Homes for Sale near Hillcrest Educational Foundation

/15
$1,719,000
- 37 Beds
- 24 Baths
- 21,162 Sq Ft
306 South St, Pittsfield, MA 01201

Offered as a 7-property portfolio, totaling 21 units, this package includes a mix of multifamily properties and a single-family home with value-add potential. Several units are tenant-occupied, providing immediate income with upside potential, while others units require renovation, allowing investors to implement a phased improvement strategy. The portfolio currently generates an in-place NOI of

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 798-8328

306 South St, Pittsfield, MA 01201
/47
$650,000

$50K PRICE DROP
- 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

$20K PRICE DROP
- 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
/33
$1,349,000

$46K PRICE DROP
- 3 Beds
- 2 Baths
- 1,728 Sq Ft
61 Tor Ct, Pittsfield, MA 01201

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors

Allen Bassen

BERKSHIRE HOMES AND CONDOS

(413) 287-9929

61 Tor Ct, Pittsfield, MA 01201
/43
$425,000

$20K PRICE DROP
- 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
/4
$389,900
- 3 Beds
- 2 Baths
- 1,375 Sq Ft
0 Broadview Terrace, Pittsfield, MA 01201

To Be Built, energy-efficient, low-maintenance 1,375 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home offers true single-level living with an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. The primary suite includes a private full bath, while two additional bedrooms offer flexibility for guests or a home office.

Syrah Bradley

BISHOP WEST REAL ESTATE

(413) 307-3463

0 Broadview Terrace, Pittsfield, MA 01201
/7
$59,900

$20K PRICE DROP
- 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
/11
$814,900

$25K PRICE DROP
- 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
/4
$399,900
- 3 Beds
- 2 Baths
- 1,340 Sq Ft
Lot 4 Tanner St, Pittsfield, MA 01201

To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath,

Syrah Bradley

BISHOP WEST REAL ESTATE

(413) 863-6124

Lot 4 Tanner St, Pittsfield, MA 01201
/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
/2
$39,900
- Land
- 6,438 Sq Ft
- $269,966 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
$114,900

$25K PRICE DROP
- Land
- 3.59 Acres
- $32,006 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
/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.

(413) 393-2997

117 Lime Kiln Rd, Lenox, MA 01240
/4
$399,900
- 3 Beds
- 2 Baths
- 1,340 Sq Ft
Lot 5 Tanner St, Pittsfield, MA 01201

To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath,

Syrah Bradley

BISHOP WEST REAL ESTATE

(413) 384-3681

Lot 5 Tanner St, Pittsfield, MA 01201
/4
$399,900
- 3 Beds
- 2 Baths
- 1,340 Sq Ft
Lot 6 Tanner St, Pittsfield, MA 01201

To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath,

Syrah Bradley

BISHOP WEST REAL ESTATE

(413) 423-0846

Lot 6 Tanner St, Pittsfield, MA 01201
/7
$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
/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
$89,900

$20K PRICE DROP
- Land
- 2.14 Acres
- $42,010 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
$179,900

$75K PRICE DROP
- Land
- 8.93 Acres
- $20,146 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
/13
$145,000
- 2 Beds
- 1 Bath
- 2,386 Sq Ft
141 Dewey Ave, Pittsfield, MA 01201

Investor Opportunity. Property is being offered as-is and will require significant TLC throughout. Great opportunity for a contractor, rehab investor, or buyer looking for a project with potential in a convenient Pittsfield location.The property is in need of repairs and updates, and financing may be limited due to condition. Buyer responsible for all due diligence, inspections, and verification

John Ciepiela

BISHOP WEST REAL ESTATE

(413) 288-5568

141 Dewey Ave, Pittsfield, MA 01201
/11
$1,101,800

$75K PRICE DROP
- 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
/7
$789,900

$20K PRICE DROP
- 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
$675,000

$25K PRICE DROP
- 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
/9
$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
/91
$1,650,000
- 7 Beds
- 6.5 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

(413) 393-6344

20 E Dugway Rd, Lenox, MA 01240
/6
$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
/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. - Dalton

58 Churchill Crest, Pittsfield, MA 01201
/63
$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
/16
$159,000
- 1 Bed
- 1 Bath
- 617 Sq Ft
108 E Housatonic St Unit 7, Pittsfield, MA 01201

Great location in Southeast Pittsfield..Short walk to downtown Pittsfield.. Lovely unit with hardwood floors in the Living room and Bedroom......Nice sized balcony (facing the morning sun) to relax on..Coin operated laundry just a few steps down into the lower level.. Storage locker is available in an upstairs area through the door on the balcony. The unit sq footage is 617 and is recorded in the

Barbara K Greenfeld SIGNATURE ASSOCIATES

108 E Housatonic St Unit 7, Pittsfield, MA 01201
/57
$1,350,000

Open Sat 1PM - 2:30PM $325K PRICE DROP
- 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
/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
/8
$29,900
- Land
- 14,809 Sq Ft
- $87,944 per Acre
I110019004 Brown St, Pittsfield, MA 01201

Priced well below assessed value. Zoning verification states: The property is a .344-acre lot having 100 feet of frontage on Brown Street and 50 feet of frontage on Scammell Ave. There are no structures on the property. The lot meets the minimum dimensional requirements for development.

Laurie Atkinson KELLER WILLIAMS REALTY

I110019004 Brown St, Pittsfield, MA 01201
/50
$579,900

$20K PRICE DROP
- 4 Beds
- 3.5 Baths
- 3,561 Sq Ft
2 Amy Ct, Pittsfield, MA 01201

Stunning and beautifully designed three-level end unit condominium with luxury finishes throughout. Enter into an open-concept main level, highlighted by gleaming hardwood floors, recessed lighting, and expansive windows that flood the space with natural light. The kitchen offers stainless steel appliances, granite countertops, and custom cabinetry. The spacious living and dining areas are

Cory Evangelisto NOCHER REALTY

2 Amy Ct, Pittsfield, MA 01201
/5
$39,000
- Land
- 17,860 Sq Ft
- $95,120 per Acre
33 Circular Ave, Pittsfield, MA 01201

Building lot that is well located and cleared in downtown Pittsfield. City lot is 0.41 acres, approved for building Single Family or Multi-Family up to 4 units and fits within the Multi-Family Residential zone (R-M). Walk-able and close to all amenities including restaurants, grocery stores, shops and public transportation. Water, sewer and gas available on the street. Proximity to the region's

Cory Evangelisto NOCHER REALTY

33 Circular Ave, Pittsfield, MA 01201
/7
$380,000

$55K PRICE DROP
- Land
- 15 Acres
- $25,333 per Acre
0 Churchill St Unit 248259, Pittsfield, MA 01201

Price reduction. Motivated seller.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

Sally Carr KEY REALTY

0 Churchill St Unit 248259, Pittsfield, MA 01201
/14
$358,000

$10K 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
/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
/29
$299,000
- 4 Beds
- 2 Baths
- 1,627 Sq Ft
162 W Housatonic St, Pittsfield, MA 01201

Enjoy this charming 4-bedroom, 2-bathroom home offering a spacious and functional layout, tasteful updates, and excellent convenience. The property features an updated heating system, efficient natural gas utilities, a large open kitchen with new appliances, and updated flooring. Both bathrooms have been recently renovated with stylish new finishes and tilework. Enjoy the flexibility of a

Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

162 W Housatonic St, Pittsfield, MA 01201
/30
$595,000
- 2 Beds
- 2.5 Baths
- 1,680 Sq Ft
1136 Barker Rd Unit 27, Pittsfield, MA 01201

Charming Condominium at South Pond Farm. 2 bedrooms 2-1/2 baths, brand new kitchen. Panoramic views of Richmond Pond from the living room/dining room and bedrooms. The community offers tennis, heated gunite swimming pool, private beach, kayak, /canoe racks, water aerobics, organized book groups and active social environment.

Buddy Lewis BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

1136 Barker Rd Unit 27, Pittsfield, MA 01201
/65
$229,900

Open Thu 3PM - 4:30PM
- 5 Beds
- 2 Baths
- 3,048 Sq Ft
96 Brown St, Pittsfield, MA 01201

Discover a fantastic investment opportunity at 96-98 Brown Street, Pittsfield. This two-family home features a cozy 2-bedroom, 1-bath unit on the first floor, perfect for easy living, and a spacious 3-bedroom, 1-bath unit on the second floor, ideal for owner occupied or Investors alike. Recent upgrades include a new roof, some fresh paint, updated 100 amp electrical panels, new windows, and a

Doug Collins Lamacchia Realty, Inc. - Dalton

96 Brown St, Pittsfield, MA 01201

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