Homes for Sale near Hillcrest Educational Centers

/39
$895,000
- 4 Beds
- 2 Baths
- 2,515 Sq Ft
10 Prospect Hill Rd, Stockbridge, MA 01262

Offered for the first time in more than forty years, this c.1880 residence presents a rare opportunity to own a substantial property on coveted Prospect Hill Road, one of Stockbridge's most desirable addresses. Set privately on 3.5 acres just moments from the center of Stockbridge, the property offers the increasingly rare combination of privacy, acreage, and location that defines some of the

Selina Lamb

BIRCH PROPERTIES

10 Prospect Hill Rd, Stockbridge, MA 01262
Explore Hillcrest Educational Centers
/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

L16 Reservoir Rd, Out-Of State, MA 99999
/11
$450,000

$150K PRICE DROP
- 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.

117 Lime Kiln Rd, Lenox, MA 01240
/50
$820,000

$64K PRICE DROP
- 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

9 Castle Hill Rd, Stockbridge, MA 01262
/36
$895,000
- 4 Beds
- 2 Baths
- 2,515 Sq Ft
10 Prospect Hill, Stockbridge, MA 01263

Rare opportunity on coveted Prospect Hill Road in Stockbridge. Offered for the first time in more than 40 years, this c.1880 residence is privately set on 3.5 acres just moments from downtown Stockbridge, the Red Lion Inn, Tanglewood, Lenox, and the Berkshires' renowned cultural attractions. The home offers approximately 2,515 square feet with wide-plank floors, exposed brick, wood beams,

Selina Lamb

Birch Properties

10 Prospect Hill, Stockbridge, MA 01263
/84
$1,650,000

Open Sat 10AM - 11:30AM
- 7 Beds
- 7 Baths
- 5,693 Sq Ft
20 E Dugway Rd, Lenox, MA 01240

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to

Nick Geranios

WILLIAM PITT SOTHEBY'S - LENOX

20 E Dugway Rd, Lenox, MA 01240
/14
$69,499
- 2 Beds
- 1 Bath
- 400 Sq Ft
40 Albany Rd Unit 3, West Stockbridge, MA 01266

MUST SEE: Small completely remodeled and newly renovated 2-bedroom home. Much nicer than a tiny home. Located in the beautiful Berkshires with scenic pond and mountain views in an all-age mobile home park community. Fully applianced kitchen, tons of cabinets, all new flooring, freshly painted, vinyl tilt-out windows and one-level living. Small pets welcomed. New mail center and small yard for

Thomas Lennon

Keller Williams Elite

40 Albany Rd Unit 3, West Stockbridge, MA 01266
/8
$69,500

$10K PRICE DROP
- 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

3 Jennifer Ln, West Stockbridge, MA 01266
/37
$685,000
- 4 Beds
- 2 Baths
- 3,599 Sq Ft
2507 State Rd, Richmond, MA 01254

Welcome home! This magnificent 13.3-acre estate is rich in history and brimming with enchanting features. Nestled in a county setting, this property offers a connection with the outdoors for nature lovers and recreational activities. A low-maintenance wild garden of perennial flowers and shrubs produces a kaleidoscope of colors during the spring and summer seasons, while trails through the

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

2507 State Rd, Richmond, MA 01254
/24
$389,900
- 3 Beds
- 2 Baths
- 2,178 Sq Ft
38 Hubbard St, Lenox, MA 01240

Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space.

Mariah Worth Lamacchia Realty, Inc. - Dalton

38 Hubbard St, Lenox, MA 01240
/103
$874,900
- 5 Beds
- 6 Baths
- 3,241 Sq Ft
4 Stockbridge Rd, West Stockbridge, MA 01266

Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and

Doug Collins Lamacchia Realty, Inc. - Dalton

4 Stockbridge Rd, West Stockbridge, MA 01266
/25
$699,999

$45K PRICE DROP
- 6 Beds
- 4 Baths
- 2,730 Sq Ft
34 Church St, Stockbridge, MA 01262

Rare opportunity to own a substantial two-family home with a potential bonus Airbnb cottage in one of the most desirable locations in the Berkshires. Overlooking meadows, sheep pastures, mountains, and Naumkeag, this special property is also just a short walk to Stockbridge Main Street. Each spacious unit offers 3 bedrooms, 1.5 baths, and hardwood floors throughout. The grounds are truly magical,

Lisa Kelley MACCARO REAL ESTATE

34 Church St, Stockbridge, MA 01262
/68
$895,000
- 6 Beds
- 4 Baths
- 2,561 Sq Ft
3 Cone Hill Rd, West Stockbridge, MA 01266

Welcome to 3 Cone Hill in the heart of the Berkshires. This rustic retreat is the epitome of a classic country compound that's been lovingly cared for and enjoyed by the same family for many years. Minutes to Tanglewood, this 2+ acre lot hold more fun and relaxation than most large estates. Sitting over Cone Brook, you'll enjoy listening to the babbling water from your screened-in gazebo. After

Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

3 Cone Hill Rd, West Stockbridge, MA 01266
/53
$1,190,000

$485K PRICE DROP
- 4 Beds
- 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
$329,900

$59K PRICE DROP
- 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
$649,000

$26K PRICE DROP
- 3 Beds
- 2 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
/17
$335,000

$33K PRICE DROP
- 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
$1,625,000

$50K PRICE DROP
- 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
/7
$1,800
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
55 Crystal St Unit 7, Lenox, MA 01240

Bright and inviting one-bedroom apartment with a spacious open kitchen, dining, and living area. Original wood floors and large windows add warmth, charm, and natural light throughout the space. Conveniently located in Lenox, close to shopping, restaurants, and Tanglewood. Heat and trash removal are included in the rent, and the building offers convenient coin-operated laundry facilities. Listed

Christian Garner NOCHER REALTY

55 Crystal St Unit 7, 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
/66
$2,399,000
- 4 Beds
- 5 Baths
- 5,533 Sq Ft
430 Lenox Rd, Richmond, MA 01254

Nestled in the rolling foothills of the Berkshire Hills, this beautifully designed contemporary home offers the perfect blend of warmth, comfort, and modern living. The heart of the home is a chef's kitchen with a sunny breakfast nook that opens seamlessly to the living room, where a dramatic floor-to-ceiling stone fireplace creates an inviting focal point. Just beyond, a screened porch provides

Nikki Carchedi STONE HOUSE PROPERTIES, LLC

430 Lenox Rd, Richmond, MA 01254
/13
$151,500

$20K PRICE DROP
- Land
- 6.8 Acres
- $22,279 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
/42
$675,000

Open Sat 11AM - 1PM
- 3 Beds
- 2 Baths
- 1,736 Sq Ft
4 Lenox Rd, West Stockbridge, MA 01266

This charming New England farmhouse is located in the heart of West Stockbridge Village. You'll feel right at home in this updated, open-floor-plan, 3 bedroom, two bath home featuring beautiful hardwood floors throughout. The modern kitchen with newer appliances, butcher block island, and breakfast bar is perfect for entertaining as well as enjoying quiet home-cooked meals. Relax on your spacious

Leslie Claus Van Hise BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

4 Lenox Rd, West Stockbridge, MA 01266
/32
$629,000
- 4 Beds
- 3 Baths
- 1,636 Sq Ft
25 Valentine Ln, Lee, MA 01238

IMMACULATE 3 BEDROOM COLONIAL with IN LAW APARTMENT in SOUTH LEE on a quiet cul de sac. Zoned 2 family, Partially fenced back yard, attached garage and central air conditioning. Great investment or family home.

Rosemary Baumann HOUSATONIC REAL ESTATE

25 Valentine Ln, Lee, MA 01238
/8
$449,000

$50K PRICE DROP
- 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
$799,000

$61K PRICE DROP
- 3 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
/30
$795,000
- 3 Beds
- 3 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
/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
/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
/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
/35
$399,000
- 3 Beds
- 1 Bath
- 912 Sq Ft
135 Tamarack Ave, Lee, MA 01238

Open House: 6/20 from 10:00-12:00. Charming three-bedroom, one full bath ranch offering the ease and convenience of one level living in a highly desirable neighborhood. Situated on a spacious lot, just shy of a half-acre, this home features a large fenced backyard perfect for entertaining, gardening or simply enjoying the outdoors. Wrap around deck overlooking above ground pool, creating the

Lisa Kelley MACCARO REAL ESTATE

135 Tamarack Ave, Lee, MA 01238
/41
$575,000
- 3 Beds
- 2 Baths
- 1,920 Sq Ft
55 Paul Dr, Lee, MA 01238

Nestled in a quiet, private neighborhood, this beautifully maintained ranch offers easy single-level living with minimal steps for entry and a seamless flow throughout. Ideally situated in the heart of the Berkshires, you'll be minutes from Tanglewood, Jacob's Pillow, Shakespeare & Company, the Norman Rockwell Museum, and Berkshire Botanical Garden. The updated kitchen features quartz

Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

55 Paul Dr, Lee, MA 01238
/30
$795,000
- 3 Beds
- 3 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
/19
$900,000
- 11 Beds
- 6 Baths
- 4,863 Sq Ft
Unlisted Address

Stockbridge Investment Opportunity Fully Rented In Town 5-Family Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures. Can also be purchased as part of a investment portfolio 35 Main Street West Stockbridge ,Ma MLS# 249539

Matt Carlino MACCARO REAL ESTATE

Unlisted Address
/7
$88,000

$12K PRICE DROP
- 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
/43
$1,550,000

Coming Soon
- 4 Beds
- 5 Baths
- 3,542 Sq Ft
650 Mallard Ln, Lee, MA 01238

Experience refined Berkshire living at Devon Meadows, one of the area's most desirable luxury condominium communities. This beautifully appointed residence offers the ease of a first-floor primary suite combined with sophisticated design and exceptional comfort throughout.The open-concept floor plan features soaring ceilings, abundant natural light, and elegant modern finishes. The chef's

Paula McLean PAULA MCLEAN REALTORS INC.

650 Mallard Ln, Lee, MA 01238
/26
$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 large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the stone bridge, and

Katie Soules WILLIAM RAVEIS - BERKSHIRE

286 Lee Rd, Lenox, MA 01240
/46
$680,000
- 4 Beds
- 2 Baths
- 2,040 Sq Ft
7 Swamp, West Stockbridge, MA 01266

Don't miss this rare opportunity to own this private, meticulously maintained waterfront sanctuary. The grounds feature a charming English garden, an expansive deck and a private dock for launching kayaks, offering outdoor living at its best. The main level features an eat-in kitchen with custom cabinetry, a living room, sunroom ideal for gatherings, an office, mudroom with laundry and a

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

7 Swamp, West Stockbridge, MA 01266
/29
$299,000
- 2 Beds
- 3 Baths
- 1,552 Sq Ft
5 Rolling Hills Unit 4, Lenox, MA 01240

Move right into this beautifully updated, light-filled condo offering the perfect blend of comfort and elevated style. Featuring an open floor plan, tall ceilings, and a beautiful renovated kitchen with newer appliances, this home is designed for effortless living and entertaining. Enjoy flexible bonus space in the finished lower level--ideal for a cozy lounge, home office, or guest retreat, plus

Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

5 Rolling Hills Unit 4, Lenox, MA 01240
/78
$2,100,000
- 5 Beds
- 4 Baths
- 3,387 Sq Ft
19 Cliffwood St, Lenox, MA 01240

Iconic Lenox home: very rarely does a home with this historic integrity come on the market...now is your time to continue its legacy . Built in 1915 as one of the focal points of Cliffwood Street, this charming home has been updated for today's life style without sacrificing its significant architectural details. Beautiful common rooms including a dream kitchen with marble counters, formal Dining

Mary Jo Piretti PIRETTI REAL ESTATE

19 Cliffwood St, Lenox, MA 01240

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