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
2030 WAYFARE Lane MIDDLEBURG, FL Discover the perfect blend of space, privacy, and opportunity at 2030 Wayfare Ln. Situated...	4 beds \| 3 baths \| 2,184 sq.ft.	$559,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 3.68% Airbnb Rental Income: $5300 Traditional Rental Income: $2889 Airbnb ROI: 6.24% Traditional ROI: 3.68%
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.	$515,000	Airbnb cash on cash: 7.36% Traditional cash on cash: 9.85% Airbnb Rental Income: $5300 Traditional Rental Income: $5430 Airbnb ROI: 7.36% Traditional ROI: 9.85%
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.	$648,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 1.62% Airbnb Rental Income: $5300 Traditional Rental Income: $2290 Airbnb ROI: 4.83% Traditional ROI: 1.62%
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.	$849,900	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $3937 Airbnb ROI: N/A Traditional ROI: 3%
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: 1.09% Airbnb Rental Income: $984 Traditional Rental Income: $2724 Airbnb ROI: -1.17% Traditional ROI: 1.09%
2415 MOON HARBOR Way MIDDLEBURG, FL POOL HOMECORNER LOTUPGRADED Welcome to this impeccably maintained home, perfectly ...	4 beds \| 2 baths \| 2,303 sq.ft.	$450,000	Airbnb cash on cash: 7.77% Traditional cash on cash: 4.97% Airbnb Rental Income: $5300 Traditional Rental Income: $3046 Airbnb ROI: 7.77% Traditional ROI: 4.97%
2246 BOTANY Street MIDDLEBURG, FL NO CDD and NO HOA! Beautifully renovated ranch home featuring an open floor plan designed ...	3 beds \| 2 baths \| 1,212 sq.ft.	$285,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 5.24% Airbnb Rental Income: $984 Traditional Rental Income: $1976 Airbnb ROI: 0.23% Traditional ROI: 5.24%
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.	$369,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 6.56% Airbnb Rental Income: $984 Traditional Rental Income: $3058 Airbnb ROI: -0.45% Traditional ROI: 6.56%
2372 TIGRESS Lane MIDDLEBURG, FL This 3-bedroom, 2-bath home, located in the established neighborhood of Orange Park South,...	3 beds \| 2 baths \| 1,364 sq.ft.	$282,500	Airbnb cash on cash: -0.36% Traditional cash on cash: 5.54% Airbnb Rental Income: $984 Traditional Rental Income: $2203 Airbnb ROI: -0.36% Traditional ROI: 5.54%
1703 PELICAN Place MIDDLEBURG, FL Assumable VA Loan. Enjoy waterfront living on beautiful Doctors Lake in this fully renovat...	4 beds \| 3 baths \| 2,659 sq.ft.	$1,399,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 1.55% Airbnb Rental Income: $5300 Traditional Rental Income: $4562 Airbnb ROI: 1.29% Traditional ROI: 1.55%
3954 TRAIL RIDGE Road MIDDLEBURG, FL Welcome to 3954 Trail Ridge Rd, a charming single-family home located in the great neighbo...	3 beds \| 2 baths \| 1,739 sq.ft.	$334,900	Airbnb cash on cash: -1.34% Traditional cash on cash: 3.93% Airbnb Rental Income: $984 Traditional Rental Income: $2292 Airbnb ROI: -1.34% Traditional ROI: 3.93%
4015 CORMORANT Lane MIDDLEBURG, FL NEW PRICE! Enjoy resort-style living with poolside vibes, featuring a splash park, fitness...	4 beds \| 3 baths \| 2,663 sq.ft.	$446,999	Airbnb cash on cash: 6.85% Traditional cash on cash: 7.47% Airbnb Rental Income: $5300 Traditional Rental Income: $4490 Airbnb ROI: 6.85% Traditional ROI: 7.47%
3798 BEDFORD Drive MIDDLEBURG, FL Imagine this... you walk through the front door and the home greets you with soaring ceili...	5 beds \| 3 baths \| 2,496 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $2329 Airbnb ROI: N/A Traditional ROI: 4.02%
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: 6.61% Airbnb Rental Income: $984 Traditional Rental Income: $2151 Airbnb ROI: 0.02% Traditional ROI: 6.61%
3083 ZEYNO Drive MIDDLEBURG, FL Don't miss this chance to own a beautifully updated home where listings are rare. This hom...	3 beds \| 3 baths \| 1,889 sq.ft.	$280,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 6.37% Airbnb Rental Income: $984 Traditional Rental Income: $2232 Airbnb ROI: 0.31% Traditional ROI: 6.37%
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.	$270,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 4.69% Airbnb Rental Income: $984 Traditional Rental Income: $2016 Airbnb ROI: -0.75% Traditional ROI: 4.69%
2971 TUSCARORA Trail MIDDLEBURG, FL Welcome to this beautifully maintained home in the desirable community of Ridaught Landing...	4 beds \| 2 baths \| 1,770 sq.ft.	$369,000	Airbnb cash on cash: 9.55% Traditional cash on cash: 4.67% Airbnb Rental Income: $5300 Traditional Rental Income: $2538 Airbnb ROI: 9.55% Traditional ROI: 4.67%
2929 LUCILLE LANE MIDDLEBURG, FL SPRING SPECIAL!! NEW PRICE! All reasonable offers will be considered!! Extraordinary 2-...	3 beds \| 3 baths \| 1,877 sq.ft.	$345,999	Airbnb cash on cash: -0.32% Traditional cash on cash: 4.3% Airbnb Rental Income: $984 Traditional Rental Income: $2133 Airbnb ROI: -0.32% Traditional ROI: 4.3%
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: 1.03% Airbnb Rental Income: $634 Traditional Rental Income: $1855 Airbnb ROI: -1% Traditional ROI: 1.03%
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: 4.2% Airbnb Rental Income: $5300 Traditional Rental Income: $2661 Airbnb ROI: 8.43% Traditional ROI: 4.2%
1841 YUKON Court MIDDLEBURG, FL Short Sale Opportunity with strong upside potential. Located at the end of a quiet dead-en...	3 beds \| 2 baths \| 1,272 sq.ft.	$195,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 6.72% Airbnb Rental Income: $984 Traditional Rental Income: $1811 Airbnb ROI: 0.35% Traditional ROI: 6.72%
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: 6.29% Airbnb Rental Income: $984 Traditional Rental Income: $2613 Airbnb ROI: -0.73% Traditional ROI: 6.29%
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: 5.73% Airbnb Rental Income: $984 Traditional Rental Income: $1912 Airbnb ROI: 0.2% Traditional ROI: 5.73%
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.	$340,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 4.76% Airbnb Rental Income: $984 Traditional Rental Income: $2608 Airbnb ROI: -1.43% Traditional ROI: 4.76%
1651 SEDGWICK Drive MIDDLEBURG, FL This spacious 3-bedroom, 2-bath home sits on a serene half-acre lot at the end of a quiet ...	3 beds \| 2 baths \| 1,968 sq.ft.	$399,500	Airbnb cash on cash: -0.76% Traditional cash on cash: 2.83% Airbnb Rental Income: $984 Traditional Rental Income: $1974 Airbnb ROI: -0.76% Traditional ROI: 2.83%
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.	$444,900	Airbnb cash on cash: 8.01% Traditional cash on cash: 5.27% Airbnb Rental Income: $5300 Traditional Rental Income: $3089 Airbnb ROI: 8.01% Traditional ROI: 5.27%
3139 S DEER Avenue MIDDLEBURG, FL Great investment opportunity in the highly sought-after Black Creek Park area of Middlebur...	3 beds \| 2 baths \| 1,652 sq.ft.	$249,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 10.82% Airbnb Rental Income: $984 Traditional Rental Income: $3110 Airbnb ROI: 0.28% Traditional ROI: 10.82%
3559 WHISPER CREEK Boulevard MIDDLEBURG, FL CORNER Lot Home- Forget the stress of ''hidden costs''--NO CDD fees and every major system...	3 beds \| 2 baths \| 1,465 sq.ft.	$350,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 3.17% Airbnb Rental Income: $984 Traditional Rental Income: $1814 Airbnb ROI: -0.42% Traditional ROI: 3.17%
4619 PINE LAKE Drive MIDDLEBURG, FL Welcome to this inviting 3-bedroom, 2-bathroom home nestled in the Pine Ridge community. W...	3 beds \| 2 baths \| 1,901 sq.ft.	$350,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 2.62% Airbnb Rental Income: $984 Traditional Rental Income: $1871 Airbnb ROI: -1.15% Traditional ROI: 2.62%
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.	$699,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 4.59% Airbnb Rental Income: $5300 Traditional Rental Income: $3768 Airbnb ROI: 5.29% Traditional ROI: 4.59%
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.	$276,999	Airbnb cash on cash: -0.36% Traditional cash on cash: 5.8% Airbnb Rental Income: $984 Traditional Rental Income: $2240 Airbnb ROI: -0.36% Traditional ROI: 5.8%
187 SORREL Street MIDDLEBURG, FL Welcome home to this two-story 4 bedroom, 3 bathroom home with 9' ceilings, located on 1.2...	4 beds \| 3 baths \| 2,046 sq.ft.	$599,990	Airbnb cash on cash: 5.89% Traditional cash on cash: 2.92% Airbnb Rental Income: $5300 Traditional Rental Income: $2562 Airbnb ROI: 5.89% Traditional ROI: 2.92%
4665 GOPHER Street MIDDLEBURG, FL Welcome to this nearly new home offering modern design, functional space, and over an acre...	4 beds \| 3 baths \| 2,000 sq.ft.	$460,000	Airbnb cash on cash: 8.49% Traditional cash on cash: 4.56% Airbnb Rental Income: $5300 Traditional Rental Income: $2536 Airbnb ROI: 8.49% Traditional ROI: 4.56%
2003 AMBERLY Drive MIDDLEBURG, FL Welcome to this upgraded 3-bedroom, 2-bath home in Greyhawk! The interior has a functional...	3 beds \| 2 baths \| 1,811 sq.ft.	$350,000	Airbnb cash on cash: -1.6% Traditional cash on cash: 3.16% Airbnb Rental Income: $984 Traditional Rental Income: $2196 Airbnb ROI: -1.6% Traditional ROI: 3.16%
3806 FEATHERSTONE Court MIDDLEBURG, FL Breathtaking Lennar NextGen 4/4 home in one of the largest lot in Greyhawk! Soaring 12-foo...	4 beds \| 4 baths \| 3,008 sq.ft.	$634,900	Airbnb cash on cash: 4.44% Traditional cash on cash: 4.49% Airbnb Rental Income: $5300 Traditional Rental Income: $4256 Airbnb ROI: 4.44% Traditional ROI: 4.49%

Real Estate investment in Middleburg, FL

There are 142 properties for sale in the city of Middleburg . The median list price in Middleburg is $335,000 and the average price per square foot is $178. In April 2026, the average monthly cash on cash return in Middleburg is 5.00%. The average monthly rental income in Middleburg is $2,298.

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

There are 142 investment properties available for sale in Middleburg.

In 2026, 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

2030 WAYFARE Lane

MIDDLEBURG, FL

4 beds | 3 baths | 2,184 sq.ft.

$559,000

Airbnb cash on cash: 6.24%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $5300

Traditional Rental Income: $2889

Airbnb ROI: 6.24%

Traditional ROI: 3.68%

4141 SIDEWINDER Trail

MIDDLEBURG, FL

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

$515,000

Airbnb cash on cash: 7.36%

Traditional cash on cash: 9.85%

Airbnb Rental Income: $5300

Traditional Rental Income: $5430

Airbnb ROI: 7.36%

Traditional ROI: 9.85%

1884 PARADISE MOORINGS Boulevard

MIDDLEBURG, FL

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

$648,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $5300

Traditional Rental Income: $2290

Airbnb ROI: 4.83%

Traditional ROI: 1.62%

4732 SADDLEHORN Trail

MIDDLEBURG, FL

5 beds | 3 baths | 3,686 sq.ft.

$849,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3%

Airbnb Rental Income: $null

Traditional Rental Income: $3937

Airbnb ROI: N/A

Traditional ROI: 3%

3938 SUNSET SKY Road

MIDDLEBURG, FL

3 beds | 2 baths | 2,056 sq.ft.

$995,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: 1.09%

Airbnb Rental Income: $984

Traditional Rental Income: $2724

Airbnb ROI: -1.17%

Traditional ROI: 1.09%

2415 MOON HARBOR Way

MIDDLEBURG, FL

4 beds | 2 baths | 2,303 sq.ft.

$450,000

Airbnb cash on cash: 7.77%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $5300

Traditional Rental Income: $3046

Airbnb ROI: 7.77%

Traditional ROI: 4.97%

2246 BOTANY Street

MIDDLEBURG, FL

3 beds | 2 baths | 1,212 sq.ft.

$285,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 5.24%

Airbnb Rental Income: $984

Traditional Rental Income: $1976

Airbnb ROI: 0.23%

Traditional ROI: 5.24%

1998 LENOX Court

MIDDLEBURG, FL

3 beds | 3 baths | 2,152 sq.ft.

$369,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 6.56%

Airbnb Rental Income: $984

Traditional Rental Income: $3058

Airbnb ROI: -0.45%