Jessie Bennett

Jessie Bennett

Licensed Real Estate Salesperson

Great Barrington

306 Main Street
Great Barrington, MA 01230

Chatham

2 Park Row
Suite 1
Chatham, NY 12037
  • Born In:
    Ft Lauderdale
  • Live In:
    FL, NY, MA
  • Passion:
    Real Estate

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. 

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. 

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. 

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  • Agent Designations
    • Waterfront Property Specialist
    • Ski Property Specialist
    • Farm and Ranch Specialist
    • Resort and Second Home Property Specialist
    • Seller Representative Specialist

Testimonials

Jessie was terrific.

Thomas Reap Lisa Horelick Reap

Jessie Bennett was a pleasure to work with in finding a home. She is competent, thorough and personally charming.

Daniel Cooper

I had the pleasure of working with Jessie Bennett to find our new home. She built a thorough and complete understanding of what my wife and I valued in a home, and directed our search, got us a fantastic price, and set us up with excellent support for inspections, financing, and contractor contacts as we make our new house into our home. She was incredibly generous with her time and had our back over a trying closing with a hostile counterparty, and overall made the whole process run smoothly, consistently herself ahead of the game and keeping me ahead of the game as well. Overall, I've come away with a home I am excited about, the resources and knowledge to settle in, the connections for reliable support, broad knowledge of the area I am moving into, a feeling like I was able to make a positive and educated decision on a new home, all with minimum stress on our part. Thanks Jessie!

Jared Karlow

jessie bennett is a dream to work with. she is highly professional, diligent and has a warm & lovely personality.

Jennifer Dorfman

Jessie was spectacular. Unprecedented problem-solving skills. Great empathy. Incredible patience and sticktuitivness. She has invaluable connections and is helpful with ever step of the process. She is trustworthy and has a perfect demeanor for this role. I’d very highly recommend her to anyone in heed of an agent.

Michael Foilb Cheryl Foilb

Jessie went above and beyond to make our out of state real estate sale as easy as possible. She was always immediately responsive and I would recommend her to anyone selling their home.

Pam Starr

Our realtor Jessie was outstanding and really went above and beyond to make the sale of our townhome as easy as possible. She had recommendations for everyone that we needed to contract to complete our move-- we couldn't be more grateful!

Ellen L. Brown Living Trust Pam Starr & Greer Goldstein

My Listings

32 S Main Rd $499,000 link

32 S Main Rd

Otis, MA 01253
$499,000
4 Beds 2 Baths 1,800 Sqft 38.5 Acres

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,...

4
bed
2
bath
1,800
sqft
13191 Route 22 Stop #80 $249,000 link

13191 Route 22 Stop #80

Canaan, NY 12029 | Columbia County
$249,000
17.05 Acres

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...

17.05
acre
110 Alford Rd $3,500,000 link

110 Alford Rd

Great Barrington, MA 01230 | Berkshire County
$3,500,000
5 Beds 6/1 Baths 6,088 Sqft 12.23 Acres

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...

5
bed
6/1
bath
6,088
sqft

My Sales

174 Long Mountain Rd $1,850,000 link

174 Long Mountain Rd

Otis, MA 01253 | Berkshire County
$1,850,000
4 Beds 3 Baths 2,400 Sqft 7.9 Acres

Introducing a picturesque retreat nestled on the shores of Hayes Pond in beautiful Otis. This exceptional home sits on 7.9 acres and boasts an array of enticing features that offer...

4
bed
3
bath
2,400
sqft
74 Oak Ridge $1,635,000 link

74 Oak Ridge

Canaan, NY 12029 | Columbia County
$1,635,000
4 Beds 3/1 Baths 4,604 Sqft 5.18 Acres

Just over two hours from both New York City and Boston, this architecturally refined 4-bedroom contemporary sits on 5 private acres along a quiet country road in Columbia County....

4
bed
3/1
bath
4,604
sqft
82 E Main St $1,350,000 link

82 E Main St

Stockbridge, MA 01262 | Berkshire County
$1,350,000
5 Beds 4 Baths 3,891 Sqft 2 Acres

Discover a historically significant gem in Stockbridge, nestled on 2 lush acres with Housatonic River frontage. The property, originally landscaped by renowned sculptor Daniel...

5
bed
4
bath
3,891
sqft
0 Tyringham Rd $1,300,000 link

0 Tyringham Rd

Otis, MA 01253 | Berkshire County
$1,300,000
205.3 Acres

Escape to the tranquility of nature with this extraordinary 205 acre property nestled in the picturesque Tyringham valley in Massachusetts. The land has a blend of wooded terrain,...

205.30
acre
403 N Maple Lane $1,099,900 link

403 N Maple Lane

Valatie, NY 12184 | Columbia County
$1,099,900
4 Beds 2/1 Baths 3,224 Sqft 31.6 Acres

Welcome to Hickory Bend Farm at 403 Maple Lane North, where the spirit of days gone by is still alive in every pastel-painted sunset sky . Built in 1824, this post and beam Colonial...

4
bed
2/1
bath
3,224
sqft
54 Mercer Mountain Road $1,050,000 link

54 Mercer Mountain Road

East Chatham, NY 12060 | Columbia County
$1,050,000
4 Beds 2 Baths 2,520 Sqft 11.81 Acres

On a clear day, you can see forever and ever... VIEWS, VIEWS, VIEWS, for endless miles.to The.Catskills, and the Towers in Albany. From sunrise to sunset, you will be mesmerized...

4
bed
2
bath
2,520
sqft
6 Wheatley Dr $933,000 link

6 Wheatley Dr

Stockbridge, MA 01262 | Berkshire County
$933,000
3 Beds 2/1 Baths 2,851 Sqft 2.6 Acres

Sheila Thunfors sthunfor@bcn.net 413-232-0234 STONE HOUSE PROPERTIES, LLC

3
bed
2/1
bath
2,851
sqft
0 Mansfield Road $870,000 link

0 Mansfield Road

Hillsdale, NY 12529 | Columbia County
$870,000
1,010,592 Sqft 23.2 Acres

Alpine Views.Transport yourself to a magical hilltop in Switzerland, where mountain meadows flow and rolling hills command the view. Look out to the Catskills, over high fields...

1,010,592
sqft
7 Fern Hill Rd $850,000 link

7 Fern Hill Rd

Great Barrington, MA 01230 | Berkshire County
$850,000
5 Beds 3/1 Baths 4,000 Sqft 3.06 Acres

Welcome to the picturesque town of Great Barrington, Massachusetts, where an extraordinary diamond in the rough opportunity awaits you down a long private driveway at the end of...

5
bed
3/1
bath
4,000
sqft
34 Seekonk Cross Rd $800,000 link

34 Seekonk Cross Rd

Great Barrington, MA 01230 | Berkshire County
$800,000
4 Beds 3 Baths 3,177 Sqft 2.03 Acres

WELL MAINTAINED FARM HOUSE WITH THE BONUS OF A SEPARATE APARTMENT! Ideal for friends, family or to benefit from rental income. The backyard is an oasis to find peace after a busy...

4
bed
3
bath
3,177
sqft
2 Lake Dr $800,000 link

2 Lake Dr

Stockbridge, MA 01262 | Berkshire County
$800,000
4 Beds 4 Baths 2,500 Sqft 1.46 Acres

FABULOUS STOCKBRIDGE LOCATION: MID CENTURY Light and bright Contemporary with open plan, large great room with cathedral ceiling and cast iron free standing fireplace, updated...

4
bed
4
bath
2,500
sqft