship of a bygone era, reimagined with today's must-have upgrades.Step inside to discover a bright floor plan featuring stylish flooring, designer kitchen finishes, and a refreshed, contemporary bathroom. Enjoy peace of mind with

    Kim Burnham BURNHAM GOLD REAL ESTATE, LLC

    1541 Green River Rd Unit 1, Williamstown, MA 01267
  • 520 State Rd Unit 401, North Adams, MA 01247
    520 State Rd Unit 401, North Adams, MA 01247
    520 State Rd Unit 401, North Adams, MA 01247
    /39

    $1,495,000

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    520 State Rd Unit 401, North Adams, MA 01247

    Greylock WORKS is the mixed-use redevelopment of the historic Greylock Mills, originally built between 1872 and 1914. Located at the foot of Mt. Greylock, just three miles from Mass MoCA, the Clark Art Institute, and Williams College Museum of Art, amidst the cultural and recreational hub where Massachusetts, New York, and Vermont converge.The 240,000 square foot revitalization already features

    Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

    520 State Rd Unit 401, North Adams, MA 01247
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /26

    $299,000

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    Unlisted Address

    Discover the perfect opportunity in the heart of downtown Lenox with a Church Street view! This charming condo is an ideal choice for investors, second homeowners, or those seeking a convenient lifestyle. This unit boasts two bedrooms, two full baths, beautiful wood floors, and a cozy gas fireplace. You will immediately have access to various shops, restaurants, and Tanglewood just minutes away!

    Jessica Rizzo LAMACCHIA REALTY, INC

    Unlisted Address
  • 37 Corey Rd Unit 844, Hancock, MA 01237
    37 Corey Rd Unit 844, Hancock, MA 01237
    37 Corey Rd Unit 844, Hancock, MA 01237
    /22

    $350,000

    • 2 Beds
    • 2 Baths
    • 1,006 Sq Ft

    37 Corey Rd Unit 844, Hancock, MA 01237

    Here is a unique opportunity to own a large and bright 2 bedroom/2 bath condo in the Paul Major Welcome Center. It is steps to the lifts as well as other amenities like restaurants and shopping. The unit has its own storage locker, parking space and owner's closet for your convenience. This unit features really beautiful views of the mountains and the ski slopes. Primary bathroom has double sinks

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 844, Hancock, MA 01237
  • 520 State Rd Unit 309, North Adams, MA 01247
    520 State Rd Unit 309, North Adams, MA 01247
    520 State Rd Unit 309, North Adams, MA 01247
    /30

    $710,000

    • 2 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    520 State Rd Unit 309, North Adams, MA 01247

    Greylock WORKS is the mixed-use redevelopment of the historic Greylock Mills, originally built between 1872 and 1914. Located at the foot of Mt. Greylock, just three miles from Mass MoCA, the Clark Art Institute, and Williams College Museum of Art, amidst the cultural and recreational hub where Massachusetts, New York, and Vermont converge. The 240,000 square foot revitalization already features

    Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

    520 State Rd Unit 309, North Adams, MA 01247
  • 15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
    15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
    15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
    /18

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201

    Looking to have your new home in the new year? This Berkshire Country Meadows single-level living condo will be ready for summer 2025 occupancy! Construction is well underway for this 2000sf, 3 bedroom, 2 bath stand-alone condo, but there is still time to make your own personalized selections! Central a/c, natural gas heat, gas fireplace, hardwood floors, two car garage. The condo

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
  • 5 Aspen Way Unit 17, Pittsfield, MA 01201
    5 Aspen Way Unit 17, Pittsfield, MA 01201
    5 Aspen Way Unit 17, Pittsfield, MA 01201
    /20

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    5 Aspen Way Unit 17, Pittsfield, MA 01201

    Great opportunity to custom design your 2000 square foot free-standing condo home at Berkshire Country Meadows! This is one of only a few remaining sites in this established community. Close to Pontoosuc Lake and centrally located for all Berkshire attractions. Association has a club house with fitness equipment, pool and tennis. Select from several floor plans which feature a contemporary

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    5 Aspen Way Unit 17, Pittsfield, MA 01201
  • 9122 Mountainside Dr, Hancock, MA 01237
    9122 Mountainside Dr, Hancock, MA 01237
    9122 Mountainside Dr, Hancock, MA 01237
    /36

    $399,900

    • 2 Beds
    • 2 Baths
    • 1,346 Sq Ft

    9122 Mountainside Dr, Hancock, MA 01237

    This lower mountainside 2-bedroom 2 full bath unit comes furnished. Nicely renovated with granite countertops and stainless-steel appliances. Short walk to the slopes and restaurants. You have access to the pools during the summer months. This is an upstairs/downstairs unit. The main floor offers an updated full bath and full laundry room, fireplace. The upper level features a large full bath

    Kevin Moderski JIMINY REALTY

    9122 Mountainside Dr, Hancock, MA 01237
  • 37 Corey Rd Unit 634, Hancock, MA 01237
    37 Corey Rd Unit 634, Hancock, MA 01237
    37 Corey Rd Unit 634, Hancock, MA 01237
    /12

    $155,000

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 634, Hancock, MA 01237

    At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 634, Hancock, MA 01237
  • 55 Pomeroy Ave Unit 6, Pittsfield, MA 01201
    55 Pomeroy Ave Unit 6, Pittsfield, MA 01201
    55 Pomeroy Ave Unit 6, Pittsfield, MA 01201
    /20

    $219,900

    • 2 Beds
    • 1 Bath
    • 867 Sq Ft

    55 Pomeroy Ave Unit 6, Pittsfield, MA 01201

    Historic Pomeroy Manor presents a chance to own a slice of Pittsfield, Massachusetts history. This city, celebrated for its 1800s industry, once had the president of E.D. Jones & Sons, a renowned paper machine factory, residing in what was considered a modest home. Today, this residence is part of the ''Upstreet Cultural District.'' The Carriage House, now transformed into a condominium, offers

    Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

    55 Pomeroy Ave Unit 6, Pittsfield, MA 01201
  • 33 Maplewood Ave Unit 103, Pittsfield, MA 01201
    33 Maplewood Ave Unit 103, Pittsfield, MA 01201
    33 Maplewood Ave Unit 103, Pittsfield, MA 01201
    /33

    $199,900

    • 2 Beds
    • 1 Bath
    • 1,028 Sq Ft

    33 Maplewood Ave Unit 103, Pittsfield, MA 01201

    If you are looking for easy one-level living - don't miss this opportunity! The Maplewood is an elegant condo conversion consisting of eighteen units centrally located in downtown Pittsfield. You'll enjoy this light-filled corner/end unit on the first floor. High ceilings and an open-living plan give a very spacious feel to this two-bedroom unit. Kitchen with granite and stainless, hardwood

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    33 Maplewood Ave Unit 103, Pittsfield, MA 01201
  • 37 Corey Rd Unit 212, Hancock, MA 01237
    37 Corey Rd Unit 212, Hancock, MA 01237
    37 Corey Rd Unit 212, Hancock, MA 01237
    /19

    $159,900

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 212, Hancock, MA 01237

    At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 212, Hancock, MA 01237
Massachusetts Windsor

Condos for Sale in Windsor, MA

Why Live in Windsor

Windsor is a rural neighborhood in the Berkshires, offering a tranquil lifestyle 20 miles south of the Vermont border. With a tiny population, Windsor is ideal for those seeking a quiet, off-the-beaten-path experience. Homes range from off-grid cottages to spacious retreats with hillside views, and styles include ranch-style homes, saltboxes, and farmhouses with barns or horse pastures. Outdoor recreation is abundant, with Tamarack Hollow Nature & Cultural Center providing guided hikes and snowshoe treks, Wahconah Falls State Park featuring a dog-friendly trail to a 40-foot waterfall, and Windsor State Forest offering year-round activities like hiking, hunting, and snowmobiling. Notchview focuses on cross-country skiing and biking. Windsor is car-dependent, with Berkshire Trail connecting it to other communities. Emergency care is 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 homemade samosas available at Sanger General Store and groceries at Old Creamery Co-Op in Cummington. Shire Tavern in Dalton offers beer and upscale pub fare in a cozy, farmhouse-style setting. The fairgrounds in Cummington host events like the Hampshire County 4-H Fair and the Massachusetts Sheep and Woolcraft Fair, with the Cummington Fair providing family-friendly entertainment each August. Windsor has low crime risk areas compared to the national average.
Learn more about living in Windsor

Home Trends in Windsor, MA

On average, homes in Windsor, MA sell after 10 days on the market compared to the national average of 50 days. The median sale price for homes in Windsor, MA over the last 12 months is $135,000, down 77% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$135,000
Median Single Family Sale Price
$297,500
Average Price Per Sq Ft
$226
Number of Homes for Sale
1
Last 12 months Home Sales
3
Months of Supply
4.00
Median List Price
$287,000
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
-77%
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