Homes for Sale near Hillcrest Educational Centers

/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
Explore Hillcrest Educational Centers
/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
$1,280,000
- 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
/7
$79,900
- 2 Beds
- 1 Bath
- 550 Sq Ft
3 Jennifer Ln, West Stockbridge, MA 01266

Nicely remodeled 2 bedroom trailer with fireplace and 2 baths. Park rent is $399.56 per month.

John Ciepiela

BISHOP WEST REAL ESTATE

(413) 741-1606

3 Jennifer Ln, West Stockbridge, MA 01266
/42
$2,649,000
- 6 Beds
- 6.5 Baths
- 6,225 Sq Ft
250 West St, Lenox, MA 01240

Seconds—not minutes—from Tanglewood’s main gate, this reimagined contemporary estate in Lenox is tucked into a sunlit woodland setting offering rare privacy and unrivaled proximity. Originally built in 2017 and completely updated in 2020, the home features soaring ceilings, rich mahogany and cherry finishes, a chef’s kitchen, and multiple entertaining spaces. The ground-floor primary suite is

Selina Lamb

Birch Properties

(413) 423-1264

250 West St, Lenox, MA 01240
/4
$215,000
- Land
- 14.3 Acres
- $15,035 per Acre
L16 Reservoir Rd, Out-Of State, MA 99999

Discover an unparalleled opportunity with this stunning 14.3-acre parcel, perfect for building your dream home or if needed, subdividing into its original three lots. Featuring a pre-installed driveway, electrical service with a transformer, and a large 36 x 50 foundation that was started for a garage/barn, this property is both convenient and versatile. Enjoy the natural beauty of streams,

Gary Fuls Jr

Gary L Fuls DBA Re/MAX Transit

(866) 819-0148

L16 Reservoir Rd, Out-Of State, MA 99999
/4
$500,000
- Land
- 3.44 Acres
- $145,349 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
$1,280,000
- 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
/42
$435,000
- 3 Beds
- 1.5 Baths
- 1,293 Sq Ft
184 Washington Mountain Rd, Lee, MA 01238

Welcome to 184 Washington Mountain Rd -- an inviting three-bedroom, one-and-a-half bath raised ranch ideally situated in a quiet, highly desirable location. This thoughtfully updated home features a stylish eat-in kitchen that flows seamlessly into a bright, open living area with direct access to a sunroom, creating the perfect space for relaxing or entertaining year-round. Beautiful hardwood

The Mazzeo Duo BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

184 Washington Mountain Rd, Lee, MA 01238
/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
/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
/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
/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
/50
$7,975,000
- 8 Beds
- 6.5 Baths
- 9,364 Sq Ft
399 Under Mountain Rd, Lenox, MA 01240

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

399 Under Mountain Rd, Lenox, MA 01240
/3
$750,000
- Land
- 131.69 Acres
- $5,695 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
/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
/53
$449,000
- 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
/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
/6
$34,900
- 1 Bed
- 780 Sq Ft
155 Water St Unit 5, Lee, MA 01238

Opportunity awaits in Lee! Located at 155 Water Street #5, this mobile home has been fully gutted and is ready for a complete renovation. A true blank slate, offering endless potential for investors, contractors, or buyers looking to customize from the ground up.Major improvements have already been started, including a brand-new roof and new doors. Custom-sized windows have been purchased and are

Cheryl Ryan BISHOP WEST REAL ESTATE

155 Water St Unit 5, Lee, MA 01238
/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
/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,

Lance Vermeulen LANCE VERMEULEN RE, INC

18 Goodrich St, Stockbridge, MA 01262
/8
$449,000
- 8 Beds
- 4 Baths
- 2,657 Sq Ft
180 Center St, Lee, MA 01238

Huge price adjustment! 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

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
$974,999
- 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
/35
$535,000
- 3 Beds
- 2 Baths
- 1,753 Sq Ft
31 Saint Ann's Ave, Lenox, MA 01240

This charming bungalow offers the Lenox lifestyle you've been dreaming of. Tucked on a quiet dead-end street just steps from downtown, you can grab morning coffee, enjoy dinner at local favorites, or spend an evening at Tanglewood before strolling home under the stars.Inside, about 1,700 square feet of warm, inviting space blends character and comfort, creating a perfect retreat for every season.

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
/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
/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
/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
/59
$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
/42
$559,000
- 3 Beds
- 2 Baths
- 1,842 Sq Ft
16 Swamp Rd, West Stockbridge, MA 01266

The George Tyler Homestead appears on West Stockbridge maps as early as 1855. This charming 3-bedroom cottage exudes warmth and character with plenty of original detail. The wood-paneled living room features a handsome brick hearth with beehive oven and beautifully aged pine floors. The L-shaped kitchen offers ample storage and opens to a formal dining room, where a large window overlooks the

Vashti Poor WILLIAM RAVEIS - BERKSHIRE

16 Swamp Rd, West Stockbridge, MA 01266
/43
$495,000
- 3 Beds
- 1.5 Baths
- 1,686 Sq Ft
155 Laurel St, Lee, MA 01238

This thoughtfully updated home blends warmth, comfort, and history. An amazing front porch welcomes you before you even step inside, and the short walk to downtown or quick drive to the lake offers an easy, connected Berkshire lifestyle. Inside, bright and inviting rooms and beautiful wood floors create a natural sense of warmth, while the layout makes everyday living feel effortless. Flexible

Katie Soules WILLIAM RAVEIS REAL ESTATE

155 Laurel St, Lee, MA 01238

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