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The San Rafael neighborhood of Glenwood was part of the John A. McNear property at Point San Pedro. Mr. McNear, who played a major role in the development of Marin and Sonoma counties through his shipping and railroad business, purchased 700 acres in the area with his brother George W. McNear in 1859 from the estate of Timothy Murphy, who had been granted 21,680 acres by the Mexican government in 1844 for his missionary work among the Indians. After the brothers split up, John gradually increased his holdings in the area to 2,440 acres. During the 1880's, he and his oldest son George P. McNear, established a fashionable resort area (including a hotel, gardens, and a dance hall), which came to be known as "The Glen", at McNears Beach. In 1898, he and his son, Erskine B. McNear, founded the McNear Brick Company, which still operates today. Erskine commissioned prominent architect Brainerd Jones to design a home on a knoll overlooking what was then the family dairy, the Marin Dell Milk Company, and the 10,732 square foot wood frame home, located at 121 Knight Drive, was completed in 1906. Five years later, in 1911, the Mt. Venice Company of San Francisco received approval to develop Bayside Acres, in the area west of Main Drive and north of Chicken Point.

In August of 1955, the Glenwood portion of the estate was sold to Stegge Development for about $3.3 million. Stegge made sure that the original McNear house was preserved by selling it and the surrounding three acres to the Episcopal Diocese of California in 1957, which continues to own the estate and uses it as a site for a church and a day care center. Stegge and his financial partners, Berkeley Savings and Security Savings, received approval to build the first two subdivisions in Glenwood in late 1955. The homes built by Stegge went up Knight Drive to just past Cottonwood, as well as along Rollingwood and Robinhood as far as Maplewood. In addition, a few homes along Briarwood and Brentwood were also built. Four years later, Unit 4 was approved, and homes along Robinhood, Rollingwood, Maplewood, Heartwood, and Lockwood were built by Security Savings. A short time later, Unit 5 was approved, and homes along the far end of Rollingwood, Robinhood, and Millwood, Lindenwood, and Hazelwood were built by the B & D Development Co. Unit 6 was approved in 1963 and completed in 1965, and Redmond & Walters built homes along Brentwood and Briarwood. Unit 7 was developed by the San Rafael City Schools in 1969 on excess land not needed for school purposes and consisted of the 5 homes directly across from Glenwood School.

The upper part of Glenwood was developed by Perma-Bult Development of San Leandro in the mid-1960's and was called Glenwood Forest. Also known as Peacock Crest, the area was developed by shearing off the eastern part of the ridge where upper McNear Drive is and using the dirt as fill. Unit 1, started in 1965, allowed for homes to be built at the end of Briarwood and Brentwood, as well as homes on Alderwood and on Knight. Unit 2, begun in 1967, finished the development along Knight, and homes were also built along Pinecone, the upper part of McNear Drive, Laurelwood, and most of Woodside (4 lots at the base of Woodside were developed a short time later).

Homes along the ridge between Glenwood and Peacock Gap were built by Latipac-Perini after approvals were received in 1964. The Seaview Heights area, along Castlewood, Cottonwood, Driftwood, and Fairwood, were built beginning in 1965 by D & A Construction. And the Seaview area (Surfwood Circle) was built in the early 70's by Galli Construction. The last major development in the area occurred in 1976, when five large lots were developed by Security Savings in an area called Glenwood Knoll, along what is now Friar Tuck Lane.

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