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Explore Similar Condos Within 10 Miles of Canaan, NY

  • /15

    $450,000

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    37 Corey Rd Unit 812, Hancock, MA 01237

    Discover the perfect mountain retreat in this beautifully maintained 2-bedroom, 2 full bath condo offering 1,030 square feet of comfortable living space. Ideally located just moments from the ski slopes, this home is a dream for outdoor enthusiasts and year-round adventurers.Enjoy easy access to a wide range of community amenities, including a heated pool, tennis courts, and beautifully

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 812, Hancock, MA 01237
  • /14

    $358,000

    • 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
  • /69

    $699,000

    • 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
  • /23

    $315,000

    • 2 Beds
    • 1.5 Baths
    • 1,320 Sq Ft

    1 Colt Rd Unit 7, Pittsfield, MA 01201

    Sophisticated living in Pittsfield's most walkable neighborhood! This move-in ready 2BR/1.5BA bright condominium spans 1,320 SF across two thoughtfully designed levels. Freshly painted interiors & brand new carpeting create a like-new feel. Main level showcases a large great room with wood-burning fireplace, formal dining area, cozy kitchen, convenient laundry & half bath. Upstairs offers a

    Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1 Colt Rd Unit 7, Pittsfield, MA 01201
  • /31

    $639,999

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

    9102 Mountainside Dr, Hancock, MA 01237

    Step into this beautifully updated 3-bedroom, 3-bathroom with a lretreat 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
  • /41

    $410,000

    • 2 Beds
    • 1 Bath
    • 1,176 Sq Ft

    37 Corey Rd Unit 845, Hancock, MA 01237

    Perfectly positioned in the heart of Jiminy Peak Mountain Resort, this stylishly updated two-bedroom, one-bath condominium offers the ultimate slopeside lifestyle. Just steps from the lifts, you'll enjoy effortless access to one of the region's premier ski destinations while retreating to a thoughtfully designed interior that blends comfort and modern appeal. The bright, open living space is

    Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    37 Corey Rd Unit 845, 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
  • /29

    $600,000

    • 3 Beds
    • 2 Baths
    • 2,030 Sq Ft

    32 Aspen Way, Pittsfield, MA 01201

    Set on Aspen Way in Pittsfield, this well-maintained condo offers a practical layout and easy, low-maintenance living in a desirable community.The main level welcomes you with an open living area featuring a gas fireplace, flowing into a spacious dining area. The kitchen is positioned at the back of the home and is finished with stainless steel appliances and granite countertops, with a slider

    Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

    32 Aspen Way, Pittsfield, MA 01201
  • /50

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,647 Sq Ft

    2 Wallace Rd Unit 2E, Stockbridge, MA 01262

    Welcome to Heron Pond Condominiums in charming Stockbridge, where comfort meets convenience in a tranquil setting. This beautiful condominium offers an ideal combination of spacious living and cozy charm, featuring 2 or 3 bedrooms and 2 full baths. The screened porch is ideal to relax and enjoy nature without the bugs, a serene space to unwind, whether you're enjoying morning coffee or evening

    Paula McLean PAULA MCLEAN REALTORS INC.

    2 Wallace Rd Unit 2E, Stockbridge, MA 01262
  • /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
  • /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
  • /25

    $255,000 Open Sat 11:30AM - 1PM

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

    58 Churchill Crest, Pittsfield, MA 01201

    2 bedroom end unit condo offering the rare ease of true one level living, tucked in Churchill Crest's most private and peaceful building. This special home feels like a quiet Berkshire sanctuary, with a thoughtful layout that flows comfortably and welcomes you the moment you arrive. It's ready for your vision, character allows you to shape the space to your own style. Outside, enjoy a sparkling

    Keyla Girard LAMACCHIA REALTY, INC

    58 Churchill Crest, Pittsfield, MA 01201
  • /16

    $159,000 Open Sat 10AM - 11:30AM

    • 1 Bed
    • 1 Bath
    • 617 Sq Ft

    108 E Housatonic St Unit 7, Pittsfield, MA 01201

    Great location in Southeast Pittsfield..Short walk to downtown Pittsfield.. Lovely unit with hardwood floors in the Living room and Bedroom......Nice sized balcony (facing the morning sun) to relax on..Coin operated laundry just a few steps down into the lower level.. Storage locker is available in an upstairs area through the door on the balcony. The unit sq footage is 617 and is recorded in the

    Barbara K Greenfeld SIGNATURE ASSOCIATES

    108 E Housatonic St Unit 7, Pittsfield, MA 01201
  • /60

    $1,350,000

    • 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
  • /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
  • /80

    $1,400,000

    • 4 Beds
    • 4 Baths
    • 3,379 Sq Ft

    2 Saint Andrews Ct, Lenox, MA 01240

    Welcome to elegant single-level living in one of Lenox's most coveted locations. Ideally positioned on prestigious Saint Andrews Drive, this exceptional home offers privacy, comfort, and stunning views--just minutes from the heart of the Berkshires.This expansive 3,379-square-foot residence features four bedrooms and four full baths, thoughtfully designed for both everyday living and

    Jose Larios LAMACCHIA REALTY, INC

    2 Saint Andrews Ct, Lenox, MA 01240
  • /19

    $819,000

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

    5 Aspen Way, Pittsfield, MA 01201

    Great opportunity to design your 2000 sq ft free-standing condo home at Berkshire Country Meadows! This is one of only three remaining homesites in this established condo community. Select from a several floor plans with contemporary design, featuring one-level living. Primary suite, one-two additional bedrooms, central a/c, gas heat, screened porch, two car garage. On-site amenities include

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    5 Aspen Way, Pittsfield, MA 01201
  • /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
  • /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
  • /34

    $245,000

    • 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
  • /37

    $244,000

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

    1052 Beaver Pond Meadows, Hancock, MA 01237

    Enjoy maintenance-free living in this beautifully situated 3 bedroomc, two bathroom condo just minutes from Jiminy Peak ski resort. This inviting property offers access to a saltwater pool, newly built tennis courts, and scenic surroundings perfect for year-round relaxation or adventure. It also has VERY low taxes, another great bonus!Recent price reduction--motivated owner says sell! Don't miss

    Lisa Mendel BURNHAM GOLD REAL ESTATE, LLC

    1052 Beaver Pond Meadows, Hancock, MA 01237
  • /33

    $799,000 New Construction

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

    15 Cherry Hill Dr, Pittsfield, MA 01201

    Berkshire Country Meadows single-family condo almost ready for occupancy. Seeking single level living? Compare this for value! 2000 sq ft, 3 br, 2 bath, central a/c, natural gas heat, gas fireplace hardwood flooring, screened porch, large basement offers expansion possibilities, and a two-car garage. Still time to make some custom finishes. Established condo community with pool, tennis, and

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    15 Cherry Hill Dr, Pittsfield, MA 01201
  • /30

    $299,900

    • 1 Bed
    • 1 Bath
    • 672 Sq Ft

    825 Thatcher House, Hancock, MA 01237

    IT DOESN'T GET ANY EASIER THAN THIS!! Own this beautiful slope facing 1 bedroom loft condo situated above the ski rental shop. Only 2 units like this exist in the Village Center! Brand new slope side deck overlooking the Berkshire Express chairlift. Newly renovated kitchen and bathroom, and freshly painted. Owner replaced heating/cooling unit and washer/dryer. Fully furnished, including new

    Kevin Moderski JIMINY REALTY

    825 Thatcher House, Hancock, MA 01237
  • /31

    $299,000

    • 2 Beds
    • 2 Baths
    • 1,624 Sq Ft

    3 Rolling Hills Unit 2, Lenox, MA 01240

    Beautifully maintained 2 bedroom, 2 bath condo, both bedrooms/ baths on main level with covered deck & beautiful views, finished lower level w/ laundry offers whole other level of space for office, hobbies, etc. Enjoy the clubhouse (gym, pool table, hot tub, sauna, kitchen/entertainment rm, local art hangings) out door POOL, TENNIS COURTS, walking TRAILS, community GARDENS, kayak storage, fenced

    Donna DiGrigoli DIGRIGOLI REAL ESTATE

    3 Rolling Hills Unit 2, Lenox, MA 01240
  • /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
  • /62

    $1,279,000

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

    18 Highcrest Rd, Lenox, MA 01240

    Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly

    Suzann Ward HOUSATONIC REAL ESTATE

    18 Highcrest Rd, Lenox, MA 01240
  • /20

    $189,900

    • 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
  • /19

    $299,000

    • 3 Beds
    • 2.5 Baths
    • 1,863 Sq Ft

    51 Churchill Crest Unit 51, Pittsfield, MA 01201

    This charming 3 bedroom and 2.5 bathroom condo is a must see! Offering fantastic location with scenic views of the swimming pool from your private deck. The bright and sunny kitchen seamlessly connect to the dining room making it perfect for entertaining. A Spacious living room features a wood burning fireplace. Additional features include one-car garage, storage closest and in-unit laundry for

    Molly Thomas COMPASS MASSACHUSETTS , LLC GB

    51 Churchill Crest Unit 51, Pittsfield, MA 01201
  • /13

    $140,000

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 721, 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 721, 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
  • /28

    $229,000

    • 2 Beds
    • 1 Bath
    • 902 Sq Ft

    1 Colt Rd Unit 1, Pittsfield, MA 01201

    Welcome to easy, in-town living at sought-after One Colt Road in a charming neighborhood. This first-floor condominium offers the perfect blend of convenience and comfort, just a short stroll to Berkshire Museum, Colonial Theatre, local restaurants, and boutique shops. Featuring 2 bedrooms and 1 bath, the layout is both functional and inviting. A rare screened porch extends your living space,

    Victoria Standring LAMACCHIA REALTY, INC

    1 Colt Rd Unit 1, Pittsfield, MA 01201
  • /19

    $307,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    9 Forest Row, Great Barrington, MA 01230

    Why rent when you can own in a delightful neighborhood. Immaculate ground level unit in the private country community of Forest Row., located just a few minutes from downtown Great Barrington. Forest Row is a Community Land Trust Neighborhood. Easy care one level living with an open floor plan, private screened porch and a patio bordered by gardens and woods, surrounded by 21 acres of protected

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    9 Forest Row, Great Barrington, MA 01230
  • /29

    $509,000

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

    37 Corey Rd Unit 9061, Hancock, MA 01237

    A spacious end-unit condo in Mountainside Hemlock Village, offering 2+ bedrooms (including a sleeping loft) and 3 full bathrooms across three levels of living space. This bright, airy unit features abundant windows and ample room, making it ideal for larger families. Enjoy the convenience of parking right outside your door and stepping directly into your ski getaway. The property has a strong

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 9061, Hancock, MA 01237

Why Live in Canaan

Canaan is a quiet, rural town just outside the Berkshires, known for its friendly atmosphere, wooded landscapes and wide-open farmland. It appeals to homebuyers who want privacy and space while still being within a short drive of Chatham and Pittsfield for shopping, dining and everyday services. The housing mix includes rustic cabins, classic farmhouses and larger vacation homes, making it attractive to buyers coming from Western Massachusetts or the Boston area who want more room to spread out. While home prices tend to be lower than in nearby Massachusetts, buyers should expect higher property taxes typical of New York. Outdoor recreation shapes daily life, with summer activity centered around Queechy Lake and easy access to hiking and fall foliage throughout the surrounding state forests. Winters bring more snow than in the lower-lying parts of the county, with nearby ski resorts to stay active. Canaan has no large town center, so errands often require a short drive, and services like internet and cell coverage vary by location. Overall, Canaan is best suited for buyers seeking peaceful, nature-focused living with Berkshire access, and for those who are comfortable with the realities of rural life.

Home Trends in Canaan, NY

Housing Trends

Median Sale Price
$750,000
Median Single Family Sale Price
$750,000
Average Price Per Sq Ft
$384
Number of Homes for Sale
11
Last 12 months Home Sales
35
Months of Supply
3.80
Median List Price
$732,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
14%
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