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Explore Similar Condos Within 10 Miles of Windsor, MA

  • 520 State Rd Unit 208, North Adams, MA 01247
    520 State Rd Unit 208, North Adams, MA 01247
    520 State Rd Unit 208, North Adams, MA 01247
    /19

    $610,000

    • 1 Bed
    • 1.5 Baths
    • 1,150 Sq Ft

    520 State Rd Unit 208, North Adams, MA 01247

    Loft 208 at Greylock WORKS is a beautifully proportioned 1BR | 1.5BA + Study Berkshires residence set within the region's most celebrated mill conversion, offering 1,150 SF of refined, light-filled living. With 12.5-foot ceilings, expansive volume, and an elegant L-shaped living and dining area, the home blends the character of the original mill with elevated contemporary detailing to create a

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 798-5680

    520 State Rd Unit 208, North Adams, MA 01247
  • 1044 Beaver Pond Meadows, Hancock, MA 01237
    1044 Beaver Pond Meadows, Hancock, MA 01237
    1044 Beaver Pond Meadows, Hancock, MA 01237
    /42

    $319,900

    • 3 Beds
    • 2 Baths
    • 1,646 Sq Ft

    1044 Beaver Pond Meadows, Hancock, MA 01237

    Discover this Berkshires getaway in the private Beaver Pond Meadows community, complete with clubhouse and pool access! Just minutes from Jiminy Peak, this location offers a quieter, more relaxed alternative to Country Village. This fully furnished townhouse boasts a strong rental history and plenty of space to spread out, featuring three bedrooms and a full bath on the first level, a spacious

    Agent Photo

    Corey Bishop

    BISHOP WEST REAL ESTATE

    (855) 810-0060

    1044 Beaver Pond Meadows, Hancock, MA 01237
  • 18 Highcrest Rd, Lenox, MA 01240
    18 Highcrest Rd, Lenox, MA 01240
    18 Highcrest Rd, Lenox, MA 01240
    /46

    $1,420,000

    • 3 Beds
    • 4.5 Baths
    • 2,691 Sq Ft

    18 Highcrest Rd, Lenox, MA 01240

    Set within a private enclave of luxury homes just moments from downtown Lenox, this exceptional Berkshires condominium offers a rare combination of refined design, extraordinary privacy, and protected long-range views.Positioned at the far end of the development, the home benefits from owned development rights that safeguard sweeping easterly views of October Mountain and preserve the surrounding

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 319-9976

    18 Highcrest Rd, Lenox, MA 01240
  • 520 State Rd Unit 207, North Adams, MA 01247
    520 State Rd Unit 207, North Adams, MA 01247
    520 State Rd Unit 207, North Adams, MA 01247
    /18

    $675,000

    • 1 Bed
    • 1.5 Baths
    • 1,250 Sq Ft

    520 State Rd Unit 207, North Adams, MA 01247

    Set within the region's most celebrated mill conversion, Loft 207 at Greylock WORKS is a beautifully scaled 1BR | 1.5BA + Study Berkshires residence offering 1,250 SF of luminous, corner-exposure living. With 12.5-foot ceilings, expansive proportions, and oversized windows drawing natural light from two sides, this refined home blends industrial authenticity with contemporary design, creating a

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 350-1098

    520 State Rd Unit 207, North Adams, MA 01247
  • 520 State Rd Unit 402, North Adams, MA 01247
    520 State Rd Unit 402, North Adams, MA 01247
    520 State Rd Unit 402, North Adams, MA 01247
    /23

    $1,340,000

    • 2 Beds
    • 2 Baths
    • 2,110 Sq Ft

    520 State Rd Unit 402, North Adams, MA 01247

    Loft 402 is one of Greylock WORKS' most sought-after residences: a large, south-facing 2BR | 2BA + Study Berkshires loft with soaring 16-foot ceilings, luminous all-day light, and sweeping views of the hills. Set within the region's most celebrated mill conversion, this exceptional home blends architectural authenticity with contemporary design in a way that defines modern Berkshire living.The

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 725-4556

    520 State Rd Unit 402, North Adams, MA 01247
  • 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
  • 37 Corey Rd Unit 73, Hancock, MA 01237
    37 Corey Rd Unit 73, Hancock, MA 01237
    37 Corey Rd Unit 73, Hancock, MA 01237
    /24

    $255,000

    • 2 Beds
    • 2 Baths
    • 842 Sq Ft

    37 Corey Rd Unit 73, Hancock, MA 01237

    Country Village living...just listed is this recently renovated 2-bedroom unit which offers 2 full bathrooms also recently renovated. New floors throughout with no carpet. A gorgeous redone stone wood burning fireplace for those cold nights. A recently renovated kitchen with new appliances, granite countertops and wood cabinets. Enjoy the back deck with beautiful views of the mountains.

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 73, Hancock, MA 01237
  • 9 October Hill Dr, Lenox, MA 01240
    9 October Hill Dr, Lenox, MA 01240
    9 October Hill Dr, Lenox, MA 01240
    /60

    $1,490,000

    • 4 Beds
    • 4.5 Baths
    • 3,991 Sq Ft

    9 October Hill Dr, Lenox, MA 01240

    Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a

    Paula McLean PAULA MCLEAN REALTORS INC.

    9 October Hill Dr, Lenox, MA 01240
  • 33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    /69

    $730,000

    • 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
  • 37 Corey Rd Unit 532, Hancock, MA 01237
    37 Corey Rd Unit 532, Hancock, MA 01237
    /2

    $149,900

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 532, Hancock, MA 01237

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 532, Hancock, MA 01237
  • 4 Morgan Manor Unit 4, Lenox, MA 01240
    4 Morgan Manor Unit 4, Lenox, MA 01240
    4 Morgan Manor Unit 4, Lenox, MA 01240
    /15

    $368,000

    • 2 Beds
    • 1 Bath
    • 968 Sq Ft

    4 Morgan Manor Unit 4, Lenox, MA 01240

    Lenox in-town condo.....ready for a new owner, need a close location to Tanglewood, Shakespeare and Company, The Mount, Venfort Hall, Kennedy Park, Pleasant Valley Wildlife Sanctuary? Well this is the perfect location!2 bedrooms, 1 full bath, wood floors and carpeted bedrooms, great light ....fully applianced kitchen....Easy to show!

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    4 Morgan Manor Unit 4, Lenox, MA 01240
  • 103 Alpine Trail, Pittsfield, MA 01201
    103 Alpine Trail, Pittsfield, MA 01201
    103 Alpine Trail, Pittsfield, MA 01201
    /39

    $759,000

    • 3 Beds
    • 2.5 Baths
    • 2,381 Sq Ft

    103 Alpine Trail, Pittsfield, MA 01201

    Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a gracious entry with custom flooring and cedar hall closet that flows beautifully into the great room with vaulted ceilings, gas fireplace and glass doors to the screened porch and deck with a scenic view of the woods. The lovely updated kitchen is open to the dining area and great room for comfortable open

    Cortney Dupont COHEN & WHITE ASSOCIATES

    103 Alpine Trail, Pittsfield, MA 01201
  • 37 Corey Rd Unit 716, Hancock, MA 01237
    37 Corey Rd Unit 716, Hancock, MA 01237
    /2

    $145,000

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 716, 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 716, Hancock, MA 01237
  • 200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
    200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
    200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
    /30

    $895,000

    • 3 Beds
    • 2.5 Baths
    • 2,218 Sq Ft

    200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262

    Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
  • 1055 Beaver Pond Meadows, Hancock, MA 01237
    1055 Beaver Pond Meadows, Hancock, MA 01237
    1055 Beaver Pond Meadows, Hancock, MA 01237
    /27

    $264,900

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

    1055 Beaver Pond Meadows, Hancock, MA 01237

    Enjoy stunning views and low property taxes at Beaver Pond Meadows, private and quiet but close to all that Berkshire County's four seasons have to offer. This 3 bedroom 2 full bathroom townhouse features three levels of living area, with first-floor accessibility and multiple options for families. Three bedrooms and two full baths, living room with a wood floors & wood burning fireplace, and

    Kevin Moderski JIMINY REALTY

    1055 Beaver Pond Meadows, Hancock, MA 01237
  • 19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    /47

    $585,000

    • 2 Beds
    • 2.5 Baths
    • 1,935 Sq Ft

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262

    MOTIVATED SELLER! Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry

    Cortney Dupont COHEN & WHITE ASSOCIATES

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
  • 1052 Beaver Pond Meadows, Hancock, MA 01237
    1052 Beaver Pond Meadows, Hancock, MA 01237
    1052 Beaver Pond Meadows, Hancock, MA 01237
    /37

    $249,000

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

    1052 Beaver Pond Meadows, Hancock, MA 01237

    Mountain Condo Retreat - 3 Bed | 2 Bath | Ski Area LocationWelcome to this spacious 3-bedroom, 2-bath condo ideally located in a sought-after ski area, perfect for year-round enjoyment or a weekend getaway. This well-laid-out unit offers comfortable living with plenty of room for family and guests after a day on the slopes.Residents enjoy fantastic community amenities including an outdoor pool,

    Lisa Mendel BURNHAM GOLD REAL ESTATE, LLC

    1052 Beaver Pond Meadows, Hancock, MA 01237
  • 9102 Mountainside Dr, Hancock, MA 01237
    9102 Mountainside Dr, Hancock, MA 01237
    9102 Mountainside Dr, Hancock, MA 01237
    /32

    $659,999

    • 3 Beds
    • 3 Baths
    • 1,968 Sq Ft

    9102 Mountainside Dr, Hancock, MA 01237

    Step into this beautifully updated 3-bedroom, 3-bathroom retreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and

    Kevin Moderski JIMINY REALTY

    9102 Mountainside Dr, 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

    $147,000

    • 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
  • 19 N Church St Unit 5, North Adams, MA 01247
    19 N Church St Unit 5, North Adams, MA 01247
    19 N Church St Unit 5, North Adams, MA 01247
    /14

    $115,000

    • 1 Bed
    • 1 Bath
    • 323 Sq Ft

    19 N Church St Unit 5, North Adams, MA 01247

    This stunning North Adams condo is set in the iconic Historic Flat Iron Building at the corner of Church and Eagle Street. Thoughtfully renovated, the unit features granite countertops along with sleek stainless steel appliances. Previously operated as a successful Airbnb and now enjoyed as a primary residence, this condo offers flexibility and style. Enjoy easy access to downtown North Adams,

    Dante Cellana BURNHAM GOLD REAL ESTATE, LLC

    19 N Church St Unit 5, North Adams, MA 01247
  • 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

    $600,000

    • 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
  • 803 Crane, Hancock, MA 01237
    803 Crane, Hancock, MA 01237
    803 Crane, Hancock, MA 01237
    /24

    $459,900

    • 2 Beds
    • 2 Baths
    • 822 Sq Ft

    803 Crane, Hancock, MA 01237

    This condo is beautifully renovated with high end finishes. Styled right out of a design magazine, this 2 bedroom and 2 bath condo comes fully furnished. Excellent rental history. Located at the base of the mountain right next to the express lift, this is the perfect place for your winter ski retreat. Parking spot included and ski locker. The property has access to an indoor hot tub and fitness

    Kevin Moderski JIMINY REALTY

    803 Crane, Hancock, MA 01237
  • 19 N Church St Unit 12, North Adams, MA 01247
    19 N Church St Unit 12, North Adams, MA 01247
    19 N Church St Unit 12, North Adams, MA 01247
    /16

    $130,000

    • 1 Bed
    • 1 Bath
    • 330 Sq Ft

    19 N Church St Unit 12, North Adams, MA 01247

    Come see a part of the distinguished flat iron building in the historic Eagle St area of North Adams! Comes fully furnished, and a fully functioning Airbnb. Separate bedroom and sitting area. Tastefully decorated! Perfect to add to your portfolio or live in! 330 sqft, perfect for a nice getaway to experience Mass MoCA, shopping, restaurants, and all downtown North Adams has to offer!

    Susan Colvin MONARCH REALTY, INC.

    19 N Church St Unit 12, North Adams, MA 01247
  • 33 Maplewood Ave Unit 103, Pittsfield, MA 01201
    33 Maplewood Ave Unit 103, Pittsfield, MA 01201
    33 Maplewood Ave Unit 103, Pittsfield, MA 01201
    /40

    $214,900

    • 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
  • 16 Windflower Way, Williamstown, MA 01267
    16 Windflower Way, Williamstown, MA 01267
    16 Windflower Way, Williamstown, MA 01267
    /32

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,931 Sq Ft

    16 Windflower Way, Williamstown, MA 01267

    Welcome to this charming, freshly painted throughout and carpeted, 3-bedroom, 2 -bathroom condominium located in the desirable Greylock Village. This end unit offers comfort, convenience, and access to a peaceful and picturesque setting in the heart of the Berkshires. Whether you're looking for a full-time residence or a vacation getaway, this property is perfect for all lifestyles. The large

    Kim Burnham BURNHAM GOLD REAL ESTATE, LLC

    16 Windflower Way, Williamstown, MA 01267
  • 37 Corey Rd Unit 872, Hancock, MA 01237
    37 Corey Rd Unit 872, Hancock, MA 01237
    37 Corey Rd Unit 872, Hancock, MA 01237
    /16

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,133 Sq Ft

    37 Corey Rd Unit 872, Hancock, MA 01237

    Experience the pinnacle of slope-side living in this 3-bedroom, 2-full bathroom ski-on/ski-off condo. Boasting 1,133 sq. ft. of meticulously designed living space, this mountain retreat offers unparalleled convenience and comfort. Step directly from the lodge onto the trails, maximizing your time on the slopes and eliminating transportation hassles.Inside, you'll find an inviting atmosphere with

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 872, Hancock, MA 01237
  • 60 Churchill Crest, Pittsfield, MA 01201
    60 Churchill Crest, Pittsfield, MA 01201
    60 Churchill Crest, Pittsfield, MA 01201
    /34

    $279,900

    • 2 Beds
    • 1 Bath
    • 1,060 Sq Ft

    60 Churchill Crest, Pittsfield, MA 01201

    Welcome to Modern One Level Easy Living at Churchill Crest Condominiums. This unique offering has been meticulously updated and finished with new and improved features in each room. Enter spacious living room with expansive newer slider framing front to back views. Bousquet mountain out front and to rear see the rear patio, privacy, woods and beautiful custom landscape that has evolved from over

    Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

    60 Churchill Crest, Pittsfield, MA 01201
  • 81 Dartmouth St Unit 108, Pittsfield, MA 01201
    81 Dartmouth St Unit 108, Pittsfield, MA 01201
    81 Dartmouth St Unit 108, Pittsfield, MA 01201
    /52

    $159,900

    • 1 Bed
    • 1 Bath
    • 544 Sq Ft

    81 Dartmouth St Unit 108, Pittsfield, MA 01201

    Welcome to this beautifully maintained 1-bedroom, 1-bath condo located in the sought-after Crane Park Condos. This thoughtfully designed unit features an open-concept layout with granite countertops, stainless steel appliances, a gas range, travertine tile flooring, and charming shiplap ceilings. The spacious bedroom offers bamboo flooring, generous closet space, and overlooks the living area for

    Sai Kamasani LAMACCHIA REALTY, INC

    81 Dartmouth St Unit 108, Pittsfield, MA 01201
  • 580 S Main St Unit Building 1, Unit 6, Lanesborough, MA 01237
    580 S Main St Unit Building 1, Unit 6, Lanesborough, MA 01237
    580 S Main St Unit Building 1, Unit 6, Lanesborough, MA 01237
    /35

    $249,500

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft

    580 S Main St Unit Building 1, Unit 6, Lanesborough, MA 01237

    Unmatched stunning lake and mountain views! This renovated second-level one-bedroom, one-bath unit boasts easy living with open common spaces and private condo association dock spaces on Pontoosuc Lake. Great central location to enjoy cultural attractions here in the Berkshires! The owner has already taken care of the $20,000 special assessment and will be gifting a boat dock to the new owner.

    Brandon White COHEN & WHITE ASSOCIATES

    580 S Main St Unit Building 1, Unit 6, Lanesborough, MA 01237
  • 37 Corey Rd Unit 815, Hancock, MA 01237
    37 Corey Rd Unit 815, Hancock, MA 01237
    37 Corey Rd Unit 815, Hancock, MA 01237
    /32

    $425,000

    • 2 Beds
    • 1.5 Baths
    • 900 Sq Ft

    37 Corey Rd Unit 815, Hancock, MA 01237

    Top Floor unit with views of the slopes! This totally renovated 2-bedroom 1.5 bath unit with brand new everything. New floors. New appliances. New furniture. New Paint. New exposed beams. Private parking spot right out front. Private ski locker for your skis and boots. This unit also comes with a private owners closet that holds all the extras like bikes and rackets. Let's not forget this unit

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 815, Hancock, MA 01237
  • 189 Stratton Rd Unit H1, Williamstown, MA 01267
    189 Stratton Rd Unit H1, Williamstown, MA 01267
    189 Stratton Rd Unit H1, Williamstown, MA 01267
    /13

    $235,000

    • 2 Beds
    • 1 Bath
    • 713 Sq Ft

    189 Stratton Rd Unit H1, Williamstown, MA 01267

    Welcome home to this beautifully updated 2-bedroom, 1-bathroom ground floor condo offering comfort, convenience, and breathtaking distant mountain views. Bright and inviting, this residence features an open-concept living area, modern finishes, and large windows that fill the space with natural light while showcasing the serene landscape beyond.

    Alyssa Sherman MORESI REAL ESTATE PARTNERS

    189 Stratton Rd Unit H1, Williamstown, MA 01267
  • 1 Pondview Dr Unit C3, Pittsfield, MA 01201
    1 Pondview Dr Unit C3, Pittsfield, MA 01201
    1 Pondview Dr Unit C3, Pittsfield, MA 01201
    /20

    $229,900

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft

    1 Pondview Dr Unit C3, Pittsfield, MA 01201

    Two bedroom condo in James Meadows featuring fireplace, loft bedroom, storage room, and deck all conveniently located close to Allendale area.

    Robin Moore 413 REAL ESTATE

    1 Pondview Dr Unit C3, Pittsfield, MA 01201
  • 1 Rolling Hills Unit 10, Lenox, MA 01240
    1 Rolling Hills Unit 10, Lenox, MA 01240
    1 Rolling Hills Unit 10, Lenox, MA 01240
    /21

    $389,900

    • 2 Beds
    • 2 Baths
    • 1,576 Sq Ft

    1 Rolling Hills Unit 10, Lenox, MA 01240

    Unique opportunity to own a beautifully updated condo. This inviting home offers 2 bedrooms and 2 full bathrooms, a gorgeous updated kitchen, and a finished room in the basement perfect for a home office, gym, or additional living space. Enjoy outdoor living with two porches, and note that the unit may be offered furnished for added convenience. All this nestled in the heart of the picturesque

    Michele Purcell LAMACCHIA REALTY, INC

    1 Rolling Hills Unit 10, Lenox, MA 01240
  • 71 S Church St Unit S102, Pittsfield, MA 01201
    71 S Church St Unit S102, Pittsfield, MA 01201
    71 S Church St Unit S102, Pittsfield, MA 01201
    /9

    $250,800

    • 1 Bed
    • 1 Bath
    • 1,200 Sq Ft

    71 S Church St Unit S102, Pittsfield, MA 01201

    Live in a stylish renovation of an important historical building. Spacious rooms with high ceilings, exposed beams but up to date amenities. High quality fixtures and fittings. Walk in closet. In unit washer, dryer and storage. Sunny southern exposure. Building has natural gas heating, high tech a/c. Roof deck with great views of Pittsfield and a well appointed gym. Must be seen.

    Martha Piper THE KINDERHOOK GROUP

    71 S Church St Unit S102, Pittsfield, MA 01201
  • 46 Housatonic St Unit 2B, Lenox, MA 01240
    46 Housatonic St Unit 2B, Lenox, MA 01240
    46 Housatonic St Unit 2B, Lenox, MA 01240
    /28

    $650,000

    • 2 Beds
    • 2 Baths
    • 1,098 Sq Ft

    46 Housatonic St Unit 2B, Lenox, MA 01240

    Beautiful two bedroom, two bath condo perfectly situated in the center of Lenox, Massachusetts-the cultural heart of the Berkshires. Enjoy high Ceilings, beautiful wood floors, large windows, and abundant natural light throughout. The spacious layout features a gas fireplace, granite countertops, and a gas stove in the modern kitchen. The inviting living room opens to a private balcony, perfect

    Patricia Andrew STONE HOUSE PROPERTIES, LLC

    46 Housatonic St Unit 2B, Lenox, MA 01240
  • 37 Corey Rd Unit 623, Hancock, MA 01237
    37 Corey Rd Unit 623, Hancock, MA 01237
    37 Corey Rd Unit 623, Hancock, MA 01237
    /14

    $143,000

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 623, 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 623, Hancock, MA 01237
  • 37 Corey Rd Unit 14, Hancock, MA 01237
    37 Corey Rd Unit 14, Hancock, MA 01237
    37 Corey Rd Unit 14, Hancock, MA 01237
    /30

    $319,900

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    37 Corey Rd Unit 14, Hancock, MA 01237

    Enjoy the ultimate convenience of living at a ski resort, with easy access to slopes, hiking trails, mountain biking, dining, and other resort amenities right at your doorstep. Wood burning fireplace will keep you warm on those cold winter nights. Embrace the year-round mountain lifestyle in this exceptional 3-bedroom, 2-full-bath home, ideally situated for both adventure and relaxation. Nestled

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 14, Hancock, MA 01237
  • 37 Corey Rd Unit 9061, Hancock, MA 01237
    37 Corey Rd Unit 9061, Hancock, MA 01237
    37 Corey Rd Unit 9061, Hancock, MA 01237
    /30

    $530,000

    • 2 Beds
    • 3 Baths
    • 1,843 Sq Ft

    37 Corey Rd Unit 9061, Hancock, MA 01237

    New to the market a large end unit in Mountainside Hemlock Village a 2+ bedrooms (sleeping loft) 3 full bathrooms on 3 levels of living. This end unit has lots of windows and space for the larger family. Park your car right out front and walk into your ski vacation condo. Great rental history if you decide you want to rent. The condo is sold fully furnished and is turnkey. Great location on lower

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 9061, Hancock, MA 01237
Massachusetts Berkshire County Windsor

Condos for Sale in Windsor, MA

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.

Learn more about living in Windsor

Home Trends in Windsor, MA

On average, homes in Windsor, MA sell after 68 days on the market compared to the national average of 54 days. The median sale price for homes in Windsor, MA over the last 12 months is $397,500, down 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$397,500
Median Single Family Sale Price
$397,500
Average Price Per Sq Ft
$221
Number of Homes for Sale
0
Last 12 months Home Sales
16
Months of Supply
0.00
Median List Price
$437,500
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-18%
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