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
3684 MAIN Street MIDDLEBURG, FL Custom waterfront home on 140 feet of North Fork Black Creek frontage, offering a private ...	3 beds \| 3 baths \| 2,012 sq.ft.	$700,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 2.07% Airbnb Rental Income: $2478 Traditional Rental Income: $2741 Airbnb ROI: 0.74% Traditional ROI: 2.07%
191 MIMOSA Avenue N MIDDLEBURG, FL Oversized 1.14 acre lot. No HOA. Design and upgrade as you like. Storage shed outback offe...	3 beds \| 2 baths \| 1,092 sq.ft.	$234,900	Airbnb cash on cash: 5.69% Traditional cash on cash: 4.22% Airbnb Rental Income: $2478 Traditional Rental Income: $1549 Airbnb ROI: 5.69% Traditional ROI: 4.22%
2482 GLOW WOOD Court MIDDLEBURG, FL Backyard Retreat + Expansive Granite Island \| Pool Home \| Gated \| NO CDD Tucked away on a ...	3 beds \| 2 baths \| 1,942 sq.ft.	$425,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 3.35% Airbnb Rental Income: $2478 Traditional Rental Income: $1919 Airbnb ROI: 3.24% Traditional ROI: 3.35%
3201 FIRESIDE Drive MIDDLEBURG, FL Welcome to this charming brick home on a cul-de-sac! Brand new HVAC! Offering timeless cur...	3 beds \| 2 baths \| 1,900 sq.ft.	$369,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 3.14% Airbnb Rental Income: $2478 Traditional Rental Income: $2047 Airbnb ROI: 2.65% Traditional ROI: 3.14%
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.	$445,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.55% Airbnb Rental Income: $3461 Traditional Rental Income: $2405 Airbnb ROI: 3.24% Traditional ROI: 2.55%
1717 LANDWARD Lane MIDDLEBURG, FL Rare opportunity to own a private waterfront property on one of the largest lots on Doctor...	4 beds \| 3 baths \| 2,575 sq.ft.	$1,075,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 0.5% Airbnb Rental Income: $3461 Traditional Rental Income: $2219 Airbnb ROI: 0.98% Traditional ROI: 0.5%
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: 5.71% Traditional cash on cash: 4.47% Airbnb Rental Income: $3461 Traditional Rental Income: $2275 Airbnb ROI: 5.71% Traditional ROI: 4.47%
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: 6.51% Traditional cash on cash: 4.86% Airbnb Rental Income: $3461 Traditional Rental Income: $2216 Airbnb ROI: 6.51% Traditional ROI: 4.86%
1864 SHERATON LAKES Circle MIDDLEBURG, FL Spacious 4 bed, 3 bath home in Middleburg's Sheraton Lakes! This approximately 1,512 sq. f...	4 beds \| 3 baths \| 1,512 sq.ft.	$259,000	Airbnb cash on cash: 8.1% Traditional cash on cash: 7.06% Airbnb Rental Income: $3461 Traditional Rental Income: $2440 Airbnb ROI: 8.1% Traditional ROI: 7.06%
1884 PARADISE MOORINGS Boulevard MIDDLEBURG, FL Community Wide OPEN HOUSE fri AUG. 7th 2-4, Welcome to this beautifully maintained home lo...	4 beds \| 3 baths \| 3,516 sq.ft.	$625,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 3.25% Airbnb Rental Income: $3461 Traditional Rental Income: $3189 Airbnb ROI: 2.41% Traditional ROI: 3.25%
2946 LONGLEAF RANCH Circle MIDDLEBURG, FL ALL OFFERS AND ALL DOCS MUST BE WET SIGNED PER LENDER!!! This 4-bedroom, 2-bathroom home i...	4 beds \| 3 baths \| 2,362 sq.ft.	$310,000	Airbnb cash on cash: 6.69% Traditional cash on cash: 10.25% Airbnb Rental Income: $3461 Traditional Rental Income: $3733 Airbnb ROI: 6.69% Traditional ROI: 10.25%
1407 HEATHER GLEN Lane MIDDLEBURG, FL Tucked away on a quiet cul-de-sac, this move-in ready 4-bedroom, 2-bath home offers a spac...	4 beds \| 2 baths \| 1,783 sq.ft.	$307,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 3.99% Airbnb Rental Income: $3461 Traditional Rental Income: $1962 Airbnb ROI: 6.53% Traditional ROI: 3.99%
3621 COUNTY ROAD 215 MIDDLEBURG, FL Welcome to your own private slice of country living, where space, comfort, and endless pos...	5 beds \| 4 baths \| 3,178 sq.ft.	$545,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 6.93% Airbnb Rental Income: $3369 Traditional Rental Income: $4704 Airbnb ROI: 2.83% Traditional ROI: 6.93%
4072 SCENIC Drive MIDDLEBURG, FL BOM: No fault of seller or home. MOTIVATED SELLERS Creekside Charm Welcome to your peacefu...	3 beds \| 2 baths \| 1,632 sq.ft.	$495,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.16% Airbnb Rental Income: $2478 Traditional Rental Income: $2579 Airbnb ROI: 1.65% Traditional ROI: 3.16%
1768 REDWOOD Lane MIDDLEBURG, FL Welcome home to this beautifully updated 4-bedroom, 2 bath home offering 1,801 square feet...	4 beds \| 2 baths \| 1,801 sq.ft.	$368,900	Airbnb cash on cash: 5.5% Traditional cash on cash: 3.58% Airbnb Rental Income: $3461 Traditional Rental Income: $2029 Airbnb ROI: 5.5% Traditional ROI: 3.58%
2176 GINHOUSE Drive MIDDLEBURG, FL MUST SEE converted garage workspace, insulated and AC. Plus 2 large storage sheds. Beautif...	4 beds \| 2 baths \| 1,878 sq.ft.	$433,750	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.25% Airbnb Rental Income: $3461 Traditional Rental Income: $2229 Airbnb ROI: 4.4% Traditional ROI: 3.25%
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.	$975,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 1.22% Airbnb Rental Income: $2478 Traditional Rental Income: $2807 Airbnb ROI: 0.19% Traditional ROI: 1.22%
2879 CREEK Street MIDDLEBURG, FL Fantastic investment or vacation home opportunity! This 2BD/2BA stilt home sits on a navig...	2 beds \| 2 baths \| 1,178 sq.ft.	$230,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 6.17% Airbnb Rental Income: $848 Traditional Rental Income: $1846 Airbnb ROI: 0.06% Traditional ROI: 6.17%
2925 COLLEGE PARK Drive MIDDLEBURG, FL Welcome to 2925 College Park Drive. This 3 bedroom, 2 bath home offers 1,412 square feet w...	3 beds \| 2 baths \| 1,412 sq.ft.	$269,900	Airbnb cash on cash: 5.21% Traditional cash on cash: 5.44% Airbnb Rental Income: $2478 Traditional Rental Income: $1936 Airbnb ROI: 5.21% Traditional ROI: 5.44%
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: 3.32% Traditional cash on cash: 8.25% Airbnb Rental Income: $2478 Traditional Rental Income: $3512 Airbnb ROI: 3.32% Traditional ROI: 8.25%
747 SUNNY STROLL Drive MIDDLEBURG, FL New Price!! Your new home awaits in the beautiful neighborhood of Kindle Wood. This bright...	4 beds \| 3 baths \| 2,477 sq.ft.	$359,900	Airbnb cash on cash: 5.24% Traditional cash on cash: 5.92% Airbnb Rental Income: $3461 Traditional Rental Income: $2925 Airbnb ROI: 5.24% Traditional ROI: 5.92%
3073 ZEYNO Drive MIDDLEBURG, FL Vacant and completely move-in ready! This 1,550 sq ft Clay County townhome features 3 bedr...	3 beds \| 3 baths \| 1,550 sq.ft.	$265,000	Airbnb cash on cash: 4.64% Traditional cash on cash: 4.72% Airbnb Rental Income: $2478 Traditional Rental Income: $1896 Airbnb ROI: 4.64% Traditional ROI: 4.72%
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.	$310,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 4.3% Airbnb Rental Income: $2478 Traditional Rental Income: $2049 Airbnb ROI: 3.71% Traditional ROI: 4.3%
3087 S DEER Avenue MIDDLEBURG, FL OPEN HOUSE Cancelled! Charming cottage-style home featuring 3 bedrooms and 2 bathrooms, si...	3 beds \| 2 baths \| 1,440 sq.ft.	$365,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 3.1% Airbnb Rental Income: $2478 Traditional Rental Income: $1903 Airbnb ROI: 3.02% Traditional ROI: 3.1%
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.	$499,999	Airbnb cash on cash: 4.49% Traditional cash on cash: 4.39% Airbnb Rental Income: $3461 Traditional Rental Income: $2647 Airbnb ROI: 4.49% Traditional ROI: 4.39%
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.	$330,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 4.18% Airbnb Rental Income: $2478 Traditional Rental Income: $2074 Airbnb ROI: 3.55% Traditional ROI: 4.18%
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: 4.37% Traditional cash on cash: 5.42% Airbnb Rental Income: $2478 Traditional Rental Income: $2148 Airbnb ROI: 4.37% Traditional ROI: 5.42%
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: 4.3% Traditional cash on cash: 7.46% Airbnb Rental Income: $3461 Traditional Rental Income: $3869 Airbnb ROI: 4.3% Traditional ROI: 7.46%

Real Estate investment in Middleburg, FL

There are 213 properties for sale in the city of Middleburg . The median list price in Middleburg is $399,735 and the average price per square foot is $209. In October 2026, the average monthly cash on cash return in Middleburg is 5.00%. The average monthly rental income in Middleburg is $2,125.

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

There are 213 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 $2,125.

Your search for investment property begins and ends here

Investment Property for Sale in Middleburg, FL

3684 MAIN Street

MIDDLEBURG, FL

3 beds | 3 baths | 2,012 sq.ft.

$700,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $2478

Traditional Rental Income: $2741

Airbnb ROI: 0.74%

Traditional ROI: 2.07%

191 MIMOSA Avenue N

MIDDLEBURG, FL

3 beds | 2 baths | 1,092 sq.ft.

$234,900

Airbnb cash on cash: 5.69%

Traditional cash on cash: 4.22%

Airbnb Rental Income: $2478

Traditional Rental Income: $1549

Airbnb ROI: 5.69%

Traditional ROI: 4.22%

2482 GLOW WOOD Court

MIDDLEBURG, FL

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

$425,000

Airbnb cash on cash: 3.24%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $2478

Traditional Rental Income: $1919

Airbnb ROI: 3.24%

Traditional ROI: 3.35%

3201 FIRESIDE Drive

MIDDLEBURG, FL

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

$369,000

Airbnb cash on cash: 2.65%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $2478

Traditional Rental Income: $2047

Airbnb ROI: 2.65%

Traditional ROI: 3.14%

721 TARA FARMS Drive

MIDDLEBURG, FL

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

$445,000

Airbnb cash on cash: 3.24%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $3461

Traditional Rental Income: $2405

Airbnb ROI: 3.24%

Traditional ROI: 2.55%

1717 LANDWARD Lane

MIDDLEBURG, FL

4 beds | 3 baths | 2,575 sq.ft.

$1,075,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $3461

Traditional Rental Income: $2219

Airbnb ROI: 0.98%

Traditional ROI: 0.5%

3011 ANGORA BAY Drive

MIDDLEBURG, FL

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

$359,900

Airbnb cash on cash: 5.71%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $3461

Traditional Rental Income: $2275

Airbnb ROI: 5.71%

Traditional ROI: 4.47%

2882 TUSCARORA Trail

MIDDLEBURG, FL

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

$310,000

Airbnb cash on cash: 6.51%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $3461

Traditional Rental Income: $2216

Airbnb ROI: 6.51%