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 Beautiful, like-new 2022 farmhouse-style home located in the sought after Crooked Creek ar...	4 beds \| 3 baths \| 2,134 sq.ft.	$519,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.56% Airbnb Rental Income: $4157 Traditional Rental Income: $2748 Airbnb ROI: 4.65% Traditional ROI: 3.56%
140 SHUMARD Court Monticello, FL Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet...	4 beds \| 3 baths \| 2,716 sq.ft.	$625,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 1.61% Airbnb Rental Income: $4157 Traditional Rental Income: $2363 Airbnb ROI: 3.17% Traditional ROI: 1.61%
339 Silver Lake Rd. Monticello, FL Large home on 5 acres mostly pasture~very peaceful setting~BRAND NEW LVP~Open concept with...	3 beds \| 3 baths \| 2,706 sq.ft.	$375,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 9.63% Airbnb Rental Income: $788 Traditional Rental Income: $4145 Airbnb ROI: -0.82% Traditional ROI: 9.63%
761 Hawkins Road Monticello, FL This one truly has it all! Nestled on 5+ private acres in beautiful Monticello, Florida, t...	4 beds \| 3 baths \| 2,873 sq.ft.	$550,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 3.7% Airbnb Rental Income: $4157 Traditional Rental Income: $2868 Airbnb ROI: 4.49% Traditional ROI: 3.7%
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.	$769,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 2.08% Airbnb Rental Income: $788 Traditional Rental Income: $2729 Airbnb ROI: -1.08% Traditional ROI: 2.08%
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: -0.8% Traditional cash on cash: 5.9% Airbnb Rental Income: $788 Traditional Rental Income: $3778 Airbnb ROI: -0.8% Traditional ROI: 5.9%
4589 Ashville Highway Monticello, FL Nestled on 5.56 acres of fenced pastureland, this stunning estate, is framed by majestic o...	3 beds \| 3 baths \| 3,832 sq.ft.	$695,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.73% Airbnb Rental Income: $788 Traditional Rental Income: $2703 Airbnb ROI: -0.72% Traditional ROI: 2.73%
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: -0.64% Traditional cash on cash: 4.94% Airbnb Rental Income: $788 Traditional Rental Income: $2145 Airbnb ROI: -0.64% Traditional ROI: 4.94%
205 N Rhodes Street Monticello, FL Classic historical home built in the 1920's. Walking distance to charming downtown Montice...	3 beds \| 2 baths \| 2,766 sq.ft.	$345,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 5.32% Airbnb Rental Income: $788 Traditional Rental Income: $2426 Airbnb ROI: -0.73% Traditional ROI: 5.32%
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.	$449,900	Airbnb cash on cash: 5.67% Traditional cash on cash: 4.19% Airbnb Rental Income: $4157 Traditional Rental Income: $2652 Airbnb ROI: 5.67% Traditional ROI: 4.19%
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%
2664 A W Washington Highway Monticello, FL FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move...	5 beds \| 2 baths \| 2,659 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.5% Airbnb Rental Income: $null Traditional Rental Income: $2653 Airbnb ROI: N/A Traditional ROI: 6.5%
285 Mallard Lane Monticello, FL One or more pictures is virtually enhanced *Jefferson County peaceful country living with ...	3 beds \| 2 baths \| 2,000 sq.ft.	$434,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 4.72% Airbnb Rental Income: $788 Traditional Rental Income: $2749 Airbnb ROI: -0.89% Traditional ROI: 4.72%
728 Turney Anderson Road Monticello, FL A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home cap...	3 beds \| 3 baths \| 3,677 sq.ft.	$799,999	Airbnb cash on cash: -1.05% Traditional cash on cash: 1.91% Airbnb Rental Income: $788 Traditional Rental Income: $2678 Airbnb ROI: -1.05% Traditional ROI: 1.91%
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.	$439,900	Airbnb cash on cash: -0.23% Traditional cash on cash: 4.59% Airbnb Rental Income: $788 Traditional Rental Income: $2455 Airbnb ROI: -0.23% Traditional ROI: 4.59%
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: -1.23% Traditional cash on cash: 1.48% Airbnb Rental Income: $702 Traditional Rental Income: $1648 Airbnb ROI: -1.23% Traditional ROI: 1.48%
925 HIAWATHA FARMS Road Monticello, FL (One or more photos has been virtually staged) Custom hurricane-resistant/efficiency home ...	4 beds \| 3 baths \| 2,112 sq.ft.	$550,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 4.03% Airbnb Rental Income: $4157 Traditional Rental Income: $2972 Airbnb ROI: 4.62% Traditional ROI: 4.03%
490 N Cherry Court Monticello, FL Step into city living just steps from Downtown Monticello, Fl. This one-story condo with p...	2 beds \| 2 baths \| 1,411 sq.ft.	$267,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 5.51% Airbnb Rental Income: $702 Traditional Rental Income: $1996 Airbnb ROI: -0.82% Traditional ROI: 5.51%
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: -0.22% Traditional cash on cash: 4.82% Airbnb Rental Income: $788 Traditional Rental Income: $1606 Airbnb ROI: -0.22% 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: -0.74% Traditional cash on cash: 4.11% Airbnb Rental Income: $788 Traditional Rental Income: $2056 Airbnb ROI: -0.74% Traditional ROI: 4.11%
9901 GAMBLE Road Monticello, FL PRIVATE 20-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME ...	3 beds \| 3 baths \| 2,436 sq.ft.	$765,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 1.93% Airbnb Rental Income: $788 Traditional Rental Income: $2812 Airbnb ROI: -1.36% Traditional ROI: 1.93%
1012 S Main Avenue Monticello, FL Tucked away on 5 private acres down a quiet, wooded road, this brick home offers 2,280 squ...	3 beds \| 2 baths \| 2,280 sq.ft.	$399,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 4.37% Airbnb Rental Income: $788 Traditional Rental Income: $2324 Airbnb ROI: -0.59% Traditional ROI: 4.37%
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	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $4746 Airbnb ROI: N/A Traditional ROI: 6.86%
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	$390,000	Airbnb cash on cash: 6.67% Traditional cash on cash: 0.12% Airbnb Rental Income: $4157 Traditional Rental Income: $881 Airbnb ROI: 6.67% Traditional ROI: 0.12%
60 Bob White Trail Monticello, FL Tucked behind a gated entrance and surrounded by 5.54 acres of open space, this property o...	3 beds \| 2 baths \| 1,620 sq.ft.	$285,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 5.5% Airbnb Rental Income: $788 Traditional Rental Income: $1845 Airbnb ROI: 0.38% Traditional ROI: 5.5%
1628 N Jefferson Highway Monticello, FL Picturesque, 3/2, brick beauty with a whimsical style that evokes the charm of a tradition...	3 beds \| 3 baths \| 3,127 sq.ft.	$398,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 7.53% Airbnb Rental Income: $788 Traditional Rental Income: $3423 Airbnb ROI: -0.37% 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.	$269,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 5.28% Airbnb Rental Income: $788 Traditional Rental Income: $1775 Airbnb ROI: 0.15% Traditional ROI: 5.28%
254 Woodland Drive Monticello, FL Custom home on 4.29 private acres~split bedroom plan~separate dining room~rocking chair fr...	3 beds \| 2 baths \| 2,239 sq.ft.	$450,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 3.82% Airbnb Rental Income: $788 Traditional Rental Income: $2317 Airbnb ROI: -0.56% Traditional ROI: 3.82%
120 Larry's Lane Monticello, FL Recently renovated home on large lot out in the country. Quiet living at it's best only a ...	3 beds \| 2 baths \| 1,323 sq.ft.	$227,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.34% Airbnb Rental Income: $788 Traditional Rental Income: $1651 Airbnb ROI: -0.14% Traditional ROI: 5.34%
670 Poplar Street Monticello, FL Solid 3/1 SFR brick less than a mile from downtown Monticello! This quaint 1,312 sq ft hom...	3 beds \| 1 baths \| 1,312 sq.ft.	$185,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 5.97% Airbnb Rental Income: $788 Traditional Rental Income: $1488 Airbnb ROI: 0.17% Traditional ROI: 5.97%

Real Estate investment in Monticello, FL

There are 60 properties for sale in the city of Monticello . The median list price in Monticello is $255,297 and the average price per square foot is $165. In July 2026, the average monthly cash on cash return in Monticello is 5.00%. The average monthly rental income in Monticello is $2,226.

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

There are 60 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 $788.

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.

$519,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $4157

Traditional Rental Income: $2748

Airbnb ROI: 4.65%

Traditional ROI: 3.56%

140 SHUMARD Court

Monticello, FL

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

$625,000

Airbnb cash on cash: 3.17%

Traditional cash on cash: 1.61%

Airbnb Rental Income: $4157

Traditional Rental Income: $2363

Airbnb ROI: 3.17%

Traditional ROI: 1.61%

339 Silver Lake Rd.

Monticello, FL

3 beds | 3 baths | 2,706 sq.ft.

$375,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 9.63%

Airbnb Rental Income: $788

Traditional Rental Income: $4145

Airbnb ROI: -0.82%

Traditional ROI: 9.63%

761 Hawkins Road

Monticello, FL

4 beds | 3 baths | 2,873 sq.ft.

$550,000

Airbnb cash on cash: 4.49%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $4157

Traditional Rental Income: $2868

Airbnb ROI: 4.49%

Traditional ROI: 3.7%

660 Whispering Hills Road

Monticello, FL

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

$769,000

Airbnb cash on cash: -1.08%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $788

Traditional Rental Income: $2729

Airbnb ROI: -1.08%

Traditional ROI: 2.08%

515 E Palmer Mill Road

Monticello, FL

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

$529,000

Airbnb cash on cash: -0.8%

Traditional cash on cash: 5.9%

Airbnb Rental Income: $788

Traditional Rental Income: $3778

Airbnb ROI: -0.8%

Traditional ROI: 5.9%

4589 Ashville Highway

Monticello, FL

3 beds | 3 baths | 3,832 sq.ft.

$695,000

Airbnb cash on cash: -0.72%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $788

Traditional Rental Income: $2703

Airbnb ROI: -0.72%

Traditional ROI: 2.73%

300 Bowman Street

Monticello, FL

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

$319,900

Airbnb cash on cash: -0.64%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $788

Traditional Rental Income: $2145

Airbnb ROI: -0.64%