San Mateo, CA Homes

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  $2,950,000 Open Sun 1:30PM - 4:30PM

  • 4 Beds
  • 2 Baths
  • 1,660 Sq Ft

  291 La Mesa Dr, Portola Valley, CA 94028

  Mid-century modern diamond in the rough. Unlock the full potential of this 4-bedroom, 2-bath mid-century modern gem nestled in the desirable Ladera neighborhood. Set on a private and spacious corner lot with mature landscaping, this home is brimming with opportunity for the savvy buyer to renovate and restore its original charm or build your dream home from the ground up. Convenient to the Ladera

  Rebecca Johnson Intero Real Estate Services

  291 La Mesa Dr, Portola Valley, CA 94028
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  Explore Portola Valley

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  $14,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  15 Kiowa Ct, Portola Valley, CA 94028

  Private, Open contemporary home. 5 Bedrooms, 3 baths, 3500sf.(per owner). Highly desired Central Portola Valley! Expansive Views of the Western Hills from Windy Hill to Woodside. Great Schools! Elementary schl 1 mile. Quick access to highway 280, Stanford Campus, shopping Recently Remodeled. Vaulted ceilings, Open floor plan including the Living room, Dining Room, Kitchen. Floor to ceiling

  Terrell Slawson Linwood Realty Inc.

  15 Kiowa Ct, Portola Valley, CA 94028
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  $6,020,000 Sold Jul 28, 2025

  • 2,905 Sq Ft
  • $2072/SF
  • 7 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1954

  22 Grove Dr, Portola Valley, CA 94028

  Modern Luxury on 2+ Acres with Windy Hill Views || Striking modern design, total privacy, and chic designer interiors define this exceptional property in the heart of central Portola Valley. Gated at the end of a long driveway and spanning over 2 acres, the setting offers expansive grounds with views toward Windy Hill and a layout designed for effortless indoor/outdoor living. Every detail of the

  Erika Demma Compass

  22 Grove Dr, Portola Valley, CA 94028
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  Est $4,075,304 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,497 Sq Ft

  118 Ramona Rd, Portola Valley, CA 94028

  118 Ramona Rd, Portola Valley, CA 94028
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  $3,599,000

  • 4 Beds
  • 3.5 Baths
  • 3,470 Sq Ft

  21 Valley Oak St, Portola Valley, CA 94028

  Escape to serenity in this very private 4-bedroom, 3.5-bathroom retreat priced at $3,599,000. Spanning 3,470 square feet on a 25,966 SF lot, this 1988-built residence blends timeless elegance with modern sophistication. The light-filled interior boasts soaring ceilings, large windows, new paint, and lighting throughout, creating an inviting open-concept layout ideal for both grand entertaining

  Nathan Nahouraii Intero Real Estate Services

  21 Valley Oak St, Portola Valley, CA 94028
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  $13,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,520 Sq Ft
  • House for Rent

  16 Franciscan Ridge, Portola Valley, CA 94028

  Views! Preeminent location on Franciscan Ridge with extraordinary sunrise and sunset views that span across Portola Valley, toward Stanford Dish, and beyond to the bay and Diablo Mountain range. This home is one of the largest Portola Valley Ranch homes, featuring 4 bedrooms plus an office, 3.5 bathrooms, an oversized living room with a fireplace, formal and informal dining adjacent to a chef's

  Dulcy Freeman Golden Gate Sotheby's International Realty

  16 Franciscan Ridge, Portola Valley, CA 94028
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  $1,100,000 Sold Jul 23, 2025

  • Land
  • 1.65 Acres
  • $666,667 per Acre

  • 279 Days On Market

  42 Santa Maria Ave, Portola Valley, CA 94028

  A great opportunity to build in a scenic and close-in Portola Valley neighborhood. The sunny, approximately 1.65 acre lot comes with approved building plans from the Town. Plans are for an approximately 2000 square foot home with 2 bedrooms and 2 full and 1 half baths and an additional 800 square foot ADU with 1 bedroom, 1 bath on the upper level. Alternatively, the ADU could be used as the

  Ginny Kavanaugh Coldwell Banker Realty

  42 Santa Maria Ave, Portola Valley, CA 94028
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  Not Listed For Sale

  0 Alpine Rd, Portola Valley, CA 94028

  0 Alpine Rd, Portola Valley, CA 94028
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  $9,399,000

  • 6 Beds
  • 9 Baths
  • 7,531 Sq Ft

  5 Redberry Ridge, Portola Valley, CA 94028

  Prominently perched on the Portola Valley hillside, this contemporary home has been upgraded with the finest materials and craftsmanship providing glorious panoramic views of rolling hills with Silicon Valley and the Bay in the distance. This home is elegant, sophisticated and secluded and just a short drive to Silicon Valley with easy freeway access. The flexible floor plan includes six bedroom

  Omar M. Kinaan Golden Gate Sotheby's International Realty

  5 Redberry Ridge, Portola Valley, CA 94028
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  $10,500 per month

  • 5 Beds
  • 3.5 Baths
  • 2,940 Sq Ft
  • House for Rent

  270 Gabarda Way, Portola Valley, CA 94028

  This luxury summer rental, available August 1 through November 15 2025 for a minimum 1 month stay, is nestled in Portola Valley, a quiet town abutting the Santa Cruz mountains, yet just minutes from highway 280, and a few minutes further to Stanford University & Hospital and to major employers. The home is well equipped, tastefully appointed, fully furnished, and has 5 bedrooms, an office, an

  Kevin Boer Kevin Boer, Broker

  270 Gabarda Way, Portola Valley, CA 94028
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  $2,950,000 Sold Jun 25, 2025

  • 1,770 Sq Ft
  • $1667/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  3 Wyndham Dr, Portola Valley, CA 94028

  On the market for the first time in nearly 50 years, this classic ranch home is set on a lushly planted corner lot of approximately one-third acre. Gardens are the soul of this property - loving tended & richly layered with heritage roses, wisetria, towering redwoods, & a soothing water feature. Brick walkway winds through the front gardens, while the private rear grounds invite outdoor living

  Hugh Cornish Coldwell Banker Realty

  3 Wyndham Dr, Portola Valley, CA 94028
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  Est $4,002,142 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,155 Sq Ft

  25 Las Piedras Ct, Portola Valley, CA 94028

  25 Las Piedras Ct, Portola Valley, CA 94028
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  $6,988,000

  • 4 Beds
  • 3 Baths
  • 2,940 Sq Ft

  40 Tagus Ct, Portola Valley, CA 94028

  Tucked away on nearly 2 acres at the end of a quiet cul-de-sac in lush Portola Valley, this updated contemporary home offers the perfect blend of privacy and natural beauty. Bright, airy interiors feature high ceilings and a mix of travertine and oak floors, creating a warm and inviting atmosphere. The spacious living areas, including a large great room and chef's kitchen with top-tier

  Michael Repka Deleon Realty

  40 Tagus Ct, Portola Valley, CA 94028
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  $4,412,000 Sold Jun 24, 2025

  • 3,190 Sq Ft
  • $1383/SF
  • 15 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2011

  1036 Los Trancos Rd, Portola Valley, CA 94028

  Nestled on a gorgeous virtually flat half acre this stunning Mediterranean style home is surrounded by the pristine beauty of the adjacent Blue Oaks open space, with VIEWS stretching across the East Bay to the glittering Oakland skyline. Masterfully built in 2011 the homes thoughtful design marries a spacious, versatile floor plan with exquisite details: soaring reclaimed wood beams, graceful

  Liz Daschbach Compass

  1036 Los Trancos Rd, Portola Valley, CA 94028
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  Not Listed For Sale

  132 Foxwood Rd, Portola Valley, CA 94028

  132 Foxwood Rd, Portola Valley, CA 94028
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  $5,488,000

  • 4 Beds
  • 5.5 Baths
  • 4,210 Sq Ft

  5 Oak Forest Ct, Portola Valley, CA 94028

  Nestled on more than 1.5 acres, this exquisite home has been thoughtfully transformed to deliver an unparalleled living experience. With more than 4,200 sf, the home exudes luxury, from its soaring ceilings and impeccable finishes to the dramatic use of glass. Expansive living areas, multiple fireplaces, a gourmet kitchen, and an executive office offer both comfort and style. Four bedrooms are

  Michael Repka Deleon Realty

  5 Oak Forest Ct, Portola Valley, CA 94028
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  $1,850,000 Sold Jun 23, 2025

  • 860 Sq Ft
  • $2151/SF
  • 79 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  1023 Los Trancos Rd, Portola Valley, CA 94028

  Luxury Silicon Valley Getaway in Portola Valley with Views, updated single family /rustic modern interior, move-in ready and personal retreat on a large 11,500 square foot lot, surrounded by natural beauty, a network of trails. Open floor plan with natural light throughout, skylights, hardwood floors, built in bookshelves, new kitchen and appliances, eat-in kitchen and sliding glass doors to

  Karen Gunn Compass

  1023 Los Trancos Rd, Portola Valley, CA 94028
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  Est $5,002,000 Not Listed For Sale

  • 5 Beds

  12 Arastradero Rd, Portola Valley, CA 94028

  12 Arastradero Rd, Portola Valley, CA 94028
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  $7,998,000

  • 4 Beds
  • 4 Baths
  • 2,630 Sq Ft

  600 Westridge Dr, Portola Valley, CA 94028

  This rare offering truly has it all 2.5 acres in the prestigious Westridge area with complete privacy set back from the street, San Francisco and foothill views, a regulation-size tennis court, resort-style pool with elevated spa and waterfall, and a poolside sauna with an outdoor shower. The well-appointed classic ranch home features bright and light interiors with fine hardwood floors

  Dean Asborno Compass

  600 Westridge Dr, Portola Valley, CA 94028
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  $6,550,000 Sold Jun 18, 2025

  • 2,860 Sq Ft
  • $2290/SF
  • 12 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1966

  30 Cheyenne Point, Portola Valley, CA 94028

  Transformed with a whole-home renovation, this exquisite home offers luxurious designer style and wellness-focused amenities in a prime Central Portola Valley location. Every detail has been elevated, with stunning interiors featuring heated tiled floors in every room. Expansive retractable glass doors create a seamless indoor/outdoor connection in the living and dining room plus there is a

  Erika Demma Compass

  30 Cheyenne Point, Portola Valley, CA 94028
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  Est $4,521,042 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,325 Sq Ft

  18 Arastradero Rd, Portola Valley, CA 94028

  18 Arastradero Rd, Portola Valley, CA 94028
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  $2,950,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  10 Bear Gulch Dr, Portola Valley, CA 94028

  VALUE VALUE VALUE! Nestled in the heart of one of Silicon Valleys most sought-after communities, 10 Bear Gulch Drive in Portola Valley presents a rare and exciting opportunity. This timeless Craftsman-style home sits on a sprawling 1.25-acre parcel and offers a 3-bedroom, 2-bath main residence plus a detached guest cottageideal for extended family, home office, or rental potential. Priced to sell

  Danny Burgess eXp Realty of California Inc

  10 Bear Gulch Dr, Portola Valley, CA 94028
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  $4,250,000 Sold Jun 10, 2025

  • 2,412 Sq Ft
  • $1762/SF
  • 3 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1953

  161 E Floresta Way, Portola Valley, CA 94028

  Nestled in one of Ladera's most sought-after cul-de-sac locations, this updated split-level home offers the perfect blend of comfort, style, and functionality. This residence is ideal for modern living with three spacious bedrooms and three full bathrooms. A large living room features a lighted coffered ceiling, designer color palette, and custom-built-ins. Cooking is a snap in the chef's kitchen

  Rebecca Johnson Intero Real Estate Services

  161 E Floresta Way, Portola Valley, CA 94028
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  Est $4,388,196 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,768 Sq Ft

  635 Los Trancos Rd, Portola Valley, CA 94028

  635 Los Trancos Rd, Portola Valley, CA 94028
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  $5,495,000

  • 6 Beds
  • 5.5 Baths
  • 5,970 Sq Ft

  3 Oak Forest Ct, Portola Valley, CA 94028

  Positioned behind electronic gates at the end of a cul-de-sac with just four other homes, this architecturally significant home offers privacy, scale, & thoughtfully considered living on 1.354 acres. Spanning approximately 5,970 square feet of living space offering ample accommodations. Main level offers beautifully scaled rooms designed for entertaining & everyday comfort, flexible layout for

  Hugh Cornish Coldwell Banker Realty

  3 Oak Forest Ct, Portola Valley, CA 94028
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  /2

  $7,485,000 Sold Jun 04, 2025

  • 2,654 Sq Ft
  • $2820/SF
  • 61 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2015

  140 Pinon Dr, Portola Valley, CA 94028

  Contemporary masterpiece with spectacular Windy Hill views designed by architect Ana Williamson. Featuring steel I-beams, soaring ceilings create openness & strategically placed windows fill the space with light highlighting the natural setting. The modern open floor plan includes chef's kitchen with high-end appliances, custom Italian cabinetry & Dekton ceramic countertops. Floor to ceiling

  Julia Laquer Christie's International Real Estate Sereno

  140 Pinon Dr, Portola Valley, CA 94028
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  Est $3,330,743 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,068 Sq Ft

  141 Santa Maria Ave, Portola Valley, CA 94028

  141 Santa Maria Ave, Portola Valley, CA 94028
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  $6,998,000

  • 3 Beds
  • 2.5 Baths
  • 3,660 Sq Ft

  165 Golden Oak Dr, Portola Valley, CA 94028

  Welcome to this stunning home in Portola Valley, offering a perfect blend of comfort and elegance. With a generous living space of 4,088 sq ft situated on a 47,517 sq ft lot, this property provides ample room for relaxation and entertainment. The home features three spacious bedrooms, including a primary bedroom conveniently located on the ground floor, and two full bathrooms equipped with double

  Dana Cappiello Sotheby's Intl Rlty

  165 Golden Oak Dr, Portola Valley, CA 94028
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  $2,900,000 Sold Jun 03, 2025

  • 2,490 Sq Ft
  • $1165/SF
  • 110 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1960

  1 Hayfields Rd, Portola Valley, CA 94028

  Welcome to 1 Hayfields Road! Motivated Seller - best price on the flats of Portola Valley!!! Nestled in a serene and peaceful country setting, this inviting rancher offers the perfect balance of privacy and convenience. With stunning access to nearby trails, you can enjoy the natural beauty right outside your doorstep, whether you're hiking, biking, or simply soaking in the outdoors. Inside,

  Debora Smith Sotheby's Intl Rlty

  1 Hayfields Rd, Portola Valley, CA 94028
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  Est $5,920,627 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 4,472 Sq Ft

  4135 Alpine Rd, Portola Valley, CA 94028

  4135 Alpine Rd, Portola Valley, CA 94028
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  /40

  $4,695,000

  • 4 Beds
  • 4 Baths
  • 4,025 Sq Ft

  50 Bear Paw, Portola Valley, CA 94028

  This extraordinary Portola Valley Ranch property combines rare level land, breathtaking Windy Hill views from every floor, and a comprehensive whole-home remodel all on just over one-half acre. The homes thoughtful expansion and renovation, along with just completed interior and exterior painting and completely redone bamboo and hickory floors throughout, present a beautiful ambiance. With large

  Ginny Kavanaugh Coldwell Banker Realty

  50 Bear Paw, Portola Valley, CA 94028
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  /2

  $8,000,000 Sold May 29, 2025

  • 4,110 Sq Ft
  • $1946/SF
  • 13 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1981

  909 Westridge Dr, Portola Valley, CA 94028

  On the top of the hill at the end of a long private driveway and nestled on 3.5 mostly usable acres sits this very private home. Offering spectacular 270 degree views this 5 bedroom, 3 bath home sits on one of the finest sites in Portola Valley. The well-appointed private home features bright and light interiors with wonderful views throughout its effortless multi level design. The main level

  Peter Cowperthwaite Golden Gate Sotheby's International Realty

  909 Westridge Dr, Portola Valley, CA 94028
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  Est $4,009,718 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,015 Sq Ft

  45 Buckeye, Portola Valley, CA 94028

  45 Buckeye, Portola Valley, CA 94028
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  $5,999,000

  • 4 Beds
  • 3.5 Baths
  • 4,297 Sq Ft

  415 Golden Oak Dr, Portola Valley, CA 94028

  You wake up one morning on the deck of 415 Golden Oak Drive, coffee in hand, gazing at a view that makes time stand still. From this elevated perch in central Portola Valley, the South Bay unfolds rolling hills, morning mist, and the quiet promise of a perfect day. This beautifully updated 4-bedroom, 3.5-bath home offers ~3,700 sq. ft. of refined living space, blending clean architectural lines,

  Scott Hayes Compass

  415 Golden Oak Dr, Portola Valley, CA 94028
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  $5,000,000 Sold May 19, 2025

  • 3,074 Sq Ft
  • $1627/SF
  • 9 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1961

  831 La Mesa Dr, Portola Valley, CA 94028

  Step into this stunning single-level remodeled modern home nestled in the desirable Ladera neighborhood. Blending contemporary design with everyday comfort, this thoughtfully renovated home is the ultimate expression of California living. Dream chef's kitchen featuring a large center island, high-end appliances, custom cabinetry, & a walk-in pantry. This home has radiant heating, custom concrete

  Rebecca Johnson Intero Real Estate Services

  831 La Mesa Dr, Portola Valley, CA 94028
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  /25

  Est $3,081,642 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,940 Sq Ft

  15 Quail, Portola Valley, CA 94028

  15 Quail, Portola Valley, CA 94028
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  $4,995,000

  • 3 Beds
  • 5 Baths
  • 6,155 Sq Ft

  55 Vista Verde Way, Portola Valley, CA 94028

  Tucked away on approximately 2.77 acres in the Vista Verde community with easy access to the amenities of Portola Valley, this remarkable property offers a peaceful retreat from the fast-paced life of Silicon Valley. A sweeping tiled stairway descends through lushly planted gardens to the main entrance, where the home opens to grand yet understated interiors that echo the serenity and refinement

  Ginny Kavanaugh Coldwell Banker Realty

  55 Vista Verde Way, Portola Valley, CA 94028
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  /2

  $4,625,000 Sold May 12, 2025

  • 3,890 Sq Ft
  • $1189/SF
  • 52 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1981

  4 Franciscan Ridge, Portola Valley, CA 94028

  Portola Valley Ranch, the hidden gem of the Bay Area embodying the perfect combination of convenience and serenity. Located on 450 acres with 350 of those dedicated to open space with miles of hiking trails. Experience luxury living in this spacious 5-bedroom, 3.5 bath home with breathtaking views of the hills. Expansive windows, large skylights and multiple sliding doors create multi-directional

  Scott Chase Intero Real Estate Services

  4 Franciscan Ridge, Portola Valley, CA 94028
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  Est $3,232,921 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,130 Sq Ft

  10 Foxtail, Portola Valley, CA 94028

  10 Foxtail, Portola Valley, CA 94028
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  $5,995,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,420 Sq Ft

  4 Buck Meadow Dr, Portola Valley, CA 94028

  On nearly 2 acres in the prestigious Blue Oaks community, an enclave of custom homes surrounded by 217 acres of open space, this custom-built home showcases Mediterranean design and sweeping views from most rooms. Outside, the Terracotta clay tiled roof makes a striking first impression while inside, lofty ceilings, deep crown moldings, and floors in antique French tiles and fine oak exude

  Ginny Kavanaugh Coldwell Banker Realty

  4 Buck Meadow Dr, Portola Valley, CA 94028

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