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

​ Buyers
Sellers
Luxury Properties
New Construction
Relocation
Rentals

Areas Covered
​ 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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★★★★★
"Ashley’s knowledge of the area is encyclopedic, her attention to detail without equal...but what makes her the best agent we’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. (Can’t really think of a better recommendation than that.)"

★★★★★
"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 trust—values that guide every transaction. Integrity is the foundation of Ashley’s practice, guiding her commitment to transparency, thoughtful counsel, and unwavering advocacy for her clients’ best interests.

Ashley has earned national recognition for her work, including being named to The Wall Street Journal’s America’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 property’s true value and align clients with homes that reflect their lifestyle and long-term goals, Ashley delivers a highly personalized, elevated experience—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 family’s experience.

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

Ashley Mayhew Dineen’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 CompassUnder Contract - Continue To Show

$15,000,000

5
Bedrooms
10,197
Square Feet
9.26
Acres

865 Hollow Tree Ridge Road, Darien, CT 06820

$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
$8,495,000 | 16 E Trail, Darien, CT 06820
1/40
Listed By Compass

$8,495,000

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

$3,850,000 | 30 Inwood Road, Darien, CT 06820
$3,850,000 | 30 Inwood Road, Darien, CT 06820
$3,850,000 | 30 Inwood Road, Darien, CT 06820
$3,850,000 | 30 Inwood Road, Darien, CT 06820
$3,850,000 | 30 Inwood Road, Darien, CT 06820
$3,850,000 | 30 Inwood Road, Darien, CT 06820
$3,850,000 | 30 Inwood Road, Darien, CT 06820
$3,850,000 | 30 Inwood Road, Darien, CT 06820
$3,850,000 | 30 Inwood Road, Darien, CT 06820
1/9
Listed By CompassUnder Contract - Continue To Show

$3,850,000

6
Bedrooms
5,113
Square Feet
2.9
Acres

30 Inwood Road, Darien, CT 06820

Ashley Mayhew Dineen’s Transactions

Past Sales
$10,495,000 | 10 Rapids Lane, Greenwich, CT 06831

$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

$7,050,000 | 131 Long Neck Point Road, Darien, CT 06820

$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

$4,500,000 | 50 Buttonwood Lane, Darien, CT 06820

$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

$4,325,000 | 3 Edgehill Drive, Darien, CT 06820

$4,325,000

5
Bedrooms
3,919
Square Feet
0.85
Acres

3 Edgehill Drive, 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

a kitchen with stainless steel appliances kitchen island granite countertop a table chairs sink and cabinets

$28,000

6
Bedrooms
7,860
Square Feet
4
Acres

367 Riversville Road, Greenwich, CT 06831

$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