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
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.	$500,000	Airbnb cash on cash: 7.6% Traditional cash on cash: 8.44% Airbnb Rental Income: $5300 Traditional Rental Income: $4617 Airbnb ROI: 7.6% Traditional ROI: 8.44%
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: 3.11% Airbnb Rental Income: $5300 Traditional Rental Income: $3189 Airbnb ROI: 4.83% Traditional ROI: 3.11%
4916 CREEK BLUFF Lane MIDDLEBURG, FL USDA 0% Down Eligible, Beautifully refreshed 4-bedroom, 2-bathroom home located in Pine Ri...	4 beds \| 2 baths \| 2,119 sq.ft.	$339,000	Airbnb cash on cash: 9.86% Traditional cash on cash: 6.09% Airbnb Rental Income: $5300 Traditional Rental Income: $3028 Airbnb ROI: 9.86% Traditional ROI: 6.09%
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: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $5233 Airbnb ROI: N/A Traditional ROI: 4.63%
4072 SCENIC Drive MIDDLEBURG, FL Creekside Charm Welcome to your peaceful retreat nestled along a scenic creek, offering th...	3 beds \| 2 baths \| 1,632 sq.ft.	$525,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 2.93% Airbnb Rental Income: $984 Traditional Rental Income: $2579 Airbnb ROI: -1.04% Traditional ROI: 2.93%
1556 NIGHT OWL Trail MIDDLEBURG, FL Beautiful move-in ready home located on a desirable corner lot in a quiet and well-establi...	3 beds \| 2 baths \| 1,558 sq.ft.	$305,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 4.5% Airbnb Rental Income: $984 Traditional Rental Income: $2257 Airbnb ROI: -1.16% Traditional ROI: 4.5%
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: 1.18% Airbnb Rental Income: $984 Traditional Rental Income: $2807 Airbnb ROI: -1.17% 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.	$368,900	Airbnb cash on cash: -0.45% Traditional cash on cash: 7.87% Airbnb Rental Income: $984 Traditional Rental Income: $3512 Airbnb ROI: -0.45% Traditional ROI: 7.87%
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.	$1,399,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 1.29% Airbnb Rental Income: $5300 Traditional Rental Income: $4226 Airbnb ROI: 1.29% Traditional ROI: 1.29%
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: 3.61% Airbnb Rental Income: $984 Traditional Rental Income: $2189 Airbnb ROI: -1.34% Traditional ROI: 3.61%
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: 6.61% Airbnb Rental Income: $5300 Traditional Rental Income: $4129 Airbnb ROI: 6.85% Traditional ROI: 6.61%
3798 BEDFORD Drive MIDDLEBURG, FL Step inside & be instantly welcomed by soaring ceilings and an abundance of natural light ...	5 beds \| 3 baths \| 2,496 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $3386 Airbnb ROI: N/A Traditional ROI: 6.86%
1840 YUKON Court MIDDLEBURG, FL Short Sale. Welcome Home! This adorable 3-bedroom, 2-bathroom home offers so much potentia...	3 beds \| 2 baths \| 1,272 sq.ft.	$244,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 6.73% Airbnb Rental Income: $984 Traditional Rental Income: $2180 Airbnb ROI: 0.02% Traditional ROI: 6.73%
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.	$275,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 9.23% Airbnb Rental Income: $984 Traditional Rental Income: $2938 Airbnb ROI: 0.33% Traditional ROI: 9.23%
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%
2929 LUCILLE LANE MIDDLEBURG, FL NEW INCENTIVES: $7,000 SELLER CREDIT used towards closing costs or rate buy down with acce...	3 beds \| 3 baths \| 1,877 sq.ft.	$348,500	Airbnb cash on cash: -0.33% Traditional cash on cash: 6.13% Airbnb Rental Income: $984 Traditional Rental Income: $2744 Airbnb ROI: -0.33% Traditional ROI: 6.13%
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: 0.97% Airbnb Rental Income: $634 Traditional Rental Income: $1812 Airbnb ROI: -1% Traditional ROI: 0.97%
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: 7.46% Airbnb Rental Income: $5300 Traditional Rental Income: $3869 Airbnb ROI: 8.43% Traditional ROI: 7.46%
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.	$187,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 8.92% Airbnb Rental Income: $984 Traditional Rental Income: $2146 Airbnb ROI: 0.4% Traditional ROI: 8.92%
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: 6.52% Airbnb Rental Income: $984 Traditional Rental Income: $2679 Airbnb ROI: -0.73% Traditional ROI: 6.52%
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: 6.11% Airbnb Rental Income: $984 Traditional Rental Income: $1999 Airbnb ROI: 0.2% Traditional ROI: 6.11%
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.	$335,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 5.68% Airbnb Rental Income: $984 Traditional Rental Income: $2869 Airbnb ROI: -1.43% Traditional ROI: 5.68%
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%
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: 4.3% Airbnb Rental Income: $984 Traditional Rental Income: $2183 Airbnb ROI: -0.42% Traditional ROI: 4.3%
2990 RAVINES Road #1422 MIDDLEBURG, FL Tucked beneath the trees in the gated community of The Ravines, this thoughtfully designed...	1 beds \| 2 baths \| 848 sq.ft.	$144,900	Airbnb cash on cash: 1.19% Traditional cash on cash: 5.5% Airbnb Rental Income: $963 Traditional Rental Income: $1212 Airbnb ROI: 1.19% Traditional ROI: 5.5%
3165 RAVINES Road #3601 MIDDLEBURG, FL Charming Studio Condo in Private Gated Community Escape to your serene oasis in this delig...	1 beds \| 1 baths \| 420 sq.ft.	$139,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 8.23% Airbnb Rental Income: $963 Traditional Rental Income: $1693 Airbnb ROI: 0.13% Traditional ROI: 8.23%
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: 4.66% Airbnb Rental Income: $984 Traditional Rental Income: $2541 Airbnb ROI: -1.15% Traditional ROI: 4.66%
2349 TIGRESS Lane MIDDLEBURG, FL SELLER FINANCING AVAILABLE! No Bank Approval Needed! Corner lot Screend in POOL Home in th...	3 beds \| 2 baths \| 1,661 sq.ft.	$389,997	Airbnb cash on cash: -0.57% Traditional cash on cash: 4.02% Airbnb Rental Income: $984 Traditional Rental Income: $2311 Airbnb ROI: -0.57% Traditional ROI: 4.02%
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.	$689,900	Airbnb cash on cash: 5.37% Traditional cash on cash: 4.92% Airbnb Rental Income: $5300 Traditional Rental Income: $3938 Airbnb ROI: 5.37% Traditional ROI: 4.92%
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.	$275,999	Airbnb cash on cash: -0.36% Traditional cash on cash: 6.04% Airbnb Rental Income: $984 Traditional Rental Income: $2297 Airbnb ROI: -0.36% Traditional ROI: 6.04%
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: 5.59% Airbnb Rental Income: $5300 Traditional Rental Income: $4058 Airbnb ROI: 5.89% Traditional ROI: 5.59%

Real Estate investment in Middleburg, FL

There are 150 properties for sale in the city of Middleburg . The median list price in Middleburg is $342,500 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 $2,414.

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

There are 150 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

4141 SIDEWINDER Trail

MIDDLEBURG, FL

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

$500,000

Airbnb cash on cash: 7.6%

Traditional cash on cash: 8.44%

Airbnb Rental Income: $5300

Traditional Rental Income: $4617

Airbnb ROI: 7.6%

Traditional ROI: 8.44%

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: 3.11%

Airbnb Rental Income: $5300

Traditional Rental Income: $3189

Airbnb ROI: 4.83%

Traditional ROI: 3.11%

4916 CREEK BLUFF Lane

MIDDLEBURG, FL

4 beds | 2 baths | 2,119 sq.ft.

$339,000

Airbnb cash on cash: 9.86%

Traditional cash on cash: 6.09%

Airbnb Rental Income: $5300

Traditional Rental Income: $3028

Airbnb ROI: 9.86%

Traditional ROI: 6.09%

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: 4.63%

Airbnb Rental Income: $null

Traditional Rental Income: $5233

Airbnb ROI: N/A

Traditional ROI: 4.63%

4072 SCENIC Drive

MIDDLEBURG, FL

3 beds | 2 baths | 1,632 sq.ft.

$525,000

Airbnb cash on cash: -1.04%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $984

Traditional Rental Income: $2579

Airbnb ROI: -1.04%

Traditional ROI: 2.93%

1556 NIGHT OWL Trail

MIDDLEBURG, FL

3 beds | 2 baths | 1,558 sq.ft.

$305,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $984

Traditional Rental Income: $2257

Airbnb ROI: -1.16%

Traditional ROI: 4.5%

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: 1.18%

Airbnb Rental Income: $984

Traditional Rental Income: $2807

Airbnb ROI: -1.17%

Traditional ROI: 1.18%

1998 LENOX Court

MIDDLEBURG, FL

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

$368,900

Airbnb cash on cash: -0.45%

Traditional cash on cash: 7.87%

Airbnb Rental Income: $984

Traditional Rental Income: $3512

Airbnb ROI: -0.45%