Real Estate Investment Properties for Sale in Middleburg, FL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2030 WAYFARE Lane MIDDLEBURG, FL Discover the perfect blend of space, privacy, and opportunity at 2030 Wayfare Ln. Situated...	4 beds \| 3 baths \| 2,184 sq.ft.	$559,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 3.93% Airbnb Rental Income: $5300 Traditional Rental Income: $3020 Airbnb ROI: 6.24% Traditional ROI: 3.93%
4395 COTTON GIN Court MIDDLEBURG, FL Country charm and nature's serenity come together on this private 1-acre cul-de-sac retrea...	3 beds \| 2 baths \| 1,801 sq.ft.	$475,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 2.15% Airbnb Rental Income: $984 Traditional Rental Income: $2057 Airbnb ROI: -1.05% Traditional ROI: 2.15%
4141 SIDEWINDER Trail MIDDLEBURG, FL Presenting 4141 Sidewinder Trl as a residence featuring all stainless steel appliances, an...	4 beds \| 3 baths \| 2,610 sq.ft.	$495,000	Airbnb cash on cash: 7.69% Traditional cash on cash: 8.53% Airbnb Rental Income: $5300 Traditional Rental Income: $4617 Airbnb ROI: 7.69% Traditional ROI: 8.53%
1884 PARADISE MOORINGS Boulevard MIDDLEBURG, FL Welcome to this beautifully maintained home located in Paradise Moorings a gated waterfron...	4 beds \| 3 baths \| 3,516 sq.ft.	$648,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 3.11% Airbnb Rental Income: $5300 Traditional Rental Income: $3189 Airbnb ROI: 4.83% Traditional ROI: 3.11%
3024 LONGLEAF RANCH Circle MIDDLEBURG, FL Welcome to 3024 Longleaf Ranch Circle, a beautifully maintained home located in the desira...	4 beds \| 2 baths \| 1,728 sq.ft.	$425,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 2.83% Airbnb Rental Income: $5300 Traditional Rental Income: $2121 Airbnb ROI: 8.12% Traditional ROI: 2.83%
4732 SADDLEHORN Trail MIDDLEBURG, FL Private 1.1-acre waterfront retreat offering exceptional privacy, space, & refined indoor-...	5 beds \| 3 baths \| 3,686 sq.ft.	$849,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $5233 Airbnb ROI: N/A Traditional ROI: 4.63%
4072 SCENIC Drive MIDDLEBURG, FL Creekside Charm Welcome to your peaceful retreat nestled along a scenic creek, offering th...	3 beds \| 2 baths \| 1,632 sq.ft.	$510,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 3.04% Airbnb Rental Income: $984 Traditional Rental Income: $2579 Airbnb ROI: -1.04% Traditional ROI: 3.04%
1818 FARM Way MIDDLEBURG, FL Welcome home to this 3-bedroom, 2-bath pool home in the Orange Park South community of Mid...	3 beds \| 2 baths \| 1,298 sq.ft.	$299,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 4.19% Airbnb Rental Income: $984 Traditional Rental Income: $1965 Airbnb ROI: -0.53% Traditional ROI: 4.19%
3938 SUNSET SKY Road MIDDLEBURG, FL * Welcome to 3938 Sunset Sky, a one-of-a-kind modern log cabin retreat set on over 5 fully...	3 beds \| 2 baths \| 2,056 sq.ft.	$995,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 1.18% Airbnb Rental Income: $984 Traditional Rental Income: $2807 Airbnb ROI: -1.17% Traditional ROI: 1.18%
1998 LENOX Court MIDDLEBURG, FL Welcome Home! This gorgeous home a brand-new: Kitchen, Stainless Steel Appliances, Oven, R...	3 beds \| 3 baths \| 2,152 sq.ft.	$368,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 7.89% Airbnb Rental Income: $984 Traditional Rental Income: $3512 Airbnb ROI: -0.45% Traditional ROI: 7.89%
1703 PELICAN Place MIDDLEBURG, FL Experience the best of waterfront living on beautiful Doctors Lake in this fully renovated...	4 beds \| 3 baths \| 2,659 sq.ft.	$1,365,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 1.37% Airbnb Rental Income: $5300 Traditional Rental Income: $4226 Airbnb ROI: 1.38% Traditional ROI: 1.37%
4505 RANCH PINES Way MIDDLEBURG, FL Welcome to 4505 Ranch Pines Way-where space, privacy, and comfort come together in the hea...	4 beds \| 2 baths \| 1,867 sq.ft.	$389,000	Airbnb cash on cash: 9.4% Traditional cash on cash: 3.41% Airbnb Rental Income: $5300 Traditional Rental Income: $2043 Airbnb ROI: 9.4% Traditional ROI: 3.41%
1943 HUNTERS TRACE Circle MIDDLEBURG, FL Welcome home to this cozy and well-kept 3-bedroom, 2-bath gem offering 1,228 square feet o...	3 beds \| 2 baths \| 1,228 sq.ft.	$266,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.33% Airbnb Rental Income: $984 Traditional Rental Income: $1730 Airbnb ROI: -0.05% Traditional ROI: 4.33%
3798 BEDFORD Drive MIDDLEBURG, FL Step inside & be instantly welcomed by soaring ceilings and an abundance of natural light ...	5 beds \| 3 baths \| 2,496 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $3386 Airbnb ROI: N/A Traditional ROI: 6.86%
1840 YUKON Court MIDDLEBURG, FL Short Sale. Welcome Home! This adorable 3-bedroom, 2-bathroom home offers so much potentia...	3 beds \| 2 baths \| 1,272 sq.ft.	$244,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 6.73% Airbnb Rental Income: $984 Traditional Rental Income: $2180 Airbnb ROI: 0.02% Traditional ROI: 6.73%
1881 SAGE CREEK Place MIDDLEBURG, FL Assumable VA 2.5% Loan! Beautiful 3/3 model-like home in a RARE gated 55+ active adult com...	3 beds \| 3 baths \| 2,031 sq.ft.	$375,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 4.27% Airbnb Rental Income: $984 Traditional Rental Income: $2490 Airbnb ROI: -1.01% Traditional ROI: 4.27%
3251 LOBLOLLY PINE Court MIDDLEBURG, FL Approved Short Sale. Discover easy, one-level living in this beautifully maintained 3-bedr...	3 beds \| 2 baths \| 1,507 sq.ft.	$286,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 4.38% Airbnb Rental Income: $984 Traditional Rental Income: $2016 Airbnb ROI: -0.76% Traditional ROI: 4.38%
2929 LUCILLE LANE MIDDLEBURG, FL NEW INCENTIVES: 2% SELLER CREDIT FOR CLOSING COSTS . Donât miss out! Welcome all buyer...	3 beds \| 3 baths \| 1,877 sq.ft.	$339,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 6.31% Airbnb Rental Income: $984 Traditional Rental Income: $2744 Airbnb ROI: -0.31% Traditional ROI: 6.31%
5665 MAVERICK MIDDLEBURG, FL This amazing 40 acre property is located on a county-maintained road and includes marketab...	2 beds \| 2 baths \| 1,256 sq.ft.	$800,000	Airbnb cash on cash: -1% Traditional cash on cash: 0.97% Airbnb Rental Income: $634 Traditional Rental Income: $1812 Airbnb ROI: -1% Traditional ROI: 0.97%
817 SUNNY STROLL Drive MIDDLEBURG, FL Welcome to 817 Sunny Stroll in the heart of Middleburg. This beautifully maintained home o...	4 beds \| 3 baths \| 2,508 sq.ft.	$395,000	Airbnb cash on cash: 8.43% Traditional cash on cash: 7.46% Airbnb Rental Income: $5300 Traditional Rental Income: $3869 Airbnb ROI: 8.43% Traditional ROI: 7.46%
2907 LUCILLE Lane MIDDLEBURG, FL Built in 2023, this stunning 3-bedroom, 2-bathroom home offers modern living at its finest...	3 beds \| 2 baths \| 1,498 sq.ft.	$300,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 6.52% Airbnb Rental Income: $984 Traditional Rental Income: $2679 Airbnb ROI: -0.73% Traditional ROI: 6.52%
1124 PERSIMMON Drive MIDDLEBURG, FL Welcome to the upgraded home you've been waiting for! Own complete luxury with this stunni...	3 beds \| 2 baths \| 1,867 sq.ft.	$335,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 5.68% Airbnb Rental Income: $984 Traditional Rental Income: $2869 Airbnb ROI: -1.43% Traditional ROI: 5.68%
3559 WHISPER CREEK Boulevard MIDDLEBURG, FL CORNER Lot Home- Forget the stress of ''hidden costs''--NO CDD fees and every major system...	3 beds \| 2 baths \| 1,465 sq.ft.	$350,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 4.3% Airbnb Rental Income: $984 Traditional Rental Income: $2183 Airbnb ROI: -0.42% Traditional ROI: 4.3%
2990 RAVINES Road #1422 MIDDLEBURG, FL Tucked beneath the trees in the gated community of The Ravines, this thoughtfully designed...	1 beds \| 2 baths \| 848 sq.ft.	$144,900	Airbnb cash on cash: 1.19% Traditional cash on cash: 5.5% Airbnb Rental Income: $963 Traditional Rental Income: $1212 Airbnb ROI: 1.19% Traditional ROI: 5.5%
3165 RAVINES Road #3601 MIDDLEBURG, FL Charming Studio Condo in Private Gated Community Escape to your serene oasis in this delig...	1 beds \| 1 baths \| 420 sq.ft.	$139,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 8.23% Airbnb Rental Income: $963 Traditional Rental Income: $1693 Airbnb ROI: 0.13% Traditional ROI: 8.23%
4619 PINE LAKE Drive MIDDLEBURG, FL BRAND NEW ROOF INSTALLED APRIL 2026! Welcome to this inviting 3-bedroom, 2-bathroom home n...	3 beds \| 2 baths \| 1,901 sq.ft.	$339,990	Airbnb cash on cash: -1.15% Traditional cash on cash: 4.83% Airbnb Rental Income: $984 Traditional Rental Income: $2541 Airbnb ROI: -1.15% Traditional ROI: 4.83%
2349 TIGRESS Lane MIDDLEBURG, FL SELLER FINANCING AVAILABLE! No Bank Approval Needed! Corner lot Screend in POOL Home in th...	3 beds \| 2 baths \| 1,661 sq.ft.	$389,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 4.04% Airbnb Rental Income: $984 Traditional Rental Income: $2311 Airbnb ROI: -0.57% Traditional ROI: 4.04%
3832 GREAT FALLS Loop MIDDLEBURG, FL New Roof! Excellent 4/3 home with a classic stucco and stone exterior. The entry opens...	4 beds \| 3 baths \| 2,058 sq.ft.	$355,000	Airbnb cash on cash: 9.75% Traditional cash on cash: 4.12% Airbnb Rental Income: $5300 Traditional Rental Income: $2352 Airbnb ROI: 9.75% Traditional ROI: 4.12%
5012 LAUREL Street MIDDLEBURG, FL Tranquil, private oasis built in 2024! Drive through the gated front to this custom home t...	4 beds \| 3 baths \| 2,245 sq.ft.	$680,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 5.01% Airbnb Rental Income: $5300 Traditional Rental Income: $3938 Airbnb ROI: 5.47% Traditional ROI: 5.01%
2697 TINA Lane MIDDLEBURG, FL Step into peace of mind with this solid brick and concrete block home with a 1 car garage,...	3 beds \| 2 baths \| 1,574 sq.ft.	$274,999	Airbnb cash on cash: -0.36% Traditional cash on cash: 6.07% Airbnb Rental Income: $984 Traditional Rental Income: $2297 Airbnb ROI: -0.36% Traditional ROI: 6.07%
187 SORREL Street MIDDLEBURG, FL Welcome home to this two-story 4 bedroom, 3 bathroom home with 9' ceilings, located on 1.2...	4 beds \| 3 baths \| 2,046 sq.ft.	$580,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 5.81% Airbnb Rental Income: $5300 Traditional Rental Income: $4058 Airbnb ROI: 6.13% Traditional ROI: 5.81%
817 RIVERTREE Place MIDDLEBURG, FL Built in 2024 and still practically brand new, this spacious end-unit townhome offers the ...	3 beds \| 3 baths \| 1,340 sq.ft.	$269,990	Airbnb cash on cash: -0.67% Traditional cash on cash: 5.02% Airbnb Rental Income: $984 Traditional Rental Income: $2080 Airbnb ROI: -0.67% Traditional ROI: 5.02%
3806 FEATHERSTONE Court MIDDLEBURG, FL Breathtaking Lennar NextGen 4/4 home in one of the largest lot in Greyhawk! Soaring 12-foo...	4 beds \| 4 baths \| 3,008 sq.ft.	$629,900	Airbnb cash on cash: 4.49% Traditional cash on cash: 6.48% Airbnb Rental Income: $5300 Traditional Rental Income: $5397 Airbnb ROI: 4.49% Traditional ROI: 6.48%
1847 AMBERLY Drive MIDDLEBURG, FL Assumable VA loan at 3.375%! Smarter living starts here in this beautifully maintained, en...	4 beds \| 3 baths \| 2,075 sq.ft.	$423,000	Airbnb cash on cash: 8.4% Traditional cash on cash: 4.95% Airbnb Rental Income: $5300 Traditional Rental Income: $2858 Airbnb ROI: 8.4% Traditional ROI: 4.95%

Real Estate investment in Middleburg, FL

There are 155 properties for sale in the city of Middleburg . The median list price in Middleburg is $337,450 and the average price per square foot is $173. In May 2026, the average monthly cash on cash return in Middleburg is 5.00%. The average monthly rental income in Middleburg is $2,294.

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

There are 155 investment properties available for sale in Middleburg.

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

The ROI for Long-Term is higher than the Short-Term in Middleburg with average rental income of $2,294.

Your search for investment property begins and ends here

Investment Property for Sale in Middleburg, FL

2030 WAYFARE Lane

MIDDLEBURG, FL

4 beds | 3 baths | 2,184 sq.ft.

$559,000

Airbnb cash on cash: 6.24%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $5300

Traditional Rental Income: $3020

Airbnb ROI: 6.24%

Traditional ROI: 3.93%

4395 COTTON GIN Court

MIDDLEBURG, FL

3 beds | 2 baths | 1,801 sq.ft.

$475,000

Airbnb cash on cash: -1.05%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $984

Traditional Rental Income: $2057

Airbnb ROI: -1.05%

Traditional ROI: 2.15%

4141 SIDEWINDER Trail

MIDDLEBURG, FL

4 beds | 3 baths | 2,610 sq.ft.

$495,000

Airbnb cash on cash: 7.69%

Traditional cash on cash: 8.53%

Airbnb Rental Income: $5300

Traditional Rental Income: $4617

Airbnb ROI: 7.69%

Traditional ROI: 8.53%

1884 PARADISE MOORINGS Boulevard

MIDDLEBURG, FL

4 beds | 3 baths | 3,516 sq.ft.

$648,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $5300

Traditional Rental Income: $3189

Airbnb ROI: 4.83%

Traditional ROI: 3.11%

3024 LONGLEAF RANCH Circle

MIDDLEBURG, FL

4 beds | 2 baths | 1,728 sq.ft.

$425,000

Airbnb cash on cash: 8.12%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $5300

Traditional Rental Income: $2121

Airbnb ROI: 8.12%

Traditional ROI: 2.83%

4732 SADDLEHORN Trail

MIDDLEBURG, FL

5 beds | 3 baths | 3,686 sq.ft.

$849,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.63%

Airbnb Rental Income: $null

Traditional Rental Income: $5233

Airbnb ROI: N/A

Traditional ROI: 4.63%

4072 SCENIC Drive

MIDDLEBURG, FL

3 beds | 2 baths | 1,632 sq.ft.

$510,000

Airbnb cash on cash: -1.04%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $984

Traditional Rental Income: $2579

Airbnb ROI: -1.04%

Traditional ROI: 3.04%

1818 FARM Way

MIDDLEBURG, FL

3 beds | 2 baths | 1,298 sq.ft.

$299,900

Airbnb cash on cash: -0.53%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $984

Traditional Rental Income: $1965

Airbnb ROI: -0.53%