4404 Pine Top Rd
Description
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,...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!
- Listed by Mark Milligan • RE/Max ExperienceP: (410)-999-5830 markmilliganhomes@gmail.com
Property Details for 4404 Pine Top Road
Property Details for 4404 Pine Top Road
| Status | Closed |
|---|---|
| MLS # | MDDO2008754 |
| Days on Market | 176 |
| Taxes | $8,487 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Single Family |
| MLS Type | Residential / Fee Simple |
| Year Built | 2008 |
| Lot Size | 2.22 AC / 96,703 SF |
| County | Dorchester County |
Location
Sold By Benson & Mangold, LLC
Virtual Tour
Building Information for 4404 Pine Top Road
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$4,402 per month
30 year fixed, 6.15% Interest
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1Property Information for 4404 Pine Top Road
- In City Limits: No
- School District Name: DORCHESTER COUNTY PUBLIC SCHOOLS
- School District County ID: 121139665361
- SchoolDistrictSource: Listing Agent
- County: DORCHESTER
- Water View: No
- Water Access: Yes
- Water Access Features: Canoe/Kayak, Boat - Powered, Swimming Allowed, Personal Watercraft (PWC)
- Water Oriented: Yes
- Navigable Water: Yes
- Tidal Water: Yes
- Water Body Name: Slaughters Creek
- Water Body Type: Creek
- Water Frontage In Feet: 120.0
- Riparian Rights Y/N: No
- Distance To Body Of Water: 40.00
- Distance To Body Of Water Units: Feet
- Senior Community: No
- Tax Year: 2024
- Tax Assessed Value: $763,200
- Year Assessed: 2024
- County Tax: $8,487
- Improvement Assessed Value: $540,900
- Land Assessed Value: $151,800
- Clean Green Assessed: No
- Land Use Code: R
- Zoning: RC
- Tax Lot: 1
- School Tax: $0
- Automatically Update Tax Values Y/N: Yes
- # Bedrooms Count Main Level: 1
- # Bathrooms Count Main Level: 2
- # Bathrooms Full Main Level: 1
- # Bathrooms Half Main Level: 1
- # Bedrooms Count All Upper Levels: 4
- # Bathrooms Count All Upper Levels: 2
- # Bathrooms Full All Upper Levels: 2
- # Bedrooms Count Upper Level: 4
- # Bathrooms Count Upper Level: 2
- # Bathrooms Full Upper Level: 2
- Stories: Main, Upper 1
- Total Finished SQFT: 3,817.00
- Total Finished SQFT Source: Assessor
- Tax Total Finished SQFT: 3,817.00
- Total SQFT: 3,817.00
- Total SQFT Source: Assessor
- Construction Materials: Brick
- Foundation Details: Crawl Space
- Room and Floor: Bedrooms-Main Level-1, Bathrooms Full-Main Level-1, Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bedrooms-Upper Level 1-4, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2
- # Bathrooms Full: 3
- # Bathrooms Half: 1
- Other Structure: Shed Shop
- Lot Size Source: Assessor
- Parcel ID: 5306512
- Ground Rent Exists: No
- Type Of Parking: Detached Garage, Driveway, Attached Garage
- Num of Attached Garage Spaces: 2
- Num of Detached Garage Spaces: 6
- Total Garage Spaces: 8
- Garage Features: Garage - Front Entry
- Fireplace: Yes
- Fireplaces Count: 1
- Accessibility Features: Other
- Virtual Tour URL Unbranded: https://unbranded.youriguide.com/4404_pine_top_rd_taylors_island_md
- Exterior Features: Hot Tub, Outside Shower, BBQ Grill
- Pool: No Pool
- Heating: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Hot Water: Electric
- Water Source: Well
- Sewer Septic: Septic Exists
- List Agent AOR: Anne Arundel County Association of REALTORS
Property History for 4404 Pine Top Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Aug 15, 2025 | Closed BRIGHT #MDDO2008754 | $758,000 | — |
| Aug 13, 2025 | Closed (Public Record) Public Record #1910732303 | $758,000 | +1.7% / yr |
| Jul 9, 2025 | Pending BRIGHT #MDDO2008754 | — | |
| Jul 9, 2025 | Active Under Contract BRIGHT #MDDO2008754 | — | |
| Jun 12, 2025 | Price Change BRIGHT #MDDO2008754 | $800,000 | — |
| Apr 23, 2025 | Price Change BRIGHT #MDDO2008754 | $900,000 | — |
| Mar 30, 2025 | Expired BRIGHT #MDDO2008232 | — | |
| Jan 15, 2025 | Listed (Active) BRIGHT #MDDO2008754 | $925,000 | — |
| Jan 8, 2025 | Withdrawn BRIGHT #MDDO2008232 | — | |
| Oct 15, 2024 | Listed (Active) BRIGHT #MDDO2008232 | $925,000 | — |
| Sep 17, 2020 | Closed (Public Record) Public Record #680379662 | $699,000 | +10.1% / yr |
| Sep 17, 2020 | Closed BRIGHT #MDDO124204 | $699,000 | — |
| Aug 4, 2020 | Pending BRIGHT #MDDO124204 | — | |
| Sep 12, 2019 | Listed (Active) BRIGHT #MDDO124204 | $699,000 | — |
| Feb 12, 2019 | Expired BRIGHT #1000232892 | — | |
| Mar 15, 2018 | Listed (Active) BRIGHT #1000232892 | $725,000 | — |
| Nov 27, 2017 | Withdrawn BRIGHT #1003667177 | $799,500 | — |
| Nov 27, 2017 | Withdrawn BRIGHT #1003667177 | — | |
| Aug 15, 2017 | Listed (Active) BRIGHT #1003667177 | $824,500 | — |
| Apr 12, 2012 | Expired BRIGHT #1006816556 | $999,000 | — |
| Apr 14, 2011 | Listed (Active) BRIGHT #1006816556 | $999,000 | — |
| Nov 21, 2003 | Closed (Public Record) Public Record #125496367 | $138,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 08/15/2025 | Closed BRIGHT #MDDO2008754 | $758,000 |
| 08/13/2025 | Closed (Public Record) Public Record #1910732303 | $758,000 +1.7% / yr |
| 07/09/2025 | Pending BRIGHT #MDDO2008754 | — |
| 07/09/2025 | Active Under Contract BRIGHT #MDDO2008754 | — |
| 06/12/2025 | Price Change BRIGHT #MDDO2008754 | $800,000 |
| 04/23/2025 | Price Change BRIGHT #MDDO2008754 | $900,000 |
| 03/30/2025 | Expired BRIGHT #MDDO2008232 | — |
| 01/15/2025 | Listed (Active) BRIGHT #MDDO2008754 | $925,000 |
| 01/08/2025 | Withdrawn BRIGHT #MDDO2008232 | — |
| 10/15/2024 | Listed (Active) BRIGHT #MDDO2008232 | $925,000 |
| 09/17/2020 | Closed (Public Record) Public Record #680379662 | $699,000 +10.1% / yr |
| 09/17/2020 | Closed BRIGHT #MDDO124204 | $699,000 |
| 08/04/2020 | Pending BRIGHT #MDDO124204 | — |
| 09/12/2019 | Listed (Active) BRIGHT #MDDO124204 | $699,000 |
| 02/12/2019 | Expired BRIGHT #1000232892 | — |
| 03/15/2018 | Listed (Active) BRIGHT #1000232892 | $725,000 |
| 11/27/2017 | Withdrawn BRIGHT #1003667177 | $799,500 |
| 11/27/2017 | Withdrawn BRIGHT #1003667177 | — |
| 08/15/2017 | Listed (Active) BRIGHT #1003667177 | $824,500 |
| 04/12/2012 | Expired BRIGHT #1006816556 | $999,000 |
| 04/14/2011 | Listed (Active) BRIGHT #1006816556 | $999,000 |
| 11/21/2003 | Closed (Public Record) Public Record #125496367 | $138,000 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 4404 Pine Top Road
Schools near 4404 Pine Top Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 8 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
South Dorchester School PublicPK to 8 | ||
Cambridge-South Dorchester High School Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Listing Courtesy of RE/Max Experience
© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 08/17/2025 05:47 PM