OFF MARKET

Off market dec 2022 for $929K

$934,439

Est. refi paymentEst. refi $6,846/mo

•

935

sq ft

3923 Diane Rd, Big Pine Key, FL 33043

About this home

Come see this meticulously renovated waterfront home, secluded in Big Pine. This is a two story home with 55' of waterfront, just minutes to the open water. Upstairs, you will find an open expansive common area, with quartz counters, new cabinets, wine cooler, new appliances, and a master with ensuite and a full bath in hall, with another guest bedroom. Downstairs is for the fun! Full bar, full bath, living area and bedroom/office and two French doors leading to your downstairs tiki area. You'll find a fish cleaning hut, stairs to water, a 10k boat lift, another tiki hut and a real fenced in yard. Hop in your boat and go have fun. New roof in 2018 and 10,000 lb boat lift installed in 2021, as well as impact windows and doors. This house boasts it all – stunning updated home with all the water access you could need!

Single-familyProperty Type

1993Year Built

5,390 sq ftLot Size

$999Est. Price/Sq.Ft.

1 car garageParking

Listed by Lisa Baez • The New Home Spot, Inc.

Bought with Jamie Caudill • Lokation Real Estate

Redfin checked: a few seconds ago

•Source:FLKMLS #602717

Redfin Estimate

$934,439

$5,439 since sold in December 2022$10K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 36.7% higher than the average sale price ($684K) of 6 comparable homes.

SOLD SEP 9, 2026
$789,000
A
2 beds2 baths1,040 sq ft
3922 Gordon Rd, Big Pine Key, FL 33043
SOLD JUL 29, 2026
$650,000
B
2 beds2 baths936 sq ft
3943 Venna Rd, Big Pine Key, FL 33043
SOLD SEP 16, 2026
$438,000
C
2 beds1 bath944 sq ft
29146 Hibiscus Ln, Big Pine Key, FL 33043
SOLD MAY 27, 2026
$805,000
D
2 beds2 baths936 sq ft
29183 Cedar Dr, Big Pine Key, FL 33043
SOLD SEP 16, 2026
$630,000
E
2 beds2 baths1,036 sq ft
29123 Rose Dr, Big Pine Key, FL 33043
SOLD JUL 2, 2026
$790,000
F
2 beds2 baths1,292 sq ft
3686 Gulfstream St, Big Pine Key, FL 33043

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,077/mo

Redfin rental estimate

List your home for rent

Market trends in 33043, FL

Last updated September 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

95.6%

0.5% MoM

Median sale price

$880K

$81K MoM

Avg. days on market

121d

11 days MoM

Recently sold homes

4 MoM

New listings for sale

NEW 15 HRS AGO
$2,750,000
4 beds3.5 baths2,100 sq ft
2131 Coral Way, Big Pine Key, FL 33043
NEW 24 HRS AGO
$1,100,000
3 beds2 baths1,020 sq ft
173 W Cahill Ct, Big Pine Key, FL 33043
3D WALKTHROUGH
$2,450,000
3 beds4 baths2,087 sq ft
31473 Warner St, Big Pine Key, FL 33043
(305) 664-4444
See all

Provided by Redfin

Sale history for 3923 Diane Rd

Date

Event

Price

FLKMLS #602717

Dec 5, 2022

Sold

$929,000

$994/sq ft

Oct 16, 2022

Contingent

—

Oct 10, 2022

Listed

$929,000

$994/sq ft

FLKMLS #587603

Dec 4, 2020

Sold

$395,000

$422/sq ft

Oct 4, 2019

Listed

$415,000

$444/sq ft

+42

FLKMLS #524662

Feb 9, 2005

Sold

$560,000

$599/sq ft

Nov 16, 2004

Listed

$579,000

$619/sq ft

Public Records

Aug 26, 1997

Sold

$140,000

$150/sq ft

Public Records

Apr 14, 1989

Sold

$19,000

$20/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$7,272 (+5.8%)

$354,554 + $420,110

$774,664

2024

$6,876 (−4.3%)

$353,153 + $397,619

$750,772

2023

$7,185 (+144.1%)

$487,687 + $307,433

$795,120

2022

$2,943 (−2.2%)

2021

$3,010 (−13.4%)

$187,788 + $137,997

$325,785

2020

$3,476 (+8.8%)

$173,774 + $159,186

$332,960

2019

$3,195 (+13.6%)

$173,774 + $159,186

$332,960

2018

$2,813 (−13.1%)

$170,432 + $83,170

$253,602

2017

$3,237 (+5.4%)

$167,683 + $133,538

$301,221

2015

$3,070 (+1.3%)

$171,760 + $121,597

$293,357

2014

$3,031

Tax history for 3923 Diane Rd

Year

Property tax

Land + Additions

Assessment*

2025

$7,272 (+5.8%)

$354,554 + $420,110

$774,664

2024

$6,876 (−4.3%)

$353,153 + $397,619

$750,772

2023

$7,185 (+144.1%)

$487,687 + $307,433

$795,120

2022

$2,943 (−2.2%)

2021

$3,010 (−13.4%)

$187,788 + $137,997

$325,785

2020

$3,476 (+8.8%)

$173,774 + $159,186

$332,960

2019

$3,195 (+13.6%)

$173,774 + $159,186

$332,960

2018

$2,813 (−13.1%)

$170,432 + $83,170

$253,602

2017

$3,237 (+5.4%)

$167,683 + $133,538

$301,221

2015

$3,070 (+1.3%)

$171,760 + $121,597

$293,357

2014

$3,031

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

Public record

Public record
Zoning

Beds

Baths

1.5

Stories

Lot width

—

Lot depth

—

Lot size

5,390 Sq. Ft.

Year renovated

2020

Sq. Ft.

1,656

Year built

1993

Style

Single Family Residential

County

Monroe County

APN

0566 29 00291380000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 9, 2026.

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

Parking

Parking / Garage Information
Vehicle Storage: Attached, Off Street Parking, Garage

Interior

Virtual Tour

Interior Features
Interior Features: Bar, Quartz Countertops, Window Treatments, Storage, Cathedral Ceilings, Drapes/Blinds Incl, Built-in Cabinets
Flooring: Laminate, Tile Floor
Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window
Cooling/Heating: Ceiling Fans, Heat, Central A/C
Appliances: Disposal, Washer, Wine Cooler, Microwave, Refrigerator, Range, Oven, Dryer
Furnished: Partially

Bathroom Information
# of Full Baths: 1
# of Half Baths: 1

Specialty Room Information
Specialty Rooms: Laundry Room

Exterior

Boat Slip/Dock Information
Dockage: Dock Length: 55
Dockage: Seawall: Concrete
Dockage: Boat Lift

Exterior Features
Exterior Features: Chickee Hut, Shed, Storage, Fencing, Landscape Lighting
Porch/Balcony: Deck, Screened P/B, Screened Patio

Property Features
Accessibility Features: None
On Waterfront
Waterfront Type: Canal Front
Waterview: Canal View

Property Information
Property Condition: Updated/Remodeled
Deed Restrictions: Unknown
Pets: Pets Allowed
Rentals Allowed: Yes

Lot Information
Acres: 0.12
Zoning: IS - Improved Subivision District
Land Size: Less Than 1/4 Acre
Control Depth: 4
Flood Zone: AE

Building Information
Year Built: 1,993
Sq. Ft. Source: Tax Records
Building Style: Stories: 2
Building Style: Above Flood: Unknown
Construction: Combo Construction
Roof: Shingle Roof

Subdivision/Neighborhood
Subdivision: Port Pine Heights (29.0)
Marathon Neighborhood: N/A

Financial

Tax Information
Taxes: $3,010.41
Tax Year: 2,021
Tax Exemptions: Homestead

Financial Information
Terms: Cash, VA, Conventional

Utilities

Utility Information
Utilities: Cable Available, Elect Separate Meter, Municipal Sewer, FKAA
Pre-Wired: Cable
Has Public Sewer Hook-up

Location

Multi-Unit Information
# of Total Units: 1

Homeowners Association Information
Association Info: 1st Right of Refusal: No
Association Info: Association Fee $: 0.00
Fee Includes: None

Location Information
Side: Bay/Gulf
Mile Marker: 29.00
Directions: From US I, turn on Key Deer. Go left on Kyle, right on No Name, and left on Diane. House is on left.

Public facts

Beds: 2
Baths: 1.5
Sq. Ft.: 1,656
Stories: 2.0
Lot Size: 5,390 square feet
Style: Single Family Residential
Year Built: 1993
Year Renovated: 2020
County: Monroe County
APN: 0566 29 00291380000000

Home facts updated by county records on Oct 9, 2026

Around this home

Schools

Sugarloaf School

Public PreK-8 • Assigned • 9.5mi

6/10

Key West High School

Public 9-12 • Assigned • 26.7mi

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

0.46% 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

Big Pine Key, FL • 33043

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 10 hours in June and 7.3 hours in December, placing it above the U.S. average for solar exposure.

10 hrs

7.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$888,000 – $1.08M

Sell confidently with a local market expert in Big Pine Key. 3 minutes to get started.

Nearby similar homes

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New listings for sale in 33043

NEW 15 HRS AGO

$2,750,000

4 beds3.5 baths2,100 sq ft

2131 Coral Way, Big Pine Key, FL 33043

NEW 24 HRS AGO

$1,100,000

3 beds2 baths1,020 sq ft

173 W Cahill Ct, Big Pine Key, FL 33043

3D WALKTHROUGH

$2,450,000

3 beds4 baths2,087 sq ft

31473 Warner St, Big Pine Key, FL 33043

(305) 664-4444

Home values near 3923 Diane Rd

Data from public records.

Address	Redfin Estimate
3915 Diane Road, Big Pine Key, FL 3 Beds \| 2.5 Baths \| 1500 Sq. Ft.	$937,160
3979 Diane Road, Big Pine Key, FL 2 Beds \| 2 Baths \| 1008 Sq. Ft.	$639,726

Address	Redfin Estimate
3970 Diane Road, Big Pine Key, FL 2 Beds \| 2 Baths \| 936 Sq. Ft.	$611,776
3938 Diane Road, Big Pine Key, FL 3 Beds \| 2 Baths \| 1320 Sq. Ft.	$923,911

Address	Redfin Estimate
3978 Diane Road, Big Pine Key, FL 3 Beds \| 2 Baths \| 1200 Sq. Ft.	$696,025
3861 Gillott Road, Big Pine Key, FL 2 Beds \| 2 Baths \| 1248 Sq. Ft.	$722,859

Property information provided by FLKMLS when last listed in 2022. This data may not match . Learn more.

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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 33043, FL

Sale history for 3923 Diane Rd

Tax history for 3923 Diane Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 33043

Home values near 3923 Diane Rd

More real estate resources