Real Estate Investment Properties for Sale in Windermere, FL
Looking for investment property in Windermere, FL with high ROI ?
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 |
|---|---|---|---|
8168 BOAT HOOK Loop #724Windermere, FLVirtually Staged. Imagine coming home to a resort-style community just minutes from Walt D... |
3 beds | 2 baths | 1,455 sq.ft. |
$325,000 |
Airbnb cash on cash: 4.08%
|
6363 SEDONA LEAF CourtWindermere, FLVirtually Staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home tucked... |
4 beds | 3 baths | 2,665 sq.ft. |
$724,900 |
Airbnb cash on cash: -0.02%
|
11035 SCHOONER WayWindermere, FLNestled among the Butler Chain of Lakes in the charming Town of Windermere, this 4-bedroom... |
4 beds | 3 baths | 3,517 sq.ft. |
$1,500,000 |
Airbnb cash on cash: -0.37%
|
11938 SILVERLAKE PARK DriveWindermere, FLMove-In Ready! Beautifully Updated Home in the Highly Desirable Windermere Area! Welcome t... |
4 beds | 3 baths | 2,074 sq.ft. |
$539,900 |
Airbnb cash on cash: 1.2%
|
13228 ROSKIN LaneWindermere, FLVirtually Staged. 13228 Roskin Ln is a two-story Windermere home with a two-story foyer an... |
4 beds | 2 baths | 2,745 sq.ft. |
$645,000 |
Airbnb cash on cash: 0.96%
|
910 LASCALA DriveWindermere, FLPRICE REDUCTION and SIGNIFICANT recent upgrades include the installation of a NEW WATER HE... |
4 beds | 4 baths | 2,742 sq.ft. |
$725,000 |
Airbnb cash on cash: 0.56%
|
7712 FORDSON LaneWindermere, FLThis Berkshire Place townhome offers a thoughtfully arranged two-story layout with three b... |
3 beds | 3 baths | 1,644 sq.ft. |
$350,000 |
Airbnb cash on cash: 3.61%
|
4812 ALEXANDRA GARDEN CourtWindermere, FLLuxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf ... |
3 beds | 5 baths | 4,262 sq.ft. |
$3,699,000 |
Airbnb cash on cash: -2.27%
|
14077 ANCILLA BoulevardWindermere, FLThere is something truly special about coming home to Summerport, and this move-in-ready t... |
3 beds | 3 baths | 1,651 sq.ft. |
$399,000 |
Airbnb cash on cash: 3.67%
|
33 MAIN StreetWindermere, FLBUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress tree... |
4 beds | 2 baths | 2,130 sq.ft. |
$1,572,000 |
Airbnb cash on cash: -0.37%
|
13755 BRAVANTE AlleyWindermere, FL**This house comes with a REDUCED RATE through the seller's preferred lender. This is a le... |
3 beds | 3 baths | 2,091 sq.ft. |
$465,000 |
Airbnb cash on cash: 2.46%
|
12303 LANGSTAFF DriveWindermere, FLABSOLUTELY STUNNING WINDERMERE END-UNIT TOWNHOME! Welcome home to this exceptional end-uni... |
3 beds | 3 baths | 1,545 sq.ft. |
$420,000 |
Airbnb cash on cash: 3.66%
|
212 W 1ST AvenueWindermere, FLVirtually Staged. Positioned along the coveted Butler Chain of Lakes, this waterfront resi... |
4 beds | 2 baths | 2,627 sq.ft. |
$1,650,000 |
Airbnb cash on cash: -0.58%
|
7033 BRAMLEA LaneWindermere, FLModern elegance meets resort-style living in the Lakes of Windermere. Welcome to a beautif... |
3 beds | 3 baths | 2,229 sq.ft. |
$647,000 |
Airbnb cash on cash: 1.71%
|
12718 WINDERMERE ISLES PlaceWindermere, FLSpectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situat... |
5 beds | 4 baths | 3,487 sq.ft. |
$1,439,000 |
Airbnb cash on cash: 9.28%
|
12001 LAKE BUTLER BoulevardWindermere, FLExceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend of ... |
3 beds | 3 baths | 3,135 sq.ft. |
$1,775,000 |
Airbnb cash on cash: -0.28%
|
11734 WATER RUN AlleyWindermere, FLGet ready to move into one of the best homes and areas right now! Located in the thriving,... |
3 beds | 3 baths | 1,727 sq.ft. |
$445,000 |
Airbnb cash on cash: 2.28%
|
7327 MILLSTONE StreetWindermere, FLVirtually Staged. This former model corner unit townhome (3 bed, 2.5 bath) offers maintena... |
3 beds | 3 baths | 1,531 sq.ft. |
$449,000 |
Airbnb cash on cash: 2.96%
|
7011 NOBLETON DriveWindermere, FLUnder contract-accepting backup offers. Don't miss an Opportunity to own this Great Crafts... |
4 beds | 3 baths | 2,460 sq.ft. |
$560,000 |
Airbnb cash on cash: 1.69%
|
12540 PARK AvenueWindermere, FLExtraordinary Lake Butler views abound from this classically elegant yet recently updated ... |
5 beds | 6 baths | 7,740 sq.ft. |
$4,500,000 |
Airbnb cash on cash: 1.39%
|
5379 ISLEWORTH COUNTRY CLUB DriveWindermere, FLA truly incredible opportunity to create a custom estate in the highly coveted Isleworth c... |
4 beds | 4 baths | 3,872 sq.ft. |
$3,400,000 |
Airbnb cash on cash: -1.24%
|
4948 WISE BIRD DriveWindermere, FLOne or more photo(s) has been virtually staged. Don't miss the opportunity to live in the ... |
3 beds | 2 baths | 1,979 sq.ft. |
$679,000 |
Airbnb cash on cash: 1.49%
|
12102 MONTALCINO CircleWindermere, FLVirtually Staged. Welcome to 12102 Montalcino Circle, an exceptional custom built waterfro... |
4 beds | 5 baths | 4,296 sq.ft. |
$3,100,000 |
Airbnb cash on cash: -1.54%
|
12988 BORLAND StreetWindermere, FLWelcome to 12988 Borland Street in sought-after Wickham Park, where comfort, convenience, ... |
3 beds | 3 baths | 1,460 sq.ft. |
$435,000 |
Airbnb cash on cash: 3.39%
|
12264 MONTALCINO CircleWindermere, FLLakefront, Luxurious, home with Private Pool in Windermere. A True Paradise! Discover this... |
4 beds | 7 baths | 7,872 sq.ft. |
$5,390,000 |
Airbnb cash on cash: -2.33%
|
5138 FAIRWAY OAKS DRWindermere, FLSet along Isleworth's signature 12th fairway, this fully reimagined estate captures the es... |
4 beds | 5 baths | 4,330 sq.ft. |
$4,999,500 |
Airbnb cash on cash: -1.29%
|
14442 DESERT HAVEN Street #4305Windermere, FLBeautiful Two-Story Condo in Gated Windermere Community - Minutes from Disney World Welcom... |
3 beds | 3 baths | 1,534 sq.ft. |
$359,900 |
Airbnb cash on cash: 3.54%
|
13161 LAKE BUTLER BoulevardWindermere, FLExtraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! S... |
5 beds | 5 baths | 4,500 sq.ft. |
$3,200,000 |
Airbnb cash on cash: 3.39%
|
11923 LAKE BUTLER BoulevardWindermere, FLNestled on one of Windermere's most desirable streets, this charming home offers a rare op... |
3 beds | 2 baths | 2,238 sq.ft. |
$1,630,000 |
Airbnb cash on cash: -0.12%
|
13226 Zori LaneWindermere, FLWELCOME to this STUNNING, BEAUTIFULLY UPDATED, MOVE-IN READY home in one of Windermere's m... |
4 beds | 2 baths | 2,521 sq.ft. |
$645,000 |
Airbnb cash on cash: 1.18%
|
14371 CREST PALM AvenueWindermere, FLOne or more photo(s) has been virtually staged. Arlington Floorplan - 3153 Sq. Ft. | 4 Bed... |
4 beds | 4 baths | 3,153 sq.ft. |
$1,029,990 |
Airbnb cash on cash: 0.46%
|
8724 Peachtree Park CourtWindermere, FLRecent pricing adjustment creates an exceptional opportunity to own a thoughtfully designe... |
4 beds | 4 baths | 3,315 sq.ft. |
$829,500 |
Airbnb cash on cash: -0.18%
|
12930 VENNETTA WayWindermere, FLWelcome to this beautifully renovated 3-bedroom, 2.5-bathroom townhouse in Berkshire Park,... |
3 beds | 3 baths | 1,644 sq.ft. |
$380,000 |
Airbnb cash on cash: 4.18%
|
Real Estate investment in Windermere, FL
There are 111 properties for sale in the city of Windermere . The median list price in Windermere is $1,049,372 and the average price per square foot is $335. In September 2026, the average monthly cash on cash return in Windermere is 2.00%. The average monthly rental income in Windermere is $3,068.