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

$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
$6,495,000 | 386 North Street, Greenwich, CT 06830
1/31
Listed By CompassPending

$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 CompassPending

$5,575,000

6
Bedrooms
6,520
Square Feet
0.28
Acres

25 Dialstone Lane, Riverside, CT 06878

a front view of a building with a garden
a room with a baby crib furniture and a dresser
a living room with furniture a rug and a clock
a living room with furniture and a fireplace
a living room with furniture and a wooden floor
a living room with furniture fireplace and flat screen tv
a kitchen with kitchen island granite countertop a refrigerator and a sink
a large kitchen with kitchen island granite countertop lots of counter space and windows
a dining room with furniture and window
a view of a dining room with furniture window and wooden floor
a bathroom with a toilet sink and mirror
a bedroom with a bed and a table
a bedroom with a bed and a large window
a bathroom with a double vanity sink mirror and shower
a bedroom with a bed and a chandelier
a bed room with a bed and a window
a bathroom with a sink toilet and shower
a living room with furniture and a couch
a bed sitting in a bedroom next to a window
a bathroom with a sink toilet vanity and shower
a white bath tub sitting next to a white wall
a view of two chairs on the roof deck
a view of a roof deck with wooden floor and outdoor seating
a view of swimming pool with outdoor seating and trees
a house view with a outdoor space
a building with trees in front of it
1/26
Listed By CompassUnder Contract

$2,695,000

4
Bedrooms
3,416
Square Feet
1.55
Acres

267 Brookside Road, Darien, CT 06820

$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
$1,750,000 | 51 Black Alder Lane, Wilton, CT 06897
1/11
Compass Coming Soon

$1,750,000

5
Bedrooms
3,909
Square Feet
2
Acres

51 Black Alder Lane, Wilton, CT 06897

a front view of house with yard and green space
a front view of a house with a yard table and chairs
a living room with furniture or couch and a large window
a living room with furniture and a large window
a view of a dining room with furniture window and outside view
a kitchen with a stove top oven sink and cabinets
a kitchen with white cabinets and white appliances
a kitchen with a table chairs refrigerator and cabinets
a living room with furniture a flat screen tv and a fireplace
a bedroom with a bed and a window
a bathroom with a sink a mirror a toilet and shower
a bedroom with a bed and a window
a bedroom with a bed and a window
a living room with a bed furniture and a window
a view of a room with gym equipment
a living room with furniture and a large window
a view of a couches in the deck
a view of house with yard and entertaining space
a view of a house with a big yard and large trees
a picture of a wall with a white wall and a painting
a picture of a park
$995,000 | 61 Range Road, Wilton, CT 06897
1/22
Listed By Compass

$995,000

4
Bedrooms
2,000
Square Feet
1.01
Acres

61 Range Road, Wilton, CT 06897

a front view of a house with a yard
a living room with furniture a flat screen tv a rug and a window
a living room with furniture a lamp a rug and a window
a living room with furniture and a flat screen tv
a living room with furniture and a fireplace
a living room with furniture and a large window
a kitchen with white cabinets and stainless steel appliances
a kitchen with white cabinets stainless steel appliances and sink
a kitchen with white cabinets and window
a living room with furniture and a window
a bedroom with bed and a window
a bathroom with a sink and a toilet
a spacious bedroom with a bed and a flat tv screen
a bedroom with a bed flat screen tv on desk and a window
a bedroom with a bed and a window
a bedroom with a bed and wooden floor
a bathroom with a sink toilet and shower
a view of a house with wooden deck and trees
a view of a patio with table and chairs and wooden floor
a house with trees in front of it
$799,000 | 28 Crestview Avenue, Stamford, CT 06907
1/21
Listed By CompassPending

$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, CT 06820

$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
7,000
Square Feet
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

a front view of a building with a garden

$5,352,100

6
Bedrooms
8,252
Square Feet
2.14
Acres

21 Deer Park Drive, Greenwich, CT 06830

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

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

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 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 garden and plants

$21,000

5
Bedrooms
3,448
Square Feet
0.39
Acres

106 Patterson Avenue, Greenwich, CT 06830

$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 yard and a garage

$21,000

5
Bedrooms
10,006
Square Feet
2.01
Acres

125 A Cat Rock Road, Greenwich, CT 06807

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