Maitland, FL Investment Property for Sale

Real Estate Investments for Sale in Maitland, FL With High ROI

Are you looking for a vacation rental in Maitland, FL? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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
1515 OXFORD ROAD Maitland, FL Welcome Home! This 4 bedroom 2 Bath home nestled in English Woods Community with NO HOA!!...	4 beds \| 2 baths \| 2,105 sq.ft.	$450,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 4.51% Airbnb Rental Income: $4575 Traditional Rental Income: $2863 Airbnb ROI: 6.32% Traditional ROI: 4.51%
1800 King Arthur Circle Maitland, FL Visit this listing at Homepie com to schedule a showing, ask questions, inquire about work...	4 beds \| 3 baths \| 3,052 sq.ft.	$1,050,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 1.54% Airbnb Rental Income: $4575 Traditional Rental Income: $3442 Airbnb ROI: 1.73% Traditional ROI: 1.54%
1408 Lake Shadow Circle #1303 Maitland, FL Lovely 2/2 condo in the desired community of Visconti West. Vinyl plank flooring throughou...	2 beds \| 2 baths \| 1,048 sq.ft.	$235,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 3.69% Airbnb Rental Income: $2379 Traditional Rental Income: $1779 Airbnb ROI: 3.75% Traditional ROI: 3.69%
641 LAKE CATHERINE DRIVE Maitland, FL This light-infused modern pool home was essentially rebuilt in 2019 and sits on an elevate...	5 beds \| 6 baths \| 5,810 sq.ft.	$2,580,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.3% Airbnb Rental Income: $5153 Traditional Rental Income: $6070 Airbnb ROI: -0.52% Traditional ROI: 0.3%
1347 BENEVOLENT STREET Maitland, FL One or more photo(s) has been virtually staged. PRICE REDUCTION! AND $2000 in Closing Cost...	3 beds \| 3 baths \| 1,674 sq.ft.	$395,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 1.71% Airbnb Rental Income: $3420 Traditional Rental Income: $2367 Airbnb ROI: 2.5% Traditional ROI: 1.71%
1346 BENEVOLENT STREET Maitland, FL One or more photo(s) has been virtually staged. Welcome to this meticulously maintained to...	3 beds \| 3 baths \| 1,674 sq.ft.	$399,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 1.18% Airbnb Rental Income: $3420 Traditional Rental Income: $2294 Airbnb ROI: 2.16% Traditional ROI: 1.18%
1501 GROVE STREET #560 Maitland, FL Great opportunity to own a ONE FLOOR, END UNIT condo conveniently located in well-establis...	2 beds \| 2 baths \| 1,087 sq.ft.	$275,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 5.02% Airbnb Rental Income: $2379 Traditional Rental Income: $1775 Airbnb ROI: 5.1% Traditional ROI: 5.02%
818 PARK LAKE CIRCLE #10 Maitland, FL Welcome to this charming two-story Maitland condo featuring a spacious living room/dining ...	3 beds \| 3 baths \| 1,575 sq.ft.	$274,900	Airbnb cash on cash: 8.74% Traditional cash on cash: 7.36% Airbnb Rental Income: $3420 Traditional Rental Income: $2304 Airbnb ROI: 8.74% Traditional ROI: 7.36%
551 FINCHLEY ROAD Maitland, FL IF YOU ARE LOOKING FOR THE BEST DEAL IN MAITLAND FOR A 2/2 CONDO...THIS IS IT! This Wonder...	2 beds \| 2 baths \| 1,293 sq.ft.	$274,900	Airbnb cash on cash: 4.96% Traditional cash on cash: 5.25% Airbnb Rental Income: $2379 Traditional Rental Income: $1867 Airbnb ROI: 4.96% Traditional ROI: 5.25%
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.	$643,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 2.99% Airbnb Rental Income: $4575 Traditional Rental Income: $2938 Airbnb ROI: 4.13% Traditional ROI: 2.99%
326 BANYAN DRIVE Maitland, FL One or more photo(s) has been virtually staged. Welcome to this stunning property! This ch...	4 beds \| 3 baths \| 2,538 sq.ft.	$485,000	Airbnb cash on cash: 6.22% Traditional cash on cash: 5.58% Airbnb Rental Income: $4575 Traditional Rental Income: $3333 Airbnb ROI: 6.22% Traditional ROI: 5.58%
1888 DERBYSHIRE ROAD Maitland, FL Welcome to a captivating blend of comfort and style at 1888 Derbyshire Road. This charming...	4 beds \| 3 baths \| 3,853 sq.ft.	$998,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 1.33% Airbnb Rental Income: $4575 Traditional Rental Income: $3233 Airbnb ROI: 1.75% Traditional ROI: 1.33%
2251 HUNTERFIELD ROAD Maitland, FL One or more photo(s) has been virtually staged. Welcome to your dream home, where timeless...	4 beds \| 2 baths \| 2,124 sq.ft.	$625,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 2.86% Airbnb Rental Income: $4575 Traditional Rental Income: $2852 Airbnb ROI: 4.18% Traditional ROI: 2.86%
180 BIRCHWOOD DRIVE Maitland, FL One or more photo(s) has been virtually staged. Welcome home to this charming property tha...	3 beds \| 2 baths \| 1,513 sq.ft.	$452,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 2.93% Airbnb Rental Income: $3420 Traditional Rental Income: $2242 Airbnb ROI: 3.92% Traditional ROI: 2.93%
335 LIME STREET Maitland, FL Feast your eyes on this rare opportunity to own two sets of duplexes fully rented out in t...	N/A beds \| N/A baths \| 1,479 sq.ft.	$740,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.83% Airbnb Rental Income: $null Traditional Rental Income: $1591 Airbnb ROI: N/A Traditional ROI: 0.83%
1345 BENEVOLENT STREET #1345 Maitland, FL Nestled within the gated community of Montacino, this charming Mediterranean style 3-bedro...	3 beds \| 3 baths \| 1,752 sq.ft.	$390,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 1.35% Airbnb Rental Income: $3420 Traditional Rental Income: $2367 Airbnb ROI: 2.16% Traditional ROI: 1.35%
876 TOWN CIRCLE #127 Maitland, FL Donât miss this fabulous three bedroom, 3 bathroom condo minutes from Park Avenue in the...	3 beds \| 3 baths \| 1,432 sq.ft.	$299,900	Airbnb cash on cash: 7.49% Traditional cash on cash: 5.72% Airbnb Rental Income: $3420 Traditional Rental Income: $2161 Airbnb ROI: 7.49% Traditional ROI: 5.72%
1016 HAMLET DR Maitland, FL Nestled in the heart of Maitland, Florida, 1016 Hamlet Drive beckons with its charming ext...	3 beds \| 2 baths \| 1,146 sq.ft.	$325,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 4.36% Airbnb Rental Income: $3420 Traditional Rental Income: $2127 Airbnb ROI: 6.11% Traditional ROI: 4.36%
1627 GULFVIEW DRIVE #441-B Maitland, FL Experience the epitome of lakeside living in beautiful Park Lake Grove with this remarkabl...	3 beds \| 3 baths \| 1,328 sq.ft.	$288,990	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.57% Airbnb Rental Income: $3420 Traditional Rental Income: $2113 Airbnb ROI: 4.59% Traditional ROI: 2.57%
924 & 922 ROBINHOOD COURT Maitland, FL Great investment opportunity to add this duplex in the heart of Maitland to your rental po...	N/A beds \| N/A baths \| 2,538 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.86% Airbnb Rental Income: $null Traditional Rental Income: $1571 Airbnb ROI: N/A Traditional ROI: 0.86%
824 PARK LAKE PLACE #824 Maitland, FL Appraised to sell! Welcome to your new home in the heart of the serene Park Lake Woods com...	2 beds \| 3 baths \| 1,768 sq.ft.	$275,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 3.07% Airbnb Rental Income: $2379 Traditional Rental Income: $2199 Airbnb ROI: 1.51% Traditional ROI: 3.07%
103 OAKWOOD DRIVE Maitland, FL This home is on a quiet street that dead ends into Lake Seminary. It is a three-bedroom, t...	3 beds \| 2 baths \| 1,500 sq.ft.	$425,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 3.52% Airbnb Rental Income: $3420 Traditional Rental Income: $2234 Airbnb ROI: 4.6% Traditional ROI: 3.52%
251 W HORATIO AVENUE Maitland, FL Incredible opportunity to own one of the oldest homes in Maitland. ThisÂ charming 2-bedroo...	4 beds \| 2 baths \| 1,648 sq.ft.	$650,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 2.86% Airbnb Rental Income: $4575 Traditional Rental Income: $2752 Airbnb ROI: 4.3% Traditional ROI: 2.86%
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: 3.67% Traditional cash on cash: 2.91% Airbnb Rental Income: $3420 Traditional Rental Income: $2254 Airbnb ROI: 3.67% Traditional ROI: 2.91%
2166 LAKE HOWELL PRESERVE COURT Maitland, FL Priced Under Value Come see this 3 bedroom, 3 1/2 bathroom, 2,136 square foot luxury tow...	3 beds \| 4 baths \| 2,136 sq.ft.	$549,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 1.51% Airbnb Rental Income: $3420 Traditional Rental Income: $2936 Airbnb ROI: 0.97% Traditional ROI: 1.51%
234 FLAME AVENUE Maitland, FL This Maitland POOL home has been uniquely redesigned to an open floor plan and features 5 ...	5 beds \| 3 baths \| 3,854 sq.ft.	$1,075,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 1.71% Airbnb Rental Income: $5153 Traditional Rental Income: $3389 Airbnb ROI: 2.42% Traditional ROI: 1.71%
2462 MARKINGHAM ROAD Maitland, FL Welcome to this lovely oak-shaded home and street in family-friendly English Estates, Sout...	4 beds \| 2 baths \| 2,400 sq.ft.	$629,950	Airbnb cash on cash: 4.5% Traditional cash on cash: 3.61% Airbnb Rental Income: $4575 Traditional Rental Income: $3099 Airbnb ROI: 4.5% Traditional ROI: 3.61%
2555 SWEETWATER TRAIL Maitland, FL Here is your chance to put your stamp on this original "Clayton" pool home in desired area...	4 beds \| 3 baths \| 2,110 sq.ft.	$550,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 3.67% Airbnb Rental Income: $4575 Traditional Rental Income: $3038 Airbnb ROI: 4.81% Traditional ROI: 3.67%
731 SEQUOIA TRAIL Maitland, FL Welcome home to your 4 bed, 2 bath updated home with a pool, spa and creek flowing through...	4 beds \| 2 baths \| 1,797 sq.ft.	$825,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 1.77% Airbnb Rental Income: $4575 Traditional Rental Income: $2686 Airbnb ROI: 2.99% Traditional ROI: 1.77%
553 FINCHLEY ROAD #553 Maitland, FL Outstanding condo in Maitland, this HUGE 3-bedroom, 2-bathroom condo offers an inviting op...	3 beds \| 2 baths \| 1,664 sq.ft.	$299,000	Airbnb cash on cash: 7.23% Traditional cash on cash: 5.34% Airbnb Rental Income: $3420 Traditional Rental Income: $2129 Airbnb ROI: 7.23% Traditional ROI: 5.34%
514 WIGMAN DRIVE Maitland, FL Lovely Gem tat has been fully remodeled and fully furnished as a 3 bedroom and 2 bathroom ...	3 beds \| 2 baths \| 1,148 sq.ft.	$349,999	Airbnb cash on cash: 5.65% Traditional cash on cash: 3.65% Airbnb Rental Income: $3420 Traditional Rental Income: $2003 Airbnb ROI: 5.65% Traditional ROI: 3.65%
502 LISA LANE Maitland, FL One or more photo(s) has been virtually staged. PHENONINAL PRICE REDUCTION. This beautif...	4 beds \| 3 baths \| 2,552 sq.ft.	$769,900	Airbnb cash on cash: 3.47% Traditional cash on cash: 3.1% Airbnb Rental Income: $4575 Traditional Rental Income: $3356 Airbnb ROI: 3.47% Traditional ROI: 3.1%
912 PARK LAKE CIRCLE #4 Maitland, FL New Paint, New Carpet, MOVE IN READY! Great townhome in prime neighborhood just minutes fr...	2 beds \| 2 baths \| 1,353 sq.ft.	$289,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.92% Airbnb Rental Income: $2379 Traditional Rental Income: $1828 Airbnb ROI: 0.79% Traditional ROI: 0.92%
1006 KEWANNEE TRAIL Maitland, FL Under contract-accepting backup offers. Welcome to Dommerich Hills and 1006 Kewannee Trail...	4 beds \| 3 baths \| 1,896 sq.ft.	$659,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 1.94% Airbnb Rental Income: $4575 Traditional Rental Income: $2570 Airbnb ROI: 3.66% Traditional ROI: 1.94%
1765 LYNDALE BOULEVARD Maitland, FL MULTIPLE OFFERS HAVE BEEN RECEIVED. SELLER IS REQUESTING ANY OFFERS BE SUBMITTED BY 5:00 P...	3 beds \| 2 baths \| 1,310 sq.ft.	$469,500	Airbnb cash on cash: 2.97% Traditional cash on cash: 1.67% Airbnb Rental Income: $3420 Traditional Rental Income: $2094 Airbnb ROI: 2.97% Traditional ROI: 1.67%
180 SHELL POINT W Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ne...	5 beds \| 4 baths \| 4,017 sq.ft.	$2,250,000	Airbnb cash on cash: -0.24% Traditional cash on cash: -0.07% Airbnb Rental Income: $5153 Traditional Rental Income: $4452 Airbnb ROI: -0.24% Traditional ROI: -0.07%
580 MANOR ROAD Maitland, FL Under contract-accepting backup offers. Embrace the epitome of luxury living with this ext...	4 beds \| 7 baths \| 5,957 sq.ft.	$4,399,000	Airbnb cash on cash: -0.69% Traditional cash on cash: -0.3% Airbnb Rental Income: $4575 Traditional Rental Income: $5246 Airbnb ROI: -0.69% Traditional ROI: -0.3%
1400 LAKE SHADOW CIRCLE #10304 Maitland, FL Beautiful one bedroom located in a beautiful gate community, washer and dryer in unit. Vis...	1 beds \| 1 baths \| 672 sq.ft.	$165,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 2.29% Airbnb Rental Income: $1859 Traditional Rental Income: $1385 Airbnb ROI: 2.13% Traditional ROI: 2.29%
329 CHERRYWOOD GARDENS DRIVE #329 Maitland, FL Under contract-accepting backup offers. This beautiful condo was remodeled in 2016. It is ...	2 beds \| 2 baths \| 905 sq.ft.	$210,000	Airbnb cash on cash: 3% Traditional cash on cash: 2.41% Airbnb Rental Income: $2379 Traditional Rental Income: $1676 Airbnb ROI: 3% Traditional ROI: 2.41%
208 FLAME AVENUE Maitland, FL Welcome to this beautiful custom-built Maitland home in a park like setting. Gorgeous, ele...	5 beds \| 3 baths \| 3,488 sq.ft.	$899,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 1.87% Airbnb Rental Income: $5153 Traditional Rental Income: $3374 Airbnb ROI: 2.74% Traditional ROI: 1.87%

Real Estate investment in Maitland, FL

There are 52 properties for sale in the city of Maitland . The median list price in Maitland is $469,500 and the average price per square foot is $216. In May 2024, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,254.

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

There are 52 investment properties available for sale in Maitland.

In 2024, 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 $3,420.

Your search for investment property begins and ends here

Investment Property for Sale in Maitland, FL

1515 OXFORD ROAD

Maitland, FL

4 beds | 2 baths | 2,105 sq.ft.

$450,000

Airbnb cash on cash: 6.32%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $4575

Traditional Rental Income: $2863

Airbnb ROI: 6.32%

Traditional ROI: 4.51%

1800 King Arthur Circle

Maitland, FL

4 beds | 3 baths | 3,052 sq.ft.

$1,050,000

Airbnb cash on cash: 1.73%

Traditional cash on cash: 1.54%

Airbnb Rental Income: $4575

Traditional Rental Income: $3442

Airbnb ROI: 1.73%

Traditional ROI: 1.54%

1408 Lake Shadow Circle #1303

Maitland, FL

2 beds | 2 baths | 1,048 sq.ft.

$235,000

Airbnb cash on cash: 3.75%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $2379

Traditional Rental Income: $1779

Airbnb ROI: 3.75%

Traditional ROI: 3.69%

641 LAKE CATHERINE DRIVE

Maitland, FL

5 beds | 6 baths | 5,810 sq.ft.

$2,580,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $5153

Traditional Rental Income: $6070

Airbnb ROI: -0.52%

Traditional ROI: 0.3%

1347 BENEVOLENT STREET

Maitland, FL

3 beds | 3 baths | 1,674 sq.ft.

$395,000

Airbnb cash on cash: 2.5%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $3420

Traditional Rental Income: $2367

Airbnb ROI: 2.5%

Traditional ROI: 1.71%

1346 BENEVOLENT STREET

Maitland, FL

3 beds | 3 baths | 1,674 sq.ft.

$399,900

Airbnb cash on cash: 2.16%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $3420

Traditional Rental Income: $2294

Airbnb ROI: 2.16%

Traditional ROI: 1.18%

1501 GROVE STREET #560

Maitland, FL

2 beds | 2 baths | 1,087 sq.ft.

$275,000

Airbnb cash on cash: 5.1%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $2379

Traditional Rental Income: $1775

Airbnb ROI: 5.1%

Traditional ROI: 5.02%

818 PARK LAKE CIRCLE #10

Maitland, FL

3 beds | 3 baths | 1,575 sq.ft.

$274,900

Airbnb cash on cash: 8.74%

Traditional cash on cash: 7.36%

Airbnb Rental Income: $3420

Traditional Rental Income: $2304

Airbnb ROI: 8.74%