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.

Investment Property for Sale in Port Jefferson, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
460 Old Town Rd #3G Port Jefferson, NY 460 Old Town Rd #3G, Port Jefferson, NY 11776 \| Condo/Coop	2 beds \| 1 baths \| 930 sq.ft.	$309,000	Airbnb cash on cash: -3.13% Traditional cash on cash: 0.57% Airbnb Rental Income: $2068 Traditional Rental Income: $2609 Airbnb ROI: -3.13% Traditional ROI: 0.57%
53 Comerford St Port Jefferson, NY 53 Comerford St, Port Jefferson, NY 11776 \| Single Family Residential	4 beds \| 1 baths \| 1,850 sq.ft.	$609,999	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.05% Airbnb Rental Income: $4296 Traditional Rental Income: $3373 Airbnb ROI: 3.09% Traditional ROI: 3.05%
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: 3.16% Traditional cash on cash: 4.67% Airbnb Rental Income: $4296 Traditional Rental Income: $4167 Airbnb ROI: 3.16% Traditional ROI: 4.67%
1405 Sara Circle Port Jefferson, NY Welcome to easy living in the highly sought after Fox Meadow community. This beautifully m...	2 beds \| 3 baths \| 1,700 sq.ft.	$569,999	Airbnb cash on cash: 0.46% Traditional cash on cash: 4.28% Airbnb Rental Income: $2068 Traditional Rental Income: $3565 Airbnb ROI: 0.46% Traditional ROI: 4.28%
5 Buena Vista Rd Port Jefferson, NY Luxury meets coastal elegance! This fully renovated colonial gem, just minutes from town a...	4 beds \| 6 baths \| 3,059 sq.ft.	$1,499,900	Airbnb cash on cash: 0.23% Traditional cash on cash: 3.68% Airbnb Rental Income: $4296 Traditional Rental Income: $8200 Airbnb ROI: 0.23% Traditional ROI: 3.68%
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: 2.23% Traditional cash on cash: 2.11% Airbnb Rental Income: $4072 Traditional Rental Income: $3126 Airbnb ROI: 2.23% 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: 1.92% Traditional cash on cash: 2.5% Airbnb Rental Income: $4296 Traditional Rental Income: $3868 Airbnb ROI: 1.92% 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: 0.3% Traditional cash on cash: 2.99% Airbnb Rental Income: $4296 Traditional Rental Income: $6258 Airbnb ROI: 0.3% Traditional ROI: 2.99%
15 Cliff Rd Port Jefferson, NY Beautiful cleared 1-acre property in the sought after Belle Terre peninsula of Port Jeffer...	3 beds \| 2 baths \| 1,800 sq.ft.	$999,999	Airbnb cash on cash: 1.24% Traditional cash on cash: 1.56% Airbnb Rental Income: $4072 Traditional Rental Income: $3501 Airbnb ROI: 1.24% Traditional ROI: 1.56%
213 Windward Ct N Port Jefferson, NY Light, bright, stunning end unit with many upgrades. Don't miss the opportunity to own the...	3 beds \| 2 baths \| 1,727 sq.ft.	$649,000	Airbnb cash on cash: 2% Traditional cash on cash: 2.69% Airbnb Rental Income: $4072 Traditional Rental Income: $3622 Airbnb ROI: 2% Traditional ROI: 2.69%
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: 0.33% Traditional cash on cash: 1.27% Airbnb Rental Income: $4296 Traditional Rental Income: $4706 Airbnb ROI: 0.33% Traditional ROI: 1.27%
56 Leeward Ct Port Jefferson, NY Want to live with an oasis in your backyard, a five minute walk to the LIRR and be a part ...	2 beds \| 2 baths \| 1,727 sq.ft.	$649,999	Airbnb cash on cash: -0.66% Traditional cash on cash: 3.03% Airbnb Rental Income: $2068 Traditional Rental Income: $3773 Airbnb ROI: -0.66% Traditional ROI: 3.03%
15 Hillcrest Ave Port Jefferson, NY Stunning Colonial! With Private Yard; Great Family Home! A Must See! 5 Bedroom; 3.5 Baths;...	5 beds \| 3 baths \| 2,600 sq.ft.	$874,999	Airbnb cash on cash: 3.04% Traditional cash on cash: 3.37% Airbnb Rental Income: $5959 Traditional Rental Income: $5051 Airbnb ROI: 3.04% Traditional ROI: 3.37%
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: -1.03% Traditional cash on cash: 0.14% Airbnb Rental Income: $5959 Traditional Rental Income: $8254 Airbnb ROI: -1.03% Traditional ROI: 0.14%
5 Princess Tree Ct Port Jefferson, NY This Well Maintained 4 Bedroom 3 and a Half Bath, Spacious and Beautiful Townhouse Has Soa...	4 beds \| 3 baths \| 3,200 sq.ft.	$849,900	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.93% Airbnb Rental Income: $4296 Traditional Rental Income: $5817 Airbnb ROI: 0.87% Traditional ROI: 3.93%
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: -1.43% Traditional cash on cash: -0.89% Airbnb Rental Income: $5959 Traditional Rental Income: $6779 Airbnb ROI: -1.43% 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: 0.04% Traditional cash on cash: 1.68% Airbnb Rental Income: $5959 Traditional Rental Income: $7361 Airbnb ROI: 0.04% 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: -0.69% Traditional cash on cash: 0.26% Airbnb Rental Income: $5959 Traditional Rental Income: $6996 Airbnb ROI: -0.69% 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.	$669,999	Airbnb cash on cash: 2.27% Traditional cash on cash: 4.13% Airbnb Rental Income: $4072 Traditional Rental Income: $4364 Airbnb ROI: 2.27% Traditional ROI: 4.13%
Dark Hollow Rd Port Jefferson, NY Dark Hollow Rd, Port Jefferson, NY 11777 \| Other	N/A beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: -1.39% Traditional cash on cash: 0.91% Airbnb Rental Income: $929 Traditional Rental Income: $1443 Airbnb ROI: -1.39% Traditional ROI: 0.91%
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: -0.17% Traditional cash on cash: 0.87% Airbnb Rental Income: $4296 Traditional Rental Income: $4748 Airbnb ROI: -0.17% 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: 0.84% Traditional cash on cash: 2.24% Airbnb Rental Income: $4296 Traditional Rental Income: $4697 Airbnb ROI: 0.84% Traditional ROI: 2.24%
11 Theresa Lane Port Jefferson, NY ALL REASONABLE OFFERS WELCOME! SELLER EXTREMELY MOTIVATED! Welcome to this exclusive three...	2 beds \| 4 baths \| 3,000 sq.ft.	$1,299,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.48% Airbnb Rental Income: $2068 Traditional Rental Income: $4925 Airbnb ROI: -0.32% Traditional ROI: 2.48%
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: 1.83% Traditional cash on cash: 3.04% Airbnb Rental Income: $4296 Traditional Rental Income: $4269 Airbnb ROI: 1.83% Traditional ROI: 3.04%
105 Laurel Ln Port Jefferson, NY 105 Laurel Ln, Port Jefferson, NY 11777 \| Other	4 beds \| 3 baths \| 2,800 sq.ft.	$1,150,000	Airbnb cash on cash: 0.37% Traditional cash on cash: -1.34% Airbnb Rental Income: $4296 Traditional Rental Income: $1556 Airbnb ROI: 0.37% Traditional ROI: -1.34%
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: 0.67% Traditional cash on cash: 3% Airbnb Rental Income: $5959 Traditional Rental Income: $7788 Airbnb ROI: 0.67% 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: 1.67% Traditional cash on cash: 1.68% Airbnb Rental Income: $5959 Traditional Rental Income: $4787 Airbnb ROI: 1.67% 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: 0.72% Traditional cash on cash: 1.97% Airbnb Rental Income: $5959 Traditional Rental Income: $6631 Airbnb ROI: 0.72% 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: 1.1% Traditional cash on cash: 3.55% Airbnb Rental Income: $4072 Traditional Rental Income: $5142 Airbnb ROI: 1.1% 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: 2.21% Traditional cash on cash: 2.35% Airbnb Rental Income: $4072 Traditional Rental Income: $3298 Airbnb ROI: 2.21% Traditional ROI: 2.35%
88 Leeward Ct Port Jefferson, NY 88 Leeward Ct, Port Jefferson, NY 11777 \| Condo/Coop	2 beds \| 2 baths \| 1,350 sq.ft.	$425,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 2.44% Airbnb Rental Income: $2068 Traditional Rental Income: $2858 Airbnb ROI: -0.89% Traditional ROI: 2.44%
6 Princess Tree Ct Port Jefferson, NY 6 Princess Tree Ct, Port Jefferson, NY 11777 \| Condo/Coop	4 beds \| 3 baths \| 2,350 sq.ft.	$759,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.7% Airbnb Rental Income: $4296 Traditional Rental Income: $4336 Airbnb ROI: 1.36% Traditional ROI: 2.7%
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: 0.51% Traditional cash on cash: 1.75% Airbnb Rental Income: $4296 Traditional Rental Income: $4654 Airbnb ROI: 0.51% Traditional ROI: 1.75%
149 Windward Ct S Port Jefferson, NY 149 Windward Ct S, Port Jefferson, NY 11777 \| Condo/Coop	3 beds \| 2 baths \| 1,900 sq.ft.	$670,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 1.11% Airbnb Rental Income: $4072 Traditional Rental Income: $3198 Airbnb ROI: 1.12% Traditional ROI: 1.11%
35 Timberline Cir Port Jefferson, NY 35 Timberline Cir, Port Jefferson, NY 11777 \| Condo/Coop	3 beds \| 2 baths \| 1,678 sq.ft.	$699,800	Airbnb cash on cash: 1.21% Traditional cash on cash: 1.19% Airbnb Rental Income: $4072 Traditional Rental Income: $3195 Airbnb ROI: 1.21% Traditional ROI: 1.19%
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: 1.49% Traditional cash on cash: 1.41% Airbnb Rental Income: $5959 Traditional Rental Income: $4691 Airbnb ROI: 1.49% 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.	$1,199,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 1.38% Airbnb Rental Income: $4296 Traditional Rental Income: $4649 Airbnb ROI: 0.25% Traditional ROI: 1.38%
193 Windward Dr Port Jefferson, NY 193 Windward Dr, Port Jefferson, NY 11777 \| Condo/Coop	2 beds \| 2 baths \| 1,385 sq.ft.	$499,900	Airbnb cash on cash: -1.16% Traditional cash on cash: 1.82% Airbnb Rental Income: $2068 Traditional Rental Income: $2930 Airbnb ROI: -1.16% Traditional ROI: 1.82%
12 Lost Mdw Port Jefferson, NY 12 Lost Mdw, Port Jefferson, NY 11777 \| Single Family Residential	4 beds \| 2 baths \| 3,900 sq.ft.	$1,250,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 0.49% Airbnb Rental Income: $4296 Traditional Rental Income: $3811 Airbnb ROI: 0.13% Traditional ROI: 0.49%
24 Old Homestead Rd Port Jefferson, NY 24 Old Homestead Rd, Port Jefferson, NY 11777 \| Single Family Residential	3 beds \| 2 baths \| 1,504 sq.ft.	$829,999	Airbnb cash on cash: 1.31% Traditional cash on cash: 1.4% Airbnb Rental Income: $4072 Traditional Rental Income: $3268 Airbnb ROI: 1.31% Traditional ROI: 1.4%

Real Estate investment in Port-jefferson, NY

There are 73 properties for sale in the city of Port Jefferson . The median list price in Port Jefferson is $696,083 and the average price per square foot is $268. In September 2026, the average monthly cash on cash return in Port Jefferson is 2.00%. The average monthly rental income in Port Jefferson is $4,350.

Port-jefferson, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 73 investment properties available for sale in Port-jefferson.

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

The ROI for Long-Term is higher than the Short-Term in Port-jefferson with average rental income of $4,350.

Your search for investment property begins and ends here

Investment Property for Sale in Port Jefferson, NY

460 Old Town Rd #3G

Port Jefferson, NY

2 beds | 1 baths | 930 sq.ft.

$309,000

Airbnb cash on cash: -3.13%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $2068

Traditional Rental Income: $2609

Airbnb ROI: -3.13%

Traditional ROI: 0.57%

53 Comerford St

Port Jefferson, NY

4 beds | 1 baths | 1,850 sq.ft.

$609,999

Airbnb cash on cash: 3.09%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $4296

Traditional Rental Income: $3373

Airbnb ROI: 3.09%

Traditional ROI: 3.05%

20 Olympia Street

Port Jefferson, NY

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

$549,999

Airbnb cash on cash: 3.16%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $4296

Traditional Rental Income: $4167

Airbnb ROI: 3.16%

Traditional ROI: 4.67%

1405 Sara Circle

Port Jefferson, NY

2 beds | 3 baths | 1,700 sq.ft.

$569,999

Airbnb cash on cash: 0.46%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $2068

Traditional Rental Income: $3565

Airbnb ROI: 0.46%

Traditional ROI: 4.28%

5 Buena Vista Rd

Port Jefferson, NY

4 beds | 6 baths | 3,059 sq.ft.

$1,499,900

Airbnb cash on cash: 0.23%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $4296

Traditional Rental Income: $8200

Airbnb ROI: 0.23%

Traditional ROI: 3.68%

223 Old Post Rd

Port Jefferson, NY

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

$699,999

Airbnb cash on cash: 2.23%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $4072

Traditional Rental Income: $3126

Airbnb ROI: 2.23%

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: 1.92%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $4296

Traditional Rental Income: $3868

Airbnb ROI: 1.92%

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: 0.3%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $4296

Traditional Rental Income: $6258

Airbnb ROI: 0.3%