38999 Winodee Way, Hamilton, VA 20158
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Property image
OFF MARKET

38999 Winodee Way
Hamilton, VA 20158

  • 5 Beds
  • 6.5 Baths
  • 6,285 sqft (on 2.45 acres)

$1,584,900

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $9,013/mo*
Refinance Your Home

$1,584,900

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $9,013/mo*
Refinance Your Home
5 Beds
6.5 Baths
6,285 sqft
(on 2.45 acres)

Local Information

  • Map ViewExplore the area around 38999 Winodee Way.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Rare custom-built, architect-designed estate home on 2.45 acres with a pool, **COMCAST internet and NON HOA. Thoughtfully planned for entertaining yet private spaces for working at home, online schooling. Four fireplaces, five bedrooms and six full baths with over 6,200 square feet. Beautiful architectural features include vaulted ceilings, curved walls, two story ceilings, custom beams and trim, Pella windows and doors. Main-level master wing with sitting room/office with built-ins, three-sided fireplace and amazing walk-in closet, private egress to back deck. Updated master bath with newly- installed quartz countertops, high-end 12 x 24 porcelain tile, new Kohler soaking tub and fixtures. Three additional bedrooms with three full baths upstairs. The upstairs bedrooms have lofts that the kids will love for playtime or a great study hideout. Two sets of staircases each to lower and upper levels lend to privacy and easy access. Two walls of windows encompass the updated kitchen with granite, stainless appliances, wood-burning fireplace in sitting area with built-ins. The formal dining room is just off the kitchen with French doors, balcony doors overlooking the pool. Also on the main-level is a private study for additional work-at-home or study space. Large walk-in pantry, laundry room/mudroom and full bath off kitchen. Spacious finished walkout lower level with fifth bedroom, 6th full bath, 3rd wood-burning fireplace, recreation room and additional room for billiards or many uses. Lower level could easily accommodate an in-law suite/separate living quarters. Walkout to pool area with ample patio space for large parties. A tiered deck is off the kitchen for indoor/outdoor entertaining, pool access. Oversized, extra-deep 3 car garage. New roof 2017, exterior painted 2020 and meticulously maintained throughout. Perfect location within half-mile to Route 7, minutes to Leesburg & Toll Rd. Non cookie-cutter here! Checks all the boxes so don't miss this truly unique and well-loved home.
38999 Winodee Way, Hamilton, VA 20158 is a 5 bedroom, 7 bathroom, 6,285 sqft single-family home built in 1991. It last sold for $990,000 on Jan 14, 2021. It is currently off market. The Trulia Estimate is $1,584,900, with a rent estimate of $6,264/month.

Home Highlights

Parking
Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 38999 Winodee Way

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet, Dining Room
Heating & Cooling
Heating: Forced Air, Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDisposal
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodFoundation Type: Concrete
Pool
Pool
Parking & Garage
GarageParking Spaces: 8Parking: Garage Attached

Property Information

Year Built
Year Built: 1991Year Updated: 1995
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 2.45 acres

Price History for 38999 Winodee Way

DatePriceEventSource
01/14/2021$990,000Sold
N/A
11/14/2020$989,000PendingAgent Provided
10/30/2020$989,000PriceChange
Agent Provided
10/09/2020$979,000Listed For SaleAgent Provided
11/11/2018$899,900ListingRemovedAgent Provided
04/13/2018$899,900Listed For SaleAgent Provided

Market trends in Hamilton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
13
1MoM
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Property Tax and Assessment

Year2025
Tax$11,132
Assessment$1,382,910
Home facts updated by county records

Comparable Sales for 38999 Winodee Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
17301 Vannes Ct, Hamilton, VA
0.24
Single-Family Home
$1,200,000
04/23/26
4
3.5
4,261
38822 Bettis Dr, Hamilton, VA
0.44
Single-Family Home
$1,250,000
02/26/26
6
5
5,402
38766 Rambling Farm Dr, Hamilton, VA
0.57
Single-Family Home
$1,325,000
04/30/26
5
4.5
4,916
60 N Tavenner Ln, Hamilton, VA
0.23
Single-Family Home
$850,000
05/04/26
4
3.5
4,387
16943 Heather Knolls Pl, Hamilton, VA
0.86
Single-Family Home
$1,223,000
08/29/25
4
4.5
5,881
17219 Westfield Pl, Hamilton, VA
1.07
Single-Family Home
$1,530,000
06/04/26
5
6
6,419
100 E Colonial Hwy, Hamilton, VA
0.58
Single-Family Home
$940,000
12/31/25
6
3
3,696
17029 Hamilton Station Rd, Hamilton, VA
0.57
Single-Family Home
$1,200,000
09/08/25
3
4.5
3,291
391 E Colonial Hwy, Hamilton, VA
0.27
Single-Family Home
$694,000
03/03/26
3
2.5
2,604
16886 Ivandale Rd, Hamilton, VA
1.10
Single-Family Home
$1,200,000
01/05/26
4
4.5
5,103

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Assigned Schools

These are the assigned schools for 38999 Winodee Way.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Hamilton

At least 13 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 90 % Say car is needed

  • 89 % Say there's holiday spirit

  • 85 % Say parking is easy

  • 83 % Say it's quiet

  • 82 % Say kids play outside

  • 80 % Say yards are well-kept

  • 78 % Say people would walk alone at night

  • 77 % Say they plan to stay for at least 5 years

  • 71 % Say neighbors are friendly

  • 67 % Say there's wildlife

  • 63 % Say there are community events

  • 58 % Say streets are well-lit

  • 52 % Say there are sidewalks

  • 30 % Say it's walkable to restaurants

  • 23 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Carol F. C.
    "Lots of dogs in the neighborhood. Lots of space to run and play and everyone cleans up after Their dogs. "
    0
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  • Carol F. C.
    "We love our neighbors who are always reaching out to help each other, to console when bad things happen, to celebrate birthdays and graduations and other holidays! "
    1
    Flag
  • CollyVee
    "Fantastic neighborhood full of kind folks. Everyone you see greets you with a smile and a handshake. "
    0
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  • CollyVee
    "There’s a great mix from young families with babies to retirees who dote on the neighborhood kids and spoil them on Halloween. Everyone is super welcoming and down to earth. Great community!!"
    0
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  • CollyVee
    "Hamilton day! Our neighborhood has a community picnic where everyone meets up in the common area for a cookout. "
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  • Staciedae
    "Small town that is surrounded by all the necessities. There is actually some sense of community. This is what I was searching for. I am hoping to find the same in where I am moving to, in Dulles, VA."
    0
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  • William L.
    "Hamilton is a quaint little hamlet. Picturesque and sleepy, but convenient to all amenities and with easy access to State Routes 7 and 15. As a town, it is more residential than commercial, but is convenient to shopping in Purcellville (2 miles distant=Giant, Food Lion and Harris Teeter) and Leesburg (six miles distant). A winding road lined by houses of varying architectural styles and historic churches form the central axis."
    0
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  • Kaki P.
    "Loudoun County has everything from neighborhoods close to towns with good schools; small and large farms; historic sites; discount and unique shops; wineries and not far from DC!"
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Apartments for Rent

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Homes for sale near 38999 Winodee Way

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Off Market Homes Near 38999 Winodee Way

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