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 *OPEN HOUSE - SEP 20TH 10AM-NOON* *Don't miss the 'Virtual Walk Thru' - Click on 'Phot...	3 beds \| 2 baths \| 1,895 sq.ft.	$550,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 3.3% Airbnb Rental Income: $2436 Traditional Rental Income: $2514 Airbnb ROI: 1.99% Traditional ROI: 3.3%
3718 ICENI Court MIDDLEBURG, FL Certified Fresh and Move-In Ready! Welcome to Coppergate and this beautifully maintained ,...	4 beds \| 2 baths \| 1,878 sq.ft.	$330,000	Airbnb cash on cash: 7.66% Traditional cash on cash: 5.09% Airbnb Rental Income: $3776 Traditional Rental Income: $2163 Airbnb ROI: 7.66% Traditional ROI: 5.09%
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: 3.6% Traditional cash on cash: 4.92% Airbnb Rental Income: $2436 Traditional Rental Income: $2208 Airbnb ROI: 3.6% Traditional ROI: 4.92%
1891 HUNTERS TRACE Circle MIDDLEBURG, FL Charming 3 Bedroom Home in Middleburg located on a Cul-de-Sac. Welcome to this well-mainta...	3 beds \| 2 baths \| 1,235 sq.ft.	$239,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.58% Airbnb Rental Income: $2436 Traditional Rental Income: $1680 Airbnb ROI: 5.3% Traditional ROI: 4.58%
4780 GOPHER Circle MIDDLEBURG, FL Welcome to this well-maintained 3-bedroom, 2-bath brick-front home on 1.25 acres in up and...	3 beds \| 2 baths \| 1,800 sq.ft.	$445,850	Airbnb cash on cash: 2.3% Traditional cash on cash: 3.11% Airbnb Rental Income: $2436 Traditional Rental Income: $2176 Airbnb ROI: 2.3% Traditional ROI: 3.11%
4008 CORMORANT Lane MIDDLEBURG, FL Seller to offer 10k towards buyer's closing cost, pre-paids or rate buydown. Welcome to th...	4 beds \| 4 baths \| 2,907 sq.ft.	$410,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 8.29% Airbnb Rental Income: $3776 Traditional Rental Income: $3919 Airbnb ROI: 5.79% Traditional ROI: 8.29%
1798 LAKEDGE Drive MIDDLEBURG, FL Discover the perfect blend of luxury, privacy, and waterfront living at 1798 Lakedge Dr-a ...	5 beds \| 3 baths \| 3,398 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.11% Airbnb Rental Income: $null Traditional Rental Income: $4100 Airbnb ROI: N/A Traditional ROI: 2.11%
2361 SANDY RUN Drive N MIDDLEBURG, FL Experience the ultimate Black Creek lifestyle with this beautifully remodeled 4-bedroom, 3...	4 beds \| 3 baths \| 2,281 sq.ft.	$650,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 3.31% Airbnb Rental Income: $3776 Traditional Rental Income: $3119 Airbnb ROI: 3.04% Traditional ROI: 3.31%
4296 GREAT EGRET Way MIDDLEBURG, FL This spacious single-story 4-bedroom, 3-bath home features new carpet and fresh paint thro...	4 beds \| 3 baths \| 3,184 sq.ft.	$489,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 4.01% Airbnb Rental Income: $3776 Traditional Rental Income: $3059 Airbnb ROI: 3.79% Traditional ROI: 4.01%
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.	$750,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 2.11% Airbnb Rental Income: $2436 Traditional Rental Income: $2688 Airbnb ROI: 0.9% Traditional ROI: 2.11%
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: 4.04% Traditional cash on cash: 2.5% Airbnb Rental Income: $3776 Traditional Rental Income: $2237 Airbnb ROI: 4.04% Traditional ROI: 2.5%
4299 HAWK HAVEN Road MIDDLEBURG, FL Escape to your own private retreat on over 8+ acres along the scenic and navigable Black C...	4 beds \| 3 baths \| 2,204 sq.ft.	$1,200,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 1.6% Airbnb Rental Income: $3776 Traditional Rental Income: $3435 Airbnb ROI: 1.17% Traditional ROI: 1.6%
2038 CREEKMONT Drive MIDDLEBURG, FL Welcome to Doctors Inlet Reserve where comfort, convenience, and space come together. This...	5 beds \| 3 baths \| 2,900 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $2873 Airbnb ROI: N/A Traditional ROI: 4.66%
4916 CREEK BLUFF Lane MIDDLEBURG, FL DON'T LET THIS OPPORTUNITY PASS YOU BY!! $10,000 PRICE REDUCTION MUST SELL! Welcome Ho...	3 beds \| 2 baths \| 2,119 sq.ft.	$325,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 3.69% Airbnb Rental Income: $2436 Traditional Rental Income: $2174 Airbnb ROI: 2.6% Traditional ROI: 3.69%
1094 PERSIMMON Drive MIDDLEBURG, FL $4,500 LENDER CREDIT WITH PREFERRED LENDER AND PRE APPROVAL! Stunning 3-Bedroom Home with ...	3 beds \| 3 baths \| 1,877 sq.ft.	$339,900	Airbnb cash on cash: 2.38% Traditional cash on cash: 3.85% Airbnb Rental Income: $2436 Traditional Rental Income: $2312 Airbnb ROI: 2.38% Traditional ROI: 3.85%
4409 SONG SPARROW Drive MIDDLEBURG, FL CDD BOND IS PAID!!! Welcome to this beautifully home nestled in the highly desirable Two C...	4 beds \| 2 baths \| 2,002 sq.ft.	$349,900	Airbnb cash on cash: 5.94% Traditional cash on cash: 3.98% Airbnb Rental Income: $3776 Traditional Rental Income: $2312 Airbnb ROI: 5.94% Traditional ROI: 3.98%
4328 ROCK PIGEON LANE MIDDLEBURG, FL Under contract-accepting backup offers. Exclusive Lakefront Home in The Preserve at Two Cr...	5 beds \| 3 baths \| 3,071 sq.ft.	$568,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $2981 Airbnb ROI: N/A Traditional ROI: 2.8%
5566 OREGON Trail MIDDLEBURG, FL If you are looking for country living, pack your bags and slip away to this retreat! This ...	3 beds \| 2 baths \| 1,776 sq.ft.	$269,999	Airbnb cash on cash: 5.28% Traditional cash on cash: 6.15% Airbnb Rental Income: $2436 Traditional Rental Income: $2064 Airbnb ROI: 5.28% Traditional ROI: 6.15%
1479 KING RAIL Lane MIDDLEBURG, FL Looking for value? Welcome to this expansive, move-in-ready home in the sought-after Two C...	4 beds \| 4 baths \| 2,942 sq.ft.	$395,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 3.42% Airbnb Rental Income: $3776 Traditional Rental Income: $2573 Airbnb ROI: 4.46% Traditional ROI: 3.42%
2064 FROGMORE Drive MIDDLEBURG, FL Welcome to 2064 Frogmore Dr-a beautifully maintained home in the heart of Middleburg! This...	4 beds \| 2 baths \| 1,817 sq.ft.	$314,000	Airbnb cash on cash: 7.73% Traditional cash on cash: 4.92% Airbnb Rental Income: $3776 Traditional Rental Income: $2130 Airbnb ROI: 7.73% Traditional ROI: 4.92%
2016 AMBERLY Drive MIDDLEBURG, FL **Back on Market - No Fault of Sellers. Motivated Sellers - Ready for New Offers!!! Welcom...	3 beds \| 3 baths \| 2,425 sq.ft.	$359,900	Airbnb cash on cash: 1.92% Traditional cash on cash: 4.5% Airbnb Rental Income: $2436 Traditional Rental Income: $2713 Airbnb ROI: 1.92% Traditional ROI: 4.5%
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.	$360,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 2.36% Airbnb Rental Income: $2688 Traditional Rental Income: $1494 Airbnb ROI: 4.01% Traditional ROI: 2.36%
4410 TARRAGON Avenue MIDDLEBURG, FL Discover your perfect retreat on just over 1 acre in a peaceful, open-space neighborhood-n...	4 beds \| 3 baths \| 2,403 sq.ft.	$549,900	Airbnb cash on cash: 3.54% Traditional cash on cash: 3.3% Airbnb Rental Income: $3776 Traditional Rental Income: $2836 Airbnb ROI: 3.54% Traditional ROI: 3.3%
1103 ORCHARD ORIOLE Place MIDDLEBURG, FL VA Loan Assumption available at 2.625%!!! Welcome to luxury living in the highly sought-af...	4 beds \| 3 baths \| 3,062 sq.ft.	$535,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 3.01% Airbnb Rental Income: $3776 Traditional Rental Income: $2938 Airbnb ROI: 3.05% Traditional ROI: 3.01%
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: -1.34% Traditional cash on cash: -1.2% Airbnb Rental Income: $2688 Traditional Rental Income: $2556 Airbnb ROI: -1.34% Traditional ROI: -1.2%
5493 KNOB HILL MIDDLEBURG, FL Welcome home! We are proud to Introduce a beautifully updated country ranch home nestled o...	4 beds \| 2 baths \| 1,448 sq.ft.	$271,000	Airbnb cash on cash: 9.57% Traditional cash on cash: 5.48% Airbnb Rental Income: $3776 Traditional Rental Income: $1912 Airbnb ROI: 9.57% Traditional ROI: 5.48%
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: -0.83% Traditional cash on cash: -0.56% Airbnb Rental Income: $2688 Traditional Rental Income: $2556 Airbnb ROI: -0.83% 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: 2.45% Traditional cash on cash: 2.9% Airbnb Rental Income: $2436 Traditional Rental Income: $1985 Airbnb ROI: 2.45% Traditional ROI: 2.9%
5239 PEGGY Lane MIDDLEBURG, FL This charming brick home is situated on a peaceful, private one-acre lot in the heart of C...	3 beds \| 2 baths \| 2,065 sq.ft.	$485,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 3.32% Airbnb Rental Income: $2436 Traditional Rental Income: $2419 Airbnb ROI: 2.04% Traditional ROI: 3.32%
133 KNIGHT BOXX Road MIDDLEBURG, FL Attention Investors!! Motivated seller!! Assume this RATE at 5.75% Or even OWNER FINANCE!!...	3 beds \| 2 baths \| 1,446 sq.ft.	$310,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 3.68% Airbnb Rental Income: $2436 Traditional Rental Income: $1798 Airbnb ROI: 3.83% Traditional ROI: 3.68%
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: 5.26% Traditional cash on cash: 4.85% Airbnb Rental Income: $2436 Traditional Rental Income: $1746 Airbnb ROI: 5.26% Traditional ROI: 4.85%
1977 AMBERLY Drive MIDDLEBURG, FL This stunning 3 bedroom, 2.5 bath home with a bonus room was built in 2021 and shows like ...	3 beds \| 3 baths \| 2,384 sq.ft.	$369,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 4.18% Airbnb Rental Income: $2436 Traditional Rental Income: $2672 Airbnb ROI: 1.78% Traditional ROI: 4.18%
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.	$290,000	Airbnb cash on cash: 4.29% Traditional cash on cash: 3.5% Airbnb Rental Income: $2436 Traditional Rental Income: $1625 Airbnb ROI: 4.29% Traditional ROI: 3.5%
3840 GREAT FALLS LOOP MIDDLEBURG, FL Former DR Horton model home in Azalea Ridge! This spacious, 4bed/2bath home has all the up...	4 beds \| 2 baths \| 2,282 sq.ft.	$367,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 4.5% Airbnb Rental Income: $3776 Traditional Rental Income: $2422 Airbnb ROI: 6.05% Traditional ROI: 4.5%
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: 1.29% Traditional cash on cash: 0.8% Airbnb Rental Income: $2688 Traditional Rental Income: $1683 Airbnb ROI: 1.29% Traditional ROI: 0.8%
3973 HEATHERBROOK Place MIDDLEBURG, FL ONE OF THE BEST PRICE PER SQFT IN THE OAKLEAF AREA - LAKE LOT! This home qualifies for up ...	3 beds \| 3 baths \| 2,206 sq.ft.	$359,900	Airbnb cash on cash: 1.89% Traditional cash on cash: 2.91% Airbnb Rental Income: $2436 Traditional Rental Income: $2185 Airbnb ROI: 1.89% Traditional ROI: 2.91%
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: 5.42% Traditional cash on cash: 4.33% Airbnb Rental Income: $2436 Traditional Rental Income: $1588 Airbnb ROI: 5.42% 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: 2.27% Traditional cash on cash: 2.86% Airbnb Rental Income: $2436 Traditional Rental Income: $2036 Airbnb ROI: 2.27% 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.	$439,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 2.49% Airbnb Rental Income: $2436 Traditional Rental Income: $1974 Airbnb ROI: 2.16% Traditional ROI: 2.49%
3691 EAGLE ROCK Road MIDDLEBURG, FL Experience the ultimate in luxury and modern comfort with this stunning 3-bedroom, 2.5-bat...	3 beds \| 3 baths \| 2,408 sq.ft.	$487,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 3.47% Airbnb Rental Income: $2436 Traditional Rental Income: $2479 Airbnb ROI: 2.07% Traditional ROI: 3.47%

Real Estate investment in Middleburg, FL

There are 165 properties for sale in the city of Middleburg . The median list price in Middleburg is $359,900 and the average price per square foot is $176. In September 2025, the average monthly cash on cash return in Middleburg is 4.00%. The average monthly rental income in Middleburg is $2,187.

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

There are 165 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 $2,436.

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.

$550,000

Airbnb cash on cash: 1.99%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $2436

Traditional Rental Income: $2514

Airbnb ROI: 1.99%

Traditional ROI: 3.3%

3718 ICENI Court

MIDDLEBURG, FL

4 beds | 2 baths | 1,878 sq.ft.

$330,000

Airbnb cash on cash: 7.66%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $3776

Traditional Rental Income: $2163

Airbnb ROI: 7.66%

Traditional ROI: 5.09%

3975 CHIMNEY SWIFTS Lane

MIDDLEBURG, FL

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

$295,000

Airbnb cash on cash: 3.6%

Traditional cash on cash: 4.92%

Airbnb Rental Income: $2436

Traditional Rental Income: $2208

Airbnb ROI: 3.6%

Traditional ROI: 4.92%

1891 HUNTERS TRACE Circle

MIDDLEBURG, FL

3 beds | 2 baths | 1,235 sq.ft.

$239,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $2436

Traditional Rental Income: $1680

Airbnb ROI: 5.3%

Traditional ROI: 4.58%

4780 GOPHER Circle

MIDDLEBURG, FL

3 beds | 2 baths | 1,800 sq.ft.

$445,850

Airbnb cash on cash: 2.3%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $2436

Traditional Rental Income: $2176

Airbnb ROI: 2.3%

Traditional ROI: 3.11%

4008 CORMORANT Lane

MIDDLEBURG, FL

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

$410,000

Airbnb cash on cash: 5.79%

Traditional cash on cash: 8.29%

Airbnb Rental Income: $3776

Traditional Rental Income: $3919

Airbnb ROI: 5.79%

Traditional ROI: 8.29%

1798 LAKEDGE Drive

MIDDLEBURG, FL

5 beds | 3 baths | 3,398 sq.ft.

$1,150,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.11%

Airbnb Rental Income: $null

Traditional Rental Income: $4100

Airbnb ROI: N/A

Traditional ROI: 2.11%

2361 SANDY RUN Drive N

MIDDLEBURG, FL

4 beds | 3 baths | 2,281 sq.ft.

$650,000

Airbnb cash on cash: 3.04%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $3776

Traditional Rental Income: $3119

Airbnb ROI: 3.04%