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 COURT 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: 1.81% Traditional cash on cash: 3.46% Airbnb Rental Income: $3059 Traditional Rental Income: $3341 Airbnb ROI: 1.81% Traditional ROI: 3.46%
9326 SAN JOSE BLVD HOWEY IN THE HILLS, FL Enjoy a quiet, active lifestyle at Las Colinas in the Mission Inn Resort and Club. Set in ...	3 beds \| 3 baths \| 2,648 sq.ft.	$659,900	Airbnb cash on cash: 1.73% Traditional cash on cash: 2.75% Airbnb Rental Income: $3164 Traditional Rental Income: $3074 Airbnb ROI: 1.73% Traditional ROI: 2.75%
131 E PALMETTO AVENUE HOWEY IN THE HILLS, FL One or more photo(s) has been virtually staged. Welcome to your own slice of small-town ch...	3 beds \| 3 baths \| 1,894 sq.ft.	$335,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 6.64% Airbnb Rental Income: $3164 Traditional Rental Income: $3092 Airbnb ROI: 4.6% Traditional ROI: 6.64%
699 S DIXIE DRIVE HOWEY IN THE HILLS, FL Under contract-accepting backup offers. Move-in ready and thoughtfully designed, this sing...	3 beds \| 2 baths \| 1,651 sq.ft.	$385,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 4.71% Airbnb Rental Income: $3164 Traditional Rental Income: $2429 Airbnb ROI: 4.77% Traditional ROI: 4.71%
436 Bellissimo Pl HOWEY IN THE HILLS, FL 2017-Almost New! This gorgeous home w/stone exterior, brick paver driveway, greets you wit...	4 beds \| 3 baths \| 2,369 sq.ft.	$440,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.67% Airbnb Rental Income: $3059 Traditional Rental Income: $2625 Airbnb ROI: 3.03% Traditional ROI: 3.67%
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.	$689,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 1.8% Airbnb Rental Income: $3059 Traditional Rental Income: $2210 Airbnb ROI: 2.04% Traditional ROI: 1.8%
25101 Turkey Lake Rd HOWEY IN THE HILLS, FL Fall in love with this alluring property and beautiful custom-built home. This must-see h...	4 beds \| 3 baths \| 2,066 sq.ft.	$849,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 1.69% Airbnb Rental Income: $3059 Traditional Rental Income: $2447 Airbnb ROI: 1.58% Traditional ROI: 1.69%
9220 SAN JOSE BOULEVARD HOWEY IN THE HILLS, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	3 beds \| 2 baths \| 1,971 sq.ft.	$487,500	Airbnb cash on cash: 2.7% Traditional cash on cash: 3.57% Airbnb Rental Income: $3164 Traditional Rental Income: $2846 Airbnb ROI: 2.7% Traditional ROI: 3.57%
602 Napoli Way HOWEY IN THE HILLS, FL One or more photo(s) has been virtually staged. Rare opportunity with an assumable VA loan...	3 beds \| 2 baths \| 1,664 sq.ft.	$380,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 4.38% Airbnb Rental Income: $3164 Traditional Rental Income: $2448 Airbnb ROI: 4.38% Traditional ROI: 4.38%
245 Messina Pl HOWEY IN THE HILLS, FL Why wait for a new build? Buy a new home now! Welcome home to 245 Messina Place. This beau...	4 beds \| 2 baths \| 1,910 sq.ft.	$379,999	Airbnb cash on cash: 4.93% Traditional cash on cash: 5.17% Airbnb Rental Income: $3059 Traditional Rental Income: $2444 Airbnb ROI: 4.93% Traditional ROI: 5.17%
575 Avila Pl HOWEY IN THE HILLS, FL Amazing 4 bedroom 3 full bathroom one story home in the beautiful neighborhood of Talichet...	4 beds \| 3 baths \| 2,510 sq.ft.	$489,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 3.88% Airbnb Rental Income: $3059 Traditional Rental Income: $3171 Airbnb ROI: 2.11% Traditional ROI: 3.88%
121 E Pine St HOWEY IN THE HILLS, FL Welcome home!! This property is a must see and has so much to offer your family! Beginning...	3 beds \| 2 baths \| 2,088 sq.ft.	$385,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.58% Airbnb Rental Income: $3164 Traditional Rental Income: $2294 Airbnb ROI: 5.01% Traditional ROI: 4.58%
236 MESSINA PL HOWEY IN THE HILLS, FL Welcome to effortless Florida living in the heart of Howey-in-the-Hills. This beautifully ...	4 beds \| 2 baths \| 1,780 sq.ft.	$379,500	Airbnb cash on cash: 5.07% Traditional cash on cash: 5.43% Airbnb Rental Income: $3059 Traditional Rental Income: $2489 Airbnb ROI: 5.07% Traditional ROI: 5.43%
594 VIA BELLA COURT HOWEY IN THE HILLS, FL Under contract-accepting backup offers. Motivated sellers. Over $100,000 in improvements o...	4 beds \| 3 baths \| 3,038 sq.ft.	$520,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 4.16% Airbnb Rental Income: $3059 Traditional Rental Income: $3479 Airbnb ROI: 1.86% Traditional ROI: 4.16%
591 Via Bella Ct HOWEY IN THE HILLS, FL Under Construction. Stock Images Biscayne Elevation B, Lot 103 Extra Large Pie Shaped Lot...	4 beds \| 3 baths \| 3,020 sq.ft.	$535,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 5.11% Airbnb Rental Income: $3059 Traditional Rental Income: $3343 Airbnb ROI: 3.14% Traditional ROI: 5.11%
14 Camino Real Blvd #14 HOWEY IN THE HILLS, FL Spacious, Light-Filled Condo with Water Views in Prestigious Mission Inn Resort! Step i...	3 beds \| 2 baths \| 2,685 sq.ft.	$525,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 2.41% Airbnb Rental Income: $3164 Traditional Rental Income: $2912 Airbnb ROI: 1.46% Traditional ROI: 2.41%
802 CAMINO REAL BOULEVARD #802 HOWEY IN THE HILLS, FL Price Reduced!! Welcome Home to the ultimate Florida lifestyle at Mission Inn! Enjoy brea...	3 beds \| 2 baths \| 1,824 sq.ft.	$275,000	Airbnb cash on cash: 4% Traditional cash on cash: 4.54% Airbnb Rental Income: $3164 Traditional Rental Income: $2588 Airbnb ROI: 4% Traditional ROI: 4.54%
405 LONG AND WINDING ROAD HOWEY IN THE HILLS, FL Luxury Custom Estate Home in Blue Spring Reserve Experience upscale living in the gated c...	4 beds \| 5 baths \| 4,231 sq.ft.	$1,650,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.27% Airbnb Rental Income: $3059 Traditional Rental Income: $6865 Airbnb ROI: 0.33% Traditional ROI: 3.27%
25921 SAN RAFAEL COURT HOWEY IN THE HILLS, FL Short Sale. Welcome to the Las Colinas neighborhood of San Rafael. This Golf Course Villa ...	3 beds \| 2 baths \| 1,942 sq.ft.	$350,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 5.61% Airbnb Rental Income: $3164 Traditional Rental Income: $2763 Airbnb ROI: 4.65% Traditional ROI: 5.61%
528 BELLISSIMO PLACE HOWEY IN THE HILLS, FL One or more photo(s) has been virtually staged. Imagine 528 Bellissimo Pl, where everyday ...	4 beds \| 2 baths \| 1,880 sq.ft.	$375,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 4.91% Airbnb Rental Income: $3059 Traditional Rental Income: $2684 Airbnb ROI: 3.99% Traditional ROI: 4.91%
961 LIDO DRIVE HOWEY IN THE HILLS, FL A stunning two-story townhome floor plan within the Venezia community in Howey-in-the-Hill...	3 beds \| 3 baths \| 1,758 sq.ft.	$289,500	Airbnb cash on cash: 5.1% Traditional cash on cash: 5.19% Airbnb Rental Income: $3164 Traditional Rental Income: $2473 Airbnb ROI: 5.1% Traditional ROI: 5.19%
9930 SANTA BARBARA COURT HOWEY IN THE HILLS, FL Experience golf and resort living at its finest in the exclusive gated neighborhood of Las...	3 beds \| 2 baths \| 1,885 sq.ft.	$456,500	Airbnb cash on cash: 3.04% Traditional cash on cash: 3.8% Airbnb Rental Income: $3164 Traditional Rental Income: $2772 Airbnb ROI: 3.04% Traditional ROI: 3.8%
54 CAMINO REAL BOULEVARD #504 HOWEY IN THE HILLS, FL Experience Luxurious Resort Living with Majestic Golf Course Views* Discover the tranqui...	3 beds \| 3 baths \| 2,686 sq.ft.	$425,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 5.34% Airbnb Rental Income: $3164 Traditional Rental Income: $4078 Airbnb ROI: 1.25% Traditional ROI: 5.34%
1026 LIDO DRIVE HOWEY IN THE HILLS, FL Reduced $!4K. This charming spacious 3-bed, 2.5-bath townhome nestled in a established ...	3 beds \| 3 baths \| 1,660 sq.ft.	$248,000	Airbnb cash on cash: 6.31% Traditional cash on cash: 5.59% Airbnb Rental Income: $3164 Traditional Rental Income: $2277 Airbnb ROI: 6.31% Traditional ROI: 5.59%
9958 SANTA BARBARA COURT HOWEY IN THE HILLS, FL One or more photo(s) has been virtually staged. PRICE Just REDUCED!!! ALL NEW INTERIOR PAI...	3 beds \| 3 baths \| 2,107 sq.ft.	$454,900	Airbnb cash on cash: 2.55% Traditional cash on cash: 3.99% Airbnb Rental Income: $3164 Traditional Rental Income: $3062 Airbnb ROI: 2.55% Traditional ROI: 3.99%
1219 LIDO DRIVE HOWEY IN THE HILLS, FL Welcome to Venezia Townhomes, a charming new community by D.R. Horton located in picturesq...	3 beds \| 3 baths \| 1,660 sq.ft.	$296,999	Airbnb cash on cash: 5.28% Traditional cash on cash: 5.06% Airbnb Rental Income: $3164 Traditional Rental Income: $2387 Airbnb ROI: 5.28% Traditional ROI: 5.06%
9307 San Jose Blvd HOWEY IN THE HILLS, FL Under contract-accepting backup offers. Huge price reduction! Now $560,000, come and see t...	3 beds \| 2 baths \| 1,971 sq.ft.	$525,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 2.69% Airbnb Rental Income: $3164 Traditional Rental Income: $2536 Airbnb ROI: 2.51% Traditional ROI: 2.69%
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 \| 3 baths \| 1,899 sq.ft.	$400,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 4.85% Airbnb Rental Income: $3164 Traditional Rental Income: $2647 Airbnb ROI: 4.32% Traditional ROI: 4.85%
103 CAMINO REAL BOULEVARD HOWEY IN THE HILLS, FL One or more photo(s) has been virtually staged. Wake up surrounded by palm trees, world-cl...	3 beds \| 2 baths \| 2,010 sq.ft.	$265,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 5.44% Airbnb Rental Income: $3164 Traditional Rental Income: $2792 Airbnb ROI: 4.06% Traditional ROI: 5.44%
24540 TURKEY LAKE ROAD 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.	$1,150,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.48% Airbnb Rental Income: $3164 Traditional Rental Income: $4225 Airbnb ROI: 0.82% Traditional ROI: 2.48%
708 Santa Cruz Ln #708 HOWEY IN THE HILLS, FL 708 Santa Cruz Ln #708, HOWEY IN THE HILLS, FL 34737 \| Condo/Coop	2 beds \| 2 baths \| 1,330 sq.ft.	$229,000	Airbnb cash on cash: -2.52% Traditional cash on cash: 3.48% Airbnb Rental Income: $1106 Traditional Rental Income: $2032 Airbnb ROI: -2.52% Traditional ROI: 3.48%
26345 SAN GABRIEL HOWEY IN THE HILLS, FL Discover timeless elegance and resort-style living at 26345 San Gabriel, nestled in the La...	3 beds \| 2 baths \| 2,138 sq.ft.	$539,995	Airbnb cash on cash: 2.1% Traditional cash on cash: 0.99% Airbnb Rental Income: $3164 Traditional Rental Income: $1888 Airbnb ROI: 2.1% Traditional ROI: 0.99%
26207 Avenida Las Colinas HOWEY IN THE HILLS, FL 26207 Avenida Las Colinas, HOWEY IN THE HILLS, FL 34737 \| Condo/Coop	2 beds \| 2 baths \| 2,031 sq.ft.	$359,900	Airbnb cash on cash: -2.48% Traditional cash on cash: 4.08% Airbnb Rental Income: $1106 Traditional Rental Income: $2947 Airbnb ROI: -2.48% Traditional ROI: 4.08%
1198 Lido Dr HOWEY IN THE HILLS, FL 1198 Lido Dr, HOWEY IN THE HILLS, FL 34737 \| Townhouse	3 beds \| 2 baths \| 1,660 sq.ft.	$279,900	Airbnb cash on cash: 6.47% Traditional cash on cash: 6.62% Airbnb Rental Income: $3164 Traditional Rental Income: $2487 Airbnb ROI: 6.47% Traditional ROI: 6.62%
102 CAMINO REAL BOULEVARD #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: -3.53% Traditional cash on cash: 3.86% Airbnb Rental Income: $1106 Traditional Rental Income: $2647 Airbnb ROI: -3.53% Traditional ROI: 3.86%
S Dewey Robbins Rd HOWEY IN THE HILLS, FL S Dewey Robbins Rd, HOWEY IN THE HILLS, FL 34737 \| Other	N/A beds \| N/A baths \| N/A	$375,900	Airbnb cash on cash: 2.02% Traditional cash on cash: 1.82% Airbnb Rental Income: $1992 Traditional Rental Income: $1399 Airbnb ROI: 2.02% Traditional ROI: 1.82%
24207 Turkey Lake Rd HOWEY IN THE HILLS, FL 24207 Turkey Lake Rd, HOWEY IN THE HILLS, FL 34737 \| Manufactured Home	N/A beds \| N/A baths \| 1,830 sq.ft.	$329,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 5.52% Airbnb Rental Income: $1992 Traditional Rental Income: $2382 Airbnb ROI: 2.57% Traditional ROI: 5.52%
7086 Number Two Rd HOWEY IN THE HILLS, FL 7086 Number Two Rd, HOWEY IN THE HILLS, FL 34737 \| Single Family Residential	3 beds \| 2 baths \| 3,177 sq.ft.	$998,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 1.48% Airbnb Rental Income: $3164 Traditional Rental Income: $3221 Airbnb ROI: 0.65% Traditional ROI: 1.48%
9509 San Fernando Ct HOWEY IN THE HILLS, FL 9509 San Fernando Ct, HOWEY IN THE HILLS, FL 34737 \| Other	N/A beds \| N/A baths \| N/A	$115,000	Airbnb cash on cash: 9.03% Traditional cash on cash: 7.18% Airbnb Rental Income: $1992 Traditional Rental Income: $1266 Airbnb ROI: 9.03% Traditional ROI: 7.18%
523 BELLISSIMO PLACE HOWEY IN THE HILLS, FL Welcome home to this beautiful four-bedroom, three-bath residence nestled on a prime corne...	4 beds \| 3 baths \| 2,565 sq.ft.	$449,999	Airbnb cash on cash: 3.52% Traditional cash on cash: 5.08% Airbnb Rental Income: $3059 Traditional Rental Income: $3017 Airbnb ROI: 3.52% Traditional ROI: 5.08%

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

There are 64 properties for sale in the city of Howey In The Hills . The median list price in Howey In The Hills is $384,950 and the average price per square foot is $179. In June 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 $2,579.

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

There are 64 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 Long-Term is higher than the Short-Term in Howey-in-the-hills with average rental income of $2,579.

Your search for investment property begins and ends here

Investment Property for Sale in Howey In The Hills, FL

9926 SANTA BARBARA COURT

HOWEY IN THE HILLS, FL

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

$639,000

Airbnb cash on cash: 1.81%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $3059

Traditional Rental Income: $3341

Airbnb ROI: 1.81%

Traditional ROI: 3.46%

9326 SAN JOSE BLVD

HOWEY IN THE HILLS, FL

3 beds | 3 baths | 2,648 sq.ft.

$659,900

Airbnb cash on cash: 1.73%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $3164

Traditional Rental Income: $3074

Airbnb ROI: 1.73%

Traditional ROI: 2.75%

131 E PALMETTO AVENUE

HOWEY IN THE HILLS, FL

3 beds | 3 baths | 1,894 sq.ft.

$335,000

Airbnb cash on cash: 4.6%

Traditional cash on cash: 6.64%

Airbnb Rental Income: $3164

Traditional Rental Income: $3092

Airbnb ROI: 4.6%

Traditional ROI: 6.64%

699 S DIXIE DRIVE

HOWEY IN THE HILLS, FL

3 beds | 2 baths | 1,651 sq.ft.

$385,000

Airbnb cash on cash: 4.77%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $3164

Traditional Rental Income: $2429

Airbnb ROI: 4.77%

Traditional ROI: 4.71%

436 Bellissimo Pl

HOWEY IN THE HILLS, FL

4 beds | 3 baths | 2,369 sq.ft.

$440,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $3059

Traditional Rental Income: $2625

Airbnb ROI: 3.03%

Traditional ROI: 3.67%

9429 SAN MIGUEL

HOWEY IN THE HILLS, FL

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

$689,000

Airbnb cash on cash: 2.04%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $3059

Traditional Rental Income: $2210

Airbnb ROI: 2.04%

Traditional ROI: 1.8%

25101 Turkey Lake Rd

HOWEY IN THE HILLS, FL

4 beds | 3 baths | 2,066 sq.ft.

$849,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 1.69%

Airbnb Rental Income: $3059

Traditional Rental Income: $2447

Airbnb ROI: 1.58%

Traditional ROI: 1.69%

9220 SAN JOSE BOULEVARD

HOWEY IN THE HILLS, FL

3 beds | 2 baths | 1,971 sq.ft.

$487,500

Airbnb cash on cash: 2.7%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $3164

Traditional Rental Income: $2846

Airbnb ROI: 2.7%