Set on a bucolic 5.5-acre lot in the coveted area of Apple Pie Ridge, this beautifully renovated 4-bedroom, 2.5-bath Colonial blends a classic floor plan (2,750 sq. ft. ) with new on-trend updates. Enter to gorgeous new hardwood floors throughout the main level. A spacious, light-filled living room with a wood-burning fireplace flows into the kitchen, which boasts new cabinetry, countertops, and appliances—designed for both storage and a bright, inviting feel. The formal living and dining rooms have been refreshed with re-finished hardwood floors, updated lighting, and fresh paint. Upstairs, every detail is new--hardwoods and carpet, fresh paint, and light fixtures. The large primary bedroom includes a fully renovated ensuite bath with a walk-in glass shower with dual rain shower heads and beautiful tile work. Three additional bedrooms and a completely renovated full bath with new tub, tile, and vanity complete the upper level. Outside, the mostly level 5-acre property is a retreat, offering room for play, gardening, pets, and gatherings. This is a rare opportunity to secure a fully updated home on acreage in one of the area’s most desirable neighborhoods with James Wood High School, Winchester Medical Center, and major commuter routes just minutes away, enjoy country living without sacrificing convenience.
Single-familyProperty Type
1988Year Built
5.56 acresLot Size
$271Est. Price/Sq.Ft.
2 car garageParking
Listed by Rachael Duvall• TTR Sotheby's International Realty
•540-212-9993 (broker)
•theplains@ttrsir.com (broker)
Bought with Jeremy Dalpiaz• Douglas Elliman of Metro DC, LLC - McLean
Welcome home to 505 Glendobbin Rd – a cherished haven nestled in the heart of one of Winchester's most coveted areas-Apple Pie Ridge. This exquisite residence, proudly held by its original owner, now graces the market for the very first time. A testament to timeless care and affection, this home exudes warmth and character in every corner. Situated strategically for the modern commuter, this home offers seamless access to major routes with the convenience of the nearby hospital, schools, shopping and Winchester's historic district. Unfolding across an expansive canvas of five and a half acres, this property is a sanctuary of privacy and tranquility with plenty of mature trees and open land. The possibilities are endless with the lush landscape- whether it's an intimate family picnic or a grand soirée, this sprawling outdoor oasis is primed for all your entertainment aspirations. Walk up the pathway and under the covered front porch to enter inside, where the legacy of love and meticulous upkeep is palpable. While the home has a traditional floor plan, it offers a unique opportunity for the new owners to modernize at their convenience. However, a formal living and dining room, centrally located kitchen and large family room with deck access make this home move-in ready. Upstairs, the primary bedroom along with en suite, which boasts Carrara marble sink tops and a walk-in closet, provide fantastic space with opportunity to personalize. A large bedroom over the garage would be great for guests, a home office, gym or playroom. The unfinished, walk out basement is great for storage with high ceilings, making it a space that could be easily finished. The curb appeal is truly stunning with a large driveway, oversized garage and deck with mountain views. This is your chance to seize the extraordinary – a home that has been cherished by its original owner and is now ready to embrace its new chapter. Homes of this caliber, in this coveted location, are a true rarity. The opportunity is here, the time is now – come experience 505 Glendobbin Rd today! The home has Anderson Windows. Fence updated (2017), D-box replaced (2012), Whole house paint (2021), New well pump (2023), New AC Unit (2021/2013), New basement furnace (2013), H2O softener (2015), Primary bath tile (2017), Architectural Shingles (2006), 1K gallons buried propane tank-owned.
Year
Property tax
Land + Additions
Assessment*
2026
$3,008 (+10.4%)
$146,300 + $421,300
$567,600
2025
$2,724 (+7.9%)
$146,300 + $421,300
$567,600
2024
$2,525
$127,800 + $367,300
$495,100
2023
$2,525 (−1.8%)
$127,800 + $367,300
$495,100
2022
$2,571
$119,500 + $301,900
$421,400
2021
$2,571 (+6.7%)
$119,500 + $301,900
$421,400
2020
$2,410
$119,500 + $275,600
$395,100
2019
$2,410 (+5.4%)
$119,500 + $275,600
$395,100
2018
$2,287 (+1.7%)
$119,500 + $275,600
$395,100
2017
$2,249 (+7.7%)
$120,000 + $254,900
$374,900
2016
$2,088 (+8.5%)
$120,000 + $254,900
$374,900
2014
$1,924
$107,200 + $221,800
$329,000
Tax history for 505 Glendobbin Rd
Year
Property tax
Land + Additions
Assessment*
2026
$3,008 (+10.4%)
$146,300 + $421,300
$567,600
2025
$2,724 (+7.9%)
$146,300 + $421,300
$567,600
2024
$2,525
$127,800 + $367,300
$495,100
2023
$2,525 (−1.8%)
$127,800 + $367,300
$495,100
2022
$2,571
$119,500 + $301,900
$421,400
2021
$2,571 (+6.7%)
$119,500 + $301,900
$421,400
2020
$2,410
$119,500 + $275,600
$395,100
2019
$2,410 (+5.4%)
$119,500 + $275,600
$395,100
2018
$2,287 (+1.7%)
$119,500 + $275,600
$395,100
2017
$2,249 (+7.7%)
$120,000 + $254,900
$374,900
2016
$2,088 (+8.5%)
$120,000 + $254,900
$374,900
2014
$1,924
$107,200 + $221,800
$329,000
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Lot Features: Front Yard, Level, Open, Premium, Private, Rear Yard
Tidal Water: No
Land Information
Land Assessed Value: $146,300
Above Grade Information
Finished Sq.Ft.: 2,786
Finished Sq.Ft. Source: Assessor
Below Grade Information
Unfinished Sq.Ft.: 915
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor
Financial
Tax Information
Agricultural Tax Due: No
County Tax: $2,724
Tax Assessed Value: $567,600
Tax Year: 2025
Tax Annual Amount: $2,724
Assessments Information
Year Assessed: 2025
Lease Information
Lease Considered: No
Utilities
Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Central
Heating Fuel: Propane - Owned
Hot Water: Propane
Sewer Septic: On Site Septic
Propane
Water Source: Well
Municipal Trash: No
Location
School Information
School District Name: FREDERICK COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent
Location Information
Outside City Limits
Directions: From Winchester, Travel North on Rt 522 for 1.8 miles. Turn Right onto Apple Pie Ridge. Travel 1.7 miles and Turn Right onto Glendobbin Rd. House will be on the Left.
Road Responsibility: State
Road Surface Type: Paved
Public facts
Beds: 4
Baths: 2.5
Sq. Ft.: 2,786
Stories: 2.0
Lot Size: 5.56 acres
Style: Single Family Residential
Year Built: 1988
Year Renovated: 2011
County: Frederick County
APN: 43 15 2 1
Home facts updated by county records on Jul 13, 2026
Around this home
Schools
Apple Pie Ridge Elementary School
Public PreK-5 • Assigned • 1.4mi
3/10
Frederick County Middle School
Public 6-8 • Assigned • 5.2mi
2/10
James Wood High School
Public 9-12 • Assigned • 1.6mi
6/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
3/10 Fire Factor
0.15% chance of being in a wildfire in next 30 years
5/10 Heat Factor
7 days above 101° expected this year, 15 days in 30 years
2/10 Wind Factor
1% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Winchester, VA • 22603
Average low and high temperatures (°F)
37
21
44
26
61
38
69
46
72
52
83
62
87
68
80
59
78
55
68
43
57
37
43
27
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.9 hours in
June and 3.7 hours in December, placing it below the
U.S. average for solar exposure.
8.9 hrs
3.7 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$718,000 – $869,000
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