For sale

$2,999,999

Est. $19,951/mo —

•

2,009

sq ft

2105 Sheepshead Dr, Naples, FL 34102

About this home

WELCOME TO AN EXCEPTIONAL WATERFRONT OPPORTUNITY IN ROYAL HARBOR—WHERE MOVE-IN-READY COMFORT MEETS UNMATCHED FUTURE POTENTIAL. Perfectly positioned on an oversized pie-shaped homesite with approximately 115 feet of waterfrontage, this beautifully maintained residence offers DIRECT GULF ACCESS via Naples Bay and Gordon Pass, placing world-class boating just minutes from your private 48-foot dock. Offered at LOT VALUE, this property presents a rare opportunity to enjoy the home today while planning a custom waterfront estate in one of Naples' most sought-after boating communities. The existing residence features over 2,000 square feet under air, three en-suite bedrooms, an open-concept floor plan, updated bathrooms, new appliances, abundant natural light, and seamless indoor-outdoor living, all designed to embrace the waterfront lifestyle. Step outside to your private pool, expansive lanai, and generous backyard overlooking the tranquil canal—ideal for entertaining, relaxing, or simply watching boats cruise by. The oversized pie-shaped lot provides exceptional flexibility for future design while maximizing privacy and waterfrontage. Located just minutes from the white-sand beaches of the Gulf, Fifth Avenue South, Third Street South, and the City of Naples, you'll enjoy effortless access to award-winning dining, boutique shopping, arts, and entertainment, all while living in one of Naples' premier waterfront neighborhoods with NO HOA FEES. Whether you're searching for a move-in-ready waterfront retreat, a seasonal escape, or an extraordinary homesite to create your dream estate, this is a rare opportunity to own in Royal Harbor at land-value pricing and experience the very best of the Naples boating lifestyle.

Single-familyProperty Type

1974Year Built

0.32 acresLot Size

$1,493Price/Sq.Ft.

2 car garageParking

Listed by Tiffany McQuaid • Serhant-Naples

Listed by PJ Smith • Serhant-Naples

Listing updated: Aug 29, 2026 at 05:00pm

Redfin checked: a minute ago

•Source:NAPLESMLS #225069719

Payment calculator

$19,951 per month

Principal and interest$15,766

Property taxes

$1,910

HOA dues

Home insurance

$2,275

Utilities

Add

5 minutes to get started. No credit impact.

Discover your buying power

Find out if this home is within budget

Down payment assistance

View down payment assistance programs for this home

See this home in person

This home is unavailable to tour on this day.

Next available date: Tuesday, September 8

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN SAT, 12PM TO 2PM
$430,000
3 beds2 baths1,774 sq ft
3423 Corana Way, Naples, FL 34105
OPEN SAT, 12PM TO 2PM
$309,900
2 beds2 baths842 sq ft
150 Turtle Lake Ct #303, Naples, FL 34105
OPEN SAT, 1PM TO 4PM
$3,190,000
3 beds3 baths2,280 sq ft
430 10th Ave S #305, Naples, FL 34102
OPEN SAT, 2PM TO 3PM
$259,100
3 beds2 baths1,126 sq ft
4420 Botanical Place Cir #402, Naples, FL 34112
OPEN SUN, 12PM TO 2PM
$274,900
2 beds2 baths1,125 sq ft
705 Augusta Blvd #4, Naples, FL 34113
OPEN SUN, 1PM TO 4PM
$1,100,000
3 beds3.5 baths2,845 sq ft
587 Avellino Isles Cir #23101, Naples, FL 34119
OPEN SUN, 1PM TO 4PM
$550,000
2 beds2 baths1,897 sq ft
3904 Forest Glen Blvd Unit 7-101, Naples, FL 34114
OPEN SUN, 1PM TO 4PM
$729,000
3 beds2.5 baths1,980 sq ft
14487 Manchester Dr, Naples, FL 34114
OPEN SUN, 1PM TO 4PM
$8,995,000
4 beds5 baths4,709 sq ft
835 11th Ave S, Naples, FL 34102
OPEN SUN, 1PM TO 4PM
$6,100,000
4 beds3.5 baths3,772 sq ft
570 2nd Ave N, Naples, FL 34102

Around this home

Schools

K - 12
Preschool & daycare

Lake Park Elementary School

Public PreK-5 • Assigned • 3.0mi

10/10

Gulfview Middle School

Public 6-8 • Assigned • 1.8mi

9/10

Naples High School

Public PreK-12 • Assigned • 3.5mi

6/10

Provided by GreatSchools

About Royal

Harbor

Royal Harbor, located between Naples Bay and the Gordon River, is a waterfront and residential Naples neighborhood with deep-water canals and a low-rise, mid-century streetscape. The neighborhood’s character concentrates around the Bayshore Drive S and Tamiami Trail E corridor, where boat yards, design studios, and chef-driven kitchens share the air with working-marina energy. Single-story ranch homes and newer coastal builds line quiet streets, many oriented to docks and seawalls. The Naples Bay Club marina scene sets a nautical cadence for daily routines. Celebration Park’s food-truck pods and waterfront seating add a casual gathering spot. Bayview Park’s boat ramp and shoreline paths keep the geography front and center.

Provided by Walk Score and Local Logic

Market insights

2105 Sheepshead Dr · $2,999,999

DAYS ON MARKET

The average home goes pending in 90 days.

SALE-TO-LIST

Most homes are selling 5% below list price.

LIST PRICE

Median list price in this area is $788,024. (74% lower than this home)

PRICE DROP

16% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Living

Interior features
Cable prewire
French doors
High-speed internet available
Smoke detectors
Walk-in closet
Island in kitchen
Dining area (family)
Family room
Screened lanai/porch
Unfurnished

Bedrooms
3 bedrooms
First-floor bedroom
Split bedroom floor plan

Bathrooms
3 full bathrooms
Master bath with dual sinks and separate tub and shower

Kitchen
Electric cooktop
Dishwasher
Disposal
Microwave
Refrigerator/Freezer
Kitchen island

Laundry & utility
Washer and dryer
Laundry in residence
Auto garage door opener

Flooring
Tile flooring

Heating & cooling
Central electric heat
Central electric cooling
Ceiling fans

Sale and tax history for 2105 Sheepshead Dr

Sale History
Tax History

Date

Event

Price

NAPLESMLS #225069719

Jan 7, 2026

Price Changed

$2,999,999

$1,493/sq ft

Dec 5, 2025

Price Changed

$3,229,200

$1,607/sq ft

Sep 5, 2025

Listed

$3,588,000

$1,786/sq ft

NAPLESMLS #222022654

Apr 28, 2022

Listing Removed

—

Mar 25, 2022

Listed

$4,759,000

$2,369/sq ft

NAPLESMLS #222015072

Mar 25, 2022

Listing Removed

—

Mar 1, 2022

Listed

$4,997,500

$2,488/sq ft

NAPLESMLS #220018860

Jul 31, 2020

Listing Removed

—

Jun 3, 2020

Relisted

—

Apr 27, 2020

Listing Removed

—

Mar 9, 2020

Listed

$1,449,000

$721/sq ft

NAPLESMLS #216013861

May 1, 2016

Listing Removed

—

Mar 28, 2016

Price Changed

$1,499,000

$746/sq ft

Mar 15, 2016

Price Changed

$1,729,000

$861/sq ft

Feb 21, 2016

Listed

$1,749,000

$871/sq ft

Public Records

Jan 7, 2016

Sold

$1,250,000

$622/sq ft

NAPLESMLS #213511643

Jan 15, 2014

Sold

$940,000

$468/sq ft

Jan 15, 2014

Price Changed

$999,985

$498/sq ft

Dec 5, 2013

Listed

$940,000

$468/sq ft

NAPLESMLS #212028793

Nov 30, 2013

Listing Removed

—

Sep 18, 2012

Listed

$1,085,000

$540/sq ft

Public Records

Mar 7, 2005

Sold

$1,685,000

$839/sq ft

Public Records

Oct 11, 2000

Sold

$739,000

$368/sq ft

Public Records

Apr 11, 1994

Sold

$260,000

$129/sq ft

Public record

Public record
Zoning
Permits

Beds

—

Baths

—

Stories

Lot width

—

Lot depth

—

Lot size

0.32 Acres

Year renovated

1974

Finished Sq. Ft.

2,009

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,009

Year built

1974

Style

Single Family Residential

County

Collier County

APN

18361000003

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 12, 2026.

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

10/10 Heat Factor

5 days above 107° expected this year, 18 days in 30 years

10/10 Wind Factor

99% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Naples, FL • 34102

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

93/ 100

Exceptional sunlight

Sunscore

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

9.8 hrs

7.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 2105 Sheepshead Dr

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $1,650,000 and $3,700,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.6M to $3.7M.

SOLD JUN 18, 2026
$2,350,000 Last sold price
3 beds3 baths2,651 sq ft
1275 Cobia Ct, Naples, FL 34102
$607/sq ft
smaller lot
15 years newer
SOLD JUN 26, 2026
$3,700,000 Last sold price
4 beds3.5 baths3,339 sq ft
1807 Snook Dr, Naples, FL 34102
$385/sq ft
larger lot
39 years newer
SOLD AUG 24, 2026
$1,650,000 Last sold price
2 beds2 baths1,435 sq ft
1696 Sandpiper St, Naples, FL 34102
$343/sq ft
smaller lot
5 years older
SOLD SEP 1, 2026
$2,900,000 Last sold price
3 beds3 baths3,302 sq ft
2147 Snook Dr, Naples, FL 34102
$615/sq ft
smaller lot
15 years newer
SOLD OCT 2, 2025
$2,600,000 Last sold price
2 beds2 baths2,327 sq ft
1303 Wahoo Ct, Naples, FL 34102
$376/sq ft
SOLD FEB 12, 2026
$1,775,000 Last sold price
3 beds3 baths2,647 sq ft
3296 Lookout Ln, Naples, FL 34112
$822/sq ft
smaller lot
25 years newer

Tour for free, no strings attached

Takes about 5 minutes & won't affect your credit

Start an offer

(239) 880-2107