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.

Investment Property for Sale in Maitland, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
204 Quayside Cir #504 Maitland, FL 204 Quayside Cir #504, Maitland, FL 32751 \| Condo/Coop	2 beds \| 2 baths \| 1,270 sq.ft.	$458,500	Airbnb cash on cash: -0.37% Traditional cash on cash: -0.75% Airbnb Rental Income: $2379 Traditional Rental Income: $1632 Airbnb ROI: -0.37% Traditional ROI: -0.75%
140 WIGWAM PLACE Maitland, FL One or more photo(s) has been virtually staged. Tucked away on a cul-de-sac in beautiful M...	3 beds \| 3 baths \| 2,236 sq.ft.	$649,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 3.82% Airbnb Rental Income: $3440 Traditional Rental Income: $3387 Airbnb ROI: 2.65% Traditional ROI: 3.82%
1281 Wellington Ter Maitland, FL 1281 Wellington Ter, Maitland, FL 32751 \| Single Family Residential	4 beds \| 3 baths \| 2,931 sq.ft.	$979,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.39% Airbnb Rental Income: $5007 Traditional Rental Income: $3128 Airbnb ROI: 2.33% Traditional ROI: 1.39%
790 S LAKE SYBELIA DRIVE Maitland, FL One or more photo(s) has been virtually staged. Price Improvement! Rare opportunity to own...	3 beds \| 3 baths \| 2,021 sq.ft.	$960,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 2.36% Airbnb Rental Income: $3440 Traditional Rental Income: $3731 Airbnb ROI: 1.18% Traditional ROI: 2.36%
824 TOWN CIRCLE #101 Maitland, FL Move-in ready two story townhome. This beautifully updated 3 bd 2.5 ba corner unit is loca...	3 beds \| 3 baths \| 1,565 sq.ft.	$264,990	Airbnb cash on cash: 6.1% Traditional cash on cash: 4.93% Airbnb Rental Income: $3440 Traditional Rental Income: $2385 Airbnb ROI: 6.1% Traditional ROI: 4.93%
921 N Thistle Ln Maitland, FL So much potential! Located on a premium 1/4 acre lot, this 3 bed/2 bath home is set back f...	4 beds \| 3 baths \| 2,300 sq.ft.	$1,049,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 1.8% Airbnb Rental Income: $5007 Traditional Rental Income: $2999 Airbnb ROI: 2.81% Traditional ROI: 1.8%
350 NORTHWIND ROAD Maitland, FL Under contract-accepting backup offers. Nestled within the 9-acre Lake Maitland Owl Preser...	5 beds \| 5 baths \| 4,819 sq.ft.	$3,100,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.96% Airbnb Rental Income: $5533 Traditional Rental Income: $7429 Airbnb ROI: -0.09% Traditional ROI: 0.96%
448 STONEWOOD LANE Maitland, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-b...	4 beds \| 3 baths \| 3,308 sq.ft.	$624,990	Airbnb cash on cash: 3.82% Traditional cash on cash: 3.8% Airbnb Rental Income: $5007 Traditional Rental Income: $3970 Airbnb ROI: 3.82% Traditional ROI: 3.8%
361 HICKORY DRIVE Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 2 baths \| 1,407 sq.ft.	$349,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 5.46% Airbnb Rental Income: $3440 Traditional Rental Income: $2459 Airbnb ROI: 6.12% Traditional ROI: 5.46%
755 WOODSIDE ROAD Maitland, FL This is the one you've been waiting for- a SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND...	3 beds \| 3 baths \| 3,049 sq.ft.	$999,999	Airbnb cash on cash: 1.12% Traditional cash on cash: 2.04% Airbnb Rental Income: $3440 Traditional Rental Income: $3532 Airbnb ROI: 1.12% Traditional ROI: 2.04%
1140 S Orlando Ave #E-11 Maitland, FL Rare Opportunity for Lakeside Living! This beautifully maintained 1-bedroom, 1-bath, 612 s...	1 beds \| 1 baths \| 612 sq.ft.	$210,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 5.58% Airbnb Rental Income: $1832 Traditional Rental Income: $1564 Airbnb ROI: 4.45% Traditional ROI: 5.58%
354 HICKORY DRIVE Maitland, FL Under contract-accepting backup offers. Multiple offers received, asking for highest and b...	3 beds \| 2 baths \| 1,395 sq.ft.	$375,000	Airbnb cash on cash: 5.58% Traditional cash on cash: 3.89% Airbnb Rental Income: $3440 Traditional Rental Income: $2082 Airbnb ROI: 5.58% Traditional ROI: 3.89%
2525 CAPER LANE #205 Maitland, FL This bright and inviting second floor condo offers an abundance of natural light throughou...	1 beds \| 1 baths \| 550 sq.ft.	$119,000	Airbnb cash on cash: 6.49% Traditional cash on cash: 8.45% Airbnb Rental Income: $1832 Traditional Rental Income: $1563 Airbnb ROI: 6.49% Traditional ROI: 8.45%
1125 Lake Shadow Cir #5211 Maitland, FL Located in the resort style community of VISCONTI WEST, this beautiful 1 bedroom corner un...	1 beds \| 1 baths \| 707 sq.ft.	$160,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 4.92% Airbnb Rental Income: $1832 Traditional Rental Income: $1522 Airbnb ROI: 3.72% Traditional ROI: 4.92%
1665 KING ARTHUR CIRCLE Maitland, FL Under contract-accepting backup offers. 1665 King Arthur Circle	5 beds \| 3 baths \| 3,019 sq.ft.	$1,100,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 1.63% Airbnb Rental Income: $5533 Traditional Rental Income: $3840 Airbnb ROI: 2.19% Traditional ROI: 1.63%
1501 Druid Isle Rd Maitland, FL NEW YEAR, NEW IMPROVED PRICE Dream Lakeside Living in Maitland! 3 Bed \| 2 Bath \| Fully Ren...	3 beds \| 2 baths \| 3,000 sq.ft.	$824,000	Airbnb cash on cash: 1% Traditional cash on cash: 1.8% Airbnb Rental Income: $3440 Traditional Rental Income: $3294 Airbnb ROI: 1% Traditional ROI: 1.8%
200 SPARTAN DRIVE Maitland, FL More photos to come soon! Welcome to 200 Spartan Dr, a beautifully updated 3/2 (with bonus...	3 beds \| 2 baths \| 1,830 sq.ft.	$540,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 3.67% Airbnb Rental Income: $3440 Traditional Rental Income: $3265 Airbnb ROI: 2.51% Traditional ROI: 3.67%
2642 BROOKSIDE COURT Maitland, FL Indulge in the epitome of modern living with this fully renovated masterpiece! Boasting a ...	5 beds \| 2 baths \| 2,360 sq.ft.	$629,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 2.96% Airbnb Rental Income: $5533 Traditional Rental Income: $2974 Airbnb ROI: 5.43% Traditional ROI: 2.96%
612 Green Meadow Ave Maitland, FL Welcome to a home that doesnât just check boxes â it supports your lifestyle. Tucked i...	3 beds \| 2 baths \| 1,707 sq.ft.	$500,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.82% Airbnb Rental Income: $3440 Traditional Rental Income: $2396 Airbnb ROI: 3.43% Traditional ROI: 2.82%
219 Quayside Cir Maitland, FL Under contract-accepting backup offers. Fantastic opportunity to own a condo/townhome unit...	2 beds \| 2 baths \| 1,459 sq.ft.	$895,000	Airbnb cash on cash: -0.87% Traditional cash on cash: -0.81% Airbnb Rental Income: $2379 Traditional Rental Income: $1845 Airbnb ROI: -0.87% Traditional ROI: -0.81%
2150 Tortoise Shell Dr Maitland, FL One or more photo(s) has been virtually staged. Perfect starter home nestled in the heart ...	3 beds \| 2 baths \| 1,512 sq.ft.	$429,900	Airbnb cash on cash: 4.45% Traditional cash on cash: 3.7% Airbnb Rental Income: $3440 Traditional Rental Income: $2378 Airbnb ROI: 4.45% Traditional ROI: 3.7%
1291 OXFORD ROAD Maitland, FL Welcome to this thoughtfully updated one-story home in the established community of Englis...	3 beds \| 2 baths \| 1,370 sq.ft.	$459,000	Airbnb cash on cash: 4.35% Traditional cash on cash: 3.78% Airbnb Rental Income: $3440 Traditional Rental Income: $2434 Airbnb ROI: 4.35% Traditional ROI: 3.78%
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.	$719,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.32% Airbnb Rental Income: $5007 Traditional Rental Income: $3559 Airbnb ROI: 3.95% Traditional ROI: 3.32%
1230 Hollyridge Trl Maitland, FL Under contract-accepting backup offers. *** Unique private paradise in Dommerich â back ...	3 beds \| 2 baths \| 1,641 sq.ft.	$534,900	Airbnb cash on cash: 3.82% Traditional cash on cash: 3.6% Airbnb Rental Income: $3440 Traditional Rental Income: $2567 Airbnb ROI: 3.82% Traditional ROI: 3.6%
385 Lime St Maitland, FL Wonderful investment opportunity in historic Eatonville. Large corner lot. Roof was replac...	4 beds \| N/A baths \| 1,680 sq.ft.	$419,900	Airbnb cash on cash: 4.89% Traditional cash on cash: 4.19% Airbnb Rental Income: $3440 Traditional Rental Income: $2401 Airbnb ROI: 4.89% Traditional ROI: 4.19%
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.	$549,750	Airbnb cash on cash: 5.04% Traditional cash on cash: 3.45% Airbnb Rental Income: $5007 Traditional Rental Income: $3169 Airbnb ROI: 5.04% Traditional ROI: 3.45%
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: 5.91% Airbnb Rental Income: $3440 Traditional Rental Income: $2262 Airbnb ROI: 7.35% Traditional ROI: 5.91%
2514 Tuscarora Trl Maitland, FL Welcome Home to Your Private Lakeside Oasis! ? Step into the lifestyle youâve been drea...	4 beds \| 2 baths \| 3,000 sq.ft.	$745,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 3.53% Airbnb Rental Income: $5007 Traditional Rental Income: $3645 Airbnb ROI: 4.02% Traditional ROI: 3.53%
1275 LAKE SHADOW CIRCLE #13107 Maitland, FL Welcome home to this truly move-in-ready, beautifully updated 1-bedroom, 1-bath ground-flo...	1 beds \| 1 baths \| 672 sq.ft.	$179,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 4.54% Airbnb Rental Income: $1832 Traditional Rental Income: $1693 Airbnb ROI: 2.47% Traditional ROI: 4.54%
225 QUAYSIDE CIRCLE Maitland, FL Under contract-accepting backup offers. Discover the perfect blend of style and location i...	3 beds \| 3 baths \| 1,734 sq.ft.	$560,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.56% Airbnb Rental Income: $3440 Traditional Rental Income: $2698 Airbnb ROI: 1.52% Traditional ROI: 1.56%
1732 Ridgewood Ave #S Maitland, FL This custom two-story townhome delivers what most properties in this category simply donâ...	3 beds \| 3 baths \| 2,407 sq.ft.	$725,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.14% Airbnb Rental Income: $3440 Traditional Rental Income: $3935 Airbnb ROI: 1.28% Traditional ROI: 3.14%
223 Quayside Cir #C Maitland, FL Welcome to refined living in The Moorings! This beautifully updated 3-bedroom, 2.5-bath to...	3 beds \| 2 baths \| 1,734 sq.ft.	$575,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 1.28% Airbnb Rental Income: $3440 Traditional Rental Income: $2687 Airbnb ROI: 1.26% Traditional ROI: 1.28%
353 W Lake Faith Dr #116 Maitland, FL Discover lakeside living at its finest in this beautifully updated 2nd-floor, private lake...	2 beds \| 2 baths \| 1,403 sq.ft.	$344,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 3.89% Airbnb Rental Income: $2379 Traditional Rental Income: $2485 Airbnb ROI: 1.76% Traditional ROI: 3.89%
105 Tangelo Ct Maitland, FL Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positio...	5 beds \| 4 baths \| 3,203 sq.ft.	$1,798,999	Airbnb cash on cash: 1.21% Traditional cash on cash: 1.73% Airbnb Rental Income: $5533 Traditional Rental Income: $5285 Airbnb ROI: 1.21% Traditional ROI: 1.73%
2065 DERBYSHIRE ROAD Maitland, FL Under contract-accepting backup offers. Beautifully renovated and move-in ready, this 3-be...	3 beds \| 2 baths \| 1,430 sq.ft.	$449,990	Airbnb cash on cash: 4.78% Traditional cash on cash: 4.39% Airbnb Rental Income: $3440 Traditional Rental Income: $2510 Airbnb ROI: 4.78% Traditional ROI: 4.39%
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.	$1,130,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.75% Airbnb Rental Income: $5007 Traditional Rental Income: $3379 Airbnb ROI: 2.33% Traditional ROI: 1.75%
1033 Hamlet Dr Maitland, FL 1033 Hamlet Dr, Maitland, FL 32751 \| Single Family Residential	3 beds \| 2 baths \| 1,146 sq.ft.	$350,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 3.98% Airbnb Rental Income: $3440 Traditional Rental Income: $2078 Airbnb ROI: 5.81% Traditional ROI: 3.98%
1325 LAKE SHADOW CIRCLE #12202 Maitland, FL HUGE PRICE REDUCTION Step into effortless living with this beautifully maintained 2-bed...	2 beds \| 2 baths \| 1,111 sq.ft.	$199,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 5.38% Airbnb Rental Income: $2379 Traditional Rental Income: $1999 Airbnb ROI: 4.3% Traditional ROI: 5.38%
1100 S Orlando Ave #956 Maitland, FL LAKEFRONT - Enjoy condo living at its finest from the top-floor Lake Maitland penthouse wi...	2 beds \| 2 baths \| 1,685 sq.ft.	$795,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 0.47% Airbnb Rental Income: $2379 Traditional Rental Income: $2953 Airbnb ROI: -1.09% Traditional ROI: 0.47%
2453 Worthington Rd Maitland, FL 2453 Worthington Rd, Maitland, FL 32751 \| Single Family Residential	4 beds \| 2 baths \| 1,959 sq.ft.	$585,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 2.7% Airbnb Rental Income: $5007 Traditional Rental Income: $2598 Airbnb ROI: 5.24% Traditional ROI: 2.7%

Real Estate investment in Maitland, FL

There are 119 properties for sale in the city of Maitland . The median list price in Maitland is $555,000 and the average price per square foot is $262. In May 2026, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,485.

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

There are 119 investment properties available for sale in Maitland.

In 2026, the best neighborhood to buy investment property is Maitland.

The ROI for Short-Term is higher than the Long-Term in Maitland with average rental income of $3,440.

Your search for investment property begins and ends here

Investment Property for Sale in Maitland, FL

204 Quayside Cir #504

Maitland, FL

2 beds | 2 baths | 1,270 sq.ft.

$458,500

Airbnb cash on cash: -0.37%

Traditional cash on cash: -0.75%

Airbnb Rental Income: $2379

Traditional Rental Income: $1632

Airbnb ROI: -0.37%

Traditional ROI: -0.75%

140 WIGWAM PLACE

Maitland, FL

3 beds | 3 baths | 2,236 sq.ft.

$649,900

Airbnb cash on cash: 2.65%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $3440

Traditional Rental Income: $3387

Airbnb ROI: 2.65%

Traditional ROI: 3.82%

1281 Wellington Ter

Maitland, FL

4 beds | 3 baths | 2,931 sq.ft.

$979,000

Airbnb cash on cash: 2.33%

Traditional cash on cash: 1.39%

Airbnb Rental Income: $5007

Traditional Rental Income: $3128

Airbnb ROI: 2.33%

Traditional ROI: 1.39%

790 S LAKE SYBELIA DRIVE

Maitland, FL

3 beds | 3 baths | 2,021 sq.ft.

$960,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $3440

Traditional Rental Income: $3731

Airbnb ROI: 1.18%

Traditional ROI: 2.36%

824 TOWN CIRCLE #101

Maitland, FL

3 beds | 3 baths | 1,565 sq.ft.

$264,990

Airbnb cash on cash: 6.1%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $3440

Traditional Rental Income: $2385

Airbnb ROI: 6.1%

Traditional ROI: 4.93%

921 N Thistle Ln

Maitland, FL

4 beds | 3 baths | 2,300 sq.ft.

$1,049,000

Airbnb cash on cash: 2.81%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $5007

Traditional Rental Income: $2999

Airbnb ROI: 2.81%

Traditional ROI: 1.8%

350 NORTHWIND ROAD

Maitland, FL

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

$3,100,000

Airbnb cash on cash: -0.09%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $5533

Traditional Rental Income: $7429

Airbnb ROI: -0.09%

Traditional ROI: 0.96%

448 STONEWOOD LANE

Maitland, FL

4 beds | 3 baths | 3,308 sq.ft.

$624,990

Airbnb cash on cash: 3.82%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $5007

Traditional Rental Income: $3970

Airbnb ROI: 3.82%