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Move-in ready home in the highly sought-after Orchard Hills community! This well-maintained property offers peace of mind with major updates already completed, including a new roof, gutters, and gutter guards (2018), new HVAC/furnace system (2024), new water heater (2024), and freshly painted exterior window trim, shutters, and additional trim (2021). Additional features include attic with storage space and convenient pull-down stairs, a storage shed, a stamped concrete patio, and more. EV Car Charger conveys. Also, tall crawlspace for some extra storage. You’ll love the off-street parking, spacious backyard, and beautiful stamped concrete patio, perfect for relaxing or entertaining in a private, wooded setting. The raised garden beds make it easy to grow your favorite vegetables or plantings of choice. Check out our 3-D Tour attached to this listing!

2165 Harvest Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$300,000

Charming Rancher on Butler Avenue — This home is ready for its next owner! Nestled on a quiet street that ends in a cul-de-sac, you’ll enjoy peace and convenience of living on this east-side locations. Just steps to Virginia Avenue Elementary, parks, and Wesley Church, and only minutes to Historic Old Town Winchester’s shopping and restaurants. Commuters will appreciate the quick access to Route 7 and I-81. Step inside to a welcoming living room that flows into the open kitchen and dining area—perfect for gathering around the table. Off the kitchen, you’ll be pleasantly surprised by the spacious family room, offering plenty of room to relax or entertain. A back addition features a versatile laundry room/bonus room with walk-out access to the concrete back patio and a generously sized owner’s suite with a private full bath. Down the main hallway, you’ll find three additional bedrooms and a full hall bath. While some may wish to make cosmetic updates such as new carpet, paint, or lighting (note: there are no hardwoods beneath the carpet), the home is move-in ready and full of potential. Enjoy central air conditioning, a fenced backyard with a handy storage shed or workshop, and a new roof for peace of mind. Built in 1968, this rancher offers the solid construction and vintage character you’ll love—with room to add your personal touch. Sold as is but well-cared-for, this gem on Butler Avenue is ready for you to make it your own and continue the story of a home that’s been loved for decades.

Charming Rancher on Butler Avenue — This home is ready for its next owner! Nestled on a quiet street that ends in a cul-de-sac, you’ll enjoy peace and convenience of living on this east-side locations. Just steps to Virginia Avenue Elementary, parks, and Wesley Church, and only minutes to Historic Old Town Winchester’s shopping and restaurants. Commuters will appreciate the quick access to Route 7 and I-81. Step inside to a welcoming living room that flows into the open kitchen and dining area—perfect for gathering around the table. Off the kitchen, you’ll be pleasantly surprised by the spacious family room, offering plenty of room to relax or entertain. A back addition features a versatile laundry room/bonus room with walk-out access to the concrete back patio and a generously sized owner’s suite with a private full bath. Down the main hallway, you’ll find three additional bedrooms and a full hall bath. While some may wish to make cosmetic updates such as new carpet, paint, or lighting (note: there are no hardwoods beneath the carpet), the home is move-in ready and full of potential. Enjoy central air conditioning, a fenced backyard with a handy storage shed or workshop, and a new roof for peace of mind. Built in 1968, this rancher offers the solid construction and vintage character you’ll love—with room to add your personal touch. Sold as is but well-cared-for, this gem on Butler Avenue is ready for you to make it your own and continue the story of a home that’s been loved for decades.

621 Butler Ave, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Five Star Real Estate.

$320,000

Nestled in Orchard Terrace, this beautifully updated Colonial offers 4 bedrooms, 2 baths ideally located within Winchester city limits just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen has brand new granite countertops and stainless steel appliances. Enjoy fresh new paint throughout, new luxury vinyl plank flooring on the main level and new carpet upstairs. Exterior upgrades include new shutters, front porch railing and steps. Washer/Dryer conveys (as-is); 20X32 Large metal building (as-is). Seller is willing to contribute a maximum of $5,000 toward buyer concessions with an acceptable offer *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

Nestled in Orchard Terrace, this beautifully updated Colonial offers 4 bedrooms, 2 baths ideally located within Winchester city limits just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen has brand new granite countertops and stainless steel appliances. Enjoy fresh new paint throughout, new luxury vinyl plank flooring on the main level and new carpet upstairs. Exterior upgrades include new shutters, front porch railing and steps. Washer/Dryer conveys (as-is); 20X32 Large metal building (as-is). Seller is willing to contribute a maximum of $5,000 toward buyer concessions with an acceptable offer *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

700 Watson Ave, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Charis Realty Group.

$580,000

Perfectly poised on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2.5-bathroom home offers both seclusion and incredible proximity to Winchester's finest amenities, schools, shopping, and major commuter routes. This residence has been completely reimagined, blending the enduring strength of all-brick construction with bespoke, high-end modern finishes. The moment you enter, you are greeted by the seamless flow of newer, wide-plank LVP flooring that extends throughout, complemented by designer-selected, upgraded light fixtures that cast a warm, ambient glow. The heart of the home is the gourmet chef's kitchen, a true culinary sanctuary. It features sleek, upgraded counters, stunning subway tile walls, open floating shelves for display, and a massive center island that serves as the perfect gathering spot. Outfitted with a suite of newer, top-tier appliances, this space is designed for both grand entertaining and intimate dining. The adjacent main level living area provides warmth and ambiance with a wood-burning fireplace, an ideal setting for cozy evenings. The main level also encompasses three spacious bedrooms and a convenient 1.5 bath setup. The spa-like ensuite primary bath is appointed with sinks for two, exquisite custom tile work and is anchored by an impressive glass-enclosed shower. You can enjoy peace of mind knowing that every bath in the home has been newly renovated and finished to the same superior standard of modern luxury. A truly exceptional feature is the fully-finished, walkout lower level, offering an incredible extension of living space. This level includes two additional bedrooms, a pristine full bathroom, and a highly functional laundry command center featuring extensive counter space, custom cabinetry, and a utility sink—elevating laundry from a chore to a convenience. The exterior of the property seamlessly transforms into your exclusive private retreat. The presence is enhanced by the circular driveway, ensuring generous off-street parking for residents and guests. The outdoor space offers a large screened-in porch ideal for bug-free relaxation, and a versatile lower paved patio for gatherings. For elevated functionality and architectural interest, a spiral staircase descends gracefully from the upper deck to the lower level. Completing the luxury amenities, a relaxing hot tub awaits, offering the ultimate sanctuary for year-round indulgence. An added shed provides discreet storage for tools and equipment. Offering perfection around every corner, this is a turn-key residence where the finest materials and thoughtful design converge. Your elevated Winchester lifestyle begins here.

5 Beds ⋅ 3 Baths

Perfectly poised on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2.5-bathroom home offers both seclusion and incredible proximity to Winchester's finest amenities, schools, shopping, and major commuter routes. This residence has been completely reimagined, blending the enduring strength of all-brick construction with bespoke, high-end modern finishes. The moment you enter, you are greeted by the seamless flow of newer, wide-plank LVP flooring that extends throughout, complemented by designer-selected, upgraded light fixtures that cast a warm, ambient glow. The heart of the home is the gourmet chef's kitchen, a true culinary sanctuary. It features sleek, upgraded counters, stunning subway tile walls, open floating shelves for display, and a massive center island that serves as the perfect gathering spot. Outfitted with a suite of newer, top-tier appliances, this space is designed for both grand entertaining and intimate dining. The adjacent main level living area provides warmth and ambiance with a wood-burning fireplace, an ideal setting for cozy evenings. The main level also encompasses three spacious bedrooms and a convenient 1.5 bath setup. The spa-like ensuite primary bath is appointed with sinks for two, exquisite custom tile work and is anchored by an impressive glass-enclosed shower. You can enjoy peace of mind knowing that every bath in the home has been newly renovated and finished to the same superior standard of modern luxury. A truly exceptional feature is the fully-finished, walkout lower level, offering an incredible extension of living space. This level includes two additional bedrooms, a pristine full bathroom, and a highly functional laundry command center featuring extensive counter space, custom cabinetry, and a utility sink—elevating laundry from a chore to a convenience. The exterior of the property seamlessly transforms into your exclusive private retreat. The presence is enhanced by the circular driveway, ensuring generous off-street parking for residents and guests. The outdoor space offers a large screened-in porch ideal for bug-free relaxation, and a versatile lower paved patio for gatherings. For elevated functionality and architectural interest, a spiral staircase descends gracefully from the upper deck to the lower level. Completing the luxury amenities, a relaxing hot tub awaits, offering the ultimate sanctuary for year-round indulgence. An added shed provides discreet storage for tools and equipment. Offering perfection around every corner, this is a turn-key residence where the finest materials and thoughtful design converge. Your elevated Winchester lifestyle begins here.

553 Bellview Ave, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Realty ONE Group Old Towne.

$395,000

Charming Rancher In Winchester, VA! Beautifully updated 4-bedroom, 2 full bath home offers both comfort and functionality. Fully finished basement ALSO includes a spacious 12x28 workshop with walk-out level to fenced rear yard—yard extends beyond the fence line! NEW gas furnace and NEW gas water heater just installed for new homeowner. Gorgeous hardwood floors throughout main level, newer windows, updated kitchen & appliances with luxury plank tile flooring in the kitchen. 3 Bedrooms, 1 full bath on main level with a jetted tub/shower combo. 4th bedroom and 2nd full bath on lower level. Large shed conveys along with riding lawn mower. So much to love about this home—schedule your tour today and be in for the holidays!

Charming Rancher In Winchester, VA! Beautifully updated 4-bedroom, 2 full bath home offers both comfort and functionality. Fully finished basement ALSO includes a spacious 12x28 workshop with walk-out level to fenced rear yard—yard extends beyond the fence line! NEW gas furnace and NEW gas water heater just installed for new homeowner. Gorgeous hardwood floors throughout main level, newer windows, updated kitchen & appliances with luxury plank tile flooring in the kitchen. 3 Bedrooms, 1 full bath on main level with a jetted tub/shower combo. 4th bedroom and 2nd full bath on lower level. Large shed conveys along with riding lawn mower. So much to love about this home—schedule your tour today and be in for the holidays!

461 Imperial St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Oasys Realty.

$695,000

From the moment you arrive, this home welcomes you in. A spacious covered front porch—perfect for rocking chairs and quiet mornings—sets the stage for the warmth and comfort that await inside. Step through the front door into an open foyer, where a formal living room sits to the left and a stately office with French doors lies to the right. At the heart of the home, the kitchen features granite counters, an eat-in breakfast area that opens to the deck, and a formal dining room ideal for hosting gatherings. The largey family room, anchored by a cozy fireplace, provides the perfect backdrop for both everyday living and special occasions. The main level is completed by a convenient half bath and a dedicated laundry room. Two separate staircases lead to the expansive upper level. The primary suite boasts dual walk-in closets and a luxurious ensuite bath with dual vanities, a soaking tub, tiled shower, and private water closet. A full hall bath serves the guest bedroom, while a Jack-and-Jill bath connects two additional bedrooms—ensuring both comfort and convenience. The finished basement offers endless possibilities, including a spacious recreation area, a full bathroom, and a large unfinished storage room. From here, step out to a sprawling brick patio overlooking a private backyard oasis—nearly half an acre of space for relaxing, playing, or entertaining. Enjoy a lush, green yard year-round with the programmable irrigation system. Nestled at the end of a quiet cul-de-sac and backing to protected wetlands and a serene nature preserve, this home blends privacy, elegance, and functionality. With more than 5,000 sq. ft. of living space, it’s the perfect place to create lasting memories.

4 Beds ⋅ 5 Baths

From the moment you arrive, this home welcomes you in. A spacious covered front porch—perfect for rocking chairs and quiet mornings—sets the stage for the warmth and comfort that await inside. Step through the front door into an open foyer, where a formal living room sits to the left and a stately office with French doors lies to the right. At the heart of the home, the kitchen features granite counters, an eat-in breakfast area that opens to the deck, and a formal dining room ideal for hosting gatherings. The largey family room, anchored by a cozy fireplace, provides the perfect backdrop for both everyday living and special occasions. The main level is completed by a convenient half bath and a dedicated laundry room. Two separate staircases lead to the expansive upper level. The primary suite boasts dual walk-in closets and a luxurious ensuite bath with dual vanities, a soaking tub, tiled shower, and private water closet. A full hall bath serves the guest bedroom, while a Jack-and-Jill bath connects two additional bedrooms—ensuring both comfort and convenience. The finished basement offers endless possibilities, including a spacious recreation area, a full bathroom, and a large unfinished storage room. From here, step out to a sprawling brick patio overlooking a private backyard oasis—nearly half an acre of space for relaxing, playing, or entertaining. Enjoy a lush, green yard year-round with the programmable irrigation system. Nestled at the end of a quiet cul-de-sac and backing to protected wetlands and a serene nature preserve, this home blends privacy, elegance, and functionality. With more than 5,000 sq. ft. of living space, it’s the perfect place to create lasting memories.

1877 Clayton Ridge Dr, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Colony Realty.

$675,000

Classic Stone Cape Cod Charm Meets Modern Luxury This stunning, remodeled 1940s Stone Cape Cod offers the perfect blend of timeless architecture and contemporary comfort on one of Winchester's most coveted, quiet neighborhood streets. Enjoy the unique lifestyle of being walkable to vibrant downtown, all while relaxing in your own almost half-acre, garden oasis. Step inside to discover a home meticulously updated home. The refinished hardwood flooring and an abundance of natural light lead you through a classic Better Homes and Gardens floor plan, now complemented by upgraded light fixtures and a remodeled powder room. The living room features a beautiful custom-made fireplace mantle with a gas insert, creating a perfect space for cozy evenings. The newly carpeted lower level transforms into a flexible and inviting retreat, perfect for a media room, play space, and dedicated home theater. Practicality meets style with luxury vinyl plank flooring seamlessly installed in the full bath and laundry areas. The true magic continues outside. The property features lush Japanese gardens and serene walking paths, all framed by elegant flagstone walkways in the front and a charming stone wall in the fully fenced backyard. Ideal for entertaining, the back boasts an expansive patio with a covered 16x13 porch—a private retreat for summer gatherings. Significant upgrades ensure low-maintenance living: new windows, siding, 6-inch gutters, fascia, and a new storm door. This fully repainted home also comes equipped with a security system and cameras for peace of mind. Your own private driveway with parking for 4 cars. Don't miss the opportunity to own this turn-key piece of Winchester history. Schedule your private viewing today! LISITNG AGENT OWNER

Classic Stone Cape Cod Charm Meets Modern Luxury This stunning, remodeled 1940s Stone Cape Cod offers the perfect blend of timeless architecture and contemporary comfort on one of Winchester's most coveted, quiet neighborhood streets. Enjoy the unique lifestyle of being walkable to vibrant downtown, all while relaxing in your own almost half-acre, garden oasis. Step inside to discover a home meticulously updated home. The refinished hardwood flooring and an abundance of natural light lead you through a classic Better Homes and Gardens floor plan, now complemented by upgraded light fixtures and a remodeled powder room. The living room features a beautiful custom-made fireplace mantle with a gas insert, creating a perfect space for cozy evenings. The newly carpeted lower level transforms into a flexible and inviting retreat, perfect for a media room, play space, and dedicated home theater. Practicality meets style with luxury vinyl plank flooring seamlessly installed in the full bath and laundry areas. The true magic continues outside. The property features lush Japanese gardens and serene walking paths, all framed by elegant flagstone walkways in the front and a charming stone wall in the fully fenced backyard. Ideal for entertaining, the back boasts an expansive patio with a covered 16x13 porch—a private retreat for summer gatherings. Significant upgrades ensure low-maintenance living: new windows, siding, 6-inch gutters, fascia, and a new storm door. This fully repainted home also comes equipped with a security system and cameras for peace of mind. Your own private driveway with parking for 4 cars. Don't miss the opportunity to own this turn-key piece of Winchester history. Schedule your private viewing today! LISITNG AGENT OWNER

316 W Whitlock Ave, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: Roberts Realty Group, LLC.

$418,000

Now $450,000 — Motivated Sellers + Huge Monthly Savings with 2-1 Rate Buydown! Step inside this beautifully restored 4-bedroom, 2.5-bath 1920s home and experience where historic charm meets modern luxury. Offering over 2,200 sq ft across three finished levels, 580 N Braddock delivers light, space, and thoughtful design—just blocks from Old Town Winchester’s walking mall. The main level features wide-plank flooring, a cozy gas fireplace, and a showpiece kitchen with a massive island, stainless steel appliances, and a gas range. Two versatile rooms on the main (bedroom, office, or playroom), a full bath, powder room, and convenient laundry add flexibility. Upstairs, two additional bedrooms and a beautifully updated full bath complete the home. Every major system is new—roof, siding, plumbing, wiring, dual-zone HVAC. Outside, enjoy covered front and rear porches, a charming “she shed” or storage space, playground, and off-street parking for four. Full unfinished basement offers excellent storage or expansion potential. 💥 SELLER INCENTIVES — ACT NOW! The sellers are highly motivated and have launched a special Inventory Reduction Program: Option 1: Price reduced to $450,000 — immediate equity and value. Option 2: Take advantage of a 2-1 Interest Rate Buydown, saving you over $600 per month in the first year alone! (Available on Conventional, FHA, VA, and USDA loans.) Combined with closing cost assistance and flexible terms, this home is positioned to move now. The nearby historic apple warehouse is slated for adaptive reuse under Winchester’s redevelopment plans—expected to bring new residential and retail life to this area, adding long-term appeal to your investment. Your next home is beautiful, move-in ready, and more affordable than ever. Don’t wait—schedule your private showing today.

Now $450,000 — Motivated Sellers + Huge Monthly Savings with 2-1 Rate Buydown! Step inside this beautifully restored 4-bedroom, 2.5-bath 1920s home and experience where historic charm meets modern luxury. Offering over 2,200 sq ft across three finished levels, 580 N Braddock delivers light, space, and thoughtful design—just blocks from Old Town Winchester’s walking mall. The main level features wide-plank flooring, a cozy gas fireplace, and a showpiece kitchen with a massive island, stainless steel appliances, and a gas range. Two versatile rooms on the main (bedroom, office, or playroom), a full bath, powder room, and convenient laundry add flexibility. Upstairs, two additional bedrooms and a beautifully updated full bath complete the home. Every major system is new—roof, siding, plumbing, wiring, dual-zone HVAC. Outside, enjoy covered front and rear porches, a charming “she shed” or storage space, playground, and off-street parking for four. Full unfinished basement offers excellent storage or expansion potential. 💥 SELLER INCENTIVES — ACT NOW! The sellers are highly motivated and have launched a special Inventory Reduction Program: Option 1: Price reduced to $450,000 — immediate equity and value. Option 2: Take advantage of a 2-1 Interest Rate Buydown, saving you over $600 per month in the first year alone! (Available on Conventional, FHA, VA, and USDA loans.) Combined with closing cost assistance and flexible terms, this home is positioned to move now. The nearby historic apple warehouse is slated for adaptive reuse under Winchester’s redevelopment plans—expected to bring new residential and retail life to this area, adding long-term appeal to your investment. Your next home is beautiful, move-in ready, and more affordable than ever. Don’t wait—schedule your private showing today.

580 N Braddock St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Re/Max Roots.

$297,900

Welcome home to this charming 2-bedroom Craftsman-style home! Take a few steps up to this adorable downtown pad. Inside, you’ll find a warm and comfortable interior filled with character, including beautiful refinished hardwood floors, built-ins in the living room, and a built-in china cabinet in the dining room. The newly remodeled kitchen features newer appliances, while the furnace and AC are approximately 2.5 years old. Upstairs offers two bedrooms, a fully remodeled bathroom, a walk-in closet, and two cozy built-in desks—perfect for a small office or study nook. Step outside to enjoy the well-maintained patio with privacy fencing, with a low-maintenance yard, or relax on the inviting covered front porch. Plenty of street parking. Freshly painted inside and out with designer paint, with all-new fencing, this home is truly move-in ready. Conveniently located just a block and a half away from Old Town Winchester and close to all amenities, it’s the perfect spot for anyone looking to enjoy both comfort and convenience.

2 Beds ⋅ 2 Baths

Welcome home to this charming 2-bedroom Craftsman-style home! Take a few steps up to this adorable downtown pad. Inside, you’ll find a warm and comfortable interior filled with character, including beautiful refinished hardwood floors, built-ins in the living room, and a built-in china cabinet in the dining room. The newly remodeled kitchen features newer appliances, while the furnace and AC are approximately 2.5 years old. Upstairs offers two bedrooms, a fully remodeled bathroom, a walk-in closet, and two cozy built-in desks—perfect for a small office or study nook. Step outside to enjoy the well-maintained patio with privacy fencing, with a low-maintenance yard, or relax on the inviting covered front porch. Plenty of street parking. Freshly painted inside and out with designer paint, with all-new fencing, this home is truly move-in ready. Conveniently located just a block and a half away from Old Town Winchester and close to all amenities, it’s the perfect spot for anyone looking to enjoy both comfort and convenience.

129 E Cork St, Winchester

Listing courtesy of Sager Real Estate. Contact:

Selling Office: Coldwell Banker Premier.

$529,000

A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet kitchen with brand new state of art appliances includes wine fridge, drawer style microwave, and pot filler. Formal living/dining room(s). Extras include den, office(s), nooks, and 3rd floor bonus room (perfect for kid's getaway). Laundry hook-ups on both main level and 2nd level. This home has been tastefully remodeled with gorgeous modern upgrades without disturbing the charm and character that has been so carefully preserved. Exposed log, brick, built-ins, and original wood flooring are just some of the timeless details. Outside you will find a large stately courtyard complete with stone patio, brick walkways, and deck. Fully fenced rear yard. Situated on the Apple Blossom parade route in downtown Winchester, seconds from the walking mall.

A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet kitchen with brand new state of art appliances includes wine fridge, drawer style microwave, and pot filler. Formal living/dining room(s). Extras include den, office(s), nooks, and 3rd floor bonus room (perfect for kid's getaway). Laundry hook-ups on both main level and 2nd level. This home has been tastefully remodeled with gorgeous modern upgrades without disturbing the charm and character that has been so carefully preserved. Exposed log, brick, built-ins, and original wood flooring are just some of the timeless details. Outside you will find a large stately courtyard complete with stone patio, brick walkways, and deck. Fully fenced rear yard. Situated on the Apple Blossom parade route in downtown Winchester, seconds from the walking mall.

121 N Washington St, Winchester

Listing courtesy of Re/Max Roots. Contact:

Selling Office: RE/MAX Roots.

$583,300

Income-Producing Duplex in Prime Winchester Location – Unique Investment Opportunity! Just two blocks south of Old Town Winchester’s Walking Mall, this charming duplex sits on a quiet residential street—offering the best of both location and lifestyle. With a strong rental history and over $54,000 in rental income in 2024, this property delivers a solid 6% cap rate, making it an ideal opportunity for both investors and owner-occupants. It is rented short term (13 – 26 weeks) to traveling medical professionals. Both units come fully furnished. The property features two well-maintained units: Unit 1: 2 Bedrooms | 2 Bathrooms | Direct Walkout Basement. Unit 2: 2 Bedrooms | 1 Bathroom. Both units include: Spacious living rooms, formal dining areas, and full kitchens. Finished third-floor bonus spaces—perfect for offices, guest rooms, or play areas. Beautiful hardwood floors throughout. Front and side porches offering private outdoor spaces. Full, private, unfinished basements with laundry—ample storage or future finishing potential. With four years of verifiable rental income, this turnkey property offers flexibility: live in one unit and rent the other or continue renting both for maximum returns. The 2-bed/2-bath unit’s walkout basement provides added value and accessibility. Don’t miss your chance to own a rare, income-producing property in the heart of Winchester—location, charm, and cash flow all in one.

Income-Producing Duplex in Prime Winchester Location – Unique Investment Opportunity! Just two blocks south of Old Town Winchester’s Walking Mall, this charming duplex sits on a quiet residential street—offering the best of both location and lifestyle. With a strong rental history and over $54,000 in rental income in 2024, this property delivers a solid 6% cap rate, making it an ideal opportunity for both investors and owner-occupants. It is rented short term (13 – 26 weeks) to traveling medical professionals. Both units come fully furnished. The property features two well-maintained units: Unit 1: 2 Bedrooms | 2 Bathrooms | Direct Walkout Basement. Unit 2: 2 Bedrooms | 1 Bathroom. Both units include: Spacious living rooms, formal dining areas, and full kitchens. Finished third-floor bonus spaces—perfect for offices, guest rooms, or play areas. Beautiful hardwood floors throughout. Front and side porches offering private outdoor spaces. Full, private, unfinished basements with laundry—ample storage or future finishing potential. With four years of verifiable rental income, this turnkey property offers flexibility: live in one unit and rent the other or continue renting both for maximum returns. The 2-bed/2-bath unit’s walkout basement provides added value and accessibility. Don’t miss your chance to own a rare, income-producing property in the heart of Winchester—location, charm, and cash flow all in one.

10-12 W Cecil St, Winchester

Listing courtesy of Cottage Street Realty LLC. Contact:

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

$415,000

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

290 Green St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Cuzzi Realty, Inc..

$334,900

2225 Harrison Street located in Winchester, VA. One level living in a home remodeled in the fall of 2023. This property is well suited for any living situation. Perfect for a first time home buyer or someone looking to downsize. Granite countertops and stainless steel appliances complement the kitchen. The primary bedroom with an en suite is the perfect getaway. Call today for your private showing. All measurements are approximate. Call today for your private showing.

2225 Harrison Street located in Winchester, VA. One level living in a home remodeled in the fall of 2023. This property is well suited for any living situation. Perfect for a first time home buyer or someone looking to downsize. Granite countertops and stainless steel appliances complement the kitchen. The primary bedroom with an en suite is the perfect getaway. Call today for your private showing. All measurements are approximate. Call today for your private showing.

2225 Harrison St, Winchester

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

This beautiful home in Willow Lawn Cottages has been freshly painted, professionally cleaned and lovingly prepared just for you. Step inside to find rich wooden floors, vaulted ceilings, and a cozy fireplace that immediately make you feel at home. Imagine arranging your favorite furniture in bright, airy rooms filled with natural light. One of the largest floor plans in the neighborhood, this home offers a spacious primary suite with a walk-in closet and private bath, a sunroom that's perfect for morning coffee, and a flexible den that could serve as a dining room, office, or music room. A generous second bedroom - complete with its own large walk-in closet- adds comfort and space for guests. The open kitchen, dining area, and living room share dramatic vaulted ceilings that make the home feel even more open and welcoming. Step outside and enjoy the mature landscaping thorough out this peaceful 55+ community. Stroll along sidewalks that lead to the community center, where neighbors gather for events and activities, or simply relax knowing the HOA handles lawn care and snow removal—leaving you free to spend your time doing what you love. With a prime location close to the hospital, restaurants, and grocery stores, Willow Lawn Cottages offers the perfect blend of comfort, convenience, and connection. Whether you’re hosting friends in your sunroom or taking an evening walk through tree-lined streets, you’ll quickly see why so many love calling this community home.

$385,000

2 Beds ⋅ 2 Baths

This beautiful home in Willow Lawn Cottages has been freshly painted, professionally cleaned and lovingly prepared just for you. Step inside to find rich wooden floors, vaulted ceilings, and a cozy fireplace that immediately make you feel at home. Imagine arranging your favorite furniture in bright, airy rooms filled with natural light. One of the largest floor plans in the neighborhood, this home offers a spacious primary suite with a walk-in closet and private bath, a sunroom that's perfect for morning coffee, and a flexible den that could serve as a dining room, office, or music room. A generous second bedroom - complete with its own large walk-in closet- adds comfort and space for guests. The open kitchen, dining area, and living room share dramatic vaulted ceilings that make the home feel even more open and welcoming. Step outside and enjoy the mature landscaping thorough out this peaceful 55+ community. Stroll along sidewalks that lead to the community center, where neighbors gather for events and activities, or simply relax knowing the HOA handles lawn care and snow removal—leaving you free to spend your time doing what you love. With a prime location close to the hospital, restaurants, and grocery stores, Willow Lawn Cottages offers the perfect blend of comfort, convenience, and connection. Whether you’re hosting friends in your sunroom or taking an evening walk through tree-lined streets, you’ll quickly see why so many love calling this community home.

1823 Kershaw Ln, Winchester

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

Selling Office: MarketPlace REALTY.

$349,000

Introducing this thoughtfully-updated 3-bedroom, 1-full bath brick rancher offering true turnkey living in a highly desirable location! Featuring modern upgrades and a partially finished basement, this home provides comfort and style. The centralized location is incredibly convenient, situated just steps from Daniel Morgan Middle School and only minutes from all the shopping, dining, parks, and amenities that downtown Winchester has to offer. Enter easily via keyless entry and discover a main level that shines with fresh paint, new LVP flooring, and updated light fixtures and hardware. Enjoy privacy with new accordion blinds throughout and blackout blinds in the bedrooms. The living room is cozy and inviting, centered around a wood-burning fireplace. You'll love the updated kitchen boasting new Whirlpool stainless appliances, soft-close cabinets with crown molding, quartz counters, and a sleek subway tile backsplash. The full bath complements the modern feel of the home, featuring new flooring, a new vanity & medicine cabinet, and updated fixtures. Outside, enjoy the spacious deck, a fenced-in yard with newer fencing, a large shed for storage, and well-manicured landscaping and mulched beds. Peace of mind is ensured with a new roof, freshly painted shutters, and new gutter guards. This is a must-see property offering modern convenience and a prime setting.

3 Beds ⋅ 1 Baths

Introducing this thoughtfully-updated 3-bedroom, 1-full bath brick rancher offering true turnkey living in a highly desirable location! Featuring modern upgrades and a partially finished basement, this home provides comfort and style. The centralized location is incredibly convenient, situated just steps from Daniel Morgan Middle School and only minutes from all the shopping, dining, parks, and amenities that downtown Winchester has to offer. Enter easily via keyless entry and discover a main level that shines with fresh paint, new LVP flooring, and updated light fixtures and hardware. Enjoy privacy with new accordion blinds throughout and blackout blinds in the bedrooms. The living room is cozy and inviting, centered around a wood-burning fireplace. You'll love the updated kitchen boasting new Whirlpool stainless appliances, soft-close cabinets with crown molding, quartz counters, and a sleek subway tile backsplash. The full bath complements the modern feel of the home, featuring new flooring, a new vanity & medicine cabinet, and updated fixtures. Outside, enjoy the spacious deck, a fenced-in yard with newer fencing, a large shed for storage, and well-manicured landscaping and mulched beds. Peace of mind is ensured with a new roof, freshly painted shutters, and new gutter guards. This is a must-see property offering modern convenience and a prime setting.

96 Molden Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: RE/MAX Roots.

$450,000

Welcome to 609 Crystal Court, a beautifully maintained, move-in-ready home that perfectly blends modern updates, cozy comfort, and a friendly feel. Nestled in a quiet cul-de-sac just minutes from historic downtown Winchester, this property offers both tranquility and convenience. Inside, you’ll find bright, open living spaces with 9 ft ceilings on the lower level, contemporary finishes that make everyday living effortless. The updated kitchen shines with modern appliances and ample counter space, flowing easily into the dining and family areas - ideal for gatherings or quiet evenings at home. The home features 4 bedrooms and 2.5 baths, each designed for comfort and style. Custom built ins offer so much storage throughout the home. Step outside to a private backyard retreat perfect for morning coffee, weekend barbecues, or kids at play. Recent updates and seller-addressed inspection improvements give buyers added peace of mind, ensuring the home is ready for its next chapter. Located moments from the upcoming Ward Plaza redevelopment, you’ll be near Winchester’s newest dining and shopping destinations while enjoying the calm of an established neighborhood. Don’t miss your chance to own a move-in-ready home that combines modern living, warmth, and an unbeatable location. Schedule your showing today.

Welcome to 609 Crystal Court, a beautifully maintained, move-in-ready home that perfectly blends modern updates, cozy comfort, and a friendly feel. Nestled in a quiet cul-de-sac just minutes from historic downtown Winchester, this property offers both tranquility and convenience. Inside, you’ll find bright, open living spaces with 9 ft ceilings on the lower level, contemporary finishes that make everyday living effortless. The updated kitchen shines with modern appliances and ample counter space, flowing easily into the dining and family areas - ideal for gatherings or quiet evenings at home. The home features 4 bedrooms and 2.5 baths, each designed for comfort and style. Custom built ins offer so much storage throughout the home. Step outside to a private backyard retreat perfect for morning coffee, weekend barbecues, or kids at play. Recent updates and seller-addressed inspection improvements give buyers added peace of mind, ensuring the home is ready for its next chapter. Located moments from the upcoming Ward Plaza redevelopment, you’ll be near Winchester’s newest dining and shopping destinations while enjoying the calm of an established neighborhood. Don’t miss your chance to own a move-in-ready home that combines modern living, warmth, and an unbeatable location. Schedule your showing today.

609 Crystal Ct, Winchester

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

Selling Office: TTR Sotheby's International Realty.

$340,000

Welcome to 301 Liberty Ave, FALL IN LOVE with this charming all brick colonial residence situated in the heart of downtown Winchester. Just blocks away from the scenic walking mall you’ll discover an array of quaint shops, restaurants and the renowned Apple Blossom Parade route. This meticulously fully remodeled home boasts three spacious bedrooms and two luxurious bathrooms and is ready for a new family to create memories in. In 2025 this beauty has a new roof, new windows and gutters. It has all new mechanicals (100% new electrical, plumbing; including the sewer line out to the road, new HVAC, and the list goes on. The main living area features a warm living room; with a farmhouse-style ceiling fan and recessed lighting throughout the main floor. A versatile main-level bedroom, adorned with stunning light fixtures, can seamlessly function as an office, playroom, or gaming room. The main level also includes a beautifully appointed full bathroom with a striking stand-up shower featuring black-and-white tile that extends to the ceiling, evoking a spa-like ambiance. The open-concept kitchen is the heart of the home, showcasing high-end solid wood soft close cabinets with tongue-and-groove detailing, expansive quartz countertops in Calcutta Serenity Blue, and an elegant copper farmhouse sink; great for preparing a meal or hosting a dinner party. Additional highlights include a striking herringbone design backsplash, new stainless steel appliances, and ample recessed lighting. Upstairs you’ll find two bedrooms, a full bathroom with uniform tile design on floors and tub walls; a double-bowl sink along with a spacious linen closet. This house features an upstairs laundry room, no more having to go up and down to do laundry. An adorable nook with floating shelves provides the perfect spot for family photos. The exterior boasts a beautifully remodeled front porch, covered side porch, and delightful brick patio area perfect for relaxing and outdoor entertaining. A newly paved double-wide driveway and underground seamless guttering system ensure functionality and durability along with on street parking. The spacious, fully fenced backyard offers endless possibilities, including a solid brick shed for storage and gardening needs. The yard has ample space for a firepit, hosting get-togethers, a garden or even having kids to play or pets to run around. This home exudes exceptional peace and quiet and thanks to thoughtful landscaping and strategic design, gives you the feel of a private oasis. Inside, enjoy a serene ambience that defies expectations for in-town living.The house has a full unfinished basement for extra storage and possible expansion.

Welcome to 301 Liberty Ave, FALL IN LOVE with this charming all brick colonial residence situated in the heart of downtown Winchester. Just blocks away from the scenic walking mall you’ll discover an array of quaint shops, restaurants and the renowned Apple Blossom Parade route. This meticulously fully remodeled home boasts three spacious bedrooms and two luxurious bathrooms and is ready for a new family to create memories in. In 2025 this beauty has a new roof, new windows and gutters. It has all new mechanicals (100% new electrical, plumbing; including the sewer line out to the road, new HVAC, and the list goes on. The main living area features a warm living room; with a farmhouse-style ceiling fan and recessed lighting throughout the main floor. A versatile main-level bedroom, adorned with stunning light fixtures, can seamlessly function as an office, playroom, or gaming room. The main level also includes a beautifully appointed full bathroom with a striking stand-up shower featuring black-and-white tile that extends to the ceiling, evoking a spa-like ambiance. The open-concept kitchen is the heart of the home, showcasing high-end solid wood soft close cabinets with tongue-and-groove detailing, expansive quartz countertops in Calcutta Serenity Blue, and an elegant copper farmhouse sink; great for preparing a meal or hosting a dinner party. Additional highlights include a striking herringbone design backsplash, new stainless steel appliances, and ample recessed lighting. Upstairs you’ll find two bedrooms, a full bathroom with uniform tile design on floors and tub walls; a double-bowl sink along with a spacious linen closet. This house features an upstairs laundry room, no more having to go up and down to do laundry. An adorable nook with floating shelves provides the perfect spot for family photos. The exterior boasts a beautifully remodeled front porch, covered side porch, and delightful brick patio area perfect for relaxing and outdoor entertaining. A newly paved double-wide driveway and underground seamless guttering system ensure functionality and durability along with on street parking. The spacious, fully fenced backyard offers endless possibilities, including a solid brick shed for storage and gardening needs. The yard has ample space for a firepit, hosting get-togethers, a garden or even having kids to play or pets to run around. This home exudes exceptional peace and quiet and thanks to thoughtful landscaping and strategic design, gives you the feel of a private oasis. Inside, enjoy a serene ambience that defies expectations for in-town living.The house has a full unfinished basement for extra storage and possible expansion.

301 Liberty Ave, Winchester

Listing courtesy of Equity Realty. Contact:

Selling Office: Realty ONE Group Old Towne.

$635,500

This charming home, beautifully renovated in 2018, offers a perfect blend of classic elegance and modern comfort. With four spacious bedrooms and four well-appointed bathrooms, this residence features stunning hardwood flooring throughout. The gourmet kitchen, complete with stainless steel appliances and a generous island, is perfect for culinary enthusiasts. Enjoy cozy evenings by one of the four fireplaces, or bask in natural light from the bay window. Nestled in a welcoming community, this home is conveniently located near parks, schools, and the walking mall, making it an ideal spot for those seeking a vibrant neighborhood. The traditional floor plan includes built-ins and crown moldings, adding to the home's character. Experience the warmth and comfort of the backyard, with a cozy fireplace to keep you warm in the cooler months. This downtown home has it all! New roof 2024, new furnace 2023, new water heater 2024, new pressure pump 2023. Kitchen and bathroom updated in 2018.

4 Beds ⋅ 4 Baths

This charming home, beautifully renovated in 2018, offers a perfect blend of classic elegance and modern comfort. With four spacious bedrooms and four well-appointed bathrooms, this residence features stunning hardwood flooring throughout. The gourmet kitchen, complete with stainless steel appliances and a generous island, is perfect for culinary enthusiasts. Enjoy cozy evenings by one of the four fireplaces, or bask in natural light from the bay window. Nestled in a welcoming community, this home is conveniently located near parks, schools, and the walking mall, making it an ideal spot for those seeking a vibrant neighborhood. The traditional floor plan includes built-ins and crown moldings, adding to the home's character. Experience the warmth and comfort of the backyard, with a cozy fireplace to keep you warm in the cooler months. This downtown home has it all! New roof 2024, new furnace 2023, new water heater 2024, new pressure pump 2023. Kitchen and bathroom updated in 2018.

315 W Leicester St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Re/Max Roots.

$406,000

1815 Reese Court is an attractive new 3 level townhome with full brick front in Winchester, VA. Move-in Ready! Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful Quartz countertops, stone grey 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. Up to $6,500 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.*

4 Beds ⋅ 4 Baths

1815 Reese Court is an attractive new 3 level townhome with full brick front in Winchester, VA. Move-in Ready! Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful Quartz countertops, stone grey 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. Up to $6,500 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.*

1815 Reese Ct, Winchester

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

Spacious 4-bedroom, 2.5-bath home located in a desirable neighborhood just minutes from downtown. The main level features a family room, large eat-in kitchen with fireplace and bay window looking over the rear yard. The lower level features a game room with fireplace and opens onto the rear deck overlooking the pool. Upstairs offers four bedrooms, including a private owner’s suite. Outdoor amenities include a deck, in-ground swimming pool, and views of the Museum of the Shenandoah Valley.

$578,000

Spacious 4-bedroom, 2.5-bath home located in a desirable neighborhood just minutes from downtown. The main level features a family room, large eat-in kitchen with fireplace and bay window looking over the rear yard. The lower level features a game room with fireplace and opens onto the rear deck overlooking the pool. Upstairs offers four bedrooms, including a private owner’s suite. Outdoor amenities include a deck, in-ground swimming pool, and views of the Museum of the Shenandoah Valley.

107 Roszel Rd, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Realty ONE Group Old Towne.

$665,000

If you can find a better-maintained and updated home, buy it! Immaculate four-bedroom, four-bath home located on a quiet City cul-de-sac. Freshly painted, wainscoting has been recently added to the formal dining room. New roof and guttering, new tankless water heater. The primary bath has been remodeled, and an additional walk-in closet has been added, for a total of two walk-in closets in the master. All new, upgraded appliances include double ovens with an air fryer, new carpet runners on stairs, and fabulous replacement front doors. Outside features include a Trex deck, patio, pergola, upgraded landscaping, and irrigation. New garage doors. Finished basement with full bath. Charming study on the main floor with built-ins.Vaulted family room with floor-to-ceiling stone fireplace. No need to spend any money on this beautiful home after closing, it's all been done!

4 Beds ⋅ 5 Baths

If you can find a better-maintained and updated home, buy it! Immaculate four-bedroom, four-bath home located on a quiet City cul-de-sac. Freshly painted, wainscoting has been recently added to the formal dining room. New roof and guttering, new tankless water heater. The primary bath has been remodeled, and an additional walk-in closet has been added, for a total of two walk-in closets in the master. All new, upgraded appliances include double ovens with an air fryer, new carpet runners on stairs, and fabulous replacement front doors. Outside features include a Trex deck, patio, pergola, upgraded landscaping, and irrigation. New garage doors. Finished basement with full bath. Charming study on the main floor with built-ins.Vaulted family room with floor-to-ceiling stone fireplace. No need to spend any money on this beautiful home after closing, it's all been done!

922 Meadow Ct, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Pearson Smith Realty LLC.

$425,000

Location, Location. Brick Rancher offers Walkout Basement, 4 Bedrooms, Two Full Baths. Hardwood Floors throughout. Front Entry Ceramic Tiled. Kitchen Luxury Vinyl Floor, New Dishwasher,Disposal, Refrigerator with Ice-maker( Not Hooked Up) and Electric Range. Basement Partially Finished with Brick Fireplace with Timberline Wood Stove Insert, Fourth Bedroom, Laundry and Storage Area. Rear 15x12 Concrete Patio of Garage. Large Back Yard with Chain-link Fencing. Two Outbuildings for Storage. One Car Garage with Concrete Driveway.

Location, Location. Brick Rancher offers Walkout Basement, 4 Bedrooms, Two Full Baths. Hardwood Floors throughout. Front Entry Ceramic Tiled. Kitchen Luxury Vinyl Floor, New Dishwasher,Disposal, Refrigerator with Ice-maker( Not Hooked Up) and Electric Range. Basement Partially Finished with Brick Fireplace with Timberline Wood Stove Insert, Fourth Bedroom, Laundry and Storage Area. Rear 15x12 Concrete Patio of Garage. Large Back Yard with Chain-link Fencing. Two Outbuildings for Storage. One Car Garage with Concrete Driveway.

341 Wood Ave, Winchester

Listing courtesy of Jim Barb Realty Inc.. Contact:

Selling Office: MarketPlace REALTY.

$181,000

Great investor opportunity in the heart of Winchester! The LOWEST priced detached house within a 10-mile radius!! This 3-level home with a 2-car detached garage on a level treed lot is ideal for investors looking to fix and flip or fix and hold, with Shenandoah University only 3 miles away and Winchester Medical Center only 4 miles away. This detached 1933 front porch Cottage home on .20 acre lot sold strictly 'As-Is.' The house has one bedroom on the main level with a full bathroom, living room, and kitchen, plus a finished upper level with a 2nd large bedroom and an unfinished basement on public water and sewer with no HOA. Fabulous location just minutes to the historic city center and major commuting routes. Walking distance to historic Winchester shops, restaurants, and breweries. Close to Jim Barnett Park and the MSV hiking trails.

2 Beds ⋅ 1 Baths

Great investor opportunity in the heart of Winchester! The LOWEST priced detached house within a 10-mile radius!! This 3-level home with a 2-car detached garage on a level treed lot is ideal for investors looking to fix and flip or fix and hold, with Shenandoah University only 3 miles away and Winchester Medical Center only 4 miles away. This detached 1933 front porch Cottage home on .20 acre lot sold strictly 'As-Is.' The house has one bedroom on the main level with a full bathroom, living room, and kitchen, plus a finished upper level with a 2nd large bedroom and an unfinished basement on public water and sewer with no HOA. Fabulous location just minutes to the historic city center and major commuting routes. Walking distance to historic Winchester shops, restaurants, and breweries. Close to Jim Barnett Park and the MSV hiking trails.

27 Jackson Ave, Winchester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

$420,000

Unbeatable location on quiet street with oversized parcel in city limits within walking distance of Creekside Station and Kernstown Battlefield. This property does not have covenants or restrictions and the detached carport can handle a slew of large vehicles. Interior has the necessary accommodations with sunroom, office/den and family room. Partial basement adds some storage but also a rec room for visitors, gym, or hangout spot.

Unbeatable location on quiet street with oversized parcel in city limits within walking distance of Creekside Station and Kernstown Battlefield. This property does not have covenants or restrictions and the detached carport can handle a slew of large vehicles. Interior has the necessary accommodations with sunroom, office/den and family room. Partial basement adds some storage but also a rec room for visitors, gym, or hangout spot.

2808 Saratoga Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: RE/MAX Roots.

$370,000

Brand new end-unit townhouse in Laurelwood Commons Community, located just minutes from the heart of downtown. This stylish two-story townhouse features a welcoming foyer that leads into a bright, open-concept great room, perfect for relaxing or entertaining. The gourmet kitchen is equipped with stainless steel appliances, ample cabinetry, and a spacious island that flows seamlessly into the dining area. A convenient half bath completes the main level. Second floor has three generously sized bedrooms, including a serene primary suite with a private bath and walk-in closet. Two full bathroom and a second-floor laundry room add ease and efficiency. Enjoy the perfect blend of comfort, and convenience. Located within walking distance to charming shops and restaurants in Old Town, and just minutes from Jim Barnett Park, which features trails, playgrounds, a pool, and sports courts. With quick access to Route 7 and I-81. Don't miss this opportunity to own a beautifully designed, move-in ready townhouse in one of Winchester's most convenient location. Please use this GPS address: 532 N Pleasant Valley Rd, Winchester, VA 22601

Brand new end-unit townhouse in Laurelwood Commons Community, located just minutes from the heart of downtown. This stylish two-story townhouse features a welcoming foyer that leads into a bright, open-concept great room, perfect for relaxing or entertaining. The gourmet kitchen is equipped with stainless steel appliances, ample cabinetry, and a spacious island that flows seamlessly into the dining area. A convenient half bath completes the main level. Second floor has three generously sized bedrooms, including a serene primary suite with a private bath and walk-in closet. Two full bathroom and a second-floor laundry room add ease and efficiency. Enjoy the perfect blend of comfort, and convenience. Located within walking distance to charming shops and restaurants in Old Town, and just minutes from Jim Barnett Park, which features trails, playgrounds, a pool, and sports courts. With quick access to Route 7 and I-81. Don't miss this opportunity to own a beautifully designed, move-in ready townhouse in one of Winchester's most convenient location. Please use this GPS address: 532 N Pleasant Valley Rd, Winchester, VA 22601

613 Laurelwood Cir, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: RE Smart, LLC.

$525,000

Premier Single-Level Living on a Private Cul-de-Sac! Nestled at the end of a quiet, prestigious cul-de-sac, this exquisite one-level ranch home presents a rare opportunity to acquire a property where meticulous maintenance meets masterful design. Shielded from through-traffic and enveloped by landscaped gardens. The home offers an immediate sense of arrival and tranquil privacy. A Grand and Gracious Main Level. Step through the entryway into a Spacious great room, with a soaring cathedral ceiling. This architectural design floods the space with natural light, creating an atmosphere of grandeur and openness that forms the heart of the home. The flow is both intuitive and impressive, guiding you from the expansive living area directly into the well-appointed kitchen, a chef’s delight featuring modern appliances, ample cabinetry, and generous counter space. Adjacent to the kitchen, a sun-drenched dining area offers a perfect formal space for entertaining, with serene views of the lush outdoors. This entire main level is designed for seamless living and sophisticated gatherings. Retire to the private wing of the home where three spacious bedrooms provide a restful escape. The primary suite is a true sanctuary, featuring a well-proportioned layout and a luxurious en-suite bathroom designed for relaxation. Two additional bedrooms, each with generous closet space, share a beautifully appointed main hall bathroom, ensuring comfort and convenience for family and guests alike. A Fully Equipped Sanctuary located on the lower level. The home’s exceptional versatility is fully realized in the impeccably finished lower level. This space is a complete, self-contained in-law suite or guest retreat, offering total privacy. It features a large recreation room with endless possibilities. A kitchenette allows for independent living, while a spacious den/bedroom and a pristine full bathroom ensure comfort and convenience. This suite is perfect for multi-generational families or guests. Step outside to discover your own personal resort. The backyard is a masterpiece of low-maintenance landscaping, designed for ultimate enjoyment and backing directly to green space, guaranteeing both breathtaking views and complete privacy. Overlooking this serene setting, a sophisticated electric retractable awning extends your living space outdoors. With the simple push of a button, create a shaded haven for al fresco dining, morning coffee, or evening entertaining. A Location Beyond Compare This home isn’t just a residence; it’s a gateway to a lifestyle of unparalleled convenience. It is perfectly positioned minutes from every essential amenity. Everyday Convenience: Close to shopping, grocery stores, and major commuter routes. Impeccably maintained and move-in ready, this property is a blend of function, and location. This is more than a house—it is the key to a life of ease and elegance. Your exclusive viewing awaits. Call today to tour this amazing property before it’s gone!

Premier Single-Level Living on a Private Cul-de-Sac! Nestled at the end of a quiet, prestigious cul-de-sac, this exquisite one-level ranch home presents a rare opportunity to acquire a property where meticulous maintenance meets masterful design. Shielded from through-traffic and enveloped by landscaped gardens. The home offers an immediate sense of arrival and tranquil privacy. A Grand and Gracious Main Level. Step through the entryway into a Spacious great room, with a soaring cathedral ceiling. This architectural design floods the space with natural light, creating an atmosphere of grandeur and openness that forms the heart of the home. The flow is both intuitive and impressive, guiding you from the expansive living area directly into the well-appointed kitchen, a chef’s delight featuring modern appliances, ample cabinetry, and generous counter space. Adjacent to the kitchen, a sun-drenched dining area offers a perfect formal space for entertaining, with serene views of the lush outdoors. This entire main level is designed for seamless living and sophisticated gatherings. Retire to the private wing of the home where three spacious bedrooms provide a restful escape. The primary suite is a true sanctuary, featuring a well-proportioned layout and a luxurious en-suite bathroom designed for relaxation. Two additional bedrooms, each with generous closet space, share a beautifully appointed main hall bathroom, ensuring comfort and convenience for family and guests alike. A Fully Equipped Sanctuary located on the lower level. The home’s exceptional versatility is fully realized in the impeccably finished lower level. This space is a complete, self-contained in-law suite or guest retreat, offering total privacy. It features a large recreation room with endless possibilities. A kitchenette allows for independent living, while a spacious den/bedroom and a pristine full bathroom ensure comfort and convenience. This suite is perfect for multi-generational families or guests. Step outside to discover your own personal resort. The backyard is a masterpiece of low-maintenance landscaping, designed for ultimate enjoyment and backing directly to green space, guaranteeing both breathtaking views and complete privacy. Overlooking this serene setting, a sophisticated electric retractable awning extends your living space outdoors. With the simple push of a button, create a shaded haven for al fresco dining, morning coffee, or evening entertaining. A Location Beyond Compare This home isn’t just a residence; it’s a gateway to a lifestyle of unparalleled convenience. It is perfectly positioned minutes from every essential amenity. Everyday Convenience: Close to shopping, grocery stores, and major commuter routes. Impeccably maintained and move-in ready, this property is a blend of function, and location. This is more than a house—it is the key to a life of ease and elegance. Your exclusive viewing awaits. Call today to tour this amazing property before it’s gone!

2723 Windwood Dr, Winchester

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

END-UNIT ALL-BRICK TOWNHOUSE WITH NO HOA! This meticulously maintained, move-in ready home offers a blend of classic charm and high-end modern upgrades in a prime, convenient location. Sophisticated Interiors & High-End Upgrades: The main level showcases beautiful Maple Hardwood flooring flowing throughout the open living spaces. The heart of the home, the kitchen, features stunning Del-Wood Maple cabinetry in bright white, extending all the way to the ceiling, complemented by elegant Granite countertops (2019). The appliances were also updated in 2019. A custom-designed Butler’s Pantry and Laundry area is a functional showpiece, featuring matching cabinets and counters and providing a clever, hidden space for the washer and dryer—a perfect solution for seamless living. Relax by the wood-burning fireplace, beautifully accented by custom built-in shelving (2023) on each side, creating an inviting and organized focal point. New & Comfortable Upper Level: Stairs and all second-floor bedrooms boast brand-new, high-quality carpeting with upgraded, plush padding, ensuring a quiet, comfortable retreat. Both bathrooms have been elegantly updated: the full bath features cultured granite walls and sink counter (2019), and the half bath has been professionally updated to match the home's aesthetic. The entire home was just freshly painted in a desirable, neutral palette. Low-Maintenance Exterior & Prime Location: The heavy lifting is done! Major exterior updates completed in 2019 include the roof, gutters, front door, hot water heater, rear sliding door, and rear siding. The private backyard oasis is fully enclosed by a privacy fence, creating a perfect space for quiet nights on the back patio or entertaining friends. The professionally winterized grounds and freshly pruned perennial beds ensure a beautiful, low-maintenance transition for the new owner, with stunning blooms to look forward to next spring. An adorable outdoor building provides ideal storage or could be converted into a cozy hobby/work area. Commuter & Lifestyle Friendly: Enjoy a truly convenient location with easy access to Route 37, 50, 522, I-81, and Route 7. You are minutes from Valley Health/Winchester Medical Center, Shenandoah University, and a wide array of shopping and dining. Downtown Winchester offers vibrant shopping, dining, entertainment, and year-round festivals. Wineries, breweries, cideries, outdoor recreation, and history are all just a short drive away. This is a maintained home with an easy flow—ready for you to move in and enjoy!

$320,000

END-UNIT ALL-BRICK TOWNHOUSE WITH NO HOA! This meticulously maintained, move-in ready home offers a blend of classic charm and high-end modern upgrades in a prime, convenient location. Sophisticated Interiors & High-End Upgrades: The main level showcases beautiful Maple Hardwood flooring flowing throughout the open living spaces. The heart of the home, the kitchen, features stunning Del-Wood Maple cabinetry in bright white, extending all the way to the ceiling, complemented by elegant Granite countertops (2019). The appliances were also updated in 2019. A custom-designed Butler’s Pantry and Laundry area is a functional showpiece, featuring matching cabinets and counters and providing a clever, hidden space for the washer and dryer—a perfect solution for seamless living. Relax by the wood-burning fireplace, beautifully accented by custom built-in shelving (2023) on each side, creating an inviting and organized focal point. New & Comfortable Upper Level: Stairs and all second-floor bedrooms boast brand-new, high-quality carpeting with upgraded, plush padding, ensuring a quiet, comfortable retreat. Both bathrooms have been elegantly updated: the full bath features cultured granite walls and sink counter (2019), and the half bath has been professionally updated to match the home's aesthetic. The entire home was just freshly painted in a desirable, neutral palette. Low-Maintenance Exterior & Prime Location: The heavy lifting is done! Major exterior updates completed in 2019 include the roof, gutters, front door, hot water heater, rear sliding door, and rear siding. The private backyard oasis is fully enclosed by a privacy fence, creating a perfect space for quiet nights on the back patio or entertaining friends. The professionally winterized grounds and freshly pruned perennial beds ensure a beautiful, low-maintenance transition for the new owner, with stunning blooms to look forward to next spring. An adorable outdoor building provides ideal storage or could be converted into a cozy hobby/work area. Commuter & Lifestyle Friendly: Enjoy a truly convenient location with easy access to Route 37, 50, 522, I-81, and Route 7. You are minutes from Valley Health/Winchester Medical Center, Shenandoah University, and a wide array of shopping and dining. Downtown Winchester offers vibrant shopping, dining, entertainment, and year-round festivals. Wineries, breweries, cideries, outdoor recreation, and history are all just a short drive away. This is a maintained home with an easy flow—ready for you to move in and enjoy!

2150 Harvest Dr, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Buyer Financing Has Fallen Through – Seller is Highly Motivated!!!!. A classic brick ranch in Winchester, VA, has three bedrooms and two full bathrooms. The basement includes a separate entrance, a laundry area, a full bathroom, and an additional bonus room. Recent updates include: finished basement, new HVAC system, complete renovations of both bathrooms, new hardwood flooring, and an updated kitchen with new cabinets and countertops. No HOA restrictions. Don't miss your chance to see this inviting home—schedule a visit!

$340,000

Buyer Financing Has Fallen Through – Seller is Highly Motivated!!!!. A classic brick ranch in Winchester, VA, has three bedrooms and two full bathrooms. The basement includes a separate entrance, a laundry area, a full bathroom, and an additional bonus room. Recent updates include: finished basement, new HVAC system, complete renovations of both bathrooms, new hardwood flooring, and an updated kitchen with new cabinets and countertops. No HOA restrictions. Don't miss your chance to see this inviting home—schedule a visit!

1005 Pennsylvania Ave, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact:

Selling Office: MarketPlace REALTY.

$625,900

Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The open foyer invites you into this spacious home boasting over 3500 sq.ft. plus a full walk-out basement, ready to finish for additional square footage. Large living and dining rooms with hardwood, den or office. Large kitchen features granite counters, stainless steel appliances, and a breakfast area that opens to the family room with a fireplace. Two staircases to the second level that has four bedrooms plus a large playroom, library, or music room. Large patio to enjoy the level yard and play area. New gas furnace-2024, upstairs HAVC replaced in 2023. Cedar raised garden beds, EV car charger electrical setup in garage.

Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The open foyer invites you into this spacious home boasting over 3500 sq.ft. plus a full walk-out basement, ready to finish for additional square footage. Large living and dining rooms with hardwood, den or office. Large kitchen features granite counters, stainless steel appliances, and a breakfast area that opens to the family room with a fireplace. Two staircases to the second level that has four bedrooms plus a large playroom, library, or music room. Large patio to enjoy the level yard and play area. New gas furnace-2024, upstairs HAVC replaced in 2023. Cedar raised garden beds, EV car charger electrical setup in garage.

2321 Stoneridge Rd, Winchester

Listing courtesy of Colony Realty. Contact: