Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,399,000

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 1 Full Bath
  • 1,250 Sq. Ft.
  • Updated 19 hours ago
See This Home
Save This Home
See This Home
Save This Home
Secret Garden Cigar Maker's Cottage in Old Town 🌴 Tucked behind a private gate on a quiet section of Old Town in Key West, this enchanting 2-bedroom historic cottage invites you into a hidden world of tropical beauty, offering a rare blend of privacy, charm, and walkable island living--set in an X flood zone for added peace of mind. Follow a palm-lined path into a lush, private garden oasis filled with orchids, vibrant blooms, and softly glowing evening light. The outdoor pavilion and private deck create an effortless indoor-outdoor lifestyle--complemented by a spa-inspired retreat space designed for open-air relaxation, cooling rinses, and tranquil moments under the palms. Perfect for relaxing, entertaining, or simply enjoying the Key West breeze. Inside, vaulted ceilings, natural light, and original Cuban tile details reflect the home's 1890 cigar-maker heritage, while the updated kitchen features quartz countertops, stainless steel appliances, and garden views. Enjoy the charm of a boutique six-cottage enclave with a shared heated pool and spa. The home offers both connection and quiet escape. Just steps to Duval Street, the Historic Seaport, beaches, and beloved local spots -- leave the car behind and explore on foot or bike. Private. Lush. Magical. Effortlessly Pure Key West

Full Property Details for 1111 Watson St #B

General

  • Price: $1,399,000
  • HOA FEE: $292/month
  • Taxes: $7,271 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 618516
  • Updated: 5/13/2026
  • Added to Site: 97 day(s) ago

Interior

  • Interior Features: Built-in Cabinets, Cathedral Ceilings, Dade County Pine, Drapes/Blinds Incl, Quartz Countertops, Sky Light(s), Smoke Alarms
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Dryer, Microwave, Refrigerator, Washer
  • Flooring: Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 1
  • Full Bathrooms: 1

Bedrooms

  • Total Bedrooms: 2

Additional Information

  • Pool: Yes
  • Pool Description: Heated, In Ground, Decked

Exterior

  • Exterior Features: Hot Tub
  • Deck/Patio: Deck, Patio
  • Porch/Patio/Deck: Deck, Patio

Location

  • Area: 02 - Key West
  • County: Monroe
  • Subdivision: Gwynn Sub (1.0)

Community

  • Association: Yes
  • Assoc. Fees Include: Common Area Mnt
  • Pets Allowed: Yes

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Ductless, Ceiling Fans(s)

Structural Information

  • Architectural Style: Above Flood, Cigar Maker
  • Construction: Frame
  • Roof: Metal
  • Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window, Sliding Glass Doors, Shutters
  • Square Feet: 1,250
  • Sq. Ft. Source: Seller
  • Year Built: 1978

Lot Features

  • Property View: No Waterview
  • Lot Size (Acres): 0.04
  • Lot Size (Sq. Ft.): 1,855
  • Lot Size Source: Tax Records
  • Lot Dimensions: x
  • Zoning: HMDR - Historic Medium Density Residential

Water Features

  • Water View: Yes

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $292
  • Assoc Fee Freq.: Monthly
  • Tax Amount: $7,271.04
  • Tax Year: 2025
  • Terms: Cash, Conventional

Disclosures and Reports

  • Legal Description: KW GWYNN SUB PT OF TRACT 13 PARCEL B & 1/6 INT IN PARCEL H G1-428 G5-237 OR552-279 OR592-857 OR594-276 OR652-254 OR719-3
  • Flood Zone: 0.2 PCT ANNUAL CHANC
  • APN: 00033540-000200

Listed by Keller Williams Key West Compass Realty, Juan Alberto Benitez (305) 587-9230

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 1111 Watson St #B —

  • Juan Alberto Benitez

    Keller Williams Key West Compass Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1111 Watson St #B

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Horace O'bryant School
1105 Leon Street, Key West, FL 33040
6-80.4 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1111 Watson St #B Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/06/2026
Listed
$1,399,000
55.44%
MLS
4/22/2022
Sold
$900,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1111 Watson St #B

Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,623
—
$942,153
8%
2024
$6,623
18%
$875,710
42%
2023
$5,612
32%
$615,390
41%
2021
$4,242
-23%
$435,621
-29%
2022
$5,543
31%
$617,487
41%
2021
$4,242
—
$437,455
1%
2019
$4,238
-5%
$433,342
-3%
2018
$4,456
-17%
$449,010
-20%
2017
$5,353
1%
$558,135
1%
2016
$5,320
5%
$551,947
27%
2015
$5,080
9%
$436,104
10%
2014
$4,656
9%
$396,459
10%
2013
$4,256
—
$360,418
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 1111 Watson St #B

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Keller Williams Key West Compass Realty, Juan Alberto Benitez (305) 587-9230

Similar Properties near 1111 Watson St #B

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

414 Virginia St, Key West, FL 33040 - Photo 1
$1,299,000

414 Virginia St  Key West, FL 33040

  • Single Family
  • Active
  • Updated 7 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,344
    Sq. Ft.
1610 Laird St, Key West, FL 33040 - Photo 1
$1,354,000

1610 Laird St  Key West, FL 33040

  • Single Family
  • Active
  • Updated 16 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,721
    Sq. Ft.
Listed by Sunshine State Realty Services, Roberta A Mira and Sunshine State Realty Services, Melva G Borley
3001 Riviera Dr, Key West, FL 33040 - Photo 1
$1,350,000

3001 Riviera Dr  Key West, FL 33040

  • Single Family
  • Active
  • Updated 14 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,338
    Sq. Ft.
Listed by Truman & Co. (KW), The Spottswood Team
885 Hawksbill Ln, Sugarloaf Key, FL 33042 - Photo 1
$1,399,000

885 Hawksbill Ln  Sugarloaf Key, FL 33042

  • Single Family
  • Active
  • Updated 10 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,398
    Sq. Ft.
Listed by Coastal Collection Real Estate Inc., Tommy Mack

Just Listed near 1111 Watson St #B

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

6800 Maloney Ave, Stock Island, FL 33040 - Photo 1 Just Listed
$534,000

6800 Maloney Ave  #13  Stock Island, FL 33040

  • Mobile Home
  • Active
  • Updated 9 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,222
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Forrest Shearin
4 Coral Dr, Lower Sugarloaf Key, FL 33040 - Photo 1 Just Listed
$450,000
Open House

4 Coral Dr  Lower Sugarloaf Key, FL 33040

  • Mobile Home
  • Active
  • Updated 9 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 873
    Sq. Ft.
Listed by RE/MAX Keys Connection (KW), Bobby W Coe IV and RE/MAX All Keys Real Estate, Kelly Randin
123 Venetian Way, Sugarloaf Key, FL 33042 - Photo 1 Just Listed
$950,000
Open House

123 Venetian Way  Sugarloaf Key, FL 33042

  • Single Family
  • Active
  • Updated 9 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,548
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Angelina Will
17286 Jamaica Ln, Sugarloaf Key, FL 33042 - Photo 1 Just Listed
$1,200,000
Open House

17286 Jamaica Ln  Sugarloaf Key, FL 33042

  • Single Family
  • Active
  • Updated 9 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,344
    Sq. Ft.
Listed by Coldwell Banker Schmitt Real Estate Co, Lisa H Ferringo

Price Reduced near 1111 Watson St #B

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

19267 Hansen Trail, Sugarloaf Key, FL 33042 - Photo 1 Price Reduced
-$100,000 (-9.1%)
$999,000

19267 Hansen Trail  Sugarloaf Key, FL 33042

  • Single Family
  • Active
  • Updated 12 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,968
    Sq. Ft.
Listed by Expert Realty LLC (HQ), Justyn Ewald and Expert Realty LLC (HQ), Mason C Kelly
136 San Remo Dr, Upper Sugarloaf Key, FL 33036 - Photo 1 Price Reduced
-$250,000 (-5.32%)
$4,445,000

136 San Remo Dr  Upper Sugarloaf Key, FL 33036

  • Single Family
  • Active
  • Updated 1 day ago
  • 8
    Beds
  • 4
    Total Baths
  • 4,681
    Sq. Ft.
Listed by Cypress Realty, Inc., Shane Murray Wilson
81250 Overseas Hwy, Upper Sugarloaf Key, FL 33036 - Photo 1 Price Reduced
-$310,000 (-11.92%)
$2,290,000

81250 Overseas Hwy  #5  Upper Sugarloaf Key, FL 33036

  • Single Family
  • Active
  • Updated 7 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,336
    Sq. Ft.
Listed by Palm House Real Estate, AJ Vetter and Palm House Real Estate, Drew Moret
130 N Hammock Rd, Upper Sugarloaf Key, FL 33036 - Photo 1 Price Reduced
-$35,000 (-5.15%)
$645,000

130 N Hammock Rd  Upper Sugarloaf Key, FL 33036

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,376
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices Keys Real Estate - Islamorada, The Lindback Team and Berkshire Hathaway HomeServices Keys Real Estate - Islamorada, Brian Lindback Jr.

Recent Sales near 1111 Watson St #B

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

928 Truman Ave, Key West, FL 33040 - Photo 1 Sold
$1,500,000

928 Truman Ave  #101  Key West, FL 33040

  • Multi-Family
  • Closed
  • Updated 11 hours ago
  • 0.09
    Acres
Listed by Preferred Properties (KW), Allison Findlay
Sold by Berkshire Hathaway HomeServices Knight & Gardner Realty, Louis Condos and Berkshire Hathaway HomeServices Knight & Gardner Realty, Mary Jo Rostien
1011 Truman Ave, Key West, FL 33040 - Photo 1 Sold
$1,300,000

1011 Truman Ave  Key West, FL 33040

  • Commercial
  • Closed
Listed and Sold by Berkshire Hathaway HomeServices Knight & Gardner Realty, Team Gardner/Langley
1332 Duncan St, Key West, FL 33040 - Photo 1 Sold
$1,450,000

1332 Duncan St  Key West, FL 33040

  • Single Family
  • Closed
  • Updated 49 minutes ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,644
    Sq. Ft.
Listed by Keys Atlantic Realty, Derek Epperly, PA
Sold by Truman & Co. (KW), Tonya Cabanas and Truman & Co. (KW), Wendy L Zintsmaster
1107 Olivia St, Key West, FL 33040 - Photo 1 Sold
$1,300,000

1107 Olivia St  Key West, FL 33040

  • Single Family
  • Closed
  • Updated 13 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,125
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Forrest Shearin
Sold by Coastal Collection Real Estate Inc., Tommy Mack

1111 Watson Street #B, Key West, FL 33040 (MLS# 618516) is a Single Family property with 2 bedrooms and 1 full bathroom. 1111 Watson Street #B is currently listed for $1,399,000 and was received on February 06, 2026. Want to learn more about 1111 Watson Street #B? Do you have questions about finding other Single Family real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.

Tour this property