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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1521 OXFORD ROAD Maitland, FL Welcome to 1521 Oxford Rd - here's your opportunity to own a move in ready corner lot prop...	4 beds \| 2 baths \| 1,925 sq.ft.	$489,900	Airbnb cash on cash: 6.56% Traditional cash on cash: 4.04% Airbnb Rental Income: $5007 Traditional Rental Income: $2826 Airbnb ROI: 6.56% Traditional ROI: 4.04%
1020 TUCKASEEGEE TRAIL Maitland, FL Under contract-accepting backup offers. Rare find in Dommerich Estates with your very own ...	5 beds \| 4 baths \| 2,603 sq.ft.	$1,034,999	Airbnb cash on cash: 2.85% Traditional cash on cash: 3.44% Airbnb Rental Income: $5533 Traditional Rental Income: $4986 Airbnb ROI: 2.85% Traditional ROI: 3.44%
1800 KING ARTHUR CIRCLE Maitland, FL MOTIVATED SELLER FINANCING TERMS AVAILABLE: 25% Down Payment with 5.99% Interest Rate....	4 beds \| 3 baths \| 3,052 sq.ft.	$1,040,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 1.55% Airbnb Rental Income: $5007 Traditional Rental Income: $3615 Airbnb ROI: 1.93% Traditional ROI: 1.55%
1501 Oranole Road Maitland, FL Elegant pool home in iconic & coveted Bretton Woods. Discover classic charm & modern comfo...	3 beds \| 3 baths \| 2,807 sq.ft.	$799,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 2.4% Airbnb Rental Income: $3440 Traditional Rental Income: $3117 Airbnb ROI: 1.81% Traditional ROI: 2.4%
2161 LAKE HOWELL PRESERVE COURT Maitland, FL Welcome to 2161 Lake Howell Preserve Court where luxury, elegance and comfort meet. The cr...	3 beds \| 4 baths \| 2,188 sq.ft.	$614,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 2.27% Airbnb Rental Income: $3440 Traditional Rental Income: $3133 Airbnb ROI: 1.48% Traditional ROI: 2.27%
320 EATON STREET Maitland, FL Welcome to this fantastic 2-bedroom, 1-bath home that has been thoughtfully upgraded throu...	2 beds \| 1 baths \| 846 sq.ft.	$249,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 4.99% Airbnb Rental Income: $2379 Traditional Rental Income: $1603 Airbnb ROI: 5.81% Traditional ROI: 4.99%
514 WIGMAN DRIVE Maitland, FL Fully upgraded home with all the bells and whistles. Lots of yard space. Can be sold furni...	3 beds \| 2 baths \| 1,148 sq.ft.	$359,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.26% Airbnb Rental Income: $3440 Traditional Rental Income: $1911 Airbnb ROI: 5.54% Traditional ROI: 3.26%
956 STONEWOOD LANE Maitland, FL STUNNING LAKEFRONT RETREAT IN MAITLAND! Discover your new beginning at this exquisite prop...	5 beds \| 3 baths \| 2,837 sq.ft.	$750,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 2.86% Airbnb Rental Income: $5533 Traditional Rental Income: $3436 Airbnb ROI: 4.27% Traditional ROI: 2.86%
251 W LAKE FAITH DRIVE #204 Maitland, FL PRICE IMPROVEMENT!! Welcome to your dream home at Lake Faith Villas gated community in th...	3 beds \| 2 baths \| 1,739 sq.ft.	$369,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.62% Airbnb Rental Income: $3440 Traditional Rental Income: $2396 Airbnb ROI: 5.44% Traditional ROI: 4.62%
631 LAKE CATHERINE DRIVE Maitland, FL Wonderful Lakefront Opportunity in Maitland. This charming two-bedroom, two bath home sits...	2 beds \| 2 baths \| 2,351 sq.ft.	$950,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 0.82% Airbnb Rental Income: $2379 Traditional Rental Income: $2779 Airbnb ROI: -0.3% Traditional ROI: 0.82%
920 PARK LAKE CIRCLE #36 Maitland, FL LOCATION! LOCATION! LOCATION! This Maitland townhome has it all. An end unit with 3 bedroo...	3 beds \| 3 baths \| 1,486 sq.ft.	$305,000	Airbnb cash on cash: 7.32% Traditional cash on cash: 5.96% Airbnb Rental Income: $3440 Traditional Rental Income: $2289 Airbnb ROI: 7.32% Traditional ROI: 5.96%
503 BROOKSIDE CIRCLE Maitland, FL Under contract-accepting backup offers. Welcome to your 3 bed / 3.5 bath totally remodeled...	3 beds \| 4 baths \| 2,265 sq.ft.	$749,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 2.17% Airbnb Rental Income: $3440 Traditional Rental Income: $2683 Airbnb ROI: 2.16% Traditional ROI: 2.17%
1231 STRATFORD ROAD Maitland, FL Under contract-accepting backup offers. MOVE IN READY! New Construction is a VERY rare fin...	4 beds \| 3 baths \| 2,307 sq.ft.	$699,990	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.51% Airbnb Rental Income: $5007 Traditional Rental Income: $3152 Airbnb ROI: 4.78% Traditional ROI: 3.51%
1408 LAKE SHADOW CIRCLE #1207 Maitland, FL Discover Florida comfort and style in this stunning 2-bedroom, 2-bathroom condominium, per...	2 beds \| 2 baths \| 1,111 sq.ft.	$218,999	Airbnb cash on cash: 4.69% Traditional cash on cash: 4.09% Airbnb Rental Income: $2379 Traditional Rental Income: $1670 Airbnb ROI: 4.69% Traditional ROI: 4.09%
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%
326 BANYAN DRIVE Maitland, FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated home. ...	4 beds \| 3 baths \| 2,538 sq.ft.	$465,000	Airbnb cash on cash: 7.35% Traditional cash on cash: 6.97% Airbnb Rental Income: $5007 Traditional Rental Income: $3818 Airbnb ROI: 7.35% Traditional ROI: 6.97%
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.	$750,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 1.78% Airbnb Rental Income: $5007 Traditional Rental Income: $2352 Airbnb ROI: 4.11% Traditional ROI: 1.78%
502 LISA LANE Maitland, FL One or more photo(s) has been virtually staged. PHENONINAL PRICE REDUCTION. SELLERS ARE MO...	4 beds \| 3 baths \| 2,552 sq.ft.	$725,900	Airbnb cash on cash: 4.3% Traditional cash on cash: 3.13% Airbnb Rental Income: $5007 Traditional Rental Income: $3192 Airbnb ROI: 4.3% Traditional ROI: 3.13%
824 PARK LAKE PLACE #824 Maitland, FL Motivated seller...Appraised to sell! New kitchen cabinets. Welcome to your new home in th...	2 beds \| 3 baths \| 1,768 sq.ft.	$260,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 6.11% Airbnb Rental Income: $2379 Traditional Rental Income: $2479 Airbnb ROI: 3.32% Traditional ROI: 6.11%
1627 GULFVIEW DRIVE #441-B Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ex...	3 beds \| 3 baths \| 1,328 sq.ft.	$268,499	Airbnb cash on cash: 6.68% Traditional cash on cash: 4.14% Airbnb Rental Income: $3440 Traditional Rental Income: $2034 Airbnb ROI: 6.68% Traditional ROI: 4.14%
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.	$575,000	Airbnb cash on cash: 5.31% Traditional cash on cash: 2.82% Airbnb Rental Income: $5007 Traditional Rental Income: $2647 Airbnb ROI: 5.31% Traditional ROI: 2.82%
641 LAKE CATHERINE DRIVE Maitland, FL Nestled on the shore of Lake Catherine, this light-infused modern pool home was built in 2...	5 beds \| 6 baths \| 5,810 sq.ft.	$2,495,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 0.85% Airbnb Rental Income: $5533 Traditional Rental Income: $7238 Airbnb ROI: -0.37% Traditional ROI: 0.85%
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: 8.81% Traditional cash on cash: 7.58% Airbnb Rental Income: $3440 Traditional Rental Income: $2361 Airbnb ROI: 8.81% Traditional ROI: 7.58%
130 NOTTOWAY TRAIL Maitland, FL $100,000.00 PRICE REDUCTION: 4-BEDROOM, 3-FULL BATH, LARGE POOL & LAKEFRONT HOME IN MAITLA...	4 beds \| 3 baths \| 2,982 sq.ft.	$698,100	Airbnb cash on cash: 4.67% Traditional cash on cash: 4.73% Airbnb Rental Income: $5007 Traditional Rental Income: $4019 Airbnb ROI: 4.67% Traditional ROI: 4.73%
1912 BELFORD COURT Maitland, FL Attractively priced! Beautiful custom built SINGLE STORY Mediterranean home nestled at th...	5 beds \| 4 baths \| 4,266 sq.ft.	$1,299,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 2.04% Airbnb Rental Income: $5533 Traditional Rental Income: $4842 Airbnb ROI: 1.69% Traditional ROI: 2.04%
1000 S ORLANDO AVENUE #A5 Maitland, FL Million $$ views from first floor unit in charming 3-story mid-century 38 unit community o...	2 beds \| 2 baths \| 952 sq.ft.	$325,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 3.72% Airbnb Rental Income: $2379 Traditional Rental Income: $1908 Airbnb ROI: 3.34% Traditional ROI: 3.72%
1415 CARING COURT Maitland, FL One or more photo(s) has been virtually staged. Exquisite Mediterranean inspired nestled i...	3 beds \| 3 baths \| 2,110 sq.ft.	$639,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 2.22% Airbnb Rental Income: $3440 Traditional Rental Income: $2978 Airbnb ROI: 1.72% Traditional ROI: 2.22%
1030 GREGORY DRIVE Maitland, FL Welcome to this stunning 5-bedroom, 2.5-bathroom mid-century gem! Boasting 2,289 sq ft of ...	5 beds \| 3 baths \| 2,289 sq.ft.	$625,000	Airbnb cash on cash: 5.63% Traditional cash on cash: 4.69% Airbnb Rental Income: $5533 Traditional Rental Income: $3872 Airbnb ROI: 5.63% Traditional ROI: 4.69%
1140 S ORLANDO AVENUE #E-1 Maitland, FL RARE opportunity to buyin the Premier Lake Maitland Terrace CONDO Community. Even more RAR...	2 beds \| 1 baths \| 816 sq.ft.	$249,900	Airbnb cash on cash: 3.59% Traditional cash on cash: 3.76% Airbnb Rental Income: $2379 Traditional Rental Income: $1834 Airbnb ROI: 3.59% Traditional ROI: 3.76%
138 STONE HILL DRIVE Maitland, FL Under contract-accepting backup offers. This stunning 5-bedroom, 4-bath pool home is locat...	5 beds \| 4 baths \| 4,255 sq.ft.	$1,395,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.74% Airbnb Rental Income: $5533 Traditional Rental Income: $5082 Airbnb ROI: 1.23% Traditional ROI: 1.74%
2109 FALKNER ROAD Maitland, FL BACK ON THE MARKET AT THE SAME GREAT PRICE, BUT BETTER THAN EVER! This FULLY REFRESHED 3-B...	3 beds \| 2 baths \| 1,822 sq.ft.	$420,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 3.49% Airbnb Rental Income: $3440 Traditional Rental Income: $2354 Airbnb ROI: 4.31% Traditional ROI: 3.49%
2260 GILLIS COURT Maitland, FL 2260 Gillis Ct, located in the highly desirable and sought-after Dommerich community on on...	4 beds \| 2 baths \| 1,894 sq.ft.	$709,900	Airbnb cash on cash: 4.55% Traditional cash on cash: 2.49% Airbnb Rental Income: $5007 Traditional Rental Income: $2619 Airbnb ROI: 4.55% Traditional ROI: 2.49%
1930 ROGERS AVENUE Maitland, FL WELCOME HOME to 1930 Rogers Avenue in sunny Maitland, Florida! This newly constructed mast...	3 beds \| 2 baths \| 1,625 sq.ft.	$420,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 5.54% Airbnb Rental Income: $3440 Traditional Rental Income: $2725 Airbnb ROI: 5.42% Traditional ROI: 5.54%
2672 TUSCARORA TRAIL Maitland, FL EXTENDED CONCRETE PAD - BRING YOUR RV's AND BOATS!! Located just minutes from the fine di...	4 beds \| 2 baths \| 2,059 sq.ft.	$605,000	Airbnb cash on cash: 5.49% Traditional cash on cash: 3.77% Airbnb Rental Income: $5007 Traditional Rental Income: $3009 Airbnb ROI: 5.49% Traditional ROI: 3.77%
1990 KENASTON ROAD #1990 Maitland, FL Prepare to fall in love with this gorgeous Maitland townhome-style unit, complete with all...	3 beds \| 3 baths \| 1,696 sq.ft.	$420,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 4.2% Airbnb Rental Income: $3440 Traditional Rental Income: $2287 Airbnb ROI: 5.19% Traditional ROI: 4.2%
1000 S ORLANDO AVENUE #A - 6 Maitland, FL One or more photo(s) has been virtually staged. Welcome to Maitland Harbour, your dream la...	2 beds \| 2 baths \| 952 sq.ft.	$395,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 3.76% Airbnb Rental Income: $2379 Traditional Rental Income: $2229 Airbnb ROI: 2.59% Traditional ROI: 3.76%
1100 LAKE SHADOW CIRCLE #2101 Maitland, FL The community features 2 swimming pools, a gym, tennis and basketball courts, and beautifu...	2 beds \| 2 baths \| 1,111 sq.ft.	$228,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 3.29% Airbnb Rental Income: $2379 Traditional Rental Income: $1626 Airbnb ROI: 4.06% Traditional ROI: 3.29%
440 BANYON TREE CIRCLE #102 Maitland, FL Centrally located updated condo, in close proximity to winter park, shopping, and restaura...	2 beds \| 2 baths \| 1,206 sq.ft.	$205,000	Airbnb cash on cash: 7% Traditional cash on cash: 6.34% Airbnb Rental Income: $2379 Traditional Rental Income: $1665 Airbnb ROI: 7% Traditional ROI: 6.34%
2019 LEGACY PALMS DRIVE #2019 Maitland, FL Located in Maitlandâs highly sought after Visconti community this WATER VIEW, TURN-KEY, ...	2 beds \| 2 baths \| 1,280 sq.ft.	$289,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 4.55% Airbnb Rental Income: $2379 Traditional Rental Income: $1853 Airbnb ROI: 4.33% Traditional ROI: 4.55%
101 HOLLIE COURT Maitland, FL This hidden gem of a neighborhood, in the heart of Maitland, has deeded lake access to the...	2 beds \| 2 baths \| 1,545 sq.ft.	$540,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 2.7% Airbnb Rental Income: $2379 Traditional Rental Income: $2244 Airbnb ROI: 1.8% Traditional ROI: 2.7%

Real Estate investment in Maitland, FL

There are 69 properties for sale in the city of Maitland . The median list price in Maitland is $430,000 and the average price per square foot is $215. In November 2024, the average monthly cash on cash return in Maitland is 4.00%. The average monthly rental income in Maitland is $2,354.

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

There are 69 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 $3,440.

Your search for investment property begins and ends here

Investment Property for Sale in Maitland, FL

1521 OXFORD ROAD

Maitland, FL

4 beds | 2 baths | 1,925 sq.ft.

$489,900

Airbnb cash on cash: 6.56%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $5007

Traditional Rental Income: $2826

Airbnb ROI: 6.56%

Traditional ROI: 4.04%

1020 TUCKASEEGEE TRAIL

Maitland, FL

5 beds | 4 baths | 2,603 sq.ft.

$1,034,999

Airbnb cash on cash: 2.85%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $5533

Traditional Rental Income: $4986

Airbnb ROI: 2.85%

Traditional ROI: 3.44%

1800 KING ARTHUR CIRCLE

Maitland, FL

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

$1,040,000

Airbnb cash on cash: 1.93%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $5007

Traditional Rental Income: $3615

Airbnb ROI: 1.93%

Traditional ROI: 1.55%

1501 Oranole Road

Maitland, FL

3 beds | 3 baths | 2,807 sq.ft.

$799,000

Airbnb cash on cash: 1.81%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3440

Traditional Rental Income: $3117

Airbnb ROI: 1.81%

Traditional ROI: 2.4%

2161 LAKE HOWELL PRESERVE COURT

Maitland, FL

3 beds | 4 baths | 2,188 sq.ft.

$614,000

Airbnb cash on cash: 1.48%

Traditional cash on cash: 2.27%

Airbnb Rental Income: $3440

Traditional Rental Income: $3133

Airbnb ROI: 1.48%

Traditional ROI: 2.27%

320 EATON STREET

Maitland, FL

2 beds | 1 baths | 846 sq.ft.

$249,000

Airbnb cash on cash: 5.81%

Traditional cash on cash: 4.99%

Airbnb Rental Income: $2379

Traditional Rental Income: $1603

Airbnb ROI: 5.81%

Traditional ROI: 4.99%

514 WIGMAN DRIVE

Maitland, FL

3 beds | 2 baths | 1,148 sq.ft.

$359,000

Airbnb cash on cash: 5.54%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $3440

Traditional Rental Income: $1911

Airbnb ROI: 5.54%

Traditional ROI: 3.26%

956 STONEWOOD LANE

Maitland, FL

5 beds | 3 baths | 2,837 sq.ft.

$750,000

Airbnb cash on cash: 4.27%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $5533

Traditional Rental Income: $3436

Airbnb ROI: 4.27%