Jessie Bennett

Responds Quickly

Great Barrington MA

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

60 Closed Sales

$35.7M Total Value

$272.5K - $1.9M Price Range

$604.6K Average Price

Prior five years

About Jessie

Jessie Bennett is a seasoned professional in the realm of real estate, serving clients across Berkshire County and Hudson Valley. Hailing from South Florida, her early years in studio dance instilled in her a resilience that has defined her career. Relocating to New York in 2009, Jessie embarked on a decade-long journey in the city's real estate market, honing her expertise and forging close relationships with property owners.

With eight years of experience as a rental and sales manager, Jessie transitioned seamlessly into residential sales in the Berkshires, where she excels in working directly with clients. Her approach is characterized by a commitment to education and inclusion, ensuring that her clients are active participants in the real estate process. In her dedication to making the real estate experience painless and pleasurable, Jessie embodies a bold and gritty spirit that sets her apart in the industry.

In the dynamic landscape where grit meets grace, Jessie Bennett stands as a beacon of professionalism, navigating the complexities of real estate with determination and a profound commitment to her client's success.

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

Years of Experience: 17

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$5,215,000

Average Sale Price

$745,000

Price Range

$320K - $1.6M

Buyer Deals

Total Deals

Total Value

$4,659,800

Average Sale Price

$931,960

Price Range

$610K - $1.1M

Seller Deals

Total Deals

Total Value

$8,848,000

Average Sale Price

$737,333

Price Range

$320K - $1.6M

Buyer Deals

Total Deals

Total Value

$7,567,800

Average Sale Price

$756,780

Price Range

$325K - $1.4M

Seller Deals

Total Deals

Total Value

$14,241,000

Average Sale Price

$593,375

Price Range

$273K - $1.6M

Buyer Deals

Total Deals

Total Value

$21,427,700

Average Sale Price

$612,220

Price Range

$130K - $1.9M

5 Year View

Neighborhoods Jessie is Experienced In

Great Barrington

11 Sales
Becket

7 Sales
Egremont

4 Sales
Stockbridge

4 Sales
Pittsfield

3 Sales
Kinderhook

3 Sales

Jessie's Active Listings

$439,000
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
13149 New York 22

Canaan, NY
Welcome to 13149 NY 22, Canaan, NY 12029—a beautifully updated 3-bedroom, 1.5-bath ranch set on two open, usable acres. This home has been thoughtfully refreshed from top to bottom, offering true ease of living in a peaceful countryside setting. Step inside to find gleaming wood floors throughout, freshly painted interiors, and renovated bathrooms with crisp, modern finishes. The efficient

Jessie Bennett William Pitt Sothebys Intn'l

$279,000
- Land
- 17 Acres
- $16,364 per Acre
13191 Route 22 Stop #80

Canaan, NY
17 private, secluded acres located on a quiet private road in Canaan, NY. The property features frontage on Flat Brook, multiple potential house sites with beautiful views, and mature woods throughout.Electric has already been pulled to the property, making it ready for building. The land is ideal for a primary residence, second home, or small retreat.Quiet, peaceful setting just minutes from

Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$429,000
- 4 Beds
- 2 Baths
- 1,800 Sq Ft
32 S Main Rd

Otis, MA
This recently renovated 1890 Colonial offers four bedrooms and two full bathrooms on 38 private acres in Otis. The home features a wood-burning fireplace, updated kitchen and bathrooms, and a first-floor bedroom addition with vaulted ceilings. It is connected to town sewer and has a private well. A detached garage and several outbuildings provide extra space for storage or projects. This home

Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Co-Listing Agent

$3,500,000
- 5 Beds
- 6.5 Baths
- 6,088 Sq Ft
110 Alford Rd

Great Barrington, MA
Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside,

Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Other Experience

First Time Home Buyers, Investments, Luxury Homes, Property Management

Agent License: New York #10401325185 Massachusetts #9570019

Jessie Bennett

(866) 977-6618

Responds Quickly

(866) 977-6618

Homes for Sale by City

Jessie Bennett

About Jessie

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Jessie is Experienced In

Jessie's Listings and Deals

Jessie's Active Listings

Other Experience