111 Deer Hollow Road

Off Market

111 Deer Hollow Road

Sleepy Hollow CA 94960

3856 sq. ft.

40898 sq. ft.

Single-Family

Last sold for $2,850,000

Christopher Backer, last sold this property on 14 July 2026 after 31 days on market.

Overview

Welcome to 111 Deer Hollow Road, a rare opportunity in the highly coveted community of Sleepy Hollow. Set on nearly one acre along one of the neighborhood's most desirable streets, this exceptional property blends timeless character with thoughtful modern upgrades, creating an ideal retreat for today's lifestyle. The expansive 3,856 square foot main residence offers five bedrooms and four bathrooms, while a separate 300 square foot studio above the detached carport provides additional flexibility with its own full bathroom is perfect for guests, a home office, fitness space, or creative studio. Originally built in 1950 and updated over the years, the home features oak flooring throughout the main living areas, dual-pane windows, updated bathrooms with quartz countertops and sleek tile shower surrounds. The home also highlights to grand entertaining spaces with fireplaces in each and tons of windows to maximize natural light. Additional upgrades include updated electrical panels, a Navien tankless water heater, and a new roof with gutter guards installed in 2021. French doors in the living room open to the pool patio, creating seamless indoor-outdoor living. Designed for both everyday comfort and entertaining, the kitchen offers a breakfast nook, two sink areas, a combination of both gas and electric range tops, and a sliding door that leads out to an upgraded composite deck overlooking the western hills and swaying palm trees. The resort-inspired yard showcases a sparkling pool and spa surrounded by mature landscaping, providing a private setting for relaxation and gatherings year-round. The expansive parcel is enhanced by a long paved driveway with abundant parking, a detached carport equipped with a 220-volt outlet ready for EV charging, and three separate basement spaces offering endless possibilities for wine storage, game rooms, workshops, or additional flex storage space. Ideally situated just moments from the Sleepy Hollow Community Center, world-class hiking and biking trails, and the vibrant amenities of both San Anselmo and Fairfax, 111 Deer Hollow Road offers the perfect combination of prestige, privacy, recreation, and convenience. This is Sleepy Hollow living at its finest.

Features

5 bedrooms

5 bathrooms

10 carspaces

4 carport spaces

10 open car spaces

3856 sq. ft. floor area

40898 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Sleepy Hollow over the last 12 months, the estimated median property value of 111 Deer Hollow Road is $2.81m.

Median value

$2.81m

Estimated value range

$1.25m - $5.88m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Sleepy Hollow. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 111 Deer Hollow Road

2026

Sold

$2,850,000

14 Jul 2026 by Christopher Backer, of Corcoran Icon Properties

2025

Rented

Undisclosed

01 Feb 2025 by The Agency

Happy sellers in Sleepy Hollow

94%

94% of sellers in Sleepy Hollow reported that their sale price either exceeded or met their price expectations.

Sleepy Hollow stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 3 reviews in Sleepy Hollow over the last 12 months.

Local market activity for 5 bedroom single-family properties in Sleepy Hollow

In the last 12 months, 13 five-bedroom single-family properties similar to 111 Deer Hollow Road, have been sold.

This represents a 27% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Sleepy Hollow for a market analysis.

Troy Luchessi

at Compass Califorinia

(60 reviews)

Get a market analysis

Garrett Burdick

at Coldwell Banker Realty - Greenbrae

(42 reviews)

Get a market analysis

Keith Offord

at Ross Valley Real Estate

(10 reviews)

Get a market analysis

Dimitri Rigopoulos

at REMAX Dream Homes | Sacramento

(14 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Sleepy Hollow

Troy Luchessi

Sellers who recommend Troy Luchessi have praised them for being local expert, responsive, clear communication, patient, reliable, well-prepared, and honest

5 (60 reviews)
2 Reviews in Sleepy Hollow
2 Sales in Sleepy Hollow

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Garrett Burdick

Sellers who recommend Garrett Burdick have praised them for being local expert, detail-oriented, hard-working, trustworthy, patient, well-prepared, and attentive

5 (42 reviews)
2 Reviews in Sleepy Hollow
1 Sale in Sleepy Hollow

View profile

Keith Offord

Keith Offord is a recommended agent for Sleepy Hollow. They have 1 local sale and collected 1 local review across the last 12 months.

5 (10 reviews)
1 Review in Sleepy Hollow
1 Sale in Sleepy Hollow

View profile

Dimitri Rigopoulos

Dimitri Rigopoulos is an award winning recommended agent for Sleepy Hollow. They have 1 local sale and collected 1 local review across the last 12 months.