Real Estate Investment Properties for Sale in Hillsborough, CA

Looking for investment property in Hillsborough, CA with high ROI ?

Explore a variety of short-term homes & houses in Hillsborough, CA. Invest wisely with VRBO & Hillsborough, CA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Hillsborough, CA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
739 El Cerrito Ave Hillsborough, CA 739 El Cerrito Ave, Hillsborough, CA 94010 \| Single Family Residential	3 beds \| 3 baths \| 2,680 sq.ft.	$4,995,000	Airbnb cash on cash: 0.21% Traditional cash on cash: -0.53% Airbnb Rental Income: $11273 Traditional Rental Income: $5757 Airbnb ROI: 0.21% Traditional ROI: -0.53%
45 Calaveras Ct Hillsborough, CA Developer Special! Set on over 4 acres of land at the end of a cul-de-sac in the Lakeview ...	8 beds \| 7 baths \| 7,132 sq.ft.	$10,450,000	Airbnb cash on cash: -1.35% Traditional cash on cash: -0.7% Airbnb Rental Income: $5062 Traditional Rental Income: $10324 Airbnb ROI: -1.35% Traditional ROI: -0.7%
280 Uplands Dr Hillsborough, CA Perfectly situated in the heart of South Hillsborough, 280 Uplands Drive offers a rare opp...	6 beds \| 6 baths \| 6,430 sq.ft.	$10,880,000	Airbnb cash on cash: -0.87% Traditional cash on cash: -0.23% Airbnb Rental Income: $5062 Traditional Rental Income: $10859 Airbnb ROI: -0.87% Traditional ROI: -0.23%
3080A Ralston Ave Hillsborough, CA 3080A Ralston Ave, Hillsborough, CA 94010 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$5,198,000	Airbnb cash on cash: -1.49% Traditional cash on cash: -1.39% Airbnb Rental Income: $1891 Traditional Rental Income: $1844 Airbnb ROI: -1.49% Traditional ROI: -1.39%
85 Fagan Dr Hillsborough, CA 85 Fagan Dr, Hillsborough, CA 94010 \| Single Family Residential	9 beds \| 7 baths \| 14,290 sq.ft.	$39,000,000	Airbnb cash on cash: -1.65% Traditional cash on cash: -1.49% Airbnb Rental Income: $5062 Traditional Rental Income: $9777 Airbnb ROI: -1.65% Traditional ROI: -1.49%
680 Fairway Cir Hillsborough, CA 680 Fairway Cir, Hillsborough, CA 94010 \| Single Family Residential	3 beds \| 3 baths \| 3,540 sq.ft.	$5,650,000	Airbnb cash on cash: -0.01% Traditional cash on cash: -0.85% Airbnb Rental Income: $11273 Traditional Rental Income: $4821 Airbnb ROI: -0.01% Traditional ROI: -0.85%
760 Chateau Dr Hillsborough, CA 760 Chateau Dr, Hillsborough, CA 94010 \| Single Family Residential	6 beds \| 8 baths \| 7,285 sq.ft.	$6,688,000	Airbnb cash on cash: -1.12% Traditional cash on cash: -0.16% Airbnb Rental Income: $5062 Traditional Rental Income: $9957 Airbnb ROI: -1.12% Traditional ROI: -0.16%
30 Bluebell Ln Hillsborough, CA 30 Bluebell Ln, Hillsborough, CA 94010 \| Single Family Residential	4 beds \| 3 baths \| 3,150 sq.ft.	$4,087,000	Airbnb cash on cash: -1.3% Traditional cash on cash: -0.49% Airbnb Rental Income: $2390 Traditional Rental Income: $4883 Airbnb ROI: -1.3% Traditional ROI: -0.49%
1600 Marlborough Rd Hillsborough, CA 1600 Marlborough Rd, Hillsborough, CA 94010 \| Single Family Residential	7 beds \| 7 baths \| 9,310 sq.ft.	$14,980,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -1% Airbnb Rental Income: $5062 Traditional Rental Income: $10510 Airbnb ROI: -1.47% Traditional ROI: -1%
3085 Ralston Ave Hillsborough, CA 3085 Ralston Ave, Hillsborough, CA 94010 \| Single Family Residential	5 beds \| 6 baths \| 10,495 sq.ft.	$14,995,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -1% Airbnb Rental Income: $5062 Traditional Rental Income: $10542 Airbnb ROI: -1.47% Traditional ROI: -1%
2930 Privet Dr Hillsborough, CA 2930 Privet Dr, Hillsborough, CA 94010 \| Single Family Residential	7 beds \| 6 baths \| 9,035 sq.ft.	$9,800,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -0.67% Airbnb Rental Income: $5062 Traditional Rental Income: $9951 Airbnb ROI: -1.32% Traditional ROI: -0.67%
90 Fagan Dr Hillsborough, CA 90 Fagan Dr, Hillsborough, CA 94010 \| Other	N/A beds \| N/A baths \| N/A	$8,990,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -1.56% Airbnb Rental Income: $1891 Traditional Rental Income: $1719 Airbnb ROI: -1.6% Traditional ROI: -1.56%
100 New Place Rd Hillsborough, CA 100 New Place Rd, Hillsborough, CA 94010 \| Single Family Residential	9 beds \| 9 baths \| 11,141 sq.ft.	$29,995,000	Airbnb cash on cash: -1.61% Traditional cash on cash: -1.43% Airbnb Rental Income: $5062 Traditional Rental Income: $9045 Airbnb ROI: -1.61% Traditional ROI: -1.43%
1407 Carlton Rd Hillsborough, CA 1407 Carlton Rd, Hillsborough, CA 94010 \| Single Family Residential	4 beds \| 3 baths \| 4,070 sq.ft.	$3,750,000	Airbnb cash on cash: -1.26% Traditional cash on cash: -0.53% Airbnb Rental Income: $2390 Traditional Rental Income: $4344 Airbnb ROI: -1.26% Traditional ROI: -0.53%
0 Woodridge Rd Hillsborough, CA 0 Woodridge Rd, Hillsborough, CA 94010 \| Other	N/A beds \| N/A baths \| N/A	$1,995,000	Airbnb cash on cash: -1.06% Traditional cash on cash: -0.88% Airbnb Rental Income: $1891 Traditional Rental Income: $1719 Airbnb ROI: -1.06% Traditional ROI: -0.88%
455 Pinehill Rd Hillsborough, CA 455 Pinehill Rd, Hillsborough, CA 94010 \| Single Family Residential	8 beds \| 10 baths \| 13,675 sq.ft.	$39,888,000	Airbnb cash on cash: -1.65% Traditional cash on cash: -1.52% Airbnb Rental Income: $5062 Traditional Rental Income: $8780 Airbnb ROI: -1.65% Traditional ROI: -1.52%
220 Robin Rd Hillsborough, CA 220 Robin Rd, Hillsborough, CA 94010 \| Single Family Residential	4 beds \| 3 baths \| 3,230 sq.ft.	$6,998,000	Airbnb cash on cash: -1.49% Traditional cash on cash: -0.99% Airbnb Rental Income: $2390 Traditional Rental Income: $5083 Airbnb ROI: -1.49% Traditional ROI: -0.99%
1950 Ralston Ave Hillsborough, CA 1950 Ralston Ave, Hillsborough, CA 94010 \| Single Family Residential	5 beds \| 6 baths \| 5,707 sq.ft.	$15,695,000	Airbnb cash on cash: -1.48% Traditional cash on cash: -1.09% Airbnb Rental Income: $5062 Traditional Rental Income: $9708 Airbnb ROI: -1.48% Traditional ROI: -1.09%
25 Fagan Dr Hillsborough, CA	N/A beds \| N/A baths \| N/A	$14,000,000	Airbnb cash on cash: -1.66% Traditional cash on cash: -1.62% Airbnb Rental Income: $1891 Traditional Rental Income: $1804 Airbnb ROI: -1.66% Traditional ROI: -1.62%
36 Eugenia Way Hillsborough, CA 36 Eugenia Way, Hillsborough, CA 94010 \| Single Family Residential	5 beds \| 4 baths \| 3,500 sq.ft.	$5,280,000	Airbnb cash on cash: -0.95% Traditional cash on cash: -0.35% Airbnb Rental Income: $5062 Traditional Rental Income: $6945 Airbnb ROI: -0.95% Traditional ROI: -0.35%
1850 Brookvale Rd Hillsborough, CA 1850 Brookvale Rd, Hillsborough, CA 94010 \| Single Family Residential	5 beds \| 4 baths \| 4,353 sq.ft.	$11,950,000	Airbnb cash on cash: -1.4% Traditional cash on cash: -1.09% Airbnb Rental Income: $5062 Traditional Rental Income: $7500 Airbnb ROI: -1.4% Traditional ROI: -1.09%
820 Eucalyptus Ave Hillsborough, CA 820 Eucalyptus Ave, Hillsborough, CA 94010 \| Single Family Residential	6 beds \| 4 baths \| 4,230 sq.ft.	$7,500,000	Airbnb cash on cash: -1.19% Traditional cash on cash: -0.68% Airbnb Rental Income: $5062 Traditional Rental Income: $7571 Airbnb ROI: -1.19% Traditional ROI: -0.68%
1200 Armsby Dr Hillsborough, CA 1200 Armsby Dr, Hillsborough, CA 94010 \| Single Family Residential	11 beds \| 10 baths \| 18,535 sq.ft.	$28,995,000	Airbnb cash on cash: -1.61% Traditional cash on cash: -1.41% Airbnb Rental Income: $5062 Traditional Rental Income: $9460 Airbnb ROI: -1.61% Traditional ROI: -1.41%
95 Southdown Ct Hillsborough, CA Offered for the first time in over 40 years, this iconic Hillsborough estate presents a ra...	4 beds \| 6 baths \| 7,032 sq.ft.	$5,995,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 0.37% Airbnb Rental Income: $2390 Traditional Rental Income: $10028 Airbnb ROI: -1.12% Traditional ROI: 0.37%
433 El Centro Rd Hillsborough, CA 433 El Centro Rd, Hillsborough, CA 94010 \| Single Family Residential	5 beds \| 5 baths \| 4,700 sq.ft.	$11,000,000	Airbnb cash on cash: -1.37% Traditional cash on cash: -0.94% Airbnb Rental Income: $5062 Traditional Rental Income: $8384 Airbnb ROI: -1.37% Traditional ROI: -0.94%
1176 Tournament Dr Hillsborough, CA Exceptional location in a coveted community. Captivating views. Prestigious schools. Stunn...	4 beds \| 2 baths \| 3,150 sq.ft.	$3,888,000	Airbnb cash on cash: -0.89% Traditional cash on cash: -0.03% Airbnb Rental Income: $2390 Traditional Rental Income: $4907 Airbnb ROI: -0.89% Traditional ROI: -0.03%
336 Brentwood Rd Hillsborough, CA 336 Brentwood Rd, Hillsborough, CA 94010 \| Single Family Residential	4 beds \| 3 baths \| 3,440 sq.ft.	$5,999,000	Airbnb cash on cash: -1.45% Traditional cash on cash: -0.76% Airbnb Rental Income: $2390 Traditional Rental Income: $5601 Airbnb ROI: -1.45% Traditional ROI: -0.76%
2155 Geri Ln Hillsborough, CA 2155 Geri Ln, Hillsborough, CA 94010 \| Single Family Residential	3 beds \| 3 baths \| 3,810 sq.ft.	$8,999,000	Airbnb cash on cash: -0.66% Traditional cash on cash: -1.18% Airbnb Rental Income: $11273 Traditional Rental Income: $4864 Airbnb ROI: -0.66% Traditional ROI: -1.18%
0 Crystal Springs Rd Hillsborough, CA 0 Crystal Springs Rd, Hillsborough, CA 94010 \| Other	N/A beds \| N/A baths \| N/A	$4,000,000	Airbnb cash on cash: -1.41% Traditional cash on cash: -1.29% Airbnb Rental Income: $1891 Traditional Rental Income: $1804 Airbnb ROI: -1.41% Traditional ROI: -1.29%
0 Tartan Trail Rd Hillsborough, CA 0 Tartan Trail Rd, Hillsborough, CA 94010 \| Other	N/A beds \| N/A baths \| N/A	$4,750,000	Airbnb cash on cash: -1.46% Traditional cash on cash: -1.37% Airbnb Rental Income: $1891 Traditional Rental Income: $1804 Airbnb ROI: -1.46% Traditional ROI: -1.37%
862 Chiltern Rd Hillsborough, CA 862 Chiltern Rd, Hillsborough, CA 94010 \| Single Family Residential	6 beds \| 6 baths \| 6,310 sq.ft.	$11,500,000	Airbnb cash on cash: -1.39% Traditional cash on cash: -0.78% Airbnb Rental Income: $5062 Traditional Rental Income: $10463 Airbnb ROI: -1.39% Traditional ROI: -0.78%
810 Lombardi Ln Hillsborough, CA 810 Lombardi Ln, Hillsborough, CA 94010 \| Single Family Residential	6 beds \| 7 baths \| 7,185 sq.ft.	$14,995,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -1.01% Airbnb Rental Income: $5062 Traditional Rental Income: $10463 Airbnb ROI: -1.47% Traditional ROI: -1.01%
68 Eugenia Way Hillsborough, CA 68 Eugenia Way, Hillsborough, CA 94010 \| Other	N/A beds \| N/A baths \| N/A	$5,300,000	Airbnb cash on cash: -1.49% Traditional cash on cash: -1.41% Airbnb Rental Income: $1891 Traditional Rental Income: $1806 Airbnb ROI: -1.49% Traditional ROI: -1.41%
35 Silk Tree Pl Hillsborough, CA 35 Silk Tree Pl, Hillsborough, CA 94010 \| Single Family Residential	4 beds \| 3 baths \| 3,671 sq.ft.	$3,998,000	Airbnb cash on cash: -1.29% Traditional cash on cash: -0.41% Airbnb Rental Income: $2390 Traditional Rental Income: $5086 Airbnb ROI: -1.29% Traditional ROI: -0.41%
19 Farm Ln Hillsborough, CA 19 Farm Ln, Hillsborough, CA 94010 \| Single Family Residential	6 beds \| 4 baths \| 7,600 sq.ft.	$9,880,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -1.01% Airbnb Rental Income: $5062 Traditional Rental Income: $6885 Airbnb ROI: -1.32% Traditional ROI: -1.01%
380 Robinwood Ln Hillsborough, CA 380 Robinwood Ln, Hillsborough, CA 94010 \| Single Family Residential	5 beds \| 4 baths \| 3,970 sq.ft.	$6,995,000	Airbnb cash on cash: -1.15% Traditional cash on cash: -0.61% Airbnb Rental Income: $5062 Traditional Rental Income: $7493 Airbnb ROI: -1.15% Traditional ROI: -0.61%
600 Eucalyptus Ave Hillsborough, CA 600 Eucalyptus Ave, Hillsborough, CA 94010 \| Single Family Residential	6 beds \| 7 baths \| 10,140 sq.ft.	$19,995,000	Airbnb cash on cash: -1.54% Traditional cash on cash: -1.26% Airbnb Rental Income: $5062 Traditional Rental Income: $9276 Airbnb ROI: -1.54% Traditional ROI: -1.26%
2801 Easton Dr Hillsborough, CA 2801 Easton Dr, Hillsborough, CA 94010 \| Single Family Residential	4 beds \| 4 baths \| 4,260 sq.ft.	$6,999,000	Airbnb cash on cash: -1.49% Traditional cash on cash: -0.71% Airbnb Rental Income: $2390 Traditional Rental Income: $6887 Airbnb ROI: -1.49% Traditional ROI: -0.71%
901 Hillsborough Blvd Hillsborough, CA 901 Hillsborough Blvd, Hillsborough, CA 94010 \| Single Family Residential	5 beds \| 4 baths \| 5,180 sq.ft.	$7,280,000	Airbnb cash on cash: -1.17% Traditional cash on cash: -0.8% Airbnb Rental Income: $5062 Traditional Rental Income: $6560 Airbnb ROI: -1.17% Traditional ROI: -0.8%
20 Castle Ct Hillsborough, CA 20 Castle Ct, Hillsborough, CA 94010 \| Single Family Residential	7 beds \| 6 baths \| 5,722 sq.ft.	$12,000,000	Airbnb cash on cash: -1.4% Traditional cash on cash: -0.93% Airbnb Rental Income: $5062 Traditional Rental Income: $9294 Airbnb ROI: -1.4% Traditional ROI: -0.93%

Hillsborough, CA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 56 investment properties available for sale in Hillsborough.

In 2026, the best neighborhood to buy investment property is Hillsborough.

The ROI for Short-Term is higher than the Long-Term in Hillsborough with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Hillsborough, CA

739 El Cerrito Ave

Hillsborough, CA

3 beds | 3 baths | 2,680 sq.ft.

$4,995,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: -0.53%

Airbnb Rental Income: $11273

Traditional Rental Income: $5757

Airbnb ROI: 0.21%

Traditional ROI: -0.53%

45 Calaveras Ct

Hillsborough, CA

8 beds | 7 baths | 7,132 sq.ft.

$10,450,000

Airbnb cash on cash: -1.35%

Traditional cash on cash: -0.7%

Airbnb Rental Income: $5062

Traditional Rental Income: $10324

Airbnb ROI: -1.35%

Traditional ROI: -0.7%

280 Uplands Dr

Hillsborough, CA

6 beds | 6 baths | 6,430 sq.ft.

$10,880,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: -0.23%

Airbnb Rental Income: $5062

Traditional Rental Income: $10859

Airbnb ROI: -0.87%

Traditional ROI: -0.23%

3080A Ralston Ave

Hillsborough, CA

N/A beds | N/A baths | 0 sq.ft.

$5,198,000

Airbnb cash on cash: -1.49%

Traditional cash on cash: -1.39%

Airbnb Rental Income: $1891

Traditional Rental Income: $1844

Airbnb ROI: -1.49%

Traditional ROI: -1.39%

85 Fagan Dr

Hillsborough, CA

9 beds | 7 baths | 14,290 sq.ft.

$39,000,000

Airbnb cash on cash: -1.65%

Traditional cash on cash: -1.49%

Airbnb Rental Income: $5062

Traditional Rental Income: $9777

Airbnb ROI: -1.65%

Traditional ROI: -1.49%

680 Fairway Cir

Hillsborough, CA

3 beds | 3 baths | 3,540 sq.ft.

$5,650,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $11273

Traditional Rental Income: $4821

Airbnb ROI: -0.01%

Traditional ROI: -0.85%

760 Chateau Dr

Hillsborough, CA

6 beds | 8 baths | 7,285 sq.ft.

$6,688,000

Airbnb cash on cash: -1.12%

Traditional cash on cash: -0.16%

Airbnb Rental Income: $5062

Traditional Rental Income: $9957

Airbnb ROI: -1.12%

Traditional ROI: -0.16%

30 Bluebell Ln

Hillsborough, CA

4 beds | 3 baths | 3,150 sq.ft.

$4,087,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: -0.49%

Airbnb Rental Income: $2390

Traditional Rental Income: $4883

Airbnb ROI: -1.3%