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 43 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
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%
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%
354 HICKORY DRIVE Maitland, FL Welcome Home to 354 Hickory Drive â Where Your Next Chapter Begins! Nestled in the frie...	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%
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%
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%
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%
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%
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%
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%
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%
1256 WELLINGTON TERRACE Maitland, FL HARD TO FIND SKI LAKEFRONT! Classic traditional beauty â ready for a lucky buyer to mak...	5 beds \| 5 baths \| 4,280 sq.ft.	$1,390,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 3.22% Airbnb Rental Income: $5533 Traditional Rental Income: $6803 Airbnb ROI: 1.38% Traditional ROI: 3.22%
1111 AUDUBON WAY Maitland, FL Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitlandâs most desi...	4 beds \| 4 baths \| 3,754 sq.ft.	$1,975,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 1.53% Airbnb Rental Income: $5007 Traditional Rental Income: $6014 Airbnb ROI: 0.43% Traditional ROI: 1.53%
250 ORANGE PLACE Maitland, FL Welcome to 250 Orange Place, This charming bungalow in an unbeatable location just two blo...	1 beds \| 1 baths \| 564 sq.ft.	$325,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.17% Airbnb Rental Income: $1832 Traditional Rental Income: $1729 Airbnb ROI: 1.89% Traditional ROI: 3.17%
570 DOMMERICH DRIVE Maitland, FL One or more photo(s) has been virtually staged. ONE OF A KIND for Dommerich Estates, this ...	4 beds \| 3 baths \| 2,956 sq.ft.	$975,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 3.49% Airbnb Rental Income: $5007 Traditional Rental Income: $4675 Airbnb ROI: 2.72% Traditional ROI: 3.49%
1741 LYNDALE BOULEVARD Maitland, FL Charming Newly Renovated Bungalow in Prime Maitland Location â Move-In Ready with Endles...	3 beds \| 2 baths \| 1,495 sq.ft.	$739,990	Airbnb cash on cash: 1.78% Traditional cash on cash: 1.71% Airbnb Rental Income: $3440 Traditional Rental Income: $2634 Airbnb ROI: 1.78% Traditional ROI: 1.71%
220 ALPINE DRIVE Maitland, FL Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same fami...	2 beds \| 1 baths \| 988 sq.ft.	$450,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 2.7% Airbnb Rental Income: $2379 Traditional Rental Income: $2166 Airbnb ROI: 1.82% Traditional ROI: 2.7%
1817 BRAELOCH COURT Maitland, FL Under contract-accepting backup offers. Welcome to this stunning home in Maitland, located...	4 beds \| 3 baths \| 2,872 sq.ft.	$974,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 2.29% Airbnb Rental Income: $5007 Traditional Rental Income: $3658 Airbnb ROI: 2.65% Traditional ROI: 2.29%
535 PAWNEE TRAIL Maitland, FL Welcome to your dream home! This beautifully updated 4-bedroom, 3 bath residence is in one...	4 beds \| 3 baths \| 2,500 sq.ft.	$918,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 2.94% Airbnb Rental Income: $5007 Traditional Rental Income: $4422 Airbnb ROI: 2.43% Traditional ROI: 2.94%
106 OAKWOOD DRIVE Maitland, FL One or more photo(s) has been virtually staged. MAJOR PRICE IMPROVEMENT Fully reimagined d...	3 beds \| 2 baths \| 1,877 sq.ft.	$649,900	Airbnb cash on cash: 2.96% Traditional cash on cash: 3.68% Airbnb Rental Income: $3440 Traditional Rental Income: $3114 Airbnb ROI: 2.96% Traditional ROI: 3.68%
150 SENECA TRAIL Maitland, FL Under contract-accepting backup offers. In the heart of Dommerich, this thoughtfully renov...	4 beds \| 3 baths \| 2,221 sq.ft.	$745,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 1.93% Airbnb Rental Income: $5007 Traditional Rental Income: $3113 Airbnb ROI: 3.18% Traditional ROI: 1.93%
623 GREEN MEADOW AVENUE Maitland, FL Welcome to this two-owner concrete block home offering the perfect blend of comfort, chara...	4 beds \| 2 baths \| 1,909 sq.ft.	$570,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 4.61% Airbnb Rental Income: $5007 Traditional Rental Income: $3272 Airbnb ROI: 5.94% Traditional ROI: 4.61%
1750 POCAHONTAS PATH Maitland, FL Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,9...	3 beds \| 2 baths \| 1,922 sq.ft.	$679,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 2.76% Airbnb Rental Income: $3440 Traditional Rental Income: $2871 Airbnb ROI: 2.46% Traditional ROI: 2.76%
2600 MOHAWK TRAIL Maitland, FL Dommerich Hills â Maitland Positioned in the heart of Maitland, this inviting single-...	4 beds \| 3 baths \| 2,265 sq.ft.	$669,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 4.44% Airbnb Rental Income: $5007 Traditional Rental Income: $3768 Airbnb ROI: 4.78% Traditional ROI: 4.44%
210 ALPINE DRIVE Maitland, FL Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for ...	2 beds \| 2 baths \| 1,328 sq.ft.	$550,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 2.29% Airbnb Rental Income: $2379 Traditional Rental Income: $2439 Airbnb ROI: 1.04% Traditional ROI: 2.29%
1241 Manchester Road Maitland, FL Step into this beautifully renovated 4-bedroom, 2-bathroom home located in the heart of Ma...	4 beds \| 2 baths \| 2,038 sq.ft.	$625,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.04% Airbnb Rental Income: $5007 Traditional Rental Income: $2844 Airbnb ROI: 4.99% Traditional ROI: 3.04%
551 RUFFEL STREET Maitland, FL Situated at the end of a cul-de-sac in the Eatonville/Maitland area, this home offers a gr...	3 beds \| 2 baths \| 1,162 sq.ft.	$304,999	Airbnb cash on cash: 7.87% Traditional cash on cash: 6.79% Airbnb Rental Income: $3440 Traditional Rental Income: $2369 Airbnb ROI: 7.87% Traditional ROI: 6.79%

Your search for investment property begins and ends here

Single Family Homes 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%

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%

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%

Traditional ROI: 3.89%

1665 KING ARTHUR CIRCLE

Maitland, FL

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

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%