53 ft
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
316 W WHITLOCK AVENUE
Classic Stone Cape Cod Charm Meets Modern Luxury
This stunning, remodeled 1940s Stone Cape Cod offers the perfect blend of timeless architecture and contemporary comfort on one of Winchester's most coveted, quiet neighborhood streets. Enjoy the unique lifestyle of being walkable to vibrant downtown,
Living Area:
3278 Sqft.
|
3
Beds,
3
Baths
|
$679,900 |
400 HANDLEY AVENUE
Welcome to this beautifully preserved American brick Foursquare, an exceptional home that perfectly blends early 20th-century charm with modern updates. Nestled in one of Winchester’s most sought-after neighborhoods, this home is just two blocks from the annual Apple Blossom Parade , a short stro
Living Area:
2575 Sqft.
|
3
Beds,
3
Baths
|
$629,000 |
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 |
216 FAIRMONT AVENUE
Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spaciou
Living Area:
2177 Sqft.
|
3
Beds,
2
Baths
|
$550,000 |
807 BUTLER AVENUE
Welcome to this spacious split-foyer home ideally located near downtown Winchester! Offering 5 bedrooms and 3 full bathrooms, this property provides plenty of room for everyone. Cathedral ceilings in the main level living areas offer an open and airy layout. Recently refreshed with new flooring, f
Living Area:
1797 Sqft.
|
5
Beds,
3
Baths
|
$415,000 |
|
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 |
127 SHIRLEY STREET
Comfortable living at this split-foyer home located in the heart of the City of Winchester.
On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re jus
Living Area:
1780 Sqft.
|
4
Beds,
2
Baths
|
$365,000 |
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 |
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 |
315 W LEICESTER STREET
This charming home, beautifully renovated in 2018, offers a perfect blend of classic elegance and modern comfort. With four spacious bedrooms and four well-appointed bathrooms, this residence features stunning hardwood flooring throughout. The gourmet kitchen, complete with stainless steel appliance
Living Area:
3100 Sqft.
|
4
Beds,
4
Baths
|
$649,000 |
312 FOX DRIVE
Welcome to this charming all brick ranch style home nestled on a spacious 0.34-acre lot conveniently located in the City of Winchester. Built in 1959, this home has been well maintained and offers approximately 1,105 sq ft of living space with 3 bedrooms and 1 full bath, hardwood floors, a low maint
Living Area:
1105 Sqft.
|
3
Beds,
1
Bath
|
$375,000 |
27 JACKSON AVENUE
Great investor opportunity in the heart of Winchester! The LOWEST priced detached house within a 10-mile radius!! This 3-level home with a 2-car detached garage on a level treed lot is ideal for investors looking to fix and flip or fix and hold, with Shenandoah University only 3 miles away and Winch
Living Area:
1134 Sqft.
|
2
Beds,
1
Bath
|
$165,000 |
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 |
339 LANNY DRIVE
Right off of Amherst St. in sought after Whittier Acres, we are proud to present 339 Lanny Drive. This home is solid brick and sits on a fenced park-like .4 acre lot. Everything about this 2.716 square foot home will be appreciated and it is completely move-in ready. In 2024, just about everthing w
Living Area:
2444 Sqft.
|
3
Beds,
3
Baths
|
$515,900 |
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 |
509 MARION STREET
“Modern Magic on Marion” - Beautifully renovated 4 BR, 2.5 BA brick-front Colonial offering timeless curb appeal and classic comfort in an unbeatable Winchester location! Recent updates include fresh paint, new carpet, lighting, hardware, fixtures, basement renovations, refreshed landscaping, an
Living Area:
2691 Sqft.
|
4
Beds,
3
Baths
|
$549,900 |
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 |
501 JEFFERSON STREET
Welcome Home!
If you’ve been searching for an updated home in a prime location, this is it! This stunning 5BR/3BA property has been completely renovated from top to bottom—and it shows.
Step inside to an open floor plan where natural light fills the gorgeous kitchen, featuring quartz countertop
Living Area:
3420 Sqft.
|
5
Beds,
3
Baths
|
$659,000 |
553 HIGHLAND AVENUE
MOTIVATED SELLER -
OFFERING SUBSIDY TO BUYER FOR CLOSING COSTS OR MORTGAGE RATE BUY DOWN
One Way street = quiet
Gorgeous Rehab - you have to see it!
Secure Parking off the alley
Efficient HVAC mini splits installed
Washer and Dryer included
Living Area:
1362 Sqft.
|
3
Beds,
2
Baths
|
$334,000 |
341 WOOD AVENUE
Location, Location. Brick Rancher offers Walkout Basement, 4 Bedrooms, Two Full Baths. Hardwood Floors throughout. Front Entry Ceramic Tiled. Kitchen Luxury Vinyl Floor, New Dishwasher,Disposal, Refrigerator with Ice-maker( Not Hooked Up) and Electric Range. Basement Partially Finished with Brick F
Living Area:
1890 Sqft.
|
3
Beds,
2
Baths
|
$449,900 |
112 STAR FORT DRIVE
Unlock the Potential! 3BR/2BA Fixer-Upper in Winchester/Frederick County.
Nestled in a quiet Cul De Sac in Frederick County, this 3-bedroom, 2-bath home is bursting with potential and ready for a visionary buyer to bring it back to life.
Whether you're looking to renovate and resell or transform t
Living Area:
1072 Sqft.
|
3
Beds,
2
Baths
|
$300,000 |
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 |
608 GREEN STREET
Welcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 full bath. Hardwood floors, no carpet! Attached carport. Brand new shed in the backyard. Backs to common area. Deck off the back of the home. Newer windows. New Roof. Large kitchen. Laundry room off the kitchen. This home is
Living Area:
1040 Sqft.
|
3
Beds,
1
Bath
|
$284,999 |
700 WATSON AVENUE
Nestled in Orchard Terrace, this beautifully updated Colonial offers 4 bedrooms, 2 baths ideally located within Winchester city limits just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen has brand new granite countertops and stainless
Living Area:
1248 Sqft.
|
4
Beds,
2
Baths
|
$310,000 |
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 |
1332 RAMSEUR LANE
Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. Rich hardwood floors flow throughout the home. The primary bedroom includes a cozy fireplace perfect for relaxing evenings. Updated appliances, such as washer, d
Living Area:
2648 Sqft.
|
3
Beds,
2
Baths
|
$459,000 |
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 |
420 W CORK STREET
Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, di
Living Area:
1932 Sqft.
|
4
Beds,
2
Baths
|
$499,900 |
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 |
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 |
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 |
580 N BRADDOCK STREET
Now $450,000 — Motivated Sellers + Huge Monthly Savings with 2-1 Rate Buydown!
Step inside this beautifully restored 4-bedroom, 2.5-bath 1920s home and experience where historic charm meets modern luxury. Offering over 2,200 sq ft across three finished levels, 580 N Braddock delivers light, space
Living Area:
2200 Sqft.
|
4
Beds,
2
Baths
|
$400,000 |
121 N WASHINGTON STREET
A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet kitchen with brand new state of art appliances includes wine fridge, drawer style microwave, and pot filler. Formal living/dining room(s). Extras include den, office(s), nooks, and 3rd floor bonus room (perfec
Living Area:
3100 Sqft.
|
3
Beds,
3
Baths
|
$519,000 |
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 |
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 |
1005 PENNSYLVANIA AVENUE
Buyer Financing Has Fallen Through – Seller is Highly Motivated!!!!. A classic brick ranch in Winchester, VA, has three bedrooms and two full bathrooms. The basement includes a separate entrance, a laundry area, a full bathroom, and an additional bonus room. Recent updates include: finished base
Living Area:
2302 Sqft.
|
3
Beds,
2
Baths
|
$349,990 |
505 GREEN STREET
Charming 3-Level Split Home in the Heart of Winchester!
This split level home could be your forever home! Surrounded by parks, top-rated schools, and everyday amenities. Quick access to Route 7 and Interstate 81 commuting is breeze!
Upstairs, you’ll find three generously sized bedrooms and a f
Living Area:
1584 Sqft.
|
5
Beds,
2
Baths
|
$349,999 |
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 |
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 |
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 |