Pittsfield, MA Homes for Sale with Acreage

/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,

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Lot #26 Old Farm Ln, Pittsfield, MA 01201
Explore Pittsfield
/92
$655,000

$45K 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

10 Lillybrook Rd, Pittsfield, MA 01201
/9
$45,000
- Land
- 1.08 Acres
- $41,667 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

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Lot 24 Old Farm Ln, Pittsfield, MA 01201
/4
$54,900
- Land
- 2.42 Acres
- $22,686 per Acre
0 Old Orebed Rd, Pittsfield, MA 01201

Discover the perfect setting for your dream home or Berkshire getaway on this breathtaking 2.42-acre parcel nestled in one of the region's most desirable locations. Ideally situated just minutes from Jiminy Peak Mountain Resort and near Mount Greylock, this property offers the ideal balance of peaceful natural surroundings and year-round adventure.Enjoy nearby access to skiing, hiking, lakes,

Keytoria Jenkins

BISHOP WEST REAL ESTATE

0 Old Orebed Rd, Pittsfield, MA 01201
/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

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Lot 23 Old Farm Ln, 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

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

61 Tor Ct, 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

Lot 144 Eastbrook Ln, 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

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Lot 25 Old Farm Ln, Pittsfield, MA 01201
/52
$515,000
- 3 Beds
- 3.5 Baths
- 3,275 Sq Ft
53 Greenings Ave, Pittsfield, MA 01201

Set within one of Southeast Pittsfield's most desirable neighborhood settings, 53 Greenings offers an exceptional blend of privacy, space, and effortless everyday living. Set on a beautifully landscaped 1.07-acre double lot, this spacious ranch style residence feels wonderfully secluded while remaining connected to the conveniences and amenities of the surrounding community. Mature landscaping,

Nick Geranios

WILLIAM PITT SOTHEBY'S - LENOX

53 Greenings Ave, Pittsfield, MA 01201
/37
$830,000
- 12 Beds
- 12 Baths
- 18,000 Sq Ft
40 Pecks Rd, Pittsfield, MA 01201

Don’t be late for this redevelopment opportunity! 18,000 Sqft on 1.1 Acres. Structurally sound property offers a rare opportunity to transform a historic space into a vibrant new community. Preliminary estimates suggest the potential for 12 residential units, with ample room for parking and green space. Featuring solid brick construction. Expansive windows, high ceilings, and open floor plans,

Xavier Cruz Fathom Realty

40 Pecks Rd, 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
/11
$42,000
- Land
- 1.31 Acres
- $32,061 per Acre
39 Old Farm Ln, Pittsfield, MA 01201

This Ready to Build exceptional 1.31-acre cul-de-sac homesite in Woodmonte Estates is ready for your custom dream home, with town sewer, private well, underground electric & gas, cable availability, and paved roads already in place. Assessed at $74,000 and selling it for $42,000.Located in one of Pittsfield's premier luxury communities, the property offers a peaceful, private setting while

Judi Panzano HOUSATONIC REAL ESTATE

39 Old Farm Ln, Pittsfield, MA 01201
/8
$129,900

$9K PRICE DROP
- Land
- 5.68 Acres
- $22,870 per Acre
132 Cascade St, Pittsfield, MA 01201

Build your Berkshire dream on this 5.68-acre parcel ideally located on a paved road just moments from Pittsfield State Forest. Offering a beautiful blend of privacy and accessibility, this property provides the perfect setting for a year-round home or weekend retreat. Enjoy easy access to miles of trails, hiking, biking, and outdoor recreation, all while being just a short drive to downtown

Elisha Poirier STONE HOUSE PROPERTIES, LLC

132 Cascade St, Pittsfield, MA 01201
/61
$699,900
- 4 Beds
- 3 Baths
- 3,268 Sq Ft
10 Lori Ct, Pittsfield, MA 01201

Gracefully situated on a gentle sloping hillside street this distinctively designed multi-level home offers distant and seasonal Berkshire mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home and grounds, you can embrace the vast privacy, open land and natural beauty much like the famed author. Surrounded by artfully designed gardens, this architecturally refined

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

10 Lori Ct, Pittsfield, MA 01201
/66
$3,900,000
- 8 Beds
- 6.5 Baths
- 7,494 Sq Ft
140 Hancock Rd, Pittsfield, MA 01201

Set along the shores of beautiful Pontoosuc Lake, this extraordinary private estate captures the very best of Berkshire waterfront living. Enjoy sweeping lake and mountain views, a private dock, heated pool, outdoor kitchen and fire pits designed for unforgettable entertaining. Inside, open-concept living showcases the views, while a chef's kitchen with Wolf and Sub-Zero appliances anchors the

Katie Soules WILLIAM RAVEIS - BERKSHIRE

140 Hancock Rd, Pittsfield, MA 01201
/42
$429,900
- 3 Beds
- 1 Bath
- 1,998 Sq Ft
191 Fort Hill Ave, Pittsfield, MA 01201

Well-maintained & move-in ready with historic charm, exceptional acreage, and endless possibilities. Set on approximately 5.2 acres in West Pittsfield's scenic farm country, this 1820s home offers a rare opportunity to enjoy the space & privacy that's increasingly difficult to find at this price point. Inside, you'll find spacious rooms, beautiful hardwood floors, a wide central staircase,

THE KAHN TEAM BISHOP WEST REAL ESTATE

191 Fort Hill Ave, Pittsfield, MA 01201
/8
$380,000
- Land
- 15 Acres
- $25,333 per Acre
365 Churchill St, 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,

Sarah Carr Key Realty

365 Churchill St, Pittsfield, MA 01201
/12
$159,000
- Land
- 1.3 Acres
- $122,308 per Acre
636 Hancock Rd, Pittsfield, MA 01201

An excellent opportunity to build your dream home on over an acre of land with many of the major improvements already in place. This developed parcel is ready for its next owner, featuring power with meter and panel, city water connected with an on-site shutoff, and operable internet service. A milled blacktop driveway provides convenient access, and city-approved septic designs have already been

Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

636 Hancock Rd, Pittsfield, MA 01201
/10
$49,900

$10K PRICE DROP
- Land
- 3.1 Acres
- $16,097 per Acre
0 Eastbrook Ln, Pittsfield, MA 01201

**Build Your Dream Home in the Exclusive Woodmonte Community!**Welcome to this DOUBLE Lot # 148-9 Eastbrook Lane, located in the prestigious and private Woodmonte neighborhood in Pittsfield, MA. This secluded double lot, listed at $59,900, is a rare find--completely prepped, fully serviced, and ideal for building your dream home!Enjoy the convenience of immediate ''Plug & Play'' construction,

Nathan Girard ROYAL PROPERTY GROUP

0 Eastbrook Ln, Pittsfield, MA 01201
/54
$799,000
- 4 Beds
- 3.5 Baths
- 3,325 Sq Ft
576 Holmes Rd, Pittsfield, MA 01201

Beautifully updated and maintained four bedroom, three and a half bath colonial. Spacious common areas washed with natural light make this home special. The main level boasts a large eat in kitchen, dining room, expansive living room with wood floors, family room with built ins and fireplace, separate laundry room, half bath, two car oversized garage and beautiful screened porch overlooking the

Cortney Dupont COHEN & WHITE ASSOCIATES

576 Holmes Rd, Pittsfield, MA 01201
/86
$690,000
- 4 Beds
- 2 Baths
- 2,104 Sq Ft
39 Cascade St, Pittsfield, MA 01201

Beautiful early 1900's colonial farm house with deeded agricultural and horticultural rights offering 2,104 sq ft of classic charm on a picturesque 2.3-acre lot. Spacious 4-bedroom, 2-full-bath home is close to the state forest with access to mountain biking and hiking trails. Main level includes a bright living room, formal dining room, and a generous kitchen with great storage. High ceilings,

Andrew Manns Lamacchia Realty, Inc. - Dalton

39 Cascade St, Pittsfield, MA 01201
/52
$799,000

$26K PRICE DROP
- 4 Beds
- 2.5 Baths
- 3,400 Sq Ft
26 Westbrook Terrace, Pittsfield, MA 01201

Set on 3.04 acres across two lots abutting protected land, this Executive Ranch is the only single-level home in the gated community of Woodmont Estates. 3,400 sq ft of expansive, easy living, featuring 4bd/2.5ba, a renovated primary bath, updated kitchen, and light-filled four-season sunroom w/ new Andersen windows. Designed for comfort & flexibility, the layout includes a private office, as

THE KAHN TEAM BISHOP WEST REAL ESTATE

26 Westbrook Terrace, Pittsfield, MA 01201
/24
$319,900
- 3 Beds
- 2 Baths
- 1,259 Sq Ft
79 Clark Rd, Pittsfield, MA 01201

Welcome home to this charming ranch offering effortless single-level living in a quiet, private, yet convenient neighborhood! Lovingly built, maintained, and cherished by the same family for decades, this home offers the perfect blend of comfort, flexibility, and functionality. The living room has a beautiful bay window, 3 bedrooms with abundant closet space and a full bath. The kitchen opens to

Nancy Bush Brooks SIGNATURE ASSOCIATES

79 Clark Rd, Pittsfield, MA 01201
/6
$40,000
- Land
- 1.06 Acres
- $37,736 per Acre
Lot 42 Old Farm Ln, Pittsfield, MA 01201

This is the lot you've been looking for! Over one acre in the wonderful Woodmonte Estates community. Located in West Pittsfield, you'll have easy access to all of the natural and cultural activities that the Berkshires has to offer. Get started on your dream home today!

Josh Conant COHEN & WHITE ASSOCIATES

Lot 42 Old Farm Ln, Pittsfield, MA 01201
/2
$29,900
- Land
- 2.14 Acres
- $13,972 per Acre
0 Old Orebed Rd, Pittsfield, MA 01201

Situated in a highly sought-after area of the region, this 2.14-acre lot provides an idyllic backdrop for building your forever residence or a seasonal Berkshire retreat. The property seamlessly blends outdoor recreation with tranquil nature, thanks to its prime location, a short drive from Jiminy Peak Mountain Resort and Mount Greylock. Endless year-round entertainment is at your fingertips

Roseanne Casale DePalma BHHS Realty Professionals NON-MEMBER / RECIPROCAL

0 Old Orebed Rd, Pittsfield, MA 01201
/2
$299,900
- Land
- 6 Acres
- $49,983 per Acre
0 West St, Pittsfield, MA 01201

This land is ideally located near downtown. 6 acres in a R6 zone, this has been approved for subdivision in the past. Comes with complete engineering including maps, topo's, traffic study, and much more. Beautiful views of Bousquet, bus line, all public utilities available. A RARE development opportunity to change the housing market in Pittsfield.

Steve Ray 413 REAL ESTATE

0 West St, Pittsfield, MA 01201
/2
$155,000
- Land
- 5 Acres
- $31,000 per Acre
365 Churchill St, Pittsfield, MA 01201

Seller is offering a 5-acre lot for separate sale from the 15-acre property. The 5-acre parcel does not include the installed electricity, driveway, or building pad, which are located on the 10-acre parcel.Also available with 15 acres MLS#248259

Sally Carr KEY REALTY

365 Churchill St, Pittsfield, MA 01201
/7
$219,900

$30K PRICE DROP
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
233 Cadwell Rd, Pittsfield, MA 01201

Two-family home set on just under 1.5 acres offering the perfect blend of country living and city convenience. Each unit features decks overlooking a spacious backyard, ideal for relaxing or entertaining. Enjoy the privacy and open space while still being just minutes from city amenities, shopping, and dining. A great opportunity for owner-occupants or investors--live in one unit and rent the

Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

233 Cadwell Rd, Pittsfield, MA 01201
/42
$1,750,000
- 6 Beds
- 4.5 Baths
- 7,894 Sq Ft
500 Williams St, Pittsfield, MA 01201

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal

Mauren White-Kirkby Berkshire Hathaway Home Services Barnbrook Realty

500 Williams St, Pittsfield, MA 01201
/69
$899,000

$90K PRICE DROP
- 5 Beds
- 5 Baths
- 3,823 Sq Ft
9 Eastbrook Ln, Pittsfield, MA 01201

Set within one of the Berkshires most coveted communities, 9 Eastbrook Lane is a masterclass in refined living, where thoughtful design meets impeccable care. Beautifully and intentionally sited, this distinguished residence offers 5 bedrooms, 3 full and 2 half baths across a gracious, light-filled layout designed for both elegant entertaining and everyday comfort. The stunning kitchen showcases

Victoria Standring Lamacchia Realty, Inc. - Dalton

9 Eastbrook Ln, Pittsfield, MA 01201
/9
$99,900

$10K PRICE DROP
- Land
- 2.34 Acres
- $42,692 per Acre
0 Pleasant St, Pittsfield, MA 01201

Attention developers! This is a great opportunity to own two adjacent buildable lots totaling 2.34 acres near downtown In Pittsfield, zoned RM (High Density Multifamily Residential).The lot with Parcel ID:I100002301 has 1.32 acres.The lot with Parcel ID:I100002026 has 1.02 acres.

Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

0 Pleasant St, Pittsfield, MA 01201
/6
$95,000
- Land
- 1.61 Acres
- $59,006 per Acre
497 Gale Ave, Pittsfield, MA 01201

Build Your Berkshire Dream Home: Views, Convenience, & Site Prep Complete! Immerse yourself in the tranquil beauty of the Berkshires. This exceptional property offers the perfect balance of a scenic country retreat and effortless proximity to urban convenience. Situated along a picturesque road, the gently graded, partially cleared acreage showcases sweeping mountain and pastoral views--the

Tammy Christen KELLER WILLIAMS REALTY

497 Gale Ave, Pittsfield, MA 01201
/67
$2,800,000
- 8 Beds
- 5.5 Baths
- 6,761 Sq Ft
497 Holmes Rd, Pittsfield, MA 01201

A Landmark Berkshire Estate of Extraordinary Provenance. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The

Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

497 Holmes Rd, Pittsfield, MA 01201
/7
$239,000
- Land
- 6.25 Acres
- $38,240 per Acre
549 Churchill St, Pittsfield, MA 01201

Ready to Build! Over 6 Acres of prime land with Views! Improvements include: Driveway, Well, and Septic plan. Bring your dream home plans and get started on this beautiful land on coveted Churchill Street. The House site is situated back from the road and elevated, giving you privacy and optimal views to the North and East. Around the corner from hiking and biking trails in Pittsfield State

Mark Rosengren WILLIAM RAVEIS - BERKSHIRE

549 Churchill St, Pittsfield, MA 01201
/19
$649,900
- Land
- 3.67 Acres
- $177,084 per Acre
37 Elm St, Pittsfield, MA 01201

Prime downtown opportunity! Almost 4 acres ready for your development ideas. One of Pittsfield's last remaining sites large enough for drive thru permit.Ther front of the property is BG, the back is CWS. Very versatile site on one of Pittsfield's finest streets.

Steve Ray 413 REAL ESTATE

37 Elm St, Pittsfield, MA 01201
/3
$898,000
- Land
- 12.84 Acres
- $69,938 per Acre
21 Dan Fox Dr, Pittsfield, MA 01201

12.84 Acres of Prime development Land. Ideal for possible Commercial and/or Residential projects. Close to Shopping and Transportation. Curb cut and some engineering done.

Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

21 Dan Fox Dr, Pittsfield, MA 01201
/73
$1,099,900

$350K PRICE DROP
- 5 Beds
- 5.5 Baths
- 6,121 Sq Ft
63 Blythewood Dr, Pittsfield, MA 01201

Live, Love, & Play in Blythewood Estates priced favorable $250,000 less than assessed value for a quick sale to allow you enjoyment this beautiful Berkshire season. A private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills while creating lasting memories. This stunning 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

63 Blythewood Dr, Pittsfield, MA 01201

Massachusetts Berkshire County

Home Prices in Pittsfield, MA

The median home sale price in Pittsfield, MA is $319,450, up 8% year-over-year. Homes in Pittsfield sell in 44 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $319,450	Median Single Family Sale Price $325,000
Median Townhouse Sale Price $269,000	Median 2 Bedroom Sale Price $260,000
Median 1 Bedroom Sale Price $175,000	Average Price Per Sq Ft $227
Number of Homes for Sale 105	Last 12 months Home Sales 496
Months of Supply 2.50	Median List Price $329,900
Median Change From 1st List Price 2%	Median Home Sale Price YoY Change 8%

How to Buy a Home How to Finance a Home How to Sell a Home

In Pittsfield, there are currently 38 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Pittsfield, MA offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Pittsfield and discover the potential and freedom that comes with owning your own piece of property.

Pittsfield Types of Homes for Sale

Pittsfield Homes by Price

Pittsfield Real Estate

More About Living in Pittsfield

Pittsfield Homes for Sale by Style

Homes for Sale in Nearby Cities

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage