Diana Bisselle

Diana Bisselle

Global Real Estate Advisor

Salisbury Brokerage

19 Main Street
PO Box 667
Salisbury, CT 06068
  • Born In:
    Sharon, CT
  • Live In:
    Lakeville, CT
  • Languages Spoken:
    English, Russian
  • Passion:
    Exploring the world & Ancient Architectural Wonders
  • Interests:
    Travel, Golf, Ballet & Art

From traveling the world as an Emerging Markets Investment Professional to navigating the winding country roads of Litchfield County, Diana Imperatore Bisselle truly embodies the phrase "local expertise, global connections".

As a resident of Lakeville, CT, Diana has deep roots in, and an unparalleled understanding of, the local real estate market. Born and raised in neighboring Sharon, CT, her parents Philip and Dobrila Waugh founded Waugh Real Estate, a well-known local brokerage covering the Tri-State area for over 30 years. This exposure has instilled in her the importance of superior client service and professional integrity - core values that define The Legacy Team recently launched by Diana and her husband Andrew.

Prior to and complementing her real estate career, Diana worked in New York City for several international investment banks and a hedge fund specializing in Russia, Eastern Europe, Turkey and the Middle East as both an Equity Salesperson and Emerging Markets Portfolio Manager. She has an undergraduate degree in International Relations and Soviet Studies from Boston University and an MA/MBA in Politics and Finance from NYU. 

During her 20+ years in finance, she lived in both Old Greenwich and Darien allowing her to be well-versed in both Litchfield and Fairfield County. She is often found liaising between the two counties, leveraging the resources of the many Sotheby's offices from the coastline to the Litchfield Hills. This is further enhanced by a robust global network unique to Sotheby's.

Diana has been an involved parent at Pear Tree Point School in Darien, Indian Mountain School in Lakeville and Kent School in Kent, CT. She is on the Board of the Lakeville Community Conservancy.

Licensed in CT, NY and MA. Fluent in Russian.

From traveling the world as an Emerging Markets Investment Professional to navigating the winding country roads of Litchfield County, Diana Imperatore Bisselle truly embodies the phrase "local expertise, global connections".

As a resident of Lakeville, CT, Diana has deep roots in, and an unparalleled understanding of, the local real estate market. Born and raised in neighboring Sharon, CT, her parents Philip and Dobrila Waugh founded Waugh Real Estate, a well-known local brokerage covering the Tri-State area for over 30 years. This exposure has instilled in her the importance of superior client service and professional integrity - core values that define The Legacy Team recently launched by Diana and her husband Andrew.

Prior to and complementing her real estate career, Diana worked in New York City for several international investment banks and a hedge fund specializing in Russia, Eastern Europe, Turkey and the Middle East as both an Equity Salesperson and Emerging Markets Portfolio Manager. She has an undergraduate degree in International Relations and Soviet Studies from Boston University and an MA/MBA in Politics and Finance from NYU. 

During her 20+ years in finance, she lived in both Old Greenwich and Darien allowing her to be well-versed in both Litchfield and Fairfield County. She is often found liaising between the two counties, leveraging the resources of the many Sotheby's offices from the coastline to the Litchfield Hills. This is further enhanced by a robust global network unique to Sotheby's.

Diana has been an involved parent at Pear Tree Point School in Darien, Indian Mountain School in Lakeville and Kent School in Kent, CT. She is on the Board of the Lakeville Community Conservancy.

Licensed in CT, NY and MA. Fluent in Russian.

From traveling the world as an Emerging Markets Investment Professional to navigating the winding country roads of Litchfield County, Diana Imperatore Bisselle truly embodies the phrase "local expertise, global connections".

As a resident of Lakeville, CT, Diana has deep roots in, and an unparalleled understanding of, the local real estate market. Born and raised in neighboring Sharon, CT, her parents Philip and Dobrila Waugh founded Waugh Real Estate, a well-known local brokerage covering the Tri-State area for over 30 years. This exposure has instilled in her the importance of superior client service and professional integrity - core values that define The Legacy Team recently launched by Diana and her husband Andrew.

Prior to and complementing her real estate career, Diana worked in New York City for several international investment banks and a hedge fund specializing in Russia, Eastern Europe, Turkey and the Middle East as both an Equity Salesperson and Emerging Markets Portfolio Manager. She has an undergraduate degree in International Relations and Soviet Studies from Boston University and an MA/MBA in Politics and Finance from NYU. 

During her 20+ years in finance, she lived in both Old Greenwich and Darien allowing her to be well-versed in both Litchfield and Fairfield County. She is often found liaising between the two counties, leveraging the resources of the many Sotheby's offices from the coastline to the Litchfield Hills. This is further enhanced by a robust global network unique to Sotheby's.

Diana has been an involved parent at Pear Tree Point School in Darien, Indian Mountain School in Lakeville and Kent School in Kent, CT. She is on the Board of the Lakeville Community Conservancy.

Licensed in CT, NY and MA. Fluent in Russian.

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  • Agent Designations
    • Resort and Second Home Property Specialist
    • Waterfront Property Specialist
  • Awards
    • #1 in Dollar Volume & Units, Salisbury Brokerage - 1H24
    • #1 Team (The Legacy Team at WPSIR) - 1H24
    • 2023 RealTrends America's Best Real Estate Professionals
    • #1 in Dollar Volume, Salisbury Brokerage - 2022
    • Platinum Award - 2022
    • Platinum Award - 2021
    • Diamond Award - 2020

Testimonials

Diana is fantastic - warm, responsive and very knowledgeable about the litchfield county market

Cassie Waduge

Diana Bisselle did a great job listing our house and then helping us buy our next house. She was very responsive and patient with our questions. We strongly recommend her to others looking for real estate expertise.

Robert Miner Kathleen Miner

From the moment I met Diana Bisselle, I knew I was in the most capable, professional hands possible. She listens, she understands, and pleasantly but honestly guides you away from possible pitfalls. I purchased my house from her, and when it was time to sell, there was no question who I was calling to be my agent.

David Beahm

Diana was an absolutely perfect agent for us as first time home buyers. From our first interaction on the phone she was warm, friendly and interested in learning more about us to help us find the perfect home. She offered great advice/direction and was always responsive and timely. She was always early for appointments/showings and always new the right questions to ask the sellers agents about things that we often overlooked or just didn't know to ask. Once it came time to makeing offers she was so helpful getting us to a competitive offer that we felt good about. After that she was exceptional and extremely timely at explaining the steps and guiding us from inspections all the way to closing. We will recommend Diana to anyone looking for a property her territory.

Elizabeth Juusola Peter Juusola

Diana Bisselle is a wonderful agent and a lovely person. She was patient and helpful throughout our house search. We really came to like her very much. We have already recommended her to two of our friends. Thank you

Stephen Scheer

We love Diana. She is great.

Jon Birge Miriam Birge

Hiring Diana to help with my house hunt was the best decision. She is professional and responsive (a breath of fresh air!), and her calm demeanor and sharp wit and kept the stresses of buying my home light and manageable. Everyone should have the pleasure of working with Diana!

Emma O'Brian

I would recommend Diana Bisselle to anyone! She was a pleasure to work with and helped us through buying our first home.

Megan Reed & Nathaniel Bekoe

Diana Bisselle is the absolutely most knowledgeable, responsive, kind, personable, and patient agent we have worked with in over 40 years of purchasing real estate. It was truly a pleasure to work with her. William Pitt/Julia B. Fee Sotheby’s is extraordinarily fortunate to have Diana as part of their team.

Thomas Hays

Outstanding! Our Agent Diana Bisselle supported and mentored us with professional perfection and compassion through a complex sale. If the bar is set at a 10, this team was a 20! I honestly don’t think I could have traveled the “sell journey” without Diana’s exceptional partnership. Thank you! Thank you!

Lynne Calhoun

If first impressions are anything, Diana is a best-case win for your company. From our first phone call to the moment she escorted me to the lawyer's office, I was always met with a pleasant, calming, smile; exacting knowledge of the area (used mainly to gently guide me away from seeing properties she knew would not be a good fit for me); professionalism; accessibility; and the constant feeling that I could trust her guidance every step of the way. I know whom I'll be calling in the future. Thank you.

David Beahm

Diana is brilliant. She has a lovely, engaging personality that matches her professionalism and clear expertise in the CT real estate market. We were so pleased and fortunate to work with her.

Lawrence & Joan Hathaway

Diana was a godsend! She took a difficult situation in hand, with competence and foresight at every turn. Her advice was always on target. Her capacity for diplomacy is extraordinary. She is a consummate professional. I am grateful.

James Lipton

Diana Bisselle was wonderful. When we first showed her the house, she saw it's special qualities exactly as we did. We were amazed at the work she did for us, & the house was sold much quicker than we had anticipated. We credit Diana for this. She made the entire process painless for us, from start to finish. We will highly recommend her in the future. Clark & Claire Smith

Clark & Claire Smith

Diana Bisselle was amazing for us, from start to finish. She saw the special qualities of our house, the property, & its location exactly as we did, before we even told her what we found special about it. We will highly recommend Diana to anyone we know that may sell their house in the future.

Clark & Claire Smith

Diana Bissell, our Sotheby's agent, was fantastic throughout the entire process. Always there to answer every question regardless of the nature of the inquiry. In that regard, I would like to change your question to "How likely is it that you would recommend Diana Bissell to a friend or colleague?" Extremely likely and without reservation. Having bought or sold 6 houses in our lifetime, Diana is by far the best agent we have ever had. Sincerely, Eric and Elise Cieplik

Eric & Elise Cieplik

Diana is an excellent and thoughtful agent.

Ronald & Judith Frost

Working with Diana was an absolute pleasure throughout the entire process, from initial viewing to closing. Dealing with a Foreclosure property was complicated and daunting, but Diana was extremely dedicated to our vision of preserving an 1860's farmhouse. Diana aggressively pursued potential problems to find solutions, whether it was researching town hall records, site visits, or local guidance. As a Sharon resident, Diana really cares about the community as well as her clients and it genuinely shows. I would highly recommend working with Diana Bisselle on any project. Sincerely, Tom & Lizzie

Thoma Pillar & Elizabeth Gill

My Listings

617 Bean River Road $1,575,000 link

617 Bean River Road

Pine Plains, NY 12567 | Dutchess County
$1,575,000
3 Beds 3 Baths 3,833 Sqft 19.28 Acres

Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning...

3
bed
3
bath
3,833
sqft
617 Bean River Road $1,575,000 link

617 Bean River Road

Pine Plains, NY 12567 | Dutchess County
$1,575,000
3 Beds 3 Baths 3,833 Sqft 19.28 Acres

Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning...

3
bed
3
bath
3,833
sqft
18 Old Sharon Road $7,500/mo link

18 Old Sharon Road

Sharon, CT 06069 | Litchfield County
$7,500/mo
5 Beds 4/1 Baths 3,642 Sqft 21.9 Acres

~Fair Rising~ Experience the grandeur of the past with this exquisite 1790 classic Georgian Colonial, nestled on a private 21-acre sanctuary just minutes from the charming center...

5
bed
4/1
bath
3,642
sqft

My Sales

79 Old Cne Road $4,250,000 link

79 Old Cne Road

Lakeville, CT 06039 | Litchfield County
$4,250,000
3 Beds 3 Baths 3,372 Sqft 3.53 Acres

LOCATION-LOCATION-LOCATION!! The old REAL ESTATE saying has never been more true. Located down a country road is this 3.53 acre property with 390 feet of lake frontage. Privacy...

3
bed
3
bath
3,372
sqft
84 Sugar Hill Road $2,750,000 link

84 Sugar Hill Road

Salisbury, CT 06068 | Litchfield County
$2,750,000
4 Beds 3/2 Baths 3,686 Sqft 70.67 Acres

Glen Eden - a quintessential New England country retreat nestled in one of Litchfield County's most sought after towns. Dating back to 1846, this stunning 4 BDR, 3 Bath home has...

4
bed
3/2
bath
3,686
sqft
22 River Road $2,500,000 link

22 River Road

Sharon, CT 06069 | Litchfield County
$2,500,000
4 Beds 3/1 Baths 3,516 Sqft 35 Acres

WHITE HAWK - an impressive 1936 stone farmhouse situated at the foothills of the Berkshires on 35+ private acres. Approach this magical property through stone gates, and up a gently...

4
bed
3/1
bath
3,516
sqft
49 Old Cne Road $2,375,000 link

49 Old Cne Road

Salisbury, CT 06039 | Litchfield County
$2,375,000
4 Beds 4/1 Baths 2,489 Sqft 2.2 Acres

Wononskopomuc Lakefront Cape with Big Eastern Views - Introducing this splendidly renovated Cape Cod nestled in the highly sought-after Wononskopomuc lakefront locale of Lakeville,...

4
bed
4/1
bath
2,489
sqft
26 Fox Run $2,200,000 link

26 Fox Run

Sherman, CT 06784 | Fairfield County
$2,200,000
4 Beds 4/1 Baths 4,867 Sqft 24.77 Acres

Stunning Grand Lodge-style home with a commanding presence and utterly breathtaking views on 24+ elevated, private acres. The beautiful stone and wood facade blends seamlessly...

4
bed
4/1
bath
4,867
sqft
19 Tudor Road $2,075,000 link

19 Tudor Road

Redding, CT 06896 | Fairfield County
$2,075,000
6 Beds 4/2 Baths 6,915 Sqft 20.27 Acres

It’s a LIFESTYLE choice! A way of living that encompasses health, wellness, & an immediate connection with nature (surrounded by a natural, tranquil environment) This completely...

6
bed
4/2
bath
6,915
sqft
234 Gay Street $2,042,500 link

234 Gay Street

Sharon, CT 06069 | Litchfield County
$2,042,500
3 Beds 2 Baths 2,432 Sqft 28.39 Acres

GRANDVIEW FARM ~ one of Sharon's most Iconic barns with legendary views and sunsets! Recently renovated, the interior showcases a unique blend of the original 1920s barn with wood...

3
bed
2
bath
2,432
sqft
25 Canterbury Lane $1,745,000 link

25 Canterbury Lane

Salisbury, CT 06039 | Litchfield County
$1,745,000
4 Beds 3/1 Baths 3,586 Sqft 2.15 Acres

Immaculately maintained, spacious 4 bedrooms, 3.5 bath home with lake & beach rights on Lake Wononscopomuc. Enjoy the association's private beach with dock, a float, and room to...

4
bed
3/1
bath
3,586
sqft
94 Route 7 North $1,724,500 link

94 Route 7 North

Falls Village, CT 06018 | Litchfield County
$1,724,500
5 Beds 3 Baths 3,288 Sqft 7.35 Acres

Ultra-chic country contemporary with remarkable alpinesque views! Impeccably renovated 5 BDR, 3 Bath home and detached 3 car garage in a very special setting surrounded by rolling...

5
bed
3
bath
3,288
sqft