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
79 Lakeside Rd Monticello, FL Go Back in time in this traditional farmhouse nestled on 4.44 acres totally fence and cros...	3 beds \| 2 baths \| 3,054 sq.ft.	$519,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 4.26% Airbnb Rental Income: $788 Traditional Rental Income: $3508 Airbnb ROI: -1.21% Traditional ROI: 4.26%
155 E Seminole Ave Monticello, FL Full of character, this spacious 1950s home offers 4 bedrooms and 3 full bathrooms on a ge...	4 beds \| 3 baths \| 2,223 sq.ft.	$325,000	Airbnb cash on cash: 8.3% Traditional cash on cash: 6.54% Airbnb Rental Income: $4157 Traditional Rental Income: $2738 Airbnb ROI: 8.3% Traditional ROI: 6.54%
354 Pine Cone Dr Monticello, FL 2024 construction, shows like brand new home on large .68 acre lot, wooded buffer adds pri...	3 beds \| 2 baths \| 1,604 sq.ft.	$317,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 2.55% Airbnb Rental Income: $788 Traditional Rental Income: $1449 Airbnb ROI: -0.66% Traditional ROI: 2.55%
1160 E Washington St Monticello, FL Remodeled brick home, 3 br 1 bath, open kitchen living room with fireplace. Large utility ...	3 beds \| 1 baths \| 1,334 sq.ft.	$252,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.01% Airbnb Rental Income: $788 Traditional Rental Income: $1257 Airbnb ROI: -0.31% Traditional ROI: 3.01%
339 Silver Lake Rd. Monticello, FL Gorgeous home on 5 acres mostly pasture. Open concept with vaulted ceilings; great enterta...	3 beds \| 3 baths \| 2,706 sq.ft.	$375,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 5.86% Airbnb Rental Income: $788 Traditional Rental Income: $2817 Airbnb ROI: -0.82% Traditional ROI: 5.86%
515 E Palmer Mill Rd Monticello, FL Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downt...	3 beds \| 3 baths \| 2,187 sq.ft.	$579,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 4.24% Airbnb Rental Income: $788 Traditional Rental Income: $3203 Airbnb ROI: -0.81% Traditional ROI: 4.24%
107 Tarn Way Monticello, FL 2024 Custom Built Home with Premium Upgrades in Hemings Pond Subdivision! Better than new ...	3 beds \| 2 baths \| 1,774 sq.ft.	$449,900	Airbnb cash on cash: -1.03% Traditional cash on cash: 3.11% Airbnb Rental Income: $788 Traditional Rental Income: $2210 Airbnb ROI: -1.03% Traditional ROI: 3.11%
3827 N Jefferson St Monticello, FL Spacious Contemporary Home on 5 Acres with Pond, Minutes from Thomasville, Ga! Enjoy peace...	3 beds \| 3 baths \| 3,026 sq.ft.	$499,500	Airbnb cash on cash: -0.28% Traditional cash on cash: 4.2% Airbnb Rental Income: $788 Traditional Rental Income: $2666 Airbnb ROI: -0.28% Traditional ROI: 4.2%
181 Heritage Blvd Monticello, FL Certified Florida Green Home on 3 acres in the highly sough after Heritage Hills s/d. Enjo...	3 beds \| 2 baths \| 2,546 sq.ft.	$599,900	Airbnb cash on cash: -0.8% Traditional cash on cash: 3.28% Airbnb Rental Income: $788 Traditional Rental Income: $2756 Airbnb ROI: -0.8% Traditional ROI: 3.28%
205 N Rhodes St Monticello, FL Classic historical home built in the 1920's. Walking distance to charming downtown Montice...	3 beds \| 2 baths \| 2,766 sq.ft.	$365,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 5.23% Airbnb Rental Income: $788 Traditional Rental Income: $2529 Airbnb ROI: -0.79% Traditional ROI: 5.23%
47 Mire Ct Monticello, FL Amazing new construction Available Now 3 bedroom 2 bathroom by Nailed It Tallahassee LLC L...	3 beds \| 2 baths \| 1,806 sq.ft.	$455,995	Airbnb cash on cash: -1.04% Traditional cash on cash: 2.77% Airbnb Rental Income: $788 Traditional Rental Income: $2094 Airbnb ROI: -1.04% Traditional ROI: 2.77%
2436 N Jefferson Monticello, FL THIS PROPERTY WILL NEED A TOTAL RENOVATION ON BOTH HOMES. Discover the perfect blend of ru...	3 beds \| 2 baths \| 2,390 sq.ft.	$198,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 10.57% Airbnb Rental Income: $788 Traditional Rental Income: $2479 Airbnb ROI: -0.13% Traditional ROI: 10.57%
1125 E Dogwood St Monticello, FL Must see this brand new home built by Southern Construction in the downtown Monticello are...	3 beds \| 2 baths \| 1,290 sq.ft.	$265,900	Airbnb cash on cash: -0.39% Traditional cash on cash: 5.98% Airbnb Rental Income: $788 Traditional Rental Income: $2066 Airbnb ROI: -0.39% Traditional ROI: 5.98%
513 Creekside Ct Monticello, FL Custom home built by Kessler Construction on 2 full acres in desirable Crook Creek subdivi...	4 beds \| 3 baths \| 2,660 sq.ft.	$589,900	Airbnb cash on cash: 3.87% Traditional cash on cash: 3.23% Airbnb Rental Income: $4157 Traditional Rental Income: $2925 Airbnb ROI: 3.87% Traditional ROI: 3.23%
855 S Waukeenah St Monticello, FL Stunning New Construction recently built by Southern Construction. Centrally located in do...	4 beds \| 3 baths \| 1,798 sq.ft.	$480,000	Airbnb cash on cash: 5.2% Traditional cash on cash: 3.49% Airbnb Rental Income: $4157 Traditional Rental Income: $2508 Airbnb ROI: 5.2% Traditional ROI: 3.49%
64 Sanctuary Dr Monticello, FL Just WOW this beautiful new construction home, with top-of-the-line custom finishes. This ...	4 beds \| 2 baths \| 1,945 sq.ft.	$555,000	Airbnb cash on cash: 5.08% Traditional cash on cash: 3.44% Airbnb Rental Income: $4157 Traditional Rental Income: $2427 Airbnb ROI: 5.08% Traditional ROI: 3.44%
104 Pine Cone Dr Monticello, FL This gorgeous, 3-bedroom, 2-bath modular home, recently renovated by Paul Davis, combines ...	3 beds \| 2 baths \| 1,740 sq.ft.	$275,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 5.24% Airbnb Rental Income: $788 Traditional Rental Income: $1916 Airbnb ROI: -0.3% Traditional ROI: 5.24%
81 Old Tung Grove Rd Monticello, FL New Construction move in ready. Sacious over 2300 sq fr. with upstairs bonus room with bat...	4 beds \| 3 baths \| 2,365 sq.ft.	$725,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.72% Airbnb Rental Income: $4157 Traditional Rental Income: $3289 Airbnb ROI: 3.7% Traditional ROI: 3.72%
1515 Tennessee Avenue Monticello, FL Brimming with rustic charm, this 2 bedroom, 2 bathroom home sits on .29 acres just outside...	2 beds \| 2 baths \| 1,096 sq.ft.	$165,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 6.85% Airbnb Rental Income: $702 Traditional Rental Income: $1511 Airbnb ROI: -0.24% Traditional ROI: 6.85%
930 E Pearl St 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.	$449,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 7.33% Airbnb Rental Income: $4157 Traditional Rental Income: $3787 Airbnb ROI: 6.11% Traditional ROI: 7.33%
2664 A W Washington Hwy 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: 6.81% Airbnb Rental Income: $null Traditional Rental Income: $2749 Airbnb ROI: N/A Traditional ROI: 6.81%
237 Valley View Ct Monticello, FL This is an actual sunset over a 15 minute period in mid-October. Experience gorgeous sunse...	5 beds \| 3 baths \| 5,590 sq.ft.	$1,175,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $5093 Airbnb ROI: N/A Traditional ROI: 2.98%
950 E Pearl Street Monticello, FL Charming 1955 Cottage in the Heart of Monticello,Fl. Welcome home to this cozy yet surpris...	3 beds \| 2 baths \| 1,855 sq.ft.	$300,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 6.42% Airbnb Rental Income: $788 Traditional Rental Income: $2296 Airbnb ROI: -0.06% Traditional ROI: 6.42%
84 Lakeside Rd Monticello, FL This beautifully maintained modular home sits on 2.77 acres, offering peaceful waterfront ...	3 beds \| 2 baths \| 2,268 sq.ft.	$375,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 4.51% Airbnb Rental Income: $788 Traditional Rental Income: $2185 Airbnb ROI: -0.37% Traditional ROI: 4.51%
1627 Lloyd Creek Rd Monticello, FL Enjoy the gorgeous water views from the porch of this like-new, 2022 built home! A Gated d...	3 beds \| 2 baths \| 2,400 sq.ft.	$700,000	Airbnb cash on cash: -1.31% Traditional cash on cash: 2.14% Airbnb Rental Income: $788 Traditional Rental Income: $2718 Airbnb ROI: -1.31% Traditional ROI: 2.14%
159 W Notre Dame St Monticello, FL A perfect redevelopment opportunity or your next home or investment property awaits! Lot c...	N/A beds \| N/A baths \| 600 sq.ft.	$120,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 7.94% Airbnb Rental Income: $702 Traditional Rental Income: $1197 Airbnb ROI: 1.02% Traditional ROI: 7.94%
756 Frank Lacy Rd Monticello, FL Welcome to your new farmhouse in beautiful Jefferson County! This peaceful property is loc...	3 beds \| 2 baths \| 2,432 sq.ft.	$350,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 4.88% Airbnb Rental Income: $788 Traditional Rental Income: $2222 Airbnb ROI: -0.46% Traditional ROI: 4.88%
463 Murmuring Creek Rd Monticello, FL Move in ready home on over 5 acres in beautiful Monticello Florida. Newer Roof 2024, Fresh...	3 beds \| 2 baths \| 1,292 sq.ft.	$190,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 6.51% Airbnb Rental Income: $788 Traditional Rental Income: $1685 Airbnb ROI: 0.09% Traditional ROI: 6.51%
285 Mallard Ln Monticello, FL *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this ...	3 beds \| 2 baths \| 2,000 sq.ft.	$434,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 3.96% Airbnb Rental Income: $788 Traditional Rental Income: $2461 Airbnb ROI: -0.89% Traditional ROI: 3.96%
54 Woodland Drive Monticello, FL One or more photos have been virtually staged (fire in fireplace). Welcome to this beautif...	4 beds \| 3 baths \| 2,032 sq.ft.	$485,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 4.23% Airbnb Rental Income: $4157 Traditional Rental Income: $2660 Airbnb ROI: 5.59% Traditional ROI: 4.23%
1511 Spring Hollow Rd Monticello, FL Charming home on large .87 acre lot in established subdivision. Sunporch overlooks wooded ...	3 beds \| 2 baths \| 1,338 sq.ft.	$269,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 4.57% Airbnb Rental Income: $788 Traditional Rental Income: $1730 Airbnb ROI: -0.41% Traditional ROI: 4.57%
655 N Cherry Street Monticello, FL New construction in the heart of Monticello's Historic District! This beautifully built 1,...	2 beds \| 2 baths \| 1,092 sq.ft.	$244,900	Airbnb cash on cash: -0.57% Traditional cash on cash: 4.82% Airbnb Rental Income: $702 Traditional Rental Income: $1645 Airbnb ROI: -0.57% Traditional ROI: 4.82%
165 CROOKED CREEK Lane Monticello, FL Welcome to 165 Crooked Creek Lane in Monticello, Florida-a beautifully maintained home sit...	3 beds \| 2 baths \| 1,858 sq.ft.	$465,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 3.1% Airbnb Rental Income: $788 Traditional Rental Income: $2261 Airbnb ROI: -1.02% Traditional ROI: 3.1%
963 Quail Ln Monticello, FL Great location for this property in Lloyd Acres. The property has 2.26 acres of partially ...	3 beds \| 2 baths \| 1,440 sq.ft.	$179,900	Airbnb cash on cash: -0.38% Traditional cash on cash: 7.12% Airbnb Rental Income: $788 Traditional Rental Income: $1821 Airbnb ROI: -0.38% Traditional ROI: 7.12%
1090 Partridge Ln Monticello, FL Currently under construction. Interior pictures are from a previous model home. Approximat...	3 beds \| 2 baths \| 1,351 sq.ft.	$294,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 4.23% Airbnb Rental Income: $788 Traditional Rental Income: $1790 Airbnb ROI: -0.53% Traditional ROI: 4.23%
728 Turney Anderson Rd Monticello, FL A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home cap...	3 beds \| 2 baths \| 4,383 sq.ft.	$999,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.92% Airbnb Rental Income: $788 Traditional Rental Income: $2289 Airbnb ROI: -1.04% Traditional ROI: 0.92%
350 Bowman St Monticello, FL New construction; very convenient to downtown; house is close to completion - should be re...	3 beds \| 2 baths \| 1,235 sq.ft.	$244,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 6.35% Airbnb Rental Income: $788 Traditional Rental Income: $1906 Airbnb ROI: 0.13% Traditional ROI: 6.35%

Real Estate investment in Monticello, FL

There are 42 properties for sale in the city of Monticello . The median list price in Monticello is $325,000 and the average price per square foot is $156. In February 2026, the average monthly cash on cash return in Monticello is 5.00%. The average monthly rental income in Monticello is $2,216.

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

There are 42 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

79 Lakeside Rd

Monticello, FL

3 beds | 2 baths | 3,054 sq.ft.

$519,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $788

Traditional Rental Income: $3508

Airbnb ROI: -1.21%

Traditional ROI: 4.26%

155 E Seminole Ave

Monticello, FL

4 beds | 3 baths | 2,223 sq.ft.

$325,000

Airbnb cash on cash: 8.3%

Traditional cash on cash: 6.54%

Airbnb Rental Income: $4157

Traditional Rental Income: $2738

Airbnb ROI: 8.3%

Traditional ROI: 6.54%

354 Pine Cone Dr

Monticello, FL

3 beds | 2 baths | 1,604 sq.ft.

$317,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $788

Traditional Rental Income: $1449

Airbnb ROI: -0.66%

Traditional ROI: 2.55%

1160 E Washington St

Monticello, FL

3 beds | 1 baths | 1,334 sq.ft.

$252,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $788

Traditional Rental Income: $1257

Airbnb ROI: -0.31%

Traditional ROI: 3.01%

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: 5.86%

Airbnb Rental Income: $788

Traditional Rental Income: $2817

Airbnb ROI: -0.82%

Traditional ROI: 5.86%

515 E Palmer Mill Rd

Monticello, FL

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

$579,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $788

Traditional Rental Income: $3203

Airbnb ROI: -0.81%

Traditional ROI: 4.24%

107 Tarn Way

Monticello, FL

3 beds | 2 baths | 1,774 sq.ft.

$449,900

Airbnb cash on cash: -1.03%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $788

Traditional Rental Income: $2210

Airbnb ROI: -1.03%

Traditional ROI: 3.11%

3827 N Jefferson St

Monticello, FL

3 beds | 3 baths | 3,026 sq.ft.

$499,500

Airbnb cash on cash: -0.28%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $788

Traditional Rental Income: $2666

Airbnb ROI: -0.28%