27821 Leeward S Rd

1,175 Sq. Ft.
$979 / Sq. Ft.
1,175
Sq. Ft.
$979
per Sq. Ft.

Description

Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan living room with an abundance of space for entertaining or just relaxing. The lovely kitchen boasts plenty of cabinets, an eat in island, stainless steel...Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan living room with an abundance of space for entertaining or just relaxing. The lovely kitchen boasts plenty of cabinets, an eat in island, stainless steel appliances and granite countertops. The main living area seamlessly flows to large sliding glass pocket doors onto your 50' covered tiled porch. Where you can experience the open water view. Just a few paces down the hall the master suite shares the same spectacular view. Additional highlights include the laundry room on the porch with space for extra storage. Downstairs, a storage enclosure provides ample space for fishing gear, bicycles and all your extras. There is also plenty of covered parking beneath the house keeping vehicles cool and shaded. The yard provides more than enough room for your RV, boat and all your other toys. Add a pool and tiki hut to make this your tropical oasis. RV hookup is also available on the property. Located on a very quiet road with only one neighbor. You are just minutes from a public boat ramp, local restaurants, and a shopping center. Don't miss out on this rare opportunity to own your own generous amount of private property in the Florida Keys.
  1. Listed by Tracy Shields • KeyIsle Realty

Property Details for 27821 Leeward S Road

Waterfront
None
Waterfront
No
Zoning
IS - Improved Subivision District
Subdivision
Misc Little Torch KE (28.0)
Directions
SR4A to Leeward Rd. S. Turn Left on Leeward Rd. S. At the end on the right.
Vehicle Storage
Carport, Trailer Storage, Covered Parking, RV Parking Open, Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 01/14/2026 03:19 PM

Property Details for 27821 Leeward S Road

StatusActive
MLS #618103
Days on Market7
Taxes$2,031 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1991
Lot Size2.41 AC / 104,856 SF
CountyMonroe County

Location

Listing Courtesy of KeyIsle Realty
Add your commute

Building Information for 27821 Leeward S Road

Stories-Year Built1991Building Size-Lot Size2.41 AC / 104,856 SF

Payment Calculator

$5,774 per month

30 year fixed, 6.15% Interest

Principal and Interest

$5,605

Property Taxes

$169

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 27821 Leeward S Road

Summary
Location and General Information
  • Waterview: Bay/Gulf View
  • Area: 10 - Little, Middle, Big Torch Keys
  • Absolute Longitude: 81.39835
  • Control Depth: 0
  • Off Shore Island: No
  • Listing Board: Marathon/Lower Keys
  • Side: Bay/Gulf
  • Mile Marker: 28.0
  • Marathon Neighborhood: N/A
  • Neighborhood Feature: Community Boat Ramp
  • Key/Island: Little Torch Key
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Unfurnished
  • Tax Year: 2025
  • Tax Exemptions: Homestead
Property
Lot Information
  • Acres: 2.38
  • Parcel #: 00113050-000200
  • Land Size: 2 Less Than 5 Acres
Property and Assessments
  • Legal: 20 66 29 PT GOVT LOT 1 LITTLE TORCH KEY (1.38AC)
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE
  • Rentals Allowed: Yes
  • Deed Restrictions: No
  • Picture Count: 32
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: No
  • Porch/Balcony: Open Porch/Balcony, Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile
  • Interior Features: Drapes/Blinds Incl, Smoke Alarms, Granite Counter Top, Built-in Cabinets
  • Pre-Wired: Cable
  • Appliances: Dishwasher, Stainless Steel Appliance(s), Range, Refrigerator
Exterior Features
  • Roof: Metal Roof
  • Shutters: Panel
  • Construction: Frame
  • Dockage: None
  • Exterior Features: Storage
  • Windows/Doors: Sliding Glass Doors
Room Information
  • Specialty Rooms: Workshop

Property History for 27821 Leeward S Road

DateEvent & SourcePriceAppreciation
Jan 14, 2026

Listed (Active)

FKMLS #618103

$1,150,000
Dec 19, 2025

Temp Off Market

FKMLS #615529

Jun 21, 2025

Price Change

FKMLS #615529

$1,800,000
Jun 21, 2025

Price Change

FKMLS #615529

$1,495,000
Jun 21, 2025

Price Change

FKMLS #615529

$1,400,000
Jun 21, 2025

Price Change

FKMLS #615529

$1,200,000
Jun 21, 2025

Listed (Active)

FKMLS #615529

$999,000
Dec 28, 2006

Sold (Public Record)

Public Record #214490716

$45,000
DateEvent & SourcePrice
01/14/2026

Listed (Active)

FKMLS #618103

$1,150,000
12/19/2025

Temp Off Market

FKMLS #615529

06/21/2025

Price Change

FKMLS #615529

$1,800,000
06/21/2025

Price Change

FKMLS #615529

$1,495,000
06/21/2025

Price Change

FKMLS #615529

$1,400,000
06/21/2025

Price Change

FKMLS #615529

$1,200,000
06/21/2025

Listed (Active)

FKMLS #615529

$999,000
12/28/2006

Sold (Public Record)

Public Record #214490716

$45,000

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

Public Records for 27821 Leeward S Road

Taxable ValueLand-Additions-Total-
Tax Record2024$1,937 ($161 / month)
Home Facts
Beds2Baths2Total Finished SqFt896 SqFtAbove Grade Finished SqFt896 SqFtStories2Lot Size60,118 SqFtStyleSingle Family ResidenceYear Built1991Year Renovated2005CountyMONROEAPN00113050-000200

Schools near 27821 Leeward S Road

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

Key West High School
Public9 to 12

Big Pine Academy
CharterPK to 5

The College Of The Florida Keys Academy
Charter9 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.

Similar Homes

Similar Sold Homes

27821 Leeward S Road is a single family home for sale in Summerland Key, FL 33042. This property was listed for sale on January 14, 2026 by KeyIsle Realty, it's currently listed at $1,150,000. It has been on the market for a total of 7 days and was last sold on December 28, 2006. This listing's school district is Monroe. Nearby schools include Sugarloaf School, Key West High School and Big Pine Academy. 27821 Leeward S Road is a 2-bed, 2-bath, 1,175 sqft single family home built in 1991.

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 KeyIsle 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.