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 |
|---|---|---|---|
1065 GREGORY DRMaitland, FLVIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home features 3 bed/2 bath in the main ho... |
4 beds | 2 baths | 1,929 sq.ft. |
$519,000 |
Airbnb cash on cash: 5.93%
|
140 WIGWAM PLACEMaitland, FLOne or more photo(s) has been virtually staged. Tucked away on a cul-de-sac in beautiful M... |
3 beds | 3 baths | 2,236 sq.ft. |
$629,900 |
Airbnb cash on cash: 2.77%
|
790 S LAKE SYBELIA DRIVEMaitland, FLOne or more photo(s) has been virtually staged. Price Improvement! A must See rare opportu... |
3 beds | 3 baths | 2,021 sq.ft. |
$960,000 |
Airbnb cash on cash: 1.18%
|
824 TOWN CIRCLE #101Maitland, FLMove-in ready two story townhome. This beautifully updated 3 bd 2.5 ba corner unit is loca... |
3 beds | 3 baths | 1,565 sq.ft. |
$264,990 |
Airbnb cash on cash: 6.1%
|
766 TERRA PLACEMaitland, FLOne or more photo(s) has been virtually staged. Private Pool Retreat with Two Primary Suit... |
4 beds | 5 baths | 3,040 sq.ft. |
$1,149,900 |
Airbnb cash on cash: 1.89%
|
221 MINNEHAHA ROADMaitland, FLUnder contract-accepting backup offers. A rare opportunity on one of Maitlandâs most cov... |
4 beds | 3 baths | 3,797 sq.ft. |
$1,489,000 |
Airbnb cash on cash: 1.07%
|
448 STONEWOOD LANEMaitland, FLOne or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-b... |
4 beds | 3 baths | 3,308 sq.ft. |
$624,990 |
Airbnb cash on cash: 3.82%
|
361 HICKORY DRIVEMaitland, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. We... |
3 beds | 2 baths | 1,407 sq.ft. |
$349,000 |
Airbnb cash on cash: 6.12%
|
755 WOODSIDE ROADMaitland, FLThis 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. |
$999,999 |
Airbnb cash on cash: 1.12%
|
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, FLThis bright and inviting second floor condo offers an abundance of natural light throughou... |
1 beds | 1 baths | 550 sq.ft. |
$119,000 |
Airbnb cash on cash: 6.49%
|
631 LAKE CATHERINE DRIVEMaitland, FLWelcome 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: -0.11%
|
200 SPARTAN DRIVEMaitland, FLMore photos to come soon! Welcome to 200 Spartan Dr, a beautifully updated 3/2 (with bonus... |
3 beds | 2 baths | 1,830 sq.ft. |
$525,000 |
Airbnb cash on cash: 2.61%
|
1770 ALGONQUIN TRAILMaitland, FLWelcome to 1770 Algonquin Trail â where modern upgrades, thoughtful renovations, and Flo... |
4 beds | 2 baths | 1,689 sq.ft. |
$700,000 |
Airbnb cash on cash: 4.1%
|
2642 BROOKSIDE COURTMaitland, FLIndulge 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: 5.43%
|
612 GREEN MEADOW AVENUEMaitland, FLUnder 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: 3.52%
|
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. |
$719,000 |
Airbnb cash on cash: 3.95%
|
2697 QUEEN MARY PLACEMaitland, FLOne or more photo(s) has been virtually staged. This gem is situated in the Brittney Garde... |
3 beds | 2 baths | 1,558 sq.ft. |
$520,000 |
Airbnb cash on cash: 2.72%
|
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%
|
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%
|
223 QUAYSIDE CIRCLE #CMaitland, FLWelcome to refined living in The Moorings! This beautifully updated 3-bedroom, 2.5-bath to... |
3 beds | 3 baths | 1,734 sq.ft. |
$545,000 |
Airbnb cash on cash: 1.39%
|
353 W LAKE FAITH DRIVE #116Maitland, FLDiscover lakeside living at its finest in this beautifully updated 2nd-floor, private lake... |
2 beds | 2 baths | 1,403 sq.ft. |
$344,900 |
Airbnb cash on cash: 1.76%
|
2065 DERBYSHIRE ROADMaitland, FLUnder contract-accepting backup offers. Beautifully renovated and move-in ready, this 3-be... |
3 beds | 2 baths | 1,430 sq.ft. |
$449,990 |
Airbnb cash on cash: 4.78%
|
67 CYPRESS LANEMaitland, FLWelcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majesti... |
4 beds | 3 baths | 2,292 sq.ft. |
$999,000 |
Airbnb cash on cash: 2.76%
|
1100 S ORLANDO AVENUE #956Maitland, FLLAKEFRONT - Enjoy condo living at its finest from the top-floor Lake Maitland penthouse wi... |
2 beds | 2 baths | 1,685 sq.ft. |
$795,000 |
Airbnb cash on cash: -1.09%
|
1130 MECHANIC STREETMaitland, FLPre-Construction. To be built. Come build your dream home on this exceptional homesite in ... |
4 beds | 5 baths | 3,567 sq.ft. |
$1,800,000 |
Airbnb cash on cash: 1.29%
|
2570 DERBYSHIRE BOULEVARDMaitland, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. We... |
4 beds | 3 baths | 1,857 sq.ft. |
$545,000 |
Airbnb cash on cash: 6.29%
|
312 MACARTHUR PLACEMaitland, FLUnder contract-accepting backup offers. NEW ROOF, NEWER AC, and NO HOAâthis beautifully ... |
3 beds | 3 baths | 2,441 sq.ft. |
$774,900 |
Airbnb cash on cash: 1.43%
|
51 OAKLEIGH LANEMaitland, FLCome see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comf... |
4 beds | 4 baths | 4,149 sq.ft. |
$1,175,000 |
Airbnb cash on cash: 2.09%
|
1140 S ORLANDO AVENUE #F-1Maitland, FLUnder contract-accepting backup offers. This condo was completely renovated in 2023 and is... |
2 beds | 2 baths | 816 sq.ft. |
$385,000 |
Airbnb cash on cash: 1.15%
|
1256 WELLINGTON TERRACEMaitland, FLUnder contract-accepting backup offers. HARD TO FIND SKI LAKEFRONT! Classic traditional b... |
5 beds | 5 baths | 4,280 sq.ft. |
$1,250,000 |
Airbnb cash on cash: 1.64%
|
1111 AUDUBON WAYMaitland, FLWelcome to a rare opportunity on the shores of Lake Sybelia, one of Maitlandâs most desi... |
4 beds | 4 baths | 3,754 sq.ft. |
$1,825,000 |
Airbnb cash on cash: 0.54%
|
250 ORANGE PLACEMaitland, FLUnder contract-accepting backup offers. Welcome to 250 Orange Place, This charming bungalo... |
1 beds | 1 baths | 564 sq.ft. |
$325,000 |
Airbnb cash on cash: 1.89%
|
570 DOMMERICH DRIVEMaitland, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. ON... |
4 beds | 3 baths | 2,956 sq.ft. |
$875,000 |
Airbnb cash on cash: 3.15%
|
220 ALPINE DRIVEMaitland, FLOpportunity 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: 1.96%
|
535 PAWNEE TRAILMaitland, FLUnder 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: 2.43%
|
106 OAKWOOD DRIVEMaitland, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. FI... |
3 beds | 2 baths | 1,877 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.97%
|
1000 S ORLANDO AVENUE #B25Maitland, FLUnder contract-accepting backup offers. Offered at a newly improved price, this highly des... |
2 beds | 2 baths | 952 sq.ft. |
$332,500 |
Airbnb cash on cash: 1.54%
|
150 SENECA TRAILMaitland, FLUnder contract-accepting backup offers. In the heart of Dommerich, this thoughtfully renov... |
4 beds | 3 baths | 2,221 sq.ft. |
$745,000 |
Airbnb cash on cash: 3.18%
|
623 GREEN MEADOW AVENUEMaitland, FLWelcome to this beautifully maintained two-owner concrete block home offering the perfect ... |
4 beds | 2 baths | 1,909 sq.ft. |
$500,000 |
Airbnb cash on cash: 6.91%
|
Real Estate investment in Maitland, FL
There are 72 properties for sale in the city of Maitland . The median list price in Maitland is $565,000 and the average price per square foot is $272. In June 2026, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,736.