634 ft
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
687 WOODLAND AVENUE
Experience refined living in this stunning two-level brick residence, designed with an open-concept layout that seamlessly blends sophistication and comfort. The home features 4 spacious bedrooms, each with a private full bathroom.
The kitchen boasts granite countertops and elegant finishes, flowing
Living Area:
2489 Sqft.
|
3
Beds,
4
Baths
|
$564,900 |
423 HIGHLAND AVENUE
✨ Charming Winchester Home – Don’t Let This One Slip Away!
Welcome to this beautifully refreshed home in the heart of Winchester, offering exceptional value, versatility, and convenience. Thoughtfully updated throughout, this property is move-in ready while still leaving room to make it your
Living Area:
1300 Sqft.
|
3
Beds,
2
Baths
|
$295,000 |
|
3
Beds,
1
Bath
|
$285,000 | |
239 CHESTNUT STREET
239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home conveni
Living Area:
1176 Sqft.
|
2
Beds,
1
Bath
|
$299,000 |
212 FAIRFIELD DRIVE
Welcome to 212 Fairfield Drive, a sprawling, all-brick rancher offering an incredible amount of space and comfort in a highly sought-after Winchester location. This home is a commuter's dream, providing easy access to I-81 and other major commuter routes all while offering a peaceful, private retrea
Living Area:
5298 Sqft.
|
5
Beds,
4
Baths
|
$599,900 |
107 DALE CT
Welcome to Heritage Hills!
Tucked away on a quiet, private cul-de-sac, this property offers two lots—a .56-acre homesite plus an additional .41-acre corner lot (Tax ID: 54H 1 55)—for just under an acre of space to call your own.
This 4-bedroom, 2-bath home is filled with versatility and charm.
Living Area:
1608 Sqft.
|
4
Beds,
2
Baths
|
$399,000 |
20 W CLIFFORD STREET
This charming traditional brick home, nestled in the historic Winchester District, has a new minimalist European-inspired kitchen, a new full bath, and a new half bath. Featuring three spacious bedrooms, hardwood flooring and a welcoming dining area, perfect for gatherings. An entry-level bedroom a
Living Area:
1435 Sqft.
|
3
Beds,
2
Baths
|
$385,000 |
405 1/2 ELM STREET
Seller prefers to close with FD Title.
This adorable home sits on in a prime location very close to the downtown Winchester City! This renovated house features 3 bedrooms and 2 full bathrooms in a peaceful and vibrant setting. Property is vacant. You will find a renovated kitchen connected to the
Living Area:
1152 Sqft.
|
3
Beds,
2
Baths
|
$315,000 |
204 RIDGE ROAD
Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) on a full basement on the east side of Winchester featuring over 2100 sqft of finished living space that offers true hardwood flooring on the main level with 3 bedrooms and 1 full bath. Spacious living room tha
Living Area:
2131 Sqft.
|
3
Beds,
2
Baths
|
$414,999 |
17 E LEICESTER STREET
Classic 2100 square foot brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morn
Living Area:
2100 Sqft.
|
4
Beds,
2
Baths
|
$430,000 |
621 BUTLER AVENUE
Charming Rancher on Butler Avenue — This home is ready for its next owner! Nestled on a quiet street that ends in a cul-de-sac, you’ll enjoy peace and convenience of living on this east-side locations. Just steps to Virginia Avenue Elementary, parks, and Wesley Church, and only minutes to Histor
Living Area:
1803 Sqft.
|
4
Beds,
2
Baths
|
$300,000 |
113 WILLIAMSON ROAD
Charming All-Brick Ranch just minutes from in Prime Winchester Location. Beautifully maintained all-brick ranch just minutes from Jim Barnett Park, Winchester Country Club, shopping, and everyday amenities. This well built home blends timeless craftmanship with modern comfort and offers the ease of
Living Area:
1494 Sqft.
|
3
Beds,
2
Baths
|
$450,000 |
114 HEYFORD DRIVE
Say hello to your new home! This brand new, exquisite single family Home by Van Metre Homes in the highly sought-after SNOWDEN BRIDGE community in Stephenson, VA is ready for move in TODAY! The Scot 40-F2 floorplan is a master-crafted two-level residence boasting 3,641 of meticulously finished squar
Living Area:
3641 Sqft.
|
4
Beds,
5
Baths
|
$646,000 |
116 MAGPIE LANE
Step into the Sierra 39-F2 – Homesite 1037 at Hiatt Pointe (55+)—a two-car, front-load garage SINGLE FAMILY home with three bedrooms and three full bathrooms will be ready IMMEDIATELY. Designed for ease and everyday function, this factory-framed floorplan is as innovative as it stylish! Enter th
Living Area:
3200 Sqft.
|
3
Beds,
3
Baths
|
$650,434 |
132 AMHERST STREET
Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a true piece of Winchester's history. This is a Registered Historic Property that showcases original architectural details, high ceilings, ornate trim, and original wood floors that reflect the artistry of a bygo
Living Area:
3475 Sqft.
|
4
Beds,
4
Baths
|
$745,000 |
129 INDIANA
I am done! Large lot on private street with valley views and private. HW floors entire main floor and stairs, tile floors in all baths, BUILDER BONUS HARDWOOD TO INCLUDE BEDROOMS (no carpet in house), UPGRADED CABINETS, GRANITE COUNTERTOPS IN KITCHEN. New Colonial home. 3 bed, 2.5 full baths, open
Living Area:
1660 Sqft.
|
3
Beds,
3
Baths
|
$379,900 |
138 COUNTRY CLUB CIRCLE
Charming All-Brick Rancher with Pool Across from Winchester Country Club
This beautifully maintained 3-bedroom, 2-bath all-brick rancher offers classic charm and modern updates in one of Winchester’s most desirable east-side locations. Featuring a brand-new roof and new windows throughout, this h
Living Area:
2326 Sqft.
|
3
Beds,
2
Baths
|
$424,900 |
|
4
Beds,
2
Baths
|
$355,000 | |
227 MILLER STREET
Charming Downtown Winchester Home with Four Finished Levels. Welcome to 227 Miller Street, where timeless character and abundant living space come together in the heart of downtown Winchester. This inviting 4-bedroom, 4-bathroom home offers four fully finished levels that radiate warmth, comfort, an
Living Area:
3359 Sqft.
|
4
Beds,
4
Baths
|
$499,900 |
1125 CONWAY STREET
Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer!
Living Area:
870 Sqft.
|
2
Beds,
1
Bath
|
$289,900 |
713 ROSS ST
ALMOST COMPLETED!!!
BRAND NEW 3 BEDROOM, 2.5 BATH COLONIAL! NO HOA FEES!
Be the first to call this beautiful new construction yours. Conveniently located just outside the City of Winchester and close to shopping, this home offers an open layout designed for entertaining. The great room leads into th
Living Area:
1251 Sqft.
|
3
Beds,
3
Baths
|
$424,900 |
123 ETNAM STREET
Come see this beautiful home located just off of Rt 50 to the East side of Winchester, great location for commuters, 4br, 2.5 bath with lots of room and storage space. Fenced in backyard with nice 20x16 deck and 8x10 additional deck space off of that for great entertaining. Call agent for combo to
Living Area:
1904 Sqft.
|
4
Beds,
3
Baths
|
$400,000 |
709 ROSS ST
ALMOST COMPLETED!!!
BRAND NEW 3 BEDROOM, 2.5 BATH COLONIAL! NO HOA FEES!
Be the first to call this beautiful new construction yours. Conveniently located just outside the City of Winchester and close to shopping, this home offers an open layout designed for entertaining. The great room leads into th
Living Area:
1251 Sqft.
|
3
Beds,
3
Baths
|
$424,900 |
707 E CORK STREET
Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access t
Living Area:
1680 Sqft.
|
3
Beds,
3
Baths
|
$399,999 |
715 BERRYVILLE AVENUE
This renovated jewel on the east side of Winchester is ready for you! Enjoy the new modern kitchen, new tile bathrooms, updated HVAC and electrical, fresh paint, refinished floors, and more! Plus, this home is full of character you don't find in new homes. Look close! From unique windows to or
Living Area:
1426 Sqft.
|
3
Beds,
2
Baths
|
$349,900 |
525 E CORK STREET
Beautiful and affordable Gem in the middle of Winchester City.
Private, fully fenced yard with extra parking and storage.
Updated A/C and two year old roof.
Living Area:
858 Sqft.
|
2
Beds,
1
Bath
|
$299,900 |
513 VAN FOSSEN STREET
Welcome to 513 Van Fossen St, a beautifully updated 4-bedroom, 2.5-bathroom brick ranch conveniently located just minutes from downtown Winchester. Step inside to discover freshly refinished original red oak hardwood floors (locally sourced from Plumly Lumber) in a warm Golden Pecan finish (2025). T
Living Area:
2804 Sqft.
|
4
Beds,
3
Baths
|
$355,000 |
1400 VALLEY AVENUE
Versatile on Valley!
So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wa
Living Area:
3511 Sqft.
|
6
Beds,
4
Baths
|
$654,000 |
129 E CORK STREET
Welcome home to this charming 2-bedroom Craftsman-style home! Take a few steps up to this adorable downtown pad. Inside, you’ll find a warm and comfortable interior filled with character, including beautiful refinished hardwood floors, built-ins in the living room, and a built-in china cabinet in
Living Area:
935 Sqft.
|
2
Beds,
2
Baths
|
$297,000 |
122 CHERRY HILL CIRCLE
Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting
Living Area:
2014 Sqft.
|
5
Beds,
4
Baths
|
$435,000 |
939 WOODLAND AVENUE
Motivated sellers, Price Reduced!!! Need your Own Space? or you're looking to Downsize or Just Starting Out, Come Checkout this 1–2-bedroom 2 full bath home on 3 Levels Updated Kitchen with Stainless Steel Appliances, a Living room Dining room or Main level Bedroom with a Full bath attached., Wash
Living Area:
897 Sqft.
|
2
Beds,
2
Baths
|
$279,900 |
132 CAHILLE DRIVE
Prime Winchester location! 3-car garage and spacious driveway! This dream home is located minutes to commuter Routes 7, 50 and 81 and minutes from shopping, dining and entertainment in Old Town Winchester! Nestled in the prestigious Raven Pointe community, this exquisite Colonial home embodies lux
Living Area:
4167 Sqft.
|
4
Beds,
4
Baths
|
$679,900 |
501 NATIONAL AVENUE
National avenue is getting an upgrade and you will enjoy the renovations in this 4 square colonial with plenty of space, high ceilings, modernized baths and kitchen to the upgraded electrical, plumbing, and lighting. Parking for two in the rear gives you swift access to your back porch and straight
Living Area:
1820 Sqft.
|
4
Beds,
2
Baths
|
$359,999 |
106 W SOUTHWERK STREET
Charming 3 bedroom, 1.5 bath colonial just blocks from downtown Winchester! Enjoy a covered front porch perfect for relaxing and a spacious rear deck for entertaining. Inside, you’ll find inviting spaces with newer windows throughout. Conveniently located near shopping, restaurants, entertainment,
Living Area:
1144 Sqft.
|
3
Beds,
2
Baths
|
$299,500 |
127 KINROSS DRIVE
Welcome to 127 Kinross Dr in Winchester, VA! This spacious 5-bedroom, 3.5-bath home offers 3,494 sq. ft. of beautifully updated living space with modern upgrades throughout. Located in the well sought-after RAVEN WING Community due to its perfect location and commuter friendly access to all major hi
Living Area:
3494 Sqft.
|
5
Beds,
4
Baths
|
$620,000 |
20 E HART STREET
This is a completely restored Winchester classic within walking distance to the downtown area and Handley High school. Located at the end of street. Home improvements include new HVAC, plumbing, electric and appliances. Interior pictures will follow as soon as painting has been completed.
Living Area:
950 Sqft.
|
2
Beds,
1
Bath
|
$299,900 |
703 NATIONAL AVENUE
Fully renovated in 2025, this 3-bedroom, 2.5-bath home is ideally located within Winchester city limits—just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment, as well as Jim Barnett Park for outdoor recreation. Thoughtful updates and fresh landscaping enh
Living Area:
1976 Sqft.
|
3
Beds,
3
Baths
|
$479,900 |
118 E MONMOUTH STREET
Charming Remodeled Colonial in Historic Old Town Winchester
You’ll fall in love with this beautifully updated Colonial located in the heart of Winchester’s Historic District. Just steps from the Downtown Pedestrian Mall, Handley High School, and local shops and restaurants, this home blends time
Living Area:
1199 Sqft.
|
4
Beds,
2
Baths
|
$315,000 |
120 ARMSTRONG PLACE
Your opportunity to live next to the Golf course/Winchester Country Club in Fairway Estates!
Spacious brick rancher with a finished basement and a 2-car garage. 2 gas fireplaces and 1 wood burning.
Many updates to include: Roof 2021, HVAC's 2018, furnace serviced annually, water heater 2010, sump
Living Area:
3490 Sqft.
|
4
Beds,
3
Baths
|
$555,000 |
369 CHARLES STREET
This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level feature
Living Area:
1526 Sqft.
|
3
Beds,
2
Baths
|
$265,000 |
1004 S CAMERON STREET
PRICE REDUCED***Renovated Home in Winchester neighborhood.*** You’ll enter the house and find a spacious living room. As you continue walking, you’ll be led to the fully renovated kitchen. The kitchen features stainless steel appliances, including a new refrigerator, stove, microwave, dishwasher
Living Area:
1536 Sqft.
|
3
Beds,
3
Baths
|
$354,000 |
201 PARKWAY STREET
Freshly Renovated Charmer in Winchester!
Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners.
✨ Recent Updates Include:
Fresh interior paint throughout
Renovated
Living Area:
1627 Sqft.
|
4
Beds,
4
Baths
|
$474,500 |
1019 BERRYVILLE
1019 Berryville Avenue, Winchester, VA 22601 is a Fully-rented triplex located just minutes from Old Town Winchester and Shenandoah University. This approximately 3,000 sq. ft. property is configured as three fully independent residential and commercial units. All units have private entrances, full
Living Area:
3200 Sqft.
|
5
Beds,
3
Baths
|
$599,000 |
31 W WHITLOCK AVENUE
Charming Home Near Handley High School – Move-In Ready!
Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile
Living Area:
1416 Sqft.
|
3
Beds,
2
Baths
|
$396,500 |
110 CARTER PLACE
Contract fell through! Interest rates have gone down! Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natu
Living Area:
3116 Sqft.
|
5
Beds,
3
Baths
|
$494,970 |
226 TAGGART DRIVE
Welcome to 226 Taggart Drive – a sunlit Colonial in the heart of Winchester's sought-after Raven Pointe community.
This spacious 4-bedroom, 3.5 bath home offers over 4,200 square feet of beautifully finished living space across three levels, thoughtfully designed for comfort, functionality, and qu
Living Area:
4411 Sqft.
|
4
Beds,
4
Baths
|
$669,900 |
214 S BRADDOCK STREET
This property is currently zoned as fully commercial but has the potential to be changed to: Mixed Use or Fully Residential with proper city approval. Additional information from city located in documents. This home will need a Kitchen.
Situated in Downtown Winchester, 214 S Braddock is waiting for
Living Area:
2186 Sqft.
|
5
Beds,
2
Baths
|
$399,000 |
112 FAIRWAY DRIVE
New roof just installed!
This beautiful ranch-style home is located in a quiet cul-de-sac just minutes from downtown Winchester, Jim Barnett Park, and Shenandoah University. Ideal for commuters, with easy access to Route 7 and I-81.
The home features 3 bedrooms and 1 bathroom, with a full, partiall
Living Area:
1200 Sqft.
|
3
Beds,
1
Bath
|
$379,000 |
126 ARMSTRONG PLACE
All brick ranch home with 4 bedrooms close to town and a short walk to the golf course! Main level large living Room and dinning room, 2 bedrooms and 2 bathrooms, an eat in kitchen, has gleaming hardwood flooring. Lower Level large area for pool table 2 more bedrooms, 1 bathroom and a family room eq
Living Area:
1617 Sqft.
|
4
Beds,
3
Baths
|
$399,000 |
125 SPLIT RIDGE LANE
Very private community (2 five acre wooded lots) can not be seen from road. Close to town with wooded lots setting off of main road with private lane (TO BE PAVED UPON COMPLETION OF HOMES). This home boosts one level living with 3,100 sq. ft. of open floor plan with so many features others would ca
Living Area:
3100 Sqft.
|
3
Beds,
3
Baths
|
$929,900 |
113 SHOCKEY CIRCLE
Chance to build a home on maybe the last lot directly on Winchester Country Club golf course. This 1/2 acre lot is gently sloping (allowing for walk-out basement) with mature trees and open views to the 6th, 11th and 12th hole of WCC. Offered is the 3-car Fraser Model by Merrifield Homes. This op
Living Area:
3363 Sqft.
|
4
Beds,
3
Baths
|
$939,000 |