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. |
$110,000 |
Airbnb cash on cash: 9.47%
|
1301 DRUID ISLE ROADMaitland, FLNestled in the highly desirable Druid Isle neighborhood, this single-family residence offe... |
4 beds | 3 baths | 2,162 sq.ft. |
$649,990 |
Airbnb cash on cash: 4.37%
|
890 CRANES COURTMaitland, FLNestled in the QUIET, oak tree lined and GATED community of LAKE SYBELIA COVE, this CUSTOM... |
4 beds | 4 baths | 3,221 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 1.74%
|
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%
|
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%
|
2270 DELORAINE TRAILMaitland, FLUnder contract-accepting backup offers. This beautifully updated 4-bedroom, 2-bath pool ho... |
4 beds | 2 baths | 2,000 sq.ft. |
$850,000 |
Airbnb cash on cash: 3.07%
|
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. |
$635,000 |
Airbnb cash on cash: 4.3%
|
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%
|
1150 LAKE SHADOW CIRCLE #3104Maitland, FLOne or more photo(s) has been virtually staged. BIG NEWS! THE SELLERâS PREFERRED LENDER ... |
2 beds | 2 baths | 1,048 sq.ft. |
$215,000 |
Airbnb cash on cash: 4.15%
|
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: 2.29%
|
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%
|
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. |
$1,975,000 |
Airbnb cash on cash: -0.19%
|
1460 LAKE SHADOW CIRCLE #7204Maitland, FLOWNER MOTIVATED! PRICED TO SELL!! Resort style living in this sought after gated community... |
3 beds | 2 baths | 1,243 sq.ft. |
$199,900 |
Airbnb cash on cash: 8.48%
|
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%
|
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. |
$699,900 |
Airbnb cash on cash: 4.09%
|
1140 S ORLANDO AVENUE #E-1Maitland, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. RA... |
2 beds | 1 baths | 816 sq.ft. |
$209,900 |
Airbnb cash on cash: 4.44%
|
1994 KENASTON ROAD #1994Maitland, FLLocated in the desirable city of Maitland, just three miles from Winter Parkâs renowned ... |
3 beds | 4 baths | 2,103 sq.ft. |
$415,000 |
Airbnb cash on cash: 4.55%
|
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. |
$535,000 |
Airbnb cash on cash: 3.85%
|
1619 DRUID ROADMaitland, FLTucked into prestigious Maitland Florida on coveted Druid Road, this one-of-a-kind residen... |
5 beds | 4 baths | 3,769 sq.ft. |
$950,000 |
Airbnb cash on cash: 2.73%
|
206 QUAYSIDE CIRCLE #404Maitland, FLWelcome to The Moorings, a rarely available lakeside community perfectly positioned across... |
2 beds | 2 baths | 1,270 sq.ft. |
$570,000 |
Airbnb cash on cash: 0.72%
|
380 BANYAN DRIVEMaitland, FLUnder contract-accepting backup offers. Charming 3BR/2BA Home with Updated Interior Thi... |
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%
|
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. |
$525,000 |
Airbnb cash on cash: 6.08%
|
736 FOREST GLEN COURTMaitland, FLOne or more photo(s) has been virtually staged. Huge Price Reduction!!!!! - Motivated Sell... |
4 beds | 2 baths | 1,647 sq.ft. |
$455,000 |
Airbnb cash on cash: 7.03%
|
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. |
$595,000 |
Airbnb cash on cash: 4.59%
|
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%
|
2318 CASTLEWOOD ROADMaitland, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Yo... |
4 beds | 3 baths | 2,335 sq.ft. |
$580,000 |
Airbnb cash on cash: 5.82%
|
2464 DERBYSHIRE ROADMaitland, FLAuction Property. Welcome to this inviting home offering comfortable living spaces and a t... |
3 beds | 2 baths | 1,860 sq.ft. |
$411,900 |
Airbnb cash on cash: 5.27%
|
1416 CARING COURTMaitland, FLBeautifully maintained Maitland home in the gated community of Montacino on Lake Charity. ... |
4 beds | 4 baths | 3,451 sq.ft. |
$925,000 |
Airbnb cash on cash: 1.84%
|
1140 S ORLANDO AVENUE #16Maitland, FLLovely direct waterfront condominium with large screen porch overlooking beautiful 451 acr... |
2 beds | 1 baths | 816 sq.ft. |
$459,000 |
Airbnb cash on cash: 2.44%
|
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. |
$375,000 |
Airbnb cash on cash: 3.25%
|
1000 WINDERLEY PLACE #142Maitland, FLWake up to water views, an abundance of natural light, and tropical serenity in this beaut... |
3 beds | 2 baths | 1,538 sq.ft. |
$325,000 |
Airbnb cash on cash: 6.72%
|
204 QUAYSIDE CIRCLE #604Maitland, FLPenthouse Living at The Moorings on Lake Maitland â 204 Quayside Cir #604 Welcome to yo... |
2 beds | 2 baths | 1,270 sq.ft. |
$525,000 |
Airbnb cash on cash: 0.55%
|
225 QUAYSIDE CIRCLEMaitland, FLDiscover the perfect blend of style and location in this beautifully updated 3-bedroom, 2.... |
3 beds | 3 baths | 1,734 sq.ft. |
$595,000 |
Airbnb cash on cash: 3.14%
|
Real Estate investment in Maitland, FL
There are 62 properties for sale in the city of Maitland . The median list price in Maitland is $417,450 and the average price per square foot is $247. In January 2026, the average monthly cash on cash return in Maitland is 3.00%. The average monthly rental income in Maitland is $2,214.