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
7281 CACTUS CUT Court MIDDLEBURG, FL Don't miss the 'Virtual Walk Thru' - Click on 'Photos' then 'Virtual Tours' Your Middleb...	3 beds \| 2 baths \| 1,895 sq.ft.	$525,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 3.5% Airbnb Rental Income: $984 Traditional Rental Income: $2514 Airbnb ROI: -0.34% Traditional ROI: 3.5%
4526 SONG SPARROW Drive MIDDLEBURG, FL Immaculate waterfront home in Two Creeks! This 3-bed, 2 bath home features a versatile fle...	3 beds \| 2 baths \| 2,224 sq.ft.	$382,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 4.33% Airbnb Rental Income: $984 Traditional Rental Income: $2551 Airbnb ROI: -1.03% Traditional ROI: 4.33%
3975 CHIMNEY SWIFTS Lane MIDDLEBURG, FL Impeccably maintained 3-bedroom, 2-bathroom single-story residence nestled in the highly s...	3 beds \| 2 baths \| 1,535 sq.ft.	$295,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 4.92% Airbnb Rental Income: $984 Traditional Rental Income: $2208 Airbnb ROI: -0.76% Traditional ROI: 4.92%
4008 CORMORANT Lane MIDDLEBURG, FL Welcome to this spacious, well-maintained home featuring open-concept living and a large, ...	4 beds \| 4 baths \| 2,907 sq.ft.	$400,000	Airbnb cash on cash: 9.34% Traditional cash on cash: 8.52% Airbnb Rental Income: $5300 Traditional Rental Income: $3919 Airbnb ROI: 9.34% Traditional ROI: 8.52%
2016 GLITTER Court MIDDLEBURG, FL This beautiful all brick home is in the gated neighborhood of The Villages of Fireside. Th...	4 beds \| 3 baths \| 2,322 sq.ft.	$440,000	Airbnb cash on cash: 8.08% Traditional cash on cash: 5.17% Airbnb Rental Income: $5300 Traditional Rental Income: $3031 Airbnb ROI: 8.08% Traditional ROI: 5.17%
1871 WOODRIDGE Court MIDDLEBURG, FL This spacious home is tucked away on a quiet cul-de-sac. The 2.6-acre lot offers comfort, ...	3 beds \| 2 baths \| 2,180 sq.ft.	$385,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 4.52% Airbnb Rental Income: $984 Traditional Rental Income: $2411 Airbnb ROI: -0.41% Traditional ROI: 4.52%
1869 LAGO DEL SUR Drive MIDDLEBURG, FL Help the nieghbors hate me This is a give away price Wow! add some paint/flooring few upda...	2 beds \| 2 baths \| 1,152 sq.ft.	$159,900	Airbnb cash on cash: -1.1% Traditional cash on cash: 9.31% Airbnb Rental Income: $634 Traditional Rental Income: $1930 Airbnb ROI: -1.1% Traditional ROI: 9.31%
2050 LAUREL Drive MIDDLEBURG, FL Welcome to a property where country charm meets modern luxury. Nestled on almost 4 acres, ...	3 beds \| 3 baths \| 1,816 sq.ft.	$700,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 2.33% Airbnb Rental Income: $984 Traditional Rental Income: $2688 Airbnb ROI: -0.82% Traditional ROI: 2.33%
1407 HEATHER GLEN Lane MIDDLEBURG, FL Welcome home to this 3 bedroom, 2 bathroom property tucked into a quiet cul-de-sac in soug...	3 beds \| 2 baths \| 1,783 sq.ft.	$300,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 4.11% Airbnb Rental Income: $984 Traditional Rental Income: $1962 Airbnb ROI: -0.6% Traditional ROI: 4.11%
4781 GOPHER Circle MIDDLEBURG, FL Live Your Best Life at 4781 Gopher Circle, Middleburg - A Country Retreat with Endless Pos...	4 beds \| 2 baths \| 2,232 sq.ft.	$500,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 2.5% Airbnb Rental Income: $5300 Traditional Rental Income: $2237 Airbnb ROI: 6.76% Traditional ROI: 2.5%
3938 SUNSET SKY Road MIDDLEBURG, FL Welcome to your new home that feels like a vacation retreat! This charming log cabin will ...	3 beds \| 2 baths \| 2,056 sq.ft.	$1,050,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.88% Airbnb Rental Income: $984 Traditional Rental Income: $2603 Airbnb ROI: -1.13% Traditional ROI: 0.88%
1998 LENOX Court MIDDLEBURG, FL Welcome Home! This gorgeous home a brand-new: Kitchen, Stainless Steel Appliances, Oven, R...	3 beds \| 2 baths \| 2,152 sq.ft.	$379,900	Airbnb cash on cash: -0.47% Traditional cash on cash: 3.27% Airbnb Rental Income: $984 Traditional Rental Income: $1961 Airbnb ROI: -0.47% Traditional ROI: 3.27%
2016 AMBERLY Drive MIDDLEBURG, FL **Back on Market - No Fault of Sellers. Motivated Sellers - Ready for New Offers AND Selle...	3 beds \| 2 baths \| 2,425 sq.ft.	$349,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 4.67% Airbnb Rental Income: $984 Traditional Rental Income: $2713 Airbnb ROI: -1.68% Traditional ROI: 4.67%
4162 SCENIC Drive MIDDLEBURG, FL Welcome to your dream retreat! Nestled along the serene banks of Black Creek, this stunnin...	2 beds \| 2 baths \| 1,320 sq.ft.	$359,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 2.37% Airbnb Rental Income: $634 Traditional Rental Income: $1494 Airbnb ROI: -1.06% Traditional ROI: 2.37%
1011 WETLAND RIDGE Circle MIDDLEBURG, FL *BACK ON MARKET AT NO FAULT OF SELLERS. Buyers - you now have a 2nd chance to own this bea...	3 beds \| 2 baths \| 2,297 sq.ft.	$340,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 5.95% Airbnb Rental Income: $984 Traditional Rental Income: $2603 Airbnb ROI: -0.22% Traditional ROI: 5.95%
4410 TARRAGON Avenue MIDDLEBURG, FL Assumable VA Loan. Discover your perfect retreat on just over 1 acre in a peaceful, open-s...	4 beds \| 3 baths \| 2,403 sq.ft.	$539,900	Airbnb cash on cash: 6.14% Traditional cash on cash: 3.38% Airbnb Rental Income: $5300 Traditional Rental Income: $2836 Airbnb ROI: 6.14% Traditional ROI: 3.38%
1854 QUEBEC Court MIDDLEBURG, FL Charming 2 Bedroom, 2 Bathroom Home in Growing Middleburg, Florida! This beautifully maint...	2 beds \| 2 baths \| 1,072 sq.ft.	$227,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 4.03% Airbnb Rental Income: $634 Traditional Rental Income: $1491 Airbnb ROI: -1.33% Traditional ROI: 4.03%
2819 BLACK CREEK Drive MIDDLEBURG, FL Come set up your dream estate or build a family compound on this beautiful property. Clay ...	2 beds \| 3 baths \| 2,228 sq.ft.	$3,900,000	Airbnb cash on cash: -1.82% Traditional cash on cash: -1.2% Airbnb Rental Income: $634 Traditional Rental Income: $2556 Airbnb ROI: -1.82% Traditional ROI: -1.2%
4340 LAZY H RANCH Road MIDDLEBURG, FL Come set up your dream estate or build a family compound on this beautiful property. Clay ...	2 beds \| 3 baths \| 2,228 sq.ft.	$2,000,000	Airbnb cash on cash: -1.75% Traditional cash on cash: -0.56% Airbnb Rental Income: $634 Traditional Rental Income: $2556 Airbnb ROI: -1.75% Traditional ROI: -0.56%
3954 TRAIL RIDGE Road MIDDLEBURG, FL SELLERS OFFERING $2500 TO BUYER AT CLOSING!! Welcome to 3954 Trail Ridge Rd, a charming si...	3 beds \| 2 baths \| 1,739 sq.ft.	$339,900	Airbnb cash on cash: -1.34% Traditional cash on cash: 2.9% Airbnb Rental Income: $984 Traditional Rental Income: $1985 Airbnb ROI: -1.34% Traditional ROI: 2.9%
47 HORSETAIL Avenue MIDDLEBURG, FL Dreaming of country living without HOA restrictions? This beautifully maintained 3-bedroom...	3 beds \| 2 baths \| 1,633 sq.ft.	$385,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.93% Airbnb Rental Income: $984 Traditional Rental Income: $1952 Airbnb ROI: -0.72% Traditional ROI: 2.93%
2482 ALOHA Lane MIDDLEBURG, FL Nestled in one of Middleburg's most desirable neighborhoods, this charming home offers the...	3 beds \| 2 baths \| 1,330 sq.ft.	$294,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.38% Airbnb Rental Income: $984 Traditional Rental Income: $1832 Airbnb ROI: 0.05% Traditional ROI: 4.38%
5239 PEGGY Lane MIDDLEBURG, FL Welcome to 5239 Peggy Lane a charming brick home tucked away on a peaceful, private one-ac...	3 beds \| 2 baths \| 2,065 sq.ft.	$449,999	Airbnb cash on cash: -0.59% Traditional cash on cash: 3.65% Airbnb Rental Income: $984 Traditional Rental Income: $2419 Airbnb ROI: -0.59% Traditional ROI: 3.65%
1840 YUKON Court MIDDLEBURG, FL Welcome Home! This adorable 3-bedroom, 2-bathroom home offers so much potential. Open floo...	3 beds \| 2 baths \| 1,272 sq.ft.	$244,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 4.85% Airbnb Rental Income: $984 Traditional Rental Income: $1746 Airbnb ROI: 0.02% Traditional ROI: 4.85%
2634 PINEWOOD Boulevard MIDDLEBURG, FL Location, Location, Location! This lovely well maintained home is located in the back of t...	3 beds \| 2 baths \| 1,252 sq.ft.	$287,500	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.54% Airbnb Rental Income: $984 Traditional Rental Income: $1625 Airbnb ROI: -0.13% Traditional ROI: 3.54%
3557 GRAYSON Lane MIDDLEBURG, FL No CDD fee! This charming home is located in the desirable Cameron Oaks community and offe...	4 beds \| N/A baths \| 2,213 sq.ft.	$369,000	Airbnb cash on cash: 9.46% Traditional cash on cash: 4.95% Airbnb Rental Income: $5300 Traditional Rental Income: $2664 Airbnb ROI: 9.46% Traditional ROI: 4.95%
3251 LOBLOLLY PINE Court MIDDLEBURG, FL Discover easy, one-level living in this beautifully maintained 3-bedroom, 2-bath ranch off...	3 beds \| 2 baths \| 1,507 sq.ft.	$295,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 4.22% Airbnb Rental Income: $984 Traditional Rental Income: $2016 Airbnb ROI: -0.77% Traditional ROI: 4.22%
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: 0.8% Airbnb Rental Income: $634 Traditional Rental Income: $1683 Airbnb ROI: -1% Traditional ROI: 0.8%
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.	$320,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 3.71% Airbnb Rental Income: $984 Traditional Rental Income: $1973 Airbnb ROI: -0.75% Traditional ROI: 3.71%
2704 TINA Lane MIDDLEBURG, FL Welcome to this charming 3-bedroom, 2-bathroom brick home in the sought-after Evergreen co...	3 beds \| 2 baths \| 1,084 sq.ft.	$245,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.33% Airbnb Rental Income: $984 Traditional Rental Income: $1588 Airbnb ROI: 0.2% Traditional ROI: 4.33%
1124 PERSIMMON Drive MIDDLEBURG, FL Welcome to this stunning former model home built in 2019! Discover 3 bedrooms, 2 bathrooms...	3 beds \| 2 baths \| 1,867 sq.ft.	$349,900	Airbnb cash on cash: -1.41% Traditional cash on cash: 2.86% Airbnb Rental Income: $984 Traditional Rental Income: $2036 Airbnb ROI: -1.41% Traditional ROI: 2.86%
1651 SEDGWICK Drive MIDDLEBURG, FL Welcome to your new retreat! This spacious 3-bedroom, 2-bath home sits on a serene half-ac...	3 beds \| 2 baths \| 1,968 sq.ft.	$429,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.57% Airbnb Rental Income: $984 Traditional Rental Income: $1974 Airbnb ROI: -0.77% Traditional ROI: 2.57%
3001 NAUTILUS Road MIDDLEBURG, FL Beautiful Luxury Brick Home in Prime Location! This 4-bedroom, 2-bath home features carpet...	4 beds \| 2 baths \| 2,913 sq.ft.	$469,000	Airbnb cash on cash: 7.55% Traditional cash on cash: 3.32% Airbnb Rental Income: $5300 Traditional Rental Income: $2374 Airbnb ROI: 7.55% Traditional ROI: 3.32%
1828 AMBERLY Drive MIDDLEBURG, FL Price recently reduced! Welcome to 1828 Amberly Drive-a stunning 4BR/3BA + loft home with ...	4 beds \| 3 baths \| 2,381 sq.ft.	$440,000	Airbnb cash on cash: 7.78% Traditional cash on cash: 4.71% Airbnb Rental Income: $5300 Traditional Rental Income: $2963 Airbnb ROI: 7.78% Traditional ROI: 4.71%
3409 STEELGATE Court MIDDLEBURG, FL Seller is looking ay ALL REASONABLE OFFERS, and is offering a 2/1 buy down on the mortgage...	3 beds \| 2 baths \| 2,198 sq.ft.	$365,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.92% Airbnb Rental Income: $984 Traditional Rental Income: $2247 Airbnb ROI: -0.79% Traditional ROI: 3.92%
4110 SCENIC Drive MIDDLEBURG, FL Stunning Black Creek Waterfront Paradise Discover your dream home on the water with this o...	4 beds \| 3 baths \| 2,305 sq.ft.	$784,900	Airbnb cash on cash: 4.43% Traditional cash on cash: 2.27% Airbnb Rental Income: $5300 Traditional Rental Income: $2647 Airbnb ROI: 4.43% Traditional ROI: 2.27%
2968 RAVINE HILL Drive MIDDLEBURG, FL Welcome to your beautiful home. The curb appeal will draw you in and you will not be disap...	3 beds \| N/A baths \| 1,963 sq.ft.	$359,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 4.95% Airbnb Rental Income: $984 Traditional Rental Income: $2384 Airbnb ROI: -0.24% Traditional ROI: 4.95%
3770 CREEK HOLLOW Lane MIDDLEBURG, FL Tucked away in the peaceful, tree-lined community of The Ravines, known for its custom hom...	4 beds \| 2 baths \| 2,856 sq.ft.	$425,000	Airbnb cash on cash: 8.29% Traditional cash on cash: 5.46% Airbnb Rental Income: $5300 Traditional Rental Income: $3103 Airbnb ROI: 8.29% Traditional ROI: 5.46%
3164 RAVINES Road MIDDLEBURG, FL Your Perfect Blend of Luxury & Convenience Awaits! Step into this beautifully updated two-...	3 beds \| 3 baths \| 2,134 sq.ft.	$295,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 5.93% Airbnb Rental Income: $984 Traditional Rental Income: $2450 Airbnb ROI: -0.62% Traditional ROI: 5.93%
2705 PINEWOOD Boulevard N MIDDLEBURG, FL Charming 3-bedroom, 2-bath brick home with 1,262 square feet of living space, built in 198...	3 beds \| 2 baths \| 1,262 sq.ft.	$237,500	Airbnb cash on cash: 0.01% Traditional cash on cash: 5.11% Airbnb Rental Income: $984 Traditional Rental Income: $1776 Airbnb ROI: 0.01% Traditional ROI: 5.11%

Real Estate investment in Middleburg, FL

There are 112 properties for sale in the city of Middleburg . The median list price in Middleburg is $355,000 and the average price per square foot is $180. In November 2025, the average monthly cash on cash return in Middleburg is 4.00%. The average monthly rental income in Middleburg is $2,126.

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

There are 112 investment properties available for sale in Middleburg.

In 2025, the best neighborhood to buy investment property is MIDDLEBURG.

The ROI for Short-Term is higher than the Long-Term in Middleburg with average rental income of $984.

Your search for investment property begins and ends here

Investment Property for Sale in Middleburg, FL

7281 CACTUS CUT Court

MIDDLEBURG, FL

3 beds | 2 baths | 1,895 sq.ft.

$525,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $984

Traditional Rental Income: $2514

Airbnb ROI: -0.34%

Traditional ROI: 3.5%

4526 SONG SPARROW Drive

MIDDLEBURG, FL

3 beds | 2 baths | 2,224 sq.ft.

$382,000

Airbnb cash on cash: -1.03%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $984

Traditional Rental Income: $2551

Airbnb ROI: -1.03%

Traditional ROI: 4.33%

3975 CHIMNEY SWIFTS Lane

MIDDLEBURG, FL

3 beds | 2 baths | 1,535 sq.ft.

$295,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: 4.92%

Airbnb Rental Income: $984

Traditional Rental Income: $2208

Airbnb ROI: -0.76%

Traditional ROI: 4.92%

4008 CORMORANT Lane

MIDDLEBURG, FL

4 beds | 4 baths | 2,907 sq.ft.

$400,000

Airbnb cash on cash: 9.34%

Traditional cash on cash: 8.52%

Airbnb Rental Income: $5300

Traditional Rental Income: $3919

Airbnb ROI: 9.34%

Traditional ROI: 8.52%

2016 GLITTER Court

MIDDLEBURG, FL

4 beds | 3 baths | 2,322 sq.ft.

$440,000

Airbnb cash on cash: 8.08%

Traditional cash on cash: 5.17%

Airbnb Rental Income: $5300

Traditional Rental Income: $3031

Airbnb ROI: 8.08%

Traditional ROI: 5.17%

1871 WOODRIDGE Court

MIDDLEBURG, FL

3 beds | 2 baths | 2,180 sq.ft.

$385,000

Airbnb cash on cash: -0.41%

Traditional cash on cash: 4.52%

Airbnb Rental Income: $984

Traditional Rental Income: $2411

Airbnb ROI: -0.41%

Traditional ROI: 4.52%

1869 LAGO DEL SUR Drive

MIDDLEBURG, FL

2 beds | 2 baths | 1,152 sq.ft.

$159,900

Airbnb cash on cash: -1.1%

Traditional cash on cash: 9.31%

Airbnb Rental Income: $634

Traditional Rental Income: $1930

Airbnb ROI: -1.1%

Traditional ROI: 9.31%

2050 LAUREL Drive

MIDDLEBURG, FL

3 beds | 3 baths | 1,816 sq.ft.

$700,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 2.33%

Airbnb Rental Income: $984

Traditional Rental Income: $2688

Airbnb ROI: -0.82%