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Awesome investment opportunity in the heart of Winchester! This 1910 duplex delivers timeless character with proven rental appeal. Tenants appreciate the generous living spaces across 2 bedrooms and 1 bath, while private backyards offer outdoor retreats that keep residents happy and renewing. Prime downtown location means easy access to shopping, dining, and entertainment. No HOA fees to cut into your returns. Two addresses, one smart investment.

9 & 11 E Pall Mall St, Winchester

Listing courtesy of Your Home Sold Guaranteed Realty - East LLC. Contact:

$399,044

Thoughtfully renovated home in the City, (although the backyard feels more like a private oasis) This one has all the renovations! Gorgeous Kitchen complete with Custom built in buffet, Quartz countertops, pantry cabinet and all the pretty features you are dreaming of! Brand new Appliances, recessed lighting, new lighting and plumbing fixtures throughout, LVP, vanities, Workshop/storage room. Enormous family room with custom built in cabinetry and a wood stove for the chilly winter nights. (current owners have not used) This lower level features a fully renovated full bath as well (maybe you use the whole space as your PRIMARY??!!) laundry room, and space for a play room/office. The true prize is beyond the double doors to the covered patio. This backyard will steel the show! Large shed for storage, deck for entertaining, grilling OR chilling! To the left of the home is an expansive field called Friendship Park (owned by the Friendship fire hall) This is what gives this home the feeling of privacy that's hard to find in the city.

3 Beds ⋅ 2 Baths

Thoughtfully renovated home in the City, (although the backyard feels more like a private oasis) This one has all the renovations! Gorgeous Kitchen complete with Custom built in buffet, Quartz countertops, pantry cabinet and all the pretty features you are dreaming of! Brand new Appliances, recessed lighting, new lighting and plumbing fixtures throughout, LVP, vanities, Workshop/storage room. Enormous family room with custom built in cabinetry and a wood stove for the chilly winter nights. (current owners have not used) This lower level features a fully renovated full bath as well (maybe you use the whole space as your PRIMARY??!!) laundry room, and space for a play room/office. The true prize is beyond the double doors to the covered patio. This backyard will steel the show! Large shed for storage, deck for entertaining, grilling OR chilling! To the left of the home is an expansive field called Friendship Park (owned by the Friendship fire hall) This is what gives this home the feeling of privacy that's hard to find in the city.

626 Bruce St, Winchester

Listing courtesy of Roberts Realty Group, LLC. Contact:

$399,900

Looking for a ranch-style home with plenty of potential and NO HOA? Offered for the first time by its original owner, this home offers convenient main-level living plus a finished bonus room above the garage, accessed by interior stairs located just off the kitchen. This additional finished space offers plenty of flexibility for a home office, hobby room, playroom, or whatever best fits your needs. Inside, you’ll find hardwood flooring in the foyer and living room, along with a gas fireplace that adds warmth and character to the main living space. The spacious primary suite features a walk-in closet, jetted tub, and an upgraded tiled walk-in shower with a built-in seat. A ramp at the front entrance provides easier access into the home. Outside, enjoy a nice, level yard along with an attached 2-car garage. The most recent updates that have already been completed are the HVAC system replaced in 2019 and a roof that was replaced approximately 6-7 years old. This home is being sold AS-IS and has been priced with its current condition in mind. While it could benefit from cosmetic updates such as fresh paint, new carpet, and some updating in the kitchen, the home can be enjoyed as it is today, allowing the next owner to make improvements and updates over time. It’s a great opportunity to move in, settle in, and make the home your own at your own pace. Convenient Winchester location close to restaurants, shopping and highways.

3 Beds ⋅ 2 Baths

Looking for a ranch-style home with plenty of potential and NO HOA? Offered for the first time by its original owner, this home offers convenient main-level living plus a finished bonus room above the garage, accessed by interior stairs located just off the kitchen. This additional finished space offers plenty of flexibility for a home office, hobby room, playroom, or whatever best fits your needs. Inside, you’ll find hardwood flooring in the foyer and living room, along with a gas fireplace that adds warmth and character to the main living space. The spacious primary suite features a walk-in closet, jetted tub, and an upgraded tiled walk-in shower with a built-in seat. A ramp at the front entrance provides easier access into the home. Outside, enjoy a nice, level yard along with an attached 2-car garage. The most recent updates that have already been completed are the HVAC system replaced in 2019 and a roof that was replaced approximately 6-7 years old. This home is being sold AS-IS and has been priced with its current condition in mind. While it could benefit from cosmetic updates such as fresh paint, new carpet, and some updating in the kitchen, the home can be enjoyed as it is today, allowing the next owner to make improvements and updates over time. It’s a great opportunity to move in, settle in, and make the home your own at your own pace. Convenient Winchester location close to restaurants, shopping and highways.

318 Stonehenge Rd, Winchester

Listing courtesy of NextHome Realty Select. Contact:

$439,900

Welcome home to this charming all-brick rancher, offering timeless appeal, beautiful hardwood floors throughout, and wonderful potential to make it your own! The inviting living room features a wood-burning fireplace, while the dining area provides a comfortable space for everyday meals and entertaining. The updated kitchen boasts granite countertops, and the remodeled bathroom adds a fresh, modern touch. Enjoy relaxing in the sun porch or entertaining outdoors on the stamped concrete patio, surrounded by gorgeous mature trees in the backyard. Replacement windows and architectural shingles, approximately nine years old, provide additional peace of mind. The walk-up attic offers exciting possibilities for additional living space, while the unfinished basement features a rough-in for a future bathroom and the opportunity to expand your finished living area. With three bedrooms, classic brick construction, and room to grow, this home is full of possibilities. Don't miss the opportunity to make it yours!

3 Beds ⋅ 1 Baths

Welcome home to this charming all-brick rancher, offering timeless appeal, beautiful hardwood floors throughout, and wonderful potential to make it your own! The inviting living room features a wood-burning fireplace, while the dining area provides a comfortable space for everyday meals and entertaining. The updated kitchen boasts granite countertops, and the remodeled bathroom adds a fresh, modern touch. Enjoy relaxing in the sun porch or entertaining outdoors on the stamped concrete patio, surrounded by gorgeous mature trees in the backyard. Replacement windows and architectural shingles, approximately nine years old, provide additional peace of mind. The walk-up attic offers exciting possibilities for additional living space, while the unfinished basement features a rough-in for a future bathroom and the opportunity to expand your finished living area. With three bedrooms, classic brick construction, and room to grow, this home is full of possibilities. Don't miss the opportunity to make it yours!

411 Mosby St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

$399,000

Welcome to this charming brick home located in the heart of Winchester! Filled with historic character, this home features beautiful hardwood floors throughout, spacious living areas, and oversized bedrooms. Enjoy relaxing on the covered front porch or entertaining on the covered back porch overlooking the large backyard. The home's timeless charm and generous room sizes offer a wonderful opportunity to make it your own. Location is a highlight! Situated right next to Ruth Jackson Memorial Park, within walking distance of Patsy Cline Memorial Park, and directly across the street from the Green Circle Trail, you'll have easy access to walking, biking, and outdoor recreation. Plus, you're just a short stroll from local shops, restaurants, Shenandoah University, and all that downtown Winchester has to offer. Historic charm, spacious living, and a fantastic location make this home a wonderful opportunity!

4 Beds ⋅ 2 Baths

Welcome to this charming brick home located in the heart of Winchester! Filled with historic character, this home features beautiful hardwood floors throughout, spacious living areas, and oversized bedrooms. Enjoy relaxing on the covered front porch or entertaining on the covered back porch overlooking the large backyard. The home's timeless charm and generous room sizes offer a wonderful opportunity to make it your own. Location is a highlight! Situated right next to Ruth Jackson Memorial Park, within walking distance of Patsy Cline Memorial Park, and directly across the street from the Green Circle Trail, you'll have easy access to walking, biking, and outdoor recreation. Plus, you're just a short stroll from local shops, restaurants, Shenandoah University, and all that downtown Winchester has to offer. Historic charm, spacious living, and a fantastic location make this home a wonderful opportunity!

317 S Kent St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$673,000

Quiet Brick Cape Cod in the heart of Winchester, VA with over 4 thousand sqft and 6 bedrooms, there is plenty of space for everyone - growing family or combining house holds. 3 fireplaces - colonial style gas in the living room, brick gas in the kitchen, and brick wood burning in the basement. A concrete in-ground pool with built-in entry stairs in the 3 ft shallow end and a built-in sitting shelf in the 9ft deep end. A jumping stone makes for a interesting natural feature that just blends into the landscaping of the backyard oasis. The laundry room is ready to be converted into a kitchenette to further help with combined households. Even with all the finished space in the basement there is still amble storage space. So many ways to enjoy this home: swinging on the front porch watching the world go by, cooking holiday meals in the enormous kitchen, sitting by the fire reading a book, hours swimming in the pool with patio cook-outs. All of this is minutes away from all the necessities of life: shopping, hospital, schools, downtown dining and festivals, museums, trails. As quiet as it is, it is hard to believe you really are in the heart of Winchester. Between the spacious rooms, mid-century craftmanship, and numerous features, you can make this your home for generations to fully enjoy all of what Winchester has to offer.

6 Beds ⋅ 4 Baths

Quiet Brick Cape Cod in the heart of Winchester, VA with over 4 thousand sqft and 6 bedrooms, there is plenty of space for everyone - growing family or combining house holds. 3 fireplaces - colonial style gas in the living room, brick gas in the kitchen, and brick wood burning in the basement. A concrete in-ground pool with built-in entry stairs in the 3 ft shallow end and a built-in sitting shelf in the 9ft deep end. A jumping stone makes for a interesting natural feature that just blends into the landscaping of the backyard oasis. The laundry room is ready to be converted into a kitchenette to further help with combined households. Even with all the finished space in the basement there is still amble storage space. So many ways to enjoy this home: swinging on the front porch watching the world go by, cooking holiday meals in the enormous kitchen, sitting by the fire reading a book, hours swimming in the pool with patio cook-outs. All of this is minutes away from all the necessities of life: shopping, hospital, schools, downtown dining and festivals, museums, trails. As quiet as it is, it is hard to believe you really are in the heart of Winchester. Between the spacious rooms, mid-century craftmanship, and numerous features, you can make this your home for generations to fully enjoy all of what Winchester has to offer.

718 Academy Cir, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$699,000

432 North Loudoun Street sits a half block up from the historic fort and 2 blocks from the Winchester Mall. This completely redeveloped 1915 Craftsman style house in Winchester’s emerging historic district masterfully combines modern purpose with a classic feel using a sustainable redevelopment design. It is a custom home within a historical exterior, offering all the experiences of new construction. This is a high-quality residence for building your life with its 4 bedrooms, 2 ½ bath, dual street access, including a full fenced-in yard with landscaped patio, hot tub, and 10x8 shed. The floor plan is built around original hand-scraped hardwoods, handcrafted Craftsman style door moldings, an abundance of windows, period staircases, and a stunning new main bedroom/kitchen/family room addition to name a few of the fine features. Upstairs has the owner suite with walk-in closet and full bathroom; additional features include two bedrooms, a wired office, laundry center, and full bath. Presenting wide-ranging features from the mahogany front porch to the custom-built basement staircase to the new addition owner’s suite 432 Loudoun showcases quality is a requirement not a luxury.

4 Beds ⋅ 3 Baths

432 North Loudoun Street sits a half block up from the historic fort and 2 blocks from the Winchester Mall. This completely redeveloped 1915 Craftsman style house in Winchester’s emerging historic district masterfully combines modern purpose with a classic feel using a sustainable redevelopment design. It is a custom home within a historical exterior, offering all the experiences of new construction. This is a high-quality residence for building your life with its 4 bedrooms, 2 ½ bath, dual street access, including a full fenced-in yard with landscaped patio, hot tub, and 10x8 shed. The floor plan is built around original hand-scraped hardwoods, handcrafted Craftsman style door moldings, an abundance of windows, period staircases, and a stunning new main bedroom/kitchen/family room addition to name a few of the fine features. Upstairs has the owner suite with walk-in closet and full bathroom; additional features include two bedrooms, a wired office, laundry center, and full bath. Presenting wide-ranging features from the mahogany front porch to the custom-built basement staircase to the new addition owner’s suite 432 Loudoun showcases quality is a requirement not a luxury.

432 N Loudoun St, Winchester

Listing courtesy of The Greene Realty Group. Contact:

$229,000

Affordable homeowership opportunity in city limits. This town home has been cared for by owner for 35 years. Just needs some TLC to make it your own style. Living & dining with hardwood flooring. Bright kitchen with pantry and all appliances to convey. Plenty of storage with coat closet, 2 utility closets & hall closet. Laundry with shelving and space for freezer or more cabinety. Both bedroooms have double wide closets with double doors. 2 Liquid solar walls are an 80's system of plastic wall panels with internal liquid heated by sun to heat room. Owner has maintained regular servicing for gas heat & central AC. Private back yard with fencing . Not a thoroughfare street. Located convenient to dining, schools, retail, parks & rec, Green Circle Trail, just minutes to Shenandoah Universiry, the medical center, Apple Blossom Mall & Downtown Loudoun Street Walking Mall & commute routes 7, 81 and 37. Call today for a private tour

2 Beds ⋅ 2 Baths

Affordable homeowership opportunity in city limits. This town home has been cared for by owner for 35 years. Just needs some TLC to make it your own style. Living & dining with hardwood flooring. Bright kitchen with pantry and all appliances to convey. Plenty of storage with coat closet, 2 utility closets & hall closet. Laundry with shelving and space for freezer or more cabinety. Both bedroooms have double wide closets with double doors. 2 Liquid solar walls are an 80's system of plastic wall panels with internal liquid heated by sun to heat room. Owner has maintained regular servicing for gas heat & central AC. Private back yard with fencing . Not a thoroughfare street. Located convenient to dining, schools, retail, parks & rec, Green Circle Trail, just minutes to Shenandoah Universiry, the medical center, Apple Blossom Mall & Downtown Loudoun Street Walking Mall & commute routes 7, 81 and 37. Call today for a private tour

23 Jigsaw Pl, Winchester

Listing courtesy of Coldwell Banker Elite. Contact:

$559,000

Welcome Home! This 4 Bedroom Colonial has gleaming hardwood floors throughout both levels. With traditional formal living & dining rooms with beautiful trim mouldings. Large 27x13' family room that features tray ceiling & fireplace w/mantel, is open to kichen for family togetherness & entertaining. Your Kitchen with granite counters, glass tile backspalsh, staineless appliances, pendant lighting over breakfast bar and 2 pantries. Owners Suite with ceiling fan, walk in closet and private bath w/beautiful glass tile shower & dual sinks. All 3 baths with ceramic tile flooring. You'll enjoy the east facing sun room for morning coffee or relaxing at end of day. Outdoor living amenities - a 21x16 ft patio, 27 linear ft covered front porch and fully fenced back yard with 2 gates. Vinyl clad fence is low maintenance. Plenty of storage - a 12x16 shed, walk up attic, 2 car garage with storage closet and a half attic, double door coat closet, double door linen closet & an extra walk in closet. Laundry on upper bedroom level is efficient. Gas heat & central AC. Fresh paint. Energy efficient windows, storm doors, palladian window, french doors, 6 panel doors. Central Vacuum. Garage heater and 240V service . Owners have completed items noted on their pre-listing home inspection - move in ready. Walk to adjacent Kernstown Battlefield, neighborhood is located conventient to dining, schools, retail, parks & rec, Green Circle Trail, bike path, just minutes to Shenandoah Universiry, medical center, Apple Blossom Mall & Downtown Loudoun Street Walking Mall & commute routes 7, 81 amd 37. Call today for a private tour appointment of this beautiful home.

4 Beds ⋅ 3 Baths

Welcome Home! This 4 Bedroom Colonial has gleaming hardwood floors throughout both levels. With traditional formal living & dining rooms with beautiful trim mouldings. Large 27x13' family room that features tray ceiling & fireplace w/mantel, is open to kichen for family togetherness & entertaining. Your Kitchen with granite counters, glass tile backspalsh, staineless appliances, pendant lighting over breakfast bar and 2 pantries. Owners Suite with ceiling fan, walk in closet and private bath w/beautiful glass tile shower & dual sinks. All 3 baths with ceramic tile flooring. You'll enjoy the east facing sun room for morning coffee or relaxing at end of day. Outdoor living amenities - a 21x16 ft patio, 27 linear ft covered front porch and fully fenced back yard with 2 gates. Vinyl clad fence is low maintenance. Plenty of storage - a 12x16 shed, walk up attic, 2 car garage with storage closet and a half attic, double door coat closet, double door linen closet & an extra walk in closet. Laundry on upper bedroom level is efficient. Gas heat & central AC. Fresh paint. Energy efficient windows, storm doors, palladian window, french doors, 6 panel doors. Central Vacuum. Garage heater and 240V service . Owners have completed items noted on their pre-listing home inspection - move in ready. Walk to adjacent Kernstown Battlefield, neighborhood is located conventient to dining, schools, retail, parks & rec, Green Circle Trail, bike path, just minutes to Shenandoah Universiry, medical center, Apple Blossom Mall & Downtown Loudoun Street Walking Mall & commute routes 7, 81 amd 37. Call today for a private tour appointment of this beautiful home.

2820 Saratoga Dr, Winchester

Listing courtesy of Coldwell Banker Elite. Contact:

$850,000

Exceptional Winchester living with TWO primary suites, an incredible covered outdoor living space, and a private in-ground pool! This beautifully appointed home offers an impressive combination of space, comfort, and entertainment options, with thoughtful and detailed features throughout, that make it truly special. This gorgeous all brick Colonial home features an all brick porch which spans the home's full width, providing so many options for decorating, seating, etc. The house front is set off by classic columns and a leaded glass door. The main level, welcomes you with a formal dining room, spacious enough to accommodate a full dining set and seating for eight. Holiday gatherings and dinner parties will be a breeze! A comfortable family room provides additional everyday living space, while the game room takes entertaining to the next level with a wet bar and gas fireplace. At the heart of the home is the Gourmet Kitchen featuring double ovens, an electric cooktop, built in microwave and double ovens. For added convenience there is a trash compactor! Completing the kitchen is the center island with seating. Truly a space to make memories. One of the home's most inviting features is the expansive covered deck. It's very spacious, yet also cozy. Complete with its own gas fireplace and a gas grill connected directly to the home's gas line, this outdoor living space is designed for year-round enjoyment. Blinds provide added privacy, while the elevated deck overlooks the large in-ground pool, creating an exceptional setting for summer gatherings, relaxing evenings, and entertaining family and friends. The upper level offers three bedrooms, including a spacious primary suite featuring a beautiful soaking tub, separate standing shower, and dual-sink vanity. The large walk-in closet is a bonus! Two secondary bedrooms share a well-appointed hall bath. Gorgeous terrazzo tile flooring brings in an elegant touch to the upper-level hallway. The second primary suite provides exceptional flexibility for guests, multigenerational living, or those seeking a private retreat. In the lower level you will enjoy an abundance of additional living, entertaining, storage, and parking space. Two separate garage areas provide parking for up to three vehicles, while a full bath and recreation room with wet bar make this level incredibly versatile. Copious cabinetry in the garage area provides tremendous storage, while the mechanical area offers additional functional space. Recent improvements include new windows and Leaf Filter gutter guards, both installed within the last two years. From the multiple living and entertaining spaces to the incredible covered deck, pool, fireplaces, wet bars, and TWO primary suites, this is far more than just a house—it is a home designed for living, entertaining, and making memories. A truly exceptional Winchester property offering a rare combination of indoor and outdoor amenities. Don't miss the opportunity to make 637 Treys Drive your next home!

4 Beds ⋅ 5 Baths

Exceptional Winchester living with TWO primary suites, an incredible covered outdoor living space, and a private in-ground pool! This beautifully appointed home offers an impressive combination of space, comfort, and entertainment options, with thoughtful and detailed features throughout, that make it truly special. This gorgeous all brick Colonial home features an all brick porch which spans the home's full width, providing so many options for decorating, seating, etc. The house front is set off by classic columns and a leaded glass door. The main level, welcomes you with a formal dining room, spacious enough to accommodate a full dining set and seating for eight. Holiday gatherings and dinner parties will be a breeze! A comfortable family room provides additional everyday living space, while the game room takes entertaining to the next level with a wet bar and gas fireplace. At the heart of the home is the Gourmet Kitchen featuring double ovens, an electric cooktop, built in microwave and double ovens. For added convenience there is a trash compactor! Completing the kitchen is the center island with seating. Truly a space to make memories. One of the home's most inviting features is the expansive covered deck. It's very spacious, yet also cozy. Complete with its own gas fireplace and a gas grill connected directly to the home's gas line, this outdoor living space is designed for year-round enjoyment. Blinds provide added privacy, while the elevated deck overlooks the large in-ground pool, creating an exceptional setting for summer gatherings, relaxing evenings, and entertaining family and friends. The upper level offers three bedrooms, including a spacious primary suite featuring a beautiful soaking tub, separate standing shower, and dual-sink vanity. The large walk-in closet is a bonus! Two secondary bedrooms share a well-appointed hall bath. Gorgeous terrazzo tile flooring brings in an elegant touch to the upper-level hallway. The second primary suite provides exceptional flexibility for guests, multigenerational living, or those seeking a private retreat. In the lower level you will enjoy an abundance of additional living, entertaining, storage, and parking space. Two separate garage areas provide parking for up to three vehicles, while a full bath and recreation room with wet bar make this level incredibly versatile. Copious cabinetry in the garage area provides tremendous storage, while the mechanical area offers additional functional space. Recent improvements include new windows and Leaf Filter gutter guards, both installed within the last two years. From the multiple living and entertaining spaces to the incredible covered deck, pool, fireplaces, wet bars, and TWO primary suites, this is far more than just a house—it is a home designed for living, entertaining, and making memories. A truly exceptional Winchester property offering a rare combination of indoor and outdoor amenities. Don't miss the opportunity to make 637 Treys Drive your next home!

637 Treys Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$535,000

Built in 2023 and offering the feel of new construction without the new construction price tag, this spacious three-level home in the WEA-VILLA community has so much to offer, including NO HOA! With five true bedrooms, three full bathrooms, and an incredibly flexible layout, there is room here for everyone. The main level features a fifth bedroom with a full bath nearby, making it perfect for guests, multigenerational living, a private home office, or anyone who prefers main-level accommodations. Upstairs, you’ll find four additional bedrooms plus a generous loft area that can easily become a playroom, second living space, office, homework area, or whatever best fits your lifestyle. Downstairs, the unfinished basement provides even more space and tons of potential for future living areas, a home gym, recreation room, workshop, or storage. Outside, the upgrades continue with a brand-new fenced backyard that is ready for pets, playtime, and entertaining, along with a brand-new storage shed for all of your outdoor gear and equipment. The .35-acre lot gives you plenty of usable outdoor space without feeling overwhelming. Built just a few years ago, this home gives you the modern finishes, efficiency, and low-maintenance appeal of a new build while already having some of the expensive extras taken care of, including the fence and shed. The location is exceptionally convenient, with easy access to I-81, Route 7, and Route 50, making commuting and everyday errands a breeze. Shopping, dining, schools, parks, and local amenities are all within easy reach. If you’ve been considering new construction but want more space, added upgrades, no HOA, and a better value, this one deserves a look. Five bedrooms, three full baths, a loft, an unfinished basement with room to grow, a fenced yard, and a new shed - this house has room for just about everything!

5 Beds ⋅ 3 Baths

Built in 2023 and offering the feel of new construction without the new construction price tag, this spacious three-level home in the WEA-VILLA community has so much to offer, including NO HOA! With five true bedrooms, three full bathrooms, and an incredibly flexible layout, there is room here for everyone. The main level features a fifth bedroom with a full bath nearby, making it perfect for guests, multigenerational living, a private home office, or anyone who prefers main-level accommodations. Upstairs, you’ll find four additional bedrooms plus a generous loft area that can easily become a playroom, second living space, office, homework area, or whatever best fits your lifestyle. Downstairs, the unfinished basement provides even more space and tons of potential for future living areas, a home gym, recreation room, workshop, or storage. Outside, the upgrades continue with a brand-new fenced backyard that is ready for pets, playtime, and entertaining, along with a brand-new storage shed for all of your outdoor gear and equipment. The .35-acre lot gives you plenty of usable outdoor space without feeling overwhelming. Built just a few years ago, this home gives you the modern finishes, efficiency, and low-maintenance appeal of a new build while already having some of the expensive extras taken care of, including the fence and shed. The location is exceptionally convenient, with easy access to I-81, Route 7, and Route 50, making commuting and everyday errands a breeze. Shopping, dining, schools, parks, and local amenities are all within easy reach. If you’ve been considering new construction but want more space, added upgrades, no HOA, and a better value, this one deserves a look. Five bedrooms, three full baths, a loft, an unfinished basement with room to grow, a fenced yard, and a new shed - this house has room for just about everything!

306 Longview Ave, Winchester

Listing courtesy of Charis Realty Group. Contact:

$255,000

329 Fairview Ave is a two-story Winchester single-family home with a bright, window-lined sunroom and a classic covered front porch. Plank flooring runs through the main living areas, where soft neutral walls and generous windows keep each room filled with natural light. The kitchen pairs crisp white cabinetry with ample counter space, a dishwasher, and a built-in microwave above the range. Carpeted bedrooms provide comfortable retreats, and the bathrooms include a tub with a dark tile surround and a wood vanity set against black-and-white mosaic floor tile. Out back, a grassy yard leaves room to garden or unwind outdoors.

3 Beds ⋅ 2 Baths

329 Fairview Ave is a two-story Winchester single-family home with a bright, window-lined sunroom and a classic covered front porch. Plank flooring runs through the main living areas, where soft neutral walls and generous windows keep each room filled with natural light. The kitchen pairs crisp white cabinetry with ample counter space, a dishwasher, and a built-in microwave above the range. Carpeted bedrooms provide comfortable retreats, and the bathrooms include a tub with a dark tile surround and a wood vanity set against black-and-white mosaic floor tile. Out back, a grassy yard leaves room to garden or unwind outdoors.

329 Fairview Ave, Winchester

Listing courtesy of Open Door Brokerage, LLC. Contact:

$749,000

Downtown living at its finest! Welcome to 220 Amherst Street, a stunning brick residence nestled in Winchester’s prestigious historic district. This home blends timeless architectural charm with an unbeatable location just steps from downtown dining, boutique shopping, top-rated schools, parks, and the medical center. Classic historic character greets you at the curb, framed by a wrought-iron fenced front yard and a classic brick driveway leading to a rare detached garage featuring a brand-new roof. Step inside to discover gleaming hardwood floors, crisp wainscoting, and detailed crown molding throughout the main living areas. The main level offers a flexible layout that includes a full bathroom, a formal living room anchored by a wood-burning fireplace, an adjoining sitting room, and an elegant formal dining room. The modern kitchen features a sleek subway tile backsplash, stainless steel appliances, a large walk-in pantry, and a cozy breakfast area with built-in seating. Sunlit wooden stairs under overhead skylights lead to the light-filled second level. The spacious primary suite serves as a private retreat with its magnificently renovated ensuite bath—complete with double-sinks, upgraded countertops, a separate tub and walk-in shower, subway tile accents, and custom mosaic flooring. Two additional generous bedrooms and another recently updated full bath share this floor alongside a versatile updated sunroom. Fitted with wall-to-wall windows and its own newer mini-split system for climate control, the sunroom opens directly onto an open deck perfect for catching the morning sun. Up on the top floor, a finished attic provides versatile living space with built-ins and fresh carpet, offering flexible space ideal for a home office, playroom, or media center. The extensive living space continues into the finished basement with durable tile floors and an awesome recreation room highlighted by a second wood-burning fireplace, built-ins, and ample closet space. The basement also includes a cedar-lined closet, dedicated laundry facilities, another full bath, and abundant extra storage space. Outdoors, the backyard sanctuary is fully enclosed with a newer privacy fence and thoughtfully equipped for outdoor leisure, boasting a screened-in porch, raised garden beds, a charming trellis pergola with a dedicated play area, and unmatched privacy right in the heart of town. Complete with a new HVAC system, this move-in-ready historic gem delivers the ideal balance of classic elegance and modern comfort.

4 Beds ⋅ 4 Baths

Downtown living at its finest! Welcome to 220 Amherst Street, a stunning brick residence nestled in Winchester’s prestigious historic district. This home blends timeless architectural charm with an unbeatable location just steps from downtown dining, boutique shopping, top-rated schools, parks, and the medical center. Classic historic character greets you at the curb, framed by a wrought-iron fenced front yard and a classic brick driveway leading to a rare detached garage featuring a brand-new roof. Step inside to discover gleaming hardwood floors, crisp wainscoting, and detailed crown molding throughout the main living areas. The main level offers a flexible layout that includes a full bathroom, a formal living room anchored by a wood-burning fireplace, an adjoining sitting room, and an elegant formal dining room. The modern kitchen features a sleek subway tile backsplash, stainless steel appliances, a large walk-in pantry, and a cozy breakfast area with built-in seating. Sunlit wooden stairs under overhead skylights lead to the light-filled second level. The spacious primary suite serves as a private retreat with its magnificently renovated ensuite bath—complete with double-sinks, upgraded countertops, a separate tub and walk-in shower, subway tile accents, and custom mosaic flooring. Two additional generous bedrooms and another recently updated full bath share this floor alongside a versatile updated sunroom. Fitted with wall-to-wall windows and its own newer mini-split system for climate control, the sunroom opens directly onto an open deck perfect for catching the morning sun. Up on the top floor, a finished attic provides versatile living space with built-ins and fresh carpet, offering flexible space ideal for a home office, playroom, or media center. The extensive living space continues into the finished basement with durable tile floors and an awesome recreation room highlighted by a second wood-burning fireplace, built-ins, and ample closet space. The basement also includes a cedar-lined closet, dedicated laundry facilities, another full bath, and abundant extra storage space. Outdoors, the backyard sanctuary is fully enclosed with a newer privacy fence and thoughtfully equipped for outdoor leisure, boasting a screened-in porch, raised garden beds, a charming trellis pergola with a dedicated play area, and unmatched privacy right in the heart of town. Complete with a new HVAC system, this move-in-ready historic gem delivers the ideal balance of classic elegance and modern comfort.

220 Amherst St, Winchester

Listing courtesy of Colony Realty. Contact:

$289,900

SINGLE-FAMILY LIVING IN WINCHESTER WITHOUT THE BIG PRICE TAG! Welcome to 322 Highland Ave, an opportunity to get the space of a 4-bedroom detached home at an approachable price point. With four bedrooms and 2.5 baths, there’s room to spread out, work from home, create a guest room, or simply enjoy the flexibility that extra bedrooms provide. This home is a great option for buyers who have been searching for more space without stretching into the price range of many larger single-family homes in the area. More house. More bedrooms. More possibilities. Come see the value for yourself!

4 Beds ⋅ 3 Baths

SINGLE-FAMILY LIVING IN WINCHESTER WITHOUT THE BIG PRICE TAG! Welcome to 322 Highland Ave, an opportunity to get the space of a 4-bedroom detached home at an approachable price point. With four bedrooms and 2.5 baths, there’s room to spread out, work from home, create a guest room, or simply enjoy the flexibility that extra bedrooms provide. This home is a great option for buyers who have been searching for more space without stretching into the price range of many larger single-family homes in the area. More house. More bedrooms. More possibilities. Come see the value for yourself!

322 Highland Ave, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

$335,000

Well maintained three story, all brick townhome located in the City of Winchester. This home is on a quiet street and conveniently located close to shopping and restaurants. There are hardwood floors throughout the main level consisting of the kitchen/dining area, living room, and half bath. There are two nice sized bedrooms and one full bath on the upper level, along with separate laundry. (Maytag washer and dryer purchased in 2024 convey with property) The lower level has a finished living space with electric baseboard heat and could be comfortably used as a family room, office, or additional bedroom. Directly off the finished lower level are a one car garage and storage area. (The new freezer located in garage also conveys) This townhome comes with plenty of parking, whether it is street parking in front, a private concrete driveway in the rear, or the rear loading garage. (Townhome is freshly painted throughout.) Townhomes in this subdivision rarely come to market, so don't wait!

2 Beds ⋅ 2 Baths

Well maintained three story, all brick townhome located in the City of Winchester. This home is on a quiet street and conveniently located close to shopping and restaurants. There are hardwood floors throughout the main level consisting of the kitchen/dining area, living room, and half bath. There are two nice sized bedrooms and one full bath on the upper level, along with separate laundry. (Maytag washer and dryer purchased in 2024 convey with property) The lower level has a finished living space with electric baseboard heat and could be comfortably used as a family room, office, or additional bedroom. Directly off the finished lower level are a one car garage and storage area. (The new freezer located in garage also conveys) This townhome comes with plenty of parking, whether it is street parking in front, a private concrete driveway in the rear, or the rear loading garage. (Townhome is freshly painted throughout.) Townhomes in this subdivision rarely come to market, so don't wait!

2660 Daniel Ter, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$299,900

Charming, cheerful, and filled with natural light, this inviting 3-bedroom, 1-bath rancher makes a delightful first impression. Fresh yellow siding, mature trees, blooming hydrangeas, and classic boxwoods create beautiful curb appeal, while convenient main-level living makes the home as practical as it is welcoming. Inside, gleaming hardwood floors and abundant sunlight lend warmth to every room. The beautifully updated bath features a walk-in shower, and the centrally located kitchen offers generous cabinetry and plenty of room for shared meals. Ideally situated between the formal living room and cozy den, the kitchen provides an easy flow for everyday living and entertaining. Rich wood walls and a wood stove give the den its distinctive character. Adding a special piece of Winchester history, the paneling was salvaged from the former Lee-Jackson Hotel banquet room. Downstairs, the climate-controlled, partially finished lower level offers wonderful possibilities for a recreation room, playroom, home gym, or office, along with ample workshop and storage space. A relaxing screened porch overlooks the spacious backyard with peonies and a cherry tree, creating a peaceful spot to enjoy the outdoors. Lovingly cared for by the same family since it was built, this sweet home has been recently painted throughout and features roof (July 2025), new HVAC system (July 2026), update bathroom (2024) and newer 20-year tilt in windows, and updated lighting. Whether you are searching for your first home or looking to downsize, this special property is well worth a visit. Schedule your tour today!

3 Beds ⋅ 1 Baths

Charming, cheerful, and filled with natural light, this inviting 3-bedroom, 1-bath rancher makes a delightful first impression. Fresh yellow siding, mature trees, blooming hydrangeas, and classic boxwoods create beautiful curb appeal, while convenient main-level living makes the home as practical as it is welcoming. Inside, gleaming hardwood floors and abundant sunlight lend warmth to every room. The beautifully updated bath features a walk-in shower, and the centrally located kitchen offers generous cabinetry and plenty of room for shared meals. Ideally situated between the formal living room and cozy den, the kitchen provides an easy flow for everyday living and entertaining. Rich wood walls and a wood stove give the den its distinctive character. Adding a special piece of Winchester history, the paneling was salvaged from the former Lee-Jackson Hotel banquet room. Downstairs, the climate-controlled, partially finished lower level offers wonderful possibilities for a recreation room, playroom, home gym, or office, along with ample workshop and storage space. A relaxing screened porch overlooks the spacious backyard with peonies and a cherry tree, creating a peaceful spot to enjoy the outdoors. Lovingly cared for by the same family since it was built, this sweet home has been recently painted throughout and features roof (July 2025), new HVAC system (July 2026), update bathroom (2024) and newer 20-year tilt in windows, and updated lighting. Whether you are searching for your first home or looking to downsize, this special property is well worth a visit. Schedule your tour today!

1308 Commerce, Winchester

Listing courtesy of Colony Realty. Contact:

$719,000

Warm, elegant, and beautifully maintained, this 5-bedroom, 4.5-bath home offers gracious living in a desirable City of Winchester neighborhood with no HOA. Step into the spacious foyer, where refined crown molding and a striking staircase create a memorable first impression. Just beyond, a private office with built-in shelving and a cleverly concealed Murphy bed offers exceptional versatility, while the formal living room flows gracefully into a column-framed dining room designed for memorable gatherings. At the heart of the home, the bright and welcoming kitchen features an island cooktop and an adjoining breakfast area with double doors opening to a hardscaped patio - a lovely setting for morning coffee in the eastern sun. The family room invites you to settle in beneath vaulted ceilings beside the warmth of the gas fireplace, while a second staircase provides convenient access to the upper level. Upstairs, four generously sized bedrooms offer comfort and privacy, including two with en-suite baths, plus an additional full bath. The serene primary suite features two walk-in closets and a spacious bath with a soaking tub and separate walk-in shower. The finished lower level provides abundant space for entertaining, exercising, playing, or relaxing, along with generous storage, a half bath, and walk-up access to the backyard. Thoughtful updates include a new roof (2024), main-level HVAC (2026), upper-level HVAC (2023), updated carpeting (2018), and a kitchen refresh (2019). Immaculate, spacious, and wonderfully inviting, this exceptional home is ready to welcome its next owner. Schedule your private tour today.

5 Beds ⋅ 5 Baths

Warm, elegant, and beautifully maintained, this 5-bedroom, 4.5-bath home offers gracious living in a desirable City of Winchester neighborhood with no HOA. Step into the spacious foyer, where refined crown molding and a striking staircase create a memorable first impression. Just beyond, a private office with built-in shelving and a cleverly concealed Murphy bed offers exceptional versatility, while the formal living room flows gracefully into a column-framed dining room designed for memorable gatherings. At the heart of the home, the bright and welcoming kitchen features an island cooktop and an adjoining breakfast area with double doors opening to a hardscaped patio - a lovely setting for morning coffee in the eastern sun. The family room invites you to settle in beneath vaulted ceilings beside the warmth of the gas fireplace, while a second staircase provides convenient access to the upper level. Upstairs, four generously sized bedrooms offer comfort and privacy, including two with en-suite baths, plus an additional full bath. The serene primary suite features two walk-in closets and a spacious bath with a soaking tub and separate walk-in shower. The finished lower level provides abundant space for entertaining, exercising, playing, or relaxing, along with generous storage, a half bath, and walk-up access to the backyard. Thoughtful updates include a new roof (2024), main-level HVAC (2026), upper-level HVAC (2023), updated carpeting (2018), and a kitchen refresh (2019). Immaculate, spacious, and wonderfully inviting, this exceptional home is ready to welcome its next owner. Schedule your private tour today.

961 Meadow Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$298,900

PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, kitchen has been updated with granite countertops. Full basement partly finished basement, with workshop on a walk out to back yard. The outside shop is ready to set up shop with plenty of room for storage, and it has Electric! Great yard to enjoy all the seasons and relaxing. All this and so much more for $298,900.00.

2 Beds ⋅ 2 Baths

PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, kitchen has been updated with granite countertops. Full basement partly finished basement, with workshop on a walk out to back yard. The outside shop is ready to set up shop with plenty of room for storage, and it has Electric! Great yard to enjoy all the seasons and relaxing. All this and so much more for $298,900.00.

828 Woodland Ave, Winchester

Listing courtesy of Samson Properties. Contact:

$299,900

Updated, move-in ready, and waiting for you to make it your own! Welcome to 1013 Orchard Hill Dr. Tucked away in a charming, established Winchester neighborhood with no HOA, this inviting townhome combines a clean, comfortable style with many of the big-ticket improvements already taken care of. Outside, you'll find a brand-new roof and vinyl siding, fresh landscaping, and an updated rear deck complete with durable vinyl railing. Step inside to a spacious main level with an easy, open flow between the living and dining areas. The living room is warm and welcoming, centered around a wood-burning fireplace with built-in cabinetry on both sides, the perfect spot to settle in on a cool evening. The adjoining galley-style kitchen offers plenty of functionality with the laundry conveniently located just off the kitchen. Beyond the dining area, the home gets even better with a large bonus sunroom, complete with additional built-ins and an entire wall of pantry storage. Whether you envision it as a casual gathering space, home office, hobby area, or simply a place to enjoy the extra room, this flexible space adds even more versatility to the home. Upstairs, new carpeting runs throughout, complemented by fresh paint in the entire home. The brand-new full bathroom features a tub/shower combination and new vanity, giving the space a crisp, updated feel. The best part? The major exterior work has already been done, the home is clean and move-in ready, and there's still plenty of opportunity to bring your own style to the interior. Priced competitively, 1013 Orchard Hill Dr offers an opportunity to enjoy a desirable Winchester setting, the freedom of no HOA, and a home where the important updates have already been taken care of. Come see it for yourself and imagine what you'll do with the rest!

3 Beds ⋅ 2 Baths

Updated, move-in ready, and waiting for you to make it your own! Welcome to 1013 Orchard Hill Dr. Tucked away in a charming, established Winchester neighborhood with no HOA, this inviting townhome combines a clean, comfortable style with many of the big-ticket improvements already taken care of. Outside, you'll find a brand-new roof and vinyl siding, fresh landscaping, and an updated rear deck complete with durable vinyl railing. Step inside to a spacious main level with an easy, open flow between the living and dining areas. The living room is warm and welcoming, centered around a wood-burning fireplace with built-in cabinetry on both sides, the perfect spot to settle in on a cool evening. The adjoining galley-style kitchen offers plenty of functionality with the laundry conveniently located just off the kitchen. Beyond the dining area, the home gets even better with a large bonus sunroom, complete with additional built-ins and an entire wall of pantry storage. Whether you envision it as a casual gathering space, home office, hobby area, or simply a place to enjoy the extra room, this flexible space adds even more versatility to the home. Upstairs, new carpeting runs throughout, complemented by fresh paint in the entire home. The brand-new full bathroom features a tub/shower combination and new vanity, giving the space a crisp, updated feel. The best part? The major exterior work has already been done, the home is clean and move-in ready, and there's still plenty of opportunity to bring your own style to the interior. Priced competitively, 1013 Orchard Hill Dr offers an opportunity to enjoy a desirable Winchester setting, the freedom of no HOA, and a home where the important updates have already been taken care of. Come see it for yourself and imagine what you'll do with the rest!

1013 Orchard Hill Dr, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$389,000

A RARE DOWNTOWN GEM IN THE HEART OF HISTORIC WINCHESTER! Discover the charm and convenience of this beautifully restored circa-1900 row house, ideally located just one block from Winchester’s iconic Walking Mall. Enjoy an exceptional walkable lifestyle with an array of restaurants, coffee shops, boutiques, and nightlife right outside your door - all with no HOA! Thoughtfully renovated from top to bottom, this home combines historic character with modern comfort, featuring updated plumbing and electrical systems, beautiful hardwood flooring, and a spacious gourmet kitchen with granite countertops and convenient direct access to the rear deck featuring a relatively new 6' privacy fence—perfect for outdoor dining, entertaining or simply relaxing after a long day. Additional highlights include a front-loading washer and dryer, ceramic tile bath, high-end window treatments, and a generous walk-in closet. The transformation continues outside, where the fully restored and freshly painted exterior has just been completed, including a newly painted metal roof, along with a freshly restained rear deck and front porch. Fresh interior paint throughout adds to the bright, polished presentation. Beautifully updated, exceptionally located, and full of character, this special downtown property is truly move-in ready and a must-see! Enjoy extra storage in the clean & dry cellar space featuring solid concrete floors. Contact the listing agent today for more info or your own private showing.

2 Beds ⋅ 1 Baths

A RARE DOWNTOWN GEM IN THE HEART OF HISTORIC WINCHESTER! Discover the charm and convenience of this beautifully restored circa-1900 row house, ideally located just one block from Winchester’s iconic Walking Mall. Enjoy an exceptional walkable lifestyle with an array of restaurants, coffee shops, boutiques, and nightlife right outside your door - all with no HOA! Thoughtfully renovated from top to bottom, this home combines historic character with modern comfort, featuring updated plumbing and electrical systems, beautiful hardwood flooring, and a spacious gourmet kitchen with granite countertops and convenient direct access to the rear deck featuring a relatively new 6' privacy fence—perfect for outdoor dining, entertaining or simply relaxing after a long day. Additional highlights include a front-loading washer and dryer, ceramic tile bath, high-end window treatments, and a generous walk-in closet. The transformation continues outside, where the fully restored and freshly painted exterior has just been completed, including a newly painted metal roof, along with a freshly restained rear deck and front porch. Fresh interior paint throughout adds to the bright, polished presentation. Beautifully updated, exceptionally located, and full of character, this special downtown property is truly move-in ready and a must-see! Enjoy extra storage in the clean & dry cellar space featuring solid concrete floors. Contact the listing agent today for more info or your own private showing.

116 E Cork St, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$429,900

Fantastic location, classic brick charm, and plenty of space! This well-located brick rambler offers easy access to Route 50, Route 37, and I-81, while being just minutes from Valley Health. A long driveway, carport, concrete patio, and large, level backyard provide plenty of outdoor space and convenience. Inside, you’re welcomed by a light and bright living room featuring beautiful hardwood floors and a cozy fireplace. The kitchen opens directly to the dining room, creating a functional layout for everyday living and entertaining. The fully finished basement adds even more versatility, featuring two bedrooms, a spacious den with a second fireplace, and a kitchenette. Whether used for guests, extended living space, a home office, or recreation, the lower level offers plenty of possibilities. With a convenient location, generous yard, multiple living spaces, and a flexible finished basement, this home is ready to make your own!

5 Beds ⋅ 2 Baths

Fantastic location, classic brick charm, and plenty of space! This well-located brick rambler offers easy access to Route 50, Route 37, and I-81, while being just minutes from Valley Health. A long driveway, carport, concrete patio, and large, level backyard provide plenty of outdoor space and convenience. Inside, you’re welcomed by a light and bright living room featuring beautiful hardwood floors and a cozy fireplace. The kitchen opens directly to the dining room, creating a functional layout for everyday living and entertaining. The fully finished basement adds even more versatility, featuring two bedrooms, a spacious den with a second fireplace, and a kitchenette. Whether used for guests, extended living space, a home office, or recreation, the lower level offers plenty of possibilities. With a convenient location, generous yard, multiple living spaces, and a flexible finished basement, this home is ready to make your own!

337 George St, Winchester

Listing courtesy of Samson Properties. Contact:

$670,000

ONE LEVEL LIVING AND BRAND NEW ROOF in The Downs at Meadowbranch, a sought after community convenient to shopping, medical center, and Old Town Winchester. OPEN SATURDAY 10/10 FROM 1-3PM! Expansive all-brick home offers 3 bedrooms, 2 bathrooms, attached 2-car garage and 2450 square feet of living space! What's better than an idyllic 1/5 acre corner lot... how about an idyllic 1/5 acre corner lot you don't have to mow? HOA fees include lawn mowing, mulching, leaf clean up, and tree and shrub maintenance! Hardwood floors run through the living and dining rooms, kitchen, and the 2nd and 3rd bedrooms. Charming country kitchen features granite counters and stainless steel appliances, as well as a cozy breakfast nook, and access to the screened porch with ceiling fan. Large living room with gas fireplace. Formal dining room boasts chair and crown molding. Primary bedroom has walk in closet and en-suite bath with double vanity, jetted tub and separate shower. Bathrooms and bedrooms have been FRESHLY PAINTED. This is a great opportunity to own in a desirable rarely-available City of Winchester community! Schedule your tour today!

3 Beds ⋅ 2 Baths

ONE LEVEL LIVING AND BRAND NEW ROOF in The Downs at Meadowbranch, a sought after community convenient to shopping, medical center, and Old Town Winchester. OPEN SATURDAY 10/10 FROM 1-3PM! Expansive all-brick home offers 3 bedrooms, 2 bathrooms, attached 2-car garage and 2450 square feet of living space! What's better than an idyllic 1/5 acre corner lot... how about an idyllic 1/5 acre corner lot you don't have to mow? HOA fees include lawn mowing, mulching, leaf clean up, and tree and shrub maintenance! Hardwood floors run through the living and dining rooms, kitchen, and the 2nd and 3rd bedrooms. Charming country kitchen features granite counters and stainless steel appliances, as well as a cozy breakfast nook, and access to the screened porch with ceiling fan. Large living room with gas fireplace. Formal dining room boasts chair and crown molding. Primary bedroom has walk in closet and en-suite bath with double vanity, jetted tub and separate shower. Bathrooms and bedrooms have been FRESHLY PAINTED. This is a great opportunity to own in a desirable rarely-available City of Winchester community! Schedule your tour today!

1400 Gordon Pl, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$299,900

Enjoy downtown Winchester living with plenty of flexibility! This 4-bedroom, 2.5-bath townhome offers a functional layout in a convenient location close to restaurants, shopping, schools, Handley games, and all that downtown Winchester has to offer. The main level features a comfortable living area, kitchen with eat-in space, and access to a beautiful Trex deck overlooking the fully fenced backyard. Upstairs, you'll find three bedrooms and a full bath. The finished walk-out lower level adds even more versatility with a fourth bedroom, full bath, and laundry area. Step outside to a stamped concrete patio and fenced yard with storage shed. With multiple outdoor living spaces, off-street parking, and an incredibly convenient location, this home offers plenty of possibilities inside and out.

4 Beds ⋅ 3 Baths

Enjoy downtown Winchester living with plenty of flexibility! This 4-bedroom, 2.5-bath townhome offers a functional layout in a convenient location close to restaurants, shopping, schools, Handley games, and all that downtown Winchester has to offer. The main level features a comfortable living area, kitchen with eat-in space, and access to a beautiful Trex deck overlooking the fully fenced backyard. Upstairs, you'll find three bedrooms and a full bath. The finished walk-out lower level adds even more versatility with a fourth bedroom, full bath, and laundry area. Step outside to a stamped concrete patio and fenced yard with storage shed. With multiple outdoor living spaces, off-street parking, and an incredibly convenient location, this home offers plenty of possibilities inside and out.

1 E Hart St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$284,900

Enjoy the convenience of downtown Winchester living in this charming 2-bedroom, 2-bath townhome, ideally located within walking distance of restaurants, shopping, school games and more. The main level features a comfortable living area and an eat-in kitchen with doors leading to a beautiful Trex deck, perfect for morning coffee, grilling or relaxing at the end of the day. Upstairs, both bedrooms offer their own en-suite baths, with the primary bedroom also featuring a walk-in closet. The finished basement adds valuable bonus space with plenty of flexibility for a rec room, home gym, office or additional living area. From there, walk out to a beautiful stamped concrete patio and fully fenced backyard with a storage shed. With two great outdoor living spaces, a finished lower level and a location that makes it easy to enjoy everything downtown Winchester has to offer, this townhome packs a lot into a convenient footprint.

2 Beds ⋅ 3 Baths

Enjoy the convenience of downtown Winchester living in this charming 2-bedroom, 2-bath townhome, ideally located within walking distance of restaurants, shopping, school games and more. The main level features a comfortable living area and an eat-in kitchen with doors leading to a beautiful Trex deck, perfect for morning coffee, grilling or relaxing at the end of the day. Upstairs, both bedrooms offer their own en-suite baths, with the primary bedroom also featuring a walk-in closet. The finished basement adds valuable bonus space with plenty of flexibility for a rec room, home gym, office or additional living area. From there, walk out to a beautiful stamped concrete patio and fully fenced backyard with a storage shed. With two great outdoor living spaces, a finished lower level and a location that makes it easy to enjoy everything downtown Winchester has to offer, this townhome packs a lot into a convenient footprint.

5 E Hart St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$305,500

Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently located on the main level, along with a dedicated office that provides a great space for working from home, hobbies, or additional flex space. One of the two full bathrooms is brand new, adding a fresh modern touch to this classic home.

3 Beds ⋅ 2 Baths

Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently located on the main level, along with a dedicated office that provides a great space for working from home, hobbies, or additional flex space. One of the two full bathrooms is brand new, adding a fresh modern touch to this classic home.

3 S Euclid Ave, Winchester

Listing courtesy of Main Street Realty. Contact:

$349,900

Some homes simply feel right the moment you arrive—and this charming Cape Cod in an ideal in‑town Winchester location is one of them. Offering 3–4 bedrooms and 2.5 bathrooms, the layout flows with an easy, everyday comfort. The main level features two convenient bedrooms, a bright and inviting living room, a dedicated dining area, and a renovated kitchen with new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh, including new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, updated receptacles/switches/covers, a new roof, and updated plumbing for added peace of mind. Upstairs, two additional rooms and a full bathroom provide flexible space—whether you envision a fourth bedroom, office, or bonus retreat. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and direct walkout access to the backyard, creating an ideal setting for a second living area, guest space, or recreation zone. Outdoors, a spacious deck and fully fenced backyard with privacy fencing offer a comfortable retreat perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this is just moments from downtown Winchester’s shopping, restaurants, and everyday conveniences. Schedule your tour today and experience the feeling for yourself.

4 Beds ⋅ 3 Baths

Some homes simply feel right the moment you arrive—and this charming Cape Cod in an ideal in‑town Winchester location is one of them. Offering 3–4 bedrooms and 2.5 bathrooms, the layout flows with an easy, everyday comfort. The main level features two convenient bedrooms, a bright and inviting living room, a dedicated dining area, and a renovated kitchen with new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh, including new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, updated receptacles/switches/covers, a new roof, and updated plumbing for added peace of mind. Upstairs, two additional rooms and a full bathroom provide flexible space—whether you envision a fourth bedroom, office, or bonus retreat. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and direct walkout access to the backyard, creating an ideal setting for a second living area, guest space, or recreation zone. Outdoors, a spacious deck and fully fenced backyard with privacy fencing offer a comfortable retreat perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this is just moments from downtown Winchester’s shopping, restaurants, and everyday conveniences. Schedule your tour today and experience the feeling for yourself.

621 Patterson Ave, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$839,000

Welcome to 922 Armistead Street, a spacious brick Colonial in Winchester's established Morlyn Hills neighborhood offering approximately 4,697 finished square feet across three levels. The light-filled main level features hardwood floors, a private office with built-ins, formal living and dining rooms, and a generous kitchen with island and breakfast area opening to the family room with fireplace. Upstairs, the expansive primary suite includes a large walk-in closet and private bath, along with three additional bedrooms, two additional full baths, and convenient upper-level laundry. The finished lower level offers a large recreation room, exercise room, bonus room, full bath, and additional unfinished storage. Outside, enjoy a fenced backyard and spacious stone patio, plus an attached two-car garage. Improvements within the past five years include replacement of both Carrier HVAC systems, water heater, Pella front door and frame, garage doors and framing, and updated appliances, including Samsung refrigerator, Miele dishwasher, and LG washer and dryer, all conveying. No HOA. Convenient to downtown Winchester, Valley Health, Shenandoah University, and Routes 7, 11, 37, and I-81.

4 Beds ⋅ 5 Baths

Welcome to 922 Armistead Street, a spacious brick Colonial in Winchester's established Morlyn Hills neighborhood offering approximately 4,697 finished square feet across three levels. The light-filled main level features hardwood floors, a private office with built-ins, formal living and dining rooms, and a generous kitchen with island and breakfast area opening to the family room with fireplace. Upstairs, the expansive primary suite includes a large walk-in closet and private bath, along with three additional bedrooms, two additional full baths, and convenient upper-level laundry. The finished lower level offers a large recreation room, exercise room, bonus room, full bath, and additional unfinished storage. Outside, enjoy a fenced backyard and spacious stone patio, plus an attached two-car garage. Improvements within the past five years include replacement of both Carrier HVAC systems, water heater, Pella front door and frame, garage doors and framing, and updated appliances, including Samsung refrigerator, Miele dishwasher, and LG washer and dryer, all conveying. No HOA. Convenient to downtown Winchester, Valley Health, Shenandoah University, and Routes 7, 11, 37, and I-81.

922 Armistead St, Winchester

Listing courtesy of Cottage Street Realty LLC. Contact:

$605,000

Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location! Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers convenience, charm, and long-term value. The building features two 2-Bedroom, 1-Bath Units – Each offers large Kitchens, updated finishes, and their own Laundry Rooms. One of the units is ground level, and the other 2nd-Level unit has access to its own deck space. The largest unit of the three features two finished levels, connected with an interior staircase, 5-Bedrooms, 2 Full Baths, 2 Living Rooms, a Full kitchen, Laundry, and access to it's own private patio & deck. It's a unique two-level layout, perfect for multi-tenants and/or premium rental rates. Recent renovations throughout the last few years include: Luxury vinyl plank (LVP) flooring, fresh paint, and updated kitchens and baths Newer appliances in each unit The roof less than 3 years old New HVAC installed (2025) Designated parking for all units With all units currently leased, this is a true turnkey investment with reliable income and minimal immediate maintenance needs. This well-maintained building features three fully occupied units, bringing in a current gross annual rental income of $45,300. Whether you're looking to grow your portfolio or occupy a unit while renting the others, or the potential for a short-term rental, this property checks all the boxes!

540 Monticello St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$555,000

Beautiful hardwood floors and ceramic tile throughout, complemented by a spacious open floor plan. Enjoy a private rear yard, with shopping and commuter routes just minutes away. The breakfast bar features a gas 5-burner cooktop — perfect for casual meals and entertaining. A spacious dining room showcases elegant shadow box trim and crown molding. Additional highlights include a full front porch, a 2-car garage with remote access, and a luxurious master bedroom retreat complete with a whirlpool tub, separate shower, and walk-in closets. Brand new water heater. Roof 2 years

4 Beds ⋅ 4 Baths

Beautiful hardwood floors and ceramic tile throughout, complemented by a spacious open floor plan. Enjoy a private rear yard, with shopping and commuter routes just minutes away. The breakfast bar features a gas 5-burner cooktop — perfect for casual meals and entertaining. A spacious dining room showcases elegant shadow box trim and crown molding. Additional highlights include a full front porch, a 2-car garage with remote access, and a luxurious master bedroom retreat complete with a whirlpool tub, separate shower, and walk-in closets. Brand new water heater. Roof 2 years

Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$325,000

Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent condition, creating a warm and welcoming atmosphere that is ready for its next owner to enjoy. Outside, the spacious lot provides plenty of room to relax, entertain, garden, play, or simply enjoy having some extra breathing room without sacrificing the convenience of being in the city. One of the property's standout features is the abundance of parking available in front of the home, making it easy to accommodate multiple vehicles and guests. Whether you're hosting family and friends or simply appreciate having extra parking space, this home delivers. Location is another major highlight. Enjoy convenient access to Downtown Winchester, shopping, restaurants, schools, parks, everyday necessities, and major commuter routes, while still coming home to a property with plenty of outdoor space to call your own. With its generous lot, well-cared-for condition, ample parking, and convenient Winchester location, 2817 Papermill Road offers a combination that's increasingly hard to find. Come see what makes this home special—you may just find the space, location, and feeling of home you've been looking for.

3 Beds ⋅ 2 Baths

Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent condition, creating a warm and welcoming atmosphere that is ready for its next owner to enjoy. Outside, the spacious lot provides plenty of room to relax, entertain, garden, play, or simply enjoy having some extra breathing room without sacrificing the convenience of being in the city. One of the property's standout features is the abundance of parking available in front of the home, making it easy to accommodate multiple vehicles and guests. Whether you're hosting family and friends or simply appreciate having extra parking space, this home delivers. Location is another major highlight. Enjoy convenient access to Downtown Winchester, shopping, restaurants, schools, parks, everyday necessities, and major commuter routes, while still coming home to a property with plenty of outdoor space to call your own. With its generous lot, well-cared-for condition, ample parking, and convenient Winchester location, 2817 Papermill Road offers a combination that's increasingly hard to find. Come see what makes this home special—you may just find the space, location, and feeling of home you've been looking for.

2817 Papermill Rd, Winchester

Listing courtesy of Weichert, REALTORS. Contact: