627 Caroline St

Key West, FL 33040

$5,000,000
Price
5
Beds
2,230 Sq. Ft.
$2,242 / Sq. Ft.
2,230
Sq. Ft.
$2,242
per Sq. Ft.
a front view of a house with a yard
a view of swimming pool from a balcony
a view of a swimming pool with a patio
a room with gym equipment
a view of a livingroom with furniture and a window
a living room with furniture and a flat screen tv
a living room with fireplace furniture and a potted plant
a view of a dining room with furniture window and outside view
a view of a dining room with furniture window and wooden floor
a living room with furniture
a living room with furniture
a kitchen with stainless steel appliances a refrigerator sink and cabinets
a kitchen with stainless steel appliances a counter space and a window
a kitchen with sink refrigerator and window
a living room with furniture or chandelier and a flat screen tv
a bedroom with a large bed and windows
a bedroom with furniture and a window
a bathroom with a sink and mirror
a living room with furniture potted plant and a large window
a view of a livingroom with furniture wooden floor and windows
a living room with furniture and a large window
a bathroom with a shower
a bathroom with a sink and a mirror
a living room with fireplace furniture and a large window
a living room with furniture tv and a large window
a bathroom with a sink and a mirror
41-043
42-044
a view of an entryway with wooden floor and a potted plant
a bedroom with a bed and a large window
a bedroom with a bed and glass door
a bedroom with furniture and a flat screen tv
47-049
a bathroom with a shower and a sink
a bedroom with a bed and wooden floor
a bedroom with a bed and flat screen tv
a view of a hallway with wooden floor and a bathroom
a bedroom with a large bed and a flat tv screen on dresser
a living room with furniture and a flat screen tv
a bathroom with a sink a toilet and shower
a bedroom with a large bed and a window
a bedroom with a bed and a flat screen tv
a bathroom with a sink toilet and shower
a view of a porch
a view of a house with backyard and a patio
a front view of a house with a garden
a view of a dining room with furniture window and outside view
a kitchen with stainless steel appliances a sink dishwasher and cabinets with wooden floor
a view of a porch with furniture and a yard
a front view of a house with garden
a view of a house with a yard
a view of a house with backyard and garden
04-004
a view of a house with backyard porch and sitting area

Description

5 Beds | 6 Baths | Pool & Spa | Prime Historic Location627 Caroline Street is a rare opportunity to own a turnkey masterpiece in one of Key West's most coveted neighborhoods. Just steps from vibrant Duval Street and the iconic Historic Seaport, this fully furnished home perfectly blends timeless island charm with modern luxury. Completely rebuilt from the studs, this residence has been meticulously reimagined with top-tier craftsmanship--preserving its historic architectural features while delivering...5 Beds | 6 Baths | Pool & Spa | Prime Historic Location627 Caroline Street is a rare opportunity to own a turnkey masterpiece in one of Key West's most coveted neighborhoods. Just steps from vibrant Duval Street and the iconic Historic Seaport, this fully furnished home perfectly blends timeless island charm with modern luxury. Completely rebuilt from the studs, this residence has been meticulously reimagined with top-tier craftsmanship--preserving its historic architectural features while delivering the comfort and convenience of new construction. Every inch reflects thoughtful design, from the airy open-concept living spaces to the high-end finishes throughout. Step outside into your private tropical oasis featuring a resort-style pool and spa, ideal for relaxing or entertaining under the Key West sun. Whether you're looking for a luxurious full-time residence, a vacation getaway, or a high-end rental investment, 627 Caroline checks all the boxes. Highlights:
 5 spacious ensuite bedrooms
 6 designer bathrooms
 Stunning pool and spa with lush landscaping
 Off-Street Parking, Fully furnished, and move-in ready
 Premier Old Town location - walk to restaurants, shops, Gym, and the marina
 Seamless blend of historic charm and modern eleganceThis is Key West living at its finest--don't miss your chance to own a piece of paradise.
  1. Listed by Dustan Carpenter • Berkshire Hathaway HomeServices Knight & Gardner Realty

Property Details for 627 Caroline Street

Waterfront
None
Waterfront
No
Zoning
HHDR - Historic High Density Residential
Subdivision
Old Town - Unrecord (1.0)
Pets
Pets Allowed
LISTING UPDATED: 11/22/2025 11:09 AM

Property Details for 627 Caroline Street

StatusActive
MLS #616913
Days on Market72
Taxes$15,074 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1938
Lot Size0.10 AC / 4,541 SF
CountyMonroe County

Location

Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Add your commute

Building Information for 627 Caroline Street

Stories2Year Built1938Building Size-Lot Size0.10 AC / 4,541 SF

Payment Calculator

$25,963 per month

30 year fixed, 6.28% Interest

Principal and Interest

$24,707

Property Taxes

$1,256

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 627 Caroline Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.8024
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Bay/Gulf
  • 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
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.1
  • Parcel #: 00000850-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT LOT 1 SQR 12 OR210-556/57 OR553-1036 OR983-277/79 OR1807-1339/40 OR2725-252/53 OR2899-811/16 OR2905-1400/01 OR2911
  • MLS Approved: Y
  • SqFt Source: Builder/Architect
  • Flood Zone: AE
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 54
  • Document Count: 0
  • Building Style: Above Flood: Unknown
Utilities
  • Utilities: FKAA
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Decked, Salt Water
Interior and Exterior Features
Interior Features
  • Appliances: Dishwasher, Stainless Steel Appliance(s), Microwave, Oven, Refrigerator
Exterior Features
  • Construction: Frame
  • Dockage: None

Property History for 627 Caroline Street

DateEvent & SourcePriceAppreciation
Oct 17, 2025

Listed (Active)

FKMLS #616913

$5,000,000—
Apr 26, 2018

Sold (Public Record)

Public Record #625659237

$1,160,000—
Apr 26, 2018

Sold

FKMLS #579507

$1,160,000—
Apr 25, 2018

Pending

FKMLS #579507

—
Apr 24, 2018

Sold (Public Record)

Public Record #623986669

$1,160,000—
Mar 30, 2018

Sold (Public Record)

Public Record #619311715

$850,100—
Mar 30, 2018

Listed (Active)

FKMLS #579507

$1,395,000—
Nov 8, 2010

Expired

FKMLS #111890

—
Nov 9, 2009

Listed (Active)

FKMLS #111890

$850,000—
DateEvent & SourcePrice
10/17/2025

Listed (Active)

FKMLS #616913

$5,000,000
04/26/2018

Sold (Public Record)

Public Record #625659237

$1,160,000
04/26/2018

Sold

FKMLS #579507

$1,160,000
04/25/2018

Pending

FKMLS #579507

—
04/24/2018

Sold (Public Record)

Public Record #623986669

$1,160,000
03/30/2018

Sold (Public Record)

Public Record #619311715

$850,100
03/30/2018

Listed (Active)

FKMLS #579507

$1,395,000
11/08/2010

Expired

FKMLS #111890

—
11/09/2009

Listed (Active)

FKMLS #111890

$850,000

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

Public Records for 627 Caroline Street

Taxable ValueLand$1,500,710Additions$1,380,682Total$2,881,392
Tax Record2024$15,074 ($1,256 / month)
Home Facts
Beds5Baths2Total Finished SqFt1,974 SqFtAbove Grade Finished SqFt1,974 SqFtStories2Lot Size4,541 SqFtStyleSingle Family ResidenceYear Built1938Year Renovated2023CountyMONROEAPN00000850-000000

Schools near 627 Caroline Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Gerald Adams Elementary School
Public - PK to 5
Monroe Virtual Franchise
Public - 2 to 12
Key West High School
Public - 9 to 12
Monroe Virtual Instruction Program (District Provided)
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Franchise
Public2 to 12

Key West High School
Public9 to 12

Monroe Virtual Instruction Program (District Provided)
PublicK 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.

Similar Homes

Similar Sold Homes

Explore Nearby Homes

More information about 627 Caroline Street, Key West, FL 33040

627 Caroline Street is a single family home for sale in Key West, FL 33040. This property was listed for sale on October 17, 2025 by Berkshire Hathaway HomeServices Knight & Gardner Realty, it's currently listed at $5,000,000. It has been on the market for a total of 72 days and was last sold on April 26, 2018. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Franchise and Key West High School. 627 Caroline Street is a 5-bed, 6-bath, 2,230 sqft single family home built in 1938.

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 Berkshire Hathaway HomeServices Knight & Gardner Realty

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.