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For Sale

299 Maywood Drive

299 Maywood Drive, San Francisco, CA 94127

$3,850,000
Prominently presiding over an enclave of impressive homes, this rare Monterey Heights property delights the senses with its grandeur, architectural pedigree and spectacular views! The incredible scale of the home offers the new owner an opportunity to reconfigure to meet their specific lifestyle needs. Quality materials and craftsmanship are hallmarks of this building era and are superbly displayed throughout the home. Situated on a sizable lot, wrought iron trellises and a flourish of colorful flora merge with stone walkways & privacy hedges. Designed for expansive living and gracious entertainment, a dramatic two-story foyer with curved wrought iron railed staircase graces the entry. The elegant dining room adjoins a peaceful den/office bathed in natural light. The refreshed classic eat-in kitchen features custom designed Italian tile, newer stainless appliances and a sunny breakfast room for casual dining. A spacious guest bedroom and hall bath, perfectly separated from the public rooms, completes the main level. Measuring at over 1,600sqft, the private upper level and was originally designed for 3 sizable bedrooms but is currently configured as 2 oversized bedrooms w/offices, with the opportunity to reconfigure these rooms, as needed. The grand primary suite features two walk in closets, Juliette balconies and a large adjoining room, ideal as an office or nursery with breathtaking ocean views. A well-scaled second bedroom also features a private office/den area with more ocean views! The expansive lower level is comprised of a casual family room with built-in bar. This level also includes a laundry room, 1/2 bath and several add'l rooms that could be utilized as a home gym, private office space and/or for sporting goods storage. This level has endless development possibilities such as an in-law, ADU or another primary suite. Owned by the same family for 60 years, the recent and extensive capital improvements and structural upgrades create the backdrop for the next stewards to begin their own legacy. Monterey Heights is a serene residential neighborhood known for its tree-lined streets and breathtaking hillside and ocean views. Residents enjoy nearby hiking trails and the wonderful shops and cafes of the popular West Portal shopping corridor. With a quick commute to SFO, Monterey Heights provides the perfect blend of convenience, natural beauty, and community.

4/14/2026 1:00PM - 3:00PM PDT

4/16/2026 5:00PM - 6:30PM PDT

3
beds

3
baths

4,250 Sq.Ft. LIVING AREA

5,771.7 Sq.Ft. lot

Features & Amenities

Interior

  • total bedrooms3
  • Total bathrooms3
  • full bathrooms2
  • half bathroom1
  • Flooring Luxury Vinyl Plank, Tile, Wood
  • Fireplace Wood Burning
  • APPLIANCES Dishwasher, Disposal, Free-Standing Gas Range, Free-Standing Refrigerator, Dryer, Washer
  • other interior Features Cathedral Ceiling(s), Formal Entry, Storage, Wet Bar

Area & Lot

  • Status For Sale
  • OPEN HOUSE

    4/14/2026 1:00PM - 3:00PM PDT

    4/16/2026 5:00PM - 6:30PM PDT

  • Living Area4,250 Sq.Ft.
  • Total Area4,250 Sq.Ft.
  • Lot Area5,771.7 Sq.Ft.
  • MLS® ID426117107
  • TypeResidential
  • YEAR BUILT1927
  • Architecture StylesMediterranean, Spanish
  • View DescriptionCity, Hills, Ocean

Exterior

  • STORIES2
  • Garage Space1.0
  • water SourcePublic
  • utilitiesPublic
  • lot featuresCorner Lot, Landscape Front
  • parkingAttached, Garage Door Opener, Inside Entrance, Private, Independent, On Site (Single Family Only)
  • HEAT TYPECentral
  • sewerPublic Sewer
  • other exterior FeaturesWet Bar

Financial

  • Sales Price$3,850,000
  • HOA $27/yr
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Thank you for your interest in 299 Maywood Drive, San Francisco, CA 94127. We are reviewing your request and will be in touch shortly!

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Work With Heidi

Heidi is a skilled and knowledgeable Agent, experienced in handling the purchase or sale of San Francisco properties. She is committed to handling every detail of your transaction and will see you through the entire process with personalized service and professional results. Deeply committed to her clients, Heidi is diligent in representing them and their best interests.