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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2198 FRESCO Drive MIDDLEBURG, FL This perfect starter home is ideally situated on a tranquil interior lake lot. The home ...	3 beds \| 3 baths \| 1,638 sq.ft.	$299,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 4.06% Airbnb Rental Income: $2436 Traditional Rental Income: $1842 Airbnb ROI: 4.06% Traditional ROI: 4.06%
4079 SANDHILL CRANE Terrace MIDDLEBURG, FL Welcome to this stunning 5-bedroom, 2.5-bath home, beautifully updated and in impeccable c...	5 beds \| 3 baths \| 2,620 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.96% Airbnb Rental Income: $null Traditional Rental Income: $2539 Airbnb ROI: N/A Traditional ROI: 3.96%
1869 LAGO DEL SUR Drive MIDDLEBURG, FL Welcome to your dream townhouse! Step inside this desirable end unit and be greeted by the...	2 beds \| 3 baths \| 1,152 sq.ft.	$223,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 6.5% Airbnb Rental Income: $2688 Traditional Rental Income: $1930 Airbnb ROI: 7.07% Traditional ROI: 6.5%
2882 TUSCARORA Trail MIDDLEBURG, FL Spacious 4-bedroom, 2-bathroom family home located in a serene neighborhood. The living ro...	4 beds \| 2 baths \| 1,714 sq.ft.	$330,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 4.56% Airbnb Rental Income: $3776 Traditional Rental Income: $2216 Airbnb ROI: 6.96% Traditional ROI: 4.56%
2883 CREEK Street MIDDLEBURG, FL PRICE REDUCTION with Motivated Sellers! A complete boaters dream, welcome to your Waterfro...	3 beds \| 2 baths \| 1,778 sq.ft.	$624,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 2.39% Airbnb Rental Income: $2436 Traditional Rental Income: $2602 Airbnb ROI: 1.08% Traditional ROI: 2.39%
2969 BILOXI Trail MIDDLEBURG, FL Welcome to a beautifully updated home boasting a neutral color paint scheme and fresh inte...	4 beds \| 2 baths \| 1,770 sq.ft.	$330,000	Airbnb cash on cash: 7.39% Traditional cash on cash: 5.09% Airbnb Rental Income: $3776 Traditional Rental Income: $2245 Airbnb ROI: 7.39% Traditional ROI: 5.09%
3024 LONGLEAF RANCH Circle MIDDLEBURG, FL If you've been yearning for a quintessential southern ranch lifestyle, complete with front...	4 beds \| 2 baths \| 1,728 sq.ft.	$424,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 3.01% Airbnb Rental Income: $3776 Traditional Rental Income: $2121 Airbnb ROI: 5.12% Traditional ROI: 3.01%
2996 TUSCARORA Trail MIDDLEBURG, FL Situated on a quiet cul-de-sac with serene pond views, this spacious home offers 4 bedroom...	4 beds \| 2 baths \| 1,904 sq.ft.	$310,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 6.17% Airbnb Rental Income: $3776 Traditional Rental Income: $2606 Airbnb ROI: 7.37% Traditional ROI: 6.17%
1430 LANTERN LIGHT Trail MIDDLEBURG, FL STUNNING! Offering over 3,000 sq ft of spacious living, perfectly designed for comfort and...	5 beds \| 3 baths \| 3,107 sq.ft.	$470,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.69% Airbnb Rental Income: $null Traditional Rental Income: $2951 Airbnb ROI: N/A Traditional ROI: 3.69%
1621 TEABERRY Drive MIDDLEBURG, FL Welcome to your perfect move-in ready home! This inviting 3-bedroom, 2-bathroom gem is des...	3 beds \| 2 baths \| 1,241 sq.ft.	$249,990	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.93% Airbnb Rental Income: $2436 Traditional Rental Income: $1820 Airbnb ROI: 5.01% Traditional ROI: 4.93%
4770 KANGAROO Circle MIDDLEBURG, FL Nestled just outside the city on a spacious 1.4-acre lot, this charming three-bedroom, two...	3 beds \| 2 baths \| 1,384 sq.ft.	$319,900	Airbnb cash on cash: 4.1% Traditional cash on cash: 4.2% Airbnb Rental Income: $2436 Traditional Rental Income: $1870 Airbnb ROI: 4.1% Traditional ROI: 4.2%
3191 WILDERNESS Drive MIDDLEBURG, FL Discover this delightful three-bedroom, two-bathroom home in Middleburg, nestled on a near...	3 beds \| 3 baths \| 2,166 sq.ft.	$355,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 5.54% Airbnb Rental Income: $2436 Traditional Rental Income: $2714 Airbnb ROI: 2.92% Traditional ROI: 5.54%
4761 LEOPARD Circle MIDDLEBURG, FL Fantastic home in Black Creek Park, nestled on 1.47 acres with No CDD or HOA fees! With an...	3 beds \| 2 baths \| 1,516 sq.ft.	$385,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.45% Airbnb Rental Income: $2436 Traditional Rental Income: $1993 Airbnb ROI: 3.03% Traditional ROI: 3.45%
2016 AMBERLY Drive MIDDLEBURG, FL PRICED TO SELL! $2000 LENDER CREDIT towards closing. Own this beautiful 2 yo like new ho...	3 beds \| 3 baths \| 2,425 sq.ft.	$390,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 4.12% Airbnb Rental Income: $2436 Traditional Rental Income: $2713 Airbnb ROI: 1.73% Traditional ROI: 4.12%
4010 OLDE TYME Place MIDDLEBURG, FL Welcome to this charming property, which boasts a cozy fireplace, perfect for those chilly...	3 beds \| 2 baths \| 1,634 sq.ft.	$336,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 4.01% Airbnb Rental Income: $2436 Traditional Rental Income: $2084 Airbnb ROI: 3.24% Traditional ROI: 4.01%
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%
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%
3337 RIVERBANK Drive MIDDLEBURG, FL Discover your ideal family haven in this beautiful 4-BR, 2-bath home situated on a generou...	4 beds \| 2 baths \| 1,972 sq.ft.	$309,900	Airbnb cash on cash: 7.16% Traditional cash on cash: 5.33% Airbnb Rental Income: $3776 Traditional Rental Income: $2425 Airbnb ROI: 7.16% Traditional ROI: 5.33%
1326 HIGHFIELD Lane MIDDLEBURG, FL Open House Sat 12/14 11-1. Come take a look at this home with a POOL! Large open floor pla...	4 beds \| 3 baths \| 2,343 sq.ft.	$432,500	Airbnb cash on cash: 4.9% Traditional cash on cash: 4.23% Airbnb Rental Income: $3776 Traditional Rental Income: $2684 Airbnb ROI: 4.9% Traditional ROI: 4.23%
4066 SUNRISE FARMS Road MIDDLEBURG, FL Priced to sell, this beautifully renovated home sits on 7.5 ACRES with OVER 6,000sf of sto...	3 beds \| 2 baths \| 2,475 sq.ft.	$694,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 0.94% Airbnb Rental Income: $2436 Traditional Rental Income: $2144 Airbnb ROI: 0.47% Traditional ROI: 0.94%
2321 HALPERNS Way MIDDLEBURG, FL Welcome to a 1.5 ACRE Riverfront Paradise! Tucked away on a quiet street with majestic oak...	4 beds \| 5 baths \| 4,343 sq.ft.	$999,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 4.61% Airbnb Rental Income: $3776 Traditional Rental Income: $5707 Airbnb ROI: 1.65% Traditional ROI: 4.61%
3557 GRAYSON Lane MIDDLEBURG, FL Must come see this gorgeous 2 story home. This lovely home is located in Cameron Oaks comm...	4 beds \| 3 baths \| 2,213 sq.ft.	$400,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 4.36% Airbnb Rental Income: $3776 Traditional Rental Income: $2664 Airbnb ROI: 5.15% Traditional ROI: 4.36%
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%
2388 HALPERNS Way MIDDLEBURG, FL Elegant. Classic. This split 4 bedroom 3 bath brick home sits back on a hill on approx 1.3...	4 beds \| 3 baths \| 2,259 sq.ft.	$494,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.85% Airbnb Rental Income: $3776 Traditional Rental Income: $2866 Airbnb ROI: 4.04% Traditional ROI: 3.85%
5684 MAVERICK Road MIDDLEBURG, FL Renovated Luxury Farmhouse with Mother-in-Law Suite on 1.5 Acres in Clay Hill Price: $4...	4 beds \| 3 baths \| 2,324 sq.ft.	$410,000	Airbnb cash on cash: 5.66% Traditional cash on cash: 5.37% Airbnb Rental Income: $3776 Traditional Rental Income: $2844 Airbnb ROI: 5.66% Traditional ROI: 5.37%
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.	$255,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 4.12% Airbnb Rental Income: $2436 Traditional Rental Income: $1588 Airbnb ROI: 5.18% Traditional ROI: 4.12%
2050 AMBERLY Drive MIDDLEBURG, FL Nestled in the tranquil embrace of suburban living, this immaculate residence stands as a ...	3 beds \| 3 baths \| 1,860 sq.ft.	$331,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 5.22% Airbnb Rental Income: $2436 Traditional Rental Income: $2377 Airbnb ROI: 3.49% Traditional ROI: 5.22%
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.	$490,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 3.44% Airbnb Rental Income: $2436 Traditional Rental Income: $2479 Airbnb ROI: 2.05% Traditional ROI: 3.44%
4228 CARIBBEAN PINE Court MIDDLEBURG, FL Nestled on a quiet, cul-de-sac street, welcome to your almost NEW dream home, built in Dec...	4 beds \| 2 baths \| 1,864 sq.ft.	$380,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 3.1% Airbnb Rental Income: $3776 Traditional Rental Income: $2198 Airbnb ROI: 5.24% Traditional ROI: 3.1%
1075 WETLAND RIDGE Circle MIDDLEBURG, FL This 4 bedroom 3 bathroom home two bonus rooms that are currently set up as a home gym and...	4 beds \| 3 baths \| 2,670 sq.ft.	$415,000	Airbnb cash on cash: 5.22% Traditional cash on cash: 4.84% Airbnb Rental Income: $3776 Traditional Rental Income: $2811 Airbnb ROI: 5.22% Traditional ROI: 4.84%
3467 LYNN Court MIDDLEBURG, FL Welcome to your dream home where modern features blend seamlessly with an atmosphere of wa...	4 beds \| 2 baths \| 1,488 sq.ft.	$304,000	Airbnb cash on cash: 7.91% Traditional cash on cash: 4.47% Airbnb Rental Income: $3776 Traditional Rental Income: $1975 Airbnb ROI: 7.91% Traditional ROI: 4.47%
2989 SPARKLEBERRY Drive MIDDLEBURG, FL Beautiful brick home in a most sought after gated community in Middleburg...Villages of Fi...	4 beds \| 3 baths \| 3,037 sq.ft.	$548,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 4.49% Airbnb Rental Income: $3776 Traditional Rental Income: $2990 Airbnb ROI: 4.43% Traditional ROI: 4.49%
3212 THUNDER Road MIDDLEBURG, FL This stunning 3-bed/2-bath countryside retreat boasts 2,462 sq ft of living space nestled ...	3 beds \| 2 baths \| 2,462 sq.ft.	$1,190,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 0.63% Airbnb Rental Income: $2436 Traditional Rental Income: $2692 Airbnb ROI: -0.14% Traditional ROI: 0.63%
94 CONIFER Circle MIDDLEBURG, FL Ready for all Investors and Buyers! The newly painted home and it's new metal roof are mai...	3 beds \| 2 baths \| 1,568 sq.ft.	$349,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 4.49% Airbnb Rental Income: $2436 Traditional Rental Income: $2019 Airbnb ROI: 3.95% Traditional ROI: 4.49%
3165 RAVINES Road #3601 MIDDLEBURG, FL Charming 1 Bedroom, 1 Bathroom Condo in Private Gated Community Escape to your serene o...	1 beds \| 1 baths \| 420 sq.ft.	$125,900	Airbnb cash on cash: 1.99% Traditional cash on cash: 9.15% Airbnb Rental Income: $1217 Traditional Rental Income: $1693 Airbnb ROI: 1.99% Traditional ROI: 9.15%
2872 CRANBERRY Circle MIDDLEBURG, FL Build your DREAM HOME on this serene 1.21 acre lot! This 143' x 341 homesite has been part...	3 beds \| 2 baths \| 1,779 sq.ft.	$399,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 4.45% Airbnb Rental Income: $2436 Traditional Rental Income: $2178 Airbnb ROI: 3.55% Traditional ROI: 4.45%
4059 INGLEWOOD Drive MIDDLEBURG, FL Discover elevated Florida living at 4059 Inglewood Dr, Middleburg! This unique 3-bedroom, ...	3 beds \| 2 baths \| 2,460 sq.ft.	$479,999	Airbnb cash on cash: 2.4% Traditional cash on cash: 3.71% Airbnb Rental Income: $2436 Traditional Rental Income: $2426 Airbnb ROI: 2.4% Traditional ROI: 3.71%
2341 OAK POINT Terrace MIDDLEBURG, FL Come build your custom dream home in the highly sought after and exclusive gated community...	3 beds \| 2 baths \| 1,800 sq.ft.	$350,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 4.79% Airbnb Rental Income: $2436 Traditional Rental Income: $2203 Airbnb ROI: 3.69% Traditional ROI: 4.79%
4117 FISHING CREEK Lane MIDDLEBURG, FL Beautiful, well cared Open Floor plan 3 Bedrooms, 2 Bathrooms home in the sought after com...	3 beds \| 2 baths \| 1,931 sq.ft.	$399,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 3.75% Airbnb Rental Income: $2436 Traditional Rental Income: $2277 Airbnb ROI: 2.59% Traditional ROI: 3.75%
1276 WINDING BROOK Court MIDDLEBURG, FL Welcome to this charming 4-bedroom, 2-bathroom home located in Middleburg, FL. This house ...	4 beds \| 2 baths \| 2,003 sq.ft.	$375,000	Airbnb cash on cash: 5.99% Traditional cash on cash: 3.95% Airbnb Rental Income: $3776 Traditional Rental Income: $2241 Airbnb ROI: 5.99% Traditional ROI: 3.95%

Real Estate investment in Middleburg, FL

There are 145 properties for sale in the city of Middleburg . The median list price in Middleburg is $352,500 and the average price per square foot is $184. In December 2024, the average monthly cash on cash return in Middleburg is 4.00%. The average monthly rental income in Middleburg is $2,149.

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

There are 145 investment properties available for sale in Middleburg.

In 2024, 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

2198 FRESCO Drive

MIDDLEBURG, FL

3 beds | 3 baths | 1,638 sq.ft.

$299,900

Airbnb cash on cash: 4.06%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $2436

Traditional Rental Income: $1842

Airbnb ROI: 4.06%

Traditional ROI: 4.06%

4079 SANDHILL CRANE Terrace

MIDDLEBURG, FL

5 beds | 3 baths | 2,620 sq.ft.

$400,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2539

Airbnb ROI: N/A

Traditional ROI: 3.96%

1869 LAGO DEL SUR Drive

MIDDLEBURG, FL

2 beds | 3 baths | 1,152 sq.ft.

$223,000

Airbnb cash on cash: 7.07%

Traditional cash on cash: 6.5%

Airbnb Rental Income: $2688

Traditional Rental Income: $1930

Airbnb ROI: 7.07%

Traditional ROI: 6.5%

2882 TUSCARORA Trail

MIDDLEBURG, FL

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

$330,000

Airbnb cash on cash: 6.96%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $3776

Traditional Rental Income: $2216

Airbnb ROI: 6.96%

Traditional ROI: 4.56%

2883 CREEK Street

MIDDLEBURG, FL

3 beds | 2 baths | 1,778 sq.ft.

$624,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $2436

Traditional Rental Income: $2602

Airbnb ROI: 1.08%

Traditional ROI: 2.39%

2969 BILOXI Trail

MIDDLEBURG, FL

4 beds | 2 baths | 1,770 sq.ft.

$330,000

Airbnb cash on cash: 7.39%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $3776

Traditional Rental Income: $2245

Airbnb ROI: 7.39%

Traditional ROI: 5.09%

3024 LONGLEAF RANCH Circle

MIDDLEBURG, FL

4 beds | 2 baths | 1,728 sq.ft.

$424,000

Airbnb cash on cash: 5.12%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $3776

Traditional Rental Income: $2121

Airbnb ROI: 5.12%

Traditional ROI: 3.01%

2996 TUSCARORA Trail

MIDDLEBURG, FL

4 beds | 2 baths | 1,904 sq.ft.

$310,000

Airbnb cash on cash: 7.37%

Traditional cash on cash: 6.17%

Airbnb Rental Income: $3776

Traditional Rental Income: $2606

Airbnb ROI: 7.37%