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 |
|---|---|---|---|
140 Wigwam PlMaitland, FLVirtually Staged. Tucked away on a cul-de-sac in beautiful Maitland, this 3-bedroom, 3-bat... |
3 beds | 3 baths | 2,236 sq.ft. |
$599,900 |
Airbnb cash on cash: 1.65%
|
766 TERRA PLACEMaitland, FLUnder contract-accepting backup offers. Virtually Staged. Private Pool Retreat with Two Pr... |
4 beds | 5 baths | 3,040 sq.ft. |
$1,149,900 |
Airbnb cash on cash: 1.49%
|
448 Stonewood LnMaitland, FLOne or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-b... |
4 beds | 3 baths | 3,308 sq.ft. |
$599,900 |
Airbnb cash on cash: 3.08%
|
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. |
$975,000 |
Airbnb cash on cash: 0.42%
|
220 Adams DrMaitland, FLWelcome to 220 Adams Drive â a breathtaking, completely remodeled single-story masterpie... |
4 beds | 3 baths | 3,005 sq.ft. |
$1,995,000 |
Airbnb cash on cash: 0.09%
|
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: 4.41%
|
550 FLEMMING WAY #100Maitland, FLBright and well maintained 2 bedroom, 1 bath condo located in a desirable shopping and din... |
2 beds | 1 baths | 1,051 sq.ft. |
$139,000 |
Airbnb cash on cash: 2.22%
|
631 Lake Catherine DrMaitland, 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: -0.52%
|
1150 Lake Shadow Circle #3307Maitland, FLWelcome to Visconti, one of Central Florida's most sought-after gated communities. This st... |
2 beds | 2 baths | 1,111 sq.ft. |
$250,000 |
Airbnb cash on cash: 0.9%
|
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: 4.53%
|
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: 2.02%
|
1511 E Horatio AveMaitland, 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: 3.3%
|
2697 QUEEN MARY PLACEMaitland, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Th... |
3 beds | 2 baths | 1,558 sq.ft. |
$520,000 |
Airbnb cash on cash: 1.31%
|
2155 FENNELL STREETMaitland, FLWelcome to 2155 Fennell Street, a beautifully renovated pool home nestled in the desirable... |
3 beds | 2 baths | 1,822 sq.ft. |
$489,900 |
Airbnb cash on cash: 2.62%
|
1074 Hamlet DrMaitland, 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: 4.99%
|
1000 S ORLANDO AVENUE #A31Maitland, FLExperience the best of lakeside living in this beautifully updated third-floor corner resi... |
2 beds | 2 baths | 952 sq.ft. |
$300,000 |
Airbnb cash on cash: -0.07%
|
67 CYPRESS LANEMaitland, FLUnder contract-accepting backup offers. Welcome to 67 Cypress Lane, a stunning single-owne... |
4 beds | 3 baths | 2,292 sq.ft. |
$999,000 |
Airbnb cash on cash: 2.3%
|
1100 S Orlando Ave #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: -1.85%
|
1130 Mechanic StMaitland, FLPre-Construction. To be built. Come build your dream home on this exceptional homesite in ... |
4 beds | 4 baths | 3,567 sq.ft. |
$1,800,000 |
Airbnb cash on cash: 1.03%
|
51 Oakleigh LnMaitland, FLCome see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comf... |
4 beds | 4 baths | 4,149 sq.ft. |
$1,110,000 |
Airbnb cash on cash: 1.79%
|
1111 Audubon WayMaitland, FLWelcome to a rare opportunity on the shores of Lake Sybelia, one of Maitlandâs most desi... |
4 beds | 3 baths | 3,754 sq.ft. |
$1,825,000 |
Airbnb cash on cash: 0.29%
|
570 DOMMERICH DRIVEMaitland, FLUnder contract-accepting backup offers. Virtually Staged. ONE OF A KIND for Dommerich Esta... |
4 beds | 3 baths | 2,956 sq.ft. |
$795,000 |
Airbnb cash on cash: 2.97%
|
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: 0.57%
|
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: 1.92%
|
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. |
$450,000 |
Airbnb cash on cash: 6.74%
|
1750 Pocahontas PathMaitland, FLSet along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,9... |
3 beds | 2 baths | 1,922 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.61%
|
210 ALPINE DRIVEMaitland, FLDon't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for ... |
2 beds | 3 baths | 1,328 sq.ft. |
$527,300 |
Airbnb cash on cash: -0.01%
|
551 Ruffel StMaitland, FLSituated at the end of a cul-de-sac in the Eatonville/Maitland area, this home offers a gr... |
3 beds | 1 baths | 1,162 sq.ft. |
$278,500 |
Airbnb cash on cash: 5.6%
|
1776 Bobtail DrMaitland, FLWelcome to 1776 Bobtail Drive â the kind of home that doesnât just check boxes⦠it c... |
4 beds | 3 baths | 2,344 sq.ft. |
$519,999 |
Airbnb cash on cash: 5.58%
|
2130 Deloraine TrlMaitland, FLWelcome to this beautifully renovated pool home in the highly sought-after Dommerich neigh... |
3 beds | 2 baths | 2,175 sq.ft. |
$779,000 |
Airbnb cash on cash: 0.26%
|
1100 Lake Shadow Cir #2307Maitland, FLVirtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in th... |
2 beds | 2 baths | 1,111 sq.ft. |
$190,000 |
Airbnb cash on cash: 0.47%
|
987 Brightwater CirMaitland, FLYour dream home awaits. Welcome to this exquisitely Renovated 4/4 PLUS OFFICE PLUS BONUS ... |
5 beds | 4 baths | 3,270 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 1.16%
|
1000 WINDERLEY PLACE #226Maitland, FL***PRICE IMPROVEMENT***Welcome to this beautifully maintained 3-bedroom, 2-bath condo loca... |
3 beds | 2 baths | 1,538 sq.ft. |
$315,000 |
Airbnb cash on cash: 3.03%
|
1244 E Lake Colony DrMaitland, FLModern, mediterranean lakefront residence in one of Maitlandâs most desirable GATED comm... |
4 beds | 5 baths | 4,478 sq.ft. |
$1,790,000 |
Airbnb cash on cash: -0.12%
|
1511 Glastonberry RdMaitland, FLThis AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neigh... |
5 beds | 3 baths | 2,376 sq.ft. |
$549,000 |
Airbnb cash on cash: 6.05%
|
873 Cranes CtMaitland, FLBeautifully Maintained Original-Owner Pool Home in Gated Lake Sybelia Cove. Pride of ow... |
4 beds | 4 baths | 3,902 sq.ft. |
$1,224,900 |
Airbnb cash on cash: 1.1%
|
444 BANYON TREE CIRCLE #202Maitland, FLBeautifully well-maintained 3 bedroom, 2 bathroom condo located in the desirable Maitland ... |
3 beds | 2 baths | 1,428 sq.ft. |
$239,900 |
Airbnb cash on cash: 3.63%
|
814 Park Lake Cir #8Maitland, FLA beautiful affordable condo in Maitland. 2 bedrooms and 1 ½ baths with a 1 car garage. T... |
2 beds | 1 baths | 1,432 sq.ft. |
$215,000 |
Airbnb cash on cash: 1%
|
9001 Lake Charity DrMaitland, FLWelcome to a rare opportunity in the beautiful neighborhood of Druid Hills in Maitlandât... |
3 beds | 2 baths | 1,623 sq.ft. |
$575,000 |
Airbnb cash on cash: 2.21%
|
910 GAMEWELL AVENUEMaitland, FLTucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath re... |
3 beds | 2 baths | 2,214 sq.ft. |
$645,000 |
Airbnb cash on cash: 1.34%
|
Real Estate investment in Maitland, FL
There are 86 properties for sale in the city of Maitland . The median list price in Maitland is $542,176 and the average price per square foot is $255. In July 2026, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,587.