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Sold for $4,000,000
  • $4,000,000

    299 Maywood Dr, San Francisco, CA 94127

    3beds
    4,250sqft
    Single Family Residence
    Built in 1927
    5,771 Square Feet Lot
    $4,067,200 Zestimate®
    $941/sqft
    $7,938 Estimated rent

    Home value

    $4,067,200

    $3.70M - $4.47M

    $7,938/mo

    Zestimate® history
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    What's special

    Privacy hedgesTree-lined streetsStone walkwaysSizable lotGrand primary suiteSpacious guest bedroomTwo walk in closets
    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Cece A. Doricko DRE #01513516 415-264-7482,

    Compass 415-345-3000,

    Cathy Truelove DRE #01363591 510-333-1382,

    Compass

    Bought with:

    Michael P. Kramer, DRE #01918367

    Engel & Voelkers Mill Valley

    Source: SFAR,MLS#: 426117107MLS LogoOriginating MLS: San Francisco Association of REALTORS

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 3
    • Full bathrooms: 2
    • 1/2 bathrooms: 1
    Rooms
    • Room types: Bathroom, Dining Room, Family Room, Game Room, Kitchen, Laundry, Living Room, Office, Workshop
    Primary bedroom
    • Features: Balcony, Sitting Room, Walk-In Closet
    • Area: 0
    • Dimensions: 0 x 0
    Bedroom 1
    • Area: 0
    • Dimensions: 0 x 0
    Bedroom 2
    • Area: 0
    • Dimensions: 0 x 0
    Bedroom 3
    • Area: 0
    • Dimensions: 0 x 0
    Bedroom 4
    • Area: 0
    • Dimensions: 0 x 0
    Bathroom
    • Features: Shower Stall(s), Tub, Tub w/Shower Over
    Dining room
    • Features: Formal Room
    • Level: Main
    • Area: 0
    • Dimensions: 0 x 0
    Family room
    • Level: Lower
    • Area: 0
    • Dimensions: 0 x 0
    Kitchen
    • Features: Breakfast Room, Pantry Closet, Tile Counters
    • Level: Main
    • Area: 0
    • Dimensions: 0 x 0
    Living room
    • Features: Beamed Ceilings, Sunken, View
    • Level: Main
    • Area: 0
    • Dimensions: 0 x 0
    Heating
    • Central
    Appliances
    • Included: Dishwasher, Disposal, Free-Standing Gas Range, Free-Standing Refrigerator, Dryer, Washer
    Features
    • Cathedral Ceiling(s), Formal Entry, Storage, Wet Bar
    • Flooring: Luxury Vinyl Plank, Tile, Wood
    • Number of fireplaces: 1
    • Fireplace features: Wood Burning
    Interior area
    • Total structure area: 4,250
    • Total interior livable area: 4,250 sqft

    Property

    Parking
    • Total spaces: 1
    • Parking features: Attached, Garage Door Opener, Inside Entrance, Private, Independent, On Site (Single Family Only)
    • Attached garage spaces: 1
    Features
    • Stories: 2
    • Patio & porch: Front Porch, Uncovered Patio
    • Exterior features: Wet Bar
    • Has view: Yes
    • View description: City, Hills, Ocean
    • Has water view: Yes
    • Water view: Ocean
    Lot
    • Size: 5,771 Square Feet
    • Features: Corner Lot, Landscape Front
    Details
    • Parcel number: 3045009
    • Special conditions: Trust

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Mediterranean,Spanish
    • Property subtype: Single Family Residence
    Materials
    • Stucco
    Condition
    • Year built: 1927

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: Public

    Community & HOA

    HOA
    • Has HOA: Yes
    • HOA fee: $27 annually
    • HOA name: Monterey Heights HOA
    Location
    • Region: San Francisco
    • Elevation: 0

    Financial & listing details

    • Price per square foot: $941/sqft
    • Tax assessed value: $163,742
    • Annual tax amount: $2,744
    • Date on market: 4/9/2026
    • Cumulative days on market: 26 days
    • Total actual rent: 0

    Price history

    DateEventPrice
    6/29/2026Sold$4,000,000+3.9%$941/sqft
    Source: SFAR #426117107 Report a problem
    5/7/2026Pending sale$3,850,000$906/sqft
    Source: SFAR #426117107 Report a problem
    4/9/2026Listed for sale$3,850,000+185.2%$906/sqft
    Source: SFAR #426117107 Report a problem
    12/29/1995Sold$1,350,000$318/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$2,744 +2.8%$163,742 +2%
    2024$2,670 +1.9%$160,532 +2%
    2023$2,619 +2.6%$157,385 +2%
    2022$2,553 +2%$154,300 +2%
    2021$2,503 -1.3%$151,276 +1%
    2020$2,535 +3.3%$149,725 +2%
    2019$2,453 +7.1%$146,790 +2%
    2018$2,291 +16.6%$143,912 +2%
    2017$1,964 +3.3%$141,091 +2%
    2016$1,901 +1.4%$138,326 +1.5%
    2015$1,874 +2.7%$136,250 +2%
    2014$1,825 $133,582 +0.5%
    2013-- $132,979 +2%
    2012-- $130,372 +2%
    2011-- $127,816 +0.8%
    2010-- $126,862 -0.2%
    2009-- $127,163 +2%
    2008-- $124,671 +2%
    2007-- $122,228 +2%
    2006-- $119,832 +2%
    2005-- $117,483 +3.9%
    2003-- $113,071 +2%
    2002-- $110,855 +2%
    2001-- $108,684 +2%
    2000-- $106,553
    Find assessor info on the county website

    Neighborhood: Monterey Heights

    Nearby schools

    GreatSchools rating
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    Estimated market value
    $4,067,200
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $4,067,200