Leslie Chesloff

Great Barrington MA

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

45 Closed Sales

$52.2M Total Value

$275K - $4.8M Price Range

$1.2M Average Price

Prior 5 years

About Leslie

After a successful 35-year career as a television executive, Leslie relocated to Great Barrington full-time seven years ago and became a licensed real estate agent. She has quickly become one of the top producing agents in Berkshire County. Having gone through the construction process many times, Leslie has recently built her second home in the Berkshires. Leslie has also built three homes in Boston, Philadelphia and Short Hills NJ, she loves to help clients with interior design and the building process, as well as give recommendations for everything from the best painter to the best restaurant.

Leslie is happy to show you around the Berkshires and share all of her favorite things.

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

Years of Experience: 10

Education: University of Miami

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	8
Total Value	$11,062,083
Average Sale Price	$1,382,760
Price Range	$548K - $3.9M

Buyer Deals
Total Deals	5
Total Value	$5,012,500
Average Sale Price	$1,002,500
Price Range	$680K - $2M

Seller Deals
Total Deals	11
Total Value	$19,637,083
Average Sale Price	$1,785,189
Price Range	$548K - $4.8M

Buyer Deals
Total Deals	7
Total Value	$6,497,500
Average Sale Price	$928,214
Price Range	$515K - $2M

Seller Deals
Total Deals	26
Total Value	$36,810,283
Average Sale Price	$1,415,780
Price Range	$495K - $4.8M

Buyer Deals
Total Deals	19
Total Value	$15,406,500
Average Sale Price	$810,868
Price Range	$275K - $2M

5 Year View

Neighborhoods Leslie is Experienced In

Lenox

13 Sales
Great Barrington

9 Sales
Sheffield

5 Sales
Alford

3 Sales
Egremont

2 Sales
West Stockbridge

2 Sales

Leslie's Active Listings

$3,750,000
- 5 Beds
- 7 Baths
- 6,022 Sq Ft
2650 Swamp Rd

Richmond, MA
April Hill, an exquisite 1850 Greek Revival masterpiece. This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$2,950,000
- 7 Beds
- 7 Baths
- 6,232 Sq Ft
802 State Rd

Richmond, MA
Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. The legendary c. 1776 estate boasts a well maintained main residence/Inn, three cottages and a great barn for entertaining. The residence/Inn features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. Its dignified presence is complemented by a dining room, entrance parlor,

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$695,000
- 4 Beds
- 2 Baths
- 2,715 Sq Ft
4 Fox Meadow Ln

Stockbridge, MA
Convenient one-level ranch in a prime location close to town. This well-maintained home offers four bedrooms and two full bathrooms, ideal for comfortable living. The updated kitchen features modern finishes and plenty of workspace. Enjoy energy efficiency with owned solar panels that significantly reduce utility costs, plus a pellet stove for supplemental heating. A generator ensures

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Recently Sold

$750,000

Sold Jun 3, 2026
- 2 Beds
- 2 Baths
- 1,173 Sq Ft
76 Prospect Lake Rd

Egremont, MA
- $639/SF
- 33 Days On Market
- Current Est. Value $749K
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$1,199,082

Sold Apr 2, 2026
- 4 Beds
- 3.5 Baths
- 2,640 Sq Ft
12 Alford Center Rd

Great Barrington, MA
- $454/SF
- 17 Days On Market
- Current Est. Value $1M
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$548,000

Sold Dec 18, 2025
- 2 Beds
- 4 Baths
- 1,870 Sq Ft
19 Hawthorne Rd

Unit 3B Stables

Stockbridge, MA
- 16% Below List
- $293/SF
- 88 Days On Market
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$1,200,000

Sold Oct 31, 2025
- 3 Beds
- 2.5 Baths
- 2,500 Sq Ft
247 Peter Menaker Rd

Great Barrington, MA
- 14% Below List
- $480/SF
- 146 Days On Market
- Current Est. Value $1M
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$1,370,000

Sold Jul 15, 2025
- 1 Bed
- 1.5 Baths
- 1,109 Sq Ft
165 Kemble St

Unit 2

Lenox, MA
- 2% Below List
- $1,235/SF
- 34 Days On Market
- Current Est. Value $1M
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$795,000

Sold Jun 9, 2025
- 3 Beds
- 2.5 Baths
- 2,633 Sq Ft
371 Berkshire School Rd

Sheffield, MA
- $302/SF
- 12 Days On Market
- Current Est. Value $811K
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$1,350,000

Sold May 15, 2025
- 1 Bed
- 1.5 Baths
- 1,109 Sq Ft
165 Kemble St

Unit 3

Lenox, MA
- $1,217/SF
- 0 Days On Market
- Current Est. Value $1M
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$3,850,000

Sold May 15, 2025
- 3 Beds
- 3.5 Baths
- 3,348 Sq Ft
165 Kemble St

Unit 18

Lenox, MA
- 10% Below List
- $1,150/SF
- 39 Days On Market
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$2,300,000

Sold Feb 3, 2025
- 2 Beds
- 2.5 Baths
- 1,790 Sq Ft
165 Kemble St

Unit 10

Lenox, MA
- $1,285/SF
- 10 Days On Market
- Current Est. Value $2M
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Agent License: New Mexico 9537915

Leslie Chesloff

(973) 318-1471

Homes for Sale by City

Leslie Chesloff

About Leslie

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Leslie is Experienced In

Leslie's Listings and Deals

Leslie's Active Listings

Recently Sold