23941 Henry Street, Summerland Key, FL 33042 (MLS# 619679)

23941 Henry Street, Summerland Key, FL 33042

New Listing

$2,775,000

38-web-or-mls-27241 Henry St - High Expo

46-web-or-mls-27241 Henry St - High Expo

Property Type: Residential Bedrooms: 3 Baths: 2 Square Footage: 2,232 Lot Size (sq. ft.): 7,188 Status: Active

Current Price: $2,775,000 List Date: 4/29/2026 Last Modified: 4/29/2026

Overview

Description

Oceanfront retreat with sandy beach, protected dockage & direct access to the Ocean & Gulf. Wake each morning to breathtaking Atlantic sunrises and unwind beneath glowing sunsets in this custom-built, two-story CBS oceanfront home. Tucked away on a private street shared by only four residences, this exceptional island inspired sanctuary offers panoramic ocean views, unmatched privacy, and the quintessential Florida Keys lifestyle. The thoughtfully designed home features bright, open-concept living space. Expansive windows, oversized glass doors, and multiple covered porches that flood the interior with natural light while showcasing sweeping ocean views. The chef's kitchen includes stainless steel appliances, tall custom wood cabinetry and generous granite counter space-perfect for entertaining. 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, but ... (Read more)

Listing Details MLS# 619679

Location, Tax & Legal

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
City: Summerland
Mile Marker: 24
Marathon Neighborhood: N/A
Side: Ocean
Flood Zone: AE
Alternate Key #: 1250856
Parcel #: 00188840000000
Zoning: IS - Improved Subivision District
Deed Restrictions: No
Legal: Lt 23 And Adj Portion Of Mary St And Adj Bay Btm Dobies Sub Amended Plat Pb2-135 Summerland Key Or94-21 Or169-502/503 Or
Taxes: 6997.19
Tax Year: 2025
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Marathon/Lower Keys
As is Rght to Inspct: Yes
Potential Short Sale: No
Bank Owned: No

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 3
Pool: Yes
Year Built: 2002
Lot SqFt: 7188
Lot Sqft Source: Property Data Card
Acres: 0.58
Living Apx SqFt: 2232
SqFt Source: Property Data Card
Total Bedrooms: 3
Full Baths: 2
Total Baths: 2
Rentals Allowed: With Restrictions

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

Dockage

Dock Length: 62
Dock: Concrete
Seawall: Concrete
Boat Lift: Yes
Davits: Yes

More Information

Building Style

Above Flood: Yes
Stilt Column Height: Medium - 5Ft - 9Ft
Stories: 2 Stories

Pool Info

Heated: Yes
In Ground: Yes
Concrete: Yes

Financial Status

Auction: No
Bank Owned: No
Potential Short Sale: No

Remarks & Misc

Remarks – Consumer: Oceanfront retreat with sandy beach, protected dockage & direct access to the Ocean & Gulf. Wake each morning to breathtaking Atlantic sunrises and unwind beneath glowing sunsets in this custom-built, two-story CBS oceanfront home. Tucked away on a private street shared by only four residences, this exceptional island inspired sanctuary offers panoramic ocean views, unmatched privacy, and the quintessential Florida Keys lifestyle. The thoughtfully designed home features bright, open-concept living space. Expansive windows, oversized glass doors, and multiple covered porches that flood the interior with natural light while showcasing sweeping ocean views. The chef's kitchen includes stainless steel appliances, tall custom wood cabinetry and generous granite counter space-perfect for entertaining. 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 marble grounds. For boaters, this property is a rare gem. The 62 ft concrete dock offers quick, direct access to both the Ocean and Gulf, along with protected dockage. Features a new 17,000 LB boat lift, 3 additional davits, and approximately 300 ft of bay bottom frontage. This extraordinary oceanfront offering seamlessly blends privacy, tropical elegance, 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.
Directions: MM24 Oceanside

Fee Includes

None: Yes

Tax Exemptions

Homestead: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Gas Appliances: Yes
Oven: Yes
Range: Yes
Refrigerator: Yes
Stainless Steel Appliance(s): Yes
Washer: Yes

Pets

Pets Allowed: Yes

Cooling

Ceiling Fans(s): Yes
Central Air: Yes

Heating

Central: Yes

Waterfront

Oceanfront: Yes

Waterview

Ocean View: Yes

Floor

Combo: Yes
Marble: Yes
Tile: Yes

Neighborhood Feature

Airstrip: Yes
Bike Paths: Yes

Interior Features

Entrance Foyer: Yes
Granite Counter Top: Yes
Smoke Alarms: Yes
Storage: Yes
Walk-in Closet(s): Yes
Window Treatments: Yes

Specialty Rooms

Laundry Room: Yes
Loft: Yes

Windows/Doors

Glass Doors: Yes
Impact Rstnce Doors: Yes
Impact Rstnce Window: Yes
Sliding Glass Doors: Yes

Vehicle Storage

Covered Parking: Yes
Garage: Yes
Open Parking: Yes
Auto Door Opener: Yes
Off Street Parking: Yes

Construction

CBS: Yes
Concrete: Yes
Stucco: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Negotiable: Yes
Partially: Yes

Utilities

Elect Separate Meter: Yes
FKAA: Yes
Municipal Sewer: Yes
Propane: Yes

Porch/Balcony

Open Porch/Balcony: Yes

Title

Negotiable: Yes

Exterior Features

Chickee Hut: Yes
Fencing: Yes
Hot Tub: Yes
Outdoor Shower: Yes
Rain Gutters: Yes
Sandy Beach: Yes
Storage: Yes
Water Display: Yes

Pre-Wired

Cable: Yes

Roof

Metal Roof: Yes

GF-Interior Features

Programmable Thermst: Yes
Tankless Hot Wtr Htr: Yes

Property Features

Fee Includes: None Tax Exemptions: Homestead Waterfront: Oceanfront Waterview: Ocean View 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 Heating: Central Utilities: Elect Separate Meter; FKAA; Municipal Sewer; Propane Interior Features: Entrance Foyer; Granite Counter Top; Smoke Alarms; Storage; Walk-in Closet(s); Window Treatments Pre-Wired: Cable 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 Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Airstrip; Bike Paths Land Size: Less Than 1/4 Acre Title: Negotiable GF-Interior Features: Programmable Thermst; Tankless Hot Wtr Htr

Listing Office: Island Real Estate Company Florida Keys

Last Updated: April - 29 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.