The Jennifer Leahy Team

The Jennifer Leahy Team

thejenniferleahyteam@compass.com
M: 917-848-0341

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Revenue

Over $1B in Career Sales
$167M Sold in 2023
$132M Sold in 2024
Sold Great Island, Darien for $85M in 2023

About The Jennifer Leahy Team
With over $1.25 billion in closed sales, The Jennifer Leahy Team is a top-performing leader in Connecticut and New York's suburban real estate markets. Recognized as Douglas Elliman’s #1 team in Connecticut from 2019 to 2024, their excellence reflects an unwavering commitment to superior client service and outstanding results.

Now at Compass, the team leverages cutting-edge technology and exclusive resources, including Compass’ Private Off-Market Exclusive program, to connect buyers with unlisted properties and offer sellers unparalleled discretion and unique opportunities.

Renowned for white-glove service, innovative marketing strategies, and comprehensive expertise, the team brings deep local knowledge and a network of connections that ensure every transaction is seamless.

Whether partnering with first-time buyers, seasoned sellers, or major developers, The Jennifer Leahy Team’s combined and collaborative expertise, fueled by a relentless passion for excellence, consistently sets industry standards. Leveraging Compass’ innovative tools and their own creative strategies, they redefine what success means in real estate.

The Jennifer Leahy Team’s Listings

an aerial view of a house
a living room with furniture and a large window
a living room with furniture and a chandelier
a dining room with wooden floor a chandelier a wooden table and chairs
a kitchen with stainless steel appliances kitchen island granite countertop a sink and cabinets
a kitchen with stainless steel appliances a stove sink and cabinets
a kitchen with cabinets stainless steel appliances and counter space
a kitchen with white cabinets and white appliances
a living room with fireplace furniture and a large window
a living room with fireplace furniture and a large window
a living room with furniture fireplace and flat screen tv
a spacious bedroom with a large bed and a couch
a living room with furniture and a wooden floor
a view of a hallway with wooden floor and stairs
a view of entryway and hall with a couch
a kitchen with a sink and a refrigerator
a living room with furniture and a rug
a living room with furniture and a wooden floor
a view of a dining room with furniture window and wooden floor
a bedroom with a bed and a large window
a bedroom with a bed and a table
a bedroom with a large bed and a large window
a bedroom with a bed and a window
a spacious bedroom with a bed and a view of kitchen
an open kitchen with a fireplace and outdoor view
a view of a livingroom with wooden floor and cabinet
a view of entryway with wooden floor
a view of a room with gym equipment
a bathroom with a sink and curtain
a aerial view of a house with backyard and pool
$6,495,000 | 386 North Street, Greenwich, CT 06830
1/31
Listed By Compass

$6,495,000

5
Bedrooms
9,974
Square Feet
2.32
Acres

386 North Street, Greenwich, CT 06830

$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
$5,575,000 | 25 Dialstone Lane, Riverside, CT 06878
1/35
Listed By Compass

$5,575,000

6
Bedrooms
6,520
Square Feet
0.28
Acres

25 Dialstone Lane, Riverside, CT 06878

$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
1/21
Listed By CompassContingent Contract

$799,000

4
Bedrooms
2,081
Square Feet
0.18
Acres

28 Crestview Avenue, Stamford, CT 06907

The Jennifer Leahy Team’s Transactions

Past Sales
an aerial view of a house with a lake view

$85,000,000

10
Bedrooms
13,107
Square Feet
60.92
Acres

19 Great Island, Darien, CT 06820

an aerial view of a house with a lake view

$85,000,000

10
Bedrooms
13,107
Square Feet
60.92
Acres

Great Island, Darien, CT 06820

Undisclosed Address, Darien

$12,500,000

5
Bedrooms

Undisclosed Address

Darien

a view of a garden with plants

$11,770,000

7
Bedrooms
9,500
Square Feet
5.12
Acres

205 Round Hill Road, Greenwich, CT 06831

an aerial view of a house with a yard and outdoor seating

$11,000,000

7
Bedrooms
9,174
Square Feet
4.01
Acres

3 Hekma Road, Greenwich, CT 06831

a front view of a house with a garden and plants

$10,500,000

5
Bedrooms
8,804
Square Feet
0.88
Acres

11 Pratt Island, Darien, CT 06820

a front view of a house with a garden

$10,250,000

7
Bedrooms
10,058
Square Feet
8
Acres

35 A Andrews Farm Road, Greenwich, CT 06831

a front view of a house with a yard

$7,975,000

4
Bedrooms
6,902
Square Feet
0.75
Acres

2 Martin Dale, Greenwich, CT 06830

a front view of a house with garden

$7,850,000

8
Bedrooms
12,988
Square Feet
13.03
Acres

21 Hurlingham Drive, Greenwich, CT 06831

an aerial view of a house with a garden and lake view

$7,000,000

5
Bedrooms
6,044
Square Feet
1.01
Acres

116 Birch Lane, Greenwich, CT 06830

$6,750,000 | 485 Laurel Road, New Canaan, CT 06840

$6,750,000

8
Bedrooms
17.5
Acres

485 Laurel Road, New Canaan, CT 06840

a front view of a house with a yard and potted plants

$6,500,000

5
Bedrooms
7,809
Square Feet
1.25
Acres

8 Butlers Island Road, Darien, CT 06820

$6,400,000 | 558 Lake Avenue, Greenwich, CT 06830

$6,400,000

7
Bedrooms
9,281
Square Feet
2.98
Acres

558 Lake Avenue, Greenwich, CT 06830

$6,250,000 | 19 Old Hill Farms Road, Westport, CT 06880

$6,250,000

5
Bedrooms
7,595
Square Feet
0.96
Acres

19 Old Hill Farms Road, Westport, CT 06880

an aerial view of residential house with outdoor space and trees all around

$6,050,000

6
Bedrooms
5,210
Square Feet
1.03
Acres

2 Sparrow Lane, Greenwich, CT 06830

a view of a lake with a house in the background

$6,000,000

7
Bedrooms
6,918
Square Feet
13.94
Acres

432 Frogtown Road, New Canaan, CT 06840

Past Rentals
a front view of a house with a garden

$72,000

7
Bedrooms
8,208
Square Feet
1.01
Acres

4 Winker Lane, Westport, CT 06880

a view of a lake view

$70,000

7
Bedrooms
11,615
Square Feet
4
Acres

895 Lake Avenue, Greenwich, CT 06831

a front view of a house with a dirt yard

$50,000

4
Bedrooms
4,459
Square Feet
2.62
Acres

555 North Street, Greenwich, CT 06830

an aerial view of a house with a swimming pool

$35,000

4
Bedrooms
5,409
Square Feet
1.12
Acres

46 Burr Farms Road, Westport, CT 06880

a view of a swimming pool with a patio

$35,000

5
Bedrooms
7,069
Square Feet
1
Acres

91 Turkey Hill Road South, Westport, CT 06880

a view of a house with a big yard and large trees

$30,000

5
Bedrooms
6,020
Square Feet
2.51
Acres

47 Carriglea Drive, Riverside, CT 06878

$28,500 | 47 Carriglea Drive, Riverside, CT 06878

$28,500

5
Bedrooms
6,075
Square Feet
2.51
Acres

47 Carriglea Drive, Riverside, CT 06878

an aerial view of multiple house with a yard

$27,500

4
Bedrooms
6,020
Square Feet
2.51
Acres

47 Carriglea Drive, Riverside, CT 06878

an aerial view of multiple house with a yard

$26,500

5
Bedrooms
6,020
Square Feet
2.51
Acres

47 Carriglea Drive, Riverside, CT 06878

a front view of a house with a yard and a garage

$25,000

5
Bedrooms
7,297
Square Feet
2.01
Acres

125 Cat Rock Road, Cos Cob, CT 06807

a front view of a house with a yard

$25,000

5
Bedrooms

Undisclosed Address, Westport, CT 06880

a front view of a house with a yard and trees

$25,000

5
Bedrooms
6,588
Square Feet
4.1
Acres

345 Round Hill Road, Greenwich, CT 06831

a view of a big house with a big yard and large trees

$24,000

4
Bedrooms
4,540
Square Feet
1.14
Acres

23 Old Orchard Lane, Stamford, CT 06903

$23,000 | 47 Carriglea Drive, Riverside, CT 06878

$23,000

5
Bedrooms
6,020
Square Feet
2.51
Acres

47 Carriglea Drive, Riverside, CT 06878

a front view of a house with a yard and a garage

$21,000

5
Bedrooms
10,006
Square Feet
2.01
Acres

125 A Cat Rock Road, Greenwich, CT 06807

$21,000 | 7 Evergreen Lane, Larchmont, NY 10538

$21,000

6
Bedrooms
11,617
Square Feet
3.40
Acres

7 Evergreen Lane, Larchmont, NY 10538

Listing Courtesy of Douglas Elliman Real Estate

a front view of a house with a garden and plants

$21,000

5
Bedrooms
3,448
Square Feet
0.39
Acres

106 Patterson Avenue, Greenwich, CT 06830

a front view of a house with a garden and plants

$20,000

5
Bedrooms
3,448
Square Feet
0.39
Acres

106 Patterson Avenue, Greenwich, CT 06830