Section Image

Explore Similar Condos Within 10 Miles of Windsor, MA

  • 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
  • 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
    /35

    $415,000

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

    9122 Mountainside Dr, Hancock, MA 01237

    Ready for move in just bring your skis and toothbrush. 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

    Kevin Moderski JIMINY REALTY

    9122 Mountainside Dr, Hancock, MA 01237
  • 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
  • 37 Corey Rd Unit 9074, Hancock, MA 01237
    37 Corey Rd Unit 9074, Hancock, MA 01237
    37 Corey Rd Unit 9074, Hancock, MA 01237
    /23

    $395,000

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

    37 Corey Rd Unit 9074, Hancock, MA 01237

    Popular two-bedroom two-bathroom unit on one level. This upper end unit comes nicely furnished, contemporary design with vaulted ceiling with fan, spacious private deck and two car parking. Recently renovated with granite countertops, stainless steel appliances, new bathrooms and updated living room with wood burning fireplace. This is a turnkey opportunity. Just bring your toothbrush and skis.

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 9074, Hancock, MA 01237
  • 165 Kemble St Unit 2, Lenox, MA 01240
    165 Kemble St Unit 2, Lenox, MA 01240
    165 Kemble St Unit 2, Lenox, MA 01240
    /11

    $1,400,000

    • 1 Bed
    • 1.5 Baths
    • 1,109 Sq Ft

    165 Kemble St Unit 2, Lenox, MA 01240

    Discover luxury living at Canyon Ranch with this 1-bedroom condo, boasting a chef's kitchen with marble countertops, and an expansive great room with a marble gas fireplace. Savor your morning coffee on the serene private balcony. The primary suite is a retreat with a spa-like marble bathroom, ample walk-in closet, and a cozy fireplace. Exclusive resort membership provides access to unparalleled

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    165 Kemble St Unit 2, Lenox, MA 01240
  • 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
    /45

    $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
  • 37 Corey Rd Unit 636, Hancock, MA 01237
    37 Corey Rd Unit 636, Hancock, MA 01237
    37 Corey Rd Unit 636, Hancock, MA 01237
    /3

    $149,900

    • 1 Bed
    • 1 Bath
    • 520 Sq Ft

    37 Corey Rd Unit 636, 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 636, Hancock, MA 01237
  • 37 Corey Rd Unit 826, Hancock, MA 01237
    37 Corey Rd Unit 826, Hancock, MA 01237
    37 Corey Rd Unit 826, Hancock, MA 01237
    /23

    $299,990

    • 1 Bed
    • 1 Bath
    • 655 Sq Ft

    37 Corey Rd Unit 826, Hancock, MA 01237

    NEW TO THE MARKET!!! An affordable condo in Village Center...1 bed 1 full bath with a loft. Ski locker and private parking space included. Just walk off the slopes to your condo. Grab and bite to eat...check some TV...warm up with your wood burning fireplace. Park your car and leave it for the weekend. This one will not last long. Owner has made numerous upgrades. Call today!

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 826, Hancock, MA 01237
  • 127 Alpine Trail, Pittsfield, MA 01201
    127 Alpine Trail, Pittsfield, MA 01201
    127 Alpine Trail, Pittsfield, MA 01201
    /54

    $939,000

    • 5 Beds
    • 4.5 Baths
    • 3,700 Sq Ft

    127 Alpine Trail, Pittsfield, MA 01201

    This unit is absolutely stunning! It has breathtaking views of the mountains and spacious open common areas filled with natural light. The main Great room has soaring ceilings, a cozy gas fireplace, wood floors, and direct access to your private screened porch and deck. The kitchen, dining area, and first-floor primary en-suite are all open and inviting. Additionally, there is a main level

    Cortney Dupont COHEN & WHITE ASSOCIATES

    127 Alpine Trail, Pittsfield, MA 01201
  • 34 Church St Unit 2, Lenox, MA 01240
    34 Church St Unit 2, Lenox, MA 01240
    34 Church St Unit 2, Lenox, MA 01240
    /27

    $320,000

    • 2 Beds
    • 1.5 Baths
    • 800 Sq Ft

    34 Church St Unit 2, Lenox, MA 01240

    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!

    34 Church St Unit 2, Lenox, MA 01240
  • 44 Churchill Crest Unit 44, Pittsfield, MA 01201
    44 Churchill Crest Unit 44, Pittsfield, MA 01201
    44 Churchill Crest Unit 44, Pittsfield, MA 01201
    /26

    $279,900

    • 2 Beds
    • 2 Baths
    • 1,227 Sq Ft

    44 Churchill Crest Unit 44, Pittsfield, MA 01201

    Exceptionally maintained two bedroom and two bathroom condo. An end unit located in Churchill Crest Condominium Association that offers exterior maintenance, cable/internet, and a heated pool with pavilion. Boasting a spacious living room with a wood burning fireplace, hardwood floors, and a private balcony. Leading into a formal dining room off the kitchen with a breakfast bar and ample cabinets

    Cory Evangelisto NOCHER REALTY

    44 Churchill Crest Unit 44, Pittsfield, MA 01201
  • 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
  • 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

    $144,999

    • 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
    /28

    $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 83, Hancock, MA 01237
    37 Corey Rd Unit 83, Hancock, MA 01237
    37 Corey Rd Unit 83, Hancock, MA 01237
    /26

    $249,900

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    37 Corey Rd Unit 83, Hancock, MA 01237

    Freshly renovated with new floors, new kitchen, new bath with a walk-in shower, new washer/dryer, updated fireplace. This 2-bedroom unit is turnkey and ready to either rent or use or both! Just bring your toothbrush and ski equipment. New mini split for heating and air conditioning the entire unit. You can also light fire in the wood burning fireplace on those cold winter nights. Short walk

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 83, Hancock, MA 01237
  • 37 Corey Rd Unit 212, Hancock, MA 01237
    37 Corey Rd Unit 212, Hancock, MA 01237
    37 Corey Rd Unit 212, Hancock, MA 01237
    /18

    $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
  • 880 East St Unit 16D, Lee, MA 01238
    880 East St Unit 16D, Lee, MA 01238
    880 East St Unit 16D, Lee, MA 01238
    /36

    $549,900

    • 3 Beds
    • 3 Baths
    • 2,087 Sq Ft

    880 East St Unit 16D, Lee, MA 01238

    A Dream retreat tucked away in Lee at the Village at October Mountain! This charming end unit condo boasts 3 bedrooms, 3 bathrooms, and an array of modern amenities and modern design for comfort, relaxation and style. New Wood floors lead you through the open-concept living space, that is flooded with natural light. The kitchen features granite countertops, sleek stainless appliances, and

    Jason Nocher NOCHER REALTY

    880 East St Unit 16D, Lee, MA 01238
Massachusetts Windsor

Condos for Sale in Windsor, MA

About Windsor

Out in the Berkshires, residents in Windsor enjoy a slow-paced lifestyle 20 miles south of the Vermont border. Surrounded by trees in every direction, “Windsor has a tiny population,” says Lindsey Schmid, Senior Vice President of Tourism and Marketing at 1Berkshire, a business and lifestyle resource for the area. “It’s pretty quiet and sleepy for people looking for that real rural experience.” Homeowners get to live off the beaten path, whether in an off-grid cottage or in a 5,000 square-foot retreat with hillside views. “It's not a far drive t ...

Learn more about living in Windsor

Home Trends in Windsor, MA

On average, homes in Windsor, MA sell after 34 days on the market compared to the national average of 48 days. The average sale price for homes in Windsor, MA over the last 12 months is $599,780, up 39% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)
$439,900
Median Single Family Price
$439,900
Average Price Per Sq Ft
$248
Last 12 months Home Sales
5
Median List Price
$439,000
Median Discount From 1st List Price
-3%
Median Home Sale Price YoY Change
-19%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group