Real Estate Investments for Sale in Windermere, FL With High ROI
Are you looking for a vacation rental in Windermere, FL? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.
Explore a variety of short-term homes & houses in Windermere, FL. Invest wisely with VRBO & Windermere, 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 Windermere, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
6306 LITTLE LAKE SAWYER DRIVEWindermere, FLFantastic opportunity to call Windermere's quaint and highly sought after development, Pro... |
4 beds | 3 baths | 2,813 sq.ft. |
$745,000 |
Airbnb cash on cash: 0.61%
|
6225 RIVER FRUIT COURTWindermere, FLStep into the pinnacle of comfort and ease in the prestigious gated community of Eden Isle... |
4 beds | 3 baths | 2,770 sq.ft. |
$650,000 |
Airbnb cash on cash: 0.6%
|
9247 LEGADO DRIVEWindermere, FLThis exquisite home in Windermere offers the perfect blend of comfort and convenience. Sit... |
4 beds | 3 baths | 2,767 sq.ft. |
$950,000 |
Airbnb cash on cash: -0.18%
|
13106 ORANGE ISLE DRIVEWindermere, FLExplore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a cor... |
5 beds | 5 baths | 3,312 sq.ft. |
$905,000 |
Airbnb cash on cash: N/A
|
1815 WINDERMERE ROADWindermere, FLPre-Construction. To be built. Welcome to 1815 Windermere Road! This remarkable design by ... |
4 beds | 5 baths | 4,290 sq.ft. |
$2,499,000 |
Airbnb cash on cash: -0.27%
|
635 BUTLER STREETWindermere, FLWelcome to your dream home nestled in the heart of Downtown Windermere, just steps away fr... |
3 beds | 3 baths | 2,353 sq.ft. |
$1,180,000 |
Airbnb cash on cash: -0.2%
|
8659 DANFORTH DRIVEWindermere, FLThis 2 Bedroom, 2 1/2 Bath townhome features low hoa fees and an excellent location near t... |
2 beds | 3 baths | 1,380 sq.ft. |
$380,000 |
Airbnb cash on cash: 2.03%
|
11526 VIA LUCERNA CIRCLEWindermere, FLDiscover the epitome of luxury living in this exquisite 5-bedroom, 4.5-bathroom home situa... |
5 beds | 5 baths | 3,084 sq.ft. |
$699,900 |
Airbnb cash on cash: N/A
|
8168 BOAT HOOK LOOP #703Windermere, FLOne or more photo(s) has been virtually staged. Well maintained FIRST FLOOR - CORNER UNIT ... |
3 beds | 2 baths | 1,442 sq.ft. |
$349,000 |
Airbnb cash on cash: 2.32%
|
5379 ISLEWORTH COUNTRY CLUB DRIVEWindermere, FLWelcome to luxury living at its finest! Nestled within the exclusive and world-renowned Is... |
4 beds | 4 baths | 3,872 sq.ft. |
$2,997,000 |
Airbnb cash on cash: -1.58%
|
8335 LAKE BURDEN CIRCLEWindermere, FLWelcome to this fabulous meticulously maintained custom home located in the 24-hour guard... |
4 beds | 3 baths | 2,410 sq.ft. |
$1,100,000 |
Airbnb cash on cash: -0.41%
|
8582 POWDER RIDGE TRAILWindermere, FLMOTIVATED SELLER! IRRESISTIBLE INVESTMENT OPPORTUNITY AWAITS YOU! This impressive Kipling ... |
4 beds | 4 baths | 2,297 sq.ft. |
$680,000 |
Airbnb cash on cash: 0.61%
|
11531 CHARNOCK DRIVEWindermere, FLA must-see magnificent home! The highly sought Emerson Model with 4 bedrooms and 2.5 bathr... |
4 beds | 3 baths | 2,214 sq.ft. |
$684,900 |
Airbnb cash on cash: 0.7%
|
12514 SUMMERPORT BEACH LANEWindermere, FLALMOST AN ACRE! LOCATED ON LAKE BUTLER, THE CHAIN OF LAKES! Very beautiful property and am... |
3 beds | 2 baths | 2,168 sq.ft. |
$2,500,000 |
Airbnb cash on cash: -1.26%
|
3443 WILD MYRTLE COURTWindermere, FLNewly renovated executive home on 1.2 acre homesite in Old Windermere. This charming 5 bed... |
5 beds | 3 baths | 2,918 sq.ft. |
$1,250,000 |
Airbnb cash on cash: N/A
|
6462 DEACON CIRCLEWindermere, FLThis exquisite lakefront estate has been fully updated creating a stylish, modern haven al... |
5 beds | 6 baths | 7,178 sq.ft. |
$6,950,000 |
Airbnb cash on cash: N/A
|
6449 CARTMEL LANEWindermere, FLWelcome to this fully renovated home in the guard-gated community of Windermereâs Reserv... |
4 beds | 4 baths | 3,452 sq.ft. |
$1,850,000 |
Airbnb cash on cash: -0.93%
|
8256 MARITIME FLAG STREET #1702Windermere, FLWelcome to your new haven at 8256 Maritime, nestled in the sought after Windermere zip cod... |
2 beds | 2 baths | 1,161 sq.ft. |
$318,000 |
Airbnb cash on cash: 2.78%
|
5190 LATROBE DRIVEWindermere, FLLocated within the gates of the Isleworth Golf and Country Club community, this luxurious ... |
5 beds | 8 baths | 7,191 sq.ft. |
$6,300,000 |
Airbnb cash on cash: N/A
|
526 BUTLER STREETWindermere, FLRare, coveted, and simply extraordinary. Majestic in every way, this Butler Chain of Lakes... |
4 beds | 6 baths | 6,688 sq.ft. |
$5,755,000 |
Airbnb cash on cash: -1.1%
|
6526 SAWYER SHORES LNWindermere, FLEmbark on a serene Floridian lifestyle in this captivating 4-bedroom, 2-bathroom canal-fro... |
4 beds | 2 baths | 1,842 sq.ft. |
$930,000 |
Airbnb cash on cash: 0.33%
|
9548 HEMPEL COVE BOULEVARDWindermere, FLWelcome to 9548 Hempel Cove Blvd, a luxury highly sought after haven in the heart of Winde... |
4 beds | 4 baths | 4,770 sq.ft. |
$1,649,999 |
Airbnb cash on cash: -0.45%
|
13607 ZORI LANEWindermere, FL**Welcome to Providence in Windermere!** An exceptional opportunity awaits in the esta... |
4 beds | 2 baths | 2,516 sq.ft. |
$725,000 |
Airbnb cash on cash: 0.86%
|
9514 LAVILL COURTWindermere, FLPresenting 9514 Lavill Ct. in the exclusive enclave of Lake Down Village, Windermereâa m... |
5 beds | 4 baths | 4,869 sq.ft. |
$3,999,000 |
Airbnb cash on cash: N/A
|
1106 OAKDALE STREETWindermere, FLNOTE: THIS HOME WILL HAVE A NEW ROOF WITH A 25 YEAR TRANSFERABLE WARRANTY BY THE LAST WEEK... |
3 beds | 2 baths | 1,965 sq.ft. |
$820,000 |
Airbnb cash on cash: 0.46%
|
2009 WATER KEY DRIVEWindermere, FLStunning lake front Windermere home located in the guard gated community of Waterford Poin... |
4 beds | 3 baths | 3,395 sq.ft. |
$1,595,000 |
Airbnb cash on cash: -0.88%
|
104 E 1ST AVENUEWindermere, FLWelcome to an exceptional opportunity to own a stunning home nestled in the Town of Winder... |
4 beds | 3 baths | 2,441 sq.ft. |
$1,475,000 |
Airbnb cash on cash: -0.24%
|
6533 CARTMEL LANEWindermere, FLWelcome to this Fabulous Executive Mediterranean styled Sanctuary, with its beautiful deep... |
4 beds | 4 baths | 4,257 sq.ft. |
$1,750,000 |
Airbnb cash on cash: -1.4%
|
11012 ULLSWATER LANEWindermere, FLStunning Mediterranean masterpiece located in the 24-hour guard gated community of Reserve... |
5 beds | 8 baths | 6,909 sq.ft. |
$2,849,000 |
Airbnb cash on cash: N/A
|
9025 BALMORAL MEWS SQUAREWindermere, FL*The furnishings are SOLD SEPARATELY and are NOT included in the listing price ASK REALTOR... |
5 beds | 5 baths | 4,463 sq.ft. |
$2,399,999 |
Airbnb cash on cash: N/A
|
12540 PARK AVENUEWindermere, FLExperience the epitome of sophistication at this exquisite Park Avenue estate, cradled in ... |
5 beds | 7 baths | 7,736 sq.ft. |
$5,750,000 |
Airbnb cash on cash: N/A
|
12102 MONTALCINO CIRCLEWindermere, FLWelcome to your dream home nestled in a quiet, gated Windermere neighborhood. This stunnin... |
4 beds | 5 baths | 4,296 sq.ft. |
$2,850,000 |
Airbnb cash on cash: -1.4%
|
1608 LAKE RHEA DRIVEWindermere, FLWelcome to a haven of sophistication and exclusivity! Nestled in the highly sought-after c... |
4 beds | 4 baths | 3,747 sq.ft. |
$1,399,999 |
Airbnb cash on cash: -0.53%
|
5186 VARDON DRIVEWindermere, FLNestled along the front nine of Isleworthâs renowned championship golf course overlookin... |
4 beds | 5 baths | 4,739 sq.ft. |
$2,695,000 |
Airbnb cash on cash: -2.04%
|
10821 BAYSHORE DRIVEWindermere, FLUnder Construction. RARE new construction on the Butler Chain of Lakes. Ready for move-in ... |
4 beds | 6 baths | 5,275 sq.ft. |
$5,950,000 |
Airbnb cash on cash: -1.15%
|
12507 OVERSTREET ROADWindermere, FLWelcome to your dream home nestled in the picturesque Lakes of Windermere community! This ... |
4 beds | 4 baths | 4,013 sq.ft. |
$819,500 |
Airbnb cash on cash: 0.36%
|
13832 SUMMERPORT TRAIL LOOPWindermere, FL4/3.5 Home in the area of Windermere. Beautiful spacious house, The house has a rear entra... |
4 beds | 4 baths | 2,150 sq.ft. |
$560,000 |
Airbnb cash on cash: 1.28%
|
13254 PENSHURST LANEWindermere, FL"Welcome to this stunning and expansive residence with CONSERVATION VIEWS and nestled in t... |
5 beds | 4 baths | 3,720 sq.ft. |
$799,000 |
Airbnb cash on cash: N/A
|
12048 SANDY SHORES DRIVEWindermere, FLWelcome to your WATERFRONT oasis on Lake Butler, one of Central Florida's most coveted CHA... |
3 beds | 3 baths | 2,100 sq.ft. |
$2,650,000 |
Airbnb cash on cash: -0.42%
|
5507 WORSHAM COURTWindermere, FLPresenting one of Isleworthâs most iconic mansions: magnificent and grand, impressively ... |
5 beds | 11 baths | 10,200 sq.ft. |
$8,650,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Windermere, FL
There are 94 properties for sale in the city of Windermere . The median list price in Windermere is $930,000 and the average price per square foot is $268. In April 2024, the average monthly cash on cash return in Windermere is 2.00%. The average monthly rental income in Windermere is $3,623.