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 64 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
140 Wigwam Pl Maitland, FL Virtually Staged. Tucked away on a cul-de-sac in beautiful Maitland, this 3-bedroom, 3-bat...	3 beds \| 3 baths \| 2,236 sq.ft.	$599,900	Airbnb cash on cash: 1.65% Traditional cash on cash: 4.05% Airbnb Rental Income: $2620 Traditional Rental Income: $3387 Airbnb ROI: 1.65% Traditional ROI: 4.05%
766 TERRA PLACE Maitland, FL Under contract-accepting backup offers. Virtually Staged. Private Pool Retreat with Two Pr...	4 beds \| 5 baths \| 3,040 sq.ft.	$1,149,900	Airbnb cash on cash: 1.49% Traditional cash on cash: 4.39% Airbnb Rental Income: $4486 Traditional Rental Income: $6658 Airbnb ROI: 1.49% Traditional ROI: 4.39%
448 Stonewood Ln 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.	$599,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 3.8% Airbnb Rental Income: $4486 Traditional Rental Income: $3970 Airbnb ROI: 3.08% Traditional ROI: 3.8%
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.	$975,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 2.12% Airbnb Rental Income: $2620 Traditional Rental Income: $3532 Airbnb ROI: 0.42% Traditional ROI: 2.12%
220 Adams Dr Maitland, FL Welcome to 220 Adams Drive â a breathtaking, completely remodeled single-story masterpie...	4 beds \| 3 baths \| 3,005 sq.ft.	$1,995,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.75% Airbnb Rental Income: $4486 Traditional Rental Income: $4773 Airbnb ROI: 0.09% Traditional ROI: 0.75%
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.	$1,795,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.61% Airbnb Rental Income: $2620 Traditional Rental Income: $3869 Airbnb ROI: -0.52% Traditional ROI: 0.61%
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: 4.53% Traditional cash on cash: 2.96% Airbnb Rental Income: $4897 Traditional Rental Income: $2974 Airbnb ROI: 4.53% Traditional ROI: 2.96%
612 GREEN MEADOW AVENUE Maitland, FL Under contract-accepting backup offers. Welcome to a home that doesnât just check boxes ...	3 beds \| 2 baths \| 1,707 sq.ft.	$490,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 2.9% Airbnb Rental Income: $2620 Traditional Rental Income: $2396 Airbnb ROI: 2.02% Traditional ROI: 2.9%
1511 E Horatio Ave 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.	$698,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 3.32% Airbnb Rental Income: $4486 Traditional Rental Income: $3559 Airbnb ROI: 3.3% Traditional ROI: 3.32%
2697 QUEEN MARY PLACE Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	3 beds \| 2 baths \| 1,558 sq.ft.	$520,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 2.31% Airbnb Rental Income: $2620 Traditional Rental Income: $2480 Airbnb ROI: 1.31% Traditional ROI: 2.31%
2155 FENNELL STREET Maitland, FL Welcome to 2155 Fennell Street, a beautifully renovated pool home nestled in the desirable...	3 beds \| 2 baths \| 1,822 sq.ft.	$489,900	Airbnb cash on cash: 2.62% Traditional cash on cash: 3.92% Airbnb Rental Income: $2620 Traditional Rental Income: $2589 Airbnb ROI: 2.62% Traditional ROI: 3.92%
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: 4.99% Traditional cash on cash: 5.91% Airbnb Rental Income: $2620 Traditional Rental Income: $2262 Airbnb ROI: 4.99% Traditional ROI: 5.91%
67 CYPRESS LANE Maitland, FL Under contract-accepting backup offers. Welcome to 67 Cypress Lane, a stunning single-owne...	4 beds \| 3 baths \| 2,292 sq.ft.	$999,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 2.11% Airbnb Rental Income: $4486 Traditional Rental Income: $3379 Airbnb ROI: 2.3% Traditional ROI: 2.11%
1130 Mechanic St Maitland, FL Pre-Construction. To be built. Come build your dream home on this exceptional homesite in ...	4 beds \| 4 baths \| 3,567 sq.ft.	$1,800,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 3.51% Airbnb Rental Income: $4486 Traditional Rental Income: $7698 Airbnb ROI: 1.03% Traditional ROI: 3.51%
51 Oakleigh Ln Maitland, FL Come see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comf...	4 beds \| 4 baths \| 4,149 sq.ft.	$1,075,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 3.35% Airbnb Rental Income: $4486 Traditional Rental Income: $5195 Airbnb ROI: 1.79% Traditional ROI: 3.35%
1111 Audubon Way Maitland, FL Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitlandâs most desi...	4 beds \| 3 baths \| 3,754 sq.ft.	$1,825,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 1.74% Airbnb Rental Income: $4486 Traditional Rental Income: $6014 Airbnb ROI: 0.29% Traditional ROI: 1.74%
570 DOMMERICH DRIVE Maitland, FL Under contract-accepting backup offers. Virtually Staged. ONE OF A KIND for Dommerich Esta...	4 beds \| 3 baths \| 2,956 sq.ft.	$795,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 4.49% Airbnb Rental Income: $4486 Traditional Rental Income: $4675 Airbnb ROI: 2.97% Traditional ROI: 4.49%
220 Alpine Dr 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.	$427,400	Airbnb cash on cash: 0.57% Traditional cash on cash: 2.89% Airbnb Rental Income: $1709 Traditional Rental Income: $2166 Airbnb ROI: 0.57% Traditional ROI: 2.89%
535 PAWNEE TRAIL Maitland, FL Under contract-accepting backup offers. Welcome to your dream home! This beautifully updat...	4 beds \| 3 baths \| 2,500 sq.ft.	$918,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 2.94% Airbnb Rental Income: $4486 Traditional Rental Income: $4422 Airbnb ROI: 1.92% Traditional ROI: 2.94%
623 GREEN MEADOW AVENUE Maitland, FL Welcome to this beautifully maintained two-owner concrete block home offering the perfect ...	4 beds \| 2 baths \| 1,909 sq.ft.	$450,000	Airbnb cash on cash: 6.74% Traditional cash on cash: 6.09% Airbnb Rental Income: $4486 Traditional Rental Income: $3272 Airbnb ROI: 6.74% Traditional ROI: 6.09%
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.	$599,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.13% Airbnb Rental Income: $2620 Traditional Rental Income: $2871 Airbnb ROI: 1.61% Traditional ROI: 3.13%
551 Ruffel St Maitland, FL Situated at the end of a cul-de-sac in the Eatonville/Maitland area, this home offers a gr...	3 beds \| 1 baths \| 1,162 sq.ft.	$258,500	Airbnb cash on cash: 5.6% Traditional cash on cash: 6.92% Airbnb Rental Income: $2620 Traditional Rental Income: $2369 Airbnb ROI: 5.6% Traditional ROI: 6.92%
1776 Bobtail Dr Maitland, FL Welcome to 1776 Bobtail Drive â the kind of home that doesnât just check boxesâ¦ it c...	4 beds \| 3 baths \| 2,344 sq.ft.	$519,999	Airbnb cash on cash: 5.58% Traditional cash on cash: 4.61% Airbnb Rental Income: $4486 Traditional Rental Income: $3079 Airbnb ROI: 5.58% Traditional ROI: 4.61%
2130 Deloraine Trl Maitland, FL Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neigh...	3 beds \| 2 baths \| 2,175 sq.ft.	$779,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 1.5% Airbnb Rental Income: $2620 Traditional Rental Income: $2919 Airbnb ROI: 0.26% Traditional ROI: 1.5%
987 Brightwater Cir Maitland, FL Your dream home awaits. Welcome to this exquisitely Renovated 4/4 PLUS OFFICE PLUS BONUS ...	5 beds \| 4 baths \| 3,270 sq.ft.	$1,100,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.45% Airbnb Rental Income: $4897 Traditional Rental Income: $5215 Airbnb ROI: 1.16% Traditional ROI: 2.45%
1244 E Lake Colony Dr Maitland, FL Modern, mediterranean lakefront residence in one of Maitlandâs most desirable GATED comm...	4 beds \| 5 baths \| 4,478 sq.ft.	$1,695,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.62% Airbnb Rental Income: $4486 Traditional Rental Income: $9761 Airbnb ROI: -0.12% Traditional ROI: 3.62%
1511 Glastonberry Rd Maitland, FL This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neigh...	5 beds \| 3 baths \| 2,376 sq.ft.	$549,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 5.59% Airbnb Rental Income: $4897 Traditional Rental Income: $3653 Airbnb ROI: 6.05% Traditional ROI: 5.59%
873 Cranes Ct Maitland, FL Beautifully Maintained Original-Owner Pool Home in Gated Lake Sybelia Cove. Pride of ow...	4 beds \| 4 baths \| 3,902 sq.ft.	$1,199,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 2.47% Airbnb Rental Income: $4486 Traditional Rental Income: $5106 Airbnb ROI: 1.1% Traditional ROI: 2.47%
9001 Lake Charity Dr Maitland, FL Welcome to a rare opportunity in the beautiful neighborhood of Druid Hills in Maitlandât...	3 beds \| 2 baths \| 1,623 sq.ft.	$550,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 2.88% Airbnb Rental Income: $2620 Traditional Rental Income: $2355 Airbnb ROI: 2.21% Traditional ROI: 2.88%
910 GAMEWELL AVENUE Maitland, FL Tucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath re...	3 beds \| 2 baths \| 2,214 sq.ft.	$645,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 2.93% Airbnb Rental Income: $2620 Traditional Rental Income: $2948 Airbnb ROI: 1.34% Traditional ROI: 2.93%
2154 FENNELL STREET Maitland, FL Under contract-accepting backup offers. Welcome to this meticulously maintained, one-owner...	3 beds \| 2 baths \| 1,642 sq.ft.	$420,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.89% Airbnb Rental Income: $2620 Traditional Rental Income: $2205 Airbnb ROI: 3.35% Traditional ROI: 3.89%
614 BROOKWOOD LANE Maitland, FL JUST REDUCED - Welcome to this meticulously updated, one-story masterpiece situated on a ...	5 beds \| 4 baths \| 3,485 sq.ft.	$899,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 4.41% Airbnb Rental Income: $4897 Traditional Rental Income: $4884 Airbnb ROI: 3.23% Traditional ROI: 4.41%
499 JULIAN LANE Maitland, FL Location, Location, Location. Welcome to your new home in Maitland! This conviently loca...	3 beds \| 3 baths \| 1,596 sq.ft.	$455,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 3.23% Airbnb Rental Income: $2620 Traditional Rental Income: $2216 Airbnb ROI: 2.71% Traditional ROI: 3.23%
541 MANOR ROAD Maitland, FL Tucked between the shores of Lake Nina and Lake Maitland, this beautifully reimagined Cali...	5 beds \| 3 baths \| 3,400 sq.ft.	$1,499,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 1.37% Airbnb Rental Income: $4897 Traditional Rental Income: $4358 Airbnb ROI: 1.04% Traditional ROI: 1.37%
457 FORESTWOOD LANE Maitland, FL Under contract-accepting backup offers. From the moment you step inside, youâre welcomed...	4 beds \| 3 baths \| 2,610 sq.ft.	$849,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 2.32% Airbnb Rental Income: $4486 Traditional Rental Income: $3516 Airbnb ROI: 2.36% Traditional ROI: 2.32%
1191 WILLOWBROOK TRAIL Maitland, FL Under contract-accepting backup offers. Don't miss this rare opportunity to purchase your ...	4 beds \| 2 baths \| 2,287 sq.ft.	$765,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.17% Airbnb Rental Income: $4486 Traditional Rental Income: $2785 Airbnb ROI: 3.25% Traditional ROI: 2.17%
119 Hollie Ct Maitland, FL Located in a premier Maitland neighborhood, 119 Hollie Ct presents a rare opportunity to o...	3 beds \| 3 baths \| 2,192 sq.ft.	$975,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 1.42% Airbnb Rental Income: $2620 Traditional Rental Income: $3402 Airbnb ROI: -0.13% Traditional ROI: 1.42%
1781 TONTO TRAIL Maitland, FL Under contract-accepting backup offers. Welcome to 1781 Tonto Trail, a 4-bedroom home in o...	4 beds \| 2 baths \| 1,880 sq.ft.	$600,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 3.05% Airbnb Rental Income: $4486 Traditional Rental Income: $2584 Airbnb ROI: 4.77% Traditional ROI: 3.05%

Your search for investment property begins and ends here

Single Family Homes for Sale in Maitland, FL

140 Wigwam Pl

Maitland, FL

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

$599,900

Airbnb cash on cash: 1.65%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $2620

Traditional Rental Income: $3387

Airbnb ROI: 1.65%

Traditional ROI: 4.05%

766 TERRA PLACE

Maitland, FL

4 beds | 5 baths | 3,040 sq.ft.

$1,149,900

Airbnb cash on cash: 1.49%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $4486

Traditional Rental Income: $6658

Airbnb ROI: 1.49%

Traditional ROI: 4.39%

448 Stonewood Ln

Maitland, FL

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

$599,900

Airbnb cash on cash: 3.08%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $4486

Traditional Rental Income: $3970

Airbnb ROI: 3.08%

Traditional ROI: 3.8%

755 WOODSIDE ROAD

Maitland, FL

3 beds | 3 baths | 3,049 sq.ft.

$975,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $2620

Traditional Rental Income: $3532

Airbnb ROI: 0.42%

Traditional ROI: 2.12%

220 Adams Dr

Maitland, FL

4 beds | 3 baths | 3,005 sq.ft.

$1,995,000

Airbnb cash on cash: 0.09%

Traditional cash on cash: 0.75%

Airbnb Rental Income: $4486

Traditional Rental Income: $4773

Airbnb ROI: 0.09%

Traditional ROI: 0.75%

631 Lake Catherine Dr

Maitland, FL

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

$1,795,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $2620

Traditional Rental Income: $3869

Airbnb ROI: -0.52%

Traditional ROI: 0.61%

2642 BROOKSIDE COURT

Maitland, FL

5 beds | 2 baths | 2,360 sq.ft.

$629,000

Airbnb cash on cash: 4.53%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $4897

Traditional Rental Income: $2974

Airbnb ROI: 4.53%

Traditional ROI: 2.96%

612 GREEN MEADOW AVENUE

Maitland, FL

3 beds | 2 baths | 1,707 sq.ft.

$490,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $2620

Traditional Rental Income: $2396

Airbnb ROI: 2.02%