Real Estate Investment Properties for Sale in Montgomery, NY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
39 Barley Hill Road Montgomery, NY Welcome to this exquisite victorian-style colonial home with wrap around rocking chair fro...	4 beds \| 3 baths \| 4,332 sq.ft.	$974,500	Airbnb cash on cash: 2.26% Traditional cash on cash: 0.99% Airbnb Rental Income: $5591 Traditional Rental Income: $3321 Airbnb ROI: 2.26% Traditional ROI: 0.99%
54 Maggiolo Drive Montgomery, NY Short sale! Owner needs sold ASAP! Buyer responsible for all shortages including but not l...	4 beds \| 3 baths \| 2,252 sq.ft.	$399,999	Airbnb cash on cash: 7.73% Traditional cash on cash: 5.49% Airbnb Rental Income: $5591 Traditional Rental Income: $3629 Airbnb ROI: 7.73% Traditional ROI: 5.49%
500 Winding Hill Road Montgomery, NY Welcome to your future colonial retreat nestled on 4.4 acres of picturesque landscape, env...	4 beds \| 3 baths \| 2,641 sq.ft.	$750,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 1.89% Airbnb Rental Income: $5591 Traditional Rental Income: $3502 Airbnb ROI: 3.27% Traditional ROI: 1.89%
177 Boyd Street Montgomery, NY Recently renovated and charming three bedroom home with spacious kitchen and great floor p...	3 beds \| 2 baths \| 1,517 sq.ft.	$374,900	Airbnb cash on cash: 5.19% Traditional cash on cash: 4.47% Airbnb Rental Income: $3730 Traditional Rental Income: $2669 Airbnb ROI: 5.19% Traditional ROI: 4.47%
Tbd Winding Hill Road Montgomery, NY Welcome to your future colonial retreat nestled on 5.2 acres of picturesque landscape, env...	4 beds \| 3 baths \| 2,641 sq.ft.	$750,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 1.89% Airbnb Rental Income: $5591 Traditional Rental Income: $3502 Airbnb ROI: 3.27% Traditional ROI: 1.89%
135-139 Union Street Montgomery, NY Located in the Village of Montgomery, a short walk to schools, walking paths, park, worshi...	N/A beds \| N/A baths \| N/A	$1,035,000	Airbnb cash on cash: -0.58% Traditional cash on cash: -0.97% Airbnb Rental Income: $2634 Traditional Rental Income: $1626 Airbnb ROI: -0.58% Traditional ROI: -0.97%
2241 State Route 208 Montgomery, NY Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,	2 beds \| 1 baths \| 1,548 sq.ft.	$275,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 3.76% Airbnb Rental Income: $2308 Traditional Rental Income: $1951 Airbnb ROI: 2.92% Traditional ROI: 3.76%
125 Beaver Dam Road Montgomery, NY VALLEY CENTRAL SCHOOLS!!! Check out this 3 Bedroom, 2 Full Bathroom Ranch style home nestl...	3 beds \| 2 baths \| 1,800 sq.ft.	$474,999	Airbnb cash on cash: 4.1% Traditional cash on cash: 4.43% Airbnb Rental Income: $3730 Traditional Rental Income: $3066 Airbnb ROI: 4.1% Traditional ROI: 4.43%
22 W Corbett Road Montgomery, NY Embrace the unparalleled joy of moving into a home that's entirely yours from the ground u...	4 beds \| 3 baths \| 2,635 sq.ft.	$689,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 2.27% Airbnb Rental Income: $5591 Traditional Rental Income: $3495 Airbnb ROI: 3.79% Traditional ROI: 2.27%
249 Hill Avenue Montgomery, NY This Town of Montgomery home is not your cookie cutter! A sprawling 4 acres of property w...	3 beds \| 3 baths \| 2,915 sq.ft.	$599,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 3.93% Airbnb Rental Income: $3730 Traditional Rental Income: $3802 Airbnb ROI: 2.35% Traditional ROI: 3.93%
60 Weaver Street Montgomery, NY Welcome to this delightful 3-bedroom, 2-bathroom ranch-style home located in the highly de...	3 beds \| 2 baths \| 1,344 sq.ft.	$324,999	Airbnb cash on cash: 5.95% Traditional cash on cash: 4.71% Airbnb Rental Income: $3730 Traditional Rental Income: $2543 Airbnb ROI: 5.95% Traditional ROI: 4.71%
TBD State Route 17K #14 Montgomery, NY NEW CONSTRUCTION!!! VALLEY CENTRAL SCHOOL DISTRICT!!! Welcome to The Ponds at Montgomery! ...	4 beds \| 3 baths \| 2,780 sq.ft.	$899,999	Airbnb cash on cash: 2.51% Traditional cash on cash: 1.43% Airbnb Rental Income: $5591 Traditional Rental Income: $3560 Airbnb ROI: 2.51% Traditional ROI: 1.43%
TBD State Route 17K #13 Montgomery, NY NEW CONSTRUCTION!!! VALLEY CENTRAL SCHOOL DISTRICT!!! Welcome to The Ponds at Montgomery! ...	4 beds \| 3 baths \| 2,554 sq.ft.	$799,999	Airbnb cash on cash: 3.21% Traditional cash on cash: 1.8% Airbnb Rental Income: $5591 Traditional Rental Income: $3421 Airbnb ROI: 3.21% Traditional ROI: 1.8%
164 Pleasant Avenue Montgomery, NY Welcome to your very own oasis in the historic village of Montgomery. Enjoy river views fr...	4 beds \| 3 baths \| 2,528 sq.ft.	$599,900	Airbnb cash on cash: 4.79% Traditional cash on cash: 3.13% Airbnb Rental Income: $5591 Traditional Rental Income: $3540 Airbnb ROI: 4.79% Traditional ROI: 3.13%
TBD State Route 17K #12 Montgomery, NY NEW CONSTRUCTION!!! VALLEY CENTRAL SCHOOL DISTRICT!!! Welcome to The Ponds at Montgomery! ...	3 beds \| 3 baths \| 2,723 sq.ft.	$849,999	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.63% Airbnb Rental Income: $3730 Traditional Rental Income: $3290 Airbnb ROI: 1.16% Traditional ROI: 1.63%
2 Sycamore Drive Montgomery, NY LOCATION! LOCATION! LOCATION! Embrace the quintessential village lifestyle where you will ...	3 beds \| 3 baths \| 1,642 sq.ft.	$479,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.4% Airbnb Rental Income: $3730 Traditional Rental Income: $2921 Airbnb ROI: 3.39% Traditional ROI: 3.4%
26 McKinley Avenue Montgomery, NY New Home, under construction Framing completed, Spray Foam and Drywall to start 9/16/2024....	3 beds \| 3 baths \| 1,824 sq.ft.	$399,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 4.61% Airbnb Rental Income: $3730 Traditional Rental Income: $3276 Airbnb ROI: 3.66% Traditional ROI: 4.61%
26 Collabar Road Montgomery, NY Nestled in the scenic Hudson Valley, just over 1hr from NYC, discover your slice of paradi...	4 beds \| 3 baths \| 2,429 sq.ft.	$575,000	Airbnb cash on cash: 5.51% Traditional cash on cash: 4.05% Airbnb Rental Income: $5591 Traditional Rental Income: $3684 Airbnb ROI: 5.51% Traditional ROI: 4.05%
6 Tyler Street Montgomery, NY New Roof, New Siding. Just needs cosmetic work on the inside. Great for someone looking to...	3 beds \| 2 baths \| 2,300 sq.ft.	$370,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 4.57% Airbnb Rental Income: $3730 Traditional Rental Income: $2909 Airbnb ROI: 4.6% Traditional ROI: 4.57%
248 Tompkins Road Montgomery, NY HIGHEST AND BEST BY SUNDAY 9/22/24 by 6PM This diamond-in-the-rough raised ranch offer...	3 beds \| 3 baths \| 2,180 sq.ft.	$339,999	Airbnb cash on cash: 4.3% Traditional cash on cash: 5.48% Airbnb Rental Income: $3730 Traditional Rental Income: $3298 Airbnb ROI: 4.3% Traditional ROI: 5.48%
10 Powers Lane Montgomery, NY Positioned on a tranquil cul-de-sac, this bi-level home spans just over 2500 square feet. ...	3 beds \| 2 baths \| 2,546 sq.ft.	$445,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 3.87% Airbnb Rental Income: $3730 Traditional Rental Income: $2879 Airbnb ROI: 3.97% Traditional ROI: 3.87%
312 E Main Street AKA 1058 Route 52 Montgomery, NY Walk To the Village of Walden! This 3 Bedroom 2 full bath Cape offers Hardwood Flooring Th...	3 beds \| 2 baths \| 1,404 sq.ft.	$260,000	Airbnb cash on cash: 7.93% Traditional cash on cash: 7.04% Airbnb Rental Income: $3730 Traditional Rental Income: $2700 Airbnb ROI: 7.93% Traditional ROI: 7.04%

Real Estate investment in Montgomery, NY

There are 22 properties for sale in the city of Montgomery . The median list price in Montgomery is $529,000 and the average price per square foot is $227. In January 2025, the average monthly cash on cash return in Montgomery is 4.00%. The average monthly rental income in Montgomery is $3,298.

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

There are 22 investment properties available for sale in Montgomery.

In 2025, the best neighborhood to buy investment property is Montgomery.

The ROI for Short-Term is higher than the Long-Term in Montgomery with average rental income of $3,730.

Your search for investment property begins and ends here

Investment Property for Sale in Montgomery, NY

39 Barley Hill Road

Montgomery, NY

4 beds | 3 baths | 4,332 sq.ft.

$974,500

Airbnb cash on cash: 2.26%

Traditional cash on cash: 0.99%

Airbnb Rental Income: $5591

Traditional Rental Income: $3321

Airbnb ROI: 2.26%

Traditional ROI: 0.99%

54 Maggiolo Drive

Montgomery, NY

4 beds | 3 baths | 2,252 sq.ft.

$399,999

Airbnb cash on cash: 7.73%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $5591

Traditional Rental Income: $3629

Airbnb ROI: 7.73%

Traditional ROI: 5.49%

500 Winding Hill Road

Montgomery, NY

4 beds | 3 baths | 2,641 sq.ft.

$750,000

Airbnb cash on cash: 3.27%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $5591

Traditional Rental Income: $3502

Airbnb ROI: 3.27%

Traditional ROI: 1.89%

177 Boyd Street

Montgomery, NY

3 beds | 2 baths | 1,517 sq.ft.

$374,900

Airbnb cash on cash: 5.19%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $3730

Traditional Rental Income: $2669

Airbnb ROI: 5.19%

Traditional ROI: 4.47%

Tbd Winding Hill Road

Montgomery, NY

4 beds | 3 baths | 2,641 sq.ft.

$750,000

Airbnb cash on cash: 3.27%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $5591

Traditional Rental Income: $3502

Airbnb ROI: 3.27%

Traditional ROI: 1.89%

135-139 Union Street

Montgomery, NY

N/A beds | N/A baths | N/A

$1,035,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: -0.97%

Airbnb Rental Income: $2634

Traditional Rental Income: $1626

Airbnb ROI: -0.58%

Traditional ROI: -0.97%

2241 State Route 208

Montgomery, NY

2 beds | 1 baths | 1,548 sq.ft.

$275,000

Airbnb cash on cash: 2.92%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $2308

Traditional Rental Income: $1951

Airbnb ROI: 2.92%

Traditional ROI: 3.76%

125 Beaver Dam Road

Montgomery, NY

3 beds | 2 baths | 1,800 sq.ft.

$474,999

Airbnb cash on cash: 4.1%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $3730

Traditional Rental Income: $3066

Airbnb ROI: 4.1%