Sugarloaf, CA homes for sale & real estate

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OPEN TODAY, 2PM TO 4PM3D WALKTHROUGH

254 41st Ave, San Mateo, CA 94403
254 41st Ave, San Mateo, CA 94403
254 41st Ave, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
Commanding arguably the most extraordinary unobstructed bay views in all of San Mateo, this magnificent 4BR/4BA residence has been impeccably renovated to deliver a 3,580± SF immersive living experience where floor-to-ceiling vistas meet architectural sophistication. Plank and beam ceilings, oak floors, and refined moldings complement double-pane windows, skylights, and recessed lighting, illuminating integrated living spaces that flow onto a sprawling deck. Blending the warmth of natural wood with the elegance of stone, the chefs kitchen features granite countertops, custom cabinetry, premium appliances, a wine fridge, and a striking breakfast bar. Offering peaceful separation from

$2,998,000

4 beds4 baths3,580 sq ft

254 41st Ave, San Mateo, CA 94403

6,135 sq ft lot • 2 garage spots • Very walkable

NEW 14 HRS AGO

4111 Beresford St, San Mateo, CA 94403
4111 Beresford St, San Mateo, CA 94403
4111 Beresford St, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
Fantastic investment property in ideal Peninsula location. Six large one bedroom, one bath units. New roof, exterior paint, and landscaping. Easy property to manage and lease. Great upside. Approximately 7,500 sq ft property on a 4,885 sq ft lot. Three garage spaces. Great west side San Mateo asset with easy access to Caltrain, Freeways, and SamTrans. Separate PG & E and water meters.

$2,899,000

6 beds— baths7,505 sq ft

4111 Beresford St, San Mateo, CA 94403

4,885 sq ft lot • Very walkable

OPEN TODAY, 1PM TO 4PM3D WALKTHROUGH

1647 Overland Dr, San Mateo, CA 94403
1647 Overland Dr, San Mateo, CA 94403
1647 Overland Dr, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
Sunrise Views Over a Backyard Wonderland. In this friendly pocket of San Mateo's Laurelwood neighborhood, 1647 Overland surprises with her understated, manicured street presence and rather serious front door that when open, reveals a home spilling over with warmth and fun. Living spaces are open and comfortable and a remarkable family room/kitchen organizes daily and entertains easily with its flow to the deck and backyard. Four large bedrooms on one level include a private primary suite and one currently finished as a home office. The home's high ceilings, natural flow between spacious rooms, generous closets and storage, and attached two-car garage were designed for modern functionality,

$3,250,000

4 beds2.5 baths2,545 sq ft

1647 Overland Dr, San Mateo, CA 94403

7,629 sq ft lot • 2 garage spots • Pool

OPEN SUN, 2PM TO 4PM

308 42nd Ave, San Mateo, CA 94403
308 42nd Ave, San Mateo, CA 94403
308 42nd Ave, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
Stunning Westwood Knolls home with panoramic bay views from nearly every room. A 53-foot-wide composite deck with cable railings and gas/electric outlets spans the back -- ideal for entertaining. The upper level features vaulted ceilings, large windows, engineered maple floors, and an open living and dining area. The family room includes a gas/electric fireplace, built-in cabinetry, and sliding doors to the deck. The kitchen offers granite counters, stainless steel appliances, and a breakfast bar. The en-suite primary has ample closet space and a modern bath with double vanity and walk-in shower. A powder room is near the foyer. The lower level includes 3 bedrooms, a full bath, a 1,000-bott

$2,298,000

4 beds2.5 baths2,780 sq ft

308 42nd Ave, San Mateo, CA 94403

9,177 sq ft lot • 2 garage spots • Somewhat walkable

OPEN TODAY, 2PM TO 4PM

1401 Woodberry Ave, San Mateo, CA 94403
1401 Woodberry Ave, San Mateo, CA 94403
1401 Woodberry Ave, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
A rare and exceptional opportunity to get two properties on one lot. 1401 Woodberry Avenue is a two-bedroom, two-bath home with spacious yard and two- car garage. Enjoy the outdoor space and manicured yard year-round. 3400 Glendora is a three- bedroom, two- bath home with a sun-filled patio and spacious living room. Enjoy easy access to Laurelwood Shopping Center, parks and open space - all just steps from your front door. Easy access to shopping, restaurants, and freeways make this a wonderful place to call home. Rental income or multi-generational living are just a few options for the owner of this unique property. Property Highlights: Home #1 3 Bedrooms / 2 Bathrooms Comfortable, well-p

$2,595,000

5 beds4 baths3,790 sq ft

1401 Woodberry Ave, San Mateo, CA 94403

9,150 sq ft lot • 2 garage spots • Somewhat walkable

Property at 700 Laurelwood Dr, San Mateo, CA 94403, 3 beds, 2.5 baths

$3,200,000

3 beds2.5 baths2,610 sq ft

700 Laurelwood Dr, San Mateo, CA 94403

Property at 632 W 39th Ave, San Mateo, CA 94403, 3 beds, 1.5 baths

$1,988,888

3 beds1.5 baths1,480 sq ft

632 W 39th Ave, San Mateo, CA 94403

Property at 3709 Kenwood Ave, San Mateo, CA 94403, 4 beds, 2.5 baths

$2,888,000

4 beds2.5 baths2,213 sq ft

3709 Kenwood Ave, San Mateo, CA 94403

Property at 1406 Cedarwood Dr, San Mateo, CA 94403, 4 beds, 2.5 baths

$2,488,000

4 beds2.5 baths2,440 sq ft

1406 Cedarwood Dr, San Mateo, CA 94403

Property at 417 36th Ave, San Mateo, CA 94403, 3 beds, 2 baths

$2,300,000

3 beds2 baths2,300 sq ft

417 36th Ave, San Mateo, CA 94403

Property at 112 42nd Ave, San Mateo, CA 94403, 3 beds, 2 baths

$1,900,000

3 beds2 baths2,728 sq ft

112 42nd Ave, San Mateo, CA 94403

Property at 3708 S El Camino Real, San Mateo, CA 94403, 4 beds, 6 baths

$3,498,000

4 beds6 baths7,915 sq ft

3708 S El Camino Real, San Mateo, CA 94403

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Nearby homes that match your criteria

NEW 9 HRS AGO

2464 Willow Way, San Mateo, CA 94403
2464 Willow Way, San Mateo, CA 94403
2464 Willow Way, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
This spacious Plan 1 residence is upgraded throughout and is a must-see. The gourmet kitchen includes upgraded cabinets and countertops and is an ideal home for entertaining family and friends. The incredible layout affords a one-of-a-kind lifestyle.

$3,054,817

4 beds3.5 baths2,565 sq ft

2464 Willow Way, San Mateo, CA 94403

2,132 sq ft lot • $252 HOA • 2 garage spots

NEW 10 HRS AGO

2305 Red Oak Ct, San Mateo, CA 94403
2305 Red Oak Ct, San Mateo, CA 94403
2305 Red Oak Ct, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
This spacious Plan A residence is upgraded throughout and is a must-see! The gourmet kitchen includes upgraded cabinets and countertops and is an ideal home for entertaining family and friends. The incredible layout affords a one-of-a-kind lifestyle.

$2,295,629

4 beds5.5 baths2,150 sq ft

2305 Red Oak Ct, San Mateo, CA 94403

1,613 sq ft lot • $519 HOA • 2 garage spots

NEW 10 HRS AGO

2434 Willow Way, San Mateo, CA 94403
2434 Willow Way, San Mateo, CA 94403
2434 Willow Way, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
This spacious Plan C residence is upgraded throughout and is a must-see! The gourmet kitchen includes upgraded cabinets and countertops and is an ideal home for entertaining family and friends. The incredible layout affords a one-of-a-kind lifestyle.

$1,779,177

3 beds3 baths1,571 sq ft

2434 Willow Way, San Mateo, CA 94403

1,609 sq ft lot • $519 HOA • 2 garage spots

OPEN TODAY, 1PM TO 4PM3D & VIDEO TOUR

300 Davey Glen Rd #3928, Belmont, CA 94002
300 Davey Glen Rd #3928, Belmont, CA 94002
300 Davey Glen Rd #3928, Belmont, CA 94002
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
Top-Floor Unit, City Views, Fully Renovated, Belmont Schools, Resort-Style Living, this beautifully remodeled top-floor condo has it all! Roof deck level w/ sweeping city views & abundant natural light. This move-in-ready home blends modern upgrades w/ resort-style amenities. New flooring and light fixtures throughout, along w/ a spacious, light-filled layout. The updated kitchen features brand-new SST appliances, quartz countertops, and a stylish sinkideal for any home chef. Just off the kitchen is a formal dining area that flows seamlessly into the bright & expansive living room. Step out onto your private deck to enjoy peaceful city views. The spacious bedroom includes a larg

$474,999

1 bed1 bath722 sq ft

300 Davey Glen Rd #3928, Belmont, CA 94002

$500 HOA • Garage • Community pool

OPEN TODAY, 1PM TO 4PM

408 W Hillsdale Blvd, San Mateo, CA 94403
408 W Hillsdale Blvd, San Mateo, CA 94403
408 W Hillsdale Blvd, San Mateo, CA 94403
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
Welcome to 408 W Hillsdale Blvd! Upon entry, you're immediately drawn into a spacious, light-filled living area where floor-to-ceiling sliding doors frame the backyard and create a seamless indoor-outdoor flow, perfect for relaxed living. The open-concept living and dining spaces offer a warm, inviting atmosphere ideal for both everyday comfort and entertaining, while the kitchen features generous cabinetry and expansive counter space, providing plenty of room to prep, cook, and gather. Down the hall are three well-sized bedrooms, including a comfortable primary suite with direct access to the backyard, an ideal retreat for morning coffee or winding down at the end of the day. Located just

$1,898,000

3 beds2 baths1,690 sq ft

408 W Hillsdale Blvd, San Mateo, CA 94403

7,390 sq ft lot • 2 garage spots • Very walkable

OPEN TODAY, 1PM TO 4PM3D & VIDEO TOUR

2185 Cobblehill Pl, San Mateo, CA 94402
2185 Cobblehill Pl, San Mateo, CA 94402
2185 Cobblehill Pl, San Mateo, CA 94402
ABOUT THIS HOME
Sugarloaf, CA Homes for Sale
Discover the perfect blend of luxury, comfort, & California living at 2185 Cobblehill Place, nestled in the highly sought-after Highlands neighborhood of San Mateo. Situated on a sprawling 17,997 sq ft lot, this beautifully crafted home features 4 bedrooms, 3.5 bathrooms, & 3,390 sq ft of thoughtfully designed living space. Expansive picture windows in the light-filled living & dining areas frame stunning panoramic views, while the open-concept kitchen offers a large center island, breakfast bar, walk-in pantry & premium finishes. The kitchen seamlessly flows into a spacious family room with a fireplace & breathtaking vistas-ideal for relaxing or entertaining. Th

$4,499,000

4 beds3.5 baths3,390 sq ft

2185 Cobblehill Pl, San Mateo, CA 94402

0.41 acre lot • 2 garage spots • Car-dependent

Property at 643 28th Ave, San Mateo, CA 94403, 4 beds, 3 baths

$2,698,000

4 beds3 baths2,470 sq ft

643 28th Ave, San Mateo, CA 94403

Property at 4111 George Ave #3, San Mateo, CA 94403, 1 bed, 1 bath

$620,000

1 bed1 bath840 sq ft

4111 George Ave #3, San Mateo, CA 94403

Property at 826 W Hillsdale Blvd, San Mateo, CA 94403, 4 beds, 2 baths

$2,249,000

4 beds2 baths2,150 sq ft

826 W Hillsdale Blvd, San Mateo, CA 94403

Property at 2186 Carlmont Dr, Belmont, CA 94002, 12 beds, 10 baths

$4,300,000

12 beds10 baths9,688 sq ft

2186 Carlmont Dr, Belmont, CA 94002

Property at 2432 Willow Way #0811, San Mateo, CA 94403, 2 beds, 2.5 baths

$1,833,265

2 beds2.5 baths1,676 sq ft

2432 Willow Way #0811, San Mateo, CA 94403

Property at 800 26th Ave, San Mateo, CA 94403, 3 beds, 2.5 baths

$3,100,000

3 beds2.5 baths2,940 sq ft

800 26th Ave, San Mateo, CA 94403

Property at 14 Arroyo View Cir, Belmont, CA 94002, 3 beds, 2.5 baths

$1,789,000

3 beds2.5 baths1,520 sq ft

14 Arroyo View Cir, Belmont, CA 94002

Property at 2506 Sage St, San Mateo, CA 94403, 2 beds, 3 baths

$2,773,762

2 beds3 baths2,300 sq ft

2506 Sage St, San Mateo, CA 94403

Property at 2821 Monte Cresta Dr, Belmont, CA 94002, 5 beds, 5 baths

$3,750,000

5 beds5 baths2,740 sq ft

2821 Monte Cresta Dr, Belmont, CA 94002

Property at 58 Laurie Meadows Dr #3, San Mateo, CA 94403, 2 beds, 2 baths

$799,000

2 beds2 baths1,040 sq ft

58 Laurie Meadows Dr #3, San Mateo, CA 94403

Property at 1735 Terrace Dr, Belmont, CA 94002, 5 beds, 4 baths

$2,799,000

5 beds4 baths2,800 sq ft

1735 Terrace Dr, Belmont, CA 94002

Property at 1245 Chula Vista Dr, Belmont, CA 94002, 4 beds, 2 baths

$2,599,888

4 beds2 baths2,910 sq ft

1245 Chula Vista Dr, Belmont, CA 94002

Property at 138 Rosewood Ln, San Mateo, CA 94402

$3,395,000

— beds— baths— sq ft

138 Rosewood Ln, San Mateo, CA 94402

Property at 128 Rosewood Ln, San Mateo, CA 94402

$3,395,000

— beds— baths— sq ft

128 Rosewood Ln, San Mateo, CA 94402

Average home prices near Sugarloaf, CA

Cities

Neighborhoods

Bay Meadows homes for sale
$1,831,500
Fiesta Gardens homes for sale
$1,490,000
Hayward Park homes for sale
$1,100,000
Hillsdale homes for sale
$1,490,000
Redwood Shores homes for sale
$1,230,000
Baywood homes for sale
$1,480,000
Hacienda homes for sale
$899,000
Sunnybrae homes for sale
$1,600,000
San Mateo Park homes for sale
$6,598,000
Aragon / Baywood homes for sale
$1,750,000

Sugarloaf, CA real estate trends

All Home Types trends in Sugarloaf, CA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$2,134,250

-0.69% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

Sugarloaf, CA

$2,134,250

-0.69%

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