Real Estate Investment Properties for Sale in Port Jefferson, NY

Looking for investment property in Port Jefferson, NY with high ROI ?

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

Single Family Homes for Sale in Port Jefferson, NY

Search for Single Family Residential for Sale in Port Jefferson, New York. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 44 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20 Olympia Street Port Jefferson, NY This expansive farm ranch style home features two separate living spaces perfect for dual ...	4 beds \| 2 baths \| 2,165 sq.ft.	$549,999	Airbnb cash on cash: 4.43% Traditional cash on cash: 4.67% Airbnb Rental Income: $5081 Traditional Rental Income: $4167 Airbnb ROI: 4.43% Traditional ROI: 4.67%
135 Oakwood Rd Port Jefferson, NY Timeless, Classic & Elegant, This Spectacular Completely Upgraded & Elevated Colonial Offe...	4 beds \| 3 baths \| 2,400 sq.ft.	$939,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 2.74% Airbnb Rental Income: $5081 Traditional Rental Income: $4699 Airbnb ROI: 1.99% Traditional ROI: 2.74%
223 Old Post Rd Port Jefferson, NY Set on a beautiful hilltop property surrounded by mature trees, this updated 3-bedroom, 2 ...	3 beds \| 2 baths \| 1,353 sq.ft.	$699,999	Airbnb cash on cash: 1.48% Traditional cash on cash: 2.11% Airbnb Rental Income: $3484 Traditional Rental Income: $3126 Airbnb ROI: 1.48% Traditional ROI: 2.11%
28 Village Woods Rd Port Jefferson, NY Home For The Holidays In A Currier And Ives Seaside Village! Low Taxes! Gorgeous, Sparklin...	4 beds \| 2 baths \| 2,400 sq.ft.	$879,999	Airbnb cash on cash: 2.71% Traditional cash on cash: 2.5% Airbnb Rental Income: $5081 Traditional Rental Income: $3868 Airbnb ROI: 2.71% Traditional ROI: 2.5%
7 Waterview Dr Port Jefferson, NY Opportunity to reside in a sought after Village with private Beaches, Golf Course, award W...	4 beds \| 3 baths \| 3,400 sq.ft.	$1,145,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 2.99% Airbnb Rental Income: $5081 Traditional Rental Income: $6258 Airbnb ROI: 0.91% Traditional ROI: 2.99%
11 Buena Vista Rd Port Jefferson, NY This 1930's Custom Tudor had a Recent Face-Lift. Keeping True to it's Original Italian-Eur...	4 beds \| 2 baths \| 3,000 sq.ft.	$1,499,999	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.27% Airbnb Rental Income: $5081 Traditional Rental Income: $4706 Airbnb ROI: 0.8% Traditional ROI: 1.27%
98 Cliff Rd Port Jefferson, NY Experience unparalleled luxury and architectural grandeur in this extraordinary 15,092-squ...	5 beds \| 7 baths \| 10,122 sq.ft.	$3,199,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.14% Airbnb Rental Income: $6919 Traditional Rental Income: $8254 Airbnb ROI: -0.76% Traditional ROI: 0.14%
10 Pine Path Port Jefferson, NY 10 Pine Path, Port Jefferson, NY 11777 \| Single Family Residential	8 beds \| 4 baths \| 5,804 sq.ft.	$3,950,000	Airbnb cash on cash: -1.22% Traditional cash on cash: -0.89% Airbnb Rental Income: $6919 Traditional Rental Income: $6779 Airbnb ROI: -1.22% Traditional ROI: -0.89%
83 Cliff Rd Port Jefferson, NY Set on 1.5 acres overlooking a pristine golf course, 83 Cliff Road in Port Jefferson deliv...	5 beds \| 4 baths \| 6,184 sq.ft.	$1,699,999	Airbnb cash on cash: 0.55% Traditional cash on cash: 1.68% Airbnb Rental Income: $6919 Traditional Rental Income: $7361 Airbnb ROI: 0.55% Traditional ROI: 1.68%
18 Bell Cir Port Jefferson, NY 18 Bell Cir, Port Jefferson, NY 11777 \| Single Family Residential	5 beds \| 4 baths \| 5,000 sq.ft.	$2,499,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 0.26% Airbnb Rental Income: $6919 Traditional Rental Income: $6996 Airbnb ROI: -0.35% Traditional ROI: 0.26%
306 Liberty Ave Port Jefferson, NY 306 Liberty Ave, Port Jefferson, NY 11777 \| Single Family Residential	3 beds \| 3 baths \| 1,700 sq.ft.	$680,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.03% Airbnb Rental Income: $3484 Traditional Rental Income: $4364 Airbnb ROI: 1.42% Traditional ROI: 4.03%
Lot 6 Pine Hill Ct Port Jefferson, NY Lot 6 Pine Hill Ct, Port Jefferson, NY 11777 \| Single Family Residential	4 beds \| 3 baths \| 3,500 sq.ft.	$1,399,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 0.87% Airbnb Rental Income: $5081 Traditional Rental Income: $4748 Airbnb ROI: 0.33% Traditional ROI: 0.87%
87 Soundview Dr Port Jefferson, NY 87 Soundview Dr, Port Jefferson, NY 11777 \| Single Family Residential	4 beds \| 3 baths \| 2,900 sq.ft.	$999,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 2.24% Airbnb Rental Income: $5081 Traditional Rental Income: $4697 Airbnb ROI: 1.54% Traditional ROI: 2.24%
101 Longfellow Ln Port Jefferson, NY 101 Longfellow Ln, Port Jefferson, NY 11777 \| Single Family Residential	4 beds \| 3 baths \| 1,881 sq.ft.	$779,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 3.04% Airbnb Rental Income: $5081 Traditional Rental Income: $4269 Airbnb ROI: 2.73% Traditional ROI: 3.04%
6 Cliffside Dr Port Jefferson, NY Inc Village--Drive through "The Gates to Belle Terre" onto Cliff road to a dead-end street...	5 beds \| 4 baths \| 4,252 sq.ft.	$1,388,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 3% Airbnb Rental Income: $6919 Traditional Rental Income: $7788 Airbnb ROI: 1.29% Traditional ROI: 3%
7 Deer Path Port Jefferson, NY Don't miss this extremely rare opportunity to own a spectacular expanded ranch in the hear...	5 beds \| 3 baths \| 2,172 sq.ft.	$999,999	Airbnb cash on cash: 2.53% Traditional cash on cash: 1.68% Airbnb Rental Income: $6919 Traditional Rental Income: $4787 Airbnb ROI: 2.53% Traditional ROI: 1.68%
32 Contessa Ct Port Jefferson, NY Experience the Hamptons Lifestyle Located in the prestigious Harbor Hills community on a q...	5 beds \| 3 baths \| 4,200 sq.ft.	$1,599,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 1.97% Airbnb Rental Income: $6919 Traditional Rental Income: $6631 Airbnb ROI: 1.26% Traditional ROI: 1.97%
67 Soundview Dr Port Jefferson, NY Come see this Move in Ready Colonial and call it your home! Freshly painted, Newly renovat...	3 beds \| 3 baths \| 1,824 sq.ft.	$849,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 3.55% Airbnb Rental Income: $3484 Traditional Rental Income: $5142 Airbnb ROI: 0.48% Traditional ROI: 3.55%
302 E Broadway Port Jefferson, NY 302 E Broadway, Port Jefferson, NY 11777 \| Single Family Residential	3 beds \| 2 baths \| 1,518 sq.ft.	$679,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 2.35% Airbnb Rental Income: $3484 Traditional Rental Income: $3298 Airbnb ROI: 1.43% Traditional ROI: 2.35%
406 Brook Rd Port Jefferson, NY 406 Brook Rd, Port Jefferson, NY 11777 \| Single Family Residential	4 beds \| 3 baths \| 3,173 sq.ft.	$1,100,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 1.75% Airbnb Rental Income: $5081 Traditional Rental Income: $4654 Airbnb ROI: 1.15% Traditional ROI: 1.75%
30 Fairway Dr Port Jefferson, NY 30 Fairway Dr, Port Jefferson, NY 11777 \| Single Family Residential	5 beds \| 3 baths \| 3,012 sq.ft.	$1,200,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.41% Airbnb Rental Income: $6919 Traditional Rental Income: $4691 Airbnb ROI: 2.2% Traditional ROI: 1.41%
56 Old Homestead Rd Port Jefferson, NY 56 Old Homestead Rd, Port Jefferson, NY 11777 \| Single Family Residential	4 beds \| 3 baths \| 3,000 sq.ft.	$1,295,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 1.07% Airbnb Rental Income: $5081 Traditional Rental Income: $4649 Airbnb ROI: 0.57% Traditional ROI: 1.07%
107 Red Oak Court Port Jefferson, NY LOCATION is key here! This colonial with in ground pool is located on a DOUBLE cul de sac ...	4 beds \| 3 baths \| 2,200 sq.ft.	$699,999	Airbnb cash on cash: 2.81% Traditional cash on cash: 3.18% Airbnb Rental Income: $5081 Traditional Rental Income: $4287 Airbnb ROI: 2.81% Traditional ROI: 3.18%
108 High St Port Jefferson, NY BACK ON THE MARKET!!! Circa 1855, the Captain Lewis Tooker Home sits prominently in Port J...	4 beds \| 2 baths \| 2,768 sq.ft.	$699,998	Airbnb cash on cash: 3.32% Traditional cash on cash: 4.39% Airbnb Rental Income: $5081 Traditional Rental Income: $4743 Airbnb ROI: 3.32% Traditional ROI: 4.39%
105 Nadia Court Port Jefferson, NY Beautifully updated 3/4 bedroom home located in the desirable Harbor Hills section of Port...	3 beds \| 4 baths \| 3,910 sq.ft.	$899,999	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.58% Airbnb Rental Income: $3484 Traditional Rental Income: $5591 Airbnb ROI: 0.14% Traditional ROI: 3.58%
45 Bell Cir Port Jefferson, NY Perched in the prestigious Belle Terre, this exceptional residence captures sweeping, unob...	4 beds \| 3 baths \| 3,279 sq.ft.	$2,100,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 0.28% Airbnb Rental Income: $5081 Traditional Rental Income: $5160 Airbnb ROI: -0.29% Traditional ROI: 0.28%
3 Settlers Path Port Jefferson, NY Charming ranch nestled on a quiet country-like street offering peace, privacy, and easy on...	4 beds \| 2 baths \| 1,700 sq.ft.	$699,000	Airbnb cash on cash: 3.54% Traditional cash on cash: 3.4% Airbnb Rental Income: $5081 Traditional Rental Income: $3957 Airbnb ROI: 3.54% Traditional ROI: 3.4%
105 Liberty Ave Port Jefferson, NY GREAT OPPORTUNITY FOR YOU TO OWN AN INVESTMENT PROPERTY! Brand New Home- Less Than 5 Years...	4 beds \| 2 baths \| 1,666 sq.ft.	$699,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 4.17% Airbnb Rental Income: $5081 Traditional Rental Income: $4250 Airbnb ROI: 3.86% Traditional ROI: 4.17%
3 Chuck Court Port Jefferson, NY Welcome to 3 Chuck Court, an exceptional 3,700 sq. ft. residence nestled in the heart of t...	5 beds \| 4 baths \| 3,700 sq.ft.	$899,990	Airbnb cash on cash: 3.7% Traditional cash on cash: 4.89% Airbnb Rental Income: $6919 Traditional Rental Income: $6570 Airbnb ROI: 3.7% Traditional ROI: 4.89%
105 Rustic Road Port Jefferson, NY This is a unique opportunity to purchase this spacious 9-room, 4-bedroom, 2.5-bath colonia...	4 beds \| 3 baths \| 2,613 sq.ft.	$599,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 5.55% Airbnb Rental Income: $5081 Traditional Rental Income: $4998 Airbnb ROI: 3.85% Traditional ROI: 5.55%
18 Pilgrim Drive Port Jefferson, NY Just in time for summer living! You will love the inviting kidney shaped, heated inground ...	4 beds \| 3 baths \| 2,500 sq.ft.	$879,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.17% Airbnb Rental Income: $5081 Traditional Rental Income: $4984 Airbnb ROI: 2.03% Traditional ROI: 3.17%
103 Birch Drive Port Jefferson, NY Step into effortless living in this beautifully maintained turnkey colonial, set on a peac...	4 beds \| 3 baths \| 2,000 sq.ft.	$749,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 2.96% Airbnb Rental Income: $5081 Traditional Rental Income: $4543 Airbnb ROI: 2.25% Traditional ROI: 2.96%
104 California Avenue Port Jefferson, NY Step into true elegance with this stunning circa 1940 gem, beautifully nestled on meticulo...	3 beds \| 2 baths \| 1,716 sq.ft.	$945,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 2.3% Airbnb Rental Income: $3484 Traditional Rental Income: $3669 Airbnb ROI: 1.21% Traditional ROI: 2.3%
23 Woodside Avenue Port Jefferson, NY POTENTIAL RENTAL INCOME is included with this home (2 electric meters and off-street parki...	3 beds \| 2 baths \| 1,600 sq.ft.	$499,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 4.38% Airbnb Rental Income: $3484 Traditional Rental Income: $3658 Airbnb ROI: 2.36% Traditional ROI: 4.38%
21 Laurita Gate Port Jefferson, NY Welcome to this beautifully maintained 4-bedroom, 2-bath hi-ranch tucked away on a quiet c...	4 beds \| 2 baths \| 2,222 sq.ft.	$799,999	Airbnb cash on cash: 2.65% Traditional cash on cash: 2.42% Airbnb Rental Income: $5081 Traditional Rental Income: $3881 Airbnb ROI: 2.65% Traditional ROI: 2.42%
12 Deer Path Port Jefferson, NY Spacious & Gracious Colonial-set on 1.15 acres of beautifully maintained property, this cl...	5 beds \| 3 baths \| 2,800 sq.ft.	$1,185,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 1.57% Airbnb Rental Income: $6919 Traditional Rental Income: $4968 Airbnb ROI: 2.13% Traditional ROI: 1.57%
600 Scraggy Hill Road Port Jefferson, NY Updated and impeccably maintained 4BR/2.5Bth Colonial offering the perfect blend of comfor...	4 beds \| 3 baths \| 2,200 sq.ft.	$779,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 2.85% Airbnb Rental Income: $5081 Traditional Rental Income: $4598 Airbnb ROI: 2.09% Traditional ROI: 2.85%
101 Red Oak Court Port Jefferson, NY Welcome to 101 Red Oak Court, a beautifully updated 3-bedroom, 2-full-bath home tucked awa...	3 beds \| 2 baths \| 1,415 sq.ft.	$750,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 2.24% Airbnb Rental Income: $3484 Traditional Rental Income: $3598 Airbnb ROI: 0.98% Traditional ROI: 2.24%
42 Cliff Road Port Jefferson, NY Welcome to this custom-built brick ranch nestled on a beautiful 1.31-acre level lot in the...	3 beds \| 2 baths \| 1,951 sq.ft.	$899,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.79% Airbnb Rental Income: $3484 Traditional Rental Income: $3820 Airbnb ROI: 0.47% Traditional ROI: 1.79%
14 Fairway Dr Port Jefferson, NY Welcome to the ultimate country club lifestyle! This beautiful home is perfectly positione...	4 beds \| 3 baths \| 3,000 sq.ft.	$1,375,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 1.9% Airbnb Rental Income: $5081 Traditional Rental Income: $5175 Airbnb ROI: 1.01% Traditional ROI: 1.9%

Your search for investment property begins and ends here

Single Family Homes for Sale in Port Jefferson, NY

20 Olympia Street

Port Jefferson, NY

4 beds | 2 baths | 2,165 sq.ft.

$549,999

Airbnb cash on cash: 4.43%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $5081

Traditional Rental Income: $4167

Airbnb ROI: 4.43%

Traditional ROI: 4.67%

135 Oakwood Rd

Port Jefferson, NY

4 beds | 3 baths | 2,400 sq.ft.

$939,000

Airbnb cash on cash: 1.99%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $5081

Traditional Rental Income: $4699

Airbnb ROI: 1.99%

Traditional ROI: 2.74%

223 Old Post Rd

Port Jefferson, NY

3 beds | 2 baths | 1,353 sq.ft.

$699,999

Airbnb cash on cash: 1.48%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $3484

Traditional Rental Income: $3126

Airbnb ROI: 1.48%

Traditional ROI: 2.11%

28 Village Woods Rd

Port Jefferson, NY

4 beds | 2 baths | 2,400 sq.ft.

$879,999

Airbnb cash on cash: 2.71%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $5081

Traditional Rental Income: $3868

Airbnb ROI: 2.71%

Traditional ROI: 2.5%

7 Waterview Dr

Port Jefferson, NY

4 beds | 3 baths | 3,400 sq.ft.

$1,145,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $5081

Traditional Rental Income: $6258

Airbnb ROI: 0.91%

Traditional ROI: 2.99%

11 Buena Vista Rd

Port Jefferson, NY

4 beds | 2 baths | 3,000 sq.ft.

$1,499,999

Airbnb cash on cash: 0.8%

Traditional cash on cash: 1.27%

Airbnb Rental Income: $5081

Traditional Rental Income: $4706

Airbnb ROI: 0.8%

Traditional ROI: 1.27%

98 Cliff Rd

Port Jefferson, NY

5 beds | 7 baths | 10,122 sq.ft.

$3,199,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $6919

Traditional Rental Income: $8254

Airbnb ROI: -0.76%

Traditional ROI: 0.14%

10 Pine Path

Port Jefferson, NY

8 beds | 4 baths | 5,804 sq.ft.

$3,950,000

Airbnb cash on cash: -1.22%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $6919

Traditional Rental Income: $6779

Airbnb ROI: -1.22%