Real Estate Investment Properties for Sale in Ossining, NY

Looking for investment property in Ossining, NY with high ROI ?

Explore a variety of short-term homes & houses in Ossining, NY. Invest wisely with VRBO & Ossining, 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 Ossining, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
124 Cedar Ln Ossining, NY Come see this great house located on 1.41 lovely acres with mature trees and a .50 acre bu...	3 beds \| 1 baths \| 1,930 sq.ft.	$749,000	Airbnb cash on cash: -1.9% Traditional cash on cash: 0.52% Airbnb Rental Income: $1811 Traditional Rental Income: $3014 Airbnb ROI: -1.9% Traditional ROI: 0.52%
398 Illington Road Ossining, NY A Charming Farmhouse Style Home, Carefully Restored to Blend Historic Character with Moder...	4 beds \| 3 baths \| 3,128 sq.ft.	$624,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.68% Airbnb Rental Income: $3395 Traditional Rental Income: $3806 Airbnb ROI: -0.32% Traditional ROI: 1.68%
3 Davids Ln Ossining, NY CONVENIENT LOCATION & CONVENIENT LIVING. 2 level townhouse for the price of a co-op offe...	1 beds \| 1 baths \| 1,158 sq.ft.	$375,000	Airbnb cash on cash: -2.15% Traditional cash on cash: 2.99% Airbnb Rental Income: $955 Traditional Rental Income: $2415 Airbnb ROI: -2.15% Traditional ROI: 2.99%
27 Ryder Rd Ossining, NY This home is Spectacular and set on the most serene of settings. Wide open foyer and stai...	4 beds \| 3 baths \| 2,573 sq.ft.	$925,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.15% Airbnb Rental Income: $3395 Traditional Rental Income: $4772 Airbnb ROI: -0.32% Traditional ROI: 2.15%
17 Knoll Vw Ossining, NY Commuters dream with jitney to train. Great tri-level townhome which has been lovingly mai...	1 beds \| 2 baths \| 1,203 sq.ft.	$419,000	Airbnb cash on cash: -3.23% Traditional cash on cash: 2.74% Airbnb Rental Income: $955 Traditional Rental Income: $2949 Airbnb ROI: -3.23% Traditional ROI: 2.74%
55 Sherwood Ave Ossining, NY This charming Dutch Colonial with rocking chair front porch has been owned by the same fam...	3 beds \| 1 baths \| 1,701 sq.ft.	$729,000	Airbnb cash on cash: -1% Traditional cash on cash: 1.66% Airbnb Rental Income: $1811 Traditional Rental Income: $3128 Airbnb ROI: -1% Traditional ROI: 1.66%
1306 Grants Ln Ossining, NY Could be an awesome second home as well as a primary residence. Nestled above a babbling s...	2 beds \| 2 baths \| 1,590 sq.ft.	$1,700,000	Airbnb cash on cash: -1.52% Traditional cash on cash: -0.14% Airbnb Rental Income: $1679 Traditional Rental Income: $3400 Airbnb ROI: -1.52% Traditional ROI: -0.14%
128 Croton Ave Ossining, NY Everything new! Move right into this centrally located mixed use home and call it your ow...	3 beds \| 1 baths \| 1,622 sq.ft.	$200,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 11.06% Airbnb Rental Income: $1811 Traditional Rental Income: $3121 Airbnb ROI: 1.58% Traditional ROI: 11.06%
1 Edward St Ossining, NY Well-maintained two-unit property in the heart of Ossining, fully renovated in 2020 and of...	5 beds \| 2 baths \| 1,860 sq.ft.	$699,000	Airbnb cash on cash: -1.28% Traditional cash on cash: -0.25% Airbnb Rental Income: $1811 Traditional Rental Income: $1993 Airbnb ROI: -1.28% Traditional ROI: -0.25%
227 Cedar Ln Ossining, NY Enchanting, historic hand-hewn log cabin on 6+ lush private acres. Stone fireplace, origin...	2 beds \| 1 baths \| 1,200 sq.ft.	$799,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 0.28% Airbnb Rental Income: $1679 Traditional Rental Income: $2537 Airbnb ROI: -1.51% Traditional ROI: 0.28%
22 Oakbrook Rd Ossining, NY Welcome home to this immaculate cape cod in Ossining! Inviting open floor plan makes enter...	4 beds \| 3 baths \| 1,742 sq.ft.	$684,900	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.43% Airbnb Rental Income: $3395 Traditional Rental Income: $4616 Airbnb ROI: 0.33% Traditional ROI: 3.43%
10 Nicole Cir #9 Ossining, NY Beautiful and private 1 bed/1 bath plus bonus loft/office w/ Rare 1-Car Garage Ownership! ...	1 beds \| 1 baths \| 1,022 sq.ft.	$349,900	Airbnb cash on cash: -2.73% Traditional cash on cash: 3.48% Airbnb Rental Income: $955 Traditional Rental Income: $2650 Airbnb ROI: -2.73% Traditional ROI: 3.48%
135 Main St #201 Ossining, NY Beautiful bright one-bedroom apartment in the quaint downtown area of Ossining. Cafes, Res...	1 beds \| 1 baths \| 729 sq.ft.	$201,999	Airbnb cash on cash: -1.75% Traditional cash on cash: 6.32% Airbnb Rental Income: $955 Traditional Rental Income: $2153 Airbnb ROI: -1.75% Traditional ROI: 6.32%
139 Spring Street Ossining, NY Nestled in the heart of Ossining, this charming two-family home combines space, flexibilit...	5 beds \| 3 baths \| N/A	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.07% Airbnb Rental Income: $null Traditional Rental Income: $3267 Airbnb ROI: N/A Traditional ROI: 1.07%
33 Maurice Ave Ossining, NY Full of warmth, character, and timeless appeal, this charming colonial home offers a wonde...	3 beds \| 1 baths \| 1,280 sq.ft.	$530,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 3.52% Airbnb Rental Income: $1811 Traditional Rental Income: $3475 Airbnb ROI: -0.83% Traditional ROI: 3.52%
16 Rockledge Ave #5P-2 Ossining, NY When You Have Unobstructed Hudson River And Palisades Mountain Views From Every Window In ...	2 beds \| 2 baths \| 1,580 sq.ft.	$425,000	Airbnb cash on cash: -5.99% Traditional cash on cash: 0.06% Airbnb Rental Income: $1679 Traditional Rental Income: $3621 Airbnb ROI: -5.99% Traditional ROI: 0.06%
1 Agate Avenue Ossining, NY Are you thinking about making a move? This is the perfect opportunity you were waiting for...	2 beds \| 1 baths \| 960 sq.ft.	$399,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 3.15% Airbnb Rental Income: $1679 Traditional Rental Income: $2873 Airbnb ROI: -1.3% Traditional ROI: 3.15%
73 Spring St #3D Ossining, NY Spacious 1 bed/1 bath unit w/ 9' ceilings and open floor plan. Large bedroom with walk in ...	1 beds \| 1 baths \| 1,289 sq.ft.	$340,000	Airbnb cash on cash: -3.8% Traditional cash on cash: 2.69% Airbnb Rental Income: $955 Traditional Rental Income: $2681 Airbnb ROI: -3.8% Traditional ROI: 2.69%
6 Reeback Dr Ossining, NY Setback from the road and perched high on the hill you will find this move-in ready 3-bed/...	3 beds \| 1 baths \| 1,867 sq.ft.	$799,999	Airbnb cash on cash: -1.45% Traditional cash on cash: 2.73% Airbnb Rental Income: $1811 Traditional Rental Income: $4440 Airbnb ROI: -1.45% Traditional ROI: 2.73%
1 Noel Drive Ossining, NY Sprawling Cape Cod style home with first floor primary suite on a fabulous, private settin...	4 beds \| 3 baths \| 3,551 sq.ft.	$899,222	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.58% Airbnb Rental Income: $3395 Traditional Rental Income: $4843 Airbnb ROI: -1.06% Traditional ROI: 1.58%
23-096 Liberty Street Ossining, NY THIS IS NOT JUST ANOTHER LISTING! Don't miss this RARE opportunity to own a newly construc...	3 beds \| 3 baths \| 2,250 sq.ft.	$850,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 5.05% Airbnb Rental Income: $1811 Traditional Rental Income: $4939 Airbnb ROI: 0.48% Traditional ROI: 5.05%
42 Campwoods Grounds Ossining, NY This beautifully updated home now features several new upgrades, including a fully reconst...	2 beds \| 2 baths \| 972 sq.ft.	$329,222	Airbnb cash on cash: -0.57% Traditional cash on cash: 5.8% Airbnb Rental Income: $1679 Traditional Rental Income: $3181 Airbnb ROI: -0.57% Traditional ROI: 5.8%
22 Lafayette Avenue Ossining, NY Opportunity knocks. Are you looking for a starter house or is it time to downsize? 22 Lafa...	3 beds \| 1 baths \| 842 sq.ft.	$335,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 6.46% Airbnb Rental Income: $1811 Traditional Rental Income: $3065 Airbnb ROI: 0.92% Traditional ROI: 6.46%
25 William Street Ossining, NY This spacious three-family home in Ossining offers three full stories plus a finished base...	7 beds \| 3 baths \| N/A	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.13% Airbnb Rental Income: $null Traditional Rental Income: $4383 Airbnb ROI: N/A Traditional ROI: 2.13%
110 Morningside Dr Ossining, NY Welcome Home and discover this charming ranch-style residence nestled in one of Ossining's...	3 beds \| 2 baths \| 1,418 sq.ft.	$750,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 1.69% Airbnb Rental Income: $1811 Traditional Rental Income: $3688 Airbnb ROI: -1.7% Traditional ROI: 1.69%
143 N Highland Ave Ossining, NY Legal 3-family home, located in the heart of Ossining. Excellent 1st time buyer opportunit...	4 beds \| 3 baths \| 1,368 sq.ft.	$799,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.86% Airbnb Rental Income: $3395 Traditional Rental Income: $3993 Airbnb ROI: 0.04% Traditional ROI: 1.86%
135 Main Street #203 Ossining, NY Fully available as f 1/7/2026. Exciting 2-bedroom condo in the Village of Ossining! Enjoy ...	2 beds \| 1 baths \| 951 sq.ft.	$210,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 5.94% Airbnb Rental Income: $1679 Traditional Rental Income: $2705 Airbnb ROI: -1.57% Traditional ROI: 5.94%
12 Broad Avenue Ossining, NY Two family home for sale. Each apartment is a very large one bedroom apartment. Private dr...	2 beds \| 3 baths \| N/A	$650,000	Airbnb cash on cash: -1.9% Traditional cash on cash: 2.24% Airbnb Rental Income: $1679 Traditional Rental Income: $3722 Airbnb ROI: -1.9% Traditional ROI: 2.24%
335 Croton Dam Rd Ossining, NY 335 Croton Dam Rd, Ossining, NY 10562 \| Single Family Residential	10 beds \| 5 baths \| 8,881 sq.ft.	$3,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.55% Airbnb Rental Income: $null Traditional Rental Income: $7110 Airbnb ROI: N/A Traditional ROI: -0.55%
83 Somerstown Rd Ossining, NY 83 Somerstown Rd, Ossining, NY 10562 \| Single Family Residential	7 beds \| 5 baths \| 5,502 sq.ft.	$2,900,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.12% Airbnb Rental Income: $null Traditional Rental Income: $7081 Airbnb ROI: N/A Traditional ROI: -0.12%
94-3 Somerstown Rd Ossining, NY 94-3 Somerstown Rd, Ossining, NY 10562 \| Single Family Residential	4 beds \| 3 baths \| 2,693 sq.ft.	$1,899,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 0.17% Airbnb Rental Income: $3395 Traditional Rental Income: $5176 Airbnb ROI: -1.27% Traditional ROI: 0.17%
433 Arcady Rd Ossining, NY 433 Arcady Rd, Ossining, NY 10562 \| Single Family Residential	7 beds \| 5 baths \| 5,700 sq.ft.	$3,995,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.48% Airbnb Rental Income: $null Traditional Rental Income: $8350 Airbnb ROI: N/A Traditional ROI: -0.48%
7 Hawkes Ave Ossining, NY 7 Hawkes Ave, Ossining, NY 10562 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$195,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 7.06% Airbnb Rental Income: $706 Traditional Rental Income: $1899 Airbnb ROI: -1.04% Traditional ROI: 7.06%
Van Wyck St Ossining, NY Van Wyck St, Ossining, NY 10562 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$1,900,000	Airbnb cash on cash: -2.54% Traditional cash on cash: -1.73% Airbnb Rental Income: $706 Traditional Rental Income: $1823 Airbnb ROI: -2.54% Traditional ROI: -1.73%
131 Spring Street Ossining, NY Now offered at a compelling new price, 131 Spring Street is a restored brick two-family of...	4 beds \| 2 baths \| N/A	$799,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.08% Airbnb Rental Income: $3395 Traditional Rental Income: $3868 Airbnb ROI: 0.43% Traditional ROI: 2.08%
11 Meadowbrook Dr Ossining, NY 11 Meadowbrook Dr, Ossining, NY 10562 \| Single Family Residential	3 beds \| N/A baths \| 1,750 sq.ft.	$729,900	Airbnb cash on cash: -0.9% Traditional cash on cash: 2.04% Airbnb Rental Income: $1811 Traditional Rental Income: $3325 Airbnb ROI: -0.9% Traditional ROI: 2.04%
81 Glendale Rd Ossining, NY 81 Glendale Rd, Ossining, NY 10562 \| Single Family Residential	3 beds \| 2 baths \| 3,990 sq.ft.	$800,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.67% Airbnb Rental Income: $1811 Traditional Rental Income: $3359 Airbnb ROI: -1.06% Traditional ROI: 1.67%
54 Allapartus Rd Ossining, NY Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home...	4 beds \| 3 baths \| 2,606 sq.ft.	$1,079,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.5% Airbnb Rental Income: $3395 Traditional Rental Income: $4492 Airbnb ROI: -0.35% Traditional ROI: 1.5%
42 Charter Circle #42 Ossining, NY Welcome to 42 Charter Circle in Ossining, a home that offers space, comfort, and an incred...	2 beds \| 1 baths \| 860 sq.ft.	$235,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 8.64% Airbnb Rental Income: $1679 Traditional Rental Income: $2612 Airbnb ROI: 2.33% Traditional ROI: 8.64%
65 Morningside Drive Ossining, NY Take A Stroll in the Park...The market has waited 50 years for this true gem of a home to ...	3 beds \| 2 baths \| 1,563 sq.ft.	$779,900	Airbnb cash on cash: -1.37% Traditional cash on cash: 1.79% Airbnb Rental Income: $1811 Traditional Rental Income: $3612 Airbnb ROI: -1.37% Traditional ROI: 1.79%

Real Estate investment in Ossining, NY

There are 140 properties for sale in the city of Ossining . The median list price in Ossining is $557,167 and the average price per square foot is $298. In October 2026, the average monthly cash on cash return in Ossining is 3.00%. The average monthly rental income in Ossining is $3,442.

Ossining, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 140 investment properties available for sale in Ossining.

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

The ROI for Long-Term is higher than the Short-Term in Ossining with average rental income of $3,442.

Your search for investment property begins and ends here

Investment Property for Sale in Ossining, NY

124 Cedar Ln

Ossining, NY

3 beds | 1 baths | 1,930 sq.ft.

$749,000

Airbnb cash on cash: -1.9%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $1811

Traditional Rental Income: $3014

Airbnb ROI: -1.9%

Traditional ROI: 0.52%

398 Illington Road

Ossining, NY

4 beds | 3 baths | 3,128 sq.ft.

$624,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $3395

Traditional Rental Income: $3806

Airbnb ROI: -0.32%

Traditional ROI: 1.68%

3 Davids Ln

Ossining, NY

1 beds | 1 baths | 1,158 sq.ft.

$375,000

Airbnb cash on cash: -2.15%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $955

Traditional Rental Income: $2415

Airbnb ROI: -2.15%

Traditional ROI: 2.99%

27 Ryder Rd

Ossining, NY

4 beds | 3 baths | 2,573 sq.ft.

$925,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $3395

Traditional Rental Income: $4772

Airbnb ROI: -0.32%

Traditional ROI: 2.15%

17 Knoll Vw

Ossining, NY

1 beds | 2 baths | 1,203 sq.ft.

$419,000

Airbnb cash on cash: -3.23%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $955

Traditional Rental Income: $2949

Airbnb ROI: -3.23%

Traditional ROI: 2.74%

55 Sherwood Ave

Ossining, NY

3 beds | 1 baths | 1,701 sq.ft.

$729,000

Airbnb cash on cash: -1%

Traditional cash on cash: 1.66%

Airbnb Rental Income: $1811

Traditional Rental Income: $3128

Airbnb ROI: -1%

Traditional ROI: 1.66%

1306 Grants Ln

Ossining, NY

2 beds | 2 baths | 1,590 sq.ft.

$1,700,000

Airbnb cash on cash: -1.52%

Traditional cash on cash: -0.14%

Airbnb Rental Income: $1679

Traditional Rental Income: $3400

Airbnb ROI: -1.52%

Traditional ROI: -0.14%

128 Croton Ave

Ossining, NY

3 beds | 1 baths | 1,622 sq.ft.

$200,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 11.06%

Airbnb Rental Income: $1811

Traditional Rental Income: $3121

Airbnb ROI: 1.58%