Homes for Sale near Hillcrest Educational Centers

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  /41

  $2,995,000

  $500K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,862 Sq Ft

  16 Old Tree Farm Rd, Stockbridge, MA 01262

  Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  16 Old Tree Farm Rd, Stockbridge, MA 01262
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  /46

  $4,975,000

  • 3 Beds
  • 3.5 Baths
  • 4,359 Sq Ft

  5 Deer Hill Rd, West Stockbridge, MA 01266

  Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  5 Deer Hill Rd, West Stockbridge, MA 01266
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  /24

  $449,000

  • 3 Beds
  • 2 Baths
  • 850 Sq Ft

  195 Dublin Rd, Richmond, MA 01254

  A wonderful opportunity in an outstanding part of the county! The town considers this a three-bedroom property, with a four-bedroom septic system already in place. Recent renovations include a beautiful new kitchen and two updated baths, while the walkout lower level offers additional flexibility and potential. With the major interior improvements already completed, this property is ideal as a

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  195 Dublin Rd, Richmond, MA 01254
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  /47

  $1,399,000

  $51K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,968 Sq Ft

  3 A Coldbrooke Dr, Lenox, MA 01240

  Four-bedroom homes are a rarity at Coldbrooke, where most residences offer three. This one combines that hard-to-find layout and one of the community's more generous floor plans with a location beside the Miraval Berkshires resort and the historic Wyndhurst estate, putting world-class spa, dining, and golf just steps from the door. Inside, vaulted ceilings and an open layout fill the home with

  Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

  3 A Coldbrooke Dr, Lenox, MA 01240
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  /45

  $399,900

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft

  15 Silver St, Lee, MA 01238

  Tucked away on just under an acre of absolute privacy in beautiful Lee MA., This modified Cape-style home is a masterclass in character. Ready for you to bring this home to its modern beauty! Step inside to find hardwood floors that guide you into a spectacular living room, where dramatic vaulted ceilings create an airy, sanctuary. Two cozy pellet stoves offer the ultimate in warmth and ambiance

  Jason Nocher NOCHER REALTY

  15 Silver St, Lee, MA 01238
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  /31

  $712,000

  $40K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,750 Sq Ft

  9 Interlaken Rd, Stockbridge, MA 01262

  Quitessential 1830's side hall Colonial....charming home located in the village of Interlaken in the town of Stockbridge, MA....just minutes to Lenox, Stockbridge center and the Berkshire Botanical Center. Listen to the babbeling water from the Larrywaug Brook and walk just steps to the small town park.....sit on the deck or around the firepit to soak in the atmosphere of privacy and

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  9 Interlaken Rd, Stockbridge, MA 01262
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  /76

  $1,950,000

  • 4 Beds
  • 4.5 Baths
  • 4,612 Sq Ft

  9 Fairwynds Dr, Lenox, MA 01240

  Move-in ready and beautifully upgraded, freestanding home offers the ease of one-level living paired with over 4,600 sf over three finished levels. Four br, 4.5 bat and a walkout lower level. Live at the desirable Miraval golf/resort campus.Hardwood floors flow throughout the main living area, anchored by a striking double-sided fireplace wi stone hearth connecting the living and family

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  9 Fairwynds Dr, Lenox, MA 01240
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  /23

  $350,000

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  140 Orchard St, Lee, MA 01238

  Welcome to 140 Orchard Street, an inviting three-bedroom, one-bathroom Lee home that effortlessly combines everyday convenience with a warm, relaxed atmosphere. Bathed in natural sunlight, the cozy interior features an easy-flowing floor plan anchored by a desirable first-floor bedroom and full bathroom, creating a comfortable and welcoming layout the moment you step through the front door and

  Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  140 Orchard St, Lee, MA 01238
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  /19

  $447,900

  • Land
  • 10.02 Acres
  • $44,701 per Acre

  0 Swamp Rd, Richmond, MA 01254

  Offered for the first time in generations, this exceptional 10-acre parcel presents a rare opportunity to create a home in one of the Berkshires' most picturesque settings. Nestled among open farmland and rolling countryside, the property offers a beautiful blend of gently rolling meadows, a private pond, mature trees, and seasonal wildflowers, creating a landscape that feels both peaceful and

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  0 Swamp Rd, Richmond, MA 01254
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  /11

  $95,000

  • Land
  • 1.42 Acres
  • $66,901 per Acre

  570-580 East St, Lee, MA 01238

  Located in a residential area with a bit of a rural feel. These two building lots with an approximate 1.42 acres and 324 foot frontage combined are being sold together. This rare opportunity offers privacy and flexibility with access to Town Water & Sewer, Electric and Natural Gas. Only minutes to downtown Lee, Lenox and the Mass Pike.

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  570-580 East St, Lee, MA 01238
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  /45

  $2,950,000

  $450K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 3,432 Sq Ft

  36 Yale Hill Rd, Stockbridge, MA 01262

  EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for

  Mandy Victor-pieczarka STONE HOUSE PROPERTIES, LLC

  36 Yale Hill Rd, Stockbridge, MA 01262
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  /37

  $685,000

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262

  STUNNING VIEWS for as far as you can see from this modern unit located in Winden Hills Vanna building. Open common spaces washed in natural light; Great room with scenic views, fireplace and built ins, kitchen with charm and character open to dining. Primary w/en suite full bath, two guest bedrooms and additional one and half baths. This unit comes with access to the elevator for convenience, a

  Cortney Dupont COHEN & WHITE ASSOCIATES

  200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262
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  /33

  $419,000

  $70K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,457 Sq Ft

  181 New Lenox Rd, Lenox, MA 01240

  Enchanting Lenox Cottage minutes to Tanglewood- 2 Bedroom / 2 Full Bath RetreatThe bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch & 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand-new back deck, an ideal setting for summer evenings. 2 Bedrooms on second floor, with

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  181 New Lenox Rd, Lenox, MA 01240
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  /19

  $169,000

  $10K PRICE DROP

  • Land
  • 1.8 Acres
  • $93,889 per Acre

  0 Church St, Lee, MA 01238

  Bucolic 1.80-acre level parcel with mountain views, just minutes from downtown Lee, Stockbridge, and Lenox. Tucked back for added privacy, convenient access to the property via a wide quiet, low-traffic street, while a dense, natural buffer of trees offers excellent separation from the adjacent street. A large portion of the land is an open meadow, offering a builder flexible home placement

  Lisa Kelley MACCARO REAL ESTATE

  0 Church St, Lee, MA 01238
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  /44

  $1,450,000

  • 5 Beds
  • 3.5 Baths
  • 3,392 Sq Ft

  577 Mallard Ln, Lee, MA 01238

  Experience upscale, maintenance-free living in desirable Devon Meadows, ideally located near Lenox and Stockbridge and just 5 minutes from Tanglewood and the many cultural and outdoor attractions of the Berkshires. This spacious luxury condominium features an open floor plan perfect for everyday living and entertaining. The first floor offers a primary bedroom suite, laundry, and a versatile

  Denise DeSellier BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  577 Mallard Ln, Lee, MA 01238
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  /43

  $629,000

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  13 Glendale Middle Rd, Stockbridge, MA 01262

  Come see this Stockbridge home with land, multiple fireplaces, all electric service, and close to everything the Berkshires has to offer! You'll be minutes to historic downtown Stockbridge, Tanglewood, and all the entertainment venues that you love, in a quiet country setting. All the comforts of home, available to you right now! Come be a part of the Berkshires lifestyle, you'll be glad you did!

  Richard Needelman BISHOP WEST REAL ESTATE

  13 Glendale Middle Rd, Stockbridge, MA 01262
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  /38

  $879,000

  $120K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,262 Sq Ft

  22 Post Rd, Lenox, MA 01240

  Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area

  India Ward NON-MEMBER / RECIPROCAL

  22 Post Rd, Lenox, MA 01240
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  /19

  $700,000

  $50K PRICE DROP

  • 8 Beds
  • 4 Baths
  • 3,192 Sq Ft

  35 Main St, West Stockbridge, MA 01266

  Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.Can also be purchased as part of a investment portfolio 13 Park Street Stockbridge, MA MLS#249532

  Matt Carlino MACCARO REAL ESTATE

  35 Main St, West Stockbridge, MA 01266
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  /46

  $799,000

  • 3 Beds
  • 3 Baths
  • 2,732 Sq Ft

  135 East St, Lee, MA 01238

  Thoughtfully crafted custom home offering timeless New England character, quality craftmanship, and beautiful eastern mountain views. Rich natural woodwork and exposed beams create a warm, inviting atmosphere throughout. The custom kitchen with granite, marble and butcher block countertops opens to the dining area with French doors leading to a screened in sunroom. Enjoy the expansive deck, stone

  Lisa Kelley MACCARO REAL ESTATE

  135 East St, Lee, MA 01238
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  /28

  $579,000

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  78 E Main St, Stockbridge, MA 01262

  Charming Historic Gem in the Heart of StockbridgeEmbrace classic New England living in this 3-bedroom, 2-bathroom home boasting 1,664 square feet of old-world charm, warmth, and character. Ideally located along East Main Street, this residence offers an unbeatable, walk-to-everything village lifestyle while maintaining a remarkably quiet, private sanctuary indoors and out.Inside,

  Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  78 E Main St, Stockbridge, MA 01262
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  /59

  $3,925,000

  • 8 Beds
  • 8.5 Baths
  • 6,000 Sq Ft

  17 Main St, Lenox, MA 01240

  Rare opportunity to own a beautifully restored Berkshire cottage at 17 Main Street, perfectly situated in the vibrant heart of downtown Lenox. This remarkable property, originally built in 1883 and once the residence of Gilded Age shipping magnate John Schermerhorn, combines historic elegance with modern comfort. The home underwent a comprehensive renovation between 2021 and 2025, including a new

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  17 Main St, Lenox, MA 01240
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  /50

  $575,000

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  24 Brunell Ave, Lenox, MA 01240

  Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living

  Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

  24 Brunell Ave, Lenox, MA 01240
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  /31

  $595,000

  $34K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,636 Sq Ft

  25 Valentine Ln, Lee, MA 01238

  IMMACULATE 3 BEDROOM APARTMENT WITH DECK and ONE BEDROOM APARTMENT in SOUTH LEE on a quiet cul de sac. Zoned 2 family, partially fenced back yard, attached garage, CENTRAL AIR CONDITIONING -BRAND NEW VINYL SIDING DECEMBER 2025.

  Rosemary Baumann HOUSATONIC REAL ESTATE

  25 Valentine Ln, Lee, MA 01238
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  /18

  $499,000

  • 2 Beds
  • 1 Bath
  • 828 Sq Ft

  1 Massasoit Rd, Stockbridge, MA 01262

  Turnkey Berkshire Retreat Near Stockbridge Bowl & Tanglewood -Embrace effortless seasonal living in this beautifully maintained, vintage three-season cottage. Nestled on a quiet, unpaved lane in the desirable Mahkeenac Heights community, this two-bedroom home offers the quintessential Berkshires getaway. Recent thoughtful updates include fresh flooring and an opened-up floor plan that

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1 Massasoit Rd, Stockbridge, MA 01262
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  /2

  $69,000

  • Land
  • 3.3 Acres
  • $20,909 per Acre

  75 Woodland Rd, Lee, MA 01238

  Over 3 acres of wooded land on Woodland Road in Lee near October Mountain State Forest. Previously used for logging, this parcel features a wooded, sloping landscape. Convenient to downtown Lee & Lenox and easy access to the Massachusetts Turnpike. Additional pastoral 1 acre parcel available at 60 Woodland Rd., may be purchased together or separately. Buyers and buyer's agents to perform their

  Lisa Kelley MACCARO REAL ESTATE

  75 Woodland Rd, Lee, MA 01238
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  /49

  $950,000

  $110K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  6 Manitauk Heights, Stockbridge, MA 01262

  Just two miles from the center of Stockbridge, this beautiful four bedroom, three and a half bathroom home offers privacy, space and exceptional indoor outdoor living. The spacious primary suite features a large ensuite bath and separate his and her closets, and an additional closet with direct access to a full length deck shared access with the living room. The open floor plan connects the

  Patricia Andrew STONE HOUSE PROPERTIES, LLC

  6 Manitauk Heights, Stockbridge, MA 01262
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  /50

  $1,999,000

  $996K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,932 Sq Ft

  10 Mahkeenac Shores Rd, Stockbridge, MA 01262

  Experience the best of Berkshire living in this stunning contemporary waterfront home on Stockbridge Bowl. Thoughtfully designed, this 4 BR, 3 full bath year 'round home offers a seamless blend of modern comfort and natural beauty! Sunlight pours through expansive windows, framing breathtaking water views from nearly every room. The open concept living space is anchored by a striking double sided

  Mary Jo Piretti PIRETTI REAL ESTATE

  10 Mahkeenac Shores Rd, Stockbridge, MA 01262
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  /32

  $349,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  880 East St Unit 10C, Lee, MA 01238

  Immaculate unit in move-in condition. 1st floor bedroom and a 1st floor stall shower with glass door. Hugh 3 season room with glass and screens to enjoy the Berkshire air. Hardwood floors in living and dining area. Upscale stainless steel refrigerator and Bosch Dishwasher. Two bedrooms and full bath with tub/shower upstairs. Unfinished lower level with work bench, brand new washer and (older)

  Susan Baum BERKSHIRE HOMES AND CONDOS

  880 East St Unit 10C, Lee, MA 01238
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  /59

  $1,595,000

  $255K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 4,952 Sq Ft

  1 Devon Rd, Stockbridge, MA 01262

  A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The ''Ice House'' features its

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1 Devon Rd, Stockbridge, MA 01262
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  /119

  $1,350,000

  • 12 Beds
  • 7 Baths
  • 7,956 Sq Ft

  45 Forest St, Lee, MA 01238

  Attention Investors! Excellent 6-unit investment opportunity in Lee with strong existing income and flexible rental potential. Five of the six units have been renovated with premium finishes, complemented by a newer roof, updated electrical and newer heating systems--helping reduce near-term maintenance and capital needs. Currently operated with a mix of long-term and seasonal rentals, the

  Marc Bellora Lamacchia Realty, Inc. - Dalton

  45 Forest St, Lee, MA 01238

Showing Results 81 - 110, Page 3 of 3