Real Estate Investment Properties for Sale in Longboat Key, FL
Looking for investment property in Longboat Key, FL with high ROI ?
Explore a variety of short-term homes & houses in Longboat Key, FL. Invest wisely with VRBO & Longboat Key, 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 Longboat Key, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
1945 Gulf OF Mexico Dr #M2-402LONGBOAT KEY, FLSeaplace Condominiums, half mile Gulf of Mexico beachfront property with chaise lounges & ... |
2 beds | 2 baths | 933 sq.ft. |
$490,000 |
Airbnb cash on cash: -1.48%
|
707 Saint Judes Dr S #1LONGBOAT KEY, FLHave you ever dreamed of living on the water on Longboat Key, with your boat just steps fr... |
1 beds | 1 baths | 630 sq.ft. |
$399,000 |
Airbnb cash on cash: 5.63%
|
1914 Harbour Links Cir #10LONGBOAT KEY, FLTucked behind the gates of Bay Isles in the Emerald Pointe community, this 3BR/3.5BA resid... |
3 beds | 3 baths | 2,180 sq.ft. |
$1,445,000 |
Airbnb cash on cash: -0.8%
|
705 Jungle Queen WayLONGBOAT KEY, FLTucked away on the coveted north end of Longboat Key, this custom-designed coastal contemp... |
4 beds | 3 baths | 3,083 sq.ft. |
$2,795,000 |
Airbnb cash on cash: -0.61%
|
6700 Gulf OF Mexico Dr #143LONGBOAT KEY, FLWelcome to your coastal retreat on beautiful Longboat Key! This charming second-story cond... |
1 beds | 1 baths | 936 sq.ft. |
$410,000 |
Airbnb cash on cash: 2.66%
|
1932 Harbourside Dr #244LONGBOAT KEY, FLWelcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in... |
2 beds | 2 baths | 1,192 sq.ft. |
$1,175,000 |
Airbnb cash on cash: -2.2%
|
729 Saint Judes Dr S #2LONGBOAT KEY, FLBeautifully renovated waterfront unit at 729 St. Jude's Way with gorgeous water views and ... |
2 beds | 2 baths | 840 sq.ft. |
$525,000 |
Airbnb cash on cash: 2.06%
|
565 Sanctuary Dr #B106LONGBOAT KEY, FLNestled behind the exclusive gates of the Longboat Key Club, The Sanctuary enjoys an envia... |
3 beds | 3 baths | 2,375 sq.ft. |
$1,699,000 |
Airbnb cash on cash: -2.68%
|
1095 Gulf OF Mexico Dr #303LONGBOAT KEY, FLExperience everything coastal luxury living has to offer in one of Longboat Key's most sou... |
2 beds | 2 baths | 1,503 sq.ft. |
$775,000 |
Airbnb cash on cash: -1.88%
|
5841 GULF OF MEXICO Drive #244LONGBOAT KEY, FLREDUCE PRICE- RARE FIND!!! This fully furnished turnkey 1bedroom/1bath end unit has an ope... |
1 beds | 1 baths | 520 sq.ft. |
$505,000 |
Airbnb cash on cash: 1.57%
|
4340 Falmouth Dr #104LONGBOAT KEY, FLWelcome to your slice of paradise on beautiful Longboat Key. Priced to sell and offered fu... |
2 beds | 2 baths | 1,072 sq.ft. |
$474,999 |
Airbnb cash on cash: -0.74%
|
3530 Mistletoe LnLONGBOAT KEY, FLFreshly updated and directly overlooking Sarasota Bay, this four-bedroom waterfront reside... |
4 beds | 3 baths | 3,102 sq.ft. |
$2,675,000 |
Airbnb cash on cash: -0.43%
|
1935 Gulf OF Mexico Dr #G7-304LONGBOAT KEY, FLExperience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom... |
2 beds | 1 baths | 933 sq.ft. |
$449,000 |
Airbnb cash on cash: -2.23%
|
1906 Harbourside Dr #303LONGBOAT KEY, FLLocated on a boating canal in Fairway Bay, this property offers the rare convenience of wa... |
2 beds | 2 baths | 1,590 sq.ft. |
$799,000 |
Airbnb cash on cash: -0.32%
|
1050 Longboat Club Rd #903LONGBOAT KEY, FLSet on the 9th floor at Privateer North, behind the gates of the Longboat Key Club, this b... |
2 beds | 2 baths | 1,409 sq.ft. |
$995,000 |
Airbnb cash on cash: -2.63%
|
718 SPANISH Drive NLONGBOAT KEY, FLDiscover Longboat Key waterfront living at its very best at 718 Spanish Dr N, a beautifull... |
2 beds | 2 baths | 1,327 sq.ft. |
$435,000 |
Airbnb cash on cash: -0.92%
|
1926 Harbourside Dr #1302LONGBOAT KEY, FLGATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main... |
2 beds | 2 baths | 2,606 sq.ft. |
$769,000 |
Airbnb cash on cash: -2.44%
|
250 SANDS POINT Road #5101LONGBOAT KEY, FLA corner A+ junior suite with a walk-down rarely becomes available. It offers quiet and pr... |
1 beds | 1 baths | 716 sq.ft. |
$995,000 |
Airbnb cash on cash: 0.12%
|
3806 Gulf OF Mexico Dr #C208LONGBOAT KEY, FLDiscover coastal living at its finest with this charming condominium located on Gulf of Me... |
1 beds | 1 baths | 712 sq.ft. |
$295,000 |
Airbnb cash on cash: 4.89%
|
610 Hibiscus WayLONGBOAT KEY, FLPre-Construction. To be built. Welcome to a luxurious modern retreat in The Preserve on Lo... |
4 beds | 4 baths | 2,788 sq.ft. |
$2,650,000 |
Airbnb cash on cash: 0.61%
|
5320 Gulf OF Mexico Dr #204LONGBOAT KEY, FLWhat if you didn't have to choose between boating and the beach? At Longboat Landing, Sara... |
3 beds | 2 baths | 1,323 sq.ft. |
$875,000 |
Airbnb cash on cash: -0.61%
|
4621 GULF OF MEXICO Drive #10DLONGBOAT KEY, FLHuge Price Adjustment! PRICED TO SELL!!! Check out these consistently strong revenue numbe... |
2 beds | 2 baths | 756 sq.ft. |
$625,000 |
Airbnb cash on cash: -0.21%
|
1211 Gulf OF Mexico Dr #403LONGBOAT KEY, FLEscape to elegance in this tastefully renovated, fully furnished fourth-floor residence at... |
2 beds | 2 baths | 1,585 sq.ft. |
$1,695,000 |
Airbnb cash on cash: -2.1%
|
775 Longboat Club Rd #401LONGBOAT KEY, FLDiscover Coastal Elegance at The Beaches of Longboat Key! Nestled behind the renowned gate... |
2 beds | 2 baths | 1,510 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -2.98%
|
535 Sanctuary Dr #C807LONGBOAT KEY, FLSanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Saras... |
3 beds | 3 baths | 2,580 sq.ft. |
$3,750,000 |
Airbnb cash on cash: -2.01%
|
617 WESTON POINTE CourtLONGBOAT KEY, FLWelcome to **617 Weston Pointe Court**, where timeless elegance meets the Florida waterfro... |
4 beds | 5 baths | 4,395 sq.ft. |
$3,100,000 |
Airbnb cash on cash: -0.7%
|
100 Sands Point Rd #303LONGBOAT KEY, FLDon't miss this rare opportunity to call Sands Point home - an iconic beachfront community... |
3 beds | 2 baths | 1,941 sq.ft. |
$915,000 |
Airbnb cash on cash: -1.45%
|
3606 Fair Oaks PlLONGBOAT KEY, FLNestled behind the gates of the highly celebrated Bay Isles community, this exceptional fi... |
5 beds | 3 baths | 3,842 sq.ft. |
$4,999,000 |
Airbnb cash on cash: 1.71%
|
1485 Gulf OF Mexico Dr #303LONGBOAT KEY, FLCoastal elegance meets effortless island living at The Player's Club on Longboat Key. This... |
2 beds | 2 baths | 1,569 sq.ft. |
$1,395,000 |
Airbnb cash on cash: -2.32%
|
2410 HARBOURSIDE Drive #142LONGBOAT KEY, FLPositioned on the fourth floor of Marina Bay Building I, this completely renovated bayfron... |
3 beds | 4 baths | 3,382 sq.ft. |
$2,595,000 |
Airbnb cash on cash: -2.31%
|
6489 Gulfside RdLONGBOAT KEY, FLThis Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. E... |
4 beds | 4 baths | 6,616 sq.ft. |
$13,995,000 |
Airbnb cash on cash: -0.95%
|
1930 Harbourside Dr #122LONGBOAT KEY, FLWelcome to your waterfront retreat in the highly sought-after Fairway Bay community, where... |
2 beds | 2 baths | 1,192 sq.ft. |
$499,000 |
Airbnb cash on cash: -3.3%
|
3240 Gulf OF Mexico Dr #B504LONGBOAT KEY, FLWelcome to Portobello, a Gulf to Bay community on mid Longboat Key where residents enjoy t... |
2 beds | 2 baths | 1,260 sq.ft. |
$689,000 |
Airbnb cash on cash: 0.57%
|
597 BUTTONWOOD DriveLONGBOAT KEY, FLCompleted New Construction - Best-Priced Luxury New Construction on Longboat Key! Gulf & B... |
5 beds | 7 baths | 4,176 sq.ft. |
$4,000,000 |
Airbnb cash on cash: 3.29%
|
1600 Harbor Sound DrLONGBOAT KEY, FLPre-Construction. To be built. Positioned directly across from the iconic St. Regis Longbo... |
5 beds | 5 baths | 5,689 sq.ft. |
$11,900,000 |
Airbnb cash on cash: 0.21%
|
Real Estate investment in Longboat-key, FL
There are 253 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,049,306 and the average price per square foot is $559. In October 2026, the average monthly cash on cash return in Longboat Key is 1.00%. The average monthly rental income in Longboat Key is $2,290.