Real Estate Investment Properties for Sale in Howey In The Hills, FL

Looking for investment property in Howey In The Hills, FL with high ROI ?

Explore a variety of short-term homes & houses in Howey In The Hills, FL. Invest wisely with VRBO & Howey In The Hills, FL 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 Howey In The Hills, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
9926 Santa Barbara Ct HOWEY IN THE HILLS, FL Imagine your very own Custom Built, Mediterranean-inspired home, a private cul-de-sac neig...	4 beds \| 3 baths \| 2,431 sq.ft.	$639,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.19% Airbnb Rental Income: $1558 Traditional Rental Income: $3341 Airbnb ROI: -0.55% Traditional ROI: 3.19%
9616 San Fernando Ct HOWEY IN THE HILLS, FL Welcome to 9616 San Fernando Court, an elegant pool home offering 3,650 square feet of liv...	4 beds \| 3 baths \| 3,650 sq.ft.	$1,125,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 1.29% Airbnb Rental Income: $1558 Traditional Rental Income: $3359 Airbnb ROI: -0.86% Traditional ROI: 1.29%
9513 SERRA Court HOWEY IN THE HILLS, FL (Video under Zillow Facts & Features) WELCOME TO THE MISSION RESORT's GATED LAS COLINAS GO...	2 beds \| 2 baths \| 1,691 sq.ft.	$408,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.29% Airbnb Rental Income: $1512 Traditional Rental Income: $2031 Airbnb ROI: -0.22% Traditional ROI: 2.29%
9429 San Miguel HOWEY IN THE HILLS, FL Leave the ordinary behind and retreat to your own private oasis in the prestigious Mission...	4 beds \| 2 baths \| 1,932 sq.ft.	$684,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 1.82% Airbnb Rental Income: $1558 Traditional Rental Income: $2210 Airbnb ROI: 0.1% Traditional ROI: 1.82%
314 Dupont Cir HOWEY IN THE HILLS, FL Virtually Staged. Welcome to 314 Dupont Cir, a residence presenting a fresh interior paint...	3 beds \| 2 baths \| 1,679 sq.ft.	$350,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 4.25% Airbnb Rental Income: $1918 Traditional Rental Income: $2066 Airbnb ROI: 2.25% Traditional ROI: 4.25%
245 MESSINA Place HOWEY IN THE HILLS, FL MODERN LUXURY 4 BED/2 BATH CUSTOM HOME in coveted HOWEY IN THE HILLS! Bright, Spacious & O...	4 beds \| 2 baths \| 1,910 sq.ft.	$375,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.83% Airbnb Rental Income: $1558 Traditional Rental Income: $2444 Airbnb ROI: 0.03% Traditional ROI: 3.83%
112 E Gardenia St HOWEY IN THE HILLS, FL PRICE REDUCTION. Nesteled in the quaint and charming town of Howey-in-the-Hills and just a...	4 beds \| 4 baths \| 4,312 sq.ft.	$575,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 3.39% Airbnb Rental Income: $1558 Traditional Rental Income: $3434 Airbnb ROI: -0.94% Traditional ROI: 3.39%
802 CAMINO REAL Boulevard #802 HOWEY IN THE HILLS, FL MASSIVE PRICE REDUCTION!! Seller motivated!! Welcome Home to the ultimate Florida lifestyl...	3 beds \| 2 baths \| 1,824 sq.ft.	$250,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 5.08% Airbnb Rental Income: $1918 Traditional Rental Income: $2588 Airbnb ROI: 0.09% Traditional ROI: 5.08%
528 BELLISSIMO Place HOWEY IN THE HILLS, FL Imagine 528 Bellissimo Pl, where everyday comfort and practicality blend seamlessly. The k...	4 beds \| 2 baths \| 1,880 sq.ft.	$370,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 4.99% Airbnb Rental Income: $1558 Traditional Rental Income: $2684 Airbnb ROI: 0.45% Traditional ROI: 4.99%
54 CAMINO REAL Boulevard #504 HOWEY IN THE HILLS, FL BEAUTIFUL CONDO WITH RECENT HUGE PRICE REDUCTION!! SELLER MOTIVATED!! DO NOT LET THIS OPPO...	3 beds \| 3 baths \| 2,686 sq.ft.	$300,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 7.94% Airbnb Rental Income: $1918 Traditional Rental Income: $4078 Airbnb ROI: -1.51% Traditional ROI: 7.94%
965 LIDO Drive HOWEY IN THE HILLS, FL Price Improvement! Beautiful, move-in ready 3BR/2.5BA plus loft townhome in the tranquil V...	3 beds \| 3 baths \| 1,660 sq.ft.	$290,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.44% Airbnb Rental Income: $1918 Traditional Rental Income: $2264 Airbnb ROI: 1.31% Traditional ROI: 4.44%
1026 Lido Dr HOWEY IN THE HILLS, FL New Improved Price! This charming spacious 3-bed, 2.5-bath townhome nestled in a establish...	3 beds \| 2 baths \| 1,660 sq.ft.	$203,900	Airbnb cash on cash: 2.48% Traditional cash on cash: 6.97% Airbnb Rental Income: $1918 Traditional Rental Income: $2277 Airbnb ROI: 2.48% Traditional ROI: 6.97%
9958 SANTA BARBARA Court HOWEY IN THE HILLS, FL Virtually Staged. PRICE Just REDUCED!!! ALL NEW INTERIOR PAINT AND CARPET!! PARADISE AWAIT...	3 beds \| 3 baths \| 2,107 sq.ft.	$454,900	Airbnb cash on cash: 0.12% Traditional cash on cash: 4% Airbnb Rental Income: $1918 Traditional Rental Income: $3062 Airbnb ROI: 0.12% Traditional ROI: 4%
1219 Lido Dr HOWEY IN THE HILLS, FL Welcome to Venezia Townhomes, a charming new community by D.R. Horton located in picturesq...	3 beds \| 2 baths \| 1,660 sq.ft.	$296,999	Airbnb cash on cash: 1.53% Traditional cash on cash: 5.02% Airbnb Rental Income: $1918 Traditional Rental Income: $2387 Airbnb ROI: 1.53% Traditional ROI: 5.02%
709 Calabria Way HOWEY IN THE HILLS, FL Welcome home to this well-maintained three bedroom 2 1/2 bath, open concept, single-owner ...	3 beds \| 2 baths \| 1,899 sq.ft.	$400,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 4.85% Airbnb Rental Income: $1918 Traditional Rental Income: $2647 Airbnb ROI: 1.55% Traditional ROI: 4.85%
103 CAMINO REAL Boulevard HOWEY IN THE HILLS, FL Virtually Staged. Wake up surrounded by palm trees, world-class golf, and the peaceful rhy...	3 beds \| 2 baths \| 2,010 sq.ft.	$259,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 5.56% Airbnb Rental Income: $1918 Traditional Rental Income: $2792 Airbnb ROI: -0.07% Traditional ROI: 5.56%
24540 Turkey Lake Rd HOWEY IN THE HILLS, FL Discover timeless elegance and exceptional privacy in this custom-built 3-bedroom, 3-bath ...	3 beds \| 3 baths \| 2,984 sq.ft.	$999,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 3% Airbnb Rental Income: $1918 Traditional Rental Income: $4225 Airbnb ROI: -0.02% Traditional ROI: 3%
26345 San Gabriel HOWEY IN THE HILLS, FL Ready to spend your next winter in warmer tropical places where you can play golf and fish...	3 beds \| 2 baths \| 2,138 sq.ft.	$519,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 1.03% Airbnb Rental Income: $1918 Traditional Rental Income: $1888 Airbnb ROI: 0.05% Traditional ROI: 1.03%
26207 Avenida Las Colinas HOWEY IN THE HILLS, FL Virtually Staged. Experience true resort-style living in this beautifully appointed first-...	2 beds \| 2 baths \| 2,031 sq.ft.	$299,000	Airbnb cash on cash: -2.1% Traditional cash on cash: 4.56% Airbnb Rental Income: $1512 Traditional Rental Income: $2947 Airbnb ROI: -2.1% Traditional ROI: 4.56%
102 Camino Real Blvd #102 HOWEY IN THE HILLS, FL Discover peaceful resort-style living in the beautiful Mission Inn Resort & Club community...	2 beds \| 2 baths \| 1,628 sq.ft.	$275,000	Airbnb cash on cash: -2.22% Traditional cash on cash: 3.86% Airbnb Rental Income: $1512 Traditional Rental Income: $2647 Airbnb ROI: -2.22% Traditional ROI: 3.86%
523 BELLISSIMO Place HOWEY IN THE HILLS, FL Virtually Staged. NEW LOWER PRICE PLUS...Seller is providing a home warranty for $1000 fro...	4 beds \| 3 baths \| 2,565 sq.ft.	$430,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 5.36% Airbnb Rental Income: $1558 Traditional Rental Income: $3017 Airbnb ROI: 0.62% Traditional ROI: 5.36%
26206 Avenida Las Colinas #4A HOWEY IN THE HILLS, FL Huge Price Drop!! Schedule your showing today!! This fantastic DEAL won't last long!! LUXU...	2 beds \| 2 baths \| 2,031 sq.ft.	$299,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 3.66% Airbnb Rental Income: $1512 Traditional Rental Income: $2579 Airbnb ROI: -1.7% Traditional ROI: 3.66%
1041 Lido Dr HOWEY IN THE HILLS, FL One or more photo(s) has been virtually staged. Looking for low maintenance townhome livin...	3 beds \| 2 baths \| 1,673 sq.ft.	$290,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 6.94% Airbnb Rental Income: $1918 Traditional Rental Income: $2443 Airbnb ROI: 3.16% Traditional ROI: 6.94%
8108 Sergeant Pepper Dr HOWEY IN THE HILLS, FL Back to the Market * Financing Falls Through * This Cozy and well-maintained home offe...	3 beds \| 2 baths \| 1,296 sq.ft.	$359,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 2.83% Airbnb Rental Income: $1918 Traditional Rental Income: $1720 Airbnb ROI: 1.91% Traditional ROI: 2.83%
901 Camino Real Blvd #901 HOWEY IN THE HILLS, FL Virtually Staged. Experience resort living at its finest with this beautifully maintained ...	3 beds \| 2 baths \| 1,824 sq.ft.	$285,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 4.54% Airbnb Rental Income: $1918 Traditional Rental Income: $2650 Airbnb ROI: -0.08% Traditional ROI: 4.54%
23449 Thomas Allen Rd HOWEY IN THE HILLS, FL Nestled at the end of a private road on 10 expansive agriculturally zoned acres, this stun...	4 beds \| 3 baths \| 2,632 sq.ft.	$499,990	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.28% Airbnb Rental Income: $1558 Traditional Rental Income: $2551 Airbnb ROI: 0.19% Traditional ROI: 3.28%
900 N Citrus Ave HOWEY IN THE HILLS, FL Discover a rare opportunity in the heart of historic Howey-in-the-Hills! This stunning cus...	4 beds \| 3 baths \| 3,212 sq.ft.	$799,999	Airbnb cash on cash: -0.89% Traditional cash on cash: 1.59% Airbnb Rental Income: $1558 Traditional Rental Income: $3073 Airbnb ROI: -0.89% Traditional ROI: 1.59%
27421 BLACK KITE Avenue HOWEY IN THE HILLS, FL Come home to more space, more comfort, and the Florida lifestyle you've been looking for i...	5 beds \| 3 baths \| 2,182 sq.ft.	$359,990	Airbnb cash on cash: N/A Traditional cash on cash: 5.91% Airbnb Rental Income: $null Traditional Rental Income: $2816 Airbnb ROI: N/A Traditional ROI: 5.91%
600 Avila Pl HOWEY IN THE HILLS, FL SELLER IS OFFERING UP TO $10,000 TOWARD BUYER CLOSING COSTS, prepaid expenses, or an inter...	4 beds \| 3 baths \| 2,514 sq.ft.	$523,900	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.39% Airbnb Rental Income: $1558 Traditional Rental Income: $2816 Airbnb ROI: -0.1% Traditional ROI: 3.39%
700 S Florida Ave HOWEY IN THE HILLS, FL Welcome to this beautifully designed 2019 custom-built home, offering an impressive combin...	3 beds \| 2 baths \| 2,359 sq.ft.	$643,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 2.85% Airbnb Rental Income: $1918 Traditional Rental Income: $2702 Airbnb ROI: 0.7% Traditional ROI: 2.85%
9939 Santa Barbara Ct HOWEY IN THE HILLS, FL Welcome to this beautifully maintained 3-bedroom, 3-bath home with a dedicated den, offeri...	3 beds \| 3 baths \| 2,402 sq.ft.	$625,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.96% Airbnb Rental Income: $1918 Traditional Rental Income: $3284 Airbnb ROI: -0.25% Traditional ROI: 2.96%
9219 San Jose Blvd HOWEY IN THE HILLS, FL CUSTOM-BUILT LUXURY VILLA \| SPECTACULAR OUTDOOR KITCHEN \| POND & GOLF COURSE VIEWS Welcome...	3 beds \| 2 baths \| 2,072 sq.ft.	$610,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 2.67% Airbnb Rental Income: $1918 Traditional Rental Income: $3013 Airbnb ROI: -0.15% Traditional ROI: 2.67%

Real Estate investment in Howey-in-the-hills, FL

There are 65 properties for sale in the city of Howey In The Hills . The median list price in Howey In The Hills is $404,000 and the average price per square foot is $182. In September 2026, the average monthly cash on cash return in Howey In The Hills is 4.00%. The average monthly rental income in Howey In The Hills is $2,702.

Howey-in-the-hills, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 65 investment properties available for sale in Howey-in-the-hills.

In 2026, the best neighborhood to buy investment property is HOWEY IN THE HILLS.

The ROI for Short-Term is higher than the Long-Term in Howey-in-the-hills with average rental income of $1,738.

Your search for investment property begins and ends here

Investment Property for Sale in Howey In The Hills, FL

9926 Santa Barbara Ct

HOWEY IN THE HILLS, FL

4 beds | 3 baths | 2,431 sq.ft.

$639,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1558

Traditional Rental Income: $3341

Airbnb ROI: -0.55%

Traditional ROI: 3.19%

9616 San Fernando Ct

HOWEY IN THE HILLS, FL

4 beds | 3 baths | 3,650 sq.ft.

$1,125,000

Airbnb cash on cash: -0.86%

Traditional cash on cash: 1.29%

Airbnb Rental Income: $1558

Traditional Rental Income: $3359

Airbnb ROI: -0.86%

Traditional ROI: 1.29%

9513 SERRA Court

HOWEY IN THE HILLS, FL

2 beds | 2 baths | 1,691 sq.ft.

$408,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $1512

Traditional Rental Income: $2031

Airbnb ROI: -0.22%

Traditional ROI: 2.29%

9429 San Miguel

HOWEY IN THE HILLS, FL

4 beds | 2 baths | 1,932 sq.ft.

$684,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 1.82%

Airbnb Rental Income: $1558

Traditional Rental Income: $2210

Airbnb ROI: 0.1%

Traditional ROI: 1.82%

314 Dupont Cir

HOWEY IN THE HILLS, FL

3 beds | 2 baths | 1,679 sq.ft.

$350,000

Airbnb cash on cash: 2.25%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $1918

Traditional Rental Income: $2066

Airbnb ROI: 2.25%

Traditional ROI: 4.25%

245 MESSINA Place

HOWEY IN THE HILLS, FL

4 beds | 2 baths | 1,910 sq.ft.

$375,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $1558

Traditional Rental Income: $2444

Airbnb ROI: 0.03%

Traditional ROI: 3.83%

112 E Gardenia St

HOWEY IN THE HILLS, FL

4 beds | 4 baths | 4,312 sq.ft.

$575,000

Airbnb cash on cash: -0.94%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $1558

Traditional Rental Income: $3434

Airbnb ROI: -0.94%

Traditional ROI: 3.39%

802 CAMINO REAL Boulevard #802

HOWEY IN THE HILLS, FL

3 beds | 2 baths | 1,824 sq.ft.

$250,000

Airbnb cash on cash: 0.09%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $1918

Traditional Rental Income: $2588

Airbnb ROI: 0.09%