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
195 E FAITH TERRACE Maitland, FL Perfectly positioned on the tranquil shores of Lake Seminary, this beautiful home offers t...	3 beds \| 2 baths \| 2,502 sq.ft.	$849,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 1.58% Airbnb Rental Income: $3440 Traditional Rental Income: $2737 Airbnb ROI: 1.5% Traditional ROI: 1.58%
2517 CAPER LANE #207 Maitland, FL One or more photo(s) has been virtually staged. Charming 1 Bedroom, 1 Bathroom condo in be...	1 beds \| 1 baths \| 550 sq.ft.	$115,000	Airbnb cash on cash: 9.04% Traditional cash on cash: 8.52% Airbnb Rental Income: $1832 Traditional Rental Income: $1280 Airbnb ROI: 9.04% Traditional ROI: 8.52%
201 CEDARWOOD DRIVE Maitland, FL Under contract-accepting backup offers. Welcome to this beautifully reimagined 3-bedroom, ...	3 beds \| 2 baths \| 2,200 sq.ft.	$839,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 1.89% Airbnb Rental Income: $3440 Traditional Rental Income: $2949 Airbnb ROI: 1.54% Traditional ROI: 1.89%
824 TOWN CIRCLE #101 Maitland, FL One or more photo(s) has been virtually staged. Move-in ready two story townhome. This bea...	3 beds \| 3 baths \| 1,565 sq.ft.	$289,990	Airbnb cash on cash: 5.65% Traditional cash on cash: 3.9% Airbnb Rental Income: $3440 Traditional Rental Income: $2200 Airbnb ROI: 5.65% Traditional ROI: 3.9%
1375 LAKE SHADOW CIRCLE #11208 Maitland, FL Step into comfort and ease with this charming 2-bedroom, 1-bath condo at 1375 Lake Shadow ...	2 beds \| 1 baths \| 898 sq.ft.	$195,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 2.79% Airbnb Rental Income: $2379 Traditional Rental Income: $1449 Airbnb ROI: 4.65% Traditional ROI: 2.79%
500 BANYON TREE CIRCLE #104 Maitland, FL Welcome to this beautifully renovated 3-bedroom, 2-bathroom first-floor condominium locate...	3 beds \| 2 baths \| 1,428 sq.ft.	$209,900	Airbnb cash on cash: 7.62% Traditional cash on cash: 5.62% Airbnb Rental Income: $3440 Traditional Rental Income: $2280 Airbnb ROI: 7.62% Traditional ROI: 5.62%
1888 DERBYSHIRE ROAD Maitland, FL Under contract-accepting backup offers. Welcome to your dream home in the friendly communi...	4 beds \| 3 baths \| 3,853 sq.ft.	$825,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.23% Airbnb Rental Income: $5007 Traditional Rental Income: $3491 Airbnb ROI: 2.87% Traditional ROI: 2.23%
2133 KORAT LANE Maitland, FL Under contract-accepting backup offers. Exceptional Value ** New Reduced price $514,900...	4 beds \| 3 baths \| 2,359 sq.ft.	$514,900	Airbnb cash on cash: 5.81% Traditional cash on cash: 4.28% Airbnb Rental Income: $5007 Traditional Rental Income: $3249 Airbnb ROI: 5.81% Traditional ROI: 4.28%
515 W FAITH TERRACE Maitland, FL Beautiful mid-century modern 3 bed, 2 bath, 2 car garage + OFFICE, one-story home on the t...	3 beds \| 2 baths \| 2,205 sq.ft.	$539,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 3.91% Airbnb Rental Income: $3440 Traditional Rental Income: $3030 Airbnb ROI: 3.21% Traditional ROI: 3.91%
2525 CAPER LANE #205 Maitland, FL Condo features plenty of natural light, full side kitchen, bathroom with bathtub shower co...	1 beds \| 1 baths \| 550 sq.ft.	$119,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 5.6% Airbnb Rental Income: $1832 Traditional Rental Income: $1232 Airbnb ROI: 6.52% Traditional ROI: 5.6%
708 THUNDER TRAIL Maitland, FL Welcome to 708 Thunder Trail in beautiful Maitland, Florida â a stunning 4-bedroom, 2-ba...	4 beds \| 2 baths \| 1,907 sq.ft.	$650,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 2.68% Airbnb Rental Income: $5007 Traditional Rental Income: $3074 Airbnb ROI: 4.18% Traditional ROI: 2.68%
505 LAKE SHORE DRIVE Maitland, FL Imagine mornings with the sunrise shimmering across Lake Faith, directly across the street...	4 beds \| 2 baths \| 2,317 sq.ft.	$589,990	Airbnb cash on cash: 5.69% Traditional cash on cash: 3.58% Airbnb Rental Income: $5007 Traditional Rental Income: $2823 Airbnb ROI: 5.69% Traditional ROI: 3.58%
249 SPARTAN DRIVE Maitland, FL Discover Your Perfect Maitland Retreat! Tucked away on a quiet dead-end street, this deli...	4 beds \| 2 baths \| 1,579 sq.ft.	$349,900	Airbnb cash on cash: 9.6% Traditional cash on cash: 4.44% Airbnb Rental Income: $5007 Traditional Rental Income: $2287 Airbnb ROI: 9.6% Traditional ROI: 4.44%
1150 LAKE SHADOW CIRCLE #3104 Maitland, FL One or more photo(s) has been virtually staged. SELLER'S PREFERRED LENDER IS OFFERING UP T...	2 beds \| 2 baths \| 1,048 sq.ft.	$224,900	Airbnb cash on cash: 3.93% Traditional cash on cash: 3.03% Airbnb Rental Income: $2379 Traditional Rental Income: $1602 Airbnb ROI: 3.93% Traditional ROI: 3.03%
2031 EATON STREET Maitland, FL Under contract-accepting backup offers. 2.99% Assumable Mortgage Rate Available Welcome ...	4 beds \| 3 baths \| 2,518 sq.ft.	$399,000	Airbnb cash on cash: 8.64% Traditional cash on cash: 5.57% Airbnb Rental Income: $5007 Traditional Rental Income: $2838 Airbnb ROI: 8.64% Traditional ROI: 5.57%
1460 LAKE SHADOW CIRCLE #7204 Maitland, FL Under contract-accepting backup offers. Resort style living in this sought after gated com...	3 beds \| 2 baths \| 1,243 sq.ft.	$239,900	Airbnb cash on cash: 6.93% Traditional cash on cash: 3.55% Airbnb Rental Income: $3440 Traditional Rental Income: $1911 Airbnb ROI: 6.93% Traditional ROI: 3.55%
214 CHERRYWOOD DRIVE Maitland, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	3 beds \| 2 baths \| 1,178 sq.ft.	$335,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 4.91% Airbnb Rental Income: $3440 Traditional Rental Income: $2281 Airbnb ROI: 6.17% Traditional ROI: 4.91%
135 ROOSEVELT PLACE Maitland, FL This charming home boasts a wealth of valuable upgrades and improvements, making it an ent...	4 beds \| 2 baths \| 2,426 sq.ft.	$579,900	Airbnb cash on cash: 5.21% Traditional cash on cash: 2.58% Airbnb Rental Income: $5007 Traditional Rental Income: $2560 Airbnb ROI: 5.21% Traditional ROI: 2.58%
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: 3.7% Traditional cash on cash: 3.05% Airbnb Rental Income: $3440 Traditional Rental Income: $2328 Airbnb ROI: 3.7% Traditional ROI: 3.05%
1140 S ORLANDO AVENUE #E-1 Maitland, FL One or more photo(s) has been virtually staged. RARE opportunity to live in the Premier La...	2 beds \| 1 baths \| 816 sq.ft.	$224,900	Airbnb cash on cash: 4.08% Traditional cash on cash: 4.27% Airbnb Rental Income: $2379 Traditional Rental Income: $1834 Airbnb ROI: 4.08% Traditional ROI: 4.27%
1231 SIDCUP ROAD Maitland, FL Prepare to be captivated by this fully renovated gem located in the highly sought after En...	3 beds \| 2 baths \| 1,798 sq.ft.	$550,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 3.91% Airbnb Rental Income: $3440 Traditional Rental Income: $2775 Airbnb ROI: 3.72% Traditional ROI: 3.91%
404 BANYON TREE CIRCLE #200 Maitland, FL Welcome to this spacious 1,612 sq. ft. condo, perfectly located for both convenience and l...	3 beds \| 2 baths \| 1,612 sq.ft.	$197,000	Airbnb cash on cash: 7.7% Traditional cash on cash: 5.19% Airbnb Rental Income: $3440 Traditional Rental Income: $2208 Airbnb ROI: 7.7% Traditional ROI: 5.19%
2201 SUNDERLAND ROAD Maitland, FL Welcome to your beautifully renovated corner-lot oasis in the desirable English Estates co...	3 beds \| 2 baths \| 1,798 sq.ft.	$564,000	Airbnb cash on cash: 3.59% Traditional cash on cash: 3.69% Airbnb Rental Income: $3440 Traditional Rental Income: $2729 Airbnb ROI: 3.59% Traditional ROI: 3.69%
1221 THUNDER TRAIL Maitland, FL Under contract-accepting backup offers. Don't miss out on this AMAZING Maitland home for u...	3 beds \| 2 baths \| 1,908 sq.ft.	$440,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 4.02% Airbnb Rental Income: $3440 Traditional Rental Income: $2377 Airbnb ROI: 4.75% Traditional ROI: 4.02%
380 BANYAN DRIVE Maitland, FL Charming 3BR/2BA Home with Updated Interior This move-in ready home features 3 bedrooms...	3 beds \| 2 baths \| 1,404 sq.ft.	$459,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 3.32% Airbnb Rental Income: $3440 Traditional Rental Income: $2055 Airbnb ROI: 4.76% Traditional ROI: 3.32%
135 JAMES PLACE Maitland, FL Under contract-accepting backup offers. ACTIVE on the Market â Enhanced and Priced to Se...	5 beds \| 5 baths \| 3,885 sq.ft.	$1,599,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 2.78% Airbnb Rental Income: $5533 Traditional Rental Income: $6946 Airbnb ROI: 1.08% Traditional ROI: 2.78%
255 W GEORGE AVENUE Maitland, FL Experience the blend of timeless elegance and modern luxury in this Maitland estate a bloc...	5 beds \| 4 baths \| 4,814 sq.ft.	$1,700,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 2.23% Airbnb Rental Income: $5533 Traditional Rental Income: $5853 Airbnb ROI: 1.33% Traditional ROI: 2.23%
711 THOMPSON AVENUE Maitland, FL Come see this beautifully remodeled 3-bedroom, 1-bath home near the heart of Maitland! Thi...	3 beds \| 1 baths \| 1,056 sq.ft.	$289,000	Airbnb cash on cash: 8.24% Traditional cash on cash: 4.6% Airbnb Rental Income: $3440 Traditional Rental Income: $1687 Airbnb ROI: 8.24% Traditional ROI: 4.6%
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.	$325,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 2.7% Airbnb Rental Income: $3440 Traditional Rental Income: $2169 Airbnb ROI: 4.37% Traditional ROI: 2.7%
530 RUFFEL STREET Maitland, FL Under contract-accepting backup offers. Great property to add to your investment portfolio...	3 beds \| 2 baths \| 1,449 sq.ft.	$249,900	Airbnb cash on cash: 9.1% Traditional cash on cash: 6.74% Airbnb Rental Income: $3440 Traditional Rental Income: $2122 Airbnb ROI: 9.1% Traditional ROI: 6.74%
1913 POINSETTA LANE Maitland, FL Motivated Seller â Stylishly Renovated 4-Bedroom Home in Prime Maitland Location! Donâ...	4 beds \| 2 baths \| 1,664 sq.ft.	$441,900	Airbnb cash on cash: 8.05% Traditional cash on cash: 4.21% Airbnb Rental Income: $5007 Traditional Rental Income: $2394 Airbnb ROI: 8.05% Traditional ROI: 4.21%
1325 LAKE SHADOW CIRCLE #12303 Maitland, FL Welcome to carefree living in the sought-after Visconti community of Maitland! This beauti...	2 beds \| 2 baths \| 1,048 sq.ft.	$215,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 3.48% Airbnb Rental Income: $2379 Traditional Rental Income: $1614 Airbnb ROI: 4.37% Traditional ROI: 3.48%
2632 DERBYSHIRE ROAD Maitland, FL 2025 ROOF \| POOL HOME Start your new life to one of Orlando's most prestigious sub...	4 beds \| 2 baths \| 1,770 sq.ft.	$565,000	Airbnb cash on cash: 5.58% Traditional cash on cash: 3.35% Airbnb Rental Income: $5007 Traditional Rental Income: $2807 Airbnb ROI: 5.58% Traditional ROI: 3.35%
1135 THUNDER TRAIL Maitland, FL Distinctive Dommerich Hills Home with Flexible Floor Plan and Modern Upgrades. Welcom...	4 beds \| 4 baths \| 2,651 sq.ft.	$669,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 6.06% Airbnb Rental Income: $5007 Traditional Rental Income: $5002 Airbnb ROI: 4.43% Traditional ROI: 6.06%
736 FOREST GLEN COURT Maitland, FL One or more photo(s) has been virtually staged. New Price - Motivated Seller!! Welcome to ...	4 beds \| 2 baths \| 1,647 sq.ft.	$479,900	Airbnb cash on cash: 6.62% Traditional cash on cash: 3.56% Airbnb Rental Income: $5007 Traditional Rental Income: $2614 Airbnb ROI: 6.62% Traditional ROI: 3.56%
1277 BLESSING STREET Maitland, FL This is a well-located townhome in the gated community of Montacino. The unit has been ref...	3 beds \| 3 baths \| 1,751 sq.ft.	$399,990	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.28% Airbnb Rental Income: $3440 Traditional Rental Income: $2314 Airbnb ROI: 3.25% Traditional ROI: 2.28%
1745 E ADAMS DRIVE Maitland, FL Classic Colonial Brick Home on highly desired E Adama Drive across from Lake Maitland! 4 ...	4 beds \| 4 baths \| 2,212 sq.ft.	$1,199,777	Airbnb cash on cash: 1.31% Traditional cash on cash: 0.99% Airbnb Rental Income: $5007 Traditional Rental Income: $3628 Airbnb ROI: 1.31% Traditional ROI: 0.99%
2155 FENNELL STREET Maitland, FL Back to Market -This is a three-bedroom two-bathroom pool house well located that needs so...	3 beds \| 2 baths \| 1,822 sq.ft.	$395,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 5.11% Airbnb Rental Income: $3440 Traditional Rental Income: $2589 Airbnb ROI: 5.35% Traditional ROI: 5.11%
305 WEST LAKE FAITH DRIVE #139 Maitland, FL Under contract-accepting backup offers. This impeccable first-floor corner unit features a...	3 beds \| 2 baths \| 1,739 sq.ft.	$305,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 3.7% Airbnb Rental Income: $3440 Traditional Rental Income: $2243 Airbnb ROI: 5.21% Traditional ROI: 3.7%
941 VERSAILLES CIRCLE Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Se...	4 beds \| 3 baths \| 2,717 sq.ft.	$1,150,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 1.25% Airbnb Rental Income: $5007 Traditional Rental Income: $3543 Airbnb ROI: 1.67% Traditional ROI: 1.25%

Real Estate investment in Maitland, FL

There are 71 properties for sale in the city of Maitland . The median list price in Maitland is $454,500 and the average price per square foot is $247. In October 2025, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,328.

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

There are 71 investment properties available for sale in Maitland.

In 2025, 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

195 E FAITH TERRACE

Maitland, FL

3 beds | 2 baths | 2,502 sq.ft.

$849,000

Airbnb cash on cash: 1.5%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $3440

Traditional Rental Income: $2737

Airbnb ROI: 1.5%

Traditional ROI: 1.58%

2517 CAPER LANE #207

Maitland, FL

1 beds | 1 baths | 550 sq.ft.

$115,000

Airbnb cash on cash: 9.04%

Traditional cash on cash: 8.52%

Airbnb Rental Income: $1832

Traditional Rental Income: $1280

Airbnb ROI: 9.04%

Traditional ROI: 8.52%

201 CEDARWOOD DRIVE

Maitland, FL

3 beds | 2 baths | 2,200 sq.ft.

$839,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $3440

Traditional Rental Income: $2949

Airbnb ROI: 1.54%

Traditional ROI: 1.89%

824 TOWN CIRCLE #101

Maitland, FL

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

$289,990

Airbnb cash on cash: 5.65%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $3440

Traditional Rental Income: $2200

Airbnb ROI: 5.65%

Traditional ROI: 3.9%

1375 LAKE SHADOW CIRCLE #11208

Maitland, FL

2 beds | 1 baths | 898 sq.ft.

$195,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $2379

Traditional Rental Income: $1449

Airbnb ROI: 4.65%

Traditional ROI: 2.79%

500 BANYON TREE CIRCLE #104

Maitland, FL

3 beds | 2 baths | 1,428 sq.ft.

$209,900

Airbnb cash on cash: 7.62%

Traditional cash on cash: 5.62%

Airbnb Rental Income: $3440

Traditional Rental Income: $2280

Airbnb ROI: 7.62%

Traditional ROI: 5.62%

1888 DERBYSHIRE ROAD

Maitland, FL

4 beds | 3 baths | 3,853 sq.ft.

$825,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $5007

Traditional Rental Income: $3491

Airbnb ROI: 2.87%

Traditional ROI: 2.23%

2133 KORAT LANE

Maitland, FL

4 beds | 3 baths | 2,359 sq.ft.

$514,900

Airbnb cash on cash: 5.81%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $5007

Traditional Rental Income: $3249

Airbnb ROI: 5.81%