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
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.	$774,000	Airbnb cash on cash: -2.16% Traditional cash on cash: 1.17% Airbnb Rental Income: $1913 Traditional Rental Income: $3806 Airbnb ROI: -2.16% Traditional ROI: 1.17%
15 Steven Drive unit: 4 Ossining, NY Welcome to this bright and inviting two bedroom, two bathroom condo located in the desirab...	2 beds \| 2 baths \| 1,337 sq.ft.	$449,000	Airbnb cash on cash: -2.11% Traditional cash on cash: 3.23% Airbnb Rental Income: $1217 Traditional Rental Income: $3072 Airbnb ROI: -2.11% Traditional ROI: 3.23%
1 Edward Street Ossining, NY Well-maintained two-unit property in the heart of Ossining, fully renovated in 2020 and of...	5 beds \| 2 baths \| N/A	$720,000	Airbnb cash on cash: 3.68% Traditional cash on cash: -0.27% Airbnb Rental Income: $5800 Traditional Rental Income: $1993 Airbnb ROI: 3.68% Traditional ROI: -0.27%
4 Spaulding Place Ossining, NY PLEASE NOTE: Home is occupied, appointment required for access to the property. Do not tre...	3 beds \| 2 baths \| 1,636 sq.ft.	$600,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.55% Airbnb Rental Income: $3082 Traditional Rental Income: $3761 Airbnb ROI: 0.08% Traditional ROI: 2.55%
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: 2.61% Traditional cash on cash: 1.07% Airbnb Rental Income: $5523 Traditional Rental Income: $3267 Airbnb ROI: 2.61% Traditional ROI: 1.07%
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: -2.33% Traditional cash on cash: 3.15% Airbnb Rental Income: $1217 Traditional Rental Income: $2873 Airbnb ROI: -2.33% Traditional ROI: 3.15%
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: -2.53% Traditional cash on cash: 1.58% Airbnb Rental Income: $1913 Traditional Rental Income: $4843 Airbnb ROI: -2.53% 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: 1.82% Traditional cash on cash: 5.05% Airbnb Rental Income: $3082 Traditional Rental Income: $4939 Airbnb ROI: 1.82% 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: -1.81% Traditional cash on cash: 5.8% Airbnb Rental Income: $1217 Traditional Rental Income: $3181 Airbnb ROI: -1.81% Traditional ROI: 5.8%
200 Route 9A Ossining, NY Exceptional residence featuring a fully legal accessory apartment, offering rare flexibili...	5 beds \| 4 baths \| 2,520 sq.ft.	$1,099,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 2.58% Airbnb Rental Income: $5523 Traditional Rental Income: $5692 Airbnb ROI: 1.33% Traditional ROI: 2.58%
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: 4.28% Traditional cash on cash: 6.46% Airbnb Rental Income: $3082 Traditional Rental Income: $3065 Airbnb ROI: 4.28% 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: 2.17% Traditional cash on cash: 2.13% Airbnb Rental Income: $5523 Traditional Rental Income: $4383 Airbnb ROI: 2.17% Traditional ROI: 2.13%
18 Adams Road Ossining, NY Welcome to 18 Adams Road! This charming property is tucked away on a quiet dead-end street...	3 beds \| 2 baths \| 1,658 sq.ft.	$799,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.77% Airbnb Rental Income: $3082 Traditional Rental Income: $3667 Airbnb ROI: 0.04% Traditional ROI: 1.77%
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: -1.62% Traditional cash on cash: 1.86% Airbnb Rental Income: $1913 Traditional Rental Income: $3993 Airbnb ROI: -1.62% Traditional ROI: 1.86%
63 Cedar Lane Ossining, NY Welcome to 63 Cedar Lane - Your Hudson River Retreat! Perched on one of Ossining's most so...	3 beds \| 3 baths \| 2,100 sq.ft.	$849,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.15% Airbnb Rental Income: $3082 Traditional Rental Income: $4023 Airbnb ROI: 0.07% Traditional ROI: 2.15%
135 Main Street unit: 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: -3.51% Traditional cash on cash: 5.94% Airbnb Rental Income: $1217 Traditional Rental Income: $2705 Airbnb ROI: -3.51% 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: -2.54% Traditional cash on cash: 2.24% Airbnb Rental Income: $1217 Traditional Rental Income: $3722 Airbnb ROI: -2.54% Traditional ROI: 2.24%
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: -1.23% Traditional cash on cash: 2.08% Airbnb Rental Income: $1913 Traditional Rental Income: $3868 Airbnb ROI: -1.23% Traditional ROI: 2.08%
121 S Highland Avenue unit: 6L Ossining, NY Welcome home to this bright top floor, 2 bedroom, 1 full bathroom unit at The Parkview. Fe...	2 beds \| 1 baths \| 900 sq.ft.	$192,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 11.35% Airbnb Rental Income: $1217 Traditional Rental Income: $2654 Airbnb ROI: 1.33% Traditional ROI: 11.35%
129-3 S Highland Avenue unit: 6A Ossining, NY BACK ON MARKET!!! This is a great community to live in. Close to everything. Great locatio...	1 beds \| 1 baths \| 750 sq.ft.	$150,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 8.73% Airbnb Rental Income: $1343 Traditional Rental Income: $2265 Airbnb ROI: -0.57% Traditional ROI: 8.73%
59 Watson Avenue Ossining, NY Move right in to this beautifully maintained home, freshly painted throughout the interior...	3 beds \| 2 baths \| 1,730 sq.ft.	$649,222	Airbnb cash on cash: 0.09% Traditional cash on cash: 1.85% Airbnb Rental Income: $3082 Traditional Rental Income: $3444 Airbnb ROI: 0.09% Traditional ROI: 1.85%
16 Rockledge Avenue unit: 6K-2 Ossining, NY Terrific 6th-floor unit with Tappan Zee Bridge and Hudson River views from every window, l...	2 beds \| 2 baths \| 1,580 sq.ft.	$354,222	Airbnb cash on cash: -7.24% Traditional cash on cash: 1.24% Airbnb Rental Income: $1217 Traditional Rental Income: $3647 Airbnb ROI: -7.24% Traditional ROI: 1.24%
42 Charter Circle unit: 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: 0.6% Traditional cash on cash: 9.49% Airbnb Rental Income: $1217 Traditional Rental Income: $2802 Airbnb ROI: 0.6% Traditional ROI: 9.49%
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: 0.09% Traditional cash on cash: 1.56% Airbnb Rental Income: $3082 Traditional Rental Income: $3444 Airbnb ROI: 0.09% Traditional ROI: 1.56%
48 Pershing Avenue Ossining, NY Charming and updated Cape Cod-style home in desirable village location. This light-filled ...	4 beds \| 2 baths \| 1,463 sq.ft.	$629,222	Airbnb cash on cash: -1.17% Traditional cash on cash: 3.05% Airbnb Rental Income: $1913 Traditional Rental Income: $3881 Airbnb ROI: -1.17% Traditional ROI: 3.05%
88 Broadway unit: Ph1 Ossining, NY Rare opportunity to purchase a stunning 2 Bedroom/2.5 Bath penthouse condo in the heart of...	2 beds \| 3 baths \| 1,332 sq.ft.	$538,888	Airbnb cash on cash: -3.06% Traditional cash on cash: 2.3% Airbnb Rental Income: $1217 Traditional Rental Income: $3525 Airbnb ROI: -3.06% Traditional ROI: 2.3%
36 Watson Avenue Ossining, NY Perched in the hills above historic downtown Ossining, this artfully renovated colonial wi...	5 beds \| 4 baths \| 2,049 sq.ft.	$745,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 3.16% Airbnb Rental Income: $5523 Traditional Rental Income: $4936 Airbnb ROI: 2.41% Traditional ROI: 3.16%
16 Rockledge Avenue unit: 5K-1 Ossining, NY Welcome to Scarborough Manor, A Co-Op That Offers The Perfect Balance Of Tranquility And C...	2 beds \| 2 baths \| 1,580 sq.ft.	$415,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 6.44% Airbnb Rental Income: $1217 Traditional Rental Income: $3650 Airbnb ROI: -0.82% Traditional ROI: 6.44%
42 Brooke View Drive Ossining, NY Welcome home to The Woods Condominium, a community in Westchester offering both proximity ...	2 beds \| 3 baths \| 1,850 sq.ft.	$690,000	Airbnb cash on cash: -2.29% Traditional cash on cash: 0.78% Airbnb Rental Income: $1217 Traditional Rental Income: $2802 Airbnb ROI: -2.29% Traditional ROI: 0.78%
155 Charter Circle unit: 155 Ossining, NY Welcome to this spacious townhouse-style co-op in Ossining, NY. This inviting home feature...	3 beds \| 2 baths \| 1,250 sq.ft.	$285,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 9.78% Airbnb Rental Income: $3082 Traditional Rental Income: $3444 Airbnb ROI: 5.81% Traditional ROI: 9.78%
55 Hoags Cross Road Ossining, NY Welcome to 55 Hoags Cross Rd. in the desirable New Castle area of Ossining. This beautiful...	3 beds \| 2 baths \| 2,292 sq.ft.	$899,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.77% Airbnb Rental Income: $3082 Traditional Rental Income: $3444 Airbnb ROI: -0.5% Traditional ROI: 0.77%
15 Marshall Place Ossining, NY Welcome home to a charming two family Dutch Colonial in the Forest Park area of Ossining. ...	4 beds \| 2 baths \| N/A	$779,000	Airbnb cash on cash: -1.76% Traditional cash on cash: 1.97% Airbnb Rental Income: $1913 Traditional Rental Income: $4117 Airbnb ROI: -1.76% Traditional ROI: 1.97%
16 Rockledge unit: 2Mm2 Ossining, NY Perched gracefully above the majestic Hudson River, this beautifully renovated one-bedroom...	1 beds \| 1 baths \| 736 sq.ft.	$249,999	Airbnb cash on cash: 0.85% Traditional cash on cash: 6.82% Airbnb Rental Income: $1343 Traditional Rental Income: $2340 Airbnb ROI: 0.85% Traditional ROI: 6.82%
16 Rockledge Avenue unit: 2E2 Ossining, NY This is a rare opportunity to own a truly exceptional residence with panoramic, year-round...	3 beds \| 2 baths \| 2,050 sq.ft.	$699,001	Airbnb cash on cash: 0.8% Traditional cash on cash: 2.43% Airbnb Rental Income: $3082 Traditional Rental Income: $3444 Airbnb ROI: 0.8% Traditional ROI: 2.43%
806 Eagle Bay Drive Ossining, NY Welcome to beautiful Eagle Bay, a gated community along the Hudson River in Ossining. Enjo...	1 beds \| 2 baths \| 1,233 sq.ft.	$475,900	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.98% Airbnb Rental Income: $1343 Traditional Rental Income: $2090 Airbnb ROI: -0.63% Traditional ROI: 1.98%
35 Havell Street Ossining, NY Welcome to 35 Havell St, a legal two family home with a great oppottunity for owner occupi...	5 beds \| 2 baths \| N/A	$775,000	Airbnb cash on cash: 2.37% Traditional cash on cash: N/A Airbnb Rental Income: $5523 Traditional Rental Income: $0 Airbnb ROI: 2.37% Traditional ROI: N/A
15 Prospect Avenue Ossining, NY Step into a welcoming three-bedroom, two full-bath home that's ready to make your life eas...	3 beds \| 2 baths \| 1,520 sq.ft.	$575,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 2.99% Airbnb Rental Income: $3082 Traditional Rental Income: $3580 Airbnb ROI: 0.75% Traditional ROI: 2.99%
27 Allapartus Circle Ossining, NY This distinctive Teatown compound made for gatherings and entertainment blends timeless cr...	5 beds \| 3 baths \| 3,867 sq.ft.	$1,200,000	Airbnb cash on cash: 0.63% Traditional cash on cash: N/A Airbnb Rental Income: $5523 Traditional Rental Income: $0 Airbnb ROI: 0.63% Traditional ROI: N/A
123-6 S Highland Avenue unit: B6 Ossining, NY Bright, sun-drenched, and move-in ready! This top-floor co-op unit offers peaceful living ...	2 beds \| 1 baths \| 950 sq.ft.	$235,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 9.49% Airbnb Rental Income: $1217 Traditional Rental Income: $2802 Airbnb ROI: 0.6% Traditional ROI: 9.49%

Real Estate investment in Ossining, NY

There are 39 properties for sale in the city of Ossining . The median list price in Ossining is $650,000 and the average price per square foot is $394. In April 2026, the average monthly cash on cash return in Ossining is 2.00%. The average monthly rental income in Ossining is $3,444.

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

There are 39 investment properties available for sale in Ossining.

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

The ROI for Short-Term is higher than the Long-Term in Ossining with average rental income of $1,913.

Your search for investment property begins and ends here

Investment Property for Sale in Ossining, NY

398 Illington Road

Ossining, NY

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

$774,000

Airbnb cash on cash: -2.16%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $1913

Traditional Rental Income: $3806

Airbnb ROI: -2.16%

Traditional ROI: 1.17%

15 Steven Drive unit: 4

Ossining, NY

2 beds | 2 baths | 1,337 sq.ft.

$449,000

Airbnb cash on cash: -2.11%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $1217

Traditional Rental Income: $3072

Airbnb ROI: -2.11%

Traditional ROI: 3.23%

1 Edward Street

Ossining, NY

5 beds | 2 baths | N/A

$720,000

Airbnb cash on cash: 3.68%

Traditional cash on cash: -0.27%

Airbnb Rental Income: $5800

Traditional Rental Income: $1993

Airbnb ROI: 3.68%

Traditional ROI: -0.27%

4 Spaulding Place

Ossining, NY

3 beds | 2 baths | 1,636 sq.ft.

$600,000

Airbnb cash on cash: 0.08%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $3082

Traditional Rental Income: $3761

Airbnb ROI: 0.08%

Traditional ROI: 2.55%

139 Spring Street

Ossining, NY

5 beds | 3 baths | N/A

$799,000

Airbnb cash on cash: 2.61%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $5523

Traditional Rental Income: $3267

Airbnb ROI: 2.61%

Traditional ROI: 1.07%

1 Agate Avenue

Ossining, NY

2 beds | 1 baths | 960 sq.ft.

$399,000

Airbnb cash on cash: -2.33%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $1217

Traditional Rental Income: $2873

Airbnb ROI: -2.33%

Traditional ROI: 3.15%

1 Noel Drive

Ossining, NY

4 beds | 3 baths | 3,551 sq.ft.

$899,222

Airbnb cash on cash: -2.53%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $1913

Traditional Rental Income: $4843

Airbnb ROI: -2.53%

Traditional ROI: 1.58%

23-096 Liberty Street

Ossining, NY

3 beds | 3 baths | 2,250 sq.ft.

$850,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $3082

Traditional Rental Income: $4939

Airbnb ROI: 1.82%