Jennifer Capala

Jennifer Capala

Licensed Associate Real Estate Broker

Great Barrington

306 Main Street
Great Barrington, MA 01230

Lenox

26 Church Street
Lenox, MA 01240
  • Born In:
    Cambridge, MA
  • Live In:
    Spencertown, NY
  • Favorite Movie:
    Shawshank Redemption
  • Passion:
    Nature, Design, Bahkti Yoga, Dogs
  • Interests:
    Skiing, traveling, music, Traveling, Cooking, Skiing, Biking
  • Favorite Lyric:
    Everything's gonna be alright
  • Can’t Live Without:
    Nature's beauty
  • Inspiration:
    Friends and family

Jennifer's unwavering commitment to superior professional standards, along with a keen ability to work through challenges with creativity and care has allowed her to build a highly successful real estate career.  After more than 15 years of experience  Jennifer's clients refer to her as: enthusiastic, knowledgeable, responsive, ethical, and extremely helpful.

With a smile, she admits to being obsessed with real estate. This passion for real estate began over 20 years ago when she purchased and renovated a Brooklyn firehouse which turned out to be the gift that just keeps giving.  New York magazine and The NY Times published stories about the circa-1900,  former firehouse in Williamsburg which was transformed from a wreck into a livable, multi-use space. "A wise real estate investment can really transform your life."

Jennifer came to real estate after a successful career as a commercial photographer documenting architecture and interiors for top designers in New York City.  Her exposure  to a wide range of architecture, along with a keen eye for design and construction, has given her the ability to assess the true potential of almost any property.   


When not hard at work, she greatly enjoys down time with her family and friends, exploring this stunning region, taking long walks with Harvey the dog, skiing at Catamount, and teaching Yoga at her favorite studio in Chatham, NY.  

Jennifer's unwavering commitment to superior professional standards, along with a keen ability to work through challenges with creativity and care has allowed her to build a highly successful real estate career.  After more than 15 years of experience  Jennifer's clients refer to her as: enthusiastic, knowledgeable, responsive, ethical, and extremely helpful.

With a smile, she admits to being obsessed with real estate. This passion for real estate began over 20 years ago when she purchased and renovated a Brooklyn firehouse which turned out to be the gift that just keeps giving.  New York magazine and The NY Times published stories about the circa-1900,  former firehouse in Williamsburg which was transformed from a wreck into a livable, multi-use space. "A wise real estate investment can really transform your life."

Jennifer came to real estate after a successful career as a commercial photographer documenting architecture and interiors for top designers in New York City.  Her exposure  to a wide range of architecture, along with a keen eye for design and construction, has given her the ability to assess the true potential of almost any property.   


When not hard at work, she greatly enjoys down time with her family and friends, exploring this stunning region, taking long walks with Harvey the dog, skiing at Catamount, and teaching Yoga at her favorite studio in Chatham, NY.  

Jennifer's unwavering commitment to superior professional standards, along with a keen ability to work through challenges with creativity and care has allowed her to build a highly successful real estate career.  After more than 15 years of experience  Jennifer's clients refer to her as: enthusiastic, knowledgeable, responsive, ethical, and extremely helpful.

With a smile, she admits to being obsessed with real estate. This passion for real estate began over 20 years ago when she purchased and renovated a Brooklyn firehouse which turned out to be the gift that just keeps giving.  New York magazine and The NY Times published stories about the circa-1900,  former firehouse in Williamsburg which was transformed from a wreck into a livable, multi-use space. "A wise real estate investment can really transform your life."

Jennifer came to real estate after a successful career as a commercial photographer documenting architecture and interiors for top designers in New York City.  Her exposure  to a wide range of architecture, along with a keen eye for design and construction, has given her the ability to assess the true potential of almost any property.   


When not hard at work, she greatly enjoys down time with her family and friends, exploring this stunning region, taking long walks with Harvey the dog, skiing at Catamount, and teaching Yoga at her favorite studio in Chatham, NY.  

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  • Agent Designations
    • Broker
  • Awards
    • Sotheby's Gold Award 2023
    • Sotheby's Gold Award 2022
    • Sotheby's Diamond Award 2021
    • Sotheby's Platinum Award 2020
  • Specialities
    • Photography
    • Staging
    • Negotiating
    • Supporting buyers and sellers

My Listings

4317 Ny-23 $5,900,000 link

4317 Ny-23

Hudson, NY 12534 | Columbia County
$5,900,000
7 Beds 7/1 Baths 7,165 Sqft 100.51 Acres

 Mountain views, historic charm, hiking trails and 100 private acres, just minutes to everything Hudson....what's not to love. Say hello to your new Hudson Valley home....

7
bed
7/1
bath
7,165
sqft
322 Arcadia Drive $600,000 link

322 Arcadia Drive

Ancram, NY 12502 | Columbia County
$600,000
3 Beds 3/1 Baths 2,442 Sqft 0.06 Acres

Waterfront living at its finest at desirable Long Lake. The main reason owners love Long Lake is because it is truly the only waterfront community in Columbia County which offers...

3
bed
3/1
bath
2,442
sqft
943 State Route 299 $4,125,000 link

943 State Route 299

Gardiner, NY 12525 | Ulster County
$4,125,000
4 Beds 3/1 Baths 4,234 Sqft 5.05 Acres

 Envision living in a home that is not just a residence but a testament to the awe-inspiring forces of nature that shaped the Hudson River Valley. Introducing Kushner Studio's...

4
bed
3/1
bath
4,234
sqft

My Sales

1175 County Route 27a $5,600,000 link

1175 County Route 27a

Copake, NY 12516 | Columbia County
$5,600,000
6 Beds 7 Baths 8,384 Sqft 133.04 Acres

Nestled in the heart of the Hudson Valley, this unparalleled 133 acre compound in Copake, NY is a masterpiece of luxury and sophistication. The sprawling private grounds are...

6
bed
7
bath
8,384
sqft
51 Hall Hill Rd $3,400,000 link

51 Hall Hill Rd

Ancram, NY 12502
$3,400,000
3 Beds 1 Baths 2,380 Sqft 546.59 Acres

Make these 500+ acres of prized Columbia County farmland the beginning of your next chapter. The possibilities are many given that the land is unencumbered by agricultural or conservation...

3
bed
1
bath
2,380
sqft
638 Pitt Hall Rd $2,300,000 link

638 Pitt Hall Rd

Old Chatham, NY 12136 | Columbia County
$2,300,000
5 Beds 3/1 Baths 3,690 Sqft 168 Acres

A setting surrounded by classic Columbia County views of rolling hills and bucolic farmland, smack in the middle of Old Chatham hunt country is the ideal location for this grand,...

5
bed
3/1
bath
3,690
sqft
123 Cemetery Road $2,000,000 link

123 Cemetery Road

New Lebanon, NY 12125 | Columbia County
$2,000,000
4 Beds 3/1 Baths 3,648 Sqft 100.94 Acres

If you are considering a purposeful next chapter involving land stewardship, this heirloom farmstead is an exquisite gem with much to offer. With mountain, valley, and pastoral...

4
bed
3/1
bath
3,648
sqft
205 Tompkins Road $2,000,000 link

205 Tompkins Road

Ancram, NY 12502 | Albany County
$2,000,000
4 Beds 2/1 Baths 2,467 Sqft 109 Acres

You know that you are in an extraordinary place, a place that has been preserved in perfect harmony with nature, as soon as you drive down the long tree-lined driveway and arrive...

4
bed
2/1
bath
2,467
sqft
415 Schoolhouse Rd $1,750,000 link

415 Schoolhouse Rd

Ghent, NY 12075 | Columbia County
$1,750,000
5 Beds 3/1 Baths 4,800 Sqft 15.2 Acres

Runaround Farm with 15+ acres provides a gracious relaxed home for all seasons which is bright, airy and set up high with southwesterly views of rollings hills, fields, pond, and...

5
bed
3/1
bath
4,800
sqft
364 Dimmock Rd $1,600,000 link

364 Dimmock Rd

Otis, MA 01253 | Berkshire County
$1,600,000
6 Beds 4 Baths 3,600 Sqft 39.13 Acres

If you are looking for a family compound or a property with potential rental income this expansive 40 acre property will suit your needs to a ''T''. Both homes...

6
bed
4
bath
3,600
sqft
112 Charlie Hill $1,600,000 link

112 Charlie Hill

Millerton, NY 12546 | Dutchess County
$1,600,000
3 Beds 1 Baths 1,782 Sqft 10.14 Acres

The rare opportunity to own an exquisite home designed by David Mann has arrived. Field stone, cedar wood, glass, water and polished concrete work is harmony to create a warm,...

3
bed
1
bath
1,782
sqft
1435 Oblong Rd $1,530,000 link

1435 Oblong Rd

Williamstown, MA 01267 | Berkshire County
$1,530,000
6 Beds 4/1 Baths 6,500 Sqft 8 Acres

Exceptional architectural masterpiece with spectacular views of Mount Greylock and its glorious foothills. The impeccable and sophisticated residence,ideally situated on its own...

6
bed
4/1
bath
6,500
sqft
121 Top Of Dean Hill Rd $1,500,000 link

121 Top Of Dean Hill Rd

Canaan, NY 12029 | Columbia County
$1,500,000
3 Beds 4 Baths 4,000 Sqft 16.85 Acres

This sophisticated Modernist retreat was created by two prominent colleagues of Frank Lloyd Wright: they combined stonework techniques pioneered at Taliesin West with Usonian design...

3
bed
4
bath
4,000
sqft
26 Lilac Ln $1,425,000 link

26 Lilac Ln

Austerlitz, NY 12165 | Columbia County
$1,425,000
3 Beds 2 Baths 2,700 Sqft 12.89 Acres

Inspired design aesthetic, quality construction, thoughtfully sited, meticulously cared for, a sought after location, and glorious views are all a part of this magnificent gem...

3
bed
2
bath
2,700
sqft
988 Hancock Rd $1,300,000 link

988 Hancock Rd

Williamstown, MA 01267 | Berkshire County
$1,300,000
5 Beds 4 Baths 4,137 Sqft 91 Acres

Historic Elegance Meets Modern Luxury at the Gracious Holiday House Nestled in the heart of the Berkshires, Holiday House is a testament to the timeless allure of Williamstown,...

5
bed
4
bath
4,137
sqft