Homes for Sale near Hillcrest Educational Foundation

/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
/11
$839,900
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
407 Churchill St, Pittsfield, MA 01201

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 3.59-acre lot (MLS # 248344), installed

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 475-9767

407 Churchill St, Pittsfield, MA 01201
/2
$39,900
- Land
- 0.15 Acre
- $266,000 per Acre
0 Courtland Place, Pittsfield, MA 01201

Cleared City lot with public water and sewer

John Ciepiela

BISHOP WEST REAL ESTATE

(413) 553-1360

0 Courtland Place, Pittsfield, MA 01201
/12
$139,900
- Land
- 3.59 Acres
- $38,969 per Acre
407 Churchill St, Pittsfield, MA 01201

Experience refined country living on this immaculate 3.59-acre estate parcel, mostly cleared prepared with an installed private well, perc test/soil evaluation complete, and underground electric in place. A septic easement benefits the property via a neighboring parcel. The HOA provides driveway and common-land maintenance. The restrictions and covenants in place ensure lasting elegance: minimum

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 216-4191

407 Churchill St, Pittsfield, MA 01201
/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
/2
$300,000
- 6 Beds
- 3 Baths
- 2,118 Sq Ft
27 Pleasant St, Pittsfield, MA 01201

THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 40-42 Henry Ave. Pittsfield, MA 01201 and 101-103 Lincoln St. Pittsfield, MA 01201. Acquire three multifamily package offered at $920,000. Income & expense and rent roll available under documents or upon request.

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 822-2695

27 Pleasant St, Pittsfield, MA 01201
/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
/8
$35,000
- Land
- 1.08 Acres
- $32,407 per Acre
Lot 25 Old Farm Ln, Pittsfield, MA 01201

This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas.Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and numerous

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

(413) 299-2220

Lot 25 Old Farm Ln, Pittsfield, MA 01201
/33
$299,900
- 4 Beds
- 1 Bath
- 1,170 Sq Ft
1990 East St, Pittsfield, MA 01201

Welcome home to this inviting 4-bedroom Cape at 1990 East in Pittsfield. This charming residence offers a warm, sun-filled layout with an updated kitchen and bath that combine comfort and modern style. A brand-new deck expands your living space outdoors, creating a perfect spot for morning coffee, casual dinners, or simply unwinding at the end of the day. Thoughtfully maintained and ready to

John Ciepiela

BISHOP WEST REAL ESTATE

(413) 486-5886

1990 East St, Pittsfield, MA 01201
/8
$25,000
- Land
- 1.51 Acres
- $16,556 per Acre
Lot #26 Old Farm Ln, Pittsfield, MA 01201

Old Farm Lane, Lot #26 offers the perfect blend of wooded privacy and neighborhood community, while being tucked away on a quiet cul-de-sac. Utilities are in place with public sewer, private well, underground electric + gas. This lot borders the Pittsfield State Forest and offers close proximity to other year-round activities. It is also a short drive to the cultural hubs of Lenox, Williamstown,

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

(413) 331-7250

Lot #26 Old Farm Ln, Pittsfield, MA 01201
/10
$109,900
- Land
- 2.14 Acres
- $51,355 per Acre
403 Churchill St, Pittsfield, MA 01201

Experience refined country living on this immaculate 2.14-acre estate parcel, mostly cleared prepared with an installed private well, 3 bedroom septic design and underground electric in place. There is an existing RDA plan approved which has expired and would need renewing for nearby wetlands on common land. The HOA provides driveway and common-land maintenance. The restrictions and covenants in

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 414-4478

403 Churchill St, Pittsfield, MA 01201
/9
$254,900
- Land
- 8.93 Acres
- $28,544 per Acre
411 Churchill St, Pittsfield, MA 01201

Experience refined country living on this immaculate 8.93-acre estate parcel, fully cleared and impeccably prepared with a private well, installed 4 bedroom septic system, underground electric tied in, and a 1,000-gallon underground propane tank. A proposed septic easement accommodates an abutting lot. The HOA provides driveway and common-land maintenance, with restrictions and covenants ensuring

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 359-6411

411 Churchill St, Pittsfield, MA 01201
/15
$110,000
- Land
- 4.62 Acres
- $23,810 per Acre
0 Dalton Division Rd, Pittsfield, MA 01201

Well located parcels with 4.2 acres of development land zoned RG with an attached .4 acre lot zoned R12. Sale includes all engineering work to date, including wetlands delineation, site plans, etc... All utilities available including water, sewer & natural gas. Possibilities include 19-20 Garden Style Apartments, 5 or 7 lot subdivision or a 3 lot ANR subdivision. Property abuts large apartment

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 366-3881

0 Dalton Division Rd, Pittsfield, MA 01201
/38
$312,000
- 3 Beds
- 1 Bath
- 1,394 Sq Ft
36 Pittsfield Ave, Pittsfield, MA 01201

Step into this charming 3-bedroom, 1-bath home tucked away in the comfortable Allendale Parkway neighborhood. With nearly a half acre of land, it could be your perfect blend of comfort and outdoor beauty.Inside, you'll find 1,394 sq. ft. of freshly painted living space with easy-care laminate floors. The first floor offers kitchen, dining room, and a spacious living room where a large bow window

Mary Smith

WILLIAM PITT SOTHEBY'S - LENOX

(413) 628-2060

36 Pittsfield Ave, Pittsfield, MA 01201
/11
$1,176,800
- 4 Beds
- 3.5 Baths
- 2,634 Sq Ft
411 Churchill St, Pittsfield, MA 01201

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 8.94-acre lot (MLS #248342), featuring a

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 343-4823

411 Churchill St, Pittsfield, MA 01201
/30
$277,500
- 2 Beds
- 2 Baths
- 1,227 Sq Ft
36 Churchill Crest Unit 36, Pittsfield, MA 01201

Enjoy the ease of single level living in this beautifully updated end unit, ranch style condominium, ideally situated in one of the most desirable locations within the complex. This light filled corner home offers an open concept living room, dining area, and kitchen featuring stainless appliances and thoughtful updates designed for effortless everyday living and entertaining. The inviting living

Nick Geranios

WILLIAM PITT SOTHEBY'S - LENOX

(413) 881-6439

36 Churchill Crest Unit 36, Pittsfield, MA 01201
/2
$300,000
- 6 Beds
- 4 Baths
- 4,136 Sq Ft
Unlisted Address

THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 40-42 Henry Ave. Pittsfield, MA 01201 and 27-31 Pleasant St. Pittsfield, MA 01201. Acquire this three multifamily package offered at $920,000. Income & expense and rent roll document available in documents and or upon request.

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 822-2695

Unlisted Address
/7
$809,900
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
403 Churchill St, Pittsfield, MA 01201

To Be Built - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 2.14-acre lot (MLS # 248343), featuring a private

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 741-2226

403 Churchill St, Pittsfield, MA 01201
/92
$699,900
- 4 Beds
- 5 Baths
- 2,748 Sq Ft
10 Lillybrook Rd, Pittsfield, MA 01201

Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full

Paul Clark

CLARK REALTY GROUP LLC

(413) 327-7998

10 Lillybrook Rd, Pittsfield, MA 01201
/8
$45,000
- Land
- 1.08 Acres
- $41,666 per Acre
Lot 24 Old Farm Ln, Pittsfield, MA 01201

This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas.Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and numerous

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

(413) 343-7322

Lot 24 Old Farm Ln, Pittsfield, MA 01201
/8
$55,000
- Land
- 1 Acre
- $55,000 per Acre
Lot 23 Old Farm Ln, Pittsfield, MA 01201

This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas.Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and numerous

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

(413) 307-3151

Lot 23 Old Farm Ln, Pittsfield, MA 01201
/46
$699,900
- 5 Beds
- 3.5 Baths
- 3,074 Sq Ft
161 Leona Dr, Pittsfield, MA 01201

Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an

Nick Geranios

WILLIAM PITT SOTHEBY'S - LENOX

(413) 570-8931

161 Leona Dr, Pittsfield, MA 01201
/7
$59,900
- Land
- 1.23 Acres
- $48,699 per Acre
Lot 140 Westbrook Terrace, Pittsfield, MA 01201

Nestled on a quiet street among upscale homes, this 1.23-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and lasting value of this

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 288-3713

Lot 140 Westbrook Terrace, Pittsfield, MA 01201
/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
/55
$325,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
8 Samson Ave, Pittsfield, MA 01201

Lovely 3-Bedroom Ranch with Scenic Views and Endless Potential. Nestled on just over half an acre, this delightful ranch offers peaceful surroundings and picturesque views. Perfect for those seeking tranquility with room to grow. Step into the inviting living room, where a graceful bow window fills the space with natural light, complemented by a cozy fireplace and newer laminate flooring.The

Mary Smith

WILLIAM PITT SOTHEBY'S - LENOX

(413) 767-4399

8 Samson Ave, Pittsfield, MA 01201
/43
$445,000
- 2 Beds
- 3 Baths
- 1,814 Sq Ft
35 Chapman Rd, Pittsfield, MA 01201

Classic New England farmhouse featuring a charming kitchen with beautiful Berkshire views and an open, inviting layout perfect for entertaining. The 1st floor offers, full bath and convenient laundry hookups, along with 2 living rooms. One ideal for relaxation and the other a perfect home office, playroom, game room. Upstairs, you'll find 2 good sized bedrooms each with their own full bathroom

Laura Arseneau

PAULA MCLEAN REALTORS INC.

(413) 323-3512

35 Chapman Rd, Pittsfield, MA 01201
/2
$320,000
- 6 Beds
- 4 Baths
- 3,912 Sq Ft
40 Henry Ave, Pittsfield, MA 01201

THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 27-31 Pleasant St. Pittsfield, MA 01201 and 101-103 Lincoln St. Pittsfield, MA 01201. Acquire three multifamily package offered at $920,000. Income & expense and rent roll document available in documents and or upon request.

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 822-2695

40 Henry Ave, Pittsfield, MA 01201
/7
$59,900
- Land
- 1.08 Acres
- $55,463 per Acre
Lot 144 Eastbrook Ln, Pittsfield, MA 01201

Nestled on a quiet street among upscale homes, this 1.08-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and lasting value of this

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 414-5864

Lot 144 Eastbrook Ln, Pittsfield, MA 01201
/91
$999,000 Open House 3/14
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
8 Northbrook Ln, Pittsfield, MA 01201

BE THE FIRST TO LIVE IN THIS HOME!!! This thoughtfully designed contemporary home offers quality construction, energy efficiency, and a rare opportunity for customization--without the lengthy build process. Built with comfort and performance in mind, the home features spray-foam insulation in the walls and attic, fiberglass insulation between floors, energy-efficient windows, and Central Air/Heat

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 591-5199

8 Northbrook Ln, Pittsfield, MA 01201
/69
$525,900
- 6 Beds
- 3 Baths
- 4,034 Sq Ft
144 Brombach St, Pittsfield, MA 01201

Beautiful, spacious 6 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated

Darcy Reid MOCKINGBIRD REAL ESTATE

144 Brombach St, Pittsfield, MA 01201
/47
$250,000
- 4 Beds
- 1 Bath
- 1,740 Sq Ft
9 Lincoln St, Pittsfield, MA 01201

Welcome to 9 Lincoln Street, featuring white interior, hardwood floors throughout, large sun-filled rooms, and an open, flowing layout. The main level features a spacious living room, a bonus room that could serve as a first-floor bedroom, a dining room, and kitchen with direct access to a fully fenced backyard. Double doors open to an outdoor space ideal for relaxing or entertaining. Upstairs

Jessica Rizzo LAMACCHIA REALTY, INC

9 Lincoln St, Pittsfield, MA 01201
/25
$255,000
- 2 Beds
- 1 Bath
- 1,227 Sq Ft
58 Churchill Crest, Pittsfield, MA 01201

2 bedroom end unit condo offering the rare ease of true one level living, tucked in Churchill Crest's most private and peaceful building. This special home feels like a quiet Berkshire sanctuary, with a thoughtful layout that flows comfortably and welcomes you the moment you arrive. It's ready for your vision, character allows you to shape the space to your own style. Outside, enjoy a sparkling

Keyla Girard LAMACCHIA REALTY, INC

58 Churchill Crest, Pittsfield, MA 01201
/73
$889,900
- 5 Beds
- 3.5 Baths
- 3,370 Sq Ft
5 Crofut St, Pittsfield, MA 01201

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

5 Crofut St, Pittsfield, MA 01201
/38
$349,000
- 3 Beds
- 2 Baths
- 1,538 Sq Ft
74 Norman Ave, Pittsfield, MA 01201

*Virtual tour with floor plans availableThis unique home sits on a large lot with a fabulous yard. There is a driveway with carport and shed included. Upon entering the home you will find a convenient porch leading to the living room with wood-burning fireplace. The first floor also features a bedroom with a loft, as well as full bathroom with laundry, dining room and kitchen. There is a large

Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

74 Norman Ave, Pittsfield, MA 01201
/78
$975,000
- 3 Beds
- 3 Baths
- 2,662 Sq Ft
1020 Cascade St, Pittsfield, MA 01201

Your dream oasis awaits! Nestled on 19.2 private, bucolic acres, this meticulously maintained 3-4 bedroom/3 bath log home is being offered with numerous upgrades, all within the past 3 years. 1st floor features an open floor plan with hardwood floors, vaulted ceilings, an abundance of natural light, along with the convenience of a 1st floor laundry and full bath. 2nd floor is home to a generous

Amy Wood STEEPLEVIEW REALTY - N. ADAMS

1020 Cascade St, Pittsfield, MA 01201
/69
$730,000
- 5 Beds
- 4.5 Baths
- 3,381 Sq Ft
33 Alpine Trail, Pittsfield, MA 01201

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and

Cortney Dupont COHEN & WHITE ASSOCIATES

33 Alpine Trail, Pittsfield, MA 01201
/22
$89,000
- 2 Beds
- 2 Baths
- 910 Sq Ft
2 Lakewood Cir, Pittsfield, MA 01201

Spacious 2 Bedroom / 2 Bathroom manufactured home in Lake Onota Village. This home has been completely renovated including, a new furnace, new siding, new windows & doors, updated electrical, new flooring throughout, new kitchen, new bathrooms and all new insulated skirting. This home has it all with a large primary bedroom, primary bath, walk-in closet and a bright 3 season room. Schedule your

Timothy Johnson NOCHER REALTY

2 Lakewood Cir, Pittsfield, MA 01201
/37
$329,900
- 3 Beds
- 1.5 Baths
- 1,563 Sq Ft
1070 Holmes Rd, Pittsfield, MA 01201

Wonderful home located at the southern end of Holmes Rd. Moments away from Tanglewood and other cultural attractions of the Berkshires. Close to skiing at Bousquet, shopping and restaurants. This ranch style home features a large living room with a fireplace. Formal dining room leads into the kitchen. Three good sized bedrooms, a full bath and half bath all on one level. The kitchen opens out to

Derek Strzepa NOCHER REALTY

1070 Holmes Rd, Pittsfield, MA 01201
/22
$349,900
- 3 Beds
- 2.5 Baths
- 1,824 Sq Ft
127 Oak Hill Rd, Pittsfield, MA 01201

Welcome Home! This inviting 3BR, 2.5BA raised ranch in Pittsfield offers an open, sun filled layout perfect for both everyday living and entertaining. The finished walk-out basement offers additional living space,ideal for a family room, home office and guest area. Outside, you will enjoy a automatic awning covered deck, a large yard with fire pit, perfect for gardening or hosting summer

Stacy Hebb NOCHER REALTY

127 Oak Hill Rd, Pittsfield, MA 01201
/7
$435,000
- Land
- 15 Acres
- $29,000 per Acre
0 Churchill St Unit 248259, Pittsfield, MA 01201

Discover the ideal setting for your next home or retreat on this 15-acre parcel in West Pittsfield. Thoughtfully prepared, the property already features installed electricity, along with a newly constructed driveway and building pad. Enjoy a perfect blend of open and wooded land, including 5+ acres of fields, 10 acres of forest, and approximately 700 feet of road frontage.With city water,

Sally Carr KEY REALTY

0 Churchill St Unit 248259, Pittsfield, MA 01201

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