Real Estate Investment Properties for Sale in Chiefland, FL

Looking for investment property in Chiefland, FL with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2691 NW 74th Ter Chiefland, FL WELCOME to this Beautifully Upgraded Chiefland Home 3/2 home situated on 0.24 acres in Chi...	3 beds \| 2 baths \| 1,812 sq.ft.	$154,900	Airbnb cash on cash: 8.12% Traditional cash on cash: 9.15% Airbnb Rental Income: $2093 Traditional Rental Income: $1708 Airbnb ROI: 8.12% Traditional ROI: 9.15%
1108 SW 2ND Avenue Chiefland, FL Beautifully remodeled, MOVE IN READY retreat nestled on nearly a full acre in the quiet ru...	3 beds \| 2 baths \| 1,572 sq.ft.	$300,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 4.66% Airbnb Rental Income: $2093 Traditional Rental Income: $2008 Airbnb ROI: 3.05% Traditional ROI: 4.66%
308 SW 2ND Avenue Chiefland, FL Price improvement , special incentive being offered with Preferred Lender * Amazing 3 bedr...	3 beds \| 2 baths \| 1,163 sq.ft.	$217,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 1.8% Airbnb Rental Income: $2093 Traditional Rental Income: $945 Airbnb ROI: 4.77% Traditional ROI: 1.8%
3551 NW 60th Ave Chiefland, FL COUNTRY DREAMS COME TRUE ~ Chiefland, FL 10-acre fully-fenced farm ~ Welcome home to a pla...	3 beds \| 2 baths \| 2,195 sq.ft.	$499,900	Airbnb cash on cash: 1.67% Traditional cash on cash: 0.83% Airbnb Rental Income: $2093 Traditional Rental Income: $1162 Airbnb ROI: 1.67% Traditional ROI: 0.83%
1191 NW 120th St Chiefland, FL PRICE REDUCED!!!! Seller motivated. Property back on the market due to previous contract c...	2 beds \| 2 baths \| 2,000 sq.ft.	$499,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 3.31% Airbnb Rental Income: $644 Traditional Rental Income: $2387 Airbnb ROI: -1.06% Traditional ROI: 3.31%
4651 NE 108TH Place Chiefland, FL LOCATION! WINDING RIVER PRESERVE Come and enjoy all the outdoors has to offer, hunting, fi...	3 beds \| 2 baths \| 912 sq.ft.	$675,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 1.46% Airbnb Rental Income: $2093 Traditional Rental Income: $1903 Airbnb ROI: 0.91% Traditional ROI: 1.46%
5590 NW 76th Avenue Chiefland, FL Welcome to peaceful country living in Chiefland, Florida! This well-maintained 2 bedroom, ...	2 beds \| 2 baths \| 924 sq.ft.	$199,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 6.67% Airbnb Rental Income: $644 Traditional Rental Income: $1723 Airbnb ROI: -0.61% Traditional ROI: 6.67%
9492 NW 46th Pl Chiefland, FL Make an appointment to view this beautiful cedar home located in the center of 5 acres of ...	3 beds \| 3 baths \| 3,818 sq.ft.	$650,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 4.46% Airbnb Rental Income: $2093 Traditional Rental Income: $3443 Airbnb ROI: 1.34% Traditional ROI: 4.46%
10151 NW 70TH Street Chiefland, FL A Private Slice of Paradise on 73 Acres of Elegance and Serenity Welcome to your dream...	4 beds \| 5 baths \| 2,898 sq.ft.	$1,840,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 1.81% Airbnb Rental Income: $6815 Traditional Rental Income: $5800 Airbnb ROI: 1.63% Traditional ROI: 1.81%
7251 NW 40TH Street Chiefland, FL Bring the horses, the chickens, the equipment, and the toys. This high-and-dry 2.5-acre Ch...	3 beds \| 3 baths \| 1,723 sq.ft.	$379,900	Airbnb cash on cash: 2.35% Traditional cash on cash: 4.92% Airbnb Rental Income: $2093 Traditional Rental Income: $2470 Airbnb ROI: 2.35% Traditional ROI: 4.92%
10150 NW 35th Ave Chiefland, FL Discover country living at its best with this 3-bedroom, 2-bath home situated on 16 beauti...	3 beds \| 2 baths \| 1,800 sq.ft.	$400,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 5.4% Airbnb Rental Income: $2093 Traditional Rental Income: $2499 Airbnb ROI: 2.88% Traditional ROI: 5.4%
11380 NW 92ND CT Chiefland, FL Imagine ending your day on the covered back porch, surrounded by quiet country skies, whil...	3 beds \| 2 baths \| 1,580 sq.ft.	$339,900	Airbnb cash on cash: 3.52% Traditional cash on cash: 6.65% Airbnb Rental Income: $2093 Traditional Rental Income: $2556 Airbnb ROI: 3.52% Traditional ROI: 6.65%
11231 NW 92ND CT Chiefland, FL Eligible for 100% financing!! Brand New Home in Golf Course Community with no HOA fees!! D...	3 beds \| 2 baths \| 1,584 sq.ft.	$339,900	Airbnb cash on cash: 3.52% Traditional cash on cash: 6.65% Airbnb Rental Income: $2093 Traditional Rental Income: $2556 Airbnb ROI: 3.52% Traditional ROI: 6.65%
7021 NW 112 Place Chiefland, FL Welcome to peaceful country living in Buck Bay Subdivision in Chiefland! This brand new 3 ...	3 beds \| 2 baths \| 1,606 sq.ft.	$299,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 5.3% Airbnb Rental Income: $2093 Traditional Rental Income: $1914 Airbnb ROI: 4.02% Traditional ROI: 5.3%
7750 NW 136th St Chiefland, FL Back Active! Previous buyers' circumstances changed, but the good news for you is this hom...	3 beds \| 2 baths \| 1,940 sq.ft.	$462,900	Airbnb cash on cash: 1.6% Traditional cash on cash: 3.85% Airbnb Rental Income: $2093 Traditional Rental Income: $2532 Airbnb ROI: 1.6% Traditional ROI: 3.85%
15770 NW 60TH Avenue Chiefland, FL Welcome to your dream farm! Nestled on 13+ beautiful acres, this exceptional property offe...	3 beds \| 2 baths \| 2,200 sq.ft.	$580,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 2.47% Airbnb Rental Income: $2093 Traditional Rental Income: $2127 Airbnb ROI: 1.42% Traditional ROI: 2.47%
6890 NW 68th Pl Chiefland, FL Horse lovers, this is the one you've been waiting for! Nestled on 5 beautiful acres just o...	3 beds \| 2 baths \| 3,528 sq.ft.	$385,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 4.33% Airbnb Rental Income: $2093 Traditional Rental Income: $2141 Airbnb ROI: 2.71% Traditional ROI: 4.33%
227 NE 4th St Chiefland, FL This cozy 2-bedroom, 1-bathroom cracker home is nestled on a spacious lot spanning four ci...	2 beds \| 1 baths \| 1,047 sq.ft.	$134,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 6.69% Airbnb Rental Income: $644 Traditional Rental Income: $1259 Airbnb ROI: -0.34% Traditional ROI: 6.69%
8731 NW 127TH Place Chiefland, FL THIS property has it ALL! A solid concrete block home , 3 bedrooms / 2 bathrooms with a De...	3 beds \| 2 baths \| 1,344 sq.ft.	$259,900	Airbnb cash on cash: 4.5% Traditional cash on cash: 4.73% Airbnb Rental Income: $2093 Traditional Rental Income: $1610 Airbnb ROI: 4.5% Traditional ROI: 4.73%
5231 NW 73RD Street Chiefland, FL Welcome to the gorgeous Spanish Trace Subdivision located in the countryside of Chiefland ...	3 beds \| 2 baths \| 1,715 sq.ft.	$329,900	Airbnb cash on cash: 2.68% Traditional cash on cash: 4.29% Airbnb Rental Income: $2093 Traditional Rental Income: $2052 Airbnb ROI: 2.68% Traditional ROI: 4.29%
6150 NW County Road 345 Chiefland, FL Single-Family Home with Guest House or Multi-Family / Income-Producing Opportunity in Chie...	2 beds \| 1 baths \| 2,010 sq.ft.	$295,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 2.6% Airbnb Rental Income: $644 Traditional Rental Income: $1314 Airbnb ROI: -0.88% Traditional ROI: 2.6%
9291 NW 127 Place Chiefland, FL Fall in love with the warmth, craftsmanship, and unmistakable character of this one-of-a-k...	3 beds \| 3 baths \| 2,408 sq.ft.	$449,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 5.32% Airbnb Rental Income: $2093 Traditional Rental Income: $3070 Airbnb ROI: 1.72% Traditional ROI: 5.32%
11251 NW 109th Ct Chiefland, FL Discover your dream home nestled on an expansive 1.86-acre lot that offers both space and ...	3 beds \| 2 baths \| 2,152 sq.ft.	$278,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 6.14% Airbnb Rental Income: $2093 Traditional Rental Income: $2174 Airbnb ROI: 3.78% Traditional ROI: 6.14%
11491 NW 92ND CT Chiefland, FL Under Construction. Eligible for 100% financing!! Brand New Home in Golf Course Community ...	3 beds \| 2 baths \| 1,173 sq.ft.	$249,900	Airbnb cash on cash: 5.11% Traditional cash on cash: 6.01% Airbnb Rental Income: $2093 Traditional Rental Income: $1769 Airbnb ROI: 5.11% Traditional ROI: 6.01%
1945 NW 23rd Ave Chiefland, FL Pull into the drive at 1945 NW 23rd Avenue and you immediately notice the privacy this pro...	2 beds \| 2 baths \| 1,371 sq.ft.	$355,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.42% Airbnb Rental Income: $644 Traditional Rental Income: $1956 Airbnb ROI: -0.4% Traditional ROI: 4.42%
8851 NW 115th St Chiefland, FL This luxury saltwater pool home offers 3 bedrooms, 2 full baths, 2 half baths, and an addi...	3 beds \| 4 baths \| 4,970 sq.ft.	$739,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 1.74% Airbnb Rental Income: $2093 Traditional Rental Income: $2329 Airbnb ROI: 0.61% Traditional ROI: 1.74%
5300 NW 52nd Ct Chiefland, FL From the first look down the private drive, it becomes clear this is not a typical North F...	4 beds \| 4 baths \| 2,315 sq.ft.	$639,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 3.01% Airbnb Rental Income: $6815 Traditional Rental Income: $2894 Airbnb ROI: 7.37% Traditional ROI: 3.01%
2770 107th Pl Chiefland, FL REDUCED! Now under 300K! For sale is a beautifully remodeled 1993 mobile home that sits on...	3 beds \| 2 baths \| 1,448 sq.ft.	$299,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 3.84% Airbnb Rental Income: $2093 Traditional Rental Income: $1653 Airbnb ROI: 3.49% Traditional ROI: 3.84%
14590 NE 35th Ave Chiefland, FL Escape to your own private North Florida retreat with this beautiful 3 bedroom, 2 bathroom...	3 beds \| 2 baths \| 2,310 sq.ft.	$650,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.37% Airbnb Rental Income: $2093 Traditional Rental Income: $1716 Airbnb ROI: 1.1% Traditional ROI: 1.37%
713 NE 3rd St Chiefland, FL BRAND NEW 2026 DWMH centrally located in Chiefland, FL! This newly setup LIVE OAK home is ...	3 beds \| 2 baths \| 1,352 sq.ft.	$199,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 7.04% Airbnb Rental Income: $2093 Traditional Rental Income: $1646 Airbnb ROI: 6.56% Traditional ROI: 7.04%
12450 NW 85TH Avenue Chiefland, FL Virtually Staged. This is the kind of 5-acre setup that does not come around often. Sittin...	3 beds \| 2 baths \| 1,056 sq.ft.	$350,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 2.42% Airbnb Rental Income: $2093 Traditional Rental Income: $1546 Airbnb ROI: 2.45% Traditional ROI: 2.42%
11097 NW 114th St Chiefland, FL MUST SEE!! Welcome to this beautifully remodeled and EXCEPTIONALLY well-maintained manufac...	2 beds \| 2 baths \| 2,520 sq.ft.	$159,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 11.09% Airbnb Rental Income: $644 Traditional Rental Income: $2059 Airbnb ROI: -0.12% Traditional ROI: 11.09%
1204 SW 2nd Dr Chiefland, FL This stunning starter home is perfect for those looking to downsize or first-time buyers! ...	2 beds \| 1 baths \| 750 sq.ft.	$120,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 8.37% Airbnb Rental Income: $644 Traditional Rental Income: $1238 Airbnb ROI: 0.68% Traditional ROI: 8.37%
214 NE 4TH Street Chiefland, FL Welcome to this charming 3-bedroom, 2-bath home located within the city limits of Chieflan...	3 beds \| 2 baths \| 982 sq.ft.	$189,000	Airbnb cash on cash: 6.02% Traditional cash on cash: 6.65% Airbnb Rental Income: $2093 Traditional Rental Income: $1669 Airbnb ROI: 6.02% Traditional ROI: 6.65%
4190 NW 153RD Court Chiefland, FL Nothing beats living on The Great Suwannee River, in the heart of the Fowlers Bluff Commun...	4 beds \| 2 baths \| 2,282 sq.ft.	$830,000	Airbnb cash on cash: 5.91% Traditional cash on cash: 1.59% Airbnb Rental Income: $6815 Traditional Rental Income: $2144 Airbnb ROI: 5.91% Traditional ROI: 1.59%
4261 NW 57th Ct Chiefland, FL Welcome to your own private North Florida retreat! Nestled on 20 beautiful acres in Chiefl...	3 beds \| 2 baths \| 3,376 sq.ft.	$779,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 1.74% Airbnb Rental Income: $2093 Traditional Rental Income: $2611 Airbnb ROI: 0.28% Traditional ROI: 1.74%
5391 NW 137th Ln Chiefland, FL Welcome to your private oasis in Countryside Estates-a beautifully maintained 1,738 sq ft ...	3 beds \| 2 baths \| 2,842 sq.ft.	$487,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 2.66% Airbnb Rental Income: $2093 Traditional Rental Income: $1868 Airbnb ROI: 1.98% Traditional ROI: 2.66%
115 NE 5TH Street Chiefland, FL Virtually Staged. Welcome home to this meticulously maintained 3 bedroom / 2 bathroom with...	3 beds \| 2 baths \| 2,058 sq.ft.	$199,999	Airbnb cash on cash: 4.89% Traditional cash on cash: 9.45% Airbnb Rental Income: $2093 Traditional Rental Income: $2421 Airbnb ROI: 4.89% Traditional ROI: 9.45%

Real Estate investment in Chiefland, FL

There are 38 properties for sale in the city of Chiefland . The median list price in Chiefland is $204,328 and the average price per square foot is $102. In September 2026, the average monthly cash on cash return in Chiefland is 4.00%. The average monthly rental income in Chiefland is $1,886.

Chiefland, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 38 investment properties available for sale in Chiefland.

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

The ROI for Long-Term is higher than the Short-Term in Chiefland with average rental income of $1,886.

Your search for investment property begins and ends here

Investment Property for Sale in Chiefland, FL

2691 NW 74th Ter

Chiefland, FL

3 beds | 2 baths | 1,812 sq.ft.

$154,900

Airbnb cash on cash: 8.12%

Traditional cash on cash: 9.15%

Airbnb Rental Income: $2093

Traditional Rental Income: $1708

Airbnb ROI: 8.12%

Traditional ROI: 9.15%

1108 SW 2ND Avenue

Chiefland, FL

3 beds | 2 baths | 1,572 sq.ft.

$300,000

Airbnb cash on cash: 3.05%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $2093

Traditional Rental Income: $2008

Airbnb ROI: 3.05%

Traditional ROI: 4.66%

308 SW 2ND Avenue

Chiefland, FL

3 beds | 2 baths | 1,163 sq.ft.

$217,000

Airbnb cash on cash: 4.77%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $2093

Traditional Rental Income: $945

Airbnb ROI: 4.77%

Traditional ROI: 1.8%

3551 NW 60th Ave

Chiefland, FL

3 beds | 2 baths | 2,195 sq.ft.

$499,900

Airbnb cash on cash: 1.67%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $2093

Traditional Rental Income: $1162

Airbnb ROI: 1.67%

Traditional ROI: 0.83%

1191 NW 120th St

Chiefland, FL

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

$499,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $644

Traditional Rental Income: $2387

Airbnb ROI: -1.06%

Traditional ROI: 3.31%

4651 NE 108TH Place

Chiefland, FL

3 beds | 2 baths | 912 sq.ft.

$675,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $2093

Traditional Rental Income: $1903

Airbnb ROI: 0.91%

Traditional ROI: 1.46%

5590 NW 76th Avenue

Chiefland, FL

2 beds | 2 baths | 924 sq.ft.

$199,000

Airbnb cash on cash: -0.61%

Traditional cash on cash: 6.67%

Airbnb Rental Income: $644

Traditional Rental Income: $1723

Airbnb ROI: -0.61%

Traditional ROI: 6.67%

9492 NW 46th Pl

Chiefland, FL

3 beds | 3 baths | 3,818 sq.ft.

$650,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $2093

Traditional Rental Income: $3443

Airbnb ROI: 1.34%