Jennifer Capala

Jennifer Capala

Licensed Associate Real Estate Broker

Chatham

2 Park Row
Suite 1
Chatham, NY 12037

Great Barrington

306 Main Street
Great Barrington, MA 01230
  • 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

Testimonials

The copy Jen Capala wrote perfectly captured our property as we had come to love it. The accompanying photographs were stunning.

David Conte Suzanne Ouelette

Jennifer Capala was absolutely a joy to work with. Professional and responsive, she got the job done seamlessly. I would request Jennifer again for a house sale as well as I would highly recommend her to others.

Barbara Ann Austin Trust Nancy Jo Austin

Couldn't have asked for a more smooth and professional experience. And Jen Capala is absolutely charming!

Gerard Ferrone

Exceptional service. Jennifer is accommodating and extremely knowledgeable. A very enjoyable experience!

Paul Hyde Sharon Hyde

Jen was a great support and got a great result!

Victoria Clarke

Jen Capala took her fiduciary responsibility very seriously and got the job done. She is true professional, and highly effective realator. I strongly recommend the stellar combination of Jen Capala and Sotheby’s for success!

Heidi Harding

Jennifer was an excellent guide through the process of finding and purchasing a house.

Austin and Krista Sand

The experience with Ms. Capala was extraordinary. Professional, collaborative, great communication which all resulted to a home sale that exceeded our wildest expectations.

Evan Messinger

This was the best real estate transaction experience we have ever had, thanks in no small part to the collaboration of two Sotheby’s agents, one on each side of the deal. To say our agent, Jennifer Capala, outperformed expectations is a gross understatement. She was prepared, thoughtful, strategic, communicative, scrupulously honest, and kind every step of the way. We are so, so glad we chose to work with her and will continue to do so. Her integrity, good humor, and care stand her above so many others we have worked with in the past, and we are so grateful to her and Sotheby’s for this extraordinarily smooth deal.

Paige and John Orloff

Jen Capala is an outstanding broker. After an initial sale fell through, it took her only days to find a new buyer. She was first rate in all her dealings and advice.

Gerald Aksen

Jennifer Capala was wonderful to work with. Though she was the seller's agent, I felt she was honest, strait forward and transparent about everything. I would highly recommend her to anyone looking to buy or sell in the area.

Alexander Dodge Charles Stewart

Greatest

Martin and Karen Mallow

It was a terrific experience to work with Jen. She did her research in helping us price our home at a reasonable price. Her suggestions for staging were invaluable. Jen's attention to detail, communication skills and guidance through the entire selling process were outstanding. We were able to sell our home quickly and without a lot of stress thanks to Jen. Thank you Jen for doing such a terrific job!

pauljchomacl

When I listed my house with Jennifer, she very diplomatically had some suggestions that would make it more appealing for prospective buyers. I agreed and did some "decluttering." She then came and took very professional photographs to post on the website. Most buyers come via the web and Jennifer was always available for a showing and advised me in advance when she was going to be at the house. I found her to be very professional, very candid, and very able to determine serious interest. Her advice during negotiations with a buyer was fair and reasonable. She was knowledgeable about contracts and closing procedures. I recommended Jennifer to a number of people interested in selling their homes and I will continue to do so.

sanper223

I worked with Jennifer twice, first to buy a house and later because I found her such a pleasure to work with I went back to her to get her help selling a house. She knows the area, she is thorough and professional, smart, knowledgable, honest and very easy to work with. Also, she is exceedingly hard working. I live in NYC so she did a lot to legwork for me and saved me time and stress. If I buy another house in that area, she's the first call I will make.

susanturner608

She stuck with us for several years, being innovative and proactive in searching out marketing opportunities relating to the sale of our home. She communicated well and was never too busy to share necessary time with us. Because we live in the UK Jennifer had additional responsibilities when showing our home, presenting it as appropriate to encourage possible buyers. These she undertook with panache and skill. Our buyer was nervous and needed delicate handling throughout the transaction. Without Jennifer's committed involvement I doubt we would have closed the sale when we did. A great thank you to her from very happy sellers.

chj10

Jennifer provided fresh vision and insight to help sell a house that had previously stagnated in the market for over 2 years. The difference between previous brokers and her was immense. She provided staging advice and simple improvements to the house to make it more marketable. She took excellent photos and created a video to help market on line. She targeted second home buyers in NYC area with ads in local magazines. All in all it was an effective, efficient, and easy process that got results in a tough market. A+ effort.

siegelri

Jennifer is top notch and worked really hard for us. We were very specific about where we wanted to live right down to the part of town we wanted to live in. She stuck with us for three years to help us find the exact home we needed in our price range, in the location we wanted. I honestly think most other realtors would have written us off but not Jennifer. She is kind, thoughtful and committed. Without her we wouldn't be in our home now. We closed in December of 2016 and couldn't be happier. Thanks Jennifer!

kva7

Jennifer sold my mother's home in Columbia County. Her expertise at staging, photography and writing were all a part of a successful sale. But it was her personal attention and negotiating skills that proved most important. She communicated so well with potential buyers and let us know exactly what was happening. I would not hesitate to use Jennifer again and would highly recommend her for any real estate transactions in the Hudson Valley or Berkshires.

paulmontana

Jennifer is a super solid broker. She stands behind what she says and she works very hard to get deals closed. She is very knowledgeable about her markets. I could not recommend her more highly. Adam

adam janovic

She is a true professional, attuned to our needs and very knowledgeable with the local areas. She knows how to be informative, without the incessant chatter of many agents. We enjoyed working with her and would refer her to anyone who wants to buy or sell in the Berkshires.

user7674823

My Listings

5392 South Stephentown Road $395,000 link

5392 South Stephentown Road

Stephentown, NY 12168 | Rensselaer County
$395,000
7 Beds 3/1 Baths 3,852 Sqft 5.32 Acres

A unique Colonial Grand Dame with 7 bedrooms and many large gathering spaces sitting tall on a beautiful 5 acre lot with mountain views and a stream in Stephentown, NY. The first...

7
bed
3/1
bath
3,852
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

Over 26,000 years ago a geological event spanning approximately 10,000 years is the inspiration behind Kushner Studio's latest residential project in Gardiner, NY. The site...

4
bed
3/1
bath
4,234
sqft
1175 County Route 27a $9,995,000 link

1175 County Route 27a

Copake, NY 12516 | Columbia County
$9,995,000
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

My Sales

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
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
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
581 Harrington Drive $1,200,000 link

581 Harrington Drive

Austerlitz, NY 12017 | Columbia County
$1,200,000
3 Beds 2/1 Baths 1,850 Sqft 8.3 Acres

Masterfully imagined, minimally modern take on an elegant post and beam country home. A playful, warm, inviting vibe will fill you with joy, while the architect's use of light,...

3
bed
2/1
bath
1,850
sqft
581 Harrington Dr $1,170,000 link

581 Harrington Dr

Austerlitz, NY 12017
$1,170,000
3 Beds 2/1 Baths 1,850 Sqft 8.3 Acres

Elegantly designed and built in 2017, this property features custom details throughout, with an eye toward light, flow and a seamless connection to nature. Set on 8.3 wooded acres,...

3
bed
2/1
bath
1,850
sqft
599 Whippoorwill Rd $1,037,500 link

599 Whippoorwill Rd

Hillsdale, NY 12529 | Columbia County
$1,037,500
7 Beds 4/1 Baths 4,500 Sqft 78.67 Acres

European flare in Hillsdale, NY. Grand in every way. Big acreage for privacy, open fields, expansive western views, gracious sized rooms, screened porch large enough for gathering,...

7
bed
4/1
bath
4,500
sqft