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$1,649,995
CRPTP2606565 MLS
Live the Santa Cruz lifestyle while enjoying the flexibility and income potential of a beautifully updated duplex in one of the area's most desirable coastal communities. 303-305 Windham Street offers two spacious 2-bedroom residences, each with its own private yard and one-car garage, with new garage doors, creating an ideal combination of privacy, versatility and indoor-outdoor living. The 305 residence features 2 bedrooms and 1.5 baths, while 303 offers 2 bedrooms and 1 bath. Both homes have been thoughtfully refreshed with remodeled kitchens featuring new cabinetry and quartz countertops, new luxury vinyl plank flooring throughout the first floors, upgraded heating and electrical, new satin-nickel plumbing fixtures, LED lighting, and fresh interior and exterior paint. Unit 303 also features all-new dual-pane windows, while the windows in 305 were replaced approximately 10 years ago. Each unit has its own laundry room. For investors and owner-occupants alike, the numbers add to the appeal. Estimated current market rents are approximately $3,850-$4,300 per unit, offering potential combined rental income of roughly $7,700-$8,600 per month. Live in one and offset your housing costs with income from the other, accommodate extended family in their own private residence, or rent b

303 Windham ST, Santa Cruz

Listing courtesy of Robert Cromer, 619-851-0608 from Century 21 Affiliated
(If provided) CoList: Jeffery Lorenzen from Century 21 Affiliated
$1,399,000
4 Beds ⋅ ML82058814 MLS
Set on a desirable corner lot, 2050 Halterman offers two spacious 2-bedroom, 1.5-bath units totaling approximately 1,920 square feet of combined living space. Recently updated and turn-key, the property is filled with natural light and features mature landscaping including multiple birch trees in the front yard generous private yards, and two attached garages. An ideal setup for owner-occupants, multi-generational living, or investors each unit offers comfortable, light-filled living space, separate laundry, garage parking, and its own fenced outdoor area. Conveniently located near Chanticleer, Felt, and Jose County Parks, as well as local shops, restaurants, and Santa Cruz beaches, this versatile property offers comfortable living and flexibility in a well-established Live Oak neighborhood. Note that photographs only include images of Vacant Unit B.

2050 Halterman AVE, Santa Cruz

Listing courtesy of Charlie Lambert, 831-428-2526 from Compass
(If provided) CoList: Roger Berke from Compass
$1,599,000
4 Beds ⋅ ML82058282 MLS
Located in the midtown community of Santa Cruz's legendary Seabright area this awesomely renovated triplex offers outstanding maintenance free prospects for investors, owner-occupants, or buyers searching for a second home with rental income capacity. Unit A features two bedrooms with an attached garage and laundry, while Units B and C offer one lovely bedroom each with a shared carport. All three units have private yards/outdoor spaces, perfect for relaxing and entertaining. Turnkey means new interior and exterior paint, new windows, quartz countertops, updated flooring, some new appliances, and new light and plumbing fixtures. All units have some updated wiring and new electrical sub-panels; the HVAC for Units A and B have been serviced/cleaned and a new furnace installed in Unit C. Section 1 termite and sewer lateral clearances, make this a true move-in ready opportunity. Experience nearby Tramonti, The Crows Nest, Cafe Palomar, The Buttery, The Crepe Place and Whole Foods. Enjoy midtown amenities with easy access to Seabright Beach, Ocean View Park, Shoppers Corner, the Boardwalk, the iconic Rio Theatre and the Santa Cruz Downtown Mall. The choices for lifestyle activities and possibilities are endless!

915 Cayuga ST, Santa Cruz

Listing courtesy of The Mower Group, 831-818-3878 from David Lyng Real Estate
(If provided) CoList: from

$4,999,000
6 Beds ⋅ ML82058242 MLS
Wake up to the sound of crashing waves at 22800 E Cliff, a premier waterfront property sitting directly on the iconic beaches of Santa Cruz. This rare setup features two attached unitseach with 3 bedrooms and 3 bathrooms designed around jaw-dropping, panoramic views of the Pacific Ocean from sunrise to sunset. This is the ultimate California beach lifestyle. Start your mornings cruising over to Cat & Cloud for coffee, then spend your day enjoying the epic surf breaks right around your corner. For dinner, choose between local favorites like Suda and Lago di Como, or grab fresh ingredients from the neighborhood butcher shop. Boutiques and the Capitola Mall are just minutes away, keeping everything you need close by. Inside, expansive windows fill every room with beautiful natural light. End your day dining al fresco on the deck, soaking in the sunset and the ocean mist.

22800 E Cliff DR, Santa Cruz

Listing courtesy of The Madani Team, 831-234-6683 from Room Real Estate
(If provided) CoList: from

$2,495,000
9 Beds ⋅ ML82057797 MLS
In Santa Cruz, location drives demand, and 2030 Kinsley Street puts an investor in the heart of the Live Oak lifestyle. This four-unit property offers the flexibility to build a strong rental portfolio or live in one residence while generating income from the other three, with potential access to owner-occupied financing. The property includes three two-bedroom residences and one spacious three-bedroom residence, with current rents totaling $15,995 per month. Each unit has its own garage, adding valuable parking and storage for residents. Three units feature updated dual-pane windows, while all four have newer water heaters and gas ranges. Beyond the numbers, its a location renters want to call home. Shopping, schools, Simpkins Family Swim Center, neighborhood parks, athletic fields, Twin Lakes State Beach, and the Santa Cruz Harbor are all nearby, making daily life easy and giving the property lasting rental appeal. For an investor, its a rare combination: four residences, established income, individual garages, and a location that continues to deliver.

2030 Kinsley ST, Santa Cruz

Listing courtesy of Strock Team, 831-688-9800 from eXp Realty of California Inc
(If provided) CoList: Neil Kimmel from eXp Realty of California Inc
$2,695,000
9 Beds ⋅ ML82056624 MLS
Outstanding turnkey fourplex investment opportunity in central Santa Cruz! All units have been tastefully updated and meticulously maintained. The property features 4 separate structures including a beautifully updated 3 bedroom Victorian house, a 2-bedroom cottage, a duplex with 1 bedroom and 3 bedroom units, a separate 4 bay garage building with supplemental living space over the garages, and off-street parking. The large nicely landscaped lot provides ample opportunities for tenants to enjoy outdoor living spaces. Many energy efficiency improvements help keep utility costs low for tenants. Ideal location near downtown with a high walkability score offers tenants easy access to restaurants, shops, Highway 1, the pier, the Boardwalk, and beaches. This is a unique opportunity for an investor looking for a high-quality long-term investment with a strong rental history, very low vacancy rates, and financial upside potential through rent rate increases and the possibility of an ADU conversion per current state and local ADU regulations. The property is also perfect for an owner occupant to reside in a beautiful 3-bedroom, two-bath home while enjoying extra income from the other units, OR for a multi-generational family compound. Bring your investors and owner-occupant clients!

130 Market ST, Santa Cruz

Listing courtesy of Marshall Keneipp, 303-913-8113 from Miritz & Bailey Real Estate, Inc
(If provided) CoList: from

$2,480,000
8 Beds ⋅ ML82051773 MLS
Rare UCSC-area investment opportunity in one of Santa Cruz's strongest rental markets. Ideally located steps from the UCSC bus line, this professionally managed, fully occupied fourplex is well suited for UCSC students, faculty, and staff. Residents enjoy easy access to campus, Downtown Santa Cruz, West Cliff Drive, and the Santa Cruz Beach Boardwalk, all just 1.5 miles from the ocean. The property features 4 spacious 2-bedroom, 1-bath units, each approximately 950 square feet, totaling 8 bedrooms and 4 bathrooms across approximately 3,800 square feet. Floor plans may offer potential for conversion to 3-bedroom configurations for increased income. Comparable 3-bedroom rentals near UCSC may command approximately $4,500-$5,500 per month. Buyer to verify feasibility. Amenities include on-site laundry, separate gas meters, 2 carports, 4 additional off-street parking spaces, and abundant street parking. New water heaters were installed in 2025. The property offers strong rental history, stable cash flow, and generates approximately $186,000 in annual gross income. Potential DSCR financing available.

257 High ST, Santa Cruz

Listing courtesy of Anson Ip, 408-221-7887 from Compass
(If provided) CoList: Seabea Ghoph from KW Thrive Santa Cruz
$1,876,000
3 Beds ⋅ ML82052564 MLS
So much to love about this 1946 post WW2 Santa Cruz bungalow. The moment you walk into the front door of the 2-bedroom front home you'll be greeted with beautiful original wood floors & the dramatic Deco stucco arch! This home retains a lot of its original lovely details. The kitchen is a step back to a different time. You'll be amazed at the original 3 color tile counters & new retro gas stove that brings the charm up! Flooring in the kitchen & laundry room is new but in keeping with the style of the home. BR's have walk-in closets. The bathroom is original with new flooring & lighting. The back 1960's 1-bedroom has newer high-quality laminate floors thru out & newer carpet in the bedroom. This home is a legal 1-bedroom. Home has high open living room ceilings with its own fireplace. The large kitchen/dining room has a door to access its own private yard area. The separate legal detached cottage has a charming kitchen & full bath. Lot is oversized with a large full size 2 car garage, with second washer/dryer hookups. All 3 units have their own separate PG&E meters with 2 sep gas meters. Great comfortable separation of living spaces for multi-generational living. Seabright is one of the most desirable areas and super convenient to everything including the harbor & beaches.

1006 Seabright AVE, Santa Cruz

Listing courtesy of Anthony Silveira, 831-476-8463 from Time Realty
(If provided) CoList: from

$1,785,000
6 Beds ⋅ ML82051657 MLS
Outstanding rental property investment opportunity in central Santa Cruz! Well maintained triplex with many recent improvements, highly desirable two-bedroom apartments, and a strong rental history. Ideally located near the rapidly growing downtown area with a Very walkable and Bikers Paradise rating that offers easy access to restaurants, shops, Whole Foods Market, Highway 1, the pier, Boardwalk, and beaches. Each unit has a private outdoor patio area and rare attached two-car garage that provides ample options for off-street parking, storage, and bonus living space. Lower operating expenses due to recent improvements and the potential for long-term value appreciation make this an excellent investment opportunity in a prime Santa Cruz location. Recent improvements include a newer roof, exterior paint job, sewer lateral replacement, water main replacement, newer water heaters, and interior flooring updates. Triplexes in Santa Cruz with this excellent condition, desirability, and long-term stability are rare in Santa Cruz. Don't miss this opportunity!

136 Market ST, Santa Cruz

Listing courtesy of Marshall Keneipp, 303-913-8113 from Miritz & Bailey Real Estate, Inc
(If provided) CoList: from

$1,699,000
3 Beds ⋅ ML82050646 MLS
Welcome to 2228 Capitola Road, a thoughtfully designed modern property offering the flexibility of a primary residence with built-in rental income potential. Completed as a contemporary single-family home with an attached accessory dwelling unit (ADU), this unique property combines clean architectural design, high-end finishes, and low-maintenance living in one convenient locations. The main residence features two bedrooms and one bath, highlighted by polished concrete floors, expansive windows, and an open-concept living space filled with natural light. The designer kitchen showcases premium finishes and modern styling, creating an ideal space for both everyday living and entertaining. Large windows frame views of the sunny, fully fenced backyard, seamlessly connecting indoor and outdoor living. The attached one-bedroom, one-bath ADU provides exceptional flexibility perfect for rental income or multigenerational living Outside, the professionally designed landscape and sunny back yard provides ample room for gardening, outdoor dining, and relaxation, while requiring minimal upkeep. Additional features include a two-car covered carport, a dedicated storage area, and an all-electric modern design with quality contemporary finishes throughout.

2228 Capitola RD, Santa Cruz

Listing courtesy of Suzanne M. Rodoni, 831-345-4568 from Real Estate Eight Three One
(If provided) CoList: from

$1,100,000
3 Beds ⋅ ML82048349 MLS
Golden Opportunity...Charming DUPLEX in a gorgeous Santa Cruz beachside neighborhood featuring a 2BD/1BA unit and a 1BD/1BA unit. Ideal for Investors, Multigenerational Living or Owner-Occupants seeking rental income potential. Both units offer tasteful improvements while maintaining coastal character & functionality. Conveniently located near beaches, shopping, dining, schools & all that Santa Cruz has to offer, this RARE opportunity offers flexibility & location all in one property. Private access to each Home with street parking on either side of the Building. Each unit is Light & Bright & provides a great space with everything needed for simple living with a lot of storage in the attic. Nice, low-maintenance landscaping all around. The location could not be any better to walk to the Iconic Santa Cruz Beach & Boardwalk. Great Rentals for UCSC students not only for when school is in session but for Summer time too! Unit A has 2bed/1bath & an enclosed yard with a NEW fence which is great for a Garden, BBQ & entertaining. Unit B has 1 Bed/1Bath w/ 2 exterior entry doors for easy access. Both have spacious Kitchens w/ plenty of Counter space & Cabinets open to the Family Room & Dinette area. This unique opportunity to own a property that can fit both lifestyle & investment goals!

114 Park AVE, Santa Cruz

Listing courtesy of Charlene King, 831-801-5464 from CENTURY 21 Masters
(If provided) CoList: Shannan Matthews from CENTURY 21 Masters
$6,685,000
8 Beds ⋅ ML82046156 MLS
Spectacular Front Row 4-unit Apartment Building directly overlooking Seabright State Beach aka "Castle Beach." Magnificent vistas across Monterey Bay from sunrise to sunset. Located in lovely Lower Seabright positioned between the Yacht Harbor and the Beach Boardwalk. This is paradise!

1703 East Cliff DR, Santa Cruz

Listing courtesy of Dave Dawson, 831-901-2856 from Bailey Properties
(If provided) CoList: Dorene Dawson from Bailey Properties
$3,150,000
5 Beds ⋅ ML82043847 MLS
Rare coastal investment opportunity on Santa Cruz's highly desirable Lower Westside, just one block from the ocean and iconic West Cliff Drive. Steps from Lighthouse Field State Beach and the popular Steamer Lane Supply restaurant, this prime location consistently attracts strong rental demand driven by lifestyle, walkability, and proximity to Monterey Bay. One of the largest duplexes this close to the ocean, the property features a 3BD/2BA upper unit and a 2BD/2BA lower unit with a bonus room that functions as a third bedroom, maximizing rental flexibility and income potential. Each unit includes a private 2-car garage, a rare and valuable amenity for tenants near the coast. The upper units private yard with jetted hot tub adds further appeal for premium rents. Flexible income strategies: rent both units for strong cash flow, short-term (buyer to verify) or long-term rental, or occupy one unit while generating income from the other. Tenants will enjoy easy access to downtown Santa Cruz, the Santa Cruz Wharf, and the Santa Cruz Beach Boardwalk, as well as immediate connectivity to coastal and mountain biking trails right from your front door. No need to load up the car. A rare combination of size, location, and versatility, an exceptional addition to any coastal portfolio.

300 Columbia ST, Santa Cruz

Listing courtesy of Tommy Ligon, 831-331-7828 from Bailey Properties
(If provided) CoList: from

$2,700,000
6 Beds ⋅ ML82043770 MLS
This unique beach-house blends timeless architectural character with thoughtful modern updates. It is a turnkey, low maintenance property that has been impeccably maintained since a complete remodel in 2017. Originally a triplex, it was converted to a duplex - each of the two separate units offers three bedrooms/ two baths (the downstairs unit- Unit B, has an additional half bath), along with in-unit washers and dryers. There are two sizable decks upstairs and yard space downstairs, and gated secured parking for at least three cars, plus the option to apply for five additional residential permits with the City of Santa Cruz per unit is available. The light filled interior offers an easy, functional floor plan with comfortable living and dining spaces. This property delivers the flexibility for multigenerational living, guests/ extended family, house hacking, or strong rental income. This prime location delivers the flexibility to walk (89/100), bike (90/100), public transport (48/100), or drive. Excellent schools (buyer to verify): Bayview Elementary (8/10), Mission Hill Middle (9/10), Santa Cruz High (10/10) Schedule your private showing today to see why it was awarded a plaque for Excellence in Green Building and Exceptional Design by the City of Santa Cruz!

512 2nd ST, Santa Cruz

Listing courtesy of Nan Tingley, 408-807-5430 from Cornerstone Real Estate Services
(If provided) CoList: from

$3,725,000
16 Beds ⋅ ML82042938 MLS
Professionally managed UCSC rental opportunity with a phenomenal investment profile. This property features four 1,207 Sq. Ft. 4-Bed/2-Bath units, totaling 16 Bedrooms and 8 Bathrooms across 4,828 Sq. Ft. Benefit from an established rental history, very low vacancy rate, Total Operating Income of nearly $275K/year and a strong Net Operating Income (NOI) of $191K/year. Competitive financing is streamlined with SFR options available. Key features that maximize tenant appeal and minimize owner overhead include: on-site laundry, off-street parking, and 4 separate water and gas meters. The location is unbeatable for student renters, situated directly on the UCSC bus line corridor with quick access to campus and Downtown Santa Cruz. Don't miss this rare chance to secure a high-performing asset in a consistently robust rental market. All units are 4 Bed / 2 Bath

817 California ST, Santa Cruz

Listing courtesy of Sam Bird-Robinson, 831-515-6060 from Compass
(If provided) CoList: Charlie Lambert from Compass
$2,500,000
3 Beds ⋅ ML82030410 MLS
Charming Victorian-style duplex in the heart of Santa Cruz. The upper unit offers approximately 1,100 sq. ft. with 2 bedrooms and 1 bathroom, while the lower unit features approximately 800 sq. ft. with 1 bedroom and 1 bathroom, ideal for investment, owner-occupancy, or multigenerational living. A standout feature is the expansive 17,976 sq. ft. lot, offering compelling future development potential for multi-use and/or additional units (buyer to verify). Surrounded by established higher-density uses, the immediate area reflects what may be possible. For reference, the neighboring property at 314 Jessie St. is improved with an approximately 50-unit apartment building on a lot that appears only modestly larger, highlighting the upside opportunity for this exceptional parcel.

338 Ocean ST, Santa Cruz

Listing courtesy of Paul Zech, 831-247-3007 from Coldwell Banker Realty
(If provided) CoList: from

$2,250,000
8 Beds ⋅ ML82030395 MLS
A gem of a 4 Plex with potential to be a 6 Plex, centrally located. Close to 41st Avenue for shopping and entertainment, Simpkins Swim Center for a good work out, short Drive to the Beach, located on a large parcel in a quite neighborhood. Possible to add 2 Modular single level units. Report by a Land Use Planner indicates a strong possibility, parcel has been surveyed and building envelopes identified. The property has been well maintained all 4 kitchens and bathrooms have been remodeled. Building has a Pest Inspection Clearance. 2nd floor balcony area and access has had all SB 721 work completed. Please do not disturb tenants.

1803 Halterman AVE, Santa Cruz

Listing courtesy of Paul Bailey, 831-818-0406 from Bailey Properties
(If provided) CoList: from

$2,535,000
ML81988389 MLS
New zoning allows for multi-residential. Rare opportunity to own a piece of Santa Cruz History. Located on a highly visible corner on one of Santa Cruz's most well-traveled roads yet walking distance to downtown restaurants and shops. This spacious Victorian house is currently used as an office and is 4,623 Sq. Ft. plus 200 Sq. Ft. of storage space, includes 6 private offices as well as several meeting rooms and breakrooms. City will allow conversion into multi-family. In addition, there is a separate structure with a legal residential unit on second floor above the private office space offering a great opportunity for live/work or great rental income. Established history with therapy and professional office users and possible uses to include live/work, group home / transitional housing/recovery facility. A total of three parcels included and totaling over 18,000 Sq. Potential to merge lots for future development possibilities. Buyer to verify with City of Santa Cruz for residential and developmental possibilities.

603 Mission ST, Santa Cruz

Listing courtesy of Marvin Christie, 831-406-1031 from Anderson Christie, Inc.
(If provided) CoList: David Anderson from Anderson Christie, Inc.

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