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: -1.11% Traditional cash on cash: 0.47% Airbnb Rental Income: $2789 Traditional Rental Income: $2609 Airbnb ROI: -1.11% Traditional ROI: 0.47%
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%
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: 1.59% Traditional cash on cash: 4.28% Airbnb Rental Income: $2789 Traditional Rental Income: $3565 Airbnb ROI: 1.59% Traditional ROI: 4.28%
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%
1 Princess Tree Ct Port Jefferson, NY Welcome to 1 Princess Tree Court - a rare end-unit townhome in the sought-after private co...	3 beds \| 2 baths \| 2,520 sq.ft.	$705,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 2.84% Airbnb Rental Income: $3484 Traditional Rental Income: $4237 Airbnb ROI: 0.53% Traditional ROI: 2.84%
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%
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: 1.19% Traditional cash on cash: 2.69% Airbnb Rental Income: $3484 Traditional Rental Income: $3622 Airbnb ROI: 1.19% 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: 0.8% Traditional cash on cash: 1.27% Airbnb Rental Income: $5081 Traditional Rental Income: $4706 Airbnb ROI: 0.8% 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: 0.33% Traditional cash on cash: 3.03% Airbnb Rental Income: $2789 Traditional Rental Income: $3773 Airbnb ROI: 0.33% Traditional ROI: 3.03%
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%
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: -1.22% Traditional cash on cash: 0.91% Airbnb Rental Income: $1006 Traditional Rental Income: $1443 Airbnb ROI: -1.22% 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: 0.33% 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%
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: 0.17% Traditional cash on cash: 2.48% Airbnb Rental Income: $2789 Traditional Rental Income: $4925 Airbnb ROI: 0.17% 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: 2.73% Traditional cash on cash: 3.04% Airbnb Rental Income: $5081 Traditional Rental Income: $4269 Airbnb ROI: 2.73% Traditional ROI: 3.04%
105 Laurel Ln Port Jefferson, NY 105 Laurel Ln, Port Jefferson, NY 11777 \| Other	N/A beds \| N/A baths \| N/A	$425,000	Airbnb cash on cash: -1.31% Traditional cash on cash: 0.97% Airbnb Rental Income: $1006 Traditional Rental Income: $1556 Airbnb ROI: -1.31% Traditional ROI: 0.97%
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%
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: 0.62% Traditional cash on cash: 2.44% Airbnb Rental Income: $2789 Traditional Rental Income: $2858 Airbnb ROI: 0.62% 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: 2.29% Traditional cash on cash: 2.7% Airbnb Rental Income: $5081 Traditional Rental Income: $4336 Airbnb ROI: 2.29% 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: 1.15% Traditional cash on cash: 1.75% Airbnb Rental Income: $5081 Traditional Rental Income: $4654 Airbnb ROI: 1.15% 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.	$680,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 1.05% Airbnb Rental Income: $3484 Traditional Rental Income: $3198 Airbnb ROI: 0.29% Traditional ROI: 1.05%
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: 0.46% Traditional cash on cash: 1.19% Airbnb Rental Income: $3484 Traditional Rental Income: $3195 Airbnb ROI: 0.46% 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: 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%
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: 0.12% Traditional cash on cash: 1.82% Airbnb Rental Income: $2789 Traditional Rental Income: $2930 Airbnb ROI: 0.12% Traditional ROI: 1.82%
21 Vantage Court Port Jefferson, NY From the moment you pass through the gates and wind along the beautifully manicured street...	3 beds \| 4 baths \| 3,133 sq.ft.	$899,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.59% Airbnb Rental Income: $3484 Traditional Rental Income: $5284 Airbnb ROI: 0.52% Traditional ROI: 3.59%
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%

Real Estate investment in Port-jefferson, NY

There are 59 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 $266. 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 $4,312.

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

There are 59 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 $4,312.

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: -1.11%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $2789

Traditional Rental Income: $2609

Airbnb ROI: -1.11%

Traditional ROI: 0.47%

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%

1405 Sara Circle

Port Jefferson, NY

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

$569,999

Airbnb cash on cash: 1.59%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $2789

Traditional Rental Income: $3565

Airbnb ROI: 1.59%

Traditional ROI: 4.28%

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%

1 Princess Tree Ct

Port Jefferson, NY

3 beds | 2 baths | 2,520 sq.ft.

$705,000

Airbnb cash on cash: 0.53%

Traditional cash on cash: 2.84%

Airbnb Rental Income: $3484

Traditional Rental Income: $4237

Airbnb ROI: 0.53%

Traditional ROI: 2.84%

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%