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Distinctive home on the historic register, Winchester walking tour, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester; restaurants, festivals, shopping! Gorgeous inside and out. Fully renovated, 4 levels with a two-story log cabin (the blue building) likely built with timber from Fort Loudoun) , gourmet emodeled kitchen with gas cooking, large pantry, eat-in space by the window. All three full and two half baths renovated. The red building offers a more formal living space with high ceilings in the large living room and dining room, and fireplaces. This was added onto the blue building in the late 1700's. Beautiful wide plank, old flooring exists throughout this section of the home. The turned staircase in the hallway leads to two upper levels, three bedrooms, and a huge bonus room/closet or flex space. The lower level is a finished basement with side entrance to the driveway with spacefor 4 cars. The blue side of the home consists of the kitchen addition behind the log cabin section wich has knotty pine built-in bookshelves and fireplace with pellet stove, an upper level room currently used as an office and a half bath. There is a n unfinished cellar with wonderful access to the front sidewalk - and crawl space under the kitchen. 7 fireplaces ( two with pellet stoves - the other 5 are "as-is") . 10' ceilings, gorgeous authentic wood paneling. Outside, you will be amazed -- the lot is deep affording privacy in the rear. The "dollhouse' shed with water and electric is a great workshop/storage area. Two porticos, planting beds, a koi pond, patio all add pleasure for outdoor living. Take your place in history as owner of this incredible home!

4 Beds ⋅ 4 Baths

Distinctive home on the historic register, Winchester walking tour, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester; restaurants, festivals, shopping! Gorgeous inside and out. Fully renovated, 4 levels with a two-story log cabin (the blue building) likely built with timber from Fort Loudoun) , gourmet emodeled kitchen with gas cooking, large pantry, eat-in space by the window. All three full and two half baths renovated. The red building offers a more formal living space with high ceilings in the large living room and dining room, and fireplaces. This was added onto the blue building in the late 1700's. Beautiful wide plank, old flooring exists throughout this section of the home. The turned staircase in the hallway leads to two upper levels, three bedrooms, and a huge bonus room/closet or flex space. The lower level is a finished basement with side entrance to the driveway with spacefor 4 cars. The blue side of the home consists of the kitchen addition behind the log cabin section wich has knotty pine built-in bookshelves and fireplace with pellet stove, an upper level room currently used as an office and a half bath. There is a n unfinished cellar with wonderful access to the front sidewalk - and crawl space under the kitchen. 7 fireplaces ( two with pellet stoves - the other 5 are "as-is") . 10' ceilings, gorgeous authentic wood paneling. Outside, you will be amazed -- the lot is deep affording privacy in the rear. The "dollhouse' shed with water and electric is a great workshop/storage area. Two porticos, planting beds, a koi pond, patio all add pleasure for outdoor living. Take your place in history as owner of this incredible home!

510 S Loudoun St, Winchester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Keller Williams Realty.

$670,000

If you've been waiting for a home that offers both character and modern convenience, this one deserves a close look. This all-brick, charming Cape Cod is located on a beautiful tree-lined street in the heart of Winchester with more space & versatility than meets the eye. Cross the threshold into the large, welcoming foyer and let your gaze take it all in...Large living room, large dining room, gorgeous staircase and center hall that draws you toward the beautifull, newly installed gourmet kitchen with butlers pantry. With 3 finished levels this home delivers space, comfort, and an unbeatable location in highly desired Downtown Winchester. Thoughtfully maintained and recently refreshed, this home features 4 bedrooms, 2 full baths, and a half bath, beautiful refinished wood floors and a newly remodeled kitchen that is sure to impress. Completed in September 2026, the kitchen dazzles with ample gorgeous cabinetry, extra-depth quartz counter tops, stunning center island with modern pendant lighting, pantry cabinets, stainless appliances, new flooring, built-in shelves, under cabinet lighting & butlers pantry. Additionally, the main level offers a primary bedroom/flex space with full bath. This home was originally built with a primary bedroom & bathroom on the main level. The present owners converted bedroom to use as a den. Use as you wish AND with little effort, the primary bedroom could easily be restored for those who desire "primary on the main". The main level is rounded out with mudroom with radiant heat in floors, dedicated office space and easy access to rear yard with patio. Upstairs, three additional bedrooms and another full bath provide plenty of room for family, guests, or a home office. The space on the upper level will take you by surprise with 2 rooms being quite large with charming built-in's and large closets. The walk-up basement adds valuable flexibility with large recreation room, a laundry area, workshop, and bonus room currently used as an office, plus a half bath. Outside, enjoy a detached one-car garage, fully fence rear yard, city sidewalks and a convenient location where so much is within easy reach. Walk to the Downtown Walking Mall, John Handley High School campus, restaurants, and more. Winchester Medical Center is just 2 miles away. The vibrant neighborhood offers a welcoming mix of households while remaining peaceful in the evenings. With the roof replaced in 2024 (includes garage), kitchen remodeled in 2026, upper wood floors refinished in 2026, and exterior trim freshly painted in 2026, this special home is ready for its next chapter. A place to with warmth, memories, and plenty of room to do so. All you have to do is move in.

4 Beds ⋅ 3 Baths

If you've been waiting for a home that offers both character and modern convenience, this one deserves a close look. This all-brick, charming Cape Cod is located on a beautiful tree-lined street in the heart of Winchester with more space & versatility than meets the eye. Cross the threshold into the large, welcoming foyer and let your gaze take it all in...Large living room, large dining room, gorgeous staircase and center hall that draws you toward the beautifull, newly installed gourmet kitchen with butlers pantry. With 3 finished levels this home delivers space, comfort, and an unbeatable location in highly desired Downtown Winchester. Thoughtfully maintained and recently refreshed, this home features 4 bedrooms, 2 full baths, and a half bath, beautiful refinished wood floors and a newly remodeled kitchen that is sure to impress. Completed in September 2026, the kitchen dazzles with ample gorgeous cabinetry, extra-depth quartz counter tops, stunning center island with modern pendant lighting, pantry cabinets, stainless appliances, new flooring, built-in shelves, under cabinet lighting & butlers pantry. Additionally, the main level offers a primary bedroom/flex space with full bath. This home was originally built with a primary bedroom & bathroom on the main level. The present owners converted bedroom to use as a den. Use as you wish AND with little effort, the primary bedroom could easily be restored for those who desire "primary on the main". The main level is rounded out with mudroom with radiant heat in floors, dedicated office space and easy access to rear yard with patio. Upstairs, three additional bedrooms and another full bath provide plenty of room for family, guests, or a home office. The space on the upper level will take you by surprise with 2 rooms being quite large with charming built-in's and large closets. The walk-up basement adds valuable flexibility with large recreation room, a laundry area, workshop, and bonus room currently used as an office, plus a half bath. Outside, enjoy a detached one-car garage, fully fence rear yard, city sidewalks and a convenient location where so much is within easy reach. Walk to the Downtown Walking Mall, John Handley High School campus, restaurants, and more. Winchester Medical Center is just 2 miles away. The vibrant neighborhood offers a welcoming mix of households while remaining peaceful in the evenings. With the roof replaced in 2024 (includes garage), kitchen remodeled in 2026, upper wood floors refinished in 2026, and exterior trim freshly painted in 2026, this special home is ready for its next chapter. A place to with warmth, memories, and plenty of room to do so. All you have to do is move in.

507 S Stewart St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Colony Realty.

$415,000

Life just got easier in this Beautiful Home. Here is a wonderfully maintained property offering 4 Bedrooms and 3 Full Baths with fresh neutral paint, a private lot, handy 1 car garage with sparkling stamped concrete driveway, sidewalk and 2 finished levels. There is so much room! Step into the sunny upper level to find a nice open floor plan. Kitchen, living and dining flow easily into one another and spill onto newly upgraded (in 2025) composite deck offering low-low maintenance. Private deck overlooks the fenced back yard. Surrounded by tall evergreens this deck truly offers privacy, peace and relaxation. Meaningful updates offer peace of mind - NEW roof installed in 2019 with 30 year architectural shingles, New furnace installed in 2021, New Heat Pump installed in 2021, New Water Heater installed in 2018. All the heavy lifting has been done. Just move in and enjoy. Lower level has oodles of space with a full bath. There is a dedicated bedroom space, laundry (washer purchased July/August 2025) and light filled family room. Access the garage and level backyard easily from lower level. Dishwasher is inoperable and conveys as is. Located in Winchester City this home is close to schools, shopping, commuter routes, and walking mall.

4 Beds ⋅ 3 Baths

Life just got easier in this Beautiful Home. Here is a wonderfully maintained property offering 4 Bedrooms and 3 Full Baths with fresh neutral paint, a private lot, handy 1 car garage with sparkling stamped concrete driveway, sidewalk and 2 finished levels. There is so much room! Step into the sunny upper level to find a nice open floor plan. Kitchen, living and dining flow easily into one another and spill onto newly upgraded (in 2025) composite deck offering low-low maintenance. Private deck overlooks the fenced back yard. Surrounded by tall evergreens this deck truly offers privacy, peace and relaxation. Meaningful updates offer peace of mind - NEW roof installed in 2019 with 30 year architectural shingles, New furnace installed in 2021, New Heat Pump installed in 2021, New Water Heater installed in 2018. All the heavy lifting has been done. Just move in and enjoy. Lower level has oodles of space with a full bath. There is a dedicated bedroom space, laundry (washer purchased July/August 2025) and light filled family room. Access the garage and level backyard easily from lower level. Dishwasher is inoperable and conveys as is. Located in Winchester City this home is close to schools, shopping, commuter routes, and walking mall.

290 Green St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Cuzzi Realty, Inc..

$268,000

**PRICE REDUCTION** This charming house in the heart of the City of Winchester has already been renovated, offering the perfect blend of classic charm and modern living. Featuring 2 cozy bedrooms and a full bathroom, the home is designed with comfort. Enjoy an updated kitchen and bathrooms, new appliances, and central A/C for a fresh, modern feel. The newly added front deck and patio provide great spaces to relax or entertain. Situated on a 0.17-acre lot with driveway parking, this home offers both indoor comfort and outdoor, Winchester location. Don’t miss your chance to make it yours!

2 Beds ⋅ 1 Baths

**PRICE REDUCTION** This charming house in the heart of the City of Winchester has already been renovated, offering the perfect blend of classic charm and modern living. Featuring 2 cozy bedrooms and a full bathroom, the home is designed with comfort. Enjoy an updated kitchen and bathrooms, new appliances, and central A/C for a fresh, modern feel. The newly added front deck and patio provide great spaces to relax or entertain. Situated on a 0.17-acre lot with driveway parking, this home offers both indoor comfort and outdoor, Winchester location. Don’t miss your chance to make it yours!

580 York Ave, Winchester

Listing courtesy of The Vasquez Group LLC. Contact:

Selling Office: First Decision Realty LLC.

$255,000

Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character.

4 Beds ⋅ 3 Baths

Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character.

719 National Ave, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

Selling Office: Real Broker, LLC.

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How much is your home worth?