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20851 Assiniboine TRL, Los Gatos
$887,000
2 Beds ⋅ 2 Baths ⋅ ML82048722 MLS ⋅ Chemeketa Park BLDG.
Retreat in the Hills of Los Gatos, charming Mountain Home with Custom-Built Cabin Escape to this peaceful, wooded Los Gatos hills home mountain living with Silicon Valley convenience. The living room features new windows opening to a sunny deck with forest views. The gourmet kitchen boasts custom cabinetry, center island, new LG appliances with double oven, gas range, and walk-in pantry with washer/dryer. Primary suite offers walk-in closet and tiled shower. One additional bedroom and a flex for family, guests, or office. Outside, a restored 121 sq ft custom cabin suits guests, studio, gym, or home office. Deck overlooks Los Gatos Creek with under-deck storage. Recent Improvements: New flooring, Expanded windows, New roof, Kitchen remodel, Furnace, Water heater, Electrical panel & gateway, 2 Tesla Powerwalls, 220V EV charger, Landscape lighting, Retention walls, Refurbished cabin Community: playground, garden & clubhouse with hikes and events. Location 6 min to Lexington Elementary (IB World School) Feeds Fisher Middle & Los Gatos High, Hwy 17 access, Minutes to downtown, Lexington Reservoir & redwood trails, 2 fire stations nearby (incl. S-70i Firehawk) Ideal for families, remote workers, or anyone craving mountain charm near the Bay Area. Book a showing today.

20851 Assiniboine TRL, Los Gatos

Listed by Dan Hunnicutt, 650-704-5628 from eXp Realty of Northern California, Inc.
(If provided) CoList: from

Sold listing courtesy of Dan Hunnicutt from HC44P
18165 Santa Ana RD, Los Gatos
$875,000
2 Beds ⋅ 3 Baths ⋅ ML82030773 MLS ⋅ Redwood Estates BLDG.
Welcome to your new home in Los Gatos! Located in the highly desired community of Redwood Estates, just minutes to Silicon Valley and Santa Cruz beaches. Top Los Gatos schools. Lot size includes 3 adjacent parcels totaling over 1 acre. 2nd floor area was converted into living space which includes a the 2nd full bath, bedroom, and office area which could be converted into a 3rd bedroom. This brings the total living area to +/- 2000 sq ft. Full basement offers an excellent workshop, fitness center, storage area, or possibly even an ADU. Redwood Estates is a FireWise community which qualifies for a discount on fire insurance. Navigation is incorrect. Waze will get you there. Or just follow the main road through Redwood Estates and you will see the real estate sign.

18165 Santa Ana RD, Los Gatos

Listed by Michael Scherer, 408-353-6453 from Cruz Properties
(If provided) CoList: from

Sold listing courtesy of Michael Scherer from CRUZP
30100 Mount Madonna RD, Los Gatos
$850,000
ML82046112 MLS
Pending Private Sale

30100 Mount Madonna RD, Los Gatos

Listed by Brian Beck, 408-927-9782 from Brian R Beck, Broker
(If provided) CoList: from

Sold listing courtesy of Un Represented from NOBUY
21590 Madrone DR, Los Gatos
$840,000
2 Beds ⋅ 2 Baths ⋅ ML82052618 MLS ⋅ Redwood Estates Services Associa BLDG.
Charming and Sought After Redwood Estates Cottage! This 2-bedroom, 2-bath home offers approximately 1150 sq ft of living space on a 5,850 sq ft lot. Enter to high ceilings, sunny space with skylights, windows, patio sliders and french doors throughout providing ambient light. Wide plank wooden flooring in living room combine with kitchen. The kitchen is equipped with tile countertops, a gas cooktop and oven range, dishwasher, refrigerator, and exhaust fan and eat-in bar. Spacious deck off of kitchen for relaxing under the lovely mountain views. Primary bedroom with carpeting and ceiling fan and a full bathroom with a shower over tub are on the upper floor. Spiral staircase leads to lower level with 2 adjoining rooms for den plus bedroom combo and full bathroom along with large basement storage space. Step outside where your hot tub awaits amongst the garden space. Laundry is conveniently situated in the utility room with 220V electricity hookup and washer/dryer included. Central heat and wired for generator. Friendly community with pool, playgrounds, community center, new fire station, Pizza restaurant, post office and general store in a great commute location 7 minutes to town. Great Los Gatos Schools: Lexington Elem, Fisher Middle, Los Gatos High

21590 Madrone DR, Los Gatos

Listed by Lisa Sgarlato, 408-396-7231 from Compass
(If provided) CoList: from

Sold listing courtesy of Margaret Barr from M5044
21683 Summit RD, Los Gatos
$780,000
2 Beds ⋅ 1 Baths ⋅ ML82013176 MLS ⋅ Redwood Estates BLDG.
Amazing opportunity to own a single family home with great schools, Los Gatos address, privacy, and style! Beautifully remodeled and move-in ready. You'll enjoy new natural colored flooring throughout, a brand new kitchen with chic finishes complete with an island for cooking and entertaining. All new bathroom just waiting for its new owner. Incredibly convenient location with NO windy roads and a quick 9 minute drive to vibrant downtown Los Gatos. Unwind at the end of day on your wood deck overlooking trees. You will appreciate the hard work of almost all recently installed dual pane windows and fresh exterior and interior paint, and new roof! Don't miss the indoor laundry and 2-car garage! Being part of Redwoods Estates, residents enjoy 2 community parks, sparkling pool, and benefits of the pavilion plus nearby pizza and bbq restaurant and convenience store. Top-rated Los Gatos schools. You could buy a townhome with high dues, but why when you have so much more here with a low-maintenance property! Sale is subject to CA Civil Code 2924 m/o.

21683 Summit RD, Los Gatos

Listed by Angele Price, 408-605-3005 from Compass
(If provided) CoList: from

Sold listing courtesy of Janelle Boyenga from COMPS
18065 Soda Springs RD, Los Gatos
$751,000
2 Beds ⋅ 1 Baths ⋅ ML82022594 MLS
18065 Soda Springs Road offers a rare combination of privacy, charm, and potential. Set on a 0.72-acre hillside lot surrounded by mature trees, this 1950-built home features two bedrooms, one bath, a large screen room (not included in the square footage), a 1-car garage, and approximately 1,008 square feet of comfortable living space. The peaceful natural setting provides a sense of retreat while remaining within easy reach of downtown Los Gatos and Silicon Valley. Large windows invite natural light and views of the surrounding hills, blending indoor comfort with outdoor serenity. Ideal as a primary residence, weekend getaway, or investment opportunity, short or long term rental. The propertys generous lot allows room for gardens and includes an expansive deck in the rear of the house. This unique and private estate offers tranquility, character, and room to personalize, capturing the essence of relaxed Los Gatos mountain living.

18065 Soda Springs RD, Los Gatos

Listed by Jim Mauldwin, 408-482-0992 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Dana Juncker from COMPS
17944 Madrone DR, Los Gatos
$720,000
2 Beds ⋅ 1 Baths ⋅ ML82024547 MLS ⋅ Redwood Estates Services Assoc. BLDG.
Priced to Sell!! Award winning Los Gatos Schools. This Home is located in the desirable Redwood Estates community and features 1296 square feet of living space, two bedrooms and an updated bathroom with dual vanity with quartz countertop, and laundry area. An open and spacious living area with gorgeous nature views, kitchen with an island and repainted cabinets and a work from home office space and/or bonus room. The exterior decks offer the perfect space for lounging and entertaining, all newly repainted decks. The community offers a pool Event Center and kids playground and green space all surrounded by beautiful trees and natural surroundings enjoy easy access to Hwy 17 and Old Santa Cruz Highway as well as downtown Los Gatos and Santa Cruz beaches. Redwood Estates Service Association is NOT an HOA. It is a California non-profit, mutual benefit corporation (501C-12). It does not control what you can do with your property. It maintains the roads, culverts. pool, community center, parks, signage and more.

17944 Madrone DR, Los Gatos

Listed by Robin Wickman, 408-505-6144 from BRG Realty
(If provided) CoList: from

Sold listing courtesy of Reshma Sait from REEB
17960 Apache TRL, Los Gatos
$710,000
3 Beds ⋅ 2 Baths ⋅ ML82040835 MLS ⋅ Chemeketa Park BLDG.
Beautiful Swiss Chalet-style home nestled amongst the great redwoods of the Santa Cruz Mountains, in the Chemeketa Park community, offers a warm woodland retreat. Only a five-minute drive to Downtown Los Gatos, this 1,450sqft home has 3.5 bedrooms, two bathrooms, and a reverse floorplan; the living area is on the second floor. It also features stunning bamboo floors, skylights, floor to ceiling windows, vaulted ceilings, and a newly remodeled kitchen with new GE appliances and granite counter tops. Terraced backyard, indoor laundry/utility room, four off-street parking spaces, Los Gatos Schools, and Chemeketa Clubhouse association. Multiple porches and decks surround the property inviting you to breath in the views. Natural water from creek, provided by private water company. Excellent opportunity for an investor contractor. Looking for an ALL-CASH offer.

17960 Apache TRL, Los Gatos

Listed by Melissa Lynch, 408-839-3580 from Galway Real Estate & Management
(If provided) CoList: from

Sold listing courtesy of Mihaela Sultan Encizo from OBBCR
17741 Comanche Trl, Los Gatos
$710,000
1 Beds ⋅ 1 Baths ⋅ BE41124177 MLS
Impeccably maintained cottage in Chemeketa Park! Home is located near the community garden, clubhouse and playground. Remodeled kitchen with quartz countertops with granite effect and bathroom remodeled with ceramic tile floors with in-floor radiant heat. A wood-burning stove with an exterior intake will efficiently heat the entire house. Dual-pane windows. Several sun tunnels and large windows bring tons of natural light. Additional detached building offers additional storage for bikes, gardening tools, etc. Google maps says drive time from home to downtown Los Gatos is 10 minutes. Highly sought after Los Gatos School District: Lexington Elementary School, Fisher Middle School, and Los Gatos High School. This is a perfect little gem of a house. It is super adorable, well laid out, well-appointed, and in a fantastic location. You MUST see this in person to really appreciate this property. The photos do not do it justice!

17741 Comanche Trl, Los Gatos

Listed by Vivian Ho, (510) 882-6377 from EXP Realty of California, Inc
(If provided) CoList: Kevin Bui from eXp Realty of California

Sold listing courtesy of Terel Beppu from SIDE
20841 Comanche TRL, Los Gatos
$490,000
2 Beds ⋅ 1 Baths ⋅ ML82019232 MLS ⋅ Chemeketa Park BLDG.
Updated mountain cabin just minutes to Silicon Valley! Charming home featuring laminate wood flooring, propane forced-air heating, tankless water heater, stainless steel range and refrigerator, and indoor washer/dryer hookups. The bathroom includes radiant heated floors for extra comfort. Enjoy cozy winter evenings by the wood stove and sunny afternoons on the deck. An additional room off the living area offers flexibility for a small bedroom, office, or hobby space. The property also includes a garage with workshop/storage area. Located in the friendly Chemeketa Park community with access to a playground and clubhouse nearby. Perfect for first-time buyers, those looking to downsize, or as an income-producing rental. Chemeketa Park maintains its own private water company and roads. This is not an HOA. Dues, including water, are approximately $200 per month.

20841 Comanche TRL, Los Gatos

Listed by Michael Scherer, 408-353-6453 from Cruz Properties
(If provided) CoList: from

Sold listing courtesy of Brielle Bariteau from S1241
21749 Summit RD, Los Gatos
$373,000
ML82025279 MLS
Rare opportunity to purchase 2 adjacent undeveloped lots on Summit Rd, just 1 mile from Hwy 17, 10-12minutes from downtown Los Gatos. 2 APNS totaling over 1.13 acres = 40,000 SF APN 544-48-098 + 9,391 SF APN 544-48-110. List price is for BOTH APNs! Seller prefers to sell the lots together but they may be developed or resold separately. Buyer to investigate possibilities for lot line adjustment. Lots of upside here, there are many high end homes and estates along Summit Rd. This is very usable oak-studded land, with a huge level area off Summit, sloping gently down to Virdelle and adjacent Good Neighbor Park. 260-270 ft frontage on both streets. San Jose Water in the street, PG&E power pole on the property, Comcast available. Septic will be required (no investigations done). Redwood Estates offers the 'Pavilion at Redwood Estates' event venue, USPS Post Office, Redwood Store, popular Pizzeria Vittoria (formerly Nonnos), 2 community parks, swimming pool, and Redwood Fire Station. Redwood Estates is a Firewise USA Community. Award winning Los Gatos schools - Lexington Elementary, Fisher Middle, Los Gatos High! Lexington Elementary is the only school in the LGUSD offering the International Baccalaureate Primary Years & Early Years TK programs.

21749 Summit RD, Los Gatos

Listed by Rebecca Smith, 408-507-7165 from Christie's International Real Estate Sereno
(If provided) CoList: Karen Izzo from Christie's International Real Estate Sereno

Sold listing courtesy of David Holmes from OBOPACU 01
0 Idylwild, Los Gatos
$365,000
ML82050466 MLS
2 merged lots APNS 558-37-041 and 042 available for purchase with home at 18355 Idylwild Road at this time.

0 Idylwild, Los Gatos

Listed by Lisa Sgarlato, 408-396-7231 from Compass
(If provided) CoList: from

Sold listing courtesy of Un Represented from NOBUY
21565 Alma CT, Los Gatos
$355,000
3 Beds ⋅ 1 Baths ⋅ ML82039156 MLS
Opportunity knocks in the heart of Redwood Estates! This 3-bedroom, 1-bath home sits on a sunny double lot, totaling approximately 0.46 acres (0.27 acres + 0.19 acres), surrounded by towering redwoods and serene forest views. Its your chance to craft the home of your dreams and build equity with a little vision and elbow grease. Beyond the charm of the natural surroundings, this property offers the ultimate combination of tranquility and convenience. Located within the highly regarded Los Gatos School District featuring Lexington Elementary, Fisher Middle, and Los Gatos High. Plus, youre just a quick commute to Los Gatos and San Jose, making it perfect for those who want the best of both worlds: peaceful retreat and city accessibility. Whether youre looking to renovate, rebuild, or reimagine, this property is brimming with potential. Dont miss this rare opportunity to create something truly special in a coveted location!

21565 Alma CT, Los Gatos

Listed by Thomas Mendoza, 831-435-8518 from Compass
(If provided) CoList: from

Sold listing courtesy of Lisa Sgarlato from COMPS
28860 Loma Chiquita RD, Los Gatos
$296,820
1 Beds ⋅ 2 Baths ⋅ ML82036881 MLS
Private retreat in the Los Gatos Mountains. This owner-built mountain cabin, constructed in 1985, sits on 10 serene acres offering peace, privacy, and stunning long-range views. The property features ample usable land with plenty of space for parking vehicles, recreational equipment, or the potential to build an additional cabin (buyer to verify). private well, 8,000 gallons of water storage, The main living space offers an open-concept kitchen, dining area, and living room plus a full bathroom. Cabin has a spacious primary bedroom with a large closet and an additional full bath. Vaulted ceilings create an airy feel and offer potential for loft areas. Enjoy beautiful natural surroundings without sacrificing connectivity with good internet and cell phone coverage. Access is primarily via Highway 17 and Summit Road, followed by an approximate 35-minute drive on an unimproved road that is passable year-round. Alternate access is available via a dirt road off Croy Road in Morgan Hill. This is a private, hard-to-find property, no drive-bys, Cash sale only; property will not qualify for conventional or FHA financing.

28860 Loma Chiquita RD, Los Gatos

Listed by Michael Scherer, 408-353-6453 from Cruz Properties
(If provided) CoList: from

Sold listing courtesy of Dylan Linde from ROOM
0 Loma Prieta AVE, Los Gatos
$180,000
ML82034134 MLS
This property is part of the Kennedy Estate. Discover a peaceful mountain retreat on this scenic, parcel featuring natural beauty, and a small spring. This parcel offers an opportunity for recreation, conservation, or long term land holding in a desirable Los Gatos mountain location. The terrain is predominantly hilly and may limit development potential; buyers should verify buildability, access, utilities, and permitted uses with Santa Clara County. A rare chance to own land with a natural water source in a quiet, wooded setting, and minutes from the Summit Store Inc.

0 Loma Prieta AVE, Los Gatos

Listed by Gregg Fussell, 408-857-0957 from Coldwell Banker Realty
(If provided) CoList: Bill Wilson from Coldwell Banker Realty

Sold listing courtesy of Jim Meech from MEECH

board logoThe data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Bailey Properties are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.


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