Real Estate Investment Properties for Sale in Maitland, FL

Looking for investment property in Maitland, FL with high ROI ?

Explore a variety of short-term homes & houses in Maitland, FL. Invest wisely with VRBO & Maitland, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Maitland, FL

Search for Single Family Residential for Sale in Maitland, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 45 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1301 DRUID ISLE ROAD Maitland, FL Under contract-accepting backup offers. Nestled in the highly desirable Druid Isle neighbo...	4 beds \| 3 baths \| 2,162 sq.ft.	$649,990	Airbnb cash on cash: 4.37% Traditional cash on cash: 3.74% Airbnb Rental Income: $5007 Traditional Rental Income: $3600 Airbnb ROI: 4.37% Traditional ROI: 3.74%
890 CRANES COURT Maitland, FL Under contract-accepting backup offers. Nestled in the QUIET, oak tree lined and GATED com...	4 beds \| 4 baths \| 3,221 sq.ft.	$1,100,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 2.03% Airbnb Rental Income: $5007 Traditional Rental Income: $4277 Airbnb ROI: 1.74% Traditional ROI: 2.03%
350 Northwind Rd Maitland, FL Nestled within the gated 9-acre Lake Maitland Owl Preserve, this striking contemporary res...	5 beds \| 4 baths \| 4,819 sq.ft.	$3,299,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 0.53% Airbnb Rental Income: $5533 Traditional Rental Income: $6480 Airbnb ROI: -0.14% Traditional ROI: 0.53%
2338 Tuscarora Trl Maitland, FL *Charming Dommerich Hills Home with Scenic Lake Views and Modern Updates* Nestled in t...	4 beds \| 2 baths \| 1,700 sq.ft.	$680,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 2.44% Airbnb Rental Income: $5007 Traditional Rental Income: $2640 Airbnb ROI: 4.55% Traditional ROI: 2.44%
2270 DELORAINE TRAIL Maitland, FL Under contract-accepting backup offers. This beautifully updated 4-bedroom, 2-bath pool ho...	4 beds \| 2 baths \| 2,000 sq.ft.	$850,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 1.67% Airbnb Rental Income: $5007 Traditional Rental Income: $2871 Airbnb ROI: 3.07% Traditional ROI: 1.67%
708 Thunder Trl Maitland, FL Welcome to 708 Thunder Trail in beautiful Maitland, Florida â a stunning 4-bedroom, 2-ba...	4 beds \| 2 baths \| 1,907 sq.ft.	$635,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 2.76% Airbnb Rental Income: $5007 Traditional Rental Income: $3074 Airbnb ROI: 4.3% Traditional ROI: 2.76%
631 Lake Catherine Dr Maitland, FL Welcome to an extraordinary lakefront sanctuary at 631 Lake Catherine Drive, where sophist...	3 beds \| 3 baths \| 2,351 sq.ft.	$1,975,000	Airbnb cash on cash: -0.19% Traditional cash on cash: -0.13% Airbnb Rental Income: $3440 Traditional Rental Income: $2779 Airbnb ROI: -0.19% Traditional ROI: -0.13%
135 Roosevelt Pl Maitland, FL This charming home boasts a wealth of valuable upgrades and improvements, making it an ent...	3 beds \| 2 baths \| 2,426 sq.ft.	$549,900	Airbnb cash on cash: 5.54% Traditional cash on cash: 2.77% Airbnb Rental Income: $5007 Traditional Rental Income: $2560 Airbnb ROI: 5.54% Traditional ROI: 2.77%
1231 Sidcup Rd Maitland, FL Prepare to be captivated by this fully renovated gem located in the highly sought after En...	3 beds \| 2 baths \| 1,798 sq.ft.	$510,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 4.29% Airbnb Rental Income: $3440 Traditional Rental Income: $2775 Airbnb ROI: 4.09% Traditional ROI: 4.29%
1619 Druid Rd Maitland, FL Tucked into prestigious Maitland Florida on coveted Druid Road, this one-of-a-kind residen...	5 beds \| 4 baths \| 3,769 sq.ft.	$920,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 2.97% Airbnb Rental Income: $5533 Traditional Rental Income: $4521 Airbnb ROI: 2.85% Traditional ROI: 2.97%
255 W George Ave Maitland, FL Experience the blend of timeless elegance and modern luxury in this Maitland estate a bloc...	5 beds \| 4 baths \| 4,814 sq.ft.	$1,700,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 2.23% Airbnb Rental Income: $5533 Traditional Rental Income: $5853 Airbnb ROI: 1.33% Traditional ROI: 2.23%
1913 Poinsetta Ln Maitland, FL Motivated Seller \| Renovated Pool Home in Prime Maitland Location This solid concrete bloc...	4 beds \| 2 baths \| 1,664 sq.ft.	$418,500	Airbnb cash on cash: 8.55% Traditional cash on cash: 4.5% Airbnb Rental Income: $5007 Traditional Rental Income: $2394 Airbnb ROI: 8.55% Traditional ROI: 4.5%
2632 DERBYSHIRE ROAD Maitland, FL Under contract-accepting backup offers. 2025 ROOF \| POOL HOME Start your new life ...	4 beds \| 2 baths \| 1,770 sq.ft.	$525,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 3.68% Airbnb Rental Income: $5007 Traditional Rental Income: $2807 Airbnb ROI: 6.08% Traditional ROI: 3.68%
736 FOREST GLEN COURT Maitland, FL One or more photo(s) has been virtually staged. Huge Price Reduction!!!!! - Motivated Sell...	4 beds \| 2 baths \| 1,647 sq.ft.	$455,000	Airbnb cash on cash: 7.03% Traditional cash on cash: 3.81% Airbnb Rental Income: $5007 Traditional Rental Income: $2614 Airbnb ROI: 7.03% Traditional ROI: 3.81%
1024 Kewannee Trl Maitland, FL One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed ...	4 beds \| 2 baths \| 1,845 sq.ft.	$550,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 3.49% Airbnb Rental Income: $5007 Traditional Rental Income: $3187 Airbnb ROI: 5.04% Traditional ROI: 3.49%
1074 Hamlet Dr Maitland, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, con...	3 beds \| 2 baths \| 1,076 sq.ft.	$308,000	Airbnb cash on cash: 7.35% Traditional cash on cash: 5% Airbnb Rental Income: $3440 Traditional Rental Income: $1997 Airbnb ROI: 7.35% Traditional ROI: 5%
2318 CASTLEWOOD ROAD Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Yo...	4 beds \| 3 baths \| 2,335 sq.ft.	$580,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 4.61% Airbnb Rental Income: $5007 Traditional Rental Income: $3329 Airbnb ROI: 5.82% Traditional ROI: 4.61%
2464 DERBYSHIRE ROAD Maitland, FL Under contract-accepting backup offers. Auction Property. Welcome to this inviting home of...	3 beds \| 2 baths \| 1,860 sq.ft.	$411,900	Airbnb cash on cash: 5.27% Traditional cash on cash: 5.95% Airbnb Rental Income: $3440 Traditional Rental Income: $2940 Airbnb ROI: 5.27% Traditional ROI: 5.95%
1416 Caring Ct Maitland, FL Beautifully maintained Maitland home in the gated community of Montacino on Lake Charity. ...	4 beds \| 3 baths \| 3,451 sq.ft.	$925,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 1.96% Airbnb Rental Income: $5007 Traditional Rental Income: $4083 Airbnb ROI: 1.84% Traditional ROI: 1.96%
314 Banyan Dr Maitland, FL Experience Modern Florida Living at Its Finest Step inside this fully remodeled 3-bedroom,...	3 beds \| 2 baths \| 1,234 sq.ft.	$400,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 3.59% Airbnb Rental Income: $3440 Traditional Rental Income: $1940 Airbnb ROI: 5.56% Traditional ROI: 3.59%
400 BOYNTON ROAD Maitland, FL Special Opportunity in the heart of Maitland! Own a piece of history or build your dream ...	3 beds \| 2 baths \| 1,520 sq.ft.	$525,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.15% Airbnb Rental Income: $3440 Traditional Rental Income: $2286 Airbnb ROI: 3.95% Traditional ROI: 3.15%
2525 NATIVE COURT Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 2,240 sq.ft.	$599,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 4.61% Airbnb Rental Income: $5007 Traditional Rental Income: $3512 Airbnb ROI: 5.45% Traditional ROI: 4.61%
633 Magnolia Dr Maitland, FL Welcome to this Maitland 3-bedroom, 2-bath pool home offering incredible potential on a de...	3 beds \| 2 baths \| 1,285 sq.ft.	$370,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 4.94% Airbnb Rental Income: $3440 Traditional Rental Income: $2295 Airbnb ROI: 6.04% Traditional ROI: 4.94%
2167 MOHAWK TRAIL Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ce...	3 beds \| 2 baths \| 2,162 sq.ft.	$625,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 1.74% Airbnb Rental Income: $3440 Traditional Rental Income: $2641 Airbnb ROI: 1.8% Traditional ROI: 1.74%
1447 CARING COURT Maitland, FL Beautiful move-in ready home in the highly sought-after gated community of Montacino, loca...	3 beds \| 3 baths \| 2,110 sq.ft.	$625,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 2.29% Airbnb Rental Income: $3440 Traditional Rental Income: $2623 Airbnb ROI: 2.38% Traditional ROI: 2.29%
2065 Derbyshire Rd Maitland, FL Beautifully renovated and move-in ready, this 3-bedroom, 2-bath home offers modern design ...	3 beds \| 2 baths \| 1,430 sq.ft.	$499,990	Airbnb cash on cash: 4.21% Traditional cash on cash: 3.14% Airbnb Rental Income: $3440 Traditional Rental Income: $2175 Airbnb ROI: 4.21% Traditional ROI: 3.14%
67 Cypress Ln Maitland, FL Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majesti...	4 beds \| 3 baths \| 2,292 sq.ft.	$1,339,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 1.05% Airbnb Rental Income: $5007 Traditional Rental Income: $3028 Airbnb ROI: 1.81% Traditional ROI: 1.05%
1933 SOUTH BOULEVARD Maitland, FL Under contract-accepting backup offers. Perfectly positioned in the highly sought-after Ma...	5 beds \| 3 baths \| 2,376 sq.ft.	$600,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 3.09% Airbnb Rental Income: $5533 Traditional Rental Income: $2720 Airbnb ROI: 6.13% Traditional ROI: 3.09%
185 BIRCHWOOD DRIVE Maitland, FL Under contract-accepting backup offers. Welcome to 185 Birchwood Drive, a rare Maitland SK...	4 beds \| 3 baths \| 2,253 sq.ft.	$800,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 1.56% Airbnb Rental Income: $5007 Traditional Rental Income: $2258 Airbnb ROI: 3.88% Traditional ROI: 1.56%

Your search for investment property begins and ends here

Single Family Homes for Sale in Maitland, FL

1301 DRUID ISLE ROAD

Maitland, FL

4 beds | 3 baths | 2,162 sq.ft.

$649,990

Airbnb cash on cash: 4.37%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $5007

Traditional Rental Income: $3600

Airbnb ROI: 4.37%

Traditional ROI: 3.74%

890 CRANES COURT

Maitland, FL

4 beds | 4 baths | 3,221 sq.ft.

$1,100,000

Airbnb cash on cash: 1.74%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $5007

Traditional Rental Income: $4277

Airbnb ROI: 1.74%

Traditional ROI: 2.03%

350 Northwind Rd

Maitland, FL

5 beds | 4 baths | 4,819 sq.ft.

$3,299,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $5533

Traditional Rental Income: $6480

Airbnb ROI: -0.14%

Traditional ROI: 0.53%

2338 Tuscarora Trl

Maitland, FL

4 beds | 2 baths | 1,700 sq.ft.

$680,000

Airbnb cash on cash: 4.55%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $5007

Traditional Rental Income: $2640

Airbnb ROI: 4.55%

Traditional ROI: 2.44%

2270 DELORAINE TRAIL

Maitland, FL

4 beds | 2 baths | 2,000 sq.ft.

$850,000

Airbnb cash on cash: 3.07%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $5007

Traditional Rental Income: $2871

Airbnb ROI: 3.07%

Traditional ROI: 1.67%

708 Thunder Trl

Maitland, FL

4 beds | 2 baths | 1,907 sq.ft.

$635,000

Airbnb cash on cash: 4.3%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $5007

Traditional Rental Income: $3074

Airbnb ROI: 4.3%

Traditional ROI: 2.76%

631 Lake Catherine Dr

Maitland, FL

3 beds | 3 baths | 2,351 sq.ft.

$1,975,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: -0.13%

Airbnb Rental Income: $3440

Traditional Rental Income: $2779

Airbnb ROI: -0.19%

Traditional ROI: -0.13%

135 Roosevelt Pl

Maitland, FL

3 beds | 2 baths | 2,426 sq.ft.

$549,900

Airbnb cash on cash: 5.54%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $5007

Traditional Rental Income: $2560

Airbnb ROI: 5.54%