23941 Henry Street, Summerland, FL

$3,199,000

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3

Beds

2

Baths

2,232

Square feet

About 23941 Henry Street

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.

Features of 23941 Henry Street

MLS® # 617402
Price $3,199,000
Bedrooms 3
Bathrooms 2.00
Full Baths 2
Square Footage 2,232
Year Built 2002
Type Residential
Sub-Type Single Family
Status Active

Community Information

Address 23941 Henry Street
Area 08 - Summerland Key
Subdivision Dobie's Sub (24.0)
City Summerland
County Monroe
State FL
Zip Code 33042

Amenities

Amenities Airstrip, Bike Paths
Utilities FKAA, Propane, Municipal Sewer
Parking Garage, Covered Parking, Open Parking, Auto Door Opener
View Ocean View
Is Waterfront Yes
Waterfront Oceanfront
Has Pool Yes
Pool In Ground, Concrete

Interior

Interior Features Entrance Foyer, Granite Counter Top, Window Treatments, Walk-in Closet(s), Storage, Smoke Alarms
Appliances Washer, Stainless Steel Appliance(s), Gas Appliances, Oven, Range, Refrigerator, Dishwasher, Dryer
Heating Central
Cooling Central Air, Ceiling Fans(s)
Fireplace No
Stories 2 Stories

Exterior

Exterior Features Chickee Hut, Water Display, Storage, Sandy Beach, Outdoor Shower, Hot Tub, Rain Gutters, Fruit Tree(s), Fencing
Lot Description Less Than 1/4 Acre
Windows Glass Doors, Impact Rstnce Window, Impact Rstnce Doors, Sliding Glass Doors
Roof Metal Roof
Construction CBS, Stucco, Concrete
Neighborhood Features Airstrip, Bike Paths

Additional Information

Date Listed November 21st, 2025
Days on Market 13
Zoning IS - Improved Subivision District
Short Sale No
RE / Bank Owned No
HOA Fees 0.00

Listing Details

AgentStacy Shahan
OfficeIsland Real Estate Company Florida Keys

Listing Map

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