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
2982 CHIEF RIDAUGHT Trail MIDDLEBURG, FL Unbeatable value: 2.75% Assumable Interest rate! Stop your search! This is a rare opportun...	4 beds \| 2 baths \| 1,975 sq.ft.	$325,000	Airbnb cash on cash: 8.68% Traditional cash on cash: 5.57% Airbnb Rental Income: $4214 Traditional Rental Income: $2371 Airbnb ROI: 8.68% Traditional ROI: 5.57%
2482 GLOW WOOD Court MIDDLEBURG, FL Price Improvement AND Open House 7/11 12:00-4:00. Backyard Retreat + Expansive Granite Isl...	3 beds \| 2 baths \| 1,942 sq.ft.	$430,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 3.3% Airbnb Rental Income: $1873 Traditional Rental Income: $1919 Airbnb ROI: 1.94% Traditional ROI: 3.3%
3201 FIRESIDE Drive MIDDLEBURG, FL Welcome to this charming brick home on a cul-de-sac! Offering timeless curb appeal and a t...	3 beds \| 2 baths \| 1,900 sq.ft.	$375,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 3.08% Airbnb Rental Income: $1873 Traditional Rental Income: $2047 Airbnb ROI: 1.16% Traditional ROI: 3.08%
721 TARA FARMS Drive MIDDLEBURG, FL Discover the perfect blend of modern comfort and Florida's natural beauty with this beauti...	4 beds \| 3 baths \| 1,863 sq.ft.	$456,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 2.46% Airbnb Rental Income: $4214 Traditional Rental Income: $2405 Airbnb ROI: 4.61% Traditional ROI: 2.46%
3011 ANGORA BAY Drive MIDDLEBURG, FL Lovely like new house w/ 4 Bedrooms & 2 Baths. Located on a corner as you first enter Ango...	4 beds \| 2 baths \| 2,004 sq.ft.	$359,900	Airbnb cash on cash: 7.57% Traditional cash on cash: 4.47% Airbnb Rental Income: $4214 Traditional Rental Income: $2275 Airbnb ROI: 7.57% Traditional ROI: 4.47%
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: 4.03% Traditional cash on cash: 3.66% Airbnb Rental Income: $4214 Traditional Rental Income: $3138 Airbnb ROI: 4.03% Traditional ROI: 3.66%
2882 TUSCARORA Trail MIDDLEBURG, FL Welcome to 2882 Tuscarora Trail in Middleburg! This home offers a fantastic opportunity to...	4 beds \| 2 baths \| 1,714 sq.ft.	$310,000	Airbnb cash on cash: 8.66% Traditional cash on cash: 4.86% Airbnb Rental Income: $4214 Traditional Rental Income: $2216 Airbnb ROI: 8.66% Traditional ROI: 4.86%
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: 5.8% Traditional cash on cash: 8.63% Airbnb Rental Income: $4214 Traditional Rental Income: $4617 Airbnb ROI: 5.8% 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.	$625,900	Airbnb cash on cash: 3.48% Traditional cash on cash: 3.25% Airbnb Rental Income: $4214 Traditional Rental Income: $3189 Airbnb ROI: 3.48% Traditional ROI: 3.25%
1207 CAMP RIDGE Lane MIDDLEBURG, FL Nestled in the family-friendly community of Pine Ridge, 1207 Camp Ridge is a beautifully m...	4 beds \| 2 baths \| 1,896 sq.ft.	$325,000	Airbnb cash on cash: 8.05% Traditional cash on cash: 4.18% Airbnb Rental Income: $4214 Traditional Rental Income: $2141 Airbnb ROI: 8.05% Traditional ROI: 4.18%
2946 LONGLEAF RANCH Circle MIDDLEBURG, FL This 4-bedroom, 2-bathroom home in Longleaf Ranch offers significant potential for an inve...	4 beds \| 3 baths \| 2,362 sq.ft.	$310,000	Airbnb cash on cash: 8.84% Traditional cash on cash: 10.25% Airbnb Rental Income: $4214 Traditional Rental Income: $3733 Airbnb ROI: 8.84% Traditional ROI: 10.25%
3860 MAGNOLIA Street MIDDLEBURG, FL 235 FEET OF WATERFRONT FOOTAGE! 1.933 ACRES ON BLACK CREEK! HOUSE IS HIGH & DRY WITH HOUSE...	4 beds \| 3 baths \| 2,510 sq.ft.	$599,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 5.08% Airbnb Rental Income: $4214 Traditional Rental Income: $3741 Airbnb ROI: 4.33% Traditional ROI: 5.08%
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: 2.57% Traditional cash on cash: 3.68% Airbnb Rental Income: $1873 Traditional Rental Income: $1666 Airbnb ROI: 2.57% Traditional ROI: 3.68%
1695 SANDY HOLLOW Loop MIDDLEBURG, FL Beautiful Florida Oasis! This spacious 3-bedroom, 2-bath home with a versatile 4th flex ro...	3 beds \| 2 baths \| 1,748 sq.ft.	$315,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 1.86% Airbnb Rental Income: $1873 Traditional Rental Income: $1386 Airbnb ROI: 1.81% Traditional ROI: 1.86%
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: -0.57% Traditional cash on cash: 3.77% Airbnb Rental Income: $798 Traditional Rental Income: $1903 Airbnb ROI: -0.57% Traditional ROI: 3.77%
4732 SADDLEHORN Trail MIDDLEBURG, FL 1.1-acre waterfront property - Screened pool - Private fishing dock - 2024 roof. This 4-be...	5 beds \| 3 baths \| 3,686 sq.ft.	$845,900	Airbnb cash on cash: -0.15% Traditional cash on cash: 4.66% Airbnb Rental Income: $1958 Traditional Rental Income: $5233 Airbnb ROI: -0.15% 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.	$287,500	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.41% Airbnb Rental Income: $1873 Traditional Rental Income: $1965 Airbnb ROI: 2.23% Traditional ROI: 4.41%
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: -0.37% Traditional cash on cash: 1.18% Airbnb Rental Income: $1873 Traditional Rental Income: $2807 Airbnb ROI: -0.37% 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: 1.8% Traditional cash on cash: 8.25% Airbnb Rental Income: $1873 Traditional Rental Income: $3512 Airbnb ROI: 1.8% Traditional ROI: 8.25%
747 SUNNY STROLL Drive MIDDLEBURG, FL Your new home awaits in the beautiful neighborhood of Kindle Wood. This bright open 4 bedr...	4 beds \| 3 baths \| 2,477 sq.ft.	$379,900	Airbnb cash on cash: 6.67% Traditional cash on cash: 5.56% Airbnb Rental Income: $4214 Traditional Rental Income: $2925 Airbnb ROI: 6.67% Traditional ROI: 5.56%
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.	$1,290,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 1.56% Airbnb Rental Income: $4214 Traditional Rental Income: $4226 Airbnb ROI: 0.81% Traditional ROI: 1.56%
3178 WAVERING Lane MIDDLEBURG, FL Beautifully maintained 3-bedroom, 2-bath home featuring a versatile flex room perfect for ...	3 beds \| 2 baths \| 1,788 sq.ft.	$320,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 4.14% Airbnb Rental Income: $1873 Traditional Rental Income: $2049 Airbnb ROI: 1.89% Traditional ROI: 4.14%
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.	$519,900	Airbnb cash on cash: 5.57% Traditional cash on cash: 4.18% Airbnb Rental Income: $4214 Traditional Rental Income: $2647 Airbnb ROI: 5.57% Traditional ROI: 4.18%
1937 AMBERLY Drive MIDDLEBURG, FL Welcome home to this beautifully appointed residence overlooking a peaceful preserve in th...	3 beds \| 2 baths \| 1,813 sq.ft.	$350,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 0.78% Airbnb Rental Income: $1873 Traditional Rental Income: $1386 Airbnb ROI: 0.74% Traditional ROI: 0.78%
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.	$267,500	Airbnb cash on cash: 3.3% Traditional cash on cash: 9.51% Airbnb Rental Income: $1873 Traditional Rental Income: $2938 Airbnb ROI: 3.3% Traditional ROI: 9.51%
4153 WEATHERED PINE Court MIDDLEBURG, FL Welcome to this beautiful and extremely well maintained 3/2 home. Upon entering you will h...	3 beds \| 2 baths \| 1,908 sq.ft.	$275,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 5.42% Airbnb Rental Income: $1873 Traditional Rental Income: $2148 Airbnb ROI: 2.43% Traditional ROI: 5.42%
1881 SAGE CREEK Place MIDDLEBURG, FL Beautiful 3/3 model-like home in a RARE gated 55+ active adult community in Middleburg! Lo...	3 beds \| 3 baths \| 2,031 sq.ft.	$350,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.64% Airbnb Rental Income: $1873 Traditional Rental Income: $2490 Airbnb ROI: 1.24% Traditional ROI: 4.64%
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: 1.99% Traditional cash on cash: 4.38% Airbnb Rental Income: $1873 Traditional Rental Income: $2016 Airbnb ROI: 1.99% 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: 2.05% Traditional cash on cash: 6.41% Airbnb Rental Income: $1873 Traditional Rental Income: $2744 Airbnb ROI: 2.05% Traditional ROI: 6.41%
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: 5.99% Traditional cash on cash: 7.46% Airbnb Rental Income: $4214 Traditional Rental Income: $3869 Airbnb ROI: 5.99% Traditional ROI: 7.46%
5684 MAVERICK Road MIDDLEBURG, FL Two Homes. Nearly 1.5 Acres. Fully Renovated. Welcome to the lifestyle you've been searchi...	4 beds \| 3 baths \| 2,324 sq.ft.	$460,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.25% Airbnb Rental Income: $4214 Traditional Rental Income: $2844 Airbnb ROI: 5.36% Traditional ROI: 4.25%
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: 6.3% Traditional cash on cash: 4.22% Airbnb Rental Income: $4214 Traditional Rental Income: $2474 Airbnb ROI: 6.3% Traditional ROI: 4.22%

Real Estate investment in Middleburg, FL

There are 187 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 $194. In August 2026, the average monthly cash on cash return in Middleburg is 5.00%. The average monthly rental income in Middleburg is $2,141.

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

There are 187 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 $2,141.

Your search for investment property begins and ends here

Investment Property for Sale in Middleburg, FL

2982 CHIEF RIDAUGHT Trail

MIDDLEBURG, FL

4 beds | 2 baths | 1,975 sq.ft.

$325,000

Airbnb cash on cash: 8.68%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $4214

Traditional Rental Income: $2371

Airbnb ROI: 8.68%

Traditional ROI: 5.57%

2482 GLOW WOOD Court

MIDDLEBURG, FL

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

$430,000

Airbnb cash on cash: 1.94%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1873

Traditional Rental Income: $1919

Airbnb ROI: 1.94%

Traditional ROI: 3.3%

3201 FIRESIDE Drive

MIDDLEBURG, FL

3 beds | 2 baths | 1,900 sq.ft.

$375,000

Airbnb cash on cash: 1.16%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $1873

Traditional Rental Income: $2047

Airbnb ROI: 1.16%

Traditional ROI: 3.08%

721 TARA FARMS Drive

MIDDLEBURG, FL

4 beds | 3 baths | 1,863 sq.ft.

$456,000

Airbnb cash on cash: 4.61%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $4214

Traditional Rental Income: $2405

Airbnb ROI: 4.61%

Traditional ROI: 2.46%

3011 ANGORA BAY Drive

MIDDLEBURG, FL

4 beds | 2 baths | 2,004 sq.ft.

$359,900

Airbnb cash on cash: 7.57%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $4214

Traditional Rental Income: $2275

Airbnb ROI: 7.57%

Traditional ROI: 4.47%

1456 COOPERS HAWK Way

MIDDLEBURG, FL

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

$530,000

Airbnb cash on cash: 4.03%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $4214

Traditional Rental Income: $3138

Airbnb ROI: 4.03%

Traditional ROI: 3.66%

2882 TUSCARORA Trail

MIDDLEBURG, FL

4 beds | 2 baths | 1,714 sq.ft.

$310,000

Airbnb cash on cash: 8.66%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $4214

Traditional Rental Income: $2216

Airbnb ROI: 8.66%

Traditional ROI: 4.86%

4141 SIDEWINDER Trail

MIDDLEBURG, FL

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

$490,000

Airbnb cash on cash: 5.8%

Traditional cash on cash: 8.63%

Airbnb Rental Income: $4214

Traditional Rental Income: $4617

Airbnb ROI: 5.8%