Google street view image for 27821 Leeward Rd S, Little Torch Key, FL 33042

OFF MARKET

$824,976

•

2 ba

•

896

sq ft

27821 Leeward Rd S, Little Torch Key, FL 33042

About this home

27821 Leeward Rd S is a 896 square foot house on a 1.38 acre lot with 2 bedrooms and 2 bathrooms. Based on Redfin's Little Torch Key data, we estimate the home's value is $824,976.

Single-familyProperty Type

1991Year Built

1.38 acresLot Size

$921Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$824,976

$16K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.6% lower than the average sale price ($865K) of 6 comparable homes.

SOLD AUG 31, 2026
$880,000
A
2 beds2 baths912 sq ft
29114 Cedar Dr, Big Pine Key, FL 33043
SOLD JUN 2, 2026
$595,000
B
3 beds2 baths1,104 sq ft
27147 Dolphin Rd, Ramrod Key, FL 33042
SOLD MAY 19, 2026
$1,290,000
C
2 beds2 baths1,344 sq ft
403 Indies Rd, Ramrod Key, FL 33042
SOLD JUL 6, 2026
$1,100,000
D
3 beds3 baths1,222 sq ft
3167 Stewart Rd, Middle Torch Key, FL 33042
SOLD SEP 1, 2026
$813,000
E
3 beds2 baths1,250 sq ft
29115 Rose Dr, Big Pine Key, FL 33043
SOLD JUN 18, 2026
$510,000
F
2 beds2 baths948 sq ft
57 Pelican Ln, Big Pine Key, FL 33043

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Earn from this home

Rent

$3,703/mo

Redfin rental estimate

List your home for rent

Market trends in 33042, FL

Last updated August 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

95.2%

0.7% MoM

Median sale price

$1.1M

$10K MoM

Avg. days on market

136d

16 days MoM

Recently sold homes

4 MoM

New listings for sale

FOR SALE BY OWNER
$2,000,000
4 beds2 baths2,412 sq ft
20843 2nd Ave W, Cudjoe Key, FL 33042
$745,000
2 beds2 baths1,024 sq ft
28441 Meyer Ave, Little Torch Key, FL 33042
$819,500
3 beds2 baths960 sq ft
22968 Drake Ln, Cudjoe Key, FL 33042
3D WALKTHROUGH
$2,099,000
4 beds3.5 baths2,548 sq ft
1106 Thatch Ln, Cudjoe Key, FL 33042
$982,600
2 beds2 baths864 sq ft
701 Spanish Main Dr #198, Cudjoe Key, FL 33042
$899,000
2 beds1 bath902 sq ft
24923 Park Dr, Summerland Key, FL 33042
See all

Provided by Redfin

Sale history for 27821 Leeward Rd S

Date

Event

Price

FLKMLS #618103

Jun 9, 2026

Listing Removed

—

Mar 6, 2026

Price Changed

$1,125,000

$1,256/sq ft

Jan 14, 2026

Listed

$1,150,000

$1,283/sq ft

FLKMLS #615529

Dec 17, 2025

Listing Removed

—

Nov 3, 2025

Price Changed

$1,200,000

$1,339/sq ft

Sep 20, 2025

Price Changed

$1,400,000

$1,563/sq ft

Sep 19, 2025

Price Changed

$999,000

$1,115/sq ft

Jul 26, 2025

Price Changed

$1,495,000

$1,669/sq ft

Jun 21, 2025

Listed

$1,800,000

$2,009/sq ft

Tax history for 27821 Leeward Rd S

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Zoning

Improved Subdivision District

The purpose of the IS district is to accommodate the legally vested residential development rights of the owners of lots in subdivisions that were lawfully established and improved prior to the adoption of this LDC. For the purpose of this section, improved lots are those that are served by a dedicated and accepted existing road of porous or nonporous material, that have an approved potable water supply, and that have sufficient uplands to accommodate the proposed use in accordance with the required setbacks. This district is not intended to be used for new land use districts of this classification within the county.

Zone overlays

Industrial District

Permitted uses

Include but are not limited to:

Housing-Multiple units
Infrastructure

Property details

Interior

Bathroom Information
# of Full Baths: 2

Heating & Cooling
Heating Type: Forced Air

Exterior

Exterior Information
Physical Condition: Average
Floor Construction Type: Plywood
Foundation Type: Concrete
Exterior Wall: Wood
Roof Shape Type: Gable/Hip
Building Type: Residential

Property Information
Subdivision Name: LITTLE TORCH KEY
Living Sq. Ft: 896
Gross Sq. Ft: 3,256
Ground Floor Sq. Ft: 896
Building Sq. Ft: 896
# of Units: 1
# of Stories: 2
Legal Description: 20 66 29 PT GOVT LOT 1 LITTLE TORCH KEY (1.38AC) OR775-542 OR886-36 OR1144-1971 OR1589-1240 OR1996-2247/2248 OR2724-129/30 OR3132-0587

Parking & Garage Information
Garage/Parking Sq. Ft: 905

Lot Information
# of Buildings: 1
Land Sq. Ft: 60,113
Legal Lot Number: 1
Municipality Type: LTK
Municipality Name: RAMROD KEY-BIG TORCH KEY-MIDDL
Acres: 1.38
Zoning Code: IS
County Use Description: SINGLE FAMILY RES
State Use Description: SINGLE FAMILY

Financial

Assessor Information
Assessment Year: 2025
Tax District County: RAMROD KEY-BIG TORCH KEY-MIDDL
Tax Area: RAMROD KEY-BIG TORCH KEY-MIDDL

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 896
Stories: 2.0
Lot Size: 1.38 acres
Style: Single Family Residential
Year Built: 1991
Year Renovated: 2005
County: Monroe County
APN: 2066 29 00113050000200

Home facts updated by county records on Jul 10, 2026

Around this home

Schools

Sugarloaf School

Public PreK-8 • Assigned • 8.4mi

6/10

Key West High School

Public 9-12 • Assigned • 25.4mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

Heat Factor

We're working on getting current and accurate heat risk information for this home.

10/10 Wind Factor

99% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Little Torch Key, FL • 33042

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

100/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.7 hrs

7.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$784,000 – $949,000

Sell confidently with a local market expert in Little Torch Key. 3 minutes to get started.

Nearby similar homes

$899,000

3 beds2 baths1,418 sq ft

1540 Lantana Ln, Big Pine Key, FL 33043

$840,000

2 beds2 baths1,048 sq ft

3635 Trade Winds St, Big Pine Key, FL 33043

(305) 809-8085

$1,499,000

3 beds3 baths1,596 sq ft

21007 4Th Ave, Cudjoe Key, FL 33042

$1,185,000

3 beds2 baths1,188 sq ft

706 E Caribbean Dr, Summerland Key, FL 33042

$1,550,000

3 beds2 baths1,392 sq ft

29424 Forrestal Ave, Big Pine Key, FL 33043

NEW CONSTRUCTION

$1,549,000

3 beds3 baths1,500 sq ft

27374 Guadaloupe Ln, Ramrod Key, FL 33042

New listings for sale in 33042

FOR SALE BY OWNER

$2,000,000

4 beds2 baths2,412 sq ft

20843 2nd Ave W, Cudjoe Key, FL 33042

$745,000

2 beds2 baths1,024 sq ft

28441 Meyer Ave, Little Torch Key, FL 33042

$819,500

3 beds2 baths960 sq ft

22968 Drake Ln, Cudjoe Key, FL 33042

3D WALKTHROUGH

$2,099,000

4 beds3.5 baths2,548 sq ft

1106 Thatch Ln, Cudjoe Key, FL 33042

$982,600

2 beds2 baths864 sq ft

701 Spanish Main Dr #198, Cudjoe Key, FL 33042

$899,000

2 beds1 bath902 sq ft

24923 Park Dr, Summerland Key, FL 33042

Home values near 27821 Leeward Rd S

Data from public records.

Address	Redfin Estimate
27942 Leeward Road South, Little Torch Key, FL 2 Beds \| 2 Baths \| 1160 Sq. Ft.	$1,014,306
27838 Lobster Tail Trail, Little Torch Key, FL 2 Beds \| 2 Baths \| 1008 Sq. Ft.	$701,400

Address	Redfin Estimate
27818 Lobster Tail Trail, Little Torch Key, FL 3 Beds \| 2 Baths \| 1150 Sq. Ft.	$652,032
27823 Coral Shores Road, Little Torch Key, FL 3 Beds \| 2 Baths \| 1250 Sq. Ft.	$489,991

Address	Redfin Estimate
27828 Lobster Tail Trail, Little Torch Key, FL 2 Beds \| 2 Baths \| 904 Sq. Ft.	$426,233
27895 Coral Shores Road, Little Torch Key, FL 2 Beds \| 2 Baths \| 797 Sq. Ft.	$621,922

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 33042, FL

Sale history for 27821 Leeward Rd S

Tax history for 27821 Leeward Rd S

Zoning

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 33042

Home values near 27821 Leeward Rd S

More real estate resources