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
2482 GLOW WOOD Court MIDDLEBURG, FL Price Improvement AND Open House 6/28 12:30-2:30. Backyard Retreat + Expansive Granite Isl...	3 beds \| 2 baths \| 1,942 sq.ft.	$430,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 3.3% Airbnb Rental Income: $984 Traditional Rental Income: $1919 Airbnb ROI: 0.1% Traditional ROI: 3.3%
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.	$450,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 2.33% Airbnb Rental Income: $984 Traditional Rental Income: $2057 Airbnb ROI: -1.06% Traditional ROI: 2.33%
1456 COOPERS HAWK Way MIDDLEBURG, FL Welcome home to a spacious, light-filled home located on a quiet dead-end street, perfect ...	4 beds \| 3 baths \| 2,753 sq.ft.	$530,000	Airbnb cash on cash: 5.86% Traditional cash on cash: 3.66% Airbnb Rental Income: $5300 Traditional Rental Income: $3138 Airbnb ROI: 5.86% Traditional ROI: 3.66%
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.	$490,000	Airbnb cash on cash: 7.78% Traditional cash on cash: 8.63% Airbnb Rental Income: $5300 Traditional Rental Income: $4617 Airbnb ROI: 7.78% Traditional ROI: 8.63%
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.	$630,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.23% Airbnb Rental Income: $5300 Traditional Rental Income: $3189 Airbnb ROI: 4.99% Traditional ROI: 3.23%
3860 MAGNOLIA Street MIDDLEBURG, FL 235 FEET OF WATERFRONT FOOTAGE! 1.933 ACRES ON BLACK CREEK! HOUSE PAD X FLOOD ZONE NEW MET...	4 beds \| 3 baths \| 2,510 sq.ft.	$629,000	Airbnb cash on cash: 5.62% Traditional cash on cash: 4.79% Airbnb Rental Income: $5300 Traditional Rental Income: $3741 Airbnb ROI: 5.62% Traditional ROI: 4.79%
3462 TALISMAN Drive MIDDLEBURG, FL This adorable, light and airy home has been almost completely remodled! Solid concrete blo...	3 beds \| 2 baths \| 1,158 sq.ft.	$280,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 3.68% Airbnb Rental Income: $1992 Traditional Rental Income: $1666 Airbnb ROI: 2.94% Traditional ROI: 3.68%
4075 SUNRISE FARMS Road MIDDLEBURG, FL Step into the perfect mix of vintage charm and modern convenience in this beautifully upda...	2 beds \| 2 baths \| 1,373 sq.ft.	$349,900	Airbnb cash on cash: -0.99% Traditional cash on cash: 3.77% Airbnb Rental Income: $634 Traditional Rental Income: $1903 Airbnb ROI: -0.99% Traditional ROI: 3.77%
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.	$845,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $5233 Airbnb ROI: N/A Traditional ROI: 4.66%
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.	$295,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.28% Airbnb Rental Income: $984 Traditional Rental Income: $1965 Airbnb ROI: -0.52% Traditional ROI: 4.28%
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.	$353,500	Airbnb cash on cash: -0.43% Traditional cash on cash: 8.25% Airbnb Rental Income: $984 Traditional Rental Income: $3512 Airbnb ROI: -0.43% Traditional ROI: 8.25%
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.	$1,325,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 1.47% Airbnb Rental Income: $5300 Traditional Rental Income: $4226 Airbnb ROI: 1.47% Traditional ROI: 1.47%
2817 CAMEL Circle MIDDLEBURG, FL This charming 3-year-old country home sits on 1.53 serene acres, offering the perfect mix ...	4 beds \| 3 baths \| 2,081 sq.ft.	$529,900	Airbnb cash on cash: 7.28% Traditional cash on cash: 4.09% Airbnb Rental Income: $5300 Traditional Rental Income: $2647 Airbnb ROI: 7.28% Traditional ROI: 4.09%
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.	$265,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.35% Airbnb Rental Income: $984 Traditional Rental Income: $1730 Airbnb ROI: -0.04% Traditional ROI: 4.35%
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%
3083 ZEYNO Drive MIDDLEBURG, FL Welcome home to this beautifully updated townhome in a quiet, amenity-rich Middleburg comm...	3 beds \| 3 baths \| 1,889 sq.ft.	$270,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 9.41% Airbnb Rental Income: $984 Traditional Rental Income: $2938 Airbnb ROI: 0.35% Traditional ROI: 9.41%
1881 SAGE CREEK Place MIDDLEBURG, FL Offering 3% buyers closing costs with acceptable Offer! Beautiful 3/3 model-like home in a...	3 beds \| 3 baths \| 2,031 sq.ft.	$370,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 4.34% Airbnb Rental Income: $984 Traditional Rental Income: $2490 Airbnb ROI: -1.01% Traditional ROI: 4.34%
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 Welcome all buyers! Built in 2023, still under KB HOME STRUCTURE WARRANTY. NO CDD and priv...	3 beds \| 3 baths \| 1,877 sq.ft.	$335,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 6.41% Airbnb Rental Income: $984 Traditional Rental Income: $2744 Airbnb ROI: -0.3% Traditional ROI: 6.41%
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%
3906 HEATHERBROOK Place MIDDLEBURG, FL Welcome to GreyHawk ! This beautiful two-story home offers 4 bedrooms, 2.5 bathrooms, thou...	4 beds \| 3 baths \| 2,491 sq.ft.	$435,000	Airbnb cash on cash: 8.53% Traditional cash on cash: 4.22% Airbnb Rental Income: $5300 Traditional Rental Income: $2474 Airbnb ROI: 8.53% Traditional ROI: 4.22%
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%
2704 TINA Lane MIDDLEBURG, FL Charming 3-Bed, 2-Bath Brick home nestled in the peaceful Evergreen community. The home fe...	3 beds \| 2 baths \| 1,084 sq.ft.	$249,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 5.99% Airbnb Rental Income: $984 Traditional Rental Income: $1999 Airbnb ROI: 0.18% Traditional ROI: 5.99%
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.	$325,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 5.88% Airbnb Rental Income: $984 Traditional Rental Income: $2869 Airbnb ROI: -1.45% Traditional ROI: 5.88%
3559 WHISPER CREEK Boulevard MIDDLEBURG, FL OPEN HOUSE- JUNE 20TH- 11 AM TO 2 PM~! CORNER Lot Home- NO CDD !!! Forget the stress of ''...	3 beds \| 2 baths \| 1,465 sq.ft.	$339,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 4.47% Airbnb Rental Income: $984 Traditional Rental Income: $2183 Airbnb ROI: -0.41% Traditional ROI: 4.47%
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%
94 CONIFER Circle MIDDLEBURG, FL Step into 94 Conifer Cir, a standalone residence with a straightforward, functional layout...	3 beds \| 2 baths \| 1,568 sq.ft.	$310,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 5.14% Airbnb Rental Income: $984 Traditional Rental Income: $2019 Airbnb ROI: 0.38% Traditional ROI: 5.14%
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.	$125,900	Airbnb cash on cash: 0.25% Traditional cash on cash: 9.15% Airbnb Rental Income: $963 Traditional Rental Income: $1693 Airbnb ROI: 0.25% Traditional ROI: 9.15%
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%
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%

Real Estate investment in Middleburg, FL

There are 159 properties for sale in the city of Middleburg . The median list price in Middleburg is $377,674 and the average price per square foot is $195. In July 2026, the average monthly cash on cash return in Middleburg is 5.00%. The average monthly rental income in Middleburg is $2,152.

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

There are 159 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 $2,152.

Your search for investment property begins and ends here

Investment Property for Sale in Middleburg, FL

2482 GLOW WOOD Court

MIDDLEBURG, FL

3 beds | 2 baths | 1,942 sq.ft.

$430,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $984

Traditional Rental Income: $1919

Airbnb ROI: 0.1%

Traditional ROI: 3.3%

4395 COTTON GIN Court

MIDDLEBURG, FL

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

$450,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: 2.33%

Airbnb Rental Income: $984

Traditional Rental Income: $2057

Airbnb ROI: -1.06%

Traditional ROI: 2.33%

1456 COOPERS HAWK Way

MIDDLEBURG, FL

4 beds | 3 baths | 2,753 sq.ft.

$530,000

Airbnb cash on cash: 5.86%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $5300

Traditional Rental Income: $3138

Airbnb ROI: 5.86%

Traditional ROI: 3.66%

4141 SIDEWINDER Trail

MIDDLEBURG, FL

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

$490,000

Airbnb cash on cash: 7.78%

Traditional cash on cash: 8.63%

Airbnb Rental Income: $5300

Traditional Rental Income: $4617

Airbnb ROI: 7.78%

Traditional ROI: 8.63%

1884 PARADISE MOORINGS Boulevard

MIDDLEBURG, FL

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

$630,000

Airbnb cash on cash: 4.99%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $5300

Traditional Rental Income: $3189

Airbnb ROI: 4.99%

Traditional ROI: 3.23%

3860 MAGNOLIA Street

MIDDLEBURG, FL

4 beds | 3 baths | 2,510 sq.ft.

$629,000

Airbnb cash on cash: 5.62%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $5300

Traditional Rental Income: $3741

Airbnb ROI: 5.62%

Traditional ROI: 4.79%

3462 TALISMAN Drive

MIDDLEBURG, FL

3 beds | 2 baths | 1,158 sq.ft.

$280,000

Airbnb cash on cash: 2.94%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $1992

Traditional Rental Income: $1666

Airbnb ROI: 2.94%

Traditional ROI: 3.68%

4075 SUNRISE FARMS Road

MIDDLEBURG, FL

2 beds | 2 baths | 1,373 sq.ft.

$349,900

Airbnb cash on cash: -0.99%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $634

Traditional Rental Income: $1903

Airbnb ROI: -0.99%