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
790 S LAKE SYBELIA DRIVE Maitland, FL One or more photo(s) has been virtually staged. Rare opportunity to own a private 0.66-acr...	3 beds \| 3 baths \| 2,021 sq.ft.	$975,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 2.31% Airbnb Rental Income: $3440 Traditional Rental Income: $3731 Airbnb ROI: 1.15% Traditional ROI: 2.31%
350 NORTHWIND ROAD Maitland, FL Nestled within the 9-acre Lake Maitland Owl Preserve, this striking contemporary residence...	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.	$605,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 3.95% Airbnb Rental Income: $5007 Traditional Rental Income: $3970 Airbnb ROI: 3.98% Traditional ROI: 3.95%
361 HICKORY DRIVE Maitland, FL One or more photo(s) has been virtually staged. Welcome to 361 Hickory Drive, a truly spec...	3 beds \| 2 baths \| 1,407 sq.ft.	$369,000	Airbnb cash on cash: 5.74% Traditional cash on cash: 5.11% Airbnb Rental Income: $3440 Traditional Rental Income: $2459 Airbnb ROI: 5.74% Traditional ROI: 5.11%
206 QUAYSIDE CIRCLE #103 Maitland, FL Under contract-accepting backup offers. Luxury lakefront living at its finest awaits at "T...	2 beds \| 2 baths \| 1,270 sq.ft.	$720,000	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.39% Airbnb Rental Income: $2379 Traditional Rental Income: $2015 Airbnb ROI: -0.72% Traditional ROI: -0.39%
830 FAITH STREET Maitland, FL Under contract-accepting backup offers. Beautifully renovated 3-bedroom, 2-bathroom home f...	3 beds \| 2 baths \| 1,577 sq.ft.	$525,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 2.64% Airbnb Rental Income: $3440 Traditional Rental Income: $2518 Airbnb ROI: 2.97% Traditional ROI: 2.64%
1140 South Orlando Avenue #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 Multiple offers received, asking for highest and best before Sunday, April 19th at 5pm! We...	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%
1665 KING ARTHUR CIRCLE Maitland, FL Under contract-accepting backup offers. 1665 King Arthur Circle	4 beds \| 3 baths \| 3,019 sq.ft.	$1,100,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 1.63% Airbnb Rental Income: $5007 Traditional Rental Income: $3840 Airbnb ROI: 1.77% Traditional ROI: 1.63%
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 ...	4 beds \| 2 baths \| 2,360 sq.ft.	$640,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.9% Airbnb Rental Income: $5007 Traditional Rental Income: $2974 Airbnb ROI: 4.59% Traditional ROI: 2.9%
1662 BOBTAIL DRIVE Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	5 beds \| 3 baths \| 2,398 sq.ft.	$525,000	Airbnb cash on cash: 6.7% Traditional cash on cash: 3.77% Airbnb Rental Income: $5533 Traditional Rental Income: $2983 Airbnb ROI: 6.7% Traditional ROI: 3.77%
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%
1994 KENASTON ROAD #1994 Maitland, FL Located in the desirable city of Maitland, just three miles from Winter Parkâs renowned ...	3 beds \| 4 baths \| 2,103 sq.ft.	$415,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 7.11% Airbnb Rental Income: $3440 Traditional Rental Income: $3671 Airbnb ROI: 4.55% Traditional ROI: 7.11%
1231 SIDCUP ROAD Maitland, FL Under contract-accepting backup offers. Prepare to be captivated by this fully renovated g...	3 beds \| 2 baths \| 1,798 sq.ft.	$495,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 5.34% Airbnb Rental Income: $3440 Traditional Rental Income: $3189 Airbnb ROI: 4.24% Traditional ROI: 5.34%
206 QUAYSIDE CIRCLE #404 Maitland, FL Welcome to The Moorings, a rarely available lakeside community perfectly positioned across...	2 beds \| 2 baths \| 1,270 sq.ft.	$570,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 1.82% Airbnb Rental Income: $2379 Traditional Rental Income: $2378 Airbnb ROI: 0.72% Traditional ROI: 1.82%
2329 SHADOW VIEW CIRCLE #2329 Maitland, FL Welcome to this stunning, fully renovated 3-Bedroom, 2.5-Bath home located in the desirab...	3 beds \| 3 baths \| 1,583 sq.ft.	$320,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 3.81% Airbnb Rental Income: $3440 Traditional Rental Income: $2485 Airbnb ROI: 4.45% Traditional ROI: 3.81%
385 LIME STREET 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%
1913 POINSETTA LANE Maitland, FL Priced to Sell \| Renovated Pool Home in Prime Maitland Location This thoughtfully refreshe...	4 beds \| 2 baths \| 1,664 sq.ft.	$399,900	Airbnb cash on cash: 8.99% Traditional cash on cash: 5.94% Airbnb Rental Income: $5007 Traditional Rental Income: $2841 Airbnb ROI: 8.99% Traditional ROI: 5.94%
1000 KEWANNEE TRAIL Maitland, FL Under contract-accepting backup offers. WELCOME TO YOUR DOMMERICH HOME - This tastefully ...	3 beds \| 2 baths \| 2,044 sq.ft.	$650,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 3.05% Airbnb Rental Income: $3440 Traditional Rental Income: $2962 Airbnb ROI: 2.59% Traditional ROI: 3.05%
1400 LAKE SHADOW CIRCLE #10104 Maitland, FL One or more photo(s) has been virtually staged. One or more photo(s) has been virtually st...	1 beds \| 1 baths \| 672 sq.ft.	$148,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 4.87% Airbnb Rental Income: $1832 Traditional Rental Income: $1579 Airbnb ROI: 3.16% Traditional ROI: 4.87%
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 DRIVE Maitland, FL Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, ...	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%
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 Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2....	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 AVENUE #S Maitland, FL This custom two-story townhome delivers what most properties in this category simply donâ...	3 beds \| 4 baths \| 2,407 sq.ft.	$749,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 3.01% Airbnb Rental Income: $3440 Traditional Rental Income: $3935 Airbnb ROI: 1.21% Traditional ROI: 3.01%
223 QUAYSIDE CIRCLE #C Maitland, FL Welcome to refined living in The Moorings! This beautifully updated 3-bedroom, 2.5-bath to...	3 beds \| 3 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 DRIVE #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.	$349,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 3.88% Airbnb Rental Income: $2379 Traditional Rental Income: $2485 Airbnb ROI: 1.78% Traditional ROI: 3.88%
2065 DERBYSHIRE ROAD 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.	$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 LANE 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 SELLER MOTIVATED Welcome to this beautifully maintained 2-bedroom, 2-bath condominium of...	2 beds \| 2 baths \| 1,111 sq.ft.	$215,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 4.92% Airbnb Rental Income: $2379 Traditional Rental Income: $1999 Airbnb ROI: 3.91% Traditional ROI: 4.92%
1100 S ORLANDO AVENUE #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%
2466 FIELDINGWOOD ROAD Maitland, FL Welcome to 2466 Fieldingwood Rd, a fully re-imagined pool home in Maitland, FL. This 4 ...	4 beds \| 2 baths \| 1,765 sq.ft.	$599,000	Airbnb cash on cash: 5.67% Traditional cash on cash: 3.52% Airbnb Rental Income: $5007 Traditional Rental Income: $2778 Airbnb ROI: 5.67% Traditional ROI: 3.52%
1130 MECHANIC STREET Maitland, FL Pre-Construction. To be built. Come build your dream home on this exceptional homesite in ...	4 beds \| 5 baths \| 3,567 sq.ft.	$1,800,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.51% Airbnb Rental Income: $5007 Traditional Rental Income: $7698 Airbnb ROI: 1.29% Traditional ROI: 3.51%
2570 DERBYSHIRE BOULEVARD Maitland, FL One or more photo(s) has been virtually staged. Welcome to 2570 Derbyshire Blvd, a fully t...	4 beds \| 3 baths \| 1,857 sq.ft.	$555,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 5.01% Airbnb Rental Income: $5007 Traditional Rental Income: $3387 Airbnb ROI: 6.16% Traditional ROI: 5.01%
312 MACARTHUR PLACE Maitland, FL Under contract-accepting backup offers. NEW ROOF, NEWER AC, and NO HOAâthis beautifully ...	3 beds \| 3 baths \| 2,441 sq.ft.	$774,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 2.5% Airbnb Rental Income: $3440 Traditional Rental Income: $3451 Airbnb ROI: 1.43% Traditional ROI: 2.5%
2004 MICHAEL TIAGO CIRCLE Maitland, FL Beautifully maintained 3-bedroom, 2-bathroom home offering 2,167 square feet of heated liv...	3 beds \| 3 baths \| 2,167 sq.ft.	$430,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 4.27% Airbnb Rental Income: $3440 Traditional Rental Income: $3174 Airbnb ROI: 3.04% Traditional ROI: 4.27%
51 OAKLEIGH LANE Maitland, FL Come see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comf...	4 beds \| 4 baths \| 4,149 sq.ft.	$1,240,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 2.98% Airbnb Rental Income: $5007 Traditional Rental Income: $5195 Airbnb ROI: 1.93% Traditional ROI: 2.98%

Real Estate investment in Maitland, FL

There are 65 properties for sale in the city of Maitland . The median list price in Maitland is $549,750 and the average price per square foot is $295. In April 2026, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,693.

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

There are 65 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

790 S LAKE SYBELIA DRIVE

Maitland, FL

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

$975,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 2.31%

Airbnb Rental Income: $3440

Traditional Rental Income: $3731

Airbnb ROI: 1.15%

Traditional ROI: 2.31%

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.

$605,000

Airbnb cash on cash: 3.98%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $5007

Traditional Rental Income: $3970

Airbnb ROI: 3.98%

Traditional ROI: 3.95%

361 HICKORY DRIVE

Maitland, FL

3 beds | 2 baths | 1,407 sq.ft.

$369,000

Airbnb cash on cash: 5.74%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $3440

Traditional Rental Income: $2459

Airbnb ROI: 5.74%

Traditional ROI: 5.11%

206 QUAYSIDE CIRCLE #103

Maitland, FL

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

$720,000

Airbnb cash on cash: -0.72%

Traditional cash on cash: -0.39%

Airbnb Rental Income: $2379

Traditional Rental Income: $2015

Airbnb ROI: -0.72%

Traditional ROI: -0.39%

830 FAITH STREET

Maitland, FL

3 beds | 2 baths | 1,577 sq.ft.

$525,000

Airbnb cash on cash: 2.97%

Traditional cash on cash: 2.64%

Airbnb Rental Income: $3440

Traditional Rental Income: $2518

Airbnb ROI: 2.97%

Traditional ROI: 2.64%

1140 South Orlando Avenue #E-11

Maitland, FL

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

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%