Tony Segalla

Great Barrington MA

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

112 Closed Sales

$64M Total Value

$175K - $1.9M Price Range

$571.3K Average Price

Prior 5 years

About Tony

When Antonio Segalla bought his first house, I was terrified and overwhelmed. He didn’t know a thing about banking, inspections, Title 5, and so on. Now, teaching buyers and sellers how to move through the process with ease gives him joy and satisfaction.

Tony is a local Berkshire boy—raised in Canaan, CT and Great Barrington, MA. he worked in the family business, Segalla Sand and Gravel. Learning about developing land, driveways, septic systems and the like was great preparation for his real estate career.

He also did a stint in carpentry, so he knows what’s behind the walls. He can see properties both for what they are and what they can be. Tony helps his buyers and sellers anticipate problems before inspection, so they can take care of issues before they derail a deal.

Working in the hospitality industry for years (many know him from The Old Mill) has given him the ability to converse with anybody about anything, and diffuse tense situations.

Home Types: Lot/Land, House, Condo, Commercial, Manufactured, Townhouse

Years of Experience: 10

Education: Associate's Degree: Business Administration -Berkshire Community College

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	15
Total Value	$9,965,500
Average Sale Price	$664,367
Price Range	$35K - $1.5M

Buyer Deals
Total Deals	3
Total Value	$865,100
Average Sale Price	$288,367
Price Range	$99K - $396K

Seller Deals
Total Deals	25
Total Value	$14,552,388
Average Sale Price	$582,096
Price Range	$19K - $1.5M

Buyer Deals
Total Deals	7
Total Value	$2,813,000
Average Sale Price	$401,857
Price Range	$99K - $774K

Seller Deals
Total Deals	81
Total Value	$45,694,083
Average Sale Price	$564,124
Price Range	$19K - $1.9M

Buyer Deals
Total Deals	31
Total Value	$18,290,464
Average Sale Price	$590,015
Price Range	$50K - $1.4M

5 Year View

Tony's Active Listings

$575,000
- 7 Beds
- 6.5 Baths
- 3,684 Sq Ft
3 Lake Buel Rd

Great Barrington, MA
Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside,

Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$525,000
- 1 Bed
- 1 Bath
- 755 Sq Ft
8 Heberts Cove

Monterey, MA
Offering the rare and coveted 'lake life' on Lake Buel, this unique property presents an extraordinary opportunity to establish your own Berkshire footprint on an expansive 2-acre parcel. Comprising 90% sun-drenched, open meadow, the large lot serves as the ultimate blank canvas with potential for a stunning architectural expansion, a custom family compound, or agricultural designs. While the

Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$1,295,000
- 4 Beds
- 3.5 Baths
- 3,047 Sq Ft
3 Cornwall Dr

Great Barrington, MA
Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The

Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$450,000
- 3 Beds
- 1 Bath
- 1,025 Sq Ft
8 Stillwell St

Great Barrington, MA
Step into effortless Berkshire living in this design-forward mid-century ranch. Perfectly positioned on a quiet downtown dead-end road, this 3-bedroom, 1-bathroom home seamlessly blends crisp, modern style with classic architectural character. Inside, original hardwood floors guide you through a bright, fluid one-level layout. The living room serves as a comfortable anchor for cozy mountain

Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Recently Sold

$35,000

Sold Feb 25, 2026
- Land
- 6.91 Acre Lot
Lot 19-I W Center Rd

Otis, MA
- 29% Below List
- 158 Days On Market
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$175,000

Sold Feb 25, 2026
- Land
- 2.02 Acre Lot
229 Egremont Plain Rd

Egremont, MA
- 22% Below List
- 267 Days On Market
- Current Est. Value $183K
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$1,463,000

Sold Jan 9, 2026
- 3 Beds
- 2.5 Baths
- 2,153 Sq Ft
16 Heberts Cove

Great Barrington, MA
- 6% Above List
- $680/SF
- 6 Days On Market
- Current Est. Value $2M
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$400,000

Sold Dec 29, 2025
- 4 Beds
- 2 Baths
- 1,560 Sq Ft
127 Old Joe Rd

Great Barrington, MA
- 16% Below List
- $256/SF
- 99 Days On Market
- Current Est. Value $423K
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$290,000

Sold Dec 22, 2025
- Land
- 1.13 Acre Lot
1 Terra Ferma Dr

Egremont, MA
- 17% Below List
- 505 Days On Market
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$1,500,000

Sold Dec 18, 2025
- 3 Beds
- 2 Baths
- 2,990 Sq Ft
87 Alford Rd

Great Barrington, MA
- 33% Below List
- $502/SF
- 394 Days On Market
- Current Est. Value $2M
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$90,000

Sold Dec 3, 2025
- Land
- 0.56 Acre Lot
Lot 1 Park St

Great Barrington, MA
- 28% Below List
- 127 Days On Market
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$300,000

Sold Nov 7, 2025
- 3 Beds
- 2.5 Baths
- 1,536 Sq Ft
179 S Main St

Sheffield, MA
- 24% Below List
- $195/SF
- 395 Days On Market
- Current Est. Value $339K
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$524,500

Sold Oct 28, 2025
- 2 Beds
- 2 Baths
- 1,560 Sq Ft
30 Clifden Ct

Unit 5

Lenox, MA
- 2% Below List
- $336/SF
- 31 Days On Market
Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Agent License: Massachusetts 009539871 New Mexico 009539871

Tony Segalla

(413) 414-4856

Homes for Sale by City

Tony Segalla

About Tony

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Tony's Listings and Deals

Tony's Active Listings

Recently Sold