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 |
|---|---|---|---|
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. |
$120,000 |
Airbnb cash on cash: 8.64%
|
1521 OXFORD ROADMaitland, FLUnder contract-accepting backup offers. Welcome to 1521 Oxford Rd - here's your opportunit... |
4 beds | 2 baths | 1,925 sq.ft. |
$468,900 |
Airbnb cash on cash: 6.9%
|
1000 WINDERLEY PLACE #122Maitland, FLUnder contract-accepting backup offers. MOVE-IN READY FIRST-FLOOR OASIS AT SUN BAY CLUB! D... |
2 beds | 2 baths | 1,164 sq.ft. |
$279,000 |
Airbnb cash on cash: 2.28%
|
201 CEDARWOOD DRIVEMaitland, FLWelcome to this beautifully reimagined 3-bedroom, 2-bathroom ranch perfectly positioned on... |
3 beds | 2 baths | 2,200 sq.ft. |
$840,000 |
Airbnb cash on cash: 1.54%
|
162 ORANGE PLACEMaitland, FLThis beautiful 3/2 Maitland home has been meticulously cared for. It boast original hardwo... |
3 beds | 2 baths | 1,624 sq.ft. |
$599,900 |
Airbnb cash on cash: 3.16%
|
824 TOWN CIRCLE #101Maitland, FLMove-in ready two story townhome. This beautifully updated 3 bd 2.5 ba townhome is located... |
3 beds | 3 baths | 1,565 sq.ft. |
$290,000 |
Airbnb cash on cash: 5.65%
|
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. |
$205,000 |
Airbnb cash on cash: 4.38%
|
1400 LAKE SHADOW CIRCLE #10306Maitland, FLUnder contract-accepting backup offers. Wake up to views of the gentle shimmer of Lake Sha... |
1 beds | 1 baths | 672 sq.ft. |
$165,000 |
Airbnb cash on cash: 3.68%
|
2133 KORAT LANEMaitland, FLExceptional Value ** New Reduced price $514,900 ** Great Style, great space, prime loca... |
4 beds | 3 baths | 2,359 sq.ft. |
$514,900 |
Airbnb cash on cash: 5.81%
|
1353 W LAKE COLONY DRIVEMaitland, FLUnder contract-accepting backup offers. Welcome to this custom-built 4 bedroom, 3 bathroom... |
4 beds | 3 baths | 3,500 sq.ft. |
$1,229,000 |
Airbnb cash on cash: 1.18%
|
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. |
$125,000 |
Airbnb cash on cash: 6.18%
|
2162 LAKE HOWELL PRESERVE COURTMaitland, FLThis home does more than check boxes. It tells a story. Minutes from downtown Winter Pa... |
3 beds | 4 baths | 2,188 sq.ft. |
$545,000 |
Airbnb cash on cash: 1.83%
|
505 LAKE SHORE DRIVEMaitland, FLImagine mornings with the sunrise shimmering across Lake Faith, directly across the street... |
4 beds | 2 baths | 2,317 sq.ft. |
$600,000 |
Airbnb cash on cash: 5.58%
|
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. |
$349,900 |
Airbnb cash on cash: 9.6%
|
2047 HOWELL BRANCH ROADMaitland, FLUnder contract-accepting backup offers. The home youâve been searching for has officiall... |
4 beds | 2 baths | 2,960 sq.ft. |
$1,499,000 |
Airbnb cash on cash: 1.1%
|
1434 WINSTON ROADMaitland, FLWelcome to 1434 Winston Road, located in Seminole Countyâs desirable English Estates nei... |
4 beds | 2 baths | 2,312 sq.ft. |
$579,000 |
Airbnb cash on cash: 5.17%
|
1150 LAKE SHADOW CIRCLE #3104Maitland, FLOne or more photo(s) has been virtually staged. SELLER'S PREFERRED LENDER IS OFFERING UP T... |
2 beds | 2 baths | 1,048 sq.ft. |
$230,000 |
Airbnb cash on cash: 3.82%
|
2031 EATON STREETMaitland, FL*2.99% Assumable Mortgage Rate Available* Welcome to 2031 Eaton Street, a modern haven wit... |
4 beds | 3 baths | 2,518 sq.ft. |
$424,000 |
Airbnb cash on cash: 8.07%
|
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. |
$239,900 |
Airbnb cash on cash: 6.93%
|
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. |
$345,000 |
Airbnb cash on cash: 5.96%
|
2350 DERBYSHIRE ROADMaitland, FLUnder contract-accepting backup offers. Thereâs a quiet confidence to this one. The kind... |
4 beds | 2 baths | 2,359 sq.ft. |
$590,000 |
Airbnb cash on cash: 4.82%
|
204 QUAYSIDE CIRCLE #601Maitland, FLUnder contract-accepting backup offers. Here's your chance to own an amazing penthouse con... |
2 beds | 2 baths | 1,270 sq.ft. |
$519,900 |
Airbnb cash on cash: 0.04%
|
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%
|
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. |
$229,900 |
Airbnb cash on cash: 3.97%
|
1994 KENASTON ROAD #1994Maitland, FLNestled in the heart of Maitland, just 3 miles from the charming Park Avenue in Winter Par... |
3 beds | 4 baths | 2,103 sq.ft. |
$439,900 |
Airbnb cash on cash: 4.31%
|
240 PEOPLE STREETMaitland, FLUnder contract-accepting backup offers. Short Sale. Short sale. List price is a bank appro... |
3 beds | 2 baths | 1,287 sq.ft. |
$243,380 |
Airbnb cash on cash: 8.29%
|
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. |
$575,000 |
Airbnb cash on cash: 3.52%
|
1000 WINDERLEY PLACE #7Maitland, FLMaitland's hidden gem! Beauty and serenity at Sun Bay Club in the heart of Maitland's offi... |
3 beds | 4 baths | 1,555 sq.ft. |
$325,000 |
Airbnb cash on cash: 4.47%
|
404 BANYON TREE CIRCLE #200Maitland, FLWelcome 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%
|
2201 SUNDERLAND ROADMaitland, FLWelcome to your beautifully renovated corner-lot oasis in the desirable English Estates co... |
3 beds | 2 baths | 1,798 sq.ft. |
$589,000 |
Airbnb cash on cash: 3.4%
|
1221 THUNDER TRAILMaitland, FLDon't miss out on this AMAZING Maitland home for under $450k! NEW roof in 2023 and HVAC 20... |
3 beds | 2 baths | 1,908 sq.ft. |
$440,000 |
Airbnb cash on cash: 4.75%
|
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. |
$469,000 |
Airbnb cash on cash: 4.64%
|
135 JAMES PLACEMaitland, FLACTIVE on the Market â Enhanced and Priced to Sell! Custom built in 2003 and secluded i... |
5 beds | 5 baths | 3,885 sq.ft. |
$1,599,000 |
Airbnb cash on cash: 1.08%
|
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. |
$1,800,000 |
Airbnb cash on cash: 1.2%
|
711 THOMPSON AVENUEMaitland, FLCome 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%
|
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. |
$325,000 |
Airbnb cash on cash: 4.37%
|
530 RUFFEL STREETMaitland, FLGreat property to add to your investment portfolio. This 3 bed 1 1/2 bath with family room... |
3 beds | 2 baths | 1,449 sq.ft. |
$249,900 |
Airbnb cash on cash: 9.1%
|
385 LIME STREETMaitland, FLWonderful investment opportunity in historic Eatonville. Large corner lot. The roof was re... |
4 beds | N/A baths | 1,680 sq.ft. |
$419,900 |
Airbnb cash on cash: 4.89%
|
1913 POINSETTA LANEMaitland, FLMotivated Seller â Stylishly Renovated 4-Bedroom Home in Prime Maitland Location! Donâ... |
4 beds | 2 baths | 1,664 sq.ft. |
$449,500 |
Airbnb cash on cash: 7.9%
|
705 N LAKE SYBELIA DRIVEMaitland, FLUnder contract-accepting backup offers. Completed New Construction 2024 | Lakefront Luxury... |
5 beds | 4 baths | 3,949 sq.ft. |
$2,485,000 |
Airbnb cash on cash: 0.61%
|
Real Estate investment in Maitland, FL
There are 78 properties for sale in the city of Maitland . The median list price in Maitland is $463,950 and the average price per square foot is $245. In September 2025, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,394.