OFF MARKET

Off market mar 2022 for $925K

$1,285,530

Est. refi paymentEst. refi $6,182/mo

•

4,436

sq ft

4400 Pine Top Rd, Taylors Island, MD 21669

About this home

Built with enduring quality and a nautical feel, this spectacular property is perfectly situated to take full advantage of stunning panoramic water views from every room. Presiding gracefully over 4.5 acres of protected higher ground, with over 1,200 feet of natural shoreline on Slaughter Creek, this supremely private property offers quiet moments and water-oriented activities all at once. Inside features include two sunrooms, solid wood doors, walnut floors, new carpet, two fully equipped kitchens, and a waterside breakfast room with a wrap-around built-in bench in a fantastic floor plan that will accommodate gatherings large and small. Robust outdoor amenities continue with an impressive detached 60 x 60 garage boasting four bays that can stack four cars deep, a workshop, office, and an upper loft with light streaming in from full daylight windows all around. Two additional structures with matching siding include a tractor shed with a dual entry and a workshop shed with shelving. Live, work, and play at home with flexibility, beauty, and a truly inspiring waterfront lifestyle. Welcome home to 4400 Pine Tree Road!

Single-familyProperty Type

1993Year Built

4.51 acresLot Size

$290Est. Price/Sq.Ft.

16 garage spacesParking

Listed by Tom Ruch • Northrop Realty

•302-539-0800 (broker)

Bought with Brian Gearhart • Benson & Mangold, LLC

•410-643-3033 (broker)

•info@bensonandmangold.com (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDDO2000874

Redfin Estimate

$1,285,530

$361K since sold in March 2022$50K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 83% higher than the average sale price ($702K) of 6 comparable homes.

SOLD SEP 30, 2026
$502,000
A
4 beds2.5 baths3,088 sq ft
2455 Jurallo Ct, Lusby, MD 20657
SOLD MAY 27, 2026
$600,000
B
5 beds3 baths3,230 sq ft
5511 Casson Neck Rd, Cambridge, MD 21613
SOLD JUL 1, 2026
$490,000
C
4 beds3.5 baths2,966 sq ft
11244 Dancer Ct, Lusby, MD 20657
SOLD AUG 31, 2026
$445,000
D
4 beds2.5 baths2,426 sq ft
1911 Dailsville Rd, Cambridge, MD 21613
SOLD MAY 28, 2026
$527,000
E
5 beds3.5 baths2,944 sq ft
2132 Brians Way, Lusby, MD 20657
SOLD AUG 10, 2026
$1,650,000
F
7 beds6 baths5,920 sq ft
5202 Heron Rd, Cambridge, MD 21613

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Earn from this home

Sell

$534,656

Est. take-home

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Refinance

Est. cash available

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Rent

$4,518/mo

Redfin rental estimate

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Market trends in 21648, MD

Last updated September 2026

Sale-to-list price

100.0%

+7.8% MoM

Median sale price

$275K

$57K MoM

Avg. days on market

138 days MoM

Recently sold homes

0 MoM

Provided by Redfin

Sale history for 4400 Pine Top Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,749 (+22.7%)

$154,900 + $763,300

$918,200

2023

$7,944 (+3.0%)

2022

$7,712 (+3.1%)

$154,900 + $554,100

$709,000

2021

$7,480 (+3.2%)

2020

$7,247

2019

$7,247

$157,000 + $489,300

$646,300

2018

$7,247 (−7.9%)

$157,000 + $489,300

$646,300

2017

$7,869 (−1.1%)

$207,000 + $512,100

$719,100

2015

$7,957

2014

$7,958

$207,000 + $518,900

$725,900

2013

$7,958 (−13.1%)

2012

$9,157 (+20.7%)

2011

$7,588 (−3.9%)

2010

$7,895

2009

$7,895

Tax history for 4400 Pine Top Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,749 (+22.7%)

$154,900 + $763,300

$918,200

2023

$7,944 (+3.0%)

2022

$7,712 (+3.1%)

$154,900 + $554,100

$709,000

2021

$7,480 (+3.2%)

2020

$7,247

2019

$7,247

$157,000 + $489,300

$646,300

2018

$7,247 (−7.9%)

$157,000 + $489,300

$646,300

2017

$7,869 (−1.1%)

$207,000 + $512,100

$719,100

2015

$7,957

2014

$7,958

$207,000 + $518,900

$725,900

2013

$7,958 (−13.1%)

2012

$9,157 (+20.7%)

2011

$7,588 (−3.9%)

2010

$7,895

2009

$7,895

*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

Stories

2.5

Lot width

—

Lot depth

—

Lot size

4.33 Acres

Year renovated

—

Sq. Ft.

4,436

Year built

1993

Style

Single Family Residential

County

Dorchester County

APN

04 056612

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 17, 2026.

Resource Conservation District

The Resource Conservation District is established to conserve natural environments (maritime areas, wetlands and forests) and to encourage resource development activities, such as agriculture, forestry and fisheries, thereby helping to ensure that resource development continues as a long-term land use and a viable economic activity in the county. Residential development at very low density is permitted in the RC District where it is located and designed to respect existing features of the natural landscape. This district includes land within the critical area.

Permitted uses

Include but are not limited to:

Livestock production
Housing-Single unit
Housing-Student
Bed & breakfast
Public service
Recreation
Communications tower
Agriculture-Cropland
Agriculture-Grove / orchard / vineyard
Park & open space

Property details

Parking

Parking Information
# of Attached Garage Spaces: 16
Garage Features: Additional Storage Area, Garage - Side Entry, Oversized
# of Total Garage and Parking Spaces: 32
Has Garage
# of Garage Spaces: 16
Driveway - # of Spaces: 16
Circular Driveway, Gravel Driveway
Attached Garage, Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On 1st Upper Level: 3
# of Bedrooms On 2nd Upper Level: 2

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 2
# of Bathrooms (Half) On 2nd Upper Level: 1
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Half) On All Upper Levels: 1
# of Bathrooms (Full) On All Upper Levels: 2
# of Bathrooms (Half): 2
# of Bathrooms (Full): 3

Interior Information
Appliances: Dryer, Washer, Exhaust Fan, Refrigerator, Icemaker, Oven - Wall, Stove, Built-In Range, Central Vacuum, Commercial Range, Cooktop, Cooktop - Down Draft, Dishwasher, Dryer - Electric, Oven - Single, Oven/Range - Electric, Range Hood, Stainless Steel Appliances, Surface Unit, Extra Refrigerator/Freezer, Oven - Double, Oven - Self Cleaning, Washer - Front Loading, Water Conditioner - Owned, Water Heater
Door Features: Atrium, Six Panel, Sliding Glass, Storm
Flooring Type: Ceramic Tile, Hardwood, Partially Carpeted
Interior Features: 2nd Kitchen, Breakfast Area, Built-Ins, Carpet, CeilngFan(s), Central Vacuum, Dining Area, Family Room Off Kitchen, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Island, Kitchen - Table Space, Master Bath(s), Master Bedroom - Bay Front, Recessed Lighting, Wainscotting, Water Treat System, Window Treatments, Wood Floors, Pantry, Skylight(s), Walk-in Closet(s)
Living Area Sq.Ft. Source: Assessor
Wall & Ceiling Types: 2 Story Ceilings, Paneled Walls, Vaulted Ceilings, Wood Ceilings

Room Information
Living Room, Dining Room, Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Family Room, Foyer, Breakfast Room, Study, Sun/Florida Room, Laundry, Solarium
Laundry Type: Has Laundry, Main Floor

Fireplace Information
Has Fireplace
# of Fireplaces: 3
Wood, Brick, Mantel(s)

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Accessibility Features: Other
Improvement Assessed Value: $489,300
Ownership Interest: Fee Simple
Property Condition: Excellent
Year Built Source: Assessor

Building Information
Construction Materials: Brick, Vinyl Siding
Foundation Details: Block
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Enclosed, Patio(s)
Roof: Architectural Shingle, Metal
Structure Type: Detached
Window Features: Casement, Double Pane, Palladian, Screens, Skylights, Vinyl Clad, Wood Frame

Exterior Information
Boat Storage, Bump-outs, Outbuilding(s), Secure Storage

Lot Information
Lot Features: No Thru Street, Premium, Private, Rear Yard, SideYard(s), Front Yard, Pond, Secluded
Navigable Water
Has Water View
Water Frontage In Feet: 1,200

Land Information
Land Assessed Value: $157,000

Dock Information
Dock Type and Features: Hoist/Lift Electric, Material - Treated Lumber, Mooring, Multiple Slip, Pier, Private, Sun Deck
Dock/Slip Conveyance: Deeded
# of Docks: 1
Dock/Slip Conveys: Yes

Above Grade Information
Finished Sq.Ft.: 4,436
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $7,420
Tax Assessed Value: $667,300
Tax Year: 2021
Tax Annual Amount: $7,420

Assessments Information
Year Assessed: 2021

Utilities

Utilities Information
Central Air
Cooling Type: Ceiling Fan(s), Central A/C, Zoned
Cooling Fuel: Electric
200+ Amp Service
Forced Air, Programmable Thermostat, Zoned
Heating Fuel: Propane - Owned
Hot Water: Electric
Sewer Septic: Shared Septic
Water Source: Well

Location

School Information
Elementary School: MAPLE
Middle Or Junior School: MACE'S LANE
High School: CAMBRIDGE-SOUTH DORCHESTER
School District Name: DORCHESTER COUNTY PUBLIC SCHOOLS
Elementary School Source: Listing Agent
Middle School Source: Listing Agent
High School Source: Listing Agent
School District Source: 3rd Party

Location Information
Outside City Limits
Directions: From MD-16/Cambridge Beltway, the road name will change to Hooper Neck Rd. Turn right to stay on Hooper Neck Rd. Turn right onto Pine Top Rd.

Waterfrontage Information
Water Access Features: Fishing Allowed, Private Access
Water Access
Private Dock Site
On Waterfront
Water Oriented
Water Body Type: River
Water Body Name: Slaughter's Creek

Public facts

Beds: —
Baths: 4.0
Sq. Ft.: 4,436
Stories: 2.5
Lot Size: 4.33 acres
Style: Single Family Residential
Year Built: 1993
Year Renovated: —
County: Dorchester County
APN: 04 056612

Home facts updated by county records on Jul 17, 2026

Around this home

Schools

South Dorchester School

Public PreK-8 • Assigned • 7.8mi

8/10

Cambridge-South Dorchester High School

Public 9-12 • Assigned • 12.2mi

2/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

10/10 Flood Factor

Estimated 80%+ chance 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

9/10 Heat Factor

7 days above 103° expected this year, 16 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

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

Provided by First Street

Historical weather

Taylors Island, MD • 21669

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 9.4 hours in June and 5 hours in December, which is comparable to the U.S. average for solar exposure.

9.4 hrs

5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.22M – $1.48M

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Home values near 4400 Pine Top Rd

Data from public records.

Address	Redfin Estimate
4404 Pine Top Rd, Taylors Island, MD 5 Beds \| 3.5 Baths \| 3817 Sq. Ft.	$905,918
513 Taylors Island Rd, Taylors Island, MD - Beds \| 1 Baths \| 2239 Sq. Ft.	$187,923

Address	Redfin Estimate
4403 Pine Top Rd, Taylors Island, MD - Beds \| 2.5 Baths \| 2736 Sq. Ft.	$679,931
4405 Hall Rd, Taylors Island, MD - Beds \| 2 Baths \| 924 Sq. Ft.	$326,999

Address	Redfin Estimate
4407 Pine Top Rd, Taylors Island, MD 4 Beds \| 2.5 Baths \| 3816 Sq. Ft.	$881,423
Robinson Neck Rd, Taylors Island, MD - Beds \| - Baths \| - Sq. Ft.	$163,189

Property information provided by BRIGHT MLS when last listed in 2021. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 21648, MD

Sale history for 4400 Pine Top Rd

Tax history for 4400 Pine Top Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

Home values near 4400 Pine Top Rd

More real estate resources