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Explore Similar Condos Within 10 Miles of Canaan, NY

  • /46

    $1,280,000 Open Sat 11AM - 2PM

    • 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
  • /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
  • /44

    $429,900

    • 3 Beds
    • 2.5 Baths
    • 1,806 Sq Ft

    33 Walden Ln, Pittsfield, MA 01201

    Situated on an elevated lot in desirable Walden Village, this meticulously maintained home offers a private backyard perfect for outdoor entertaining. The main level features a convenient primary suite with a full ensuite bath, a guest powder room, and the convenience of first-floor laundry. An elegant, open floor plan provides excellent flow for both entertaining and everyday living, and a bonus

    Tiffany Roberts ROBERTS & ASSOC. REALTY, INC

    33 Walden Ln, Pittsfield, MA 01201
  • /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
  • /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
  • /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
  • /65

    $895,000

    • 5 Beds
    • 3 Baths
    • 4,802 Sq Ft

    581 Red Barn Rd, Dalton, MA 01226

    Immaculate 4800 square foot, 5BR, 4 full bath jewel located at arguably the finest condominium community in The Berkshires. Enjoy looking at spectacular foliage with private panoramic wooded views and open space from the magnificent all seasons room, great room and primary suite. The garden level features a full kitchen as well as a screened in porch. The Buterus furnace system powers baseboard

    Buddy Lewis BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    581 Red Barn Rd, Dalton, MA 01226
  • /25

    $255,000

    • 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
  • /14

    $160,000

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 521, 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 521, Hancock, MA 01237
  • /46

    $649,000

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

    14 Sunrise Cir, Pittsfield, MA 01201

    Immaculate and beautifully updated free-standing home offering effortless one-level living. The open-concept floor plan seamlessly connects the living, dining, kitchen, and den areas, all enhanced by abundant windows that fill the space with natural light. The chef's kitchen features quartz countertops, stainless steel appliances, and a generous center island ideal for entertaining. Three

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    14 Sunrise Cir, 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
  • /24

    $439,000

    • 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
  • /36

    $278,800

    • 1 Bed
    • 1 Bath
    • 658 Sq Ft

    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

    Looking for one-level living in the heart of the Berkshires? Comfort, convenience and move-in-ready appeal is what you'll find at this Heron Pond condo! Well-maintained, 1 br/1ba unit filled with natural light includes living room, separate dining room, updated bath and galley kitchen. Outside, relax on your own stone patio. Enjoy peaceful surroundings, the pond, and beautifully kept grounds.

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
  • /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
  • /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
  • /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

    $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.Recent price reduction--motivated owner says sell! Don't miss this opportunity to own in a sought-after

    Lisa Mendel BURNHAM GOLD REAL ESTATE, LLC

    1052 Beaver Pond Meadows, 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
  • /19

    $315,000

    • 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
  • /15

    $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
  • /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
  • /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
  • /60

    $1,490,000 Open Sat 11:30AM - 1PM

    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /30

    $509,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /31

    $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

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
$732,500
Average Price Per Sq Ft
$388
Number of Homes for Sale
11
Last 12 months Home Sales
41
Months of Supply
3.20
Median List Price
$732,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
14%
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