Leslie Chesloff Real Estate Agent - WILLIAM PITT SOTHEBY'S - GT BARRINGTON

5 Deer Hill Rd, West Stockbridge, MA For Sale $4,975,000 - listed by Leslie Chesloff — For Sale $4,975,000

Leslie Chesloff listing and buyer's agent for 1 Pixley Hill Rd, Stockbridge, MA - sold for $595,000 — Sold $595,000

165 Kemble St Unit 18, Lenox, MA For Sale $4,150,000 - listed by Leslie Chesloff — For Sale $4,150,000

Leslie Chesloff buyer's agent for 0 Townhouse Hill Rd, Egremont, MA - sold for $225,000 — Sold $225,000

16 Old Tree Farm Rd, Stockbridge, MA For Sale $3,495,000 - listed by Leslie Chesloff — For Sale $3,495,000

Leslie Chesloff

Great Barrington MA

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

42 Closed Sales

$48.2M Total Value

$225K - $4.8M Price Range

$1.1M 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: Condo, House, Lot/Land, Mobile Homes

Years of Experience: 10

Education: University of Miami

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	7
Total Value	$6,357,083
Average Sale Price	$908,155
Price Range	$548K - $1.4M

Buyer Deals
Total Deals	6
Total Value	$5,237,500
Average Sale Price	$872,917
Price Range	$225K - $2M

Seller Deals
Total Deals	13
Total Value	$20,927,083
Average Sale Price	$1,609,776
Price Range	$548K - $4.8M

Buyer Deals
Total Deals	8
Total Value	$6,722,500
Average Sale Price	$840,313
Price Range	$225K - $2M

Seller Deals
Total Deals	25
Total Value	$35,073,583
Average Sale Price	$1,402,943
Price Range	$495K - $4.8M

Buyer Deals
Total Deals	17
Total Value	$13,145,500
Average Sale Price	$773,265
Price Range	$225K - $2M

5 Year View

Areas Leslie is Experienced In

Lenox

10 Sales
Great Barrington

10 Sales
Stockbridge

4 Sales
West Stockbridge

4 Sales
Sheffield

4 Sales
Egremont

3 Sales

Leslie's Listings and Deals

Leslie's Active Listings

$4,975,000
- 3 Beds
- 3.5 Baths
- 4,359 Sq Ft
5 Deer Hill Rd

West Stockbridge, MA
Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$4,150,000
- 3 Beds
- 3.5 Baths
- 3,348 Sq Ft
165 Kemble St

Unit 18

Lenox, MA
Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$3,495,000
- 5 Beds
- 4.5 Baths
- 3,862 Sq Ft
16 Old Tree Farm Rd

Stockbridge, MA
Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An

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

Recently Sold

$595,000

Sold Aug 12, 2026
- 3 Beds
- 2 Baths
- 1,582 Sq Ft
1 Pixley Hill Rd

Stockbridge, MA
- 14 Days On Market
- $376/SF
- Current Est. Value $604K
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$695,000

Sold Jun 18, 2026
- 4 Beds
- 2 Baths
- 2,715 Sq Ft
4 Fox Meadow Ln

Stockbridge, MA
- 16 Days On Market
- $256/SF
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$750,000

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

Egremont, MA
- 33 Days On Market
- $639/SF
- Current Est. Value $743K
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
- 17 Days On Market
- $454/SF
- 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
- 88 Days On Market
- $293/SF
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
- 146 Days On Market
- $480/SF
- 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
- 34 Days On Market
- $1,235/SF
- 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
- 12 Days On Market
- $302/SF
- Current Est. Value $783K
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
- 0 Days On Market
- $1,217/SF
- Current Est. Value $1M
Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Agent License: Massachusetts 9537915 New Mexico 9537915

Leslie Chesloff

(973) 318-1471

Nearby Homes

Leslie Chesloff

About Leslie

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Leslie is Experienced In

Leslie's Listings and Deals

Leslie's Active Listings

Recently Sold