Welcome to your dream home on Taylors Island, perfectly situated on the serene Slaughters Creek! This stunning five-bedroom, four-bathroom residence boasts over 3,800 square feet of thoughtfully designed living space, offering both luxury and comfort As you enter, you’ll find a main-level bedroom that overlooks the tranquil water, featuring a jetted soaking tub and a separate shower, complemented by his and hers closets for ample storage. The convenient laundry area is also located on this level, making daily routines seamless The heart of the home is the expansive chef’s kitchen, designed for culinary enthusiasts. It includes an eat-in kitchen area, a gas stove with a pasta faucet, and plenty of counter space for meal prep. The open living area, complete with a cozy gas fireplace, creates an inviting atmosphere for family gatherings and entertaining guests Venture upstairs to discover four additional bedrooms, each offering its own unique charm. Enjoy the outdoors from two spacious exterior sitting decks, perfect for morning coffee or evening sunsets. An exterior shower adds convenience for those coming in from outdoor adventures This property also features an attached garage, an enclosed hot tub for relaxation, and a large detached shed for extra storage. Set on 2.2 acres, you’ll have plenty of space to enjoy a lounge fire pit area, ideal for cozy gatherings under the stars. Plus, with 100 feet of pier access to the water, you’ll have endless opportunities for boating, fishing, and enjoying the natural beauty of your surroundings. Owned solar panels are installed on the backside of the home. The custom outdoor shed is new and has working electric installed. Don’t miss the chance to make this exceptional waterfront home your own! Experience the perfect blend of luxury, comfort, and outdoor living on Taylors Island. Enjoy the BEST crabcakes in Maryland!!
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Sell
$257,834
Est. take-home
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Refinance
$0
Est. cash available
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Rent
$4,224/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
0d
138 days MoM
Recently sold homes
1
0 MoM
Provided by Redfin
Sale history for 4404 Pine Top Rd
Date
Event
Price
BRIGHT MLS #MDDO2008754
Aug 15, 2025
Sold
$758,000
$199/sq ft
Jul 9, 2025
Contingent
—
Jun 12, 2025
Price Changed
$800,000
$210/sq ft
Apr 23, 2025
Price Changed
$900,000
$236/sq ft
Jan 15, 2025
Listed
$925,000
$242/sq ft
Jan 10, 2025
Coming Soon
$925,000
$242/sq ft
BRIGHT MLS #MDDO2008232
Jan 8, 2025
Listing Removed
—
Oct 15, 2024
Listed
$925,000
$242/sq ft
Public Records
Oct 1, 2020
Sold
$699,000
$183/sq ft
BRIGHT MLS #MDDO124204
Sep 23, 2020
Listing Removed
—
Sep 17, 2020
Sold
$699,000
$183/sq ft
Aug 8, 2020
Pending
—
Sep 12, 2019
Listed
$699,000
$183/sq ft
+59
This supremely private waterfront brick Tudor home with panoramic views on three sides offers views of Dave s Creek from the front porch, and even bigger views of Chapel Cove from two sides. Enjoy perfected waterfront living and entertaining with endless venues both indoors and outdoors. Outside, water-oriented amenities and activities are centered around a beautiful natural shoreline, private pier and a 10 x 20 dock sided by two slips and a pontoon lift. A pebble-stone walk from the pier to the house meanders softly past a lush green lawn, flag pole and fire pit. Gather on the waterside patio outfitted with gas for the BBQ, or enjoy the spectacular sunsets on the screened porch. Inside, gather and entertain in grand scale on two levels offering glistening water views at every turn. In addition to the patio and screened porch on the main level, guests will enjoy conversation around an expansive wrap-around island, or, take in the morning views from the custom built-in banquette in the breakfast room adjacent to a gourmet cook s kitchen. Central to the gourmet kitchen is a professional ABA stove, dressed in red with dual gas and electric, and it is completed with a pot filler and feature backsplash. Custom cabinetry is embellished with designer hardware, stove hood, appliance garage, storage tower, and upgraded pull out drawers for spices. Quartz counters surround a stunning black farm sink and gooseneck faucet, with prep sink assist. Upstairs, more entertainment options unfold around a second waterside family room and adjacent wet bar and back bar, with a beverage cooler and a full icemaker. Multiple Pella sliders invite breathtaking panoramic water views from inside as well as from the attached upper deck, perfect for summer breezes, sunsets and stargazing. The central entertainer s wet bar and family room is sided by four bedrooms to accommodate family, friends or overnight guests. After hosting, retire to the private, master suite on the main level. Treat yourself to a spa-like bath in a two-person jetted tub, or choose and invigorating steam shower equipped with music and lights. Radiant floors and a towel warmer stand at the ready for chilly mornings and a second private laundry center is conveniently located just outside of a luxury dressing closet wrapped in wardrobe organizers. Come home to a waterfront home thoughtfully designed to accommodate a variety of lifestyles from hosting groups, to proven revenue producing Air B and B options. This residence offers a rare opportunity for inspired waterfront living.
BRIGHT MLS #1000232892
Nov 5, 2018
Listing Removed
—
May 11, 2018
Price Changed
$699,000
$183/sq ft
Mar 15, 2018
Listed
$725,000
$190/sq ft
BRIGHT MLS #1003667177
Nov 27, 2017
Listing Removed
—
Aug 15, 2017
Listed
$799,500
$209/sq ft
BRIGHT MLS #1006816556
Apr 13, 2012
Listing Removed
—
Apr 14, 2011
Listed
$999,000
$262/sq ft
Public Records
Nov 21, 2003
Sold
$138,000
$36/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$9,581 (+23.4%)
$151,800 + $752,400
$904,200
2023
$7,763 (+5.9%)
2022
$7,334 (+6.2%)
$151,800 + $540,900
$692,700
2021
$6,904 (+6.6%)
2020
$6,475
2019
$6,475
$152,400 + $424,500
$576,900
2018
$6,475 (−7.4%)
$152,400 + $424,500
$576,900
2017
$6,995 (−2.4%)
$202,400 + $436,200
$638,600
2015
$7,166
2014
$7,167
$202,400 + $450,800
$653,200
2013
$7,167 (−7.4%)
2012
$7,743 (+12.6%)
2011
$6,874 (+5.1%)
2010
$6,541
2009
$6,541
Tax history for 4404 Pine Top Rd
Year
Property tax
Land + Additions
Assessment*
2025
$9,581 (+23.4%)
$151,800 + $752,400
$904,200
2023
$7,763 (+5.9%)
2022
$7,334 (+6.2%)
$151,800 + $540,900
$692,700
2021
$6,904 (+6.6%)
2020
$6,475
2019
$6,475
$152,400 + $424,500
$576,900
2018
$6,475 (−7.4%)
$152,400 + $424,500
$576,900
2017
$6,995 (−2.4%)
$202,400 + $436,200
$638,600
2015
$7,166
2014
$7,167
$202,400 + $450,800
$653,200
2013
$7,167 (−7.4%)
2012
$7,743 (+12.6%)
2011
$6,874 (+5.1%)
2010
$6,541
2009
$6,541
*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
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
2.22 Acres
Year renovated
—
Sq. Ft.
3,817
Year built
2008
Style
Single Family Residential
County
Dorchester County
APN
04 063155
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 17, 2026.
RC
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 Detached Garage Spaces: 6
# of Attached Garage Spaces: 2
Garage Features: Garage - Front Entry
# of Total Garage and Parking Spaces: 8
Has Garage
# of Garage Spaces: 8
Detached Garage, Driveway, Attached Garage
Interior
Virtual Tour
Bedroom Information
# of Bedrooms On 1st Upper Level: 4
# of Bedrooms On Main Level: 1
Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 2
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 2
# of Bathrooms (Half): 1
# of Bathrooms (Full): 3
Interior Information
Living Area Sq.Ft. Source: Assessor
Fireplace Information
Has Fireplace
# of Fireplaces: 1
Basement Information
Basement: No
Exterior
Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Accessibility Features: Other
Improvement Assessed Value: $540,900
Ownership Interest: Fee Simple
Year Built Source: Assessor
Building Information
Construction Materials: Brick
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Structure Type: Detached
Other Structures: Shed Shop
Exterior Information
Hot Tub, Outside Shower, BBQ Grill
Lot Information
Navigable Water
Water Frontage In Feet: 120
Tidal Water: Yes
Land Information
Land Assessed Value: $151,800
Above Grade Information
Finished Sq.Ft.: 3,817
Finished Sq.Ft. Source: Assessor
Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor
Financial
Tax Information
County Tax: $8,487
Tax Assessed Value: $763,200
Tax Year: 2024
Tax Annual Amount: $8,487
Assessments Information
Year Assessed: 2024
Utilities
Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Septic Exists
Water Source: Well
Location
School Information
School District Name: DORCHESTER COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent
Location Information
Outside City Limits
Directions: GPS
Waterfrontage Information
Water Access Features: Canoe/Kayak, Boat - Powered, Swimming Allowed, Personal Watercraft (PWC)
Water Access
On Waterfront
Water Oriented
Water Body Type: Creek
Water Body Name: Slaughters Creek
Public facts
Beds: —
Baths: 3.5
Sq. Ft.: 3,817
Stories: 2.0
Lot Size: 2.22 acres
Style: Single Family Residential
Year Built: 2008
Year Renovated: —
County: Dorchester County
APN: 04 063155
Home facts updated by county records on Jul 17, 2026
Around this home
Schools
South Dorchester School
Public PreK-8 • Assigned • 7.9mi
8/10
Cambridge-South Dorchester High School
Public 9-12 • Assigned • 12.3mi
2/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
9/10 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)
39
28
44
31
58
43
67
52
73
60
84
69
88
74
81
68
77
65
69
54
59
46
46
33
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
$861,000 – $1.04M
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