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Explore Similar Homes Within 10 Miles of Spencertown, NY

  • /50

    $845,000

    • 4 Beds
    • 3.5 Baths
    • 2,955 Sq Ft

    9 Castle Hill Rd, Stockbridge, MA 01262

    Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated,

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 269-8632

    9 Castle Hill Rd, Stockbridge, MA 01262
  • /43

    $2,650,000

    • 5 Beds
    • 5.5 Baths
    • 4,000 Sq Ft

    5988 New York 9h, Hudson, NY 12534

    Set way back from the road is this spacious, 5-Bedroom, 4.5 Bath Contemporary Farmhouse which embodies timeless craftsmanship and country charm. This carefully curated home is a blend of natural stone, hand hewn repurposed Hemlock timber beams, honey colored wide board Pine flooring, fine finishes and efficient systems throughout. inside the front door lies a Great Room with a 25' high cathedral

    Agent Photo

    Paul Barrett

    Houlihan Lawrence, Inc

    (518) 634-9174

    5988 New York 9h, Hudson, NY 12534
  • /71

    $5,650,000

    • 11 Beds
    • 10 Baths
    • 9,748 Sq Ft

    25 W Sheffield Rd, Great Barrington, MA 01230

    Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

    Lauren Molk ELYSE HARNEY REAL ESTATE

    25 W Sheffield Rd, Great Barrington, MA 01230
  • /86

    $2,000,000

    • 5 Beds
    • 4.5 Baths
    • 4,842 Sq Ft

    173 Hillsdale Rd, Egremont, MA 01230

    Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one of the most private and extraordinary estates in the Berkshires -- a handcrafted sanctuary where the wilderness is literally your backyard. Moose, deer, bear, fox, and turtles roam master-gardened grounds tended with rare care; fruit trees, a garden pond, mature perennial beds, and lush native plantings make

    Robert Cohen eXp REALTY

    173 Hillsdale Rd, Egremont, MA 01230
  • /41

    $4,850,000

    • 13 Beds
    • 13.5 Baths
    • 9,510 Sq Ft

    2 Kemble St, Lenox, MA 01240

    The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental.The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a

    Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

    2 Kemble St, Lenox, MA 01240
  • /46

    $7,250,000

    • 6 Beds
    • 7 Baths
    • 13,175 Sq Ft

    209 Blue Hill Rd, Great Barrington, MA 01230

    A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook--creating a secluded retreat that feels worlds

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    209 Blue Hill Rd, Great Barrington, MA 01230
  • /55

    $579,000

    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    86 E Main St, Stockbridge, MA 01262

    Prime location just a short distance to Stockbridge Village, Tangelwood, Berkshire Theatre Group and many more cultural attractions here in the beautiful Berkshires. Sprawling backyard with Housatonic River views. Open common spaces with ample space, exposed beams, character and wood flooring. The second level offers two bedrooms, full bath, large landing flex space and office/sitting area.

    Cortney Dupont COHEN & WHITE ASSOCIATES

    86 E Main St, Stockbridge, MA 01262
  • /60

    $2,185,000

    • 3 Beds
    • 3.5 Baths
    • 4,752 Sq Ft

    14 Old Tree Farm Rd, Stockbridge, MA 01262

    A rare Berkshire offering w/ space, privacy, & exceptional versatility. Fabulous home & separate studio minutes from Tanglewood & Stockbridge Bowl. Charming 3 BR, 2.5 BA, 2,952 sq ft home - complemented by a beautifully renovated 1,800 sq ft studio barn w/ loft & full BA - rests on 8 picturesque acres with beautiful western views. Perfect for outdoor enthusiasts, culture lovers, or anyone seeking

    Claire Pollart WILLIAM RAVEIS - BERKSHIRE

    14 Old Tree Farm Rd, Stockbridge, MA 01262
  • /28

    $329,000

    • 4 Beds
    • 3 Baths
    • 2,276 Sq Ft

    44 Main St, West Stockbridge, MA 01266

    Discover the charm of downtown living in this Colonial home located in the heart of West Stockbridge. This home features four bedrooms, two full baths, kitchen, living room, dining room and a deck overlooking the river. In addition to the main living area the property also includes an in-law or studio apartment with it's own kitchen and bathroom. With a nice flat yard for outdoor activities,

    Molly Thomas COMPASS MASSACHUSETTS , LLC GB

    44 Main St, West Stockbridge, MA 01266
  • /53

    $3,750,000

    • 4 Beds
    • 3.5 Baths
    • 3,225 Sq Ft

    40 E Alford Rd, West Stockbridge, MA 01266

    Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    40 E Alford Rd, West Stockbridge, MA 01266
  • /55

    $3,500,000

    • 5 Beds
    • 6.5 Baths
    • 6,088 Sq Ft

    110 Alford Rd, Great Barrington, MA 01230

    Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside,

    Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    110 Alford Rd, Great Barrington, MA 01230
  • /65

    $12,500,000

    • 4 Beds
    • 6 Baths
    • 6,829 Sq Ft

    241 Cunningham Hill Rd, Canaan, NY 12029

    A Home like no other. You will simply not find a Property like PIERCE PEAK, anywhere. AIA Award Winning Architectural Design by Burr & McCallum, crested upon the summit of Cunningham Hill. Cleared for HELIPAD . Open plan living with Indoor and Outdoor Living Rooms. Gourmet Kitchen, 2 Primary and 2 connnected Loft spaces. 2 Bedroom Guest Quarters. Gym. Infinity Pool w/Bar, Fireplace and Outdoor

    Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    241 Cunningham Hill Rd, Canaan, NY 12029
  • /55

    $1,490,000

    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    5 Glendale Rd, Stockbridge, MA 01262

    ''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming

    Martha Piper THE KINDERHOOK GROUP

    5 Glendale Rd, Stockbridge, MA 01262
  • /47

    $1,465,000

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    9 Bott Hill Rd, Egremont, MA 01230

    Stunning Post and Beam Home with Log Facade. Nestled in a park-like setting with views of Mount Washington. Outdoor Amenities Galore. Extensive patios and wraparound decks provide the perfect venues for outdoor gatherings including a private bocce ball court, outdoor hot tub, and private dog park. The first floor offers generous entertaining spaces, including two to three bedrooms that provide

    Suzann Ward HOUSATONIC REAL ESTATE

    9 Bott Hill Rd, Egremont, MA 01230
  • /54

    $14,500,000

    • 4 Beds
    • 5.5 Baths
    • 5,888 Sq Ft

    199 Eichybush Rd, Kinderhook, NY 12106

    DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling

    Michael Stasi Corcoran Country Living

    199 Eichybush Rd, Kinderhook, NY 12106
  • /46

    $1,500,000

    • 7 Beds
    • 7.5 Baths
    • 6,232 Sq Ft

    802 State Rd, Richmond, MA 01254

    Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. Spanning 11 bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages and a great barn for entertaining. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    802 State Rd, Richmond, MA 01254
  • /66

    $6,850,000

    • 5 Beds
    • 3.5 Baths
    • 3,474 Sq Ft

    77 Seekonk Cross Rd, Great Barrington, MA 01230

    Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/

    Elvia Gignoux WILLIAM PITT SOTHEBY'S - SALISBURY

    77 Seekonk Cross Rd, Great Barrington, MA 01230
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