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Sleepy Hollow
Orinda

Sleepy Hollow is a wooded valley in north Orinda, known for its stone entry gates and for street names taken from Washington Irving's The Legend of Sleepy Hollow. The neighborhood took its present form in the early 1950s and today has roughly 460 to 470 homes on about 600 acres, with its own elementary school and swim and tennis club. It also takes in Orinda Downs, a newer section built from the late 1960s.

WhereNorth Orinda, around Sleepy Hollow Lane
HomesAbout 460 to 470 homes, plus the newer Orinda Downs section
Typical home (Amy's sales)About 3,300 sq ft, 4 bedrooms
Elementary schoolSleepy Hollow Elementary, 20 Washington Lane
Swim & tennisSleepy Hollow Swim & Tennis Club, 1 Sunnyside Lane
Amy's Sleepy Hollow sales25 and counting

My take on Sleepy Hollow

Sleepy Hollow sits on the north side of Orinda, just past the Country Club area, where the hills start to level out. You get flatter lots and the kind of streets where you can walk to the elementary school or over to a neighbor’s house.

Orinda Downs is part of Sleepy Hollow too, the newer section. Building there started in the late 1960s and early 1970s, and the Downs has wider streets, bigger lots and its own HOA, which includes a park. Like everywhere in Orinda, the homes are custom, so no two look the same. You can find a single-level, three-bedroom, two-bath ranch or, in the upper hills, a 20,000-square-foot compound with several houses and a vineyard.

Halloween is the big event. Lower Van Ripper Lane closes to cars, neighbors throw house parties and the littlest trick-or-treaters get pulled around in wagons. Older kids graduate to the wide streets of Orinda Downs. If you live here, stock up: you need thousands of pieces of candy.

The Sleepy Hollow Swim & Tennis Club is where a lot of new neighbors get to know each other, and there’s plenty of crossover with the elementary school, which puts on a pumpkin patch every fall against the rolling hills. Briones is right behind the neighborhood. You can hike up and look for frogs, though you might find a rattlesnake too.

People sometimes think Sleepy Hollow is tucked away, but you’re about seven minutes from downtown Orinda one way and downtown Lafayette the other, by the back way on Happy Valley Road. Orinda’s downtown is small and local. Lafayette’s is livelier, with more restaurants, Whole Foods, Trader Joe’s and Diablo Foods, the local market everybody loves. Here you get both.

The homes

Developer John Allen began building here in the 1920s under the name Sleepy Hollow Syndicate, and the neighborhood was built out in its present form in the early 1950s. Trees planted on what were once open hillsides have grown into the wooded setting it is known for today.

Orinda Downs, the newer section of Sleepy Hollow, was built starting in the late 1960s and early 1970s, with wider streets, larger lots and its own homeowners association, which includes a park.

Sleepy Hollow has a volunteer neighborhood association, not an HOA, and no binding CC&Rs. The association maintains the neighborhood's Firewise USA certification.

Amy has been part of 25 Sleepy Hollow sales. Across those homes, the typical house was about 3,300 square feet with four bedrooms, ranging from roughly 1,600 to 5,900 square feet. Where lot size was listed, lots ran from about 0.42 acres to 5.9 acres.

Most homes here, like most in Orinda, are older, and the ones that look new have usually been renovated or rebuilt. There are very few empty lots, so building new usually means buying a teardown on a good lot. Fully renovated homes come up less often, usually when an owner relocates, and they sell at a real premium. If you’re open to some updating, your money goes further.

Schools

Sleepy Hollow Elementary School (TK to 5) sits inside the neighborhood at 20 Washington Lane and opened in 1953. Students then attend Orinda Intermediate School (6 to 8) and usually Miramonte High School in the Acalanes Union High School District. In kindergarten through third grade, Orinda classes run about 20 students, and the early-bird and late-bird schedule splits each class into reading groups of about 10 for part of the day.

Attendance areas can change and can vary near the edges, so confirm a specific address with the Orinda Union School District.

Getting around

Camino Pablo connects Sleepy Hollow to downtown Orinda, the Orinda BART station and Highway 24, and Happy Valley Road is the back way into Lafayette. Downtown Orinda and downtown Lafayette are each about seven minutes away by car.

Swim, tennis and community

Sleepy Hollow Swim & Tennis Club on Sunnyside Lane dates to 1955, when residents bought land for a community recreation center. It has an eight-lane racing pool, a recreation pool with a slide, tennis courts and one of the stronger summer swim teams in Contra Costa County.

The Sleepy Hollow Neighborhood Association, founded in 1948 as the Sleepy Hollow Improvement Association, organizes community events and fire safety work.

Briones Regional Park rises right behind the neighborhood, with trails into the open hills.

Homes I've sold in Sleepy Hollow

188 Lombardy Lane, Orinda, Sleepy Hollow, sold by Amy Rose SmithSold

188 Lombardy Lane

+/-3648 Square Feet, 5 Beds, 4 Bath, .76 Acres, Pool | $3,350,000

6 Tappan Lane, Orinda, Sleepy Hollow, sold by Amy Rose SmithSold

6 Tappan Lane

+/- 3,042 3 beds 4 baths, 1.3 acre lot $1,800,000

13 Melody Lane, Orinda, Sleepy Hollow, sold by Amy Rose SmithSold

13 Melody Lane

+/- 3,752 Sq Ft 3 Bed, 3 Bath, 5.88 acre $3,250,000

124 Sleepy Hollow Lane, Orinda, Sleepy Hollow, sold by Amy Rose SmithSold

124 Sleepy Hollow Lane

+/-3639 Sq Ft, 5 Bed, 4 Bath, .48 acres - $2,600,000

31 Normandy Lane, Orinda, Sleepy Hollow, sold by Amy Rose SmithSold

31 Normandy Lane

1604sq ft, 3 Bed, 2 Bath, 0 Garage, 0.64 Acres, $1,380,000

5 Hidden Lane, Orinda, Sleepy Hollow, sold by Amy Rose SmithSold

5 Hidden Lane

3628sq ft, 3 Bed, 2.5 Bath, 2 Garage, 1 Acres, $2,600,000

See all of my sales

Sleepy Hollow questions

Where is Sleepy Hollow in Orinda?

Sleepy Hollow is a wooded valley in north Orinda, around Sleepy Hollow Lane, just north of the Orinda Country Club area. Downtown Orinda and downtown Lafayette are each about seven minutes away by car.

What is Orinda Downs?

Orinda Downs is the newer section of Sleepy Hollow, built starting in the late 1960s and early 1970s, with wider streets, larger lots and its own homeowners association, which includes a park.

Does Sleepy Hollow have an HOA?

Sleepy Hollow itself does not. It has a volunteer neighborhood association, the Sleepy Hollow Neighborhood Association, and no binding CC&Rs. The Orinda Downs section has its own homeowners association.

What school serves Sleepy Hollow?

Sleepy Hollow Elementary School, inside the neighborhood at 20 Washington Lane, followed by Orinda Intermediate School and usually Miramonte High School. Confirm a specific address with the Orinda Union School District.

How many homes are in Sleepy Hollow?

Roughly 460 to 470 homes on about 600 acres. Across the 25 Sleepy Hollow sales Amy has been part of, the typical home was about 3,300 square feet with four bedrooms.

Thinking about Sleepy Hollow?

Whether you're buying or selling here, call or text 925.212.3897, or email amy@amyrosesmith.com.

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