San Mateo Homes with Cottage Style

Welcome to San Mateo County, a vibrant coastal gem nestled in the heart of California’s Bay Area. Known for its picturesque landscapes, diverse communities, and rich cultural heritage, San Mateo offers a unique blend of suburban charm and urban convenience. Among its many treasures is Daly City, a thriving city that boasts stunning views of the Pacific Ocean and is just a stone's throw away from San Francisco.

Daly City is renowned for its welcoming neighborhoods, making it an ideal place for families, young professionals, and retirees alike. One of the most enchanting features of this area is its collection of charming cottage-style homes. These delightful residences exude warmth and character, often showcasing quaint architecture, lush gardens, and inviting front porches that beckon you to relax and unwind.

Cottage-style homes in Daly City are perfect for those seeking a cozy, intimate atmosphere. With their unique layouts and cozy interiors, these homes often feature vintage details, such as hardwood floors, built-in bookshelves, and decorative moldings. Many of these properties also offer outdoor spaces perfect for gardening, entertaining, or simply enjoying the mild California weather.

Living in Daly City means being part of a vibrant community with access to excellent schools, parks, and a variety of shopping and dining options. Plus, with easy access to public transportation and major highways, residents can effortlessly explore all that the Bay Area has to offer.

If you’re dreaming of a home that combines charm, comfort, and convenience, look no further than the delightful cottage-style homes in Daly City, San Mateo County. Your perfect retreat awaits!

Newest San Mateo Homes with Cottage Style

$1,050,000

3 Beds ⋅ 2 Baths ⋅ ML82055234 MLS

This updated stylish home in the Questa La Honda Guild features a quiet location at the end of Recreation Drive. The Beautiful hardwood floors, updated kitchen and baths plus large patio with hot tub make this a perfect retreat. The large parcel creates the feeling of being all alone, yet convenient to the amenities of pool, tennis court, riding ring and Club House. Lots of hiking and riding trails nearby are available right outside the door. The hardwood floors are gleaming and the double pane windows help provide great climate control. The breakfast nook and the eat-in counter are attractive and the rear patio also provides dining options.

11 Recreation Drive, La Honda

Listing courtesy of Patrick Ryan from Compass. 650-759-2430

$1,698,000

2 Beds ⋅ 2 Baths ⋅ ML82054580 MLS

On the market for the first time in 56 years, this 1936 vintage home in Woodside Acres, sits on a generous corner lot zoned R20000, offering a world of possibilities. Development Potential: Home expansion, create a duplex, or add an ADU. Prime Location: Midway between San Francisco and San Jose; central to Fortune 100 tech giants. Rare Opportunity: A vintage gem ready for its next chapter. Buyer to investigate to their own satisfaction. Behind flowering trees and a gated driveway is an eclectic farmhouse facade with archways, a tile walkway and an enclosed front porch. Old World charm begins at the front door with vintage light fixtures, crystal doorknobs, wall niches, picture railings, and timeless hardwood floors. Surprisingly spacious, the layout features a sunlit living room with fireplace and amber glass light fixtures, a family/dining room with parquet floor and wood stove, and a modernized kitchen with newly painted cabinets, appliances and a breakfast room with built-in buffet. Two bedrooms (including a suite), two baths, and a private office with garage access, complete the interior. Landscaped grounds include patios, lush lawns, colorful blooms, and fruit trees.

1585 Union Avenue, Redwood City

Listing courtesy of Julie Baumann from Compass. 650-576-8889

$2,595,000

2 Beds ⋅ 1 Baths ⋅ ML82052857 MLS

Beautiful (Bonita!) very large property in upper Los Trancos Woods. Over 1.6 AC of mostly flat land with old, mostly not habitable House, Cottage, Garage and Carport, comfortably spread throughout the property. In Feb 2026, San Mateo County approved a 2 lot subdivision, and work is ongoing to complete the final map recording. The house is available prior to recording of the subdivision as a single lot for buyers who might want more flexibility in what they do with the property. Extensive geological, geotechnical, arborist, historical, biological and civil reports and plans come with the property.

245 Bonita Road, Portola Valley

Listing courtesy of Mike Sokolsky from Coldwell Banker Realty. 650-465-2573

$1,290,000

3 Beds ⋅ 2 Baths ⋅ ML82052395 MLS

Above the gentle curve of the San Gregorio Creek with its own private beach, this rare and useable 3-acre property offers a peaceful retreat minutes from the center of La Honda. The home features timeless charm with its wrap-around porch, fireplace, and views of the soaring redwoods. A flexible floor plan includes three sleeping areas and a bonus room. The attached two-car garage includes EV charging capability, back-up generator and an upstairs workshop with plenty of storage. Super opportunity to use as either a full-time residence or weekend escape. Rich in history, once the site of The Big Tree Inn, the home retains its timeless charm while benefiting from key updates including an upgraded foundation, updated electrical, septic, and a private well. Adjacent to the home an open, flat meadow, framed by evergreen trees, presents exceptional possibilities. How will you enjoy this? Garden, farm, keep animals, add outbuildings, the opportunities are amazing. Additional features include water rights, and rustic bridge access to the property, creating a truly distinctive setting that feels worlds away while remaining within reach of modern conveniences.

6975 La Honda Road, La Honda

Listing courtesy of Kimberly Hansen from Golden Gate Sotheby's International Realty. 415-806-8230

$999,995

4 Beds ⋅ 2 Baths ⋅ ML82051065 MLS

Welcome to your mountain oasis at 306 Scenic Dr, La Honda! Nestled in the Cuesta La Honda Guild, this property blends rustic charm with unmatched layout flexibility. The main home features an updated kitchen with stainless appliances and gorgeous hill views. Escape to the upstairs main suite, boasting a spacious sitting area and an ultra-private rooftop deck. Another bedroom includes a fun ~3ft play loft, perfect for a kids' secret fort. This property truly stands out with two independent bonus spaces separate from the main level. First is a separate-entrance downstairs suite of about 430 sq ft, complete with its own cozy living room, bedroom, and laundry. Second is a detached 232 sq ft guest cottage, ideal for visitors, an art studio, or a remote office. Outdoor living thrives here with multiple view decks, a private hot tub, a beautiful garden, a chicken coop, a storage shed, and a 2-car carport. Enjoy resort-style living with exclusive Guild amenities, including 400+ acres of open space with hiking and biking trails, a community pool, tennis courts, a clubhouse, a playground, and a scenic pond. Ideal for multi-generational living or a private retreat, this slice of paradise won't last long. Specs: 3BD/2BA main layout plus the 430 sq ft lower suite and 232 sq ft cottage.

306 Scenic Drive, La Honda

Listing courtesy of Scott Hayes from Compass. 650-245-5044

$1,350,000

4 Beds ⋅ 3 Baths ⋅ ML82048182 MLS

Must See!! Rustic Log cabin + bonus structures in the historic Middleton Tract neighborhood - which sits along Portola Valley Redwoods State Park, Skyline Ridge Open Space & Russian Ridge Open Space Preserves - offer a lucrative investment into a slice of Silicon Valley History. More than just an escape from the city, enjoy incredible wildlife viewing, privacy among towering redwoods & exclusive access to Peter's creek trailhead. The main cabin, built from redwood milled onsite and lovingly restored in 2006, offers 2 bedrooms, 2 full bathrooms, impressive vaulted ceilings and an open living room with fireplace. Enjoy the 1,100+ sqft tiered deck with a BBQ area taking in redwood views. The kitchen is well equipped with SS appliances, Viking Gas Range, skylights, and plenty of storage. There is also an additional sleeping cottage, separate 2 bedroom sleeping loft with kitchenette, mediation room and school house. Room for RV parking as well. Starlink Internet keeps you connected with reliability thru winter storms. 13 miles to Alice's restaurant,18 miles to Stanford University. Less than 25 miles to Silicon Valley hubs such as Mountain View & Palo Alto. 28 miles to the beach & numerous iconic hiking + biking opportunities out your back door! More photos to come.

41 Back Road, La Honda

Listing courtesy of from Room Real Estate. 831-234-6683

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