4006 Stewart Road

























































































































Description
Graced by mature specimen trees, apple orchards, and sweeping pastoral views, the main residence has recently been refreshed and features gleaming...Woodwynd – a timeless estate in the Greenspring Valley, available for the first time since 1969. Nestled on 10 bucolic acres on sought-after Stewart Road, Woodwynd offers unparalleled serenity, history, and elegance in the picturesque Greenspring Valley. Built circa 1890, this remarkable property seamlessly blends old-world charm with modern-day comforts.
Graced by mature specimen trees, apple orchards, and sweeping pastoral views, the main residence has recently been refreshed and features gleaming original hardwood floors throughout. Inside, the first floor features a large welcoming foyer, a private office, cozy den, formal dining room, and a spacious living room that opens to a sun-drenched stone porch and inviting sunroom. The heart of the home is a dramatic two-story great room off of the kitchen. It boasts a soaring 28-foot vaulted ceiling and a striking stone fireplace—perfect for gatherings year-round. The large kitchen with breakfast area, plus a mudroom, powder room, and full bath, complete the main level.
Upstairs, the second and third floors offer six well-appointed bedrooms, four full baths, a laundry room, and a flexible bonus space. The serene primary suite includes access to a charming sitting area or sleeping porch, ideal for a home office or possible expanded walk-in closet.
Outside enjoy resort-style living with two koi ponds, a 40-foot pool, hot tub, and a stone patio with pergola—perfect for entertaining under the stars or eating al fresco.
A separate guest house features two bedrooms, a full bath, living room, kitchen, and sunroom leading to a wood deck, ideal for visitors. A large barn and carriage house adds further charm and utility to the property.
Woodwynd is more than a home—it’s a rare opportunity to own a legacy property in one of Maryland’s most coveted and convenient settings. Bring your vision and create your dream estate in Greenspring Valley.
Listing Agent
Property Details for 4006 Stewart Road
Location
Building Information for 4006 Stewart Road
Payment Calculator
$11,131 per month
30 year fixed, 6.55% Interest
$9,657
$1,473
$0
Property Information for 4006 Stewart Road
- In City Limits: No
- School District Name: BALTIMORE COUNTY PUBLIC SCHOOLS
- School District County ID: 121140087473
- SchoolDistrictSource: Listing Agent
- County: BALTIMORE
- Water View: No
- Water Access: No
- Water Oriented: No
- Navigable Water: No
- Tidal Water: No
- Riparian Rights Y/N: No
- Senior Community: No
- Tax Year: 2024
- Tax Assessed Value: $1,534,400
- Improvement Assessed Value: $1,154,100
- Land Assessed Value: $380,300
- Clean Green Assessed: No
- Land Use Code: R
- Zoning: CHECK WITH COUNTY
- School Tax: $0
- Automatically Update Tax Values Y/N: Yes
- # Bathrooms Count Main Level: 2
- # Bathrooms Full Main Level: 1
- # Bathrooms Half Main Level: 1
- # Bedrooms Count All Upper Levels: 6
- # Bathrooms Count All Upper Levels: 4
- # Bathrooms Full All Upper Levels: 4
- # Bedrooms Count Upper Level: 4
- # Bathrooms Count Upper Level: 3
- # Bathrooms Full Upper Level: 3
- # Bedrooms Count Upper Level: 2
- # Bathrooms Count Upper Level: 1
- # Bathrooms Full Upper Level: 1
- Room List: Living Room, Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Den, Basement, Foyer, Breakfast Room, Sun/Florida Room, Great Room, Laundry, Mud Room, Office, Bedroom 6, Bonus Room, Primary Bathroom, Full Bath, Half Bath
- Stories: Main, Upper 1, Upper 2
- Room Type: Foyer
- Room Length: 12.0
- Room Width: 8.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Crown Molding, Lighting - Recessed
- Room Type: Foyer
- Room Length: 18.0
- Room Width: 12.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Built-Ins, Flooring - HardWood
- Room Type: Office
- Room Length: 14.0
- Room Width: 13.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Lighting - Recessed, Built-Ins, Walk-In Closet(s), Flooring - Concrete, Fireplace - Other, Flooring - HardWood
- Room Type: Dining Room
- Room Length: 16.0
- Room Width: 13.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Lighting - Recessed, Fireplace - Other, Flooring - HardWood
- Room Type: Kitchen
- Room Length: 20.0
- Room Width: 12.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - Ceramic Tile, Lighting - Recessed, Countertop(s) - Solid Surface, Pantry
- Room Type: Breakfast Room
- Room Length: 22.0
- Room Width: 15.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - Ceramic Tile, Lighting - Recessed, Lighting - Pendants
- Room Type: Half Bath
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - Ceramic Tile
- Room Type: Mud Room
- Room Length: 14.0
- Room Width: 11.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - Ceramic Tile, Built-Ins
- Room Type: Great Room
- Room Length: 30.0
- Room Width: 27.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - HardWood, Fireplace - Other, Lighting - Track, Flooring - Carpet, Built-Ins, Cathedral/Vaulted Ceiling, Window Treatments
- Room Type: Den
- Room Length: 14.0
- Room Width: 12.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Built-Ins, Fireplace - Other, Flooring - HardWood
- Room Type: Living Room
- Room Length: 27.0
- Room Width: 19.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Crown Molding, Lighting - Recessed, Fireplace - Other, Flooring - HardWood
- Room Type: Sun/Florida Room
- Room Length: 19.0
- Room Width: 9.0
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - Tile/Brick
- Room Type: Primary Bedroom
- Room Length: 27.0
- Room Width: 19.0
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Crown Molding, Fireplace - Other, Walk-In Closet(s), Primary Bedroom - Sitting Area, Flooring - HardWood
- Room Type: Primary Bathroom
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - Ceramic Tile
- Room Type: Sitting Room
- Room Length: 19.0
- Room Width: 9.0
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Primary Bedroom - Sitting Area, Flooring - HardWood
- Room Type: Bedroom 2
- Room Length: 14.0
- Room Width: 14.0
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - HardWood
- Room Type: Bedroom 3
- Room Length: 14.0
- Room Width: 13.0
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Fireplace - Other, Flooring - HardWood
- Room Type: Sitting Room
- Room Length: 13.0
- Room Width: 7.0
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - HardWood
- Room Type: Bedroom 4
- Room Length: 15.0
- Room Width: 14.0
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Fireplace - Other, Walk-In Closet(s), Flooring - HardWood
- Room Type: Full Bath
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - Ceramic Tile
- Room Type: Laundry
- Room Length: 9.0
- Room Width: 9.0
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Built-Ins
- Room Type: Bedroom 5
- Room Length: 14.0
- Room Width: 12.0
- Room Level: Upper 2
- Room Exists: Yes
- Room Features: Flooring - Carpet, Built-Ins
- Room Type: Full Bath
- Room Level: Upper 2
- Room Exists: Yes
- Room Features: Built-Ins
- Room Type: Bedroom 6
- Room Length: 14.0
- Room Width: 12.0
- Room Level: Upper 2
- Room Exists: Yes
- Room Features: Flooring - Carpet, Built-Ins
- Room Type: Bonus Room
- Room Length: 14.0
- Room Width: 11.0
- Room Level: Upper 2
- Room Exists: Yes
- Room Features: Flooring - Carpet, Built-Ins
- Room Type: Basement
- Room Level: Lower 1
- Room Exists: Yes
- Room Features: Basement - Unfinished, Built-Ins, Flooring - Concrete
- Room Type: Full Bath
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Jack and Jill Bathroom, Flooring - Ceramic Tile, Bathroom - Tub Shower, Built-Ins
- Room Type: Full Bath
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - Vinyl, Lighting - Recessed, Built-Ins
- Total Finished SQFT: 8,660.00
- Total Finished SQFT Source: Assessor
- Tax Total Finished SQFT: 8,660.00
- Total SQFT: 11,885.00
- Total SQFT Source: Assessor
- Construction Materials: Shingle Siding
- Roof: Slate
- Wall and Ceiling Types: 2 Story Ceilings, Beamed Ceilings, Vaulted Ceilings
- Flooring Type: Ceramic Tile, Concrete, Hardwood, Other
- Basement Type: Unfinished
- Foundation Details: Active Radon Mitigation
- Room and Floor: 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-Upper Level 1-3, Bedrooms-Upper Level 2-1, Bedrooms-Upper Level 2-2, Bathrooms Full-Upper Level 2-1
- # Bathrooms Full: 5
- # Bathrooms Half: 1
- Other Structure: Barn, Guest House
- Lot Size Source: Assessor
- Lot Features: Front Yard, Landscaping, No Thru Street, Partly Wooded, Private, Rear Yard, SideYard(s), Premium
- Parcel ID: 11719808
- Type Of Parking: Driveway, Off Street, Detached Garage
- Num of Detached Garage Spaces: 3
- Total Garage Spaces: 3
- Parking Features: Lighted Parking, Paved Driveway, Private
- Garage Features: Additional Storage Area, Covered Parking, Oversized
- Interior Features: Breakfast Area, Built-Ins, Crown Moldings, Exposed Beams, Family Room Off Kitchen, Formal/Separate Dining Room, Pantry, Primary Bath(s), Recessed Lighting, Stain/Lead Glass, Bathroom - Stall Shower, Bathroom - Tub Shower, Walk-in Closet(s), Water Treat System, Window Treatments, Wood Floors, Attic, Floor Plan - Traditional, Kitchen - Eat-In, Kitchen - Table Space
- Fireplace: Yes
- Fireplaces Count: 8
- Fireplace Features: Mantel(s), Screen, Stone
- Appliances: Dishwasher, Dryer, Dryer - Front Loading, Exhaust Fan, Extra Refrigerator/Freezer, Microwave, Oven - Double, Oven - Wall, Range Hood, Refrigerator, Six Burner Stove, Washer, Washer - Front Loading, Water Conditioner - Owned, Freezer
- Accessibility Features: None
- Security Features: Security System
- Door Features: Sliding Glass, French
- Laundry Type: Has Laundry, Upper Floor
- Exterior Features: Extensive Hardscape, Exterior Lighting, Hot Tub, Outbuilding(s), Underground Lawn Sprinkler
- Outdoor Living Structures: Deck(s), Patio(s), Porch(es)
- Pool: Yes - Personal
- Utilities: Propane
- Heating: Yes
- Cooling Type: Central A/C, Heat Pump(s), Zoned
- Cooling Fuel: Electric
- Heating Type: Baseboard - Electric, Forced Air, Heat Pump - Oil BackUp, Heat Pump(s), Zoned
- Heating Fuel: Electric, Oil
- Hot Water: Oil
- Water Source: Well
- Sewer Septic: On Site Septic
- List Agent AOR: Greater Baltimore Board of REALTORS
Property History for 4006 Stewart Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Jul 24, 2025 | Closed (Public Record) Public Record #1910165510 | $1,900,000 | — |
| Jul 24, 2025 | Closed BRIGHT #MDBC2128650 | $1,900,000 | — |
| Jun 2, 2025 | Pending BRIGHT #MDBC2128650 | — | |
| Jun 2, 2025 | Active Under Contract BRIGHT #MDBC2128650 | — | |
| May 24, 2025 | Listed (Active) BRIGHT #MDBC2128650 | $2,149,000 | — |
| Nov 30, 2024 | Expired BRIGHT #MDBC2110482 | — | |
| Nov 30, 2024 | Expired BRIGHT #MDBC2102798 | — | |
| Oct 31, 2024 | Price Change BRIGHT #MDBC2110482 | $2,249,000 | — |
| Oct 31, 2024 | Price Change BRIGHT #MDBC2102798 | $2,249,000 | — |
| Oct 19, 2024 | Listed (Active) BRIGHT #MDBC2110482 | $2,500,000 | — |
| Sep 3, 2024 | Listed (Active) BRIGHT #MDBC2102798 | $2,500,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 07/24/2025 | Closed (Public Record) Public Record #1910165510 | $1,900,000 |
| 07/24/2025 | Closed BRIGHT #MDBC2128650 | $1,900,000 |
| 06/02/2025 | Pending BRIGHT #MDBC2128650 | — |
| 06/02/2025 | Active Under Contract BRIGHT #MDBC2128650 | — |
| 05/24/2025 | Listed (Active) BRIGHT #MDBC2128650 | $2,149,000 |
| 11/30/2024 | Expired BRIGHT #MDBC2110482 | — |
| 11/30/2024 | Expired BRIGHT #MDBC2102798 | — |
| 10/31/2024 | Price Change BRIGHT #MDBC2110482 | $2,249,000 |
| 10/31/2024 | Price Change BRIGHT #MDBC2102798 | $2,249,000 |
| 10/19/2024 | Listed (Active) BRIGHT #MDBC2110482 | $2,500,000 |
| 09/03/2024 | Listed (Active) BRIGHT #MDBC2102798 | $2,500,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 4006 Stewart Road
Schools near 4006 Stewart Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | 6 to 8 |
Rating | School | Distance |
|---|---|---|
Woodholme Elementary School PublicPK to 5 | ||
Pikesville Middle School Public6 to 8 | ||
Owings Mills High School Public9 to 12 | ||
Sudbrook Magnet Middle School Public6 to 8 |
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.
Similar Homes
New listings in 21208
Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 4006 Stewart Road, Pikesville, MD 21208 | $1,900,000 | 6 | 6 | 8,660 | 436,907 |
– | – | 4 | 4,108 | 101,059 | |
$650,000 | – | 5 | 3,428 | 419,047 | |
– | – | 3 | 3,038 | 232,610 | |
$1,700,000 | 4 | 7 | 6,268 | 129,373 | |
– | – | 5 | 3,024 | 64,033 | |
– | – | 6 | 7,735 | 248,728 | |
$1,250,000 | 6 | 5 | 4,920 | 310,583 | |
– | – | – | – | 102,802 | |
– | – | 5 | 5,063 | 596,336 | |
– | – | 6 | 7,257 | 216,929 | |
$1,400,000 | – | 6 | 5,860 | 339,332 | |
$1,090,000 | 4 | 5 | – | 232,175 | |
$1,160,000 | 6 | 7 | 7,244 | 190,792 | |
$967,500 | 5 | 5 | 6,468 | 130,244 | |
$45,000 | – | – | – | 43,996 |
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
© 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 07/24/2025 06:14 PM

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