Homes for Sale near Hillcrest Educational Centers

/8
$998,000
- Land
- 9.1 Acres
- $109,670 per Acre
19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

Exceptional ready-to-build opportunity in the heart of the Berkshires. This rare 9.1-acre estate parcel offers direct frontage on tranquil Lily Pond, a private, non-motorized body of water known for its serenity, protected natural setting, and long, unobstructed views. A winding driveway follows a charming brook and leads across a brand-new bridge to an incredibly private pond-front building

Selina Lamb

Birch Properties

(413) 343-4919

19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
Explore Hillcrest Educational Centers
/54
$2,649,000
- 6 Beds
- 6.5 Baths
- 4,289 Sq Ft
250 West St, Lenox, MA 01240

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

Selina Lamb

BIRCH PROPERTIES

(413) 423-1264

250 West St, Lenox, MA 01240
/6
$395,000
- Land
- 3.3 Acres
- $119,697 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

BIRCH PROPERTIES

(413) 722-5098

9 Wheatleigh Dr, Stockbridge, MA 01262
/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,

Selina Lamb

BIRCH PROPERTIES

(413) 269-8632

9 Castle Hill Rd, Stockbridge, MA 01262
/42
$1,650,000
- 4 Beds
- 3 Baths
- 7,027 Sq Ft
17 East St, Stockbridge, MA 01262

Architecturally iconic and rich with history, this brick Federal home and its gracefully conceived mid-1990s expansion offer a rare opportunity for a buyer with vision. The last major renovation paired the 1830s structure with an addition that respects the original proportions while opening new possibilities for contemporary living. Set along the Stockbridge–Lenox corridor on 13+/- acres (9

Selina Lamb

Birch Properties

(413) 300-6860

17 East St, Stockbridge, MA 01262
/42
$1,420,000
- 3 Beds
- 4.5 Baths
- 2,691 Sq Ft
18 Highcrest Rd Unit 20, Lenox, MA 01240

Selina Lamb

Birch Properties

(413) 591-5654

18 Highcrest Rd Unit 20, Lenox, MA 01240
/4
$600,000
- Land
- 3.44 Acres
- $174,419 per Acre
117 Lime Kiln Rd, Lenox, MA 01240

Ready to build! Build your own Berkshire Home on this beautiful 3.44 acre parcel in the heart of the Berkshires! The land is partially cleared and ready for construction, with septic design plans already with public water and power on the street. Set on a quiet road, this property offers privacy with a true Berkshire feel while being close to many cultural attractions including, Tanglewood, The

Laura Arseneau

PAULA MCLEAN REALTORS INC.

(413) 393-2997

117 Lime Kiln 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

Selina Lamb

BIRCH PROPERTIES

(413) 319-9976

18 Highcrest Rd, Lenox, MA 01240
/6
$395,000
- Land
- 3.3 Acres
- $119,697 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

Birch Properties

(413) 343-5283

9 Wheatleigh Dr, Stockbridge, MA 01262
/21
$1,400,000
- Land
- 14.6 Acres
- $95,890 per Acre
286 Lee Rd, Lenox, MA 01240

A ONCE IN A LIFETIME OPPORTUNITY TO BUILD YOUR DREAM HOME ON A SPECTACULAR, 14 ACRE, WATERFRONT PROPERTY IN THE HEART OF THE BERKSHIRES. PRIVATE, QUIET, BUT NOT ISOLATED. FROM YOUR NEW RESIDENCE, BEAUTIFUL LAUREL LAKE IS AN EASY STROLL DOWN THE BOARDWALK TO YOUR PRIVATE DOCK AND SITTING AREA. FIVE MINUTES TO DOWNTOWN LENOX, TEN MINUTES TO TANGLEWOOD AND CONVENIENT TO ALL THE BERKSHIRES HAS TO

Allen Bassen BERKSHIRE HOMES AND CONDOS

286 Lee Rd, Lenox, MA 01240
/45
$369,000
- 4 Beds
- 2 Baths
- 1,728 Sq Ft
205 High St, Lee, MA 01238

Enjoy downtown living in this 4 Bedroom 2 Bath New England farmhouse. Built in the early20th century, this home has a diverse use of residential, commercial or mixed use on a residential street. The kitchen has been updated with plenty of cabinet space. A cozy living room fireplace and a enclosed porch with numerous windows that welcome fresh summertime breezes and a patio for summer leisure

Anthony Caropreso MACCARO REAL ESTATE

205 High St, Lee, MA 01238
/40
$389,000
- 3 Beds
- 1 Bath
- 1,269 Sq Ft
26 Lenox Rd, West Stockbridge, MA 01266

1900's cottage set above the village of West Stockbridge. Open plan living with updated kitchen and bath, with laundry tucked in below the stairs and second floor has three bedrooms. Fenced yard creating a nice private space with wraparound deck. Shed at the back of the property providing a lovely additional space.

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

26 Lenox Rd, West Stockbridge, MA 01266
/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
/52
$1,675,000
- 12 Beds
- 7 Baths
- 8,881 Sq Ft
29 Main St, West Stockbridge, MA 01266

Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully

Suzann Ward HOUSATONIC REAL ESTATE

29 Main St, West Stockbridge, MA 01266
/56
$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
/3
$975,000
- Land
- 131.69 Acres
- $7,404 per Acre
0 Lenox Rd Unit 246122, West Stockbridge, MA 01266

This is a generous hillside parcel with a perc and potential views to the west. It is just over the hill from Stockbridge Bowl and Tanglewood, in an area of fine homes.

Jim Stark L. J. STARK AND CO.

0 Lenox Rd Unit 246122, West Stockbridge, MA 01266
/53
$479,000
- 3 Beds
- 2 Baths
- 1,720 Sq Ft
500 Walker St, Lenox, MA 01242

Charming 3 bedroom, 2 bath spacious New England Farmhouse with wide board pine floors, updated kitchen & baths, natural gas heat & hot water, vinyl replacement windows, home office/den and first floor laundry room/mudroom. New beautiful 20x18 bluestone patio & retaining wall installed in 2022.

Matt Carlino MACCARO REAL ESTATE

500 Walker St, Lenox, MA 01242
/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
$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
/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
/64
$1,250,000
- 4 Beds
- 4.5 Baths
- 3,395 Sq Ft
82 Stockbridge Terrace, Lee, MA 01238

Prepare to be wowed when you visit this fully furnished luxury condo at Stockbridge Terrace! Move-in ready and lightly lived in, this one-owner home features many custom finishes. Seeking one-level living? This condo delivers. Entertain in style with open floor plan. The living/great room's centerpiece is the stone fireplace, oversized windows and cherry floors. Enjoy the formal dining room or

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

82 Stockbridge Terrace, Lee, MA 01238
/63
$1,300,000
- 4 Beds
- 2 Baths
- 2,548 Sq Ft
18 Goodrich St, Stockbridge, MA 01262

This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal,

Robert Doerr LANCE VERMEULEN RE, INC., LENOX

18 Goodrich St, Stockbridge, MA 01262
/8
$499,000
- 8 Beds
- 8 Baths
- 2,657 Sq Ft
180 Center St, Lee, MA 01238

Discover an exceptional investment opportunity to own two duplex homes on a single parcel, perfect for investors looking for a practical investment in the town of Lee. Four units total, these properties are ideal for generating consistent rental income. Close to downtown, shopping, major employers as well as banking and all popular Berkshire attractions. Tenants enjoy attached, private garaged

Tim Gallagher STONE HOUSE PROPERTIES, LLC

180 Center St, Lee, MA 01238
/49
$859,900
- 4 Beds
- 3 Baths
- 2,732 Sq Ft
135 East St, Lee, MA 01238

Custom built home! Embrace the eastern views and warmth of New England's Mountains from the beautiful open front porch! Amazing custom home built by a true craftsman. Beautiful natural wood elements & exposed beams throughout, make for a wonderful Berkshire retreat! Large custom kitchen with granite & butcher block countertops, open dining room for easy entertaining with double French doors lead

Lisa Kelley MACCARO REAL ESTATE

135 East St, Lee, MA 01238
/48
$999,999
- 6 Beds
- 9 Baths
- 4,652 Sq Ft
560 Stockbridge Rd, Lee, MA 01238

Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room,

Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

560 Stockbridge Rd, Lee, MA 01238
/43
$3,850,000
- 4 Beds
- 3.5 Baths
- 4,000 Sq Ft
21A Interlaken Rd, Stockbridge, MA 01262

Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

21A Interlaken Rd, Stockbridge, MA 01262
/26
$535,000
- 3 Beds
- 2 Baths
- 1,753 Sq Ft
31 Saint Ann's Ave, Lenox, MA 01240

Tucked away on a quiet dead-end street just steps from the heart of Lenox, this charming bungalow offers the kind of lifestyle people come to the Berkshires dreaming about. From here, you can walk into town for morning coffee, linger over dinner at your favorite local spot, or head to Tanglewood on a summer evening and travel back home under the stars. It's peaceful and private, yet perfectly

Amy Shufelt BERKSHIRE LISTINGS

31 Saint Ann's Ave, Lenox, MA 01240
/16
$499,994
- Land
- 10.02 Acres
- $49,885 per Acre
0 Swamp Rd, Richmond, MA 01254

This 10-acre parcel in scenic Richmond, available for the first time in generations, offers a rare chance to build your dream home in the heart of the Berkshires. Surrounded by open farmland and natural beauty, this property provides a peaceful and inspiring setting for a country retreat or a year-round residence. The land features gently rolling meadows filled with wildflowers and native ferns,

Conor Meehan STONE HOUSE PROPERTIES, LLC

0 Swamp Rd, Richmond, MA 01254
/7
$88,000
- Land
- 1.42 Acres
- $61,972 per Acre
0 East St Unit 235893, Lee, MA 01238

Two building lots being sold together with 324 feet of road frontage with an estimated 1.42 total acres. So, there are possibilities to build one or two house on the property. Site has access to electric water, sewer, and natural gas. There is one temporary approved curb cut.

Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

0 East St Unit 235893, Lee, MA 01238
/47
$337,500
- 2 Beds
- 3 Baths
- 1,552 Sq Ft
7 Rolling Hills Unit 7-1, Lenox, MA 01240

Think spring in the Berkshires and enjoy condo living in Lenox at Rolling Hills. Spacious end unit brings in natural light and offers two bedrooms/two baths on upper level with an additional full bath and family room/office on the finished lower level. In this unit owners have replaced the custom-sized slider and the windows adding to energy efficiency. Central a/c, natural gas. The former golf

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

7 Rolling Hills Unit 7-1, Lenox, MA 01240
/32
$549,000
- 2 Beds
- 1 Bath
- 1,300 Sq Ft
7 Park St, Stockbridge, MA 01262

Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The

Samantha Homeyer BIRCH PROPERTIES

7 Park St, Stockbridge, MA 01262
/5
$385,900
- Land
- 15.91 Acres
- $24,255 per Acre
2 New Lenox Rd, Lenox, MA 01240

Opportunity Knocks! Expansive Lenox parcel - currently 2 approved building lots (1.0 acre and 14.91 acres) w/ frontage on East Street and New Lenox Road. Seller has a proposed subdivision that would make it 4 lots (1.0 acre, 3.5 acres, 7.59 acres & 2.98 acres). Build your dream home or take advantage of this unbeatable development opportunity in highly sought after location! Water, sewer & gas on

Sean Taylor MORESI REAL ESTATE PARTNERS

2 New Lenox Rd, Lenox, MA 01240
/8
$1,269,000
- 6 Beds
- 4 Baths
- 3,334 Sq Ft
1574 Pleasant St, Lee, MA 01260

Ashley Rose NON-MEMBER / RECIPROCAL

1574 Pleasant St, Lee, MA 01260
/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
/56
$1,395,000
- 4 Beds
- 2 Baths
- 2,058 Sq Ft
45 Swamp, West Stockbridge, MA 01266

1950s retro home, rich with family history, situated on 30+ acres of land & offering expansive westerly views & gentle sloping fields. Pathways lead to Shaker Mill Pond & Cone Brook which run the entire length of the property. Interior features include 2 BRs, office & full bath on the main level, 2 BRs & full bath on the second floor, a quaint kitchen, & living room. Additionally, a fully heated

Paige Paluch LANCE VERMEULEN RE, INC

45 Swamp, West Stockbridge, MA 01266
/40
$384,000
- 3 Beds
- 1.5 Baths
- 1,677 Sq Ft
20 Moscow Rd, West Stockbridge, MA 01266

Short walk to quaint downtown West Stockbridge featuring local coffee shop, variety store, restaurants and shops. Just a few minutes to local theatres, music venues, Tanglewood, historic Stockbridge, and the Mass Pike. Beautiful open yard great for summer entertaining including cookouts, yard games or just relaxing and reading a book! Cozy fireplace for those beautiful snowy New England nights.

Mark Harris SIGNATURE ASSOCIATES

20 Moscow Rd, West Stockbridge, MA 01266
/30
$895,000
- 3 Beds
- 2.5 Baths
- 2,218 Sq Ft
200 Vanna #3 Old Stockbridge Rd, 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. This 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

Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

200 Vanna #3 Old Stockbridge Rd, Stockbridge, MA 01262
/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
/42
$1,399,900
- 12 Beds
- 7 Baths
- 7,956 Sq Ft
45 Forest St, Lee, MA 01238

This stunning 6-family home sits on 1.5 acres, a large lot that goes from Forest St to Silver St, a convenient location with easy access to the Mass Pike and just a couple minutes away from the Lee Outlets. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and

Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

45 Forest St, Lee, MA 01238
/19
$550,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
15 W Stockbridge, Stockbridge, MA 01262

The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect

C. Ethan Watt WILLIAM PITT SOTHEBY'S - SALISBURY

15 W Stockbridge, Stockbridge, MA 01262

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