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

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 more than just a local—she’s a passionate advocate for her community. Her deep-rooted connection to the area is evident in every interaction with buyers and sellers, showcasing her unwavering dedication and love for her town.

With a meticulous eye for detail and a profound understanding of the real estate market, Ashley delivers an unparalleled experience for her clients. She values relationships over transactions, building trust, connections, and transparency with clients and colleagues alike.

Ashley's ability to highlight a town's unique appeal and match clients with their ideal properties has garnered her widespread recognition. She has been named in the Wall Street Journal's America’s Best for four consecutive years and is a proud member of Realm, an exclusive group of elite brokers representing the top 1% in the profession. These accolades reflect her unmatched expertise and dedication to her craft.

Residing in Darien with her husband Duke, three college-aged daughters, and a lively menagerie of pets—including four dogs (three of which are rescues), twelve chickens, and a chatty parrot named Diego—Ashley’s home is as vibrant as her professional life. Her oldest daughter’s penchant for fostering animals has only added to the family’s dynamic and loving environment.

Ashley’s commitment to her community extends beyond real estate. She serves as the President of the Board of Directors for The Tiny Miracles Foundation, a non-profit that supports families with premature babies in Fairfield and New Haven Counties. This cause is particularly close to her heart, as her twin daughters were born prematurely at 33 weeks and spent two months in the NICU.

In her free time, Ashley enjoys working in her flower garden, despite promising herself every spring that she won’t buy another peony or order more dahlia tubers!

Ashley’s warmth, expertise, and unwavering dedication make her a trusted ally in the real estate journey. Whether you’re seeking the perfect home or aiming to sell a cherished property, Ashley Dineen is committed to serving the diverse real estate needs of the community with unmatched professionalism and a genuine, friendly spirit.

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 entryway and hall with wooden floor
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 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 an entryway with workspace
a living room with furniture and a fireplace
a front view of a house with a garden
a house with a garden and swimming pool
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
a view of an entryway with hardwood
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 roof deck with table and chairs
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 chair
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
an aerial view of a house
1/38
Listed By Compass

$19,000,000

Bedrooms
6
Bathrooms
7.5
Square Feet
10,197
Acres
4.18

865 Hollow Tree Ridge Road, Darien, CT 06820

a front view of a house with a garden and trees
a car parked in front of white house
a front view of a house with a garden
a view of house with garden space and trees
a view of a lake with couches in the patio next to a yard
a view of a lake with a garden
a view of a lake from a balcony
a front view of a house with plants
a view of entryway livingroom and hall with wooden floor
a view of a dining room with furniture window and outside view
a living room with furniture and a large window
a view of a dining room with furniture and wooden floor
a kitchen with a dining table chairs and white cabinets
a kitchen with a sink stove and cabinets
a view of a workspace with furniture and a potted plant
a large kitchen with a table and chairs
a living room with furniture and a fireplace
a living room with furniture and a large window
a room with pool table and windows
a living room with furniture a fireplace and a large window
a bedroom with a bed and large windows
a living room with furniture a large window and a fireplace
a living room with a couch and a table
a large bathroom with a double vanity sink a mirror and a bathtub
a bathroom with a shower
a bedroom with a bed and a large window
a bedroom with two beds and a chandelier
a view of a livingroom with furniture and book shelf
a bedroom with a bed a flat screen tv and a window
a hallway with cabinets and window
a view of living room with a sink and a refrigerator
a living room with furniture and a flat screen tv
front view of house with a yard
a view of a chairs and table on the deck
a view of a garden with a fountain
a front view of a house with a yard
an aerial view of a house with a yard and lake view
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1/39
Listed By CompassUnder Contract

$7,995,000

Bedrooms
4
Bathrooms
4.5
Square Feet
6,214
Acres
1.22

123 Long Neck Point Road, Darien, CT 06820