Real Estate Investment Properties for Sale in Monticello, NY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
10 Green Street Monticello, NY Improved Price! Step into timeless character with this turn-of-the-century Old Style Colon...	4 beds \| 2 baths \| 2,637 sq.ft.	$349,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 5.5% Airbnb Rental Income: $1490 Traditional Rental Income: $2850 Airbnb ROI: 0.03% Traditional ROI: 5.5%
221 Starlight Rd Monticello, NY Swinging Bridge Reservoir lakefront home. This is your chance to own a lakefront home on S...	3 beds \| 2 baths \| 1,600 sq.ft.	$790,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 0.34% Airbnb Rental Income: $1391 Traditional Rental Income: $2337 Airbnb ROI: -1.52% Traditional ROI: 0.34%
8 Lakeside Dr Monticello, NY Enjoy lakefront community living in (Greentree Village) a peaceful and beautiful place to ...	3 beds \| 3 baths \| 1,112 sq.ft.	$364,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.46% Airbnb Rental Income: $1391 Traditional Rental Income: $2396 Airbnb ROI: -0.71% Traditional ROI: 3.46%
15 Holmes St Monticello, NY NEW RENOVATION!!!!!!!!! NEW FLOORS!! NEW PAINT!!! 3 nice sized bedrooms! Municipal Sewer...	3 beds \| 1 baths \| 770 sq.ft.	$225,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 4.9% Airbnb Rental Income: $1391 Traditional Rental Income: $1545 Airbnb ROI: 2.21% Traditional ROI: 4.9%
45 Coopers Corner Road Monticello, NY Nestled on a sprawling 6.6-acre parcel of private land, this saltbox-style offers the perf...	2 beds \| 3 baths \| 2,468 sq.ft.	$825,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 1.32% Airbnb Rental Income: $1439 Traditional Rental Income: $2899 Airbnb ROI: -1.14% Traditional ROI: 1.32%
22 Smith St Monticello, NY Cute & cozy renovated cottage available for immediate sale. Property is perfect for a vaca...	1 beds \| 1 baths \| 408 sq.ft.	$150,000	Airbnb cash on cash: -2.33% Traditional cash on cash: 3.5% Airbnb Rental Income: $390 Traditional Rental Income: $972 Airbnb ROI: -2.33% Traditional ROI: 3.5%
399 Gregory Rd Monticello, NY Per the Owner's information: Zoned RR2 Agricultural/Residential. Bed and Breakfast, 2-Fam...	14 beds \| 12 baths \| 17,570 sq.ft.	$5,000,000	Airbnb cash on cash: -1.37% Traditional cash on cash: -0.56% Airbnb Rental Income: $2309 Traditional Rental Income: $5487 Airbnb ROI: -1.37% Traditional ROI: -0.56%
10 Hanover Drive Monticello, NY Turnkey opportunity with immediate income in place. This property features a current tenan...	3 beds \| 3 baths \| 1,772 sq.ft.	$354,999	Airbnb cash on cash: 0.08% Traditional cash on cash: 5.71% Airbnb Rental Income: $1391 Traditional Rental Income: $2848 Airbnb ROI: 0.08% Traditional ROI: 5.71%
38 Marjorie Dr Monticello, NY Welcome to this updated 3 bed, 2 bath Colonial home that sits on a beautiful 1 acre lot wi...	4 beds \| 2 baths \| 1,560 sq.ft.	$375,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.78% Airbnb Rental Income: $1490 Traditional Rental Income: $2480 Airbnb ROI: -0.28% Traditional ROI: 3.78%
224 Lake Shore Drive Monticello, NY Welcome to 224 Lake Shore Drive, a turn-key lakeview retreat set on a peaceful 0.55-acre l...	3 beds \| 3 baths \| 2,279 sq.ft.	$650,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 1.29% Airbnb Rental Income: $1391 Traditional Rental Income: $2783 Airbnb ROI: -1.7% Traditional ROI: 1.29%
6 Leonardo Road Monticello, NY LOW LOW TAXES!!! PRIVACY IS KEY!!! Check out his 3 Bedroom, 1 Full Bathroom Ranch style ho...	3 beds \| 1 baths \| 1,027 sq.ft.	$249,999	Airbnb cash on cash: 1.78% Traditional cash on cash: 5.66% Airbnb Rental Income: $1391 Traditional Rental Income: $1886 Airbnb ROI: 1.78% Traditional ROI: 5.66%
114 Levine Road Monticello, NY How would you like the opportunity to own or develop 70 acres of beautiful open pastures, ...	5 beds \| 3 baths \| 4,094 sq.ft.	$2,400,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.25% Airbnb Rental Income: $2309 Traditional Rental Income: $3817 Airbnb ROI: -0.69% Traditional ROI: 0.25%
105 Wood Avenue Monticello, NY Large spacious Renovated 2 story Ready to move in - house is on a quiet residential block ...	4 beds \| 2 baths \| 1,768 sq.ft.	$375,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.28% Airbnb Rental Income: $1490 Traditional Rental Income: $2488 Airbnb ROI: 0.2% Traditional ROI: 4.28%
279 Cold Spring Road Monticello, NY Welcome to this beautifully maintained 3-bedroom, 1.5-bath home, perfectly situated on jus...	3 beds \| 2 baths \| 1,040 sq.ft.	$297,999	Airbnb cash on cash: 1.37% Traditional cash on cash: 4.55% Airbnb Rental Income: $1391 Traditional Rental Income: $1863 Airbnb ROI: 1.37% Traditional ROI: 4.55%
275-277 State Route 17b Monticello, NY Super commercial location with close proximity to Route 17 exit ramps, shopping, service s...	5 beds \| 2 baths \| N/A	$649,900	Airbnb cash on cash: -0.1% Traditional cash on cash: 1.17% Airbnb Rental Income: $2309 Traditional Rental Income: $2507 Airbnb ROI: -0.1% Traditional ROI: 1.17%
46 Lakewood Ave Monticello, NY Discover endless possibilities with this spacious land off Broadway in Monticello, NY. Per...	5 beds \| 2 baths \| 2,441 sq.ft.	$1,500,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.01% Airbnb Rental Income: $2309 Traditional Rental Income: $3718 Airbnb ROI: -0.42% Traditional ROI: 1.01%
33 Melody Lake Dr Monticello, NY Discover this move-in ready 1,248 sq ft, 3-bedroom, 1-bath ranch house featuring hardwood ...	3 beds \| 1 baths \| 1,248 sq.ft.	$199,999	Airbnb cash on cash: 0.63% Traditional cash on cash: 5.49% Airbnb Rental Income: $1391 Traditional Rental Income: $1891 Airbnb ROI: 0.63% Traditional ROI: 5.49%
174 Dingle Daisy Rd Monticello, NY 210 acres of pristine land in Monticello, NY offers a rare opportunity to create your own ...	N/A beds \| N/A baths \| 863 sq.ft.	$1,600,000	Airbnb cash on cash: -1.85% Traditional cash on cash: -0.78% Airbnb Rental Income: $438 Traditional Rental Income: $1758 Airbnb ROI: -1.85% Traditional ROI: -0.78%
47 Washington Ln Monticello, NY EXTRAORDINARY CUSTOM CATSKILL RETREAT ON 9 ACRES WITH INCOME-GENERATING AIRBNB AND GUEST H...	2 beds \| 1 baths \| 2,132 sq.ft.	$829,999	Airbnb cash on cash: -0.63% Traditional cash on cash: 0.99% Airbnb Rental Income: $1439 Traditional Rental Income: $2266 Airbnb ROI: -0.63% Traditional ROI: 0.99%
31 Forestburgh Road Monticello, NY Cash offers only. This unique property in the Village of Monticello offers a great opportu...	3 beds \| 1 baths \| 1,250 sq.ft.	$335,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 3% Airbnb Rental Income: $1391 Traditional Rental Income: $1784 Airbnb ROI: 0.41% Traditional ROI: 3%
97 Pittaluga Dr Monticello, NY Set on 10 acres along a quiet street in Monticello, this well-kept 3-bedroom, 3-bath home ...	5 beds \| 2 baths \| 3,450 sq.ft.	$1,100,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 0.86% Airbnb Rental Income: $2309 Traditional Rental Income: $2938 Airbnb ROI: -0.31% Traditional ROI: 0.86%
162 Park Avenue Monticello, NY Fantastic opportunity in the Village of Monticello-perfect for both end users and savvy in...	5 beds \| 4 baths \| N/A	$449,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 5.44% Airbnb Rental Income: $2309 Traditional Rental Income: $3448 Airbnb ROI: 1.37% Traditional ROI: 5.44%
105-107 E Cold Spring Road Monticello, NY This property brings in $4900 monthly! Low property taxes! Three houses renovated in recen...	3 beds \| 4 baths \| N/A	$525,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 4.09% Airbnb Rental Income: $1391 Traditional Rental Income: $3304 Airbnb ROI: -0.66% Traditional ROI: 4.09%
209 Gregory Road Monticello, NY This newly constructed home was designed with entertaining in mind. The expansive great ro...	3 beds \| 2 baths \| 2,800 sq.ft.	$679,900	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.86% Airbnb Rental Income: $1391 Traditional Rental Income: $2581 Airbnb ROI: -0.68% Traditional ROI: 1.86%
194 Old Liberty Road Monticello, NY MOTIVATED SELLER Welcome to 194 Old Liberty Rd, a 1,508 sq ft single-family home nestled i...	3 beds \| 1 baths \| 1,508 sq.ft.	$299,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 3.68% Airbnb Rental Income: $1391 Traditional Rental Income: $1765 Airbnb ROI: 0.86% Traditional ROI: 3.68%
97 Serenity Lane Monticello, NY An Exclusive Masterpiece: 97 Serenity Lane, Monticello, NY 12701 A truly rare opportunity ...	4 beds \| 5 baths \| 7,825 sq.ft.	$8,000,000	Airbnb cash on cash: -1.21% Traditional cash on cash: -0.6% Airbnb Rental Income: $1490 Traditional Rental Income: $5614 Airbnb ROI: -1.21% Traditional ROI: -0.6%
135-149 Wildcat Road Monticello, NY This multi-family and commercial property set on over 6 acres in Monticello, Thompson town...	9 beds \| 5 baths \| 4,195 sq.ft.	$630,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 6.67% Airbnb Rental Income: $2309 Traditional Rental Income: $5422 Airbnb ROI: 0.4% Traditional ROI: 6.67%
25 Pansy Lane Monticello, NY Welcome to a fantastic opportunity in the sought-after Kinnebrook Community. This 2-bedroo...	2 beds \| 2 baths \| 1,008 sq.ft.	$64,999	Airbnb cash on cash: -2.1% Traditional cash on cash: 10.27% Airbnb Rental Income: $1439 Traditional Rental Income: $1812 Airbnb ROI: -2.1% Traditional ROI: 10.27%
296 Southwoods Dr Monticello, NY 296 Southwoods Dr, Monticello, NY 12701 \| Manufactured Home	3 beds \| 1 baths \| 1,100 sq.ft.	$225,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 3.37% Airbnb Rental Income: $1391 Traditional Rental Income: $1384 Airbnb ROI: 1.42% Traditional ROI: 3.37%
10 Smith St Monticello, NY 10 Smith St, Monticello, NY 12701 \| Multi Family	6 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 4.48% Airbnb Rental Income: $1391 Traditional Rental Income: $2287 Airbnb ROI: 0.17% Traditional ROI: 4.48%
3 Woodcliff Ave Monticello, NY 3 Woodcliff Ave, Monticello, NY 12701 \| Single Family Residential	7 beds \| 3 baths \| 5,700 sq.ft.	$789,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 1.3% Airbnb Rental Income: $2309 Traditional Rental Income: $3044 Airbnb ROI: -0.48% Traditional ROI: 1.3%
33 Landfield Ave Monticello, NY 33 Landfield Ave, Monticello, NY 12701 \| Multi Family	4 beds \| 2 baths \| 1,924 sq.ft.	$325,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 2.58% Airbnb Rental Income: $2309 Traditional Rental Income: $1706 Airbnb ROI: 2.67% Traditional ROI: 2.58%
565 Cold Spring Rd Monticello, NY 565 Cold Spring Rd, Monticello, NY 12701 \| Single Family Residential	2 beds \| 1 baths \| 1,008 sq.ft.	$216,500	Airbnb cash on cash: 1.78% Traditional cash on cash: 2.75% Airbnb Rental Income: $1439 Traditional Rental Income: $1210 Airbnb ROI: 1.78% Traditional ROI: 2.75%
3 Kukas Rd Monticello, NY 3 Kukas Rd, Monticello, NY 12701 \| Single Family Residential	4 beds \| N/A baths \| 1,960 sq.ft.	$395,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.89% Airbnb Rental Income: $1490 Traditional Rental Income: $2166 Airbnb ROI: -0.11% Traditional ROI: 2.89%
14 E Dillon Rd Monticello, NY 14 E Dillon Rd, Monticello, NY 12701 \| Single Family Residential	5 beds \| 2 baths \| 2,400 sq.ft.	$735,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 0.99% Airbnb Rental Income: $2309 Traditional Rental Income: $2628 Airbnb ROI: -0.31% Traditional ROI: 0.99%
568 Old Liberty Rd Monticello, NY 568 Old Liberty Rd, Monticello, NY 12701 \| Single Family Residential	4 beds \| 2 baths \| 2,181 sq.ft.	$365,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 3.67% Airbnb Rental Income: $1490 Traditional Rental Income: $2276 Airbnb ROI: 0.1% Traditional ROI: 3.67%
541 Cold Spring Rd Monticello, NY 541 Cold Spring Rd, Monticello, NY 12701 \| Single Family Residential	3 beds \| 2 baths \| 1,512 sq.ft.	$575,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.66% Airbnb Rental Income: $1391 Traditional Rental Income: $1901 Airbnb ROI: -1.07% Traditional ROI: 0.66%
518 Sackett Lake Rd Monticello, NY 518 Sackett Lake Rd, Monticello, NY 12701 \| Single Family Residential	3 beds \| 2 baths \| 2,280 sq.ft.	$525,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 1.44% Airbnb Rental Income: $1391 Traditional Rental Income: $2128 Airbnb ROI: -0.92% Traditional ROI: 1.44%
5 Blue Spruce Lane Monticello, NY Welcome to 5 Blue Spruce Lane, Monticello, NY - a well-maintained single-family home set o...	4 beds \| 3 baths \| 2,200 sq.ft.	$430,000	Airbnb cash on cash: 0% Traditional cash on cash: 3.02% Airbnb Rental Income: $1490 Traditional Rental Income: $2271 Airbnb ROI: 0% Traditional ROI: 3.02%
394 State Route 17B Lot#19 Monticello, NY Cozy 2 bedroom/2bathroom with washer and dryer hookups in Brookside Mobile Home Park. Set ...	2 beds \| 2 baths \| 960 sq.ft.	$105,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 10.45% Airbnb Rental Income: $1439 Traditional Rental Income: $2041 Airbnb ROI: 0.33% Traditional ROI: 10.45%

Real Estate investment in Monticello, NY

There are 131 properties for sale in the city of Monticello . The median list price in Monticello is $312,000 and the average price per square foot is $153. In May 2026, the average monthly cash on cash return in Monticello is 2.00%. The average monthly rental income in Monticello is $1,845.

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

There are 131 investment properties available for sale in Monticello.

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

The ROI for Long-Term is higher than the Short-Term in Monticello with average rental income of $1,845.

Your search for investment property begins and ends here

Investment Property for Sale in Monticello, NY

10 Green Street

Monticello, NY

4 beds | 2 baths | 2,637 sq.ft.

$349,900

Airbnb cash on cash: 0.03%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $1490

Traditional Rental Income: $2850

Airbnb ROI: 0.03%

Traditional ROI: 5.5%

221 Starlight Rd

Monticello, NY

3 beds | 2 baths | 1,600 sq.ft.

$790,000

Airbnb cash on cash: -1.52%

Traditional cash on cash: 0.34%

Airbnb Rental Income: $1391

Traditional Rental Income: $2337

Airbnb ROI: -1.52%

Traditional ROI: 0.34%

8 Lakeside Dr

Monticello, NY

3 beds | 3 baths | 1,112 sq.ft.

$364,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1391

Traditional Rental Income: $2396

Airbnb ROI: -0.71%

Traditional ROI: 3.46%

15 Holmes St

Monticello, NY

3 beds | 1 baths | 770 sq.ft.

$225,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 4.9%

Airbnb Rental Income: $1391

Traditional Rental Income: $1545

Airbnb ROI: 2.21%

Traditional ROI: 4.9%

45 Coopers Corner Road

Monticello, NY

2 beds | 3 baths | 2,468 sq.ft.

$825,000

Airbnb cash on cash: -1.14%

Traditional cash on cash: 1.32%

Airbnb Rental Income: $1439

Traditional Rental Income: $2899

Airbnb ROI: -1.14%

Traditional ROI: 1.32%

22 Smith St

Monticello, NY

1 beds | 1 baths | 408 sq.ft.

$150,000

Airbnb cash on cash: -2.33%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $390

Traditional Rental Income: $972

Airbnb ROI: -2.33%

Traditional ROI: 3.5%

399 Gregory Rd

Monticello, NY

14 beds | 12 baths | 17,570 sq.ft.

$5,000,000

Airbnb cash on cash: -1.37%

Traditional cash on cash: -0.56%

Airbnb Rental Income: $2309

Traditional Rental Income: $5487

Airbnb ROI: -1.37%

Traditional ROI: -0.56%

10 Hanover Drive

Monticello, NY

3 beds | 3 baths | 1,772 sq.ft.

$354,999

Airbnb cash on cash: 0.08%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $1391

Traditional Rental Income: $2848

Airbnb ROI: 0.08%