Homes for Sale near Hillcrest Educational Centers

/8
$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
Explore Hillcrest Educational Centers
/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
/11
$450,000
- Land
- 3.44 Acres
- $130,814 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
/50
$820,000
- 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
/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
/33
$1,300,000
- 4 Beds
- 5 Baths
- 3,060 Sq Ft
201 Chanterwood Rd, Lee, MA 01238

Set in the heart of the Berkshires of Lee, Mass, this beautifully maintained 4-bedroom home captures the essence of Berkshire living with panoramic, elevated views for all 4 seasons that will leave you speechless; particularly in Autumn, when views in the Berkshires explode with color. A 4th oversized garage below the house is the perfect place for all of your toys. Inside, the home offers 3

Susan Calkins STONE HOUSE PROPERTIES, LLC

201 Chanterwood Rd, Lee, MA 01238
/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
/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
/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
/74
$1,375,000
- 4 Beds
- 3.5 Baths
- 3,724 Sq Ft
5 Silver Mine Ln, West Stockbridge, MA 01266

Tucked at the end of a quiet cul-de-sac just minutes from Tanglewood, this light-filled country contemporary is designed for easy Berkshire living, with bright open spaces, a convenient first-floor primary suite, and seamless indoor-outdoor flow. Mornings begin in a sunlit kitchen that opens effortlessly to the main living areas, while a vaulted great room with gas fireplace creates a natural

Conor Meehan STONE HOUSE PROPERTIES, LLC

5 Silver Mine Ln, West Stockbridge, MA 01266
/51
$2,100,000
- 4 Beds
- 4 Baths
- 2,738 Sq Ft
8 Yale Hill Rd, Stockbridge, MA 01262

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

8 Yale Hill Rd, Stockbridge, MA 01262
/58
$1,199,000
- 6 Beds
- 3.5 Baths
- 4,188 Sq Ft
21 Stockbridge Rd, West Stockbridge, MA 01266

Originally built with classic 19th century detail, this 6 bedroom, 3.5 bath Colonial/Victorian has been thoughtfully expanded and renovated, carefully embellishing its original character with today's sought-after conveniences. Elegantly spacious rooms with high ceilings and tall windows lead to the well-designed kitchen, where you'll find 2 copper sinks, Wolf double ovens, pot filler, warming

Sheila Thunfors STONE HOUSE PROPERTIES, LLC

21 Stockbridge Rd, West Stockbridge, MA 01266
/45
$847,000
- 3 Beds
- 2.5 Baths
- 2,680 Sq Ft
63 Sherwood Dr, Lenox, MA 01240

Don't miss this Lenox beauty! Tucked away on a quiet street and abutting preserved land, this colonial is a must see. Main level features hardwood flooring, living room with crown molding, formal dining w. large bay window, open updated kitchen with extensive storage. Family room with gas fireplace opens to spacious screened porch. First floor laundry and half bath. Three bedrooms on the upper

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

63 Sherwood Dr, Lenox, MA 01240
/41
$995,000
- 4 Beds
- 5 Baths
- 6,300 Sq Ft
160 High St, Lee, MA 01238

Stunning architect designed space with soaring ceilings, floating staircases and numerous high-end features. Ideally situated on nearly 3/4 acre abutting an 18-acre nature reserve. Just a short walk to downtown Lee shops and restaurants. Lots of room for a pool, tennis court, and/or pickleball court. Minutes from the best places in the Berkshires. Great investment opportunity with the nearby $100

Jason Saphire www.HomeZu.com

160 High St, Lee, MA 01238
/78
$850,000
- 5 Beds
- 3 Baths
- 3,405 Sq Ft
36 Dunmore Ct, Lenox, MA 01240

Located in one of Lenox most sought after neighborhoods. Surrounded by woods, it gives you a rural feel, yet you're only minutes to the center of town. This Home features 5 bedrooms 3 Full Bathrooms and a Den with a connecting door to the 1st floor bath which gives you the options of a 6th Bedroom / Suite, Large finished sunroom, Family room with fireplace, a beautiful Kitchen, Combined Formal

Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

36 Dunmore Ct, Lenox, MA 01240
/42
$645,000
- 5 Beds
- 3.5 Baths
- 3,374 Sq Ft
100 S Prospect St, Lee, MA 01238

Tucked at the end of a peaceful cul-de-sac, this 3,300+sqft Cape is a rarity in today's market - a sprawling main home with the addition of a separate in-law/guest apartment. The main wing shines with refinished wide-plank wood floors, gas fireplace, and premium renovations, including a new chef's kitchen and bathrooms. Upstairs features three gracious bedrooms, including a primary suite with

John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

100 S Prospect St, Lee, MA 01238
/60
$1,350,000
- 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
/45
$349,900
- 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
/29
$675,000
- 3 Beds
- 1.5 Baths
- 1,562 Sq Ft
18 Willow Ln, Lenox, MA 01240

Nestled on a peaceful street, this inviting 3 bedroom, 1.5 bath home offers the perfect blend of comfort and convenience. Step inside to find a bright and welcoming living space filled with natural light, a cozy dining area, and a functional kitchen ready for your personal touch. The three bedrooms provide plenty of room for family, guests, or a home office, while the updated half bath adds extra

Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

18 Willow Ln, Lenox, MA 01240
/84
$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
/14
$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
/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
/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
/30
$679,000
- 4 Beds
- 3.5 Baths
- 1,843 Sq Ft
28 Evergreen Trail Unit 28, Lenox, MA 01240

Custom designed 4 BR, 3.5 bath Townhome with Kennedy Park in your back yard! A one owner home with many upgrades make this one of the most desirable in Lenox Woods. Open floor plan with gorgeous kitchen, granite countertops, tile floors & high backsplash, stainless, upgraded appliances and walk in pantry; stone fireplace enjoyed by all the common spaces; first floor en-suite BR; screened porch

Mary Jo Piretti PIRETTI REAL ESTATE

28 Evergreen Trail Unit 28, 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
/13
$171,500
- Land
- 6.8 Acres
- $25,221 per Acre
2447 State Rd, Richmond, MA 01254

Set along State Rd. in Richmond spans 6.80 acres of partially cleared land with approximately 155 feet of frontage. The existing structure is a tear down, opening the door for new construction within the Residential-Agricultural District C. Property has a well is on site and electric service at the street. The landscape offers a mix of open space with a slight slope and natural surroundings. This

Cory Evangelisto NOCHER REALTY

2447 State Rd, Richmond, MA 01254
/2
$59,000
- 3 Beds
- 1 Bath
- 1,032 Sq Ft
82 Dublin St, Lee, MA 01238

Property has sustained fire and/or smoke damage. The extent of damage may not be fully known. Seller has not undertaken repairs and will not make any repairs and makes no representations or warranties as to the condition of the property. Buyer and buyer's agents to perform all due diligence. Property may have structural, electrical, environmental, and/or water damage related to the fire and

Lisa Kelley MACCARO REAL ESTATE

82 Dublin St, Lee, MA 01238
/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
/11
$85,000
- Land
- 9.44 Acres
- $9,004 per Acre
800 Cape St, Lee, MA 01238

Exceptional opportunity in East Lee! 9.44 acres located in the desirable RB zone offering a flexible mix of residential and business uses. This expansive parcel provides the ideal setting for a residence, live/work concept with plenty of room for creative possibilities. Enjoy a peaceful Berkshire setting while maintaining convenient access to Lee, Lenox, and the Mass Pike. Whether you are looking

Katie Soules WILLIAM RAVEIS REAL ESTATE

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

A newly built modern country home of rare quality and quiet sophistication, set on five private acres in the heart of Stockbridge.Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. Newly completed and never before lived in, this 4,000 sq ft residence sits on 5 private acres, just minutes to Lenox, downtown Stockbridge, and the Mass

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

21A Interlaken Rd, Stockbridge, MA 01262
/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
/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
/48
$324,500
- 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
/5
$495,000
- Land
- 19 Acres
- $26,053 per Acre
0 Mohawk Lake Rd, Stockbridge, MA 01262

Wonderful opportunity to own 19 acres in Stockbridge for your dream home! The parcel features acres of deciduous trees with an abundance of peacefulness and tranquility. Gentle upward slope from the street then levels off. Providing several options for building. Freestanding fireplace/chimney remains from a former homestead. Norman Rockwell Museum, Chesterwood and Berkshire Botanical Gardens down

Debra Petrovsky DONOVAN REAL ESTATE

0 Mohawk Lake Rd, Stockbridge, MA 01262
/18
$315,000
- Land
- 10.52 Acres
- $29,943 per Acre
0 Lenox Rd Unit 249209, West Stockbridge, MA 01266

A rare opportunity to own two lots totaling 10.6 acres in sought-after West Stockbridge. Accessed by a shared driveway, the parcels offer flexibility for a private compound or two thoughtfully sited homes. Mowed walking paths wind through groves of mature trees and the partially cleared landscape, creating a peaceful setting with a natural balance of privacy and usable space. The property

Conor Meehan STONE HOUSE PROPERTIES, LLC

0 Lenox Rd Unit 249209, West Stockbridge, MA 01266
/39
$367,500 Open Sat 11AM - 1PM
- 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
/28
$564,900
- 3 Beds
- 2.5 Baths
- 1,848 Sq Ft
15 Martin Ave, Lee, MA 01238

Well-maintained 3-bedroom, 2.5-bath ranch offering over 1,800 sq ft of comfortable living space. This home features a spacious upper-level bonus room with a fireplace, perfect for a family room, office, or entertaining space. The main level offers a functional layout with bright living areas and three bedrooms, providing flexibility for a variety of uses. A finished basement adds even more living

Jesse Dimitropolis RE/MAX COMPASS

15 Martin Ave, Lee, MA 01238

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