Diana Bisselle

Diana Bisselle

Licensed Real Estate Salesperson

Salisbury Brokerage

19 Main Street
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.

She 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 licensed in CT, NY and MA and is 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.

She 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 licensed in CT, NY and MA and is 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.

She 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 licensed in CT, NY and MA and is fluent in Russian.

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My Listings

161 Cornwall Bridge Road $3,500/mo link

161 Cornwall Bridge Road

Sharon, CT 06069 | Litchfield County
$3,500/mo
3 Beds 2/1 Baths 2,484 Sqft 7.33 Acres

Short-term rental with various terms. Available beginning 12/1/2022. Enjoy this ultra private French Country-inspired home approached by a long winding drive through the woods....

3
bed
2/1
bath
2,484
sqft
31 Belgo Road $895,000 link

31 Belgo Road

Lakeville, CT 06039 | Litchfield County
$895,000
3 Beds 3 Baths 1,852 Sqft 1.35 Acres

Charming 3 BDR/3 bath vernacular Federal-era antique perfectly situated to capture seasonal views of Lakeville Lake. According to historical records, the residence was owned by...

3
bed
3
bath
1,852
sqft
0 Sugar Hill Road $600,000 link

0 Sugar Hill Road

Salisbury, CT 06068 | Litchfield County
$600,000
43.49 Acres

Rare Land Opportunity in Salisbury! 43 Private acres located at the end of Sugar Hill Road in the Amesville section of Salisbury. The land has Stone walls, streams, and a mix of...

43.49
acre

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
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
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
8 Upper Church Hill Road $1,625,000 link

8 Upper Church Hill Road

Washington, CT 06794 | Litchfield County
$1,625,000
4 Beds 5/1 Baths 4,500 Sqft 9.46 Acres

This home originally built in the 1800's & then updated in 1948, has been totally renovated w/every attention to detail. Situated on 9+ acres in the heart of picturesque Washington...

4
bed
5/1
bath
4,500
sqft
193 Town Street $1,380,000 link

193 Town Street

Cornwall, CT 06796 | Litchfield County
$1,380,000
3 Beds 3 Baths 3,186 Sqft 14.75 Acres

Distinctive French Country style home located in the coveted Cream Hill section of Cornwall. This architecturally stunning one-level home was completely remodeled in 2007. A beautiful...

3
bed
3
bath
3,186
sqft
49 Canterbury Lane $1,330,000 link

49 Canterbury Lane

Salisbury, CT 06039 | Litchfield County
$1,330,000
3 Beds 3 Baths 3,504 Sqft 1.4 Acres

Imagine sipping your favorite drink and grilling on the back deck of your lakehouse overlooking  Lake Wononscopomuc; or down on the water at the boathouse ready to take that...

3
bed
3
bath
3,504
sqft
21 Fairchild Road $1,200,000 link

21 Fairchild Road

Sharon, CT 06069 | Litchfield County
$1,200,000
3 Beds 2/1 Baths 3,009 Sqft 6.01 Acres

Enjoy stunning westerly views and afternoon sunsets from "Crab Apple Cape" this lovely and private 3 BDR, 2.5 Bath home on 6 gently rolling, sunny acres. A serene approach past...

3
bed
2/1
bath
3,009
sqft