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Enjoy your morning coffee sitting in the sunroom overlooking your spacious private back yard & patio. This lovingly cared for home is just waiting for you to make your own personal updates. 3 Bedrooms and 2 Baths on the main level plus a Full basement with a finished Rec Room, library and tons of storage space.

3 Beds ⋅ 2 Baths

Enjoy your morning coffee sitting in the sunroom overlooking your spacious private back yard & patio. This lovingly cared for home is just waiting for you to make your own personal updates. 3 Bedrooms and 2 Baths on the main level plus a Full basement with a finished Rec Room, library and tons of storage space.

508 Lanny Dr, Winchester

Listing courtesy of Corcoran McEnearney. Contact:

$610,000

Discover exceptional one-level living in one of Winchester’s premier communities, where homes rarely become available! This exquisite all-brick home combines timeless elegance, thoughtful updates, and a peaceful setting. Hardwood floors flow throughout the main living areas, complementing the formal dining room, living room and beautifully updated kitchen featuring high-end granite countertops, stainless steel appliances, induction range, ultra-quiet Bosch dishwasher, and convenient bar seating. The adjoining den, currently used as a sitting area, could easily serve as a breakfast room to suit your needs. A stunning three-sided gas fireplace creates a warm, inviting atmosphere, enjoyed from the living room, den, and kitchen. Step into the screened-in florida room and discover a tranquil backyard retreat backing to mature trees, complete with an English-inspired garden and private patio—perfect for relaxing or entertaining. The attached two-car garage includes an EV charger for added convenience. Even better, the HOA takes care of lawn maintenance, landscaping, and snow removal, allowing you to enjoy a low-maintenance lifestyle without sacrificing the benefits of a beautiful private home. While the community offers a peaceful, low-maintenance environment often associated with 55+ living, there is no age restriction. Enjoy an established neighborhood with mature trees and a serene atmosphere, conveniently located just one mile from the hospital and approximately 1.5 miles from Old Town Winchester. Commuter routes are easily accessible, and local apple orchards and pumpkin farms are just minutes away. Rarely available and ideally situated, this exceptional home offers comfort, convenience, and carefree living. Make it yours today!

3 Beds ⋅ 2 Baths

Discover exceptional one-level living in one of Winchester’s premier communities, where homes rarely become available! This exquisite all-brick home combines timeless elegance, thoughtful updates, and a peaceful setting. Hardwood floors flow throughout the main living areas, complementing the formal dining room, living room and beautifully updated kitchen featuring high-end granite countertops, stainless steel appliances, induction range, ultra-quiet Bosch dishwasher, and convenient bar seating. The adjoining den, currently used as a sitting area, could easily serve as a breakfast room to suit your needs. A stunning three-sided gas fireplace creates a warm, inviting atmosphere, enjoyed from the living room, den, and kitchen. Step into the screened-in florida room and discover a tranquil backyard retreat backing to mature trees, complete with an English-inspired garden and private patio—perfect for relaxing or entertaining. The attached two-car garage includes an EV charger for added convenience. Even better, the HOA takes care of lawn maintenance, landscaping, and snow removal, allowing you to enjoy a low-maintenance lifestyle without sacrificing the benefits of a beautiful private home. While the community offers a peaceful, low-maintenance environment often associated with 55+ living, there is no age restriction. Enjoy an established neighborhood with mature trees and a serene atmosphere, conveniently located just one mile from the hospital and approximately 1.5 miles from Old Town Winchester. Commuter routes are easily accessible, and local apple orchards and pumpkin farms are just minutes away. Rarely available and ideally situated, this exceptional home offers comfort, convenience, and carefree living. Make it yours today!

827 Buckner Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$399,900

Welcome to 338 E Piccadilly Street, a beautifully updated 3-bedroom, 2-bathroom home perfectly positioned in a highly convenient Winchester location. Overflowing with natural light and seamless charm, this move-in ready residence effortlessly blends classic architectural characteristics with high-end modern finishes and thoughtful details throughout. The inviting curb appeal begins with a freshly paved front walkway leading to a covered front porch framed by classic arches and complete with an adorable porch swing. Inside, the bright foyer opens into a warm living room with rich hardwood flooring that flows seamlessly into the beautifully redesigned kitchen. A standout focal point of the main level, it boasts a chic two-tone design with bright white upper cabinetry grounded by sophisticated muted green lowers, accented by a gorgeous backsplash, stainless steel appliances, and upgraded fixtures. Designed with entertaining in mind, the adjacent dining room features custom built-in cabinets, a distinct exposed brick pillar, and a separate wet bar complete with counter space, sink, and wine fridge. Just off the dining area, a dedicated laundry room provides direct access to the rear deck, alongside an updated full bath complete with a new vanity, fresh flooring, and a subway tile tub/shower with a glass surround. Downstairs, an unfinished basement provides excellent additional storage space. Upstairs, you will find three bedrooms, including a primary retreat with an attached light-filled sunroom/bonus space—a fabulous layout for a massive walk-in closet, home office, workout room, or playroom. Two additional bedrooms share this level with a beautifully renovated full bathroom that truly shines, highlighted by a classic clawfoot tub, stylish flooring, and a sleek new vanity. Outside, the private backyard is perfect for relaxing or entertaining, complete with a deck and a newer privacy fence ideal for pets or outdoor gatherings. Convenient off-street parking is provided by a driveway plus a detached storage building with alley access. This home also offers total peace of mind with major upgrades completed in recent years, including a 2-year-old HVAC system with heat pump and 3 mini-splits, an upgraded 200-amp electrical panel, newer supply plumbing, and a newer roof, siding, gutters, and insulation. Combining historic Winchester charm, extensive modern upgrades, and unbeatable proximity to downtown dining, parks, schools, and commuter routes, this exceptional home is truly turn-key living at its finest.

3 Beds ⋅ 2 Baths

Welcome to 338 E Piccadilly Street, a beautifully updated 3-bedroom, 2-bathroom home perfectly positioned in a highly convenient Winchester location. Overflowing with natural light and seamless charm, this move-in ready residence effortlessly blends classic architectural characteristics with high-end modern finishes and thoughtful details throughout. The inviting curb appeal begins with a freshly paved front walkway leading to a covered front porch framed by classic arches and complete with an adorable porch swing. Inside, the bright foyer opens into a warm living room with rich hardwood flooring that flows seamlessly into the beautifully redesigned kitchen. A standout focal point of the main level, it boasts a chic two-tone design with bright white upper cabinetry grounded by sophisticated muted green lowers, accented by a gorgeous backsplash, stainless steel appliances, and upgraded fixtures. Designed with entertaining in mind, the adjacent dining room features custom built-in cabinets, a distinct exposed brick pillar, and a separate wet bar complete with counter space, sink, and wine fridge. Just off the dining area, a dedicated laundry room provides direct access to the rear deck, alongside an updated full bath complete with a new vanity, fresh flooring, and a subway tile tub/shower with a glass surround. Downstairs, an unfinished basement provides excellent additional storage space. Upstairs, you will find three bedrooms, including a primary retreat with an attached light-filled sunroom/bonus space—a fabulous layout for a massive walk-in closet, home office, workout room, or playroom. Two additional bedrooms share this level with a beautifully renovated full bathroom that truly shines, highlighted by a classic clawfoot tub, stylish flooring, and a sleek new vanity. Outside, the private backyard is perfect for relaxing or entertaining, complete with a deck and a newer privacy fence ideal for pets or outdoor gatherings. Convenient off-street parking is provided by a driveway plus a detached storage building with alley access. This home also offers total peace of mind with major upgrades completed in recent years, including a 2-year-old HVAC system with heat pump and 3 mini-splits, an upgraded 200-amp electrical panel, newer supply plumbing, and a newer roof, siding, gutters, and insulation. Combining historic Winchester charm, extensive modern upgrades, and unbeatable proximity to downtown dining, parks, schools, and commuter routes, this exceptional home is truly turn-key living at its finest.

338 E Piccadilly St, Winchester

Listing courtesy of Colony Realty. Contact:

$645,000

This home is not just a property; it's a place where memories are made and cherished. Don't miss the opportunity to make this delightful residence your own. Metal roof (2018), solar pBuilt in 1930 on one of the most desirable streets in downtown Winchester, this charming Colonial exudes timeless elegance and warmth. Its classic brick construction stands the test of time, complemented by beautifully maintained landscaped grounds, while the private and secluded rear yard — designed by a master gardener — offers the perfect setting for outdoor gatherings or quiet moments of reflection. Step inside to discover a spacious layout with four bedrooms and two full bathrooms, ideal for both relaxation and entertaining, with surprisingly spacious closets completing each bedroom. Just off the kitchen, the den would be perfect for a library, playroom, or additional main level bedroom. The surprise walk-up finished attic would make a perfect exercise space, office, or guest retreat with built in closets. Hardwood flooring runs throughout, adding a touch of sophistication, and the cozy wood-burning fireplace with a custom built mantle serves as the focal point of the living area, inviting you to unwind on chilly evenings. Practicality is woven in throughout: the attached garage provides convenient access, and both the garage and the unfinished basement offer loads of storage space. With a focus on sustainability, the home features a 16-panel PV solar array that promotes energy efficiency and reduces utility costs. Imagine enjoying your morning coffee in the peaceful rear yard, surrounded by lush landscaping — or better yet, on your private upper covered porch featuring black walnut flooring. This home is not just a property; it's a place where memories are made and cherished. Don't miss the opportunity to make this delightful residence your own. Metal roof (2018), solar panels (2021), new A/C (2020) — see docs for additional upgrades.

4 Beds ⋅ 2 Baths

This home is not just a property; it's a place where memories are made and cherished. Don't miss the opportunity to make this delightful residence your own. Metal roof (2018), solar pBuilt in 1930 on one of the most desirable streets in downtown Winchester, this charming Colonial exudes timeless elegance and warmth. Its classic brick construction stands the test of time, complemented by beautifully maintained landscaped grounds, while the private and secluded rear yard — designed by a master gardener — offers the perfect setting for outdoor gatherings or quiet moments of reflection. Step inside to discover a spacious layout with four bedrooms and two full bathrooms, ideal for both relaxation and entertaining, with surprisingly spacious closets completing each bedroom. Just off the kitchen, the den would be perfect for a library, playroom, or additional main level bedroom. The surprise walk-up finished attic would make a perfect exercise space, office, or guest retreat with built in closets. Hardwood flooring runs throughout, adding a touch of sophistication, and the cozy wood-burning fireplace with a custom built mantle serves as the focal point of the living area, inviting you to unwind on chilly evenings. Practicality is woven in throughout: the attached garage provides convenient access, and both the garage and the unfinished basement offer loads of storage space. With a focus on sustainability, the home features a 16-panel PV solar array that promotes energy efficiency and reduces utility costs. Imagine enjoying your morning coffee in the peaceful rear yard, surrounded by lush landscaping — or better yet, on your private upper covered porch featuring black walnut flooring. This home is not just a property; it's a place where memories are made and cherished. Don't miss the opportunity to make this delightful residence your own. Metal roof (2018), solar panels (2021), new A/C (2020) — see docs for additional upgrades.

411 W Cecil St, Winchester

Listing courtesy of Colony Realty. Contact:

$579,000

Have you been looking for houses that just lack the one thing you really wanted or needed? I think I can confidently say, the search is over. Allow me to present 606 Pritchards Hill Ct, Winchester, VA 22601 to you. Once you walk through this four bedroom, three and one half bath single family home located in the city of Winchester, Virginia, you will agree with the feeling of decadence. Some preliminary key attributes: two car garage, finished basement, and a large mostly flat rear yard with a raised flower bed, and mostly hardwood floors in all hosting areas. Let’s start the tour with the large front porch that signifies the beauty of the Southern design. The porch is just meant for rocking chairs, plants, to hand out candy on Halloween, or just to do up a storm of decorations for the holidays. Key notables when you enter the home: two story foyer, the formal living room to your right, and the formal dining room on the right side that conveniently connects to the kitchen. Doors on both sides of the living room allow it to easily be used as an office. Let’s head to the kitchen, where you may notice some refreshing characteristics: Slow closing drawers and cabinets, deep single sink with upgraded facet, multi-level granite counter tops allows for quick countertop meals, large multi-window bay window in breakfast nook, TWO pantries, a separate coffee station with a designated water line, additional beverage cooler under countertop, all stainless steel appliances with fridge offering water and multi ice dispensers. Heading to the rear of the home off the living room, you will notice: covered patio with recessed lights and an outdoor fan, upgraded landscaping allowing shade and sun to the home and covered patio, completely fenced rear yard with two separate gates, and raised vegetable garden in the rear has an irrigation system that runs through it. Moving towards the second floor, here is what is in store: large rear facing primary bedroom, separate jetted soaking tub in the primary bathroom, sizable walk-in closet with closet organizers, additional space above the commode in the water closet, upstair laundry, very large bedroom above garage can be a second primary if desired, and hallway bedroom has upgraded crown molding. Finally, the basement has several remarkable features: the home is sold with a pool table because that room has the built-in housing for billiard room accessories, heated tile floors, extra room with attached full bathroom is great for spare bedroom or home gym, double doors take you to a hobby space that can used as a poker room, bar, craft area, etc., additional room with a full size kitchen sink and a separate water line for another fridge, and plenty of finished space under the staircase or in the hallway to the rear exit. Other key features to note: vast lighting in the garage with high ceiling and built-in storage shelving above the garage doors, additional shelves throughout the garage ideal for home projects or storage, water bib inside the garage for front of home to prevent freezing, wi-fi thermostats and front door lock so you can control from your phone while on vacation, a large tree next to the garage to help shade any cars not parked in the garage, longer driveway can fit at least 4 standard cars, landscape lighting in both front and backyard, plus many many more. Agent/owner

4 Beds ⋅ 4 Baths

Have you been looking for houses that just lack the one thing you really wanted or needed? I think I can confidently say, the search is over. Allow me to present 606 Pritchards Hill Ct, Winchester, VA 22601 to you. Once you walk through this four bedroom, three and one half bath single family home located in the city of Winchester, Virginia, you will agree with the feeling of decadence. Some preliminary key attributes: two car garage, finished basement, and a large mostly flat rear yard with a raised flower bed, and mostly hardwood floors in all hosting areas. Let’s start the tour with the large front porch that signifies the beauty of the Southern design. The porch is just meant for rocking chairs, plants, to hand out candy on Halloween, or just to do up a storm of decorations for the holidays. Key notables when you enter the home: two story foyer, the formal living room to your right, and the formal dining room on the right side that conveniently connects to the kitchen. Doors on both sides of the living room allow it to easily be used as an office. Let’s head to the kitchen, where you may notice some refreshing characteristics: Slow closing drawers and cabinets, deep single sink with upgraded facet, multi-level granite counter tops allows for quick countertop meals, large multi-window bay window in breakfast nook, TWO pantries, a separate coffee station with a designated water line, additional beverage cooler under countertop, all stainless steel appliances with fridge offering water and multi ice dispensers. Heading to the rear of the home off the living room, you will notice: covered patio with recessed lights and an outdoor fan, upgraded landscaping allowing shade and sun to the home and covered patio, completely fenced rear yard with two separate gates, and raised vegetable garden in the rear has an irrigation system that runs through it. Moving towards the second floor, here is what is in store: large rear facing primary bedroom, separate jetted soaking tub in the primary bathroom, sizable walk-in closet with closet organizers, additional space above the commode in the water closet, upstair laundry, very large bedroom above garage can be a second primary if desired, and hallway bedroom has upgraded crown molding. Finally, the basement has several remarkable features: the home is sold with a pool table because that room has the built-in housing for billiard room accessories, heated tile floors, extra room with attached full bathroom is great for spare bedroom or home gym, double doors take you to a hobby space that can used as a poker room, bar, craft area, etc., additional room with a full size kitchen sink and a separate water line for another fridge, and plenty of finished space under the staircase or in the hallway to the rear exit. Other key features to note: vast lighting in the garage with high ceiling and built-in storage shelving above the garage doors, additional shelves throughout the garage ideal for home projects or storage, water bib inside the garage for front of home to prevent freezing, wi-fi thermostats and front door lock so you can control from your phone while on vacation, a large tree next to the garage to help shade any cars not parked in the garage, longer driveway can fit at least 4 standard cars, landscape lighting in both front and backyard, plus many many more. Agent/owner

606 Pritchards Hill Ct, Winchester

Listing courtesy of Realty FC. 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:

$540,000

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:

$247,000

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:

$269,900

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:

$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:

$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:

$529,000

An exceptional multifamily investment opportunity awaits in the heart of historic downtown Winchester! Located at 440 N Braddock St, this turnkey property features a timeless brick exterior, rich historic charm, and beautiful hardwood floors throughout. The property comprises three distinct, light-filled units, each designed with two spacious bedrooms and one full bathroom. Tenants will love the shared outdoor living space in the backyard—ideal for relaxing or entertaining—along with the added convenience of a detached garage. Clean, well-maintained, and ready to lease, this prime asset offers outstanding rental potential just steps from the popular downtown walking mall, local dining, shopping, and everything Winchester has to offer. Whether you are expanding your portfolio or looking for a premium income-producing property, this versatile investment is ready for immediate income generation.

440 N Braddock St, Winchester

Listing courtesy of Colony Realty. Contact:

$625,000

Awesome income-producing multi-unit property in the heart of downtown Winchester. This stately red brick building delivers immediate cash flow with a great documented CAP rate and all three units currently occupied with tenants paying all utilities. High ceilings and abundant natural light create desirable living spaces. Located just a half-block from the Winchester walking mall, residents enjoy walkable access to dining, shopping, and entertainment. The unfinished basement presents expansion potential for tenant storage or additional unit conversion, with the possibility of growing from 3 to 4 units. Street parking available with a public lot one block away. No HOA fees. A rare opportunity for portfolio growth in a prime downtown location.

25 W Boscawen St, Winchester

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

$499,900

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds.

3 Beds ⋅ 3 Baths

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds.

510 S Cameron St, Winchester

Listing courtesy of Samson Properties. Contact:

$400,000

Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

4 Beds ⋅ 1 Baths

Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

322 E Piccadilly, Winchester

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

$419,000

Larger than it appears, this beautiful 3‑bedroom, 2‑bathroom home sits on a convenient street just minutes from historic downtown Winchester. The location offers effortless access to main commuter roads, making daily travel smooth and stress‑free. It’s also close to Shenandoah University, adding even more appeal for investors, students, faculty, or anyone who values proximity to campus and city amenities. Inside, the layout provides exceptional flexibility — the home can function as two completely separate rentals, giving it true income‑producing capabilities while maintaining all the original details you provided. A nice deck extends your living space outdoors, overlooking a large, flat, fully fenced backyard perfect for relaxing, entertaining, or tenant use. This is a great opportunity in a prime Winchester location. Come take a look and see the potential for yourself.

3 Beds ⋅ 2 Baths

Larger than it appears, this beautiful 3‑bedroom, 2‑bathroom home sits on a convenient street just minutes from historic downtown Winchester. The location offers effortless access to main commuter roads, making daily travel smooth and stress‑free. It’s also close to Shenandoah University, adding even more appeal for investors, students, faculty, or anyone who values proximity to campus and city amenities. Inside, the layout provides exceptional flexibility — the home can function as two completely separate rentals, giving it true income‑producing capabilities while maintaining all the original details you provided. A nice deck extends your living space outdoors, overlooking a large, flat, fully fenced backyard perfect for relaxing, entertaining, or tenant use. This is a great opportunity in a prime Winchester location. Come take a look and see the potential for yourself.

1412 S Loudoun St, Winchester

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

$349,900

Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, making meal prep a delight. A generous size family room just off the kitchen. Enjoy the convenience of main-floor laundry and a partially finished basement, perfect for a cozy retreat on gameday, or even possible 3rd bedroom, & couple extra rooms for storage. The attic could also add potential living space.(possible 4th) The inviting outdoor space is ideal for relaxation, Brand New Garage while the driveway provides ample off-street parking. Nestled in a vibrant community, residents benefit from nearby parks, excellent schools, Shenandoah University and convenient public services. Experience the warmth of neighborhood gatherings and the charm of local shops. This home is not just a place to live; it's a place to thrive. Embrace the lifestyle you've been dreaming of!

2 Beds ⋅ 2 Baths

Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, making meal prep a delight. A generous size family room just off the kitchen. Enjoy the convenience of main-floor laundry and a partially finished basement, perfect for a cozy retreat on gameday, or even possible 3rd bedroom, & couple extra rooms for storage. The attic could also add potential living space.(possible 4th) The inviting outdoor space is ideal for relaxation, Brand New Garage while the driveway provides ample off-street parking. Nestled in a vibrant community, residents benefit from nearby parks, excellent schools, Shenandoah University and convenient public services. Experience the warmth of neighborhood gatherings and the charm of local shops. This home is not just a place to live; it's a place to thrive. Embrace the lifestyle you've been dreaming of!

1414 S Braddock St, Winchester

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

$235,000

Roof replaced in 2020. Water heater: 2026. NEW PRICE! Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a convenient half bath. Upstairs offers two generously sized bedrooms with ample closet space and a full bath. Step outside to the Trex deck and manageable backyard, perfect for relaxing or entertaining. Off-street parking for two vehicles is a rare bonus in this downtown location. Whether you're a first-time buyer, downsizer, or investor, this home offers comfort, convenience, and an excellent location with easy access to I-81 and Northern Virginia. Enjoy everything Winchester has to offer, including the vibrant Old Town district, locally owned restaurants and boutiques, breweries, cultural attractions, and historic landmarks. Schedule your private showing today! All sizes are approximate. Sold "AS IS" - inspection for informational purposes. Prior inspection findings available upon request.

2 Beds ⋅ 2 Baths

Roof replaced in 2020. Water heater: 2026. NEW PRICE! Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a convenient half bath. Upstairs offers two generously sized bedrooms with ample closet space and a full bath. Step outside to the Trex deck and manageable backyard, perfect for relaxing or entertaining. Off-street parking for two vehicles is a rare bonus in this downtown location. Whether you're a first-time buyer, downsizer, or investor, this home offers comfort, convenience, and an excellent location with easy access to I-81 and Northern Virginia. Enjoy everything Winchester has to offer, including the vibrant Old Town district, locally owned restaurants and boutiques, breweries, cultural attractions, and historic landmarks. Schedule your private showing today! All sizes are approximate. Sold "AS IS" - inspection for informational purposes. Prior inspection findings available upon request.

103 E Germain St, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$350,000

PRICE IMPROVEMENT! NO HOA! Close to Route 11, 37, I-81- Space, Flexibility, Updates & a Beautifully Landscaped Backyard! Discover the possibilities in this spacious and versatile townhome offering a unique multi-level floor plan, inviting living spaces, and wonderful outdoor enjoyment. Thoughtful updates include a new roof and heat pump in 2025, a new hot water heater in 2026, and a beautifully remodeled full bath in 2024, making this home an exciting opportunity for its next owner! The main level welcomes you with a bright and cheerful living room featuring hardwood floors, a charming bay window, built-in shelving, and a wood-burning fireplace that creates the perfect setting for cozy evenings. The separate dining room is enhanced by crown molding and chair rail and offers a convenient closet for storing china and linens. The updated kitchen features Corian countertops, a sink overlooking the beautifully landscaped backyard, and included refrigerator, dishwasher, range, and disposer. A conveniently located half bath completes this level. Upstairs, the primary bedroom offers generously sized closets, accompanied by two additional bedrooms and a full bath. The first lower level expands the home's possibilities with a spacious L-shaped recreation room featuring sliding doors that open directly onto the deck—an ideal space for entertaining, relaxing, hobbies, or creating a comfortable second living area. A half bath and separate laundry room add to the convenience of this level. One of this home's exceptional features is the deck's walkway leading directly to the front of the home, providing convenient private access to the lower level without passing through the main living areas. Steps from the deck lead down to the beautifully landscaped rear yard, creating a peaceful, private oasis for outdoor enjoyment, gardening, or gatherings with family and friends. The additional walkout basement level offers abundant potential for storage, a workshop, or future use to suit your needs. Conveniently located near shopping, parks, walking paths, and a bus route, this home is nestled in an appealing neighborhood with sidewalks. With its flexible floor plan, numerous updates, inviting outdoor spaces, and the freedom of NO HOA, this is a home full of possibilities and one you won't want to miss!

3 Beds ⋅ 3 Baths

PRICE IMPROVEMENT! NO HOA! Close to Route 11, 37, I-81- Space, Flexibility, Updates & a Beautifully Landscaped Backyard! Discover the possibilities in this spacious and versatile townhome offering a unique multi-level floor plan, inviting living spaces, and wonderful outdoor enjoyment. Thoughtful updates include a new roof and heat pump in 2025, a new hot water heater in 2026, and a beautifully remodeled full bath in 2024, making this home an exciting opportunity for its next owner! The main level welcomes you with a bright and cheerful living room featuring hardwood floors, a charming bay window, built-in shelving, and a wood-burning fireplace that creates the perfect setting for cozy evenings. The separate dining room is enhanced by crown molding and chair rail and offers a convenient closet for storing china and linens. The updated kitchen features Corian countertops, a sink overlooking the beautifully landscaped backyard, and included refrigerator, dishwasher, range, and disposer. A conveniently located half bath completes this level. Upstairs, the primary bedroom offers generously sized closets, accompanied by two additional bedrooms and a full bath. The first lower level expands the home's possibilities with a spacious L-shaped recreation room featuring sliding doors that open directly onto the deck—an ideal space for entertaining, relaxing, hobbies, or creating a comfortable second living area. A half bath and separate laundry room add to the convenience of this level. One of this home's exceptional features is the deck's walkway leading directly to the front of the home, providing convenient private access to the lower level without passing through the main living areas. Steps from the deck lead down to the beautifully landscaped rear yard, creating a peaceful, private oasis for outdoor enjoyment, gardening, or gatherings with family and friends. The additional walkout basement level offers abundant potential for storage, a workshop, or future use to suit your needs. Conveniently located near shopping, parks, walking paths, and a bus route, this home is nestled in an appealing neighborhood with sidewalks. With its flexible floor plan, numerous updates, inviting outdoor spaces, and the freedom of NO HOA, this is a home full of possibilities and one you won't want to miss!

802 Appleseed Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$396,190

660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community and it is ready to move in! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

4 Beds ⋅ 4 Baths

660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community and it is ready to move in! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

660 Arden Ct, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

$393,495

652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for November move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

4 Beds ⋅ 4 Baths

652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for November move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

652 Arden Ct, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

$320,000

SHORT SALE! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom upstairs. Enjoy the peace of mind that comes with numerous recent updates and renovations completed in 2024, including architectural shingles, carport soffit, central heating and air conditioning with a dual-zone electric heat pump, crawl space sump pump and poly, and fresh paint throughout. Inside, you’ll find refinished real hardwood floors in the living areas and bedrooms, updated flooring in the kitchen and bathrooms, and numerous updated plumbing and light fixtures, vanities, outlets and switches. The Kitchen and primary bathroom feature a quartz countertop, an undermount sink with beautiful tiled shower with a glass door. This home offers a wonderful opportunity to move right in and enjoy.

3 Beds ⋅ 2 Baths

SHORT SALE! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom upstairs. Enjoy the peace of mind that comes with numerous recent updates and renovations completed in 2024, including architectural shingles, carport soffit, central heating and air conditioning with a dual-zone electric heat pump, crawl space sump pump and poly, and fresh paint throughout. Inside, you’ll find refinished real hardwood floors in the living areas and bedrooms, updated flooring in the kitchen and bathrooms, and numerous updated plumbing and light fixtures, vanities, outlets and switches. The Kitchen and primary bathroom feature a quartz countertop, an undermount sink with beautiful tiled shower with a glass door. This home offers a wonderful opportunity to move right in and enjoy.

2919 S Pleasant Valley Rd, Winchester

Listing courtesy of Keller Williams Realty Dulles. Contact:

$490,000

Opportunity Knocks again. BACK ON THE MARKET. Major benefits/amenities, living within Winchester City Limits. New park being constructed a mile away. A Rare Opportunity with Space, Views & Income Potential! Discover the possibilities at 2643 Middle Road in Winchester! Situated on a .28-acre lot atop high ground, this four-bedroom single-family home offers 2,526 square feet across its top two levels, generously sized rooms, large 2 car garage and spaces for 4 cars in the drive way; add magnificent sunset views! With no HOA, you have greater flexibility to make this property your own. The basement features two separate exterior entrances and existing plumbing for a full bath, offering exciting potential for future living space or possible rental units, subject to applicable zoning, permits, and approvals. Whether you're looking for a spacious home, an opportunity to build equity, or a property with income-producing possibilities, this home deserves your attention. Priced at $490,000, below its $520,600 assessed value, this is an opportunity to bring your vision to life. Imagine the possibilities and schedule your private tour today! Near Shenandoah College, Publix new shopping center and major routes.

4 Beds ⋅ 4 Baths

Opportunity Knocks again. BACK ON THE MARKET. Major benefits/amenities, living within Winchester City Limits. New park being constructed a mile away. A Rare Opportunity with Space, Views & Income Potential! Discover the possibilities at 2643 Middle Road in Winchester! Situated on a .28-acre lot atop high ground, this four-bedroom single-family home offers 2,526 square feet across its top two levels, generously sized rooms, large 2 car garage and spaces for 4 cars in the drive way; add magnificent sunset views! With no HOA, you have greater flexibility to make this property your own. The basement features two separate exterior entrances and existing plumbing for a full bath, offering exciting potential for future living space or possible rental units, subject to applicable zoning, permits, and approvals. Whether you're looking for a spacious home, an opportunity to build equity, or a property with income-producing possibilities, this home deserves your attention. Priced at $490,000, below its $520,600 assessed value, this is an opportunity to bring your vision to life. Imagine the possibilities and schedule your private tour today! Near Shenandoah College, Publix new shopping center and major routes.

2643 Middle Rd, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$515,000

Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square Feet Across Two (2) Levels *Built 1992 *0.23 Acre Lot (Approx. 10,019 Square Feet) *One (1) Car Attached Front-Loading Garage + Paved Driveway *Second Garage Bay Converted to Oversized Main Level Laundry and Storage with Bonus Area Across the Front *Washer and Dryer Convey with the Property *Oversized Front Porch *Fully Fenced Rear Yard *Mature Landscaping *8' x 10' Outside Storage Shed *All Five (5) Bedrooms on the Upper Level *Two (2) Primary Suites *Primary Bathroom with Soaking Garden Tub + Separate Shower *Walk-In Closets *Vaulted Ceiling in Family Room Off the Kitchen *Wood-Burning Fireplace *Crown Moulding *Ceiling Fans *Additional Storage in Floored Attic Space *Updated Kitchen (2020) with Wood Cabinetry, Quartz Countertops and Stainless Steel Appliances *Luxury Vinyl Plank Flooring in Foyer and Kitchen *Architectural Shingle Roof (2009) *Tankless On-Demand Water Heater *Two (2) Zone Heating and Air Conditioning *No Homeowners Association *Cul-de-Sac Setting with No Through Street *Inside the City Limits of Winchester *Winchester City Public School Assignments *Close to Old Town Winchester *Minutes to Winchester Medical Center and the Shenandoah University Health Professions Campus *Convenient to Route 37 and Interstate 81 Commuter Routes.

5 Beds ⋅ 4 Baths

Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square Feet Across Two (2) Levels *Built 1992 *0.23 Acre Lot (Approx. 10,019 Square Feet) *One (1) Car Attached Front-Loading Garage + Paved Driveway *Second Garage Bay Converted to Oversized Main Level Laundry and Storage with Bonus Area Across the Front *Washer and Dryer Convey with the Property *Oversized Front Porch *Fully Fenced Rear Yard *Mature Landscaping *8' x 10' Outside Storage Shed *All Five (5) Bedrooms on the Upper Level *Two (2) Primary Suites *Primary Bathroom with Soaking Garden Tub + Separate Shower *Walk-In Closets *Vaulted Ceiling in Family Room Off the Kitchen *Wood-Burning Fireplace *Crown Moulding *Ceiling Fans *Additional Storage in Floored Attic Space *Updated Kitchen (2020) with Wood Cabinetry, Quartz Countertops and Stainless Steel Appliances *Luxury Vinyl Plank Flooring in Foyer and Kitchen *Architectural Shingle Roof (2009) *Tankless On-Demand Water Heater *Two (2) Zone Heating and Air Conditioning *No Homeowners Association *Cul-de-Sac Setting with No Through Street *Inside the City Limits of Winchester *Winchester City Public School Assignments *Close to Old Town Winchester *Minutes to Winchester Medical Center and the Shenandoah University Health Professions Campus *Convenient to Route 37 and Interstate 81 Commuter Routes.

1605 Fort Braddock Ct, Winchester

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

$700,000

Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. Create wealth with this income producing opportunity. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along with formal living and dining rooms, a warm and inviting family room with fireplace, and a well-equipped kitchen with center island and breakfast area. Hardwood floors and detailed trim work add classic character throughout. A standout feature of this home is the private ground-level apartment with its own entrance—complete with a full kitchen, bedroom, bathroom, living space, and dedicated laundry. Perfect for guests, extended family, or potential rental income. Upstairs, you'll find additional spacious bedrooms and full baths, offering plenty of room for everyone. Enjoy the outdoors from your beautifully landscaped yard with space to garden, entertain, or relax. A two-car garage and extended driveway provide ample parking. Conveniently located just minutes to downtown Winchester, parks, shopping, dining, and commuter routes—this home offers the space and versatility you've been searching for. Priced below appraisal. Schedule your private showing today!

5 Beds ⋅ 5 Baths

Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. Create wealth with this income producing opportunity. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along with formal living and dining rooms, a warm and inviting family room with fireplace, and a well-equipped kitchen with center island and breakfast area. Hardwood floors and detailed trim work add classic character throughout. A standout feature of this home is the private ground-level apartment with its own entrance—complete with a full kitchen, bedroom, bathroom, living space, and dedicated laundry. Perfect for guests, extended family, or potential rental income. Upstairs, you'll find additional spacious bedrooms and full baths, offering plenty of room for everyone. Enjoy the outdoors from your beautifully landscaped yard with space to garden, entertain, or relax. A two-car garage and extended driveway provide ample parking. Conveniently located just minutes to downtown Winchester, parks, shopping, dining, and commuter routes—this home offers the space and versatility you've been searching for. Priced below appraisal. Schedule your private showing today!

769 Seldon Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$304,900

New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter thoroughfares. No HOA.

3 Beds ⋅ 3 Baths

New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter thoroughfares. No HOA.

913 Orchard Hill Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$795,000

Well established, reputable, and long-standing auto service center in a prime location at the intersection of Millwood Avenue and Pleasant Valley Road directly across from Shenandoah University. Presently doing business as Jim’s Auto Service Center. Excellent location, visibility, exposure, and sign location opportunities. Two bay garage doors equipped with two pneumatic lifts, providing new tire sales, tire repairs, batteries, oil changes, lube and filter replacement, fluids, flushing, belts and hoses, brake services, air conditioning services, wheel balancing, frontend alignment and more. The sales price includes the business, long-standing list of loyal customers and specified equipment and tools. Tours by appointment only with the exclusive listing agent. Call agent now for more details.

434 Millwood Ave, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$439,999

Circa 1920 office building in downtown Winchester. Currently used as a lawyer's office, but could easily be an office-and-residential space or a single-family home. Off-street parking.

124 S Braddock St, Winchester

Listing courtesy of Colony Realty. Contact:

$210,000

Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a well-maintained appearance. Whether you're looking to expand your investment portfolio or secure a future owner-occupied residence, this property presents a great opportunity. A tenant is currently in place through November 8, 2026, paying below market value, with potential for future rent increases. Enjoy immediate rental income and long-term upside in a sought-after location.

3 Beds ⋅ 1 Baths

Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a well-maintained appearance. Whether you're looking to expand your investment portfolio or secure a future owner-occupied residence, this property presents a great opportunity. A tenant is currently in place through November 8, 2026, paying below market value, with potential for future rent increases. Enjoy immediate rental income and long-term upside in a sought-after location.

405 Shenandoah Ave, Winchester

Listing courtesy of Samson Properties. Contact:

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