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 40 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
195 E FAITH TERRACE Maitland, FL Under contract-accepting backup offers. Perfectly positioned on the tranquil shores of Lak...	3 beds \| 2 baths \| 2,502 sq.ft.	$825,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 1.65% Airbnb Rental Income: $3440 Traditional Rental Income: $2737 Airbnb ROI: 1.58% Traditional ROI: 1.65%
515 W FAITH TERRACE Maitland, FL Under contract-accepting backup offers. Beautiful Mid-Century Modern in Maitland! Sylish 3...	3 beds \| 2 baths \| 2,205 sq.ft.	$515,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 4.13% Airbnb Rental Income: $3440 Traditional Rental Income: $3030 Airbnb ROI: 3.4% Traditional ROI: 4.13%
1655 SUNNYSIDE DRIVE Maitland, FL Welcome to 1655 Sunnyside Drive, a beautifully charming home nestled on a picturesque corn...	3 beds \| 2 baths \| 1,418 sq.ft.	$699,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.04% Airbnb Rental Income: $3440 Traditional Rental Income: $2319 Airbnb ROI: 1.59% Traditional ROI: 1.04%
2270 DELORAINE TRAIL Maitland, FL This beautifully updated 4-bedroom, 2-bath pool home offers 2,000 square feet of inviting ...	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 TRAIL 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%
249 SPARTAN DRIVE Maitland, FL Discover Your Perfect Maitland Retreat! Tucked away on a quiet dead-end street, this deli...	4 beds \| 2 baths \| 1,579 sq.ft.	$345,000	Airbnb cash on cash: 9.75% Traditional cash on cash: 4.51% Airbnb Rental Income: $5007 Traditional Rental Income: $2287 Airbnb ROI: 9.75% Traditional ROI: 4.51%
631 LAKE CATHERINE DRIVE 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%
214 CHERRYWOOD DRIVE Maitland, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	3 beds \| 2 baths \| 1,178 sq.ft.	$335,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 4.91% Airbnb Rental Income: $3440 Traditional Rental Income: $2281 Airbnb ROI: 6.17% Traditional ROI: 4.91%
135 Roosevelt Place Maitland, FL This charming home boasts a wealth of valuable upgrades and improvements, making it an ent...	4 beds \| 2 baths \| 2,426 sq.ft.	$564,900	Airbnb cash on cash: 5.37% Traditional cash on cash: 2.67% Airbnb Rental Income: $5007 Traditional Rental Income: $2560 Airbnb ROI: 5.37% Traditional ROI: 2.67%
113 GEM LAKE DRIVE Maitland, FL Must remodel this 1939 home that was moved from Park Avenue many years ago but now rests i...	3 beds \| 2 baths \| 1,538 sq.ft.	$575,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.05% Airbnb Rental Income: $3440 Traditional Rental Income: $2328 Airbnb ROI: 3.7% Traditional ROI: 3.05%
1511 E HORATIO AVENUE Maitland, FL Welcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, ...	4 beds \| 3 baths \| 2,676 sq.ft.	$699,900	Airbnb cash on cash: 4.09% Traditional cash on cash: 3.44% Airbnb Rental Income: $5007 Traditional Rental Income: $3559 Airbnb ROI: 4.09% Traditional ROI: 3.44%
1231 SIDCUP ROAD 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.	$540,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 4% Airbnb Rental Income: $3440 Traditional Rental Income: $2775 Airbnb ROI: 3.81% Traditional ROI: 4%
380 BANYAN DRIVE Maitland, FL Under contract-accepting backup offers. Charming 3BR/2BA Home with Updated Interior Thi...	3 beds \| 2 baths \| 1,404 sq.ft.	$429,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 3.61% Airbnb Rental Income: $3440 Traditional Rental Income: $2055 Airbnb ROI: 5.16% Traditional ROI: 3.61%
255 W GEORGE AVENUE 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 LANE Maitland, FL Motivated Seller! Stunningly Renovated 4-Bedroom Home in Prime Maitland Seize this rare op...	4 beds \| 2 baths \| 1,664 sq.ft.	$424,900	Airbnb cash on cash: 8.41% Traditional cash on cash: 4.41% Airbnb Rental Income: $5007 Traditional Rental Income: $2394 Airbnb ROI: 8.41% Traditional ROI: 4.41%
2632 DERBYSHIRE ROAD Maitland, FL 2025 ROOF \| POOL HOME Start your new life to one of Orlando's most prestigious sub...	4 beds \| 2 baths \| 1,770 sq.ft.	$555,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 3.43% Airbnb Rental Income: $5007 Traditional Rental Income: $2807 Airbnb ROI: 5.7% Traditional ROI: 3.43%
1135 THUNDER TRAIL Maitland, FL Under contract-accepting backup offers. Distinctive Dommerich Hills Home with Flexible Flo...	4 beds \| 4 baths \| 2,651 sq.ft.	$619,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 6.63% Airbnb Rental Income: $5007 Traditional Rental Income: $5002 Airbnb ROI: 4.87% Traditional ROI: 6.63%
736 FOREST GLEN COURT Maitland, FL One or more photo(s) has been virtually staged. New Price - Motivated Seller!! Welcome to ...	4 beds \| 2 baths \| 1,647 sq.ft.	$479,899	Airbnb cash on cash: 6.62% Traditional cash on cash: 3.56% Airbnb Rental Income: $5007 Traditional Rental Income: $2614 Airbnb ROI: 6.62% Traditional ROI: 3.56%
2155 FENNELL STREET Maitland, FL Back to Market -This is a three-bedroom two-bathroom pool house well located that needs so...	3 beds \| 2 baths \| 1,822 sq.ft.	$395,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 5.11% Airbnb Rental Income: $3440 Traditional Rental Income: $2589 Airbnb ROI: 5.35% Traditional ROI: 5.11%
449 FORESTWOOD LANE Maitland, FL Under contract-accepting backup offers. âBack on the market due to buyer financing. No f...	4 beds \| 2 baths \| 2,532 sq.ft.	$550,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 3.37% Airbnb Rental Income: $5007 Traditional Rental Income: $3068 Airbnb ROI: 5.15% Traditional ROI: 3.37%
1024 KEWANNEE TRAIL Maitland, FL One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed ...	4 beds \| 3 baths \| 1,845 sq.ft.	$624,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 2.96% Airbnb Rental Income: $5007 Traditional Rental Income: $3187 Airbnb ROI: 4.33% Traditional ROI: 2.96%
1074 HAMLET DRIVE 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 One or more photo(s) has been virtually staged. You know it is your house as you walk on y...	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 Auction Property. Welcome to this inviting home offering comfortable living spaces and a t...	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%
2514 TUSCARORA TRAIL Maitland, FL Welcome Home to Your Private Lakeside Oasis! ? Step into the lifestyle youâve been drea...	4 beds \| 3 baths \| 3,000 sq.ft.	$849,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 3.62% Airbnb Rental Income: $5007 Traditional Rental Income: $4131 Airbnb ROI: 3.43% Traditional ROI: 3.62%
1416 CARING COURT Maitland, FL Beautifully maintained Maitland home in the gated community of Montacino on Lake Charity. ...	4 beds \| 4 baths \| 3,451 sq.ft.	$925,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 2.04% Airbnb Rental Income: $5007 Traditional Rental Income: $4083 Airbnb ROI: 1.92% Traditional ROI: 2.04%
421 ARAPAHO TRAIL Maitland, FL Welcome to this charming, move-in ready home nestled in the desirable, family-friendly Dom...	3 beds \| 2 baths \| 1,813 sq.ft.	$779,500	Airbnb cash on cash: 1.84% Traditional cash on cash: 1.99% Airbnb Rental Income: $3440 Traditional Rental Income: $2782 Airbnb ROI: 1.84% Traditional ROI: 1.99%
314 BANYAN DRIVE 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%
735 GAMEWELL AVENUE Maitland, FL Under contract-accepting backup offers. COZY, 2 bedroom, 1 bath, 1 car garage home with a ...	2 beds \| 1 baths \| 938 sq.ft.	$330,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 3.65% Airbnb Rental Income: $2379 Traditional Rental Income: $1662 Airbnb ROI: 4.08% Traditional ROI: 3.65%
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%
6 BARNARD COURT Maitland, FL Under contract-accepting backup offers. Step into timeless style with this completely upda...	3 beds \| 2 baths \| 1,521 sq.ft.	$419,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.82% Airbnb Rental Income: $3440 Traditional Rental Income: $2669 Airbnb ROI: 4.85% Traditional ROI: 4.82%
2525 NATIVE COURT Maitland, FL One or more photo(s) has been virtually staged. Welcome Home!Donât miss this fabulous op...	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%
10 MINNEHAHA CIRCLE Maitland, FL Welcome to this beautifully refined 4-bedroom, 3-bath POOL HOME in the highly sought-after...	4 beds \| 3 baths \| 1,995 sq.ft.	$679,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 3.39% Airbnb Rental Income: $5007 Traditional Rental Income: $3355 Airbnb ROI: 4.38% Traditional ROI: 3.39%
221 WHITE OAK CIRCLE Maitland, FL One or more photo(s) has been virtually staged. Stately brick home in a premier Maitland n...	4 beds \| 2 baths \| 2,500 sq.ft.	$869,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 2.22% Airbnb Rental Income: $5007 Traditional Rental Income: $3105 Airbnb ROI: 3.3% Traditional ROI: 2.22%
633 MAGNOLIA DRIVE 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.	$380,000	Airbnb cash on cash: 5.86% Traditional cash on cash: 4.78% Airbnb Rental Income: $3440 Traditional Rental Income: $2295 Airbnb ROI: 5.86% Traditional ROI: 4.78%
2167 MOHAWK TRAIL Maitland, FL One or more photo(s) has been virtually staged. Celebrate the holidays in this charming 3 ...	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%
2133 FALKNER ROAD Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Di...	4 beds \| 3 baths \| 1,779 sq.ft.	$459,900	Airbnb cash on cash: 7.36% Traditional cash on cash: 4.2% Airbnb Rental Income: $5007 Traditional Rental Income: $2622 Airbnb ROI: 7.36% Traditional ROI: 4.2%
105 TANGELO COURT Maitland, FL Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positio...	5 beds \| 5 baths \| 3,203 sq.ft.	$1,799,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 2.49% Airbnb Rental Income: $5533 Traditional Rental Income: $6553 Airbnb ROI: 1.21% Traditional ROI: 2.49%
620 CHICKAPEE TRAIL Maitland, FL Under contract-accepting backup offers. Discover the charm of Mid-Century Modern living in...	4 beds \| 2 baths \| 1,910 sq.ft.	$525,000	Airbnb cash on cash: 6.51% Traditional cash on cash: 4.23% Airbnb Rental Income: $5007 Traditional Rental Income: $2867 Airbnb ROI: 6.51% Traditional ROI: 4.23%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Maitland, FL

195 E FAITH TERRACE

Maitland, FL

3 beds | 2 baths | 2,502 sq.ft.

$825,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 1.65%

Airbnb Rental Income: $3440

Traditional Rental Income: $2737

Airbnb ROI: 1.58%

Traditional ROI: 1.65%

515 W FAITH TERRACE

Maitland, FL

3 beds | 2 baths | 2,205 sq.ft.

$515,000

Airbnb cash on cash: 3.4%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $3440

Traditional Rental Income: $3030

Airbnb ROI: 3.4%

Traditional ROI: 4.13%

1655 SUNNYSIDE DRIVE

Maitland, FL

3 beds | 2 baths | 1,418 sq.ft.

$699,000

Airbnb cash on cash: 1.59%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $3440

Traditional Rental Income: $2319

Airbnb ROI: 1.59%

Traditional ROI: 1.04%

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 TRAIL

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%

249 SPARTAN DRIVE

Maitland, FL

4 beds | 2 baths | 1,579 sq.ft.

$345,000

Airbnb cash on cash: 9.75%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $5007

Traditional Rental Income: $2287

Airbnb ROI: 9.75%

Traditional ROI: 4.51%

631 LAKE CATHERINE DRIVE

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%

214 CHERRYWOOD DRIVE

Maitland, FL

3 beds | 2 baths | 1,178 sq.ft.

$335,000

Airbnb cash on cash: 6.17%

Traditional cash on cash: 4.91%

Airbnb Rental Income: $3440

Traditional Rental Income: $2281

Airbnb ROI: 6.17%