Ashley Mayhew Dineen

Ashley Mayhew Dineen

Licensed Real Estate Salesperson
ashley.dineen@compass.com
M: 203-253-9616
O: 203-423-3100

Social Media

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Awards

WSJ Real Trends America's Best 2020, 2021, 2022, 2023, 2024

Press


CT Cottages & Gardens Deeds and Don'ts:CLICK HERE FOR ARTICLE

Homes.com

Specialties

ā€‹ Buyers
Sellers
Luxury Properties
New Construction
Relocation
Rentals

Areas Covered
ā€‹ Darien
Greenwich
New Canaan
Norwalk
Rowayton

Charity

The Tiny Miracles Foundation
President, Board of Directors

Oak Alley Foundation
Secretary, Board of Directors 
Client Testimonial

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ā˜…ā˜…ā˜…ā˜…ā˜…
"Ashleyā€™s knowledge of the area is encyclopedic, her attention to detail without equal...but what makes her the best agent weā€™ve ever dealt with is her thorough, thoughtful handling of the entire process: from identifying the right area for us to narrowing down our list of houses, and then from negotiating to closing and beyond. Ashley was with us every step of the way, and as a consequence of that, we feel even better about the house we bought. (Canā€™t really think of a better recommendation than that.)"

ā˜…ā˜…ā˜…ā˜…ā˜…
"Ashley was raised in Darien so she is the town expert. This is especially helpful because she can put you in touch with a mortgage broker, attorney the closing, etc. She will help you find the best home you based on your criteria. Coming from Manhattan and apartment living 20+ years, we had some very specific needs our family and she was able to show us homes in our price range that fit those requests. She is a pleasure to work with and she is very tied into the community."


About Ashley

Ashley Dineen is a leading real estate advisor in Darien and across Fairfield County, known for her discretion, market expertise, and unwavering integrity. A lifelong Darien resident, Ashley brings an authentic understanding of the community and a thoughtful, strategic approach to every client relationship.

In 2025, Ashley and her team were recognized as the #1 team in Darien for sales volume, operating from Compass Darien, the #1 office in the market. Her success is rooted in precision, preparation, and trustā€”values that guide every transaction. Integrity is the foundation of Ashleyā€™s practice, guiding her commitment to transparency, thoughtful counsel, and unwavering advocacy for her clientsā€™ best interests.

Ashley has earned national recognition for her work, including being named to The Wall Street Journalā€™s Americaā€™s Best Real Estate Professionals for four consecutive years. She is also a member of REALM, an invitation-only network representing the top 1% of real estate advisors worldwide, offering clients unparalleled reach and access.

Known for her ability to articulate a propertyā€™s true value and align clients with homes that reflect their lifestyle and long-term goals, Ashley delivers a highly personalized, elevated experienceā€”whether representing a significant estate or a primary residence.

Beyond real estate, Ashley serves as President of the Board of Directors for The Tiny Miracles Foundation, supporting families with premature infants in Fairfield and New Haven Counties, a mission shaped by her own familyā€™s experience.

Ashley lives in Darien with her husband Duke and their three college-aged daughters. Her reputationā€”built on integrity, discretion, and resultsā€”has made her a trusted advisor to discerning buyers and sellers who expect excellence at every level.

Ashley Mayhew Dineenā€™s Listings

an aerial view of multiple house
a view of park with trees
a view of building with outdoor space
a view of a hallway with furniture and staircase
a living room with furniture and a fireplace
a view of a dining room with furniture window and outside view
a living room with furniture and a book shelf
a view of a a dining room with furniture window and wooden floor
a living room with kitchen island furniture a flat screen tv and a large window
a kitchen with a stove a sink a dining table and chairs
a kitchen with granite countertop a sink stove and cabinets
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 and a large window
a bedroom with a bed and a table
a bedroom with a bed and a couch
a view of a living room and entry way
a living room with furniture and a fireplace
a front view of a house with a garden
a view of a house with a yard and sitting area
a view of a house with a yard porch and sitting area
a aerial view of a house with a big yard potted plants and large tree
a front view of a house with a garden
a view of entryway livingroom and hall with wooden floor
wooden floor in an empty room with wooden floor and windows
a kitchen with stove and white cabinets
a living room with furniture tv and a floor to ceiling window
a living room with furniture and a large window
a bathroom with a shower
a living room with furniture large window and stainless steel appliances
a room with lots of storage and utility
a living room with furniture and a potted plant
a view of a living room and workspace
a front view of a house with a garden and trees
a view of house with a chairs and table in patio
a view of a backyard with chairs and a potted plant
a view of a house with a yard
an aerial view of a house
$15,000,000 | 865 Hollow Tree Ridge Road, Darien, CT 06820
1/39
Listed By Compass

$15,000,000

5
Bedrooms
10,197
Square Feet
9.26
Acres

865 Hollow Tree Ridge Road, Darien, CT 06820

a front view of a house with yard and green space
a view of a building with a yard
a view of a house with a yard
a front view of a house with a yard and porch
a view of a entryway
a view of entryway with wooden floor
a bed sitting in a bedroom next to a window
a bedroom with a bed and a chandelier
a living room with furniture a bookshelf and a fireplace
a dining room with furniture a chandelier and wooden floor
a view of a dining room with furniture large windows and wooden floor
a kitchen with stainless steel appliances a stove a sink and a refrigerator
a kitchen with stainless steel appliances granite countertop a stove and a sink
a large white kitchen with a large window
a very nice looking kitchen with a large window
a view of a dining room with furniture window and outside view
a living room with furniture a dining table and a fireplace
a view of a fireplace with wooden door
a living room with furniture a rug and a large window
a living room with furniture a rug and a large window
a living room with furniture a flat screen tv and a fireplace
a living room with furniture and wooden floor
a lobby with furniture and large windows
a outdoor living space with furniture and a potted plant
a view of entryway and hall with wooden floor
a bedroom with furniture and a window
a bedroom with a bed and a fireplace
a spacious bathroom with a shower a sink and mirror
a bedroom with a bed and wooden floor
a living room with furniture and a window
a spacious bedroom with a bed and a window
a bedroom with a bed and a window
a room with musical instruments and ceiling fan
a front view of a house with swimming pool and sitting area
a view of a house with swimming pool and sitting area
a view of yard with green space
a view of a house with backyard patio and swimming pool
a outdoor living space with furniture and city view
an aerial view of a residential houses with outdoor space
1/39
Listed By Compass

$8,995,000

9
Bedrooms
8,188
Square Feet
2.89
Acres

16 E Trail, Darien, CT 06820

an aerial view of a house with yard swimming pool and outdoor seating
a front view of a house with a yard and garage
a front view of a house with a garden
a view of a house with a backyard and sitting area
an aerial view of a house
a view of entryway and hall with dining room
a living room with furniture and a fireplace
a living room with furniture and a large window
a living room with furniture and a large window
a dining room with furniture a chandelier and window
a view of a dining room with furniture and window
a kitchen with stainless steel appliances kitchen island granite countertop a table chairs and a wooden floor
a kitchen with a sink stove and window
a kitchen with a sink a window and chairs
a living room with furniture and a fireplace
a living room with furniture and a fireplace
a living room with stainless steel appliances kitchen island granite countertop a refrigerator and a sink
a view of a hallway with wooden floor and windows
a view of a livingroom with a window
a view of a room with gym equipment
a bathroom with a sink and a mirror
a bedroom with a bed and a large window
a living room with furniture and a fireplace
a spacious bathroom with double vanity a sink a mirror a bathtub and next to a window
a bedroom with a large bed and a window
a bathroom with a granite countertop toilet a sink a mirror and a window
a bedroom with a bed and a large window
a spacious bathroom with a double vanity sink a mirror and a shower
a bedroom with a bed and a window
a view of entryway and hall with wooden floor
a living room with furniture rug and window
a view of a table and chairs in backyard
a view of a patio with couches and a fire pit
a house view with swimming pool and chairs
a front view of a house with outdoor seating
a view of a house with a big yard
a view of front door of house with yard
1/37
Listed By CompassUnder Contract

$6,195,000

6
Bedrooms
7,356
Square Feet
1.75
Acres

366 Hollow Tree Ridge Road, Darien, CT 06820

a view of a lake in middle of the town
a front view of a house with a yard
a view of a golf course
a front view of a house with a potted plant
a living room with stainless steel appliances furniture a rug and a view of kitchen
a living room with furniture
a living room with furniture fireplace and large windows
a living room with furniture fireplace and window
a kitchen with granite countertop white cabinets and sink
a living room with furniture and a large window
a dining room with furniture a chandelier and wooden floor
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with stainless steel appliances granite countertop a sink and a stove
a living room with furniture and a window
a view of a door and an entryway
a bathroom with a glass door shower
a living room with furniture and natural light
a bedroom with a bed and large window
a spacious bathroom with a double vanity sink a mirror and a bathtub
a bedroom with a bed a desk and chair with a bookshelf
a bedroom with two beds and wooden floor
a bathroom with a sink a toilet and shower
a living room with furniture and a flat screen tv
a living room with furniture tv and a window
a kitchen with stainless steel appliances a sink a stove cabinets and wooden floor
a view of a dining room with furniture and wooden floor
a outdoor view with a sitting space garden and lake view
a view of a chairs and table under an umbrella in patio
a view of a lake from a yard
an aerial view of a houses with a lake view
a view of a house with a yard
a picture of a park
a picture of floor with a white wall
$3,695,000 | 63 Dorchester Road, Darien, CT 06820
$3,695,000 | 63 Dorchester Road, Darien, CT 06820
$3,695,000 | 63 Dorchester Road, Darien, CT 06820
1/37
Listed By CompassUnder Contract

$3,695,000

4
Bedrooms
3,470
Square Feet
2.75
Acres

63 Dorchester Road, Darien, CT 06820

$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
$2,995,000 | 9 Point O Woods Road South, Darien, CT 06820
1/39
Listed By CompassUnder Contract

$2,995,000

6
Bedrooms
4,848
Square Feet
1.59
Acres

9 Point O Woods Road South, Darien, CT 06820

Ashley Mayhew Dineenā€™s Transactions

Past Sales
a front view of a house with a yard

$10,495,000

6
Bedrooms
12,500
Square Feet
4.03
Acres

10 Rapids Lane, Greenwich, CT 06831

a front view of a house with a garden and trees

$8,000,000

4
Bedrooms
6,214
Square Feet
1.22
Acres

123 Long Neck Point Road, Darien, CT 06820

a front view of a house with a garden

$7,650,000

6
Bedrooms
10,212
Square Feet
3.17
Acres

313 Stanwich Road, Greenwich, CT 06830

$7,300,000 | 313 Stanwich Road, Greenwich, CT 06830

$7,300,000

6
Bedrooms
10,212
Square Feet
3.17
Acres

313 Stanwich Road, Greenwich, CT 06830

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

$7,050,000

4
Bedrooms
4,109
Square Feet
1.29
Acres

131 Long Neck Point Road, Darien, CT 06820

a front view of a house with a yard

$6,975,000

5
Bedrooms
6,685
Square Feet
1.34
Acres

8 Homewood Lane, Darien, CT 06820

a street sign that is on top of a building

$6,500,000

5
Bedrooms
8,093
Square Feet
1.82
Acres

102 Pear Tree Point Road, Darien, CT 06820

a front view of a house with a yard

$6,150,000

6
Bedrooms
8,070
Square Feet
1.62
Acres

6 Homewood Lane, Darien, CT 06820

$6,075,000 | 5 Homewood Lane, Darien, CT 06820

$6,075,000

6
Bedrooms
6,851
Square Feet
2.44
Acres

5 Homewood Lane, Darien, CT 06820

a view of a lake with houses in the back

$6,000,000

4
Bedrooms
6,214
Square Feet
1.22
Acres

123 Long Neck Point Road, Darien, CT 06820

$4,800,000

5
Bedrooms
7,955
Square Feet
1.63
Acres

16 Ox Ridge Lane, Darien, CT 06820

$4,750,000 | 180 Pear Tree Point Road, Darien, CT 06820

$4,750,000

4
Bedrooms
5,990
Square Feet
1.6
Acres

180 Pear Tree Point Road, Darien, CT 06820

$4,550,000 | 15 Allwood Road, Darien, CT 06820

$4,550,000

6
Bedrooms
6,947
Square Feet
2.54
Acres

15 Allwood Road, Darien, CT 06820

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

$4,500,000

7
Bedrooms
7,200
Square Feet
1.64
Acres

50 Buttonwood Lane, Darien, CT 06820

$4,450,000

5
Bedrooms
7,334
Square Feet
6.38
Acres

373 Brookside Road, Darien, CT 06820

Past Rentals
$42,000 | 12 Norfield Farm Lane, Weston, CT 06883

$42,000

6
Bedrooms
8,935
Square Feet
2.08
Acres

12 Norfield Farm Lane, Weston, CT 06883

$10,750 | 29 Tulip Tree Lane, Darien, CT 06820

$10,750

5
Bedrooms
5,451
Square Feet
1.05
Acres

29 Tulip Tree Lane, Darien, CT 06820