529 Jefferson Street

Winchester, VA
$ 1,475,000 Beds 4 Baths 4.5 Sq 5,037
Monthly Estimate* How much can I afford?

Carter Hill Manor, Conveniently located just minutes from old town Winchester is a Georgian Revival, built of rose brick with hipped Virginia slate roof was designed by Fredericksburg architect Philip N. Stern. The Jefferson St. address was planned to be the rear of the home, while the front opened on to "Old Lane" and the expansive three acres of stone walls, lawn, and gardens. Sitting on one of the Winchester's highest points, where there were previously apple orchards, now boasts a rolling landscape of mature plantings, flowering cherries, yellow peonies, weeping lilacs, and lavender rock garden. These lovely grounds surround and protect the home creating a private oasis, which is especially delightful for entertaining. Architectural details abound throughout the home, from hardwood floors, old-world fireplaces, paneled doors, dental moldings, chair-rail, and paneled walls throughout the interior. There are spaces for family living and entertaining as well as quiet and private corners. The first floor features a center hallway and entry with beautiful curved stairway and entry both on the east and west side of the home The entry is flanked on the south-side by the formal living room and dining room on the north-side. Pass-thru a light-filled sunroom to the quiet and private library with wet bar and private entry. Once through the dining room, you enter into the large breakfast, family, and kitchen space. Again a light-filled room with room for family gathering, media, and dining in the lovely country kitchen. Work and storage space abounds for easy food preparation. In addition, there is a small private office and a half bath on the first floor. A lovely master bedroom has a wood-burning fireplace, built-ins, and renovated bath. Three additional bedrooms and baths are located on the 2nd and 3rd floors. The Lower level has one bath and family room, also craft, laundry, and utility spaces A Separate covered terrace and one car garage are connected by additional terraces and old brick walkways. Property is on well and septic. Comcast for internet and TV. The 3.59 acres are in two lots, offering development potential.

Single Family

  • Price
  • $ 1,475,000
  • Lot Size
  • 3.61 Acres
  • Bedrooms
  • 4
  • Sqr Footage
  • 5,037
  • Full Bathrooms
  • 4
  • Year Built
  • 1949
  • Half Bathrooms
  • 1
  • City, Zip
  • Winchester
  • Taxes
  • 7142
  • County
  • Style
  • Georgian,Manor
  • Area
  • MLS#
  • VAWI114932
  • Zip
  • 22601
Listing Provided by: Washington Fine Properties, LLC



Acceptable Financing Conventional, Cash
Accessibility None
Appliances Cooktop, Cooktop - Down Draft, Dishwasher, Disposal, Dryer, Microwave, Oven - Single, Oven/Range - Electric, Refrigerator, Trash Compactor, Washer
Architectural Style Georgian, Manor
Association Y/N No
Carport Spaces 1
Condo/Coop Association Y/N No
Construction Materials Brick
Cool Fuel Electric
Cooling Heat Pump(s)
Electric 220 Volts
Facing Direction Northeast
Flooring Hardwood, Ceramic Tile, Stone
Garage Spaces 1.00
Garage Y/N Yes
Heating Forced Air
Historic Y/N No
Levels 4
New Construction No
Other Structures Above Grade, Below Grade
Ownership Fee Simple
Patio/Porch Features Patio(s), Terrace, Porch(es)
Possession Settlement
Price Per Sq Ft 334.39
Property Type Residential
Real Estate Owned Y/N No
Roof Slate
Senior Community Y/N No
Sewer On Site Septic
Structure Type Detached
Subdivision Name WINCHESTER CITY
Tax Annual Amount 7142.0
Tax Year 2020
Vacation Rental Y/N No
View City
Water Access Y/N No
Zoning LR

Interior Features

Above Grade Finished Area 4411
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Basement Partially Finished, Side Entrance, Other
Basement Y/N Yes
Bathrooms Count All Lower Levels 1
Bathrooms Count All Upper Levels 3
Bathrooms Count Lower Level 1 1.00
Bathrooms Count Main Level 1.00
Bathrooms Count Upper Level 1 2.00
Bathrooms Count Upper Level 2 1.00
Bathrooms Full All Lower Levels 1
Bathrooms Full All Upper Levels 3
Bathrooms Full Lower Level 1 1
Bathrooms Full Upper Level 1 2
Bathrooms Full Upper Level 2 1
Bathrooms Half Main Level 1
Bedrooms Count All Upper Levels 4
Bedrooms Count Upper Level 1 3
Bedrooms Count Upper Level 2 1
Below Grade Finished Area 626
Below Grade Finished Area Source Assessor
Below Grade Finished Area Unit Type Square Feet
Below Grade Unfin Area Units Square Feet
Below Grade Unfin Sqft 766
Below Grade Unfin Sqft Source Assessor
Central Air Y/N No
Fireplace Features Wood
Fireplace Y/N Yes
Full Baths 4
Half Baths 1
Heating Fuel Electric, Natural Gas
Heating Y/N Yes
Hot Water Electric
Laundry Type Basement
Living Area 5037
Room Type Living Room, Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Library, Foyer, Breakfast Room, Study, Laundry, Office, Solarium, Utility Room, Bathroom 2, Hobby Room
Total Baths 5
Total Bedrooms 4
Total Fireplaces 3
Window Features Double Hung, Screens, Wood Frame

Exterior Features

# Of Detached Carport Spaces 1
# Of Detached Garage Spaces 1
Door Features Six Panel
Fencing Privacy
Garage Features Garage - Rear Entry
Lot Features Backs to Trees, Subdivision Possible
Lot Size Acres 3.61
Lot Size Source Estimated
Lot Size Square Feet 157251.60
Navigable Water Y/N No
Pool Y/N No Pool
Roadresponsibility City/County
Spa No
Total Parking Spaces 6
Type of Parking Driveway, Detached Garage, Detached Carport
Water Oriented Y/N No
Water Source Well
Water View Y/N No
Waterfront Y/N No

Room Details

Bathroom 2 Upper 1 Flooring - Tile
Bedroom 2 Upper 1 Flooring - HardWood,Chair Rail
Bedroom 3 Upper 1 Flooring - HardWood
Bedroom 4 Upper 2 Flooring - Carpet
Breakfast Room Main Flooring - HardWood
Dining Room Main Fireplace - Wood Burning,Flooring - HardWood,Crown Molding
Family Room Lower 1
Foyer Main Flooring - HardWood,Crown Molding
Full Bath Upper 2 Flooring - Tile
Full Bath # 2 Lower 1
Hobby Room Lower 1
Kitchen Main Countertop(s) - Solid Surface,Crown Molding,Double Sink,Island,Kitchen - Country,Kitchen - Electric Cooking,Pantry
Laundry Lower 1
Library Main Flooring - HardWood,Built-Ins
Living Room Main Crown Molding,Chair Rail,Flooring - HardWood,Fireplace - Wood Burning
Office Main Flooring - HardWood
Primary Bathroom Upper 1
Primary Bedroom Upper 1 Flooring - HardWood,Built-Ins
Sitting Room Upper 2 Flooring - Carpet
Solarium Main Flooring - Other,Crown Molding
Study Lower 1
Utility Room Lower 1


  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Master On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator


Per Month

Based on the average sale price from the Moorestown, NJ office

  • Monthly Principal & interest $1,939
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 4.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.


Elementary School Unknown Elementary School
Middle School Unknown Middle School
High School Unknown High School

Price History

8/25/2020 Listed $1,475,000

Property vs Zip Code Average in 22601

AVG $400K
AVG $2,604
AVG 76
Year Built
AVG 1945


529 Jefferson Street Winchester, VA is a Single Family Home for sale at $1475000 with 5037 sqft and a lot size of 3.61 Acres Acre(s). 529 Jefferson Street Winchester has 4 bedrooms, 4 baths and was built in 1949. The property's zip code is 22601 which is in Winchester, VA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 4.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.