3742 Sea Grape St

4,687 Sq. Ft.
$1,259 / Sq. Ft.
4,687
Sq. Ft.
$1,259
per Sq. Ft.

Description

Breathe in serenity during your escape to the ''The Castle'', a luxurious gated Gulf-front estate gracefully spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a rare blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, PLUS a 95-foot open water pier-style...Breathe in serenity during your escape to the ''The Castle'', a luxurious gated Gulf-front estate gracefully spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a rare blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, PLUS a 95-foot open water pier-style dock with additional 15,000 lb lift and cut-in slip - set against a 130-foot concrete seawall for secure, convenient access. Crafted in 2014 with solid poured concrete, impact-rated windows and doors, whole home generator and elevator, the home is built for enduring elegance. With over 4,600 square feet of refined interior space, this 3-bedroom, 3-bathroom estate is an architect's masterpiece with its stately presence, curved openings, and striking double staircase. Step inside to a breathtaking panorama of endless open Gulf waters and nightly sunset performances. The chef's kitchen is a dream for entertaining, featuring 10.5-foot island with seating for 8, dual sinks, refrigerators, and ovens, plus Jenn-Air 6-burner gas cooktop with pot filler, and rich wood cabinetry. Enjoy the grand family room with Gulf views, host movie nights in the private theater, or dine al-fresco under the stars. Nearby, find the full-size laundry room and storage. The top-floor primary suite is a sanctuary, offering sweeping water views, home office, private lounge with kitchenette, spa-like bath with clawfoot tub, tiled shower and generous walk-in closet with additional laundry. Outside, the resort-style pool beckons with a spa, water features, LED lighting, plus heater and chiller. Rooftop deck with 180-degree views, and unrivaled sunsets await. Offered fully furnished, including a 2023 Sea Cat, 14.5' skiff, and 2015 Chevrolet Silverado - this is ultimate Keys living without compromise!
  1. Listed by Ally Kelley • Ocean Sotheby's International
  2. Listed by Jo Ann Cook • Ocean Sotheby's International

Property Details for 3742 Sea Grape Street

Waterfront
Bay Front, Open Water, Gulf Front
Waterfront
Yes
Zoning
IS - Improved Subivision District
Subdivision
Port Pine Heights (29.0)
Directions
From US-1, right on Key Deer Blvd all the way to Kyle Blvd, left onto Kyle, left onto Sea Grape Street. Property is on right side with gated entry.
Vehicle Storage
Carport, Trailer Storage, Covered Parking, Off Street Parking, Open Parking
Pets
Pets Allowed
LISTING UPDATED: 12/16/2025 03:47 PM

Property Details for 3742 Sea Grape Street

StatusActive
MLS #615356
Days on Market264
Taxes$28,079 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built2014
Lot Size1.14 AC / 49,760 SF
CountyMonroe County

Location

Listing Courtesy of Ocean Sotheby's International
Add your commute

Building Information for 3742 Sea Grape Street

Stories-Year Built2014Building Size-Lot Size1.14 AC / 49,760 SF

Payment Calculator

$31,095 per month

30 year fixed, 6.15% Interest

Principal and Interest

$28,756

Property Taxes

$2,340

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 3742 Sea Grape Street

Summary
Location and General Information
  • Waterview: Bay/Gulf View, Open Water View
  • Area: 11 - Big Pine Key, No Name Key
  • Absolute Longitude: 81.400609
  • Control Depth: 3
  • Off Shore Island: No
  • Listing Board: Marathon/Lower Keys
  • Side: Bay/Gulf
  • Mile Marker: 29.0
  • Marathon Neighborhood: N/A
  • Key/Island: Big Pine Key
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: Voluntary Home Owners Asc: Yes
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Furnished
  • Tax Year: 2024
  • Tax Exemptions: None
Virtual Tour
Property
Lot Information
  • Acres: 1.14
  • Parcel #: 00297040-000000
  • Add'l Parcel #1: SEE DOCUMENTS TAB
  • Land Size: 1 Less Than 2 Acres
Property and Assessments
  • Legal: See Documents Tab
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 111
  • Document Count: 3
  • Building Style: Above Flood: Yes
  • Property Condition: Updated/Remodeled
Utilities
  • Utilities: FKAA, Propane, Cable Available, Whole House Generatr, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Species List: Yes
  • Pool: Yes
  • Handicap Access: No
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Decked, Concrete
  • Porch/Balcony: Open Porch/Balcony, Roof Top Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile
  • Interior Features: Split Bedroom, Built-in Cabinets, Tray Ceilings, Walk-in Closet(s), Smoke Alarms, Security System, Elevator, Granite Counter Top
  • Appliances: Washer, Stainless Steel Appliance(s), Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Concrete Roof
  • Dockage: Dock: Composite
  • Dockage: Seawall: Concrete
  • Construction: CBS
  • Dockage: Boat Lift, Basin, Boat Ramp
  • Exterior Features: Bar, Water Display, Sprinkler System, Privacy Wall/Fence, Outdoor Kitchen, Lighting, Hot Tub, Rain Gutters, Fencing, Built-in Grill
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
Room Information
  • Specialty Rooms: Laundry Room, Utility Room, Media Room

Property History for 3742 Sea Grape Street

DateEvent & SourcePriceAppreciation
Feb 2, 2026

Price Change

MiamiRE #A11877495

$5,900,000
Jun 6, 2025

Price Change

FKMLS #615356

$6,950,000
Jun 6, 2025

Price Change

FKMLS #615356

$6,450,000
Jun 6, 2025

Listed (Active)

FKMLS #615356

$5,900,000
Apr 28, 2025

Listed (Active)

MiamiRE #A11877495

$6,450,000
Feb 1, 2019

Sold

FKMLS #582922

$2,900,000
Jan 2, 2019

Pending

FKMLS #582922

Nov 21, 2018

Listed (Active)

FKMLS #582922

$2,800,000
Mar 21, 2013

Sold

FKMLS #117328

$560,000
Mar 20, 2013

Sold (Public Record)

Public Record #353383356

$560,000
Feb 27, 2013

Pending

FKMLS #117328

Dec 3, 2012

Listed (Active)

FKMLS #117328

$595,500
Apr 1, 2012

Expired

FKMLS #552967

Aug 23, 2010

Temp Off Market

FKMLS #112188

Aug 11, 2010

Listed (Active)

FKMLS #552967

$850,000
Dec 24, 2009

Listed (Active)

FKMLS #112188

$899,000
Nov 16, 2009

Expired

FKMLS #109761

Nov 15, 2009

Expired

FKMLS #547241

Dec 6, 2008

Listed (Active)

FKMLS #547241

$999,000
Dec 2, 2008

Listed (Active)

FKMLS #109761

$999,000
Sep 23, 2004

Sold

FKMLS #521237

$975,000
Aug 14, 2004

Pending

FKMLS #521237

Mar 29, 2004

Listed (Active)

FKMLS #521237

$1,250,000
DateEvent & SourcePrice
02/02/2026

Price Change

MiamiRE #A11877495

$5,900,000
06/06/2025

Price Change

FKMLS #615356

$6,950,000
06/06/2025

Price Change

FKMLS #615356

$6,450,000
06/06/2025

Listed (Active)

FKMLS #615356

$5,900,000
04/28/2025

Listed (Active)

MiamiRE #A11877495

$6,450,000
02/01/2019

Sold

FKMLS #582922

$2,900,000
01/02/2019

Pending

FKMLS #582922

11/21/2018

Listed (Active)

FKMLS #582922

$2,800,000
03/21/2013

Sold

FKMLS #117328

$560,000
03/20/2013

Sold (Public Record)

Public Record #353383356

$560,000
02/27/2013

Pending

FKMLS #117328

12/03/2012

Listed (Active)

FKMLS #117328

$595,500
04/01/2012

Expired

FKMLS #552967

08/23/2010

Temp Off Market

FKMLS #112188

08/11/2010

Listed (Active)

FKMLS #552967

$850,000
12/24/2009

Listed (Active)

FKMLS #112188

$899,000
11/16/2009

Expired

FKMLS #109761

11/15/2009

Expired

FKMLS #547241

12/06/2008

Listed (Active)

FKMLS #547241

$999,000
12/02/2008

Listed (Active)

FKMLS #109761

$999,000
09/23/2004

Sold

FKMLS #521237

$975,000
08/14/2004

Pending

FKMLS #521237

03/29/2004

Listed (Active)

FKMLS #521237

$1,250,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 3742 Sea Grape Street

Taxable ValueLand$1,255,536Additions$2,045,555Total$3,301,091
Tax Record2024$25,730 ($2,144 / month)
Home Facts
Beds3Baths3Total Finished SqFt4,687 SqFtAbove Grade Finished SqFt4,687 SqFtStories3Lot Size17,260 SqFtStyleSingle Family ResidenceYear Built2014Year Renovated2016CountyMONROEAPN00297040-000000

Schools near 3742 Sea Grape Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 6 to 12
Public - 9 to 12
Charter - PK to 5
Rating
School
Distance
Sugarloaf School
PublicPK to 8

Marathon School
Public6 to 12

Key West High School
Public9 to 12

Big Pine Academy
CharterPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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3742 Sea Grape Street is a single family home for sale in Big Pine Key, FL 33043. This property was listed for sale on June 6, 2025 by Ocean Sotheby's International, it's currently listed at $5,900,000. It has been on the market for a total of 264 days and was last sold on February 1, 2019. This listing's school district is Monroe. Nearby schools include Sugarloaf School, Marathon School and Key West High School. 3742 Sea Grape Street is a 3-bed, 3-bath, 4,687 sqft single family home built in 2014.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Ocean Sotheby's International

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.