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 |
|---|---|---|---|
5141 AUTUMN RIDGE LANEWindermere, FLUnder contract-accepting backup offers. Welcome home to this beautifully renovated one-sto... |
4 beds | 3 baths | 2,390 sq.ft. |
$949,000 |
Airbnb cash on cash: 0.96%
|
12654 CRAGSIDE LANEWindermere, FLWelcome to a truly rare opportunity in Windermereâwhere TOP-RATED SCHOOLS, access to the... |
5 beds | 4 baths | 3,072 sq.ft. |
$699,900 |
Airbnb cash on cash: 4.52%
|
11325 FENIMORE COURTWindermere, FLCome home to a golf enthusiastâs dream set along the 6th Hole of the renowned Jack Nickl... |
4 beds | 4 baths | 2,658 sq.ft. |
$1,300,000 |
Airbnb cash on cash: -0.19%
|
7462 BENTONSHIRE AVEWindermere, FLBIG price reduction for this move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC... |
3 beds | 3 baths | 1,480 sq.ft. |
$369,800 |
Airbnb cash on cash: 2.43%
|
13808 ANCILLA BOULEVARDWindermere, FLOne or more photo(s) has been virtually staged. One or more photo(s) has been virtually st... |
3 beds | 3 baths | 1,461 sq.ft. |
$414,999 |
Airbnb cash on cash: 2.45%
|
8752 LOOKOUT POINTE DRIVEWindermere, FLExperience the enchantment of a luxurious lifestyle with a home that offers elegance, comf... |
4 beds | 4 baths | 3,270 sq.ft. |
$899,000 |
Airbnb cash on cash: 0.72%
|
9485 WOODBREEZE BOULEVARDWindermere, FLLocated in the highly sought-after Silver Woods community in Windermere, this beautifully ... |
3 beds | 2 baths | 1,723 sq.ft. |
$564,900 |
Airbnb cash on cash: 1.25%
|
8582 POWDER RIDGE TRAILWindermere, FLAN IRRESISTIBLE INVESTMENT OPPORTUNITY â OR YOUR FIRST HOME! Welcome to this stunning K... |
4 beds | 4 baths | 2,297 sq.ft. |
$680,000 |
Airbnb cash on cash: 1.57%
|
7545 LAKE ALBERT DRIVEWindermere, FLWelcome to 7545 Lake Albert Drive. Where timeless architecture meets modern luxury. Nestl... |
4 beds | 5 baths | 3,425 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 0.59%
|
6864 HELMSLEY CIRCLEWindermere, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. **... |
3 beds | 2 baths | 1,609 sq.ft. |
$485,000 |
Airbnb cash on cash: 1.95%
|
6734 BRIDGEWATER VILLAGE ROADWindermere, FLWelcome to 6734 Bridgewater Village Road, a true gem nestled in the highly sought-after Vi... |
3 beds | 3 baths | 3,094 sq.ft. |
$699,000 |
Airbnb cash on cash: 0.24%
|
11660 DELWICK DRIVEWindermere, FLGolden season, golden opportunity in The Reserve at Belmere. Seller contribution to the bu... |
4 beds | 5 baths | 3,051 sq.ft. |
$850,000 |
Airbnb cash on cash: 0.46%
|
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: -2.04%
|
7673 RIPPLEPOINTE WAYWindermere, FLWelcome to Lake Burden, one of Windermereâs most desirable and well-established communit... |
4 beds | 3 baths | 2,212 sq.ft. |
$469,500 |
Airbnb cash on cash: 2.56%
|
13225 CHARFIELD STREETWindermere, FLWelcome Home to your Spacious ENCLOSED and Private POOL HOME located in the sought-after c... |
4 beds | 4 baths | 2,628 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.03%
|
9648 MCCORMICK PLACEWindermere, FLStunning golf and lake views and beautifully updated grounds are hallmarks of this elegant... |
3 beds | 4 baths | 4,751 sq.ft. |
$3,800,000 |
Airbnb cash on cash: -1.68%
|
14466 BRIDGEWATER CROSSINGS BOULEVARDWindermere, FLUnder contract-accepting backup offers. **Video Tour Available** Welcome to Summerport whe... |
4 beds | 3 baths | 1,642 sq.ft. |
$410,000 |
Airbnb cash on cash: 3.97%
|
7628 Billingham StreetWindermere, FLDiscover this beautiful townhome located in the sought-after community of Wickman Park of ... |
3 beds | 3 baths | 1,480 sq.ft. |
$410,000 |
Airbnb cash on cash: 3.17%
|
2844 MARQUESAS COURTWindermere, FLWelcome to your private sanctuary, where every sunrise and sunset dances over the shimmeri... |
4 beds | 3 baths | 5,365 sq.ft. |
$3,900,000 |
Airbnb cash on cash: -0.82%
|
13120 ZORI LANEWindermere, FLImagine waking up every morning to the serene beauty of your lakefront retreat, with Littl... |
4 beds | 5 baths | 4,329 sq.ft. |
$1,750,000 |
Airbnb cash on cash: -0.51%
|
11922 ANGLE POND AVENUEWindermere, FLOne or more photo(s) has been virtually staged. Located just 2 minutes from Disney in the ... |
4 beds | 4 baths | 3,382 sq.ft. |
$775,000 |
Airbnb cash on cash: 1.26%
|
9631 HOLLYGLEN PLACEWindermere, FLNestled in the sought-after community of Windermere Downs, this California-contemporary ho... |
4 beds | 3 baths | 2,854 sq.ft. |
$765,000 |
Airbnb cash on cash: 0.92%
|
2128 LAKE CRESCENT COURTWindermere, FLShort Sale. Come see it today! Finally Bank above price to close. This property sounds li... |
5 beds | 3 baths | 2,987 sq.ft. |
$856,000 |
Airbnb cash on cash: 3.29%
|
2540 HEMPEL COVE CTWindermere, FLStunning Renovation on 1 Acre in Lake Down Cove. Located at the end of a quiet cul-de-sac,... |
5 beds | 3 baths | 3,356 sq.ft. |
$1,275,000 |
Airbnb cash on cash: 1.47%
|
11849 CAVE RUN AVENUEWindermere, FLImmaculate and light-filled 4-bedroom, 3.5-bath home with a huge bonus room and flex space... |
4 beds | 4 baths | 3,414 sq.ft. |
$799,000 |
Airbnb cash on cash: 1.01%
|
3426 COCARD COURTWindermere, FLAn exceptional estate, masterfully renovated and transformed into a reimagined showplace: ... |
4 beds | 5 baths | 7,222 sq.ft. |
$3,450,000 |
Airbnb cash on cash: -1.1%
|
635 BUTLER STREETWindermere, FLUnder contract-accepting backup offers. Prime Downtown Windermere Corner Lot with Lake Vie... |
3 beds | 3 baths | 2,353 sq.ft. |
$995,000 |
Airbnb cash on cash: -0.19%
|
11520 VIA LUCERNA CIRCLEWindermere, FLBeautifully Freshly painted Home in Windermereâs Belmere Village Welcome to this ligh... |
4 beds | 2 baths | 2,505 sq.ft. |
$630,000 |
Airbnb cash on cash: 1.47%
|
12001 LAKE BUTLER BOULEVARDWindermere, FLExceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend ... |
3 beds | 3 baths | 3,135 sq.ft. |
$1,775,000 |
Airbnb cash on cash: -0.66%
|
4071 ISABELLA CIRCLEWindermere, FLWelcome to Casabella at Windermere, a beautiful gated community where luxury and elegance ... |
5 beds | 8 baths | 6,753 sq.ft. |
$3,200,000 |
Airbnb cash on cash: -0.69%
|
13413 HOPKINTON COURTWindermere, FLNewly Renovated Home near Disney!Stunning cul-de-sac Windermere residence, just minutes aw... |
4 beds | 4 baths | 2,642 sq.ft. |
$789,000 |
Airbnb cash on cash: 1.07%
|
3443 WILD MYRTLE COURTWindermere, FLWelcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a ser... |
5 beds | 3 baths | 2,918 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 2.99%
|
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: 3.02%
|
12540 PARK AVENUEWindermere, FLOffering a prime lakefront location along the shores of Lake Butler in the esteemed gated ... |
5 beds | 6 baths | 7,183 sq.ft. |
$4,650,000 |
Airbnb cash on cash: -1.02%
|
11019 KENTMERE COURTWindermere, FLMeticulously upgraded and thoughtfully designed, this expansive Mediterranean estate rests... |
4 beds | 4 baths | 3,813 sq.ft. |
$1,500,000 |
Airbnb cash on cash: -0.26%
|
1927 WATERMERE LANEWindermere, FLLuxury living in one of Central Florida's most sought-after neighborhoods, Windermere Gran... |
4 beds | 4 baths | 3,053 sq.ft. |
$1,146,000 |
Airbnb cash on cash: 0.04%
|
6443 CARTMEL LANEWindermere, FLExquisitely appointed home being sold fully furnished. Nestled within the highly coveted R... |
5 beds | 5 baths | 4,257 sq.ft. |
$1,475,000 |
Airbnb cash on cash: 0.94%
|
13254 PENSHURST LANEWindermere, FLOne or more photo(s) has been virtually staged. This 5-bedroom, 3.5-bath home in Windermer... |
5 beds | 4 baths | 3,720 sq.ft. |
$769,000 |
Airbnb cash on cash: 4.01%
|
409 W 2ND AVENUEWindermere, FLStep inside this beautifully updated home where clean lines, soaring ceilings, and two-sto... |
5 beds | 5 baths | 4,688 sq.ft. |
$2,425,000 |
Airbnb cash on cash: 0.48%
|
14025 OASIS SPRINGS LANE #901Windermere, FL***3D Tour on Virtual Tour Link 1*** This immaculately kept, gated end unit townhome boast... |
3 beds | 3 baths | 1,786 sq.ft. |
$386,000 |
Airbnb cash on cash: 1.33%
|
Real Estate investment in Windermere, FL
There are 146 properties for sale in the city of Windermere . The median list price in Windermere is $989,990 and the average price per square foot is $291. In October 2025, the average monthly cash on cash return in Windermere is 2.00%. The average monthly rental income in Windermere is $3,412.