With sweeping sunset views, this picturesque estate—perfectly situation on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the property features an impressive two‑story Tidewater Colonial of approximately 3,500± fsf that includes a first‑floor primary suite with a private library, multiple walk‑in closets, and a beautifully finished bath; two additional bedrooms and full bath upstairs; a guest apartment with separate kitchenette, bedroom and full bath; a large two‑car garage; and a stunning concrete pool framed by expansive stone patios. The current owners thoughtfully reimagined and upgraded the interior, relocating the kitchen to the waterside, expanding and renovating the spacious family room and first‑floor primary suite, adding an exceptional bar/butler’s pantry with custom cabinetry, refrigerator, dishwasher, and icemaker, and creating a central multi-purpose laundry room. Exterior features include low‑maintenance brick and siding, new roof on the renovated waterside, paved drive with ample parking, and an attached two‑car garage with a separate climate‑controlled workout room and half bath. The fully protected, riprapped shoreline spans approximately 665 feet and features a new pier with two deepwater slips (6’+ MLW), electric and water service, plus a separate kayak dock and launch. From any of the property’s many vantage points, enjoy majestic shade trees, mature landscaping, and an ever-changing panorama of natural beauty—imagine watching schools of fish and abundant waterfowl daily—making this an ideal Eastern Shore retreat.
For sale
$2,895,000
4440 Baildon Rd, Trappe, MD 21673
4beds
3,589sqft
:
Get pre-qualified$19,088/mo
Single Family Residence
Built in 1968
3.18 Acres Lot
$2,769,400 Zestimate®
$807/sqft
$-- HOA
What's special
Mature landscapingSpacious family roomMajestic shade treesSweeping sunset viewsCentral multi-purpose laundry roomBeautifully finished bath
- 19 days |
- 1,213 |
- 61 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Janet Larson 410-310-1797,
Benson & Mangold, LLC (410) 745-0415
Source: Bright MLS,MLS#: MDTA2014482
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 3
- 1/2 bathrooms: 2
- Main level bathrooms: 3
- Main level bedrooms: 1
Rooms
- Room types: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Library, Foyer, Breakfast Room, Sun/Florida Room, Exercise Room, Laundry, Storage Room, Efficiency (Additional), Primary Bathroom, Full Bath, Half Bath
Primary bedroom
- Features: Flooring - Solid Hardwood, Walk-In Closet(s)
- Level: Main
- Area: 300 Square Feet
- Dimensions: 20 X 15
Bedroom 2
- Features: Flooring - Solid Hardwood, Walk-In Closet(s), Attic - Floored
- Level: Upper
- Area: 270 Square Feet
- Dimensions: 15 X 18
Bedroom 3
- Features: Flooring - Solid Hardwood
- Level: Upper
- Area: 135 Square Feet
- Dimensions: 9 X 15
Bedroom 4
- Features: Flooring - Solid Hardwood, Attached Bathroom
- Level: Upper
- Area: 330 Square Feet
- Dimensions: 15 X 22
Primary bathroom
- Features: Soaking Tub, Bathroom - Stall Shower, Double Sink
- Level: Main
- Area: 108 Square Feet
- Dimensions: 9 X 12
Breakfast room
- Features: Flooring - Solid Hardwood
- Level: Main
- Area: 78 Square Feet
- Dimensions: 6 X 13
Dining room
- Features: Fireplace - Wood Burning, Flooring - Solid Hardwood, Formal Dining Room
- Level: Main
- Area: 294 Square Feet
- Dimensions: 14 X 21
Other
- Level: Upper
Exercise room
- Level: Main
- Area: 112 Square Feet
- Dimensions: 7 X 16
Family room
- Features: Flooring - Solid Hardwood, Fireplace - Gas
- Level: Main
- Area: 288 Square Feet
- Dimensions: 16 X 18
Foyer
- Features: Flooring - Solid Hardwood
- Level: Main
- Area: 126 Square Feet
- Dimensions: 18 X 7
Foyer
- Features: Flooring - Solid Hardwood
- Level: Main
- Area: 147 Square Feet
- Dimensions: 7 X 21
Other
- Features: Flooring - Ceramic Tile, Attic - Floored
- Level: Upper
- Area: 54 Square Feet
- Dimensions: 6 X 9
Other
- Features: Bathroom - Tub Shower
- Level: Upper
- Area: 63 Square Feet
- Dimensions: 7 X 9
Half bath
- Features: Flooring - HardWood
- Level: Main
- Area: 32 Square Feet
- Dimensions: 4 X 8
Half bath
- Level: Main
Kitchen
- Level: Upper
- Area: 54 Square Feet
- Dimensions: 6 X 9
Kitchen
- Features: Flooring - Solid Hardwood, Kitchen Island, Recessed Lighting, Countertop(s) - Quartz, Granite Counters
- Level: Main
- Area: 224 Square Feet
- Dimensions: 14 X 16
Kitchen
- Features: Flooring - HardWood, Wet Bar
- Level: Main
- Area: 75 Square Feet
- Dimensions: 5 X 15
Laundry
- Features: Flooring - Solid Hardwood
- Level: Main
- Area: 70 Square Feet
- Dimensions: 5 X 14
Library
- Features: Flooring - Solid Hardwood, Fireplace - Gas, Built-in Features
- Level: Main
- Area: 176 Square Feet
- Dimensions: 16 X 11
Mud room
- Level: Main
- Area: 99 Square Feet
- Dimensions: 11 X 9
Screened porch
- Features: Flooring - Tile/Brick, Lighting - Pendants
- Level: Main
- Area: 230 Square Feet
- Dimensions: 10 X 23
Storage room
- Level: Upper
Storage room
- Level: Main
- Area: 25 Square Feet
- Dimensions: 5 X 5
Other
- Features: Flooring - Tile/Brick, Ceiling Fan(s), Cathedral/Vaulted Ceiling
- Level: Main
- Area: 221 Square Feet
- Dimensions: 13 X 17
Heating
- Heat Pump, Electric
Cooling
- Central Air, Heat Pump, Ceiling Fan(s), Electric
Appliances
- Included: Microwave, Built-In Range, Range, Dishwasher, Disposal, Dryer, Washer, Exhaust Fan, Extra Refrigerator/Freezer, Instant Hot Water, Double Oven, Oven/Range - Gas, Range Hood, Refrigerator, Six Burner Stove, Stainless Steel Appliance(s), Tankless Water Heater, Water Heater, Electric Water Heater
- Laundry: Main Level, Laundry Room, Mud Room
Features
- 2nd Kitchen, Additional Stairway, Attic, Bar, Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Butlers Pantry, Cedar Closet(s), Ceiling Fan(s), Combination Kitchen/Living, Crown Molding, Entry Level Bedroom, Floor Plan - Traditional, Formal/Separate Dining Room, Eat-in Kitchen, Kitchen - Gourmet, Kitchen Island, Kitchen - Table Space, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-In Closet(s)
- Flooring: Hardwood, Ceramic Tile, Wood
- Doors: French Doors, Six Panel
- Windows: Double Hung, Double Pane Windows, Replacement, Window Treatments
- Has basement: No
- Number of fireplaces: 2
- Fireplace features: Glass Doors, Gas/Propane, Wood Burning
Interior area
- Total structure area: 3,589
- Total interior livable area: 3,589 sqft
- Finished area above ground: 3,589
- Finished area below ground: 0
Property
Parking
- Total spaces: 8
- Parking features: Garage Faces Front, Storage, Garage Door Opener, Inside Entrance, Oversized, Asphalt, Attached, Driveway
- Attached garage spaces: 2
- Uncovered spaces: 6
Accessibility
- Accessibility features: 2+ Access Exits
Features
- Levels: One and One Half
- Stories: 1.5
- Patio & porch: Patio, Porch, Screened Porch
- Exterior features: Chimney Cap(s), Extensive Hardscape, Lighting, Rain Gutters, Sidewalks
- Has private pool: Yes
- Pool features: Concrete, Filtered, In Ground, Private
- Has spa: Yes
- Spa features: Bath
- On waterfront: Yes
- Waterfront features: Private Dock Site, Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, River
- Body of water: Island Creek
- Frontage length: Water Frontage Ft: 665
Lot
- Size: 3.18 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2103121569
- Zoning: RR
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Brick, Stick Built, Vinyl Siding
- Foundation: Crawl Space
- Roof: Architectural Shingle
Condition
- Excellent
- New construction: No
- Year built: 1968
- Major remodel year: 2021
Details
- Builder name: Bruce Harrington
Utilities & green energy
- Sewer: Private Septic Tank, Septic = # of BR
- Water: Well, Private
- Utilities for property: Propane, Fiber Optic
Community & HOA
Community
- Subdivision: Baildon
HOA
- Has HOA: No
Location
- Region: Trappe
Financial & listing details
- Price per square foot: $807/sqft
- Tax assessed value: $1,404,600
- Annual tax amount: $12,464
- Date on market: 7/12/2026
- Listing agreement: Exclusive Right To Sell
- Inclusions: Pool Equipment
- Exclusions: Light Fixture Over Breakfast Room Table
- Ownership: Fee Simple
Estimated market value
$2,769,400
$2.63M - $2.91M
$4,707/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/12/2026 | Listed for sale | $2,895,000+114.4%$807/sqft |
Source:  Bright MLS #MDTA2014482 Report a problem | ||
| 8/21/2015 | Sold | $1,350,000$376/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $1,361,867 +3.2% |
| 2024 | $11,912 +9.1% | $1,319,133 +3.3% |
| 2023 | $10,918 +8.3% | $1,276,400 |
| 2022 | $10,081 +6.5% | $1,276,400 +1.1% |
| 2021 | $9,461 +0.5% | $1,262,867 +0.5% |
| 2020 | $9,411 | $1,256,100 |
| 2019 | $9,411 +4.3% | $1,256,100 |
| 2018 | $9,020 -0.1% | $1,256,100 -5% |
| 2017 | $9,025 +91.9% | $1,321,700 |
| 2016 | $4,703 | $1,321,700 |
| 2015 | $4,703 +2.1% | $1,321,700 -8.2% |
| 2014 | $4,607 | $1,440,400 |
| 2013 | -- | $1,440,400 |
| 2012 | -- | $1,440,400 -17.6% |
| 2011 | -- | $1,747,200 +1.9% |
| 2010 | -- | $1,715,340 -2% |
| 2009 | -- | $1,750,176 +6% |
| 2008 | -- | $1,651,440 +12.9% |
| 2007 | -- | $1,462,652 +14.8% |
| 2006 | -- | $1,273,866 +17.4% |
| 2005 | -- | $1,085,080 +12.2% |
| 2004 | -- | $967,416 +13.8% |
| 2003 | -- | $849,753 +16.1% |
| 2002 | -- | $732,090 +3% |
| 2001 | -- | $710,672 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 21673
Nearby schools
GreatSchools rating
- 9/10White Marsh Elementary SchoolGrades: PK-5Distance: 3 mi
- 4/10Easton Middle SchoolGrades: 6-8Distance: 6.8 mi
- 5/10Easton High SchoolGrades: 9-12Distance: 6.6 mi
Schools provided by the listing agent
- Elementary: White Marsh
- High: Easton
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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A local agent can set up tours, give advice and negotiate with sellers.
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