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

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