Real Estate Investment Properties for Sale in Middletown, NY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
179 Reservoir Road Middletown, NY Welcome to the OPPORTUNITY OF A LIFETIME! This one-of-a-kind home with its one-of-a-kind y...	3 beds \| 2 baths \| 3,080 sq.ft.	$699,999	Airbnb cash on cash: 0.45% Traditional cash on cash: 2.51% Airbnb Rental Income: $2744 Traditional Rental Income: $3438 Airbnb ROI: 0.45% Traditional ROI: 2.51%
214 Brown Road Middletown, NY Sitting perfectly on 5.3 acres with a 2+ acre spring-fed, fully aerated pond, "Fair Oaks R...	3 beds \| 4 baths \| 2,240 sq.ft.	$695,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 3.23% Airbnb Rental Income: $2744 Traditional Rental Income: $3765 Airbnb ROI: 0.65% Traditional ROI: 3.23%
600 Goshen Turnpike Middletown, NY Goshen turpike now offers you this turnkey 3 bedrrom/2.5 bath home that sits on 4 acres of...	3 beds \| 3 baths \| 2,000 sq.ft.	$490,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 4.1% Airbnb Rental Income: $2744 Traditional Rental Income: $3278 Airbnb ROI: 1.52% Traditional ROI: 4.1%
568 County Route 49 #2C Middletown, NY FOR INVESTORS ONLY.... New townhouse available in the Minisink Valley School District. Thi...	3 beds \| 3 baths \| 1,593 sq.ft.	$399,900	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.48% Airbnb Rental Income: $2744 Traditional Rental Income: $2469 Airbnb ROI: 1.49% Traditional ROI: 2.48%
36 Putters Way Middletown, NY This Luxurious townhouse offers great space and a contemporary flair. The main level offer...	3 beds \| 3 baths \| 2,690 sq.ft.	$479,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 1.35% Airbnb Rental Income: $2744 Traditional Rental Income: $2469 Airbnb ROI: 0.52% Traditional ROI: 1.35%
358 Concord Lane Middletown, NY Welcome to this beautiful 2-bedroom, 2-bathroom condo located in the heart of Middletown, ...	2 beds \| 2 baths \| 924 sq.ft.	$224,999	Airbnb cash on cash: 3.72% Traditional cash on cash: 4.74% Airbnb Rental Income: $2603 Traditional Rental Income: $2198 Airbnb ROI: 3.72% Traditional ROI: 4.74%
350 Concord Lane Middletown, NY Welcome to this beautiful 2-bedroom, 2-bathroom condo located in the heart of Middletown, ...	2 beds \| 2 baths \| 955 sq.ft.	$224,999	Airbnb cash on cash: 3.64% Traditional cash on cash: 4.66% Airbnb Rental Income: $2603 Traditional Rental Income: $2198 Airbnb ROI: 3.64% Traditional ROI: 4.66%
2 Highrose Ridge Way Middletown, NY Happiness awaits you at Highrose Ridge Way!!! Over 3000 square foot in this luxurious livi...	3 beds \| 3 baths \| 3,057 sq.ft.	$435,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.85% Airbnb Rental Income: $2744 Traditional Rental Income: $3494 Airbnb ROI: 0.42% Traditional ROI: 3.85%
90 Inwood Road Middletown, NY Welcome to this fully renovated townhouse in Inwood Hills Condominiums. This Home is a fir...	2 beds \| 1 baths \| 940 sq.ft.	$199,999	Airbnb cash on cash: 5.7% Traditional cash on cash: 5.14% Airbnb Rental Income: $2603 Traditional Rental Income: $1874 Airbnb ROI: 5.7% Traditional ROI: 5.14%
11 Black Stallion Court Middletown, NY Centrally located and move in ready town house in the town of Wallkill with Middletown Sch...	3 beds \| 2 baths \| 1,188 sq.ft.	$310,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 5.65% Airbnb Rental Income: $2744 Traditional Rental Income: $2619 Airbnb ROI: 3.86% Traditional ROI: 5.65%
226 Concord Lane Middletown, NY Renovated in 2021 is this first floor 1 bedroom condo in Buttonwood conveniently located c...	1 beds \| 1 baths \| 735 sq.ft.	$155,900	Airbnb cash on cash: 4.6% Traditional cash on cash: 5.1% Airbnb Rental Income: $2399 Traditional Rental Income: $1885 Airbnb ROI: 4.6% Traditional ROI: 5.1%
107 Jimal Drive Middletown, NY Come see this contemporary condo in the idyllic Highland Park Village community. The two-s...	2 beds \| 2 baths \| 1,082 sq.ft.	$242,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 4.68% Airbnb Rental Income: $2603 Traditional Rental Income: $2245 Airbnb ROI: 3.52% Traditional ROI: 4.68%
25 Meyer Road Middletown, NY A-Frame home in the town of Wallkill within the Minisink School District. The home is nest...	3 beds \| 2 baths \| 1,335 sq.ft.	$390,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 5.54% Airbnb Rental Income: $2744 Traditional Rental Income: $3056 Airbnb ROI: 2.92% Traditional ROI: 5.54%
26 Mills Avenue Middletown, NY Looking for a Large home for the extended family or Inlaw-suite/Mother Daughter setup? Loo...	5 beds \| 3 baths \| 2,200 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.9% Airbnb Rental Income: $null Traditional Rental Income: $3675 Airbnb ROI: N/A Traditional ROI: 8.9%
16 Beth Place Middletown, NY Welcome to Beth Place. This charming, fully detached, raised ranch is near everything that...	3 beds \| 3 baths \| 1,814 sq.ft.	$429,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 4.98% Airbnb Rental Income: $2744 Traditional Rental Income: $3328 Airbnb ROI: 1.92% Traditional ROI: 4.98%
30 Daly Road Middletown, NY New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partiall...	3 beds \| 3 baths \| 2,205 sq.ft.	$550,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.64% Airbnb Rental Income: $2744 Traditional Rental Income: $3404 Airbnb ROI: 1.1% Traditional ROI: 3.64%
168 S Centerville Road Middletown, NY This is one of the Kind property in the Minisink School District . This Beautiful Colonial...	4 beds \| 3 baths \| 3,088 sq.ft.	$710,800	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.34% Airbnb Rental Income: $5817 Traditional Rental Income: $3991 Airbnb ROI: 4.34% Traditional ROI: 3.34%
14 Sunrise Drive Middletown, NY NEW CONSTRUCTION RANCH ON A LOVELY DEAD END STREET! ONE LEVEL LIVING, WITH 3 BEDROOMS, PRI...	3 beds \| 2 baths \| 1,536 sq.ft.	$445,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 3.72% Airbnb Rental Income: $2744 Traditional Rental Income: $2987 Airbnb ROI: 1.59% Traditional ROI: 3.72%
200 Mt Orange Road Middletown, NY Welcome to this most charming 1870's farmhouse situated on idyllic 6.4 level pastoral acr...	4 beds \| 4 baths \| 3,432 sq.ft.	$675,000	Airbnb cash on cash: 4.29% Traditional cash on cash: 3.32% Airbnb Rental Income: $5817 Traditional Rental Income: $4051 Airbnb ROI: 4.29% Traditional ROI: 3.32%
62 New York Avenue Middletown, NY STUNNING home located in a quiet neighborhood of the Town of Wallkill! This home is in min...	5 beds \| 3 baths \| 2,200 sq.ft.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $3609 Airbnb ROI: N/A Traditional ROI: 6.12%
116 Wawayanda Avenue Middletown, NY A perfect colonial home with a Mother - Daughter set up is now under construction in the c...	5 beds \| 4 baths \| 2,850 sq.ft.	$569,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $4009 Airbnb ROI: N/A Traditional ROI: 4.65%
29 Oliver Avenue Middletown, NY Completely renovated in 2023, this move-in ready house boasts a prime location across from...	3 beds \| 2 baths \| 2,013 sq.ft.	$379,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 6.07% Airbnb Rental Income: $2744 Traditional Rental Income: $3232 Airbnb ROI: 2.88% Traditional ROI: 6.07%
39 Hanford Street Middletown, NY Newly renovated 1 Family Home with 5 Bedrooms, and 2,634 SQ.FT, on a quiet and peaceful st...	5 beds \| 2 baths \| 2,634 sq.ft.	$399,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.93% Airbnb Rental Income: $null Traditional Rental Income: $3493 Airbnb ROI: N/A Traditional ROI: 6.93%
40 Camp Orange Road Middletown, NY This versatile and lucrative investment or user property sits on one of the largest open l...	5 beds \| 2 baths \| 2,092 sq.ft.	$2,995,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.08% Airbnb Rental Income: $null Traditional Rental Income: $3405 Airbnb ROI: N/A Traditional ROI: -1.08%
104 Elise Drive Middletown, NY Welcome to The Woodlands at Scotchtown Estates! This exquisite picturesque community sits ...	5 beds \| 4 baths \| 3,700 sq.ft.	$869,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $4169 Airbnb ROI: N/A Traditional ROI: 2.15%
102 Elise Drive Middletown, NY Welcome to The Woodlands at Scotchtown Estates! This exquisite picturesque community sits ...	5 beds \| 4 baths \| 3,700 sq.ft.	$869,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $4169 Airbnb ROI: N/A Traditional ROI: 2.15%
707 Mt Hope Road Middletown, NY Spacious beautiful Ranch home is being built in the town of Wallkill. More finished pictur...	4 beds \| 3 baths \| 2,800 sq.ft.	$649,900	Airbnb cash on cash: 4.82% Traditional cash on cash: 3.28% Airbnb Rental Income: $5817 Traditional Rental Income: $3723 Airbnb ROI: 4.82% Traditional ROI: 3.28%
197 Elise Drive Middletown, NY Welcome to Scotchtown Estates! This exquisite picturesque community sits in the highly sou...	4 beds \| 3 baths \| 3,217 sq.ft.	$779,900	Airbnb cash on cash: 3.6% Traditional cash on cash: 2.03% Airbnb Rental Income: $6131 Traditional Rental Income: $3776 Airbnb ROI: 3.6% Traditional ROI: 2.03%
258 Phillipsburg Road Middletown, NY Attention all investors! Don't miss this incredible opportunity to own a sprawling acreage...	2 beds \| 2 baths \| 1,092 sq.ft.	$345,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 4.39% Airbnb Rental Income: $2603 Traditional Rental Income: $2395 Airbnb ROI: 3.11% Traditional ROI: 4.39%
4 Cherry Street Middletown, NY Classic Large Brick Cape Cod-Style Home for Sale This mother-daughter home sits on a 100 ...	5 beds \| 3 baths \| 2,445 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.52% Airbnb Rental Income: $null Traditional Rental Income: $3162 Airbnb ROI: N/A Traditional ROI: 5.52%
225 Van Duzer Road Middletown, NY Brand-new construction that blends modern design w functionality. The picturesque porch, i...	4 beds \| 3 baths \| 2,900 sq.ft.	$709,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 2.71% Airbnb Rental Income: $5817 Traditional Rental Income: $3676 Airbnb ROI: 4.2% Traditional ROI: 2.71%
22 1/2 Royce Avenue Middletown, NY GORGEOUS Turn-key Middletown home minutes from Presidential schools and YMCA. Front deck w...	3 beds \| 2 baths \| 1,648 sq.ft.	$415,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 3.97% Airbnb Rental Income: $2744 Traditional Rental Income: $2480 Airbnb ROI: 2.99% Traditional ROI: 3.97%
141 Elise Drive Middletown, NY Welcome to Scotchtown Estates! This exquisite picturesque community sits in the highly sou...	4 beds \| 3 baths \| 2,641 sq.ft.	$799,900	Airbnb cash on cash: 3.36% Traditional cash on cash: 1.67% Airbnb Rental Income: $6131 Traditional Rental Income: $3659 Airbnb ROI: 3.36% Traditional ROI: 1.67%
86 Woodlake Drive Unit n/a Middletown, NY Motivated seller! Welcome to this perfect little community. This better than new home has...	3 beds \| 4 baths \| N/A	$385,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 6.4% Airbnb Rental Income: $2744 Traditional Rental Income: $3797 Airbnb ROI: 1.69% Traditional ROI: 6.4%
123 Elise Drive Middletown, NY Welcome to The Woodlands at Scotchtown Estates! This exquisite picturesque community sits ...	5 beds \| 5 baths \| 3,759 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $5419 Airbnb ROI: N/A Traditional ROI: 3.14%
1 Chestnut Street Middletown, NY Calling All Investors. CASH or Rehab loan ONLY! The house needs a full renovation. Call no...	3 beds \| 1 baths \| 1,100 sq.ft.	$239,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 6.43% Airbnb Rental Income: $2744 Traditional Rental Income: $2260 Airbnb ROI: 5.71% Traditional ROI: 6.43%
10 Todd Drive Middletown, NY Nestled in the heart of Middletown, NY, awaits an exquisite colonial-style residence at 10...	4 beds \| 3 baths \| 2,352 sq.ft.	$450,000	Airbnb cash on cash: 8.55% Traditional cash on cash: 5.76% Airbnb Rental Income: $6131 Traditional Rental Income: $3747 Airbnb ROI: 8.55% Traditional ROI: 5.76%
125 Overhill Road Middletown, NY Explore the perfect blend of comfort and convenience at 125 Overhill Rd. in Middletown, Ne...	3 beds \| 1 baths \| 1,408 sq.ft.	$299,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 5.38% Airbnb Rental Income: $2744 Traditional Rental Income: $2472 Airbnb ROI: 4.05% Traditional ROI: 5.38%
52 Hampton Court Middletown, NY Welcome to 52 Hampton Ct in Middletown, NY! As you come inside, you'll be greeted by a sp...	3 beds \| 2 baths \| 1,440 sq.ft.	$285,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 7.37% Airbnb Rental Income: $2744 Traditional Rental Income: $2687 Airbnb ROI: 5.18% Traditional ROI: 7.37%
218 Concord Ln Middletown, NY Welcome to this charming first-floor condo located in Buttonwood Hills community! With 2 b...	2 beds \| 2 baths \| 924 sq.ft.	$239,888	Airbnb cash on cash: 5.8% Traditional cash on cash: 6.87% Airbnb Rental Income: $2603 Traditional Rental Income: $2224 Airbnb ROI: 5.8% Traditional ROI: 6.87%

Real Estate investment in Middletown, NY

There are 117 properties for sale in the city of Middletown . The median list price in Middletown is $389,000 and the average price per square foot is $211. In November 2024, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $2,960.

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

There are 117 investment properties available for sale in Middletown.

In 2024, the best neighborhood to buy investment property is Middletown.

The ROI for Long-Term is higher than the Short-Term in Middletown with average rental income of $2,960.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, NY

179 Reservoir Road

Middletown, NY

3 beds | 2 baths | 3,080 sq.ft.

$699,999

Airbnb cash on cash: 0.45%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $2744

Traditional Rental Income: $3438

Airbnb ROI: 0.45%

Traditional ROI: 2.51%

214 Brown Road

Middletown, NY

3 beds | 4 baths | 2,240 sq.ft.

$695,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2744

Traditional Rental Income: $3765

Airbnb ROI: 0.65%

Traditional ROI: 3.23%

600 Goshen Turnpike

Middletown, NY

3 beds | 3 baths | 2,000 sq.ft.

$490,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $2744

Traditional Rental Income: $3278

Airbnb ROI: 1.52%

Traditional ROI: 4.1%

568 County Route 49 #2C

Middletown, NY

3 beds | 3 baths | 1,593 sq.ft.

$399,900

Airbnb cash on cash: 1.49%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $2744

Traditional Rental Income: $2469

Airbnb ROI: 1.49%

Traditional ROI: 2.48%

36 Putters Way

Middletown, NY

3 beds | 3 baths | 2,690 sq.ft.

$479,900

Airbnb cash on cash: 0.52%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $2744

Traditional Rental Income: $2469

Airbnb ROI: 0.52%

Traditional ROI: 1.35%

358 Concord Lane

Middletown, NY

2 beds | 2 baths | 924 sq.ft.

$224,999

Airbnb cash on cash: 3.72%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $2603

Traditional Rental Income: $2198

Airbnb ROI: 3.72%

Traditional ROI: 4.74%

350 Concord Lane

Middletown, NY

2 beds | 2 baths | 955 sq.ft.

$224,999

Airbnb cash on cash: 3.64%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $2603

Traditional Rental Income: $2198

Airbnb ROI: 3.64%

Traditional ROI: 4.66%

2 Highrose Ridge Way

Middletown, NY

3 beds | 3 baths | 3,057 sq.ft.

$435,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $2744

Traditional Rental Income: $3494

Airbnb ROI: 0.42%