317 Whitehead St

3,340 Sq. Ft.
$2,064 / Sq. Ft.
3,340
Sq. Ft.
$2,064
per Sq. Ft.

Description

Discover unparalleled luxury in the heart of Old Town, Key West. Comprised of a main house and guest cottage, this newly built ''Smart'' property infuses casual island elegance with modern sophistication. With a total of 6 bedrooms and 6.5 bathrooms, this home is an award winning architect-designed, custom-built luxurious property, complete with off-street parking, impact windows and doors, and is located in the Historic District of Old Town. Entering through your white picket fence, a Chicago brick...Discover unparalleled luxury in the heart of Old Town, Key West. Comprised of a main house and guest cottage, this newly built ''Smart'' property infuses casual island elegance with modern sophistication. With a total of 6 bedrooms and 6.5 bathrooms, this home is an award winning architect-designed, custom-built luxurious property, complete with off-street parking, impact windows and doors, and is located in the Historic District of Old Town. Entering through your white picket fence, a Chicago brick walkway guides you to your spacious front porch, offering views of the Truman Annex and Whitehead Street. A Mahogany front door welcomes you into the main house. The main house is a two story home with White Oak hardwood flooring, and four well appointed bedrooms, each with en suite bathrooms featuring custom millwork. The ground floor is an open plan living, kitchen and dining area with an expansive chef's kitchen, including Miele appliances, column refrigeration and a large entertaining Quartz stone island. Wall-to-wall sliding glass doors open to a luxuriously sized covered, travertine-tiled back patio which includes a lounge seating area, and outdoor kitchen with built-in grill. A heated cocktail plunge pool with waterfall is the perfect spot to cool off after exploring Key West's nearby attractions. The adjacent single-story guest cottage consists of two bedrooms, both with en suite bathrooms. Complete with a private entrance, kitchenette, living area, and private plunge pool hot tub. Additionally, an outdoor shower is just steps away down a private garden path. This property is an entertainer's dream; with professionally designed interiors, and a built-in Sonos speaker sound system throughout, both indoors and outdoors. A quick walk around the block puts you in the absolute center of Key West's action. Hank's, Sloppy Joe's, Mallory Square, and other hot spots are just steps away. Come experience Key West luxury at its finest!
  1. Listed by Bobby W Coe IV • RE/MAX Keys Connection (KW)

Property Details for 317 Whitehead Street

Waterfront
None
Waterfront
No
Zoning
HRO - Historic Residential/Office
Subdivision
Old Town - Unrecord (1.0)
Building Style
Conch
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 10/31/2025 05:25 PM

Property Details for 317 Whitehead Street

StatusActive
MLS #617122
Days on Market79
Taxes$12,071 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built2025
Lot Size0.15 AC / 6,537 SF
CountyMonroe County

Location

Listing Courtesy of RE/MAX Keys Connection (KW)
Add your commute

Building Information for 317 Whitehead Street

Stories-Year Built2025Building Size-Lot Size0.15 AC / 6,537 SF

Payment Calculator

$34,611 per month

30 year fixed, 6.15% Interest

Principal and Interest

$33,605

Property Taxes

$1,006

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 317 Whitehead Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.805032
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Furnished
  • Tax Year: 2024
  • Tax Exemptions: Homestead
Property
Lot Information
  • Acres: 0.15
  • Parcel #: 00004490-000000
  • Land Size: Less Than 1/4 Acre
  • License Info: Non Trans Rntl Lic
Property and Assessments
  • Legal: KW PT LT 3 SQR 25 G71-343/44 G72-528/29 A4-460/61 OR294-445/47 OR491-356/57 OR605-887 OR819-1809/12 OR819-1815/18 OR863-
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Builder/Architect
  • Flood Zone: 0.2 PCT ANNUAL CHANC
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 78
  • Document Count: 1
  • Building Style: Above Flood: Unknown
  • Green Certification: GREEN SEAL
  • Property Condition: New Construction
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Concrete, Salt Water
  • Porch/Balcony: Open Porch/Balcony
Interior and Exterior Features
Interior Features
  • Floor: Wood
  • Interior Features: Drapes/Blinds Incl, Brazilian Quartzite Countertops, Walk-in Closet(s), Storage, Smoke Alarms, Security System, Built-in Cabinets, Pantry
  • Appliances: Washer, Ice Machine, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof, Shingle Roof
  • Construction: Frame, Hardi Board Siding
  • Dockage: None
  • Exterior Features: Bar, Storage, Outdoor Shower, Outdoor Kitchen, Lanai, Hot Tub, Rain Gutters, Detached Guest Qtrs, Fencing, Built-in Grill
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
Room Information
  • Specialty Rooms: Utility Room
  • Specialty Rooms: Guest/Servant Qtrs: Legal

Property History for 317 Whitehead Street

DateEvent & SourcePriceAppreciation
Oct 31, 2025

Listed (Active)

FKMLS #617122

$6,895,000
Nov 1, 2022

Sold

FKMLS #599314

$1,825,000
Nov 1, 2022

Pending

FKMLS #599314

Sep 15, 2022

Backup Contract

FKMLS #599314

Sep 7, 2022

Listed (Active)

FKMLS #599314

Sep 1, 2022

Backup Contract

FKMLS #599314

Jan 24, 2022

Listed (Active)

FKMLS #599314

$2,000,000
May 5, 2021

Sold (Public Record)

Public Record #1461114144

$1,150,000
DateEvent & SourcePrice
10/31/2025

Listed (Active)

FKMLS #617122

$6,895,000
11/01/2022

Sold

FKMLS #599314

$1,825,000
11/01/2022

Pending

FKMLS #599314

09/15/2022

Backup Contract

FKMLS #599314

09/07/2022

Listed (Active)

FKMLS #599314

09/01/2022

Backup Contract

FKMLS #599314

01/24/2022

Listed (Active)

FKMLS #599314

$2,000,000
05/05/2021

Sold (Public Record)

Public Record #1461114144

$1,150,000

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

Public Records for 317 Whitehead Street

Taxable ValueLand$1,340,216Additions$82,048Total$1,422,264
Tax Record2024$12,071 ($1,006 / month)
Home Facts
Beds0Total Finished SqFt760 SqFtAbove Grade Finished SqFt760 SqFtStories2Lot Size6,534 SqFtStyleSingle Family ResidenceYear Built1963Year Renovated1991CountyMONROEAPN00004490-000000

Schools near 317 Whitehead Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - K to 12
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Instruction Program
PublicK to 12

Key West High School
Public9 to 12

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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317 Whitehead Street is a single family home for sale in Key West, FL 33040. This property was listed for sale on October 31, 2025 by RE/MAX Keys Connection (KW), it's currently listed at $6,895,000. It has been on the market for a total of 79 days and was last sold on November 1, 2022. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Instruction Program and Key West High School. 317 Whitehead Street is a 6-bed, 7-bath, 3,340 sqft single family home built in 2025.

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.

Listing Courtesy of RE/MAX Keys Connection (KW)

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.