Real Estate Investment Properties for Sale in Summerland Key, FL
Looking for investment property in Summerland Key, FL with high ROI ?
Explore a variety of short-term homes & houses in Summerland Key, FL. Invest wisely with VRBO & Summerland 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 Summerland Key, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
701 Spanish Main Drive #UNIT 154Summerland Key, FLTransient 1 Day Rentals Allowed! Welcome to your tropical paradise! This charming 2 bedroo... |
2 beds | 2 baths | 836 sq.ft. |
$549,900 |
Airbnb cash on cash: 5.45%
|
56 W Shore DrSummerland Key, FL*Short Sale* Home is located in beautiful Summerland Key just 25 minutes from Key West. Pr... |
3 beds | 2 baths | 1,380 sq.ft. |
$500,000 |
Airbnb cash on cash: 6.14%
|
22841 Buccaneer LaneSummerland Key, FLWelcome to ''Cayo Casa Cudjoe,'' a tropical haven where the island lifestyle seamlessly bl... |
3 beds | 3 baths | 1,920 sq.ft. |
$1,079,000 |
Airbnb cash on cash: 1.78%
|
22961 John Avery LaneSummerland Key, FLBoater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring yo... |
3 beds | 3 baths | 960 sq.ft. |
$989,999 |
Airbnb cash on cash: 2.4%
|
22815 Port Royal LaneSummerland Key, FLDIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND with room for 3 Boats o... |
4 beds | 5 baths | 3,228 sq.ft. |
$3,750,000 |
Airbnb cash on cash: 1.75%
|
24931 Overseas HighwaySummerland Key, FLSeize this rare opportunity to own a prime working waterfront property with exceptional Hi... |
1 beds | 4 baths | 1,965 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 1.05%
|
22865 Redfish LaneSummerland Key, FLThe 'Island Life' awaits you in this stunning well thought out custom designed canal front... |
3 beds | 2 baths | 1,667 sq.ft. |
$1,699,000 |
Airbnb cash on cash: 1.18%
|
4500 Filer Cove RoadSummerland Key, FLPicture perfect Sunset Views over the open water at this 12-Acre waterfront compound locat... |
4 beds | 4 baths | 4,315 sq.ft. |
$5,999,000 |
Airbnb cash on cash: 0.98%
|
76 W Shore DriveSummerland Key, FLDiscover the ultimate boaters retreat in beautiful Summerland Key! This stilted canal-fron... |
3 beds | 2 baths | 1,028 sq.ft. |
$979,000 |
Airbnb cash on cash: 2.57%
|
164 Tortuga LaneSummerland Key, FLWelcome to 164 Tortuga Lane, a solid concrete stilted home perfectly positioned on a wide ... |
3 beds | 2 baths | 1,400 sq.ft. |
$1,199,000 |
Airbnb cash on cash: 1.81%
|
22970 Gasparilla LaneSummerland Key, FLOPEN WATER VIEWS - CANAL WATERFRONT - CUSTOM HOME - DOUBLE LOT on Cudjoe Key. This 3 bedr... |
3 beds | 2 baths | 2,050 sq.ft. |
$2,199,000 |
Airbnb cash on cash: 0.77%
|
701 Spanish Main Drive #UNIT 30Summerland Key, FLWelcome to a stunning brand-new construction in the sought-after Venture Out community on ... |
2 beds | 2 baths | 840 sq.ft. |
$649,999 |
Airbnb cash on cash: 4.73%
|
701 Spanish Main Drive #UNIT 444Summerland Key, FLAffordable piece of paradise! Move in ready, open concept, bright and airy, and freshly pa... |
2 beds | 2 baths | 861 sq.ft. |
$625,000 |
Airbnb cash on cash: 5.29%
|
1151 Ocean DriveSummerland Key, FLTrophy Oceanfront Estate in THE PRIME location on Ocean Dr Summerland Key - surrounded by ... |
5 beds | 6 baths | 3,952 sq.ft. |
$7,495,000 |
Airbnb cash on cash: 0.32%
|
481 E Shore DriveSummerland Key, FLExceptional Investment Opportunity in the Lower Florida Keys! Owner and private financing ... |
3 beds | 3 baths | 2,088 sq.ft. |
$5,500,000 |
Airbnb cash on cash: -0.58%
|
22837 CALICO JACK CircleSummerland Key, FLSELLER SAYS BRING OFFERS! Open Water Views & Sunset Skies with great boating access descri... |
2 beds | 2 baths | 1,008 sq.ft. |
$1,135,000 |
Airbnb cash on cash: 2.19%
|
951 LAGOON DriveSummerland Key, FLNeed space for family and friends? Come see this 4 bedroom Summerland Cove Isles beautiful... |
4 beds | 3 baths | 1,704 sq.ft. |
$1,599,900 |
Airbnb cash on cash: 6.78%
|
701 Spanish Main Drive #UNIT 49Summerland Key, FLNightly Licensed Transient Rental!!!This amazing, two bedroom / one bathroom, open water f... |
2 beds | 1 baths | 806 sq.ft. |
$925,000 |
Airbnb cash on cash: 2.58%
|
701 Spanish Main 369, 370 Drive #UNIT 369Summerland Key, FLBoater's Paradise with Expansive Waterfront Views!Rare opportunity to own one of only thre... |
2 beds | 2 baths | 840 sq.ft. |
$999,965 |
Airbnb cash on cash: 2.02%
|
701 Spanish Main Drive #UNIT 635Summerland Key, FLTransient Rental License! Welcome to the epitome of comfort and convenience in this Palm H... |
2 beds | 2 baths | 864 sq.ft. |
$439,000 |
Airbnb cash on cash: 7.28%
|
701 Spanish Main Drive #UNIT 234Summerland Key, FLTransient Rental License. Beautiful updated 2bed/2bath, fully furnished, canal front home ... |
2 beds | 2 baths | 604 sq.ft. |
$499,000 |
Airbnb cash on cash: 6.3%
|
701 Spanish Main Drive #UNIT 29Summerland Key, FLWelcome to a stunning brand-new construction in the sought-after Venture Out community on ... |
2 beds | 2 baths | 840 sq.ft. |
$659,999 |
Airbnb cash on cash: 4.65%
|
701 Spanish Main Drive #UNIT 51Summerland Key, FLPanoramic Ocean Views With Transient Rental License! This beautifully updated and well-mai... |
2 beds | 2 baths | 888 sq.ft. |
$985,000 |
Airbnb cash on cash: 2.42%
|
715 E Caribbean Dr ESummerland Key, FLTake advantage of a rare lease-to-own opportunity! Experience the ultimate boaterâs lif... |
3 beds | 2 baths | 1,544 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 1.95%
|
142 Peg Leg LnSummerland Key, FLWelcome to your dream coastal retreat! This newer 4-bedroom, 3-bath luxury home offers the... |
4 beds | 3 baths | 2,136 sq.ft. |
$1,599,999 |
Airbnb cash on cash: 6.74%
|
22846 Port Royal LaneSummerland Key, FLStunning open-water views, unforgettable sunsets over the bay, and direct ocean access fro... |
2 beds | 2 baths | 1,086 sq.ft. |
$998,000 |
Airbnb cash on cash: 3.05%
|
21855 21865 Spain BoulevardSummerland Key, FLMajestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neig... |
3 beds | 2 baths | 1,467 sq.ft. |
$1,750,000 |
Airbnb cash on cash: 1.09%
|
22967 Redfish LaneSummerland Key, FLCustom Luxury Meets Waterfront Living on Cudjoe Key. Welcome to 22967 Redfish Lane -- a o... |
3 beds | 4 baths | 3,747 sq.ft. |
$2,999,000 |
Airbnb cash on cash: -0.16%
|
558 E Shore DriveSummerland Key, FLSingle-family property on a dry lot in Summerland Key. This property features 3 bedrooms ... |
2 beds | 2 baths | 1,392 sq.ft. |
$735,000 |
Airbnb cash on cash: 4.56%
|
22954 Buccaneer LaneSummerland Key, FLWelcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly ... |
3 beds | 2 baths | 1,400 sq.ft. |
$999,000 |
Airbnb cash on cash: 2.72%
|
0 MelodySummerland Key, FLAn unparalleled opportunity to own your own private island in the Florida Keys. Melody Key... |
3 beds | 4 baths | 2,851 sq.ft. |
$7,000,000 |
Airbnb cash on cash: -0.69%
|
Real Estate investment in Summerland-key, FL
There are 31 properties for sale in the city of Summerland Key . The median list price in Summerland Key is $999,965 and the average price per square foot is $605. In September 2025, the average monthly cash on cash return in Summerland Key is 1.00%. The average monthly rental income in Summerland Key is $2,489.