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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
195 E FAITH TERRACEMaitland, FLUnder contract-accepting backup offers. Perfectly positioned on the tranquil shores of Lak... |
3 beds | 2 baths | 2,502 sq.ft. |
$825,000 |
Airbnb cash on cash: 1.58%
|
2517 CAPER LANE #207Maitland, FLOne or more photo(s) has been virtually staged. Charming 1 Bedroom, 1 Bathroom condo in be... |
1 beds | 1 baths | 550 sq.ft. |
$114,000 |
Airbnb cash on cash: 9.12%
|
1375 LAKE SHADOW CIRCLE #11208Maitland, FLStep 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%
|
500 BANYON TREE CIRCLE #104Maitland, FLOne or more photo(s) has been virtually staged. Welcome to this beautifully renovated 3-be... |
3 beds | 2 baths | 1,428 sq.ft. |
$199,999 |
Airbnb cash on cash: 8.04%
|
515 W FAITH TERRACEMaitland, FLBeautiful Mid-Century Modern in Maitland! Sylish 3-bed, 2-bath, single-story home with 2-c... |
3 beds | 2 baths | 2,205 sq.ft. |
$515,000 |
Airbnb cash on cash: 3.4%
|
1140 South Orlando Avenue #E-11Maitland, FLRare Opportunity for Lakeside Living! This beautifully maintained 1-bedroom, 1-bath, 612 s... |
1 beds | 1 baths | 612 sq.ft. |
$210,000 |
Airbnb cash on cash: 4.45%
|
2525 CAPER LANE #205Maitland, FLCondo 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%
|
1655 SUNNYSIDE DRIVEMaitland, FLWelcome to 1655 Sunnyside Drive, a beautifully charming home nestled on a picturesque corn... |
3 beds | 2 baths | 1,418 sq.ft. |
$725,000 |
Airbnb cash on cash: 1.5%
|
708 THUNDER TRAILMaitland, FLWelcome 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%
|
249 SPARTAN DRIVEMaitland, FLDiscover Your Perfect Maitland Retreat! Tucked away on a quiet dead-end street, this deli... |
4 beds | 2 baths | 1,579 sq.ft. |
$345,000 |
Airbnb cash on cash: 9.75%
|
1000 WINDERLEY PLACE #128Maitland, FLImmaculate 2BR/2BA Condo in a Gated Maitland Community. - Spacious and well maintained 2-b... |
2 beds | 2 baths | 1,275 sq.ft. |
$267,900 |
Airbnb cash on cash: 0.21%
|
1000 WINDERLEY PLACE #222Maitland, FLDiscover Sun Bay Club â Maitlandâs Hidden Gem on Lake Destiny! Behind the signature b... |
2 beds | 2 baths | 1,164 sq.ft. |
$309,000 |
Airbnb cash on cash: 3.79%
|
1460 LAKE SHADOW CIRCLE #7204Maitland, FLResort style living in this sought after gated community located near the Maitland Exchang... |
3 beds | 2 baths | 1,243 sq.ft. |
$219,900 |
Airbnb cash on cash: 7.64%
|
214 CHERRYWOOD DRIVEMaitland, FLOne 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%
|
920 PARK LAKE CIRCLE #36Maitland, FLWelcome to 920 Park Lake Circle in charming Maitland, FL â a beautifully updated 3 bedro... |
3 beds | 3 baths | 1,486 sq.ft. |
$269,000 |
Airbnb cash on cash: 7.9%
|
2352 SIERRA LANE #2352Maitland, FLUnder contract-accepting backup offers. Experience the comfort and convenience of living i... |
3 beds | 2 baths | 1,343 sq.ft. |
$340,000 |
Airbnb cash on cash: 3.24%
|
135 Roosevelt PlaceMaitland, FLThis charming home boasts a wealth of valuable upgrades and improvements, making it an ent... |
4 beds | 2 baths | 2,426 sq.ft. |
$564,900 |
Airbnb cash on cash: 5.37%
|
113 GEM LAKE DRIVEMaitland, FLMust 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%
|
1511 E HORATIO AVENUEMaitland, FLWelcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, ... |
4 beds | 3 baths | 2,676 sq.ft. |
$719,900 |
Airbnb cash on cash: 3.95%
|
1140 S ORLANDO AVENUE #E-1Maitland, FLOne or more photo(s) has been virtually staged. RARE opportunity to live in the Premier La... |
2 beds | 1 baths | 816 sq.ft. |
$209,900 |
Airbnb cash on cash: 4.44%
|
1231 SIDCUP ROADMaitland, FLPrepare to be captivated by this fully renovated gem located in the highly sought after En... |
3 beds | 2 baths | 1,798 sq.ft. |
$545,000 |
Airbnb cash on cash: 3.76%
|
206 QUAYSIDE CIRCLE #404Maitland, FLWelcome to The Moorings, a rarely available lakeside community perfectly positioned across... |
2 beds | 2 baths | 1,270 sq.ft. |
$590,000 |
Airbnb cash on cash: 0.66%
|
380 BANYAN DRIVEMaitland, FLCharming 3BR/2BA Home with Updated Interior This move-in ready home features 3 bedrooms... |
3 beds | 2 baths | 1,404 sq.ft. |
$429,000 |
Airbnb cash on cash: 5.16%
|
255 W GEORGE AVENUEMaitland, FLExperience 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%
|
2329 SHADOW VIEW CIRCLE #2329Maitland, FLWelcome to this stunning, fully renovated 3-Bedroom, 2.5-Bath home located in the desirab... |
3 beds | 3 baths | 1,583 sq.ft. |
$320,000 |
Airbnb cash on cash: 4.45%
|
385 LIME STREETMaitland, FLWonderful investment opportunity in historic Eatonville. Large corner lot. Roof was replac... |
4 beds | N/A baths | 1,680 sq.ft. |
$419,900 |
Airbnb cash on cash: 4.89%
|
1913 POINSETTA LANEMaitland, FLMotivated Seller! Stunningly Renovated 4-Bedroom Home in Prime Maitland Seize this rare op... |
4 beds | 2 baths | 1,664 sq.ft. |
$424,900 |
Airbnb cash on cash: 8.41%
|
1325 LAKE SHADOW CIRCLE #12303Maitland, FLUnder contract-accepting backup offers. Welcome to carefree living in the sought-after Vis... |
2 beds | 2 baths | 1,048 sq.ft. |
$215,000 |
Airbnb cash on cash: 4.37%
|
2632 DERBYSHIRE ROADMaitland, 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. |
$555,000 |
Airbnb cash on cash: 5.7%
|
1135 THUNDER TRAILMaitland, FLDistinctive Dommerich Hills Home with Flexible Floor Plan and Modern Upgrades. Welcom... |
4 beds | 4 baths | 2,651 sq.ft. |
$619,000 |
Airbnb cash on cash: 4.87%
|
736 FOREST GLEN COURTMaitland, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Ne... |
4 beds | 2 baths | 1,647 sq.ft. |
$479,899 |
Airbnb cash on cash: 6.62%
|
1277 BLESSING STREETMaitland, FLThis 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%
|
1745 E ADAMS DRIVEMaitland, FLClassic Colonial Brick Home on highly desired E Adama Drive across from Lake Maitland! 4 ... |
4 beds | 4 baths | 2,378 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 1.31%
|
2155 FENNELL STREETMaitland, FLBack 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%
|
1140 S ORLANDO AVENUE #I-5Maitland, FLBe the first to explore this brand new to the market, first time available in years. Disc... |
2 beds | 1 baths | 816 sq.ft. |
$170,000 |
Airbnb cash on cash: 5.62%
|
2491 LAUDER DRIVEMaitland, FLUnder contract-accepting backup offers. Nestled on a spacious corner lot in the highly sou... |
5 beds | 3 baths | 2,695 sq.ft. |
$650,000 |
Airbnb cash on cash: 4.69%
|
449 FORESTWOOD LANEMaitland, FLâBack on the market due to buyer financing. No fault of the seller.â STONEWOOD. This ... |
4 beds | 2 baths | 2,532 sq.ft. |
$550,000 |
Airbnb cash on cash: 5.15%
|
832 PARK LAKE PL #6AMaitland, FLUnder contract-accepting backup offers. HUGE SAVINGS: Seller will pay ONE YEAR of HOA dues... |
2 beds | 3 baths | 1,732 sq.ft. |
$224,500 |
Airbnb cash on cash: 3.4%
|
1024 KEWANNEE TRAILMaitland, FLOne or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed ... |
4 beds | 3 baths | 1,845 sq.ft. |
$629,000 |
Airbnb cash on cash: 4.29%
|
1074 HAMLET DRIVEMaitland, FLWelcome 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: 7.35%
|
Real Estate investment in Maitland, FL
There are 68 properties for sale in the city of Maitland . The median list price in Maitland is $429,450 and the average price per square foot is $248. In December 2025, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,295.