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 living room with furniture and a large window
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
1/31
Listed By CompassPending

$6,495,000

5
Bedrooms
9,974
Square Feet
2.32
Acres

386 North Street, Greenwich, CT 06830

a front view of a house with a garden and trees
a view of an empty room with wooden floor and stairs
a living room with furniture and a large window
a view of a dining room with furniture
a dining room with furniture and window
a large kitchen with kitchen island a stove a refrigerator a sink dishwasher and white cabinets with wooden floor
a large white kitchen with a large island oven a sink dishwasher and white cabinets with wooden floor
a kitchen with a dining table chairs and large windows
a living room with furniture and a fireplace
a view of cabinets a wooden floor and a window in a room
a view of a hallway with closet area
a bathroom with a sink and a mirror
a bedroom with a bed and a window
a spacious bathroom with a double vanity sink tub and mirror
a bedroom with a bed and a dresser
a en suite bathroom with a granite countertop sink and a mirror
a bedroom with a large bed and a window
a bedroom with a bed and a window
a bathroom with a double vanity sink mirror and double
a spacious bathroom with sinks mirror and tub
a living room with furniture and a flat screen tv
a bathroom with a sink and mirror with bathtub
a view of kitchen with stainless steel appliances refrigerator oven and cabinets
a living room with furniture a flat screen tv and a fireplace
a view of a room with gym equipment
a living room with furniture and a flat screen tv
a bedroom with a bed and a dresser in it
a spacious bathroom with double sink shower and two mirror
a view of a patio with couches fire pit and chairs
a view of a house with backyard porch and sitting area
a view of a big yard with a house in the background
a picture of a yard
1/32
Listed By CompassPending

$3,895,000

5
Bedrooms
7,964
Square Feet
1.22
Acres

17 Vineyard Lane, Westport, CT 06880

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

a aerial view of residential houses with outdoor space
a front view of a house with a yard
a living room with furniture and a garden
a living room with furniture a fireplace and a flat screen tv
a living room with furniture a rug and a window
a view of a livingroom with furniture and a window
a kitchen with a refrigerator and a sink
a kitchen with white cabinets and sink
a kitchen with kitchen island appliances cabinets and counter space
a living room with furniture a flat screen tv and a large window
a bedroom with a bed and a window
a bathroom with a sink toilet and shower
a utility room with dryer and washer
a bathroom with a sink a mirror and a window
a bed sitting in a spacious bedroom next to a window
a bathroom with a sink vanity and mirror
a bed room with a bed and a window
a bedroom with a bed and a window
a bedroom with a bed and a book shelf
a bedroom with a bed and a window
a bedroom with a bed and a dresser
a bathroom with a sink a toilet and a mirror
a living room with furniture large window and a flat screen tv
a living room with furniture fireplace and a flat screen tv
a living room with fireplace furniture and a fireplace
a view of a patio with couches table and chairs and potted plants
a view of a chairs and table in the back yard of the house
a view of a patio with couches and a table and chairs with plants and trees
a view of a swimming pool with a garden
a view of a garden with large trees
a view of a trees in a yard
a view of yard with swimming pool and green space
a view of a house with swimming pool and yard
a view of a house with garden and trees
an aerial view of residential house with outdoor space and trees all around
1/35
Listed By Compass

$2,695,000

6
Bedrooms
4,158
Square Feet
1.74
Acres

176 Carter Street, New Canaan, CT 06840

a front view of a house with a garden
a view of living room
a bedroom with furniture and a window
a living room with furniture and decor
a view of an empty room with a window
a view of a dining room with furniture and wooden floor
a living room with furniture and a large window
a living room with furniture fireplace and flat screen tv
a large kitchen with stainless steel appliances lots of counter top space
a large kitchen with stainless steel appliances a large counter top a stove a sink a refrigerator and a sink
a kitchen with stainless steel appliances granite countertop a sink a stove and cabinets
a view of a dining room with furniture window and wooden floor
a bathroom with a sink and mirror with toilet
a bedroom with bed and a window
a spacious bedroom with a bed and a couch
a bathroom with a double vanity sink a mirror and a shower
a bedroom with a bed and a dresser
a bedroom with a bed and a window
a living room with furniture and a large window
a living room with furniture and a couch
a view of balcony with wooden floor and outdoor seating
a view of a house with backyard and sitting area
a view of a house with a yard and garden
a house view with a outdoor space
$2,395,000 | 33 Fairview Avenue, Darien, CT 06820
1/25
Listed By CompassUnder Contract

$2,395,000

4
Bedrooms
3,102
Square Feet
0.38
Acres

33 Fairview Avenue, Darien, CT 06820

an aerial view of a house with a swimming pool
a living room with furniture a fireplace and a flat screen tv
a living room with furniture a fireplace and a floor to ceiling window
a living room with furniture potted plant and a large window
a view of a balcony with table and chairs under an umbrella
a dining room with furniture and wooden floor
a living room with furniture and a large window
a dining room with furniture a chandelier and window
a kitchen with a table and chairs in it
a dining room with furniture and window
a dining room with a fireplace and a rug
a living room with furniture and a fireplace
a view of door
a bedroom with a bed a table window and couch
a bedroom with a bed and a fireplace
a view of white cabinet with two white cabinet
a spacious bathroom with a sink a toilet and shower
a bathroom with a sink and a bathtub
a room with furniture and window
a view of a room with gym equipment and floor to ceiling windows
a bedroom with a bed and a large window
a living room with furniture and a fireplace
a spacious bedroom with a bed and wooden floor
a bedroom with a bed and a flat screen tv
a kitchen with stainless steel appliances granite countertop a sink and a stove next to a window
a utility room with cabinets washer and dryer
a bedroom with a bed and a window
a bathroom with a toilet sink a shower and a mirror
a living room with furniture and a flat screen tv
a garden view with a seating space
a view of backyard with table and chairs under an umbrella
a front view of a house with garden
a view of a back yard
a view of a white house with a yard and potted plants
$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
1/40
Listed By CompassUnder Contract

$1,750,000

5
Bedrooms
4,732
Square Feet
2
Acres

51 Black Alder Lane, Wilton, CT 06897

$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
$1,595,000 | 493 Valley Road, New Canaan, CT 06840
1/26
Listed By CompassNew

$1,595,000

4
Bedrooms
4,322
Square Feet
2.09
Acres

493 Valley Road, New Canaan, CT 06840

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 CompassUnder Contract

$995,000

4
Bedrooms
2,400
Square Feet
1.01
Acres

61 Range Road, Wilton, CT 06897

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
7.5
Bathrooms

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 and trees

$25,000

5
Bedrooms
6,588
Square Feet
4.1
Acres

345 Round Hill Road, Greenwich, CT 06831

a front view of a house with a yard

$25,000

5
Bedrooms

Undisclosed Address, Westport, CT 06880

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