Cutty & Dana
2260 Forest View Ave
Hillsborough, CA



Entering the wrought-iron gates of this magnificent estate brings one into an extraordinary “zone” artistically designed by renowned landscape architect Topher Delaney.

The elegant 19th century home is reminiscent of a Kennedy compound, commanding a great presence on nearly an entire acre. The home is approximately 10,000 square feet and features seven bedrooms and seven and one-half baths.

The main entry features a grand entry facing the spiral staircase. To one side is the large living room with a wood-burning fireplace and windows facing the pool area. To the other side at the entry is a ground floor bedroom suite and a charming wood paneled office, also with a fireplace.

The formal dining room is magnificent and large, while a separate dessert room is exquisite with detailed moulding, its own fireplace and doors and windows to the gardens. This is a beautiful space to entertain guests.

The kitchen features a gas Garland stove, Sub-Zero refrigerator and looks out to the side outdoor dining area. A unique feature of the kitchen is an exposed antique built-in safe which adds a lot of character to the space.

A small nook with built-in seating is a casual area for dinners; nearby is the family room which is offers three separate sitting areas.

A discreet office with built-ins is conveniently tucked off the family room.

The second floor features the master suite with its own deck overlooking the yard, a grand fireplace, huge walk-in closet and sitting area. The master bath has a separate tub and shower and two sinks with granite countertops.

On this floor are three other bedrooms as well as one room that functions as a bedroom but does not have a designated closet.

On the top level is a suite with separate living room and bath that works perfectly as an au pair unit, a generous attic for storage and a charming bedroom with a bath.

The property is an entertainer’s paradise, featuring a huge pool, sports court, putting green, and patios.


Landscape design by Topher Delaney

This amazing compound has been completed with the garden designs of renowned landscape architect –  Topher Delaney.  Ms. Delaney has devoted her professional life to developing a practice which serves to transform both private residential and public sites into beautiful garden sanctuaries The inspiration for these beautiful gardens was the site’s unique historical profile, the perfect canvas to create new spaces and interpretations within the classic compound.


For a private showing, please contact: Cutty at (650) 580-8286 or Dana at (415) 264-5464

About the agents

Cutty Smith

Cal BRE# 01444081

Cutty Smith

Originally from a New England real estate family based in the Dartmouth College community, Cutty now resides in Woodside.

For the past 10 years she has been one of the top Realtors in the area with an in depth knowledge of the local neighborhoods and their particular market dynamics.   Cutty is known for her resolute commitment,  focus on detail, and commanding negotiation skills.  By understanding her clients’ needs and goals, she manages transactions is a positive, stress free manner that fulfills
her clients expectations.  The partner you demand, the results you expect!

Cutty has been in the Top Producer  and President’s Circle for 2013, 2014, 2105 and 2016,  and has  successfully represented buyers and sellers with both “on and off” market properties from San Francisco to Saratoga.

Cutty graduated from the University of Vermont with a BS in Marketing. She also studied International Marketing and Swedish at the University of Lund, Sweden.

As a trained Gemologist, specializing in Estate Jewelry Appraisals, Cutty used to live in the Cayman Islands, where she developed her sales skills, while managing several jewelry stores, and creating a Jewelry Appraisal Company.

Prior to entering real estate, she was also a Social Director with the Cunard/Seabourn Cruise Ship lines and traveled around the world on the QEII.

As an active in the community, she is a member of the History Committee for the town.  She also volunteers at the Village Church Rummage sale and for the Old La Honda Rd Committee.

When she can get away, skiing, sailing, and world traveling are her passions.


Dana Cappiello

Cal BRE#: 01343305

Dana Cappiello

Dana Cappiello represents equestrian properties, large estates, housing developments, cannabis cultivators and anyone looking for a spectacular home.

Dana was a clothing designer prior to becoming a real estate agent and owned her own design firm, Dax & Coe. She was the original designer for the apparel line INC, a private label for the Federated Department Stores.

Dana is also the cofounder of the Until There’s a Cure Foundation, which distributes the AIDS bracelet. The foundation has had a major impact on the AIDS community and was the initial funder for two important AIDS vaccine foundations, the International Aids Vaccine Initiative and the AIDS Vaccine Advocacy Coalition, both of which are now funded by the Bill and Melinda Gates Foundation for over $500,000,000.

Dana is energetic, hardworking and enthusiastic. She has a positive attitude and can handle fast-paced transactions. She has an extensive marketing background, both domestically and internationally.



  • Cutty Smith
    (650) 580-8286
  • Dana Cappiello
    (415) 264-5464
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