23941 Henry Street
Summerland Key, FL 33042
MLS# 617402
3 beds | 2 baths | 2232 sqft
Open House (02/07/2026 - 12:00 pm - 2:00 pm)
Property DescriptionOceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.
Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views, exceptional privacy, and the true tropical lifestyle.
The open-concept 2,232 SF interior features large windows, oversized glass doors, and multiple covered porches that fill the home with natural light and maximize water views. The chef's kitchen includes stainless steel appliances, tall custom wood cabinetry and generous counter space--perfect for entertaining.
The home offers 3 bedrooms 2 bathrooms (3rd room is currently used as office), lower level includes a welcoming foyer entry room, large storage/fishing room, and a drive through 2-car CBS garage.
Outdoors, enjoy your own private resort setting with a custom built in ground lagoon-style pool, cascading waterfall, hot tub, lush mature tropical landscaping, fruit trees, butterfly plants and a poolside tiki hut. Relax under the palms on the beach, or entertain on beautifully paved travertine grounds overlooking the ocean.
A boaters paradise, the 62 ft concrete dock provides quick, direct access to both the Ocean and Gulf. Dock features a new 17,000 LB boat lift, 3 additional davits, and provides protective dockage. A private sandy beach with 300 ft of bay bottom.
This rare oceanfront offering blends privacy, tropical ambiance, boating convenience, and stunning sunrise-to-sunset views. Walking & biking-Florida Keys Heritage Trail just foot steps away. A private airstrip on the island, excellent local restaurants, and close proximity to both Key West & Marathon make this home ideal for year-round living or a luxurious island escape.
Seller is a Florida Licensed Real Estate Agent.
Listing Board: Marathon/Lower Keys
Potential Short Sale: No
Bank Owned: No
Current Price: $2,985,000
Listing Date: 2025-11-21
List Price: $2,985,000
City: Summerland
Mile Marker: 24
Marathon Neighborhood: N/A
Side: Ocean
Alternate Key #: 1250856
Parcel #: 00188840-000000
Zoning: IS - Improved Subivision District
Deed Restrictions: Unknown
Legal: Lot 23 and ADJ portion of Mary t and ADJ BTM Dobies Sub Amended Plat PB 2-135
Taxes: 6997
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 23941
Street Name: Henry
Street Suffix: Street
Key/Island: Summerland Key
State/Province: FL
Zip Code: 33042
County: Monroe
Subdivision: Dobie's Sub (24.0)
Area: 08 - Summerland Key
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 3
Lot SqFt: 7188
Pool: Yes
Lot Sqft Source: Property Data Card
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 2002
Living Apx SqFt: 2232
Total Bedrooms: 3
Full Baths: 2
Remarks – Consumer: Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.
Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views, exceptional privacy, and the true tropical lifestyle.
The open-concept 2,232 SF interior features large windows, oversized glass doors, and multiple covered porches that fill the home with natural light and maximize water views. The chef's kitchen includes stainless steel appliances, tall custom wood cabinetry and generous counter space--perfect for entertaining.
The home offers 3 bedrooms 2 bathrooms (3rd room is currently used as office), lower level includes a welcoming foyer entry room, large storage/fishing room, and a drive through 2-car CBS garage.
Outdoors, enjoy your own private resort setting with a custom built in ground lagoon-style pool, cascading waterfall, hot tub, lush mature tropical landscaping, fruit trees, butterfly plants and a poolside tiki hut. Relax under the palms on the beach, or entertain on beautifully paved travertine grounds overlooking the ocean.
A boaters paradise, the 62 ft concrete dock provides quick, direct access to both the Ocean and Gulf. Dock features a new 17,000 LB boat lift, 3 additional davits, and provides protective dockage. A private sandy beach with 300 ft of bay bottom.
This rare oceanfront offering blends privacy, tropical ambiance, boating convenience, and stunning sunrise-to-sunset views. Walking & biking-Florida Keys Heritage Trail just foot steps away. A private airstrip on the island, excellent local restaurants, and close proximity to both Key West & Marathon make this home ideal for year-round living or a luxurious island escape.
Seller is a Florida Licensed Real Estate Agent.
Directions: MM 24 Oceanside.
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dock: Concrete
Boat Lift: 1
Davits: 1
Seawall: Concrete
Stainless Steel Appliance(s): 1
Washer: 1
Ceiling Fans(s): 1
Central Air: 1
Entrance Foyer: 1
Granite Counter Top: 1
Smoke Alarms: 1
Storage: 1
Walk-in Closet(s): 1
Window Treatments: 1
Above Flood: Yes
Stilt Column Height: Medium - 5Ft - 9Ft
Glass Doors: 1
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Sliding Glass Doors: 1
Covered Parking: 1
Garage: 1
Open Parking: 1
Auto Door Opener: 1
Negotiable: 1
Partially: 1
FKAA: 1
Municipal Sewer: 1
Hot Tub: 1
Outdoor Shower: 1
Rain Gutters: 1
Sandy Beach: 1
Storage: 1
Water Display: 1
Auction: No
Bank Owned: No
Programmable Thermst: 1
Tankless Hot Wtr Htr: 1
Tax Exemptions: Homestead
Dockage: Boat Lift; Davits
Vehicle Storage: Garage; Auto Door Opener; Covered Parking; Off Street Parking; Open Parking
Furnished: Negotiable; Partially
Cooling: Ceiling Fans(s); Central Air
Utilities: FKAA; Municipal Sewer; Propane
Interior Features: Entrance Foyer; Granite Counter Top; Smoke Alarms; Storage; Walk-in Closet(s); Window Treatments
Specialty Rooms: Laundry Room; Loft
Appliances: Dishwasher; Dryer; Gas Appliances; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Chickee Hut; Fencing; Hot Tub; Outdoor Shower; Rain Gutters; Sandy Beach; Storage; Water Display
Pool Info: In Ground; Concrete
Construction: CBS; Concrete; Stucco
Floor: Combo; Marble; Tile
Neighborhood Feature: Airstrip; Bike Paths
Land Size: Less Than 1/4 Acre
GF-Interior Features: Programmable Thermst; Tankless Hot Wtr Htr
Listing Office: Island Real Estate Company Florida Keys
Last Updated: February - 07 - 2026
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