Real Estate Investment Properties for Sale in Monticello, FL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
121 Shumard Court Monticello, FL Exceptionally maintained , this turn key 2022 farmhouse-style home is located in the sough...	4 beds \| 3 baths \| 2,134 sq.ft.	$510,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 3.65% Airbnb Rental Income: $4157 Traditional Rental Income: $2748 Airbnb ROI: 4.76% Traditional ROI: 3.65%
140 SHUMARD Court Monticello, FL NOW INCLUDES ADDITIONAL LOT!! Discover this stunning 2,600+ sqft home built in 2021, offer...	4 beds \| 3 baths \| 2,716 sq.ft.	$677,500	Airbnb cash on cash: 2.85% Traditional cash on cash: 1.41% Airbnb Rental Income: $4157 Traditional Rental Income: $2363 Airbnb ROI: 2.85% Traditional ROI: 1.41%
660 Whispering Hills Road Monticello, FL Set on 18+ acres of beautifully maintained pasture, this private country property is built...	3 beds \| 3 baths \| 2,160 sq.ft.	$700,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 2.38% Airbnb Rental Income: $3308 Traditional Rental Income: $2729 Airbnb ROI: 2.13% Traditional ROI: 2.38%
515 E Palmer Mill Road Monticello, FL MOTIVATED SELLERS - CONCESSION(S) BEING OFFERED Remarkable, peaceful in-town oasis on ...	3 beds \| 3 baths \| 2,187 sq.ft.	$529,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 5.9% Airbnb Rental Income: $3308 Traditional Rental Income: $3778 Airbnb ROI: 3.45% Traditional ROI: 5.9%
300 Bowman Street Monticello, FL Recently built home featuring spacious open floor plan. Kitchen has raised cabinets, grani...	3 beds \| 3 baths \| 1,550 sq.ft.	$319,900	Airbnb cash on cash: 6.34% Traditional cash on cash: 4.94% Airbnb Rental Income: $3308 Traditional Rental Income: $2145 Airbnb ROI: 6.34% Traditional ROI: 4.94%
855 S Waukeenah Street Monticello, FL Stunning New Construction recently built by Southern Construction. Centrally located in do...	4 beds \| 3 baths \| 1,798 sq.ft.	$424,900	Airbnb cash on cash: 6.11% Traditional cash on cash: 4.55% Airbnb Rental Income: $4157 Traditional Rental Income: $2652 Airbnb ROI: 6.11% Traditional ROI: 4.55%
930 E Pearl Street Monticello, FL Built between 1890-1910, this Classic Revival home sits on 1.77 acres along one of Montice...	4 beds \| 3 baths \| 3,188 sq.ft.	$395,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 8.66% Airbnb Rental Income: $4157 Traditional Rental Income: $3865 Airbnb ROI: 7.07% Traditional ROI: 8.66%
4216 W Washington Highway Monticello, FL Tucked away on 10.87 private acres behind its own gated entrance in the sought-after Raine...	3 beds \| 3 baths \| 2,412 sq.ft.	$915,000	Airbnb cash on cash: 1% Traditional cash on cash: 1.28% Airbnb Rental Income: $3308 Traditional Rental Income: $2812 Airbnb ROI: 1% Traditional ROI: 1.28%
107 S TARN Way Monticello, FL Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and loca...	3 beds \| 2 baths \| 1,774 sq.ft.	$429,900	Airbnb cash on cash: 5% Traditional cash on cash: 4.72% Airbnb Rental Income: $3308 Traditional Rental Income: $2455 Airbnb ROI: 5% Traditional ROI: 4.72%
640 Nautilus Drive Monticello, FL Secluded 56.37 Acres with Metal Building & Living Quarters -Western Jefferson County. This...	2 beds \| 1 baths \| 1,200 sq.ft.	$495,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.48% Airbnb Rental Income: $1445 Traditional Rental Income: $1648 Airbnb ROI: 0.11% Traditional ROI: 1.48%
490 N Cherry Court Monticello, FL This is the kind of home you can move into and simply enjoy. Located in Cherry Street Squa...	2 beds \| 2 baths \| 1,411 sq.ft.	$254,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 5.86% Airbnb Rental Income: $1445 Traditional Rental Income: $1996 Airbnb ROI: 1.77% Traditional ROI: 5.86%
220 Eaton Street Monticello, FL Very convenient location in the heart of Monticello. Excellent condition. Very good condit...	3 beds \| 1 baths \| 1,164 sq.ft.	$239,000	Airbnb cash on cash: 9.07% Traditional cash on cash: 4.82% Airbnb Rental Income: $3308 Traditional Rental Income: $1606 Airbnb ROI: 9.07% Traditional ROI: 4.82%
398 Tecumseh Road Monticello, FL Charming Cape Cod-style home tucked away on 5 acres just minutes to downtown Monticello. T...	5 beds \| 2 baths \| 2,268 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $2584 Airbnb ROI: N/A Traditional ROI: 3.45%
8156 Waukeenah Highway Monticello, FL Rare Find! Country Living on 1 Acre-No HOA! Enjoy peaceful country living on a full 1-acre...	3 beds \| 2 baths \| 1,774 sq.ft.	$349,000	Airbnb cash on cash: 5.67% Traditional cash on cash: 4.11% Airbnb Rental Income: $3308 Traditional Rental Income: $2056 Airbnb ROI: 5.67% Traditional ROI: 4.11%
9901 Gamble Road Monticello, FL PRIVATE 41-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME ...	3 beds \| 3 baths \| 2,436 sq.ft.	$899,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 1.36% Airbnb Rental Income: $3308 Traditional Rental Income: $2812 Airbnb ROI: 1.07% Traditional ROI: 1.36%
535 Hagan Street Monticello, FL Rare Investor Opportunity: 7-Unit Residential Complex for Sale Don't miss this fantastic i...	11 beds \| 4 baths \| N/A	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.39% Airbnb Rental Income: $null Traditional Rental Income: $4746 Airbnb ROI: N/A Traditional ROI: 7.39%
480 S JEFFERSON Street Monticello, FL Located in the heart of Monticello, this 5-unit investment property offers a prime opportu...	4 beds \| 4 baths \| N/A	$364,900	Airbnb cash on cash: 7.19% Traditional cash on cash: 0.2% Airbnb Rental Income: $4157 Traditional Rental Income: $881 Airbnb ROI: 7.19% Traditional ROI: 0.2%
1628 N Jefferson Highway Monticello, FL For generations, this beautifully maintained, one-family owned brick home has been a place...	3 beds \| 3 baths \| 3,127 sq.ft.	$398,900	Airbnb cash on cash: 5.24% Traditional cash on cash: 7.53% Airbnb Rental Income: $3308 Traditional Rental Income: $3423 Airbnb ROI: 5.24% Traditional ROI: 7.53%
1164 Oaklands Plantation Road Monticello, FL Nestled on 5.5 peaceful, private acres, this charming 3-bedroom, 2-bath home offers the pe...	3 beds \| 2 baths \| 1,456 sq.ft.	$259,900	Airbnb cash on cash: 8.75% Traditional cash on cash: 5.52% Airbnb Rental Income: $3308 Traditional Rental Income: $1775 Airbnb ROI: 8.75% Traditional ROI: 5.52%
1590 Tyson Road Monticello, FL Experience the beauty and tranquility of North Florida living on this stunning estate loca...	3 beds \| 2 baths \| 2,612 sq.ft.	$1,175,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 0.56% Airbnb Rental Income: $3308 Traditional Rental Income: $2205 Airbnb ROI: 0.89% Traditional ROI: 0.56%
1070 Partridge Lane Monticello, FL Currently under construction. Interior pictures are from a previous model home. Approximat...	3 beds \| 2 baths \| 1,351 sq.ft.	$298,900	Airbnb cash on cash: 6.91% Traditional cash on cash: 4.18% Airbnb Rental Income: $3308 Traditional Rental Income: $1800 Airbnb ROI: 6.91% Traditional ROI: 4.18%
360 Bowman Street Monticello, FL New construction; very convenient to downtown; house is close to completion - should be re...	3 beds \| 2 baths \| 1,235 sq.ft.	$254,900	Airbnb cash on cash: 9.26% Traditional cash on cash: 5.83% Airbnb Rental Income: $3308 Traditional Rental Income: $1743 Airbnb ROI: 9.26% Traditional ROI: 5.83%
8250 WAUKEENAH Highway Monticello, FL Enjoy two private year around spring fed ponds! Escape to your own private sanctuary on 30...	3 beds \| 4 baths \| 2,148 sq.ft.	$584,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 5.32% Airbnb Rental Income: $3308 Traditional Rental Income: $4071 Airbnb ROI: 2.57% Traditional ROI: 5.32%
947 Piney Woods Road Monticello, FL Charming 2022 Mobile Home on 5 Peaceful Acres A rare blend of modern comfort and wide-open...	4 beds \| 2 baths \| 2,304 sq.ft.	$325,000	Airbnb cash on cash: 8.57% Traditional cash on cash: 5.21% Airbnb Rental Income: $4157 Traditional Rental Income: $2248 Airbnb ROI: 8.57% Traditional ROI: 5.21%

Real Estate investment in Monticello, FL

There are 48 properties for sale in the city of Monticello . The median list price in Monticello is $268,322 and the average price per square foot is $173. In October 2026, the average monthly cash on cash return in Monticello is 5.00%. The average monthly rental income in Monticello is $2,261.

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

There are 48 investment properties available for sale in Monticello.

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

The ROI for Short-Term is higher than the Long-Term in Monticello with average rental income of $3,308.

Your search for investment property begins and ends here

Investment Property for Sale in Monticello, FL

121 Shumard Court

Monticello, FL

4 beds | 3 baths | 2,134 sq.ft.

$510,000

Airbnb cash on cash: 4.76%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $4157

Traditional Rental Income: $2748

Airbnb ROI: 4.76%

Traditional ROI: 3.65%

140 SHUMARD Court

Monticello, FL

4 beds | 3 baths | 2,716 sq.ft.

$677,500

Airbnb cash on cash: 2.85%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $4157

Traditional Rental Income: $2363

Airbnb ROI: 2.85%

Traditional ROI: 1.41%

660 Whispering Hills Road

Monticello, FL

3 beds | 3 baths | 2,160 sq.ft.

$700,000

Airbnb cash on cash: 2.13%

Traditional cash on cash: 2.38%

Airbnb Rental Income: $3308

Traditional Rental Income: $2729

Airbnb ROI: 2.13%

Traditional ROI: 2.38%

515 E Palmer Mill Road

Monticello, FL

3 beds | 3 baths | 2,187 sq.ft.

$529,000

Airbnb cash on cash: 3.45%

Traditional cash on cash: 5.9%

Airbnb Rental Income: $3308

Traditional Rental Income: $3778

Airbnb ROI: 3.45%

Traditional ROI: 5.9%

300 Bowman Street

Monticello, FL

3 beds | 3 baths | 1,550 sq.ft.

$319,900

Airbnb cash on cash: 6.34%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $3308

Traditional Rental Income: $2145

Airbnb ROI: 6.34%

Traditional ROI: 4.94%

855 S Waukeenah Street

Monticello, FL

4 beds | 3 baths | 1,798 sq.ft.

$424,900

Airbnb cash on cash: 6.11%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $4157

Traditional Rental Income: $2652

Airbnb ROI: 6.11%

Traditional ROI: 4.55%

930 E Pearl Street

Monticello, FL

4 beds | 3 baths | 3,188 sq.ft.

$395,000

Airbnb cash on cash: 7.07%

Traditional cash on cash: 8.66%

Airbnb Rental Income: $4157

Traditional Rental Income: $3865

Airbnb ROI: 7.07%

Traditional ROI: 8.66%

4216 W Washington Highway

Monticello, FL

3 beds | 3 baths | 2,412 sq.ft.

$915,000

Airbnb cash on cash: 1%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $3308

Traditional Rental Income: $2812

Airbnb ROI: 1%