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Charming, meticulously maintained brick rancher in the heart of Winchester City! This move-in-ready home features 3 spacious bedrooms, 1 full bath, and a convenient half bath. Step inside to find gorgeous hard wood floors and several rooms boasting fresh, modern paint. The fully finished basement ( with radon system installed) offers incredible bonus square footage, perfect for a family room, home office, or recreation space. Outdoor living is a breeze on the private backyard brick patio, situated on a peaceful, quiet street. Driveway provides convenient off-street parking. New Refrigerator, washer and dryer convey. Location is everything! Enjoy the convenience of in-town living while staying just minutes away from major commuting routes, shopping, and dining. Don't miss this Winchester gem—schedule your tour today!

3 Beds ⋅ 2 Baths

Charming, meticulously maintained brick rancher in the heart of Winchester City! This move-in-ready home features 3 spacious bedrooms, 1 full bath, and a convenient half bath. Step inside to find gorgeous hard wood floors and several rooms boasting fresh, modern paint. The fully finished basement ( with radon system installed) offers incredible bonus square footage, perfect for a family room, home office, or recreation space. Outdoor living is a breeze on the private backyard brick patio, situated on a peaceful, quiet street. Driveway provides convenient off-street parking. New Refrigerator, washer and dryer convey. Location is everything! Enjoy the convenience of in-town living while staying just minutes away from major commuting routes, shopping, and dining. Don't miss this Winchester gem—schedule your tour today!

912 Allen Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Non Subscribing Office.

$435,000

Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly to sell by motivated seller. Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready for you to call home. Main Level Elegance & Modern Upgrades From the moment you step onto the extended front porch and through the foyer, you are greeted by freshly refinished hardwood floors and an abundance of natural light. The main level has been extensively refreshed with: Gourmet Kitchen Updates: BRAND New Granite countertops, deep-basin sink, modern faucets, and brand-new stainless microwave and dishwasher. Designer Lighting: Updated recessed lighting, new ceiling fans, and contemporary fixtures throughout. Cozy Living Spaces: Choose between the sophisticated study with a gas fireplace or the expansive family room featuring new premium carpet and padding. Unrivaled Garage & Bonus Potential The oversized two-car garage is a standout feature, boasting freshly painted floors and ample room for tools, bikes, and outdoor gear. Unique to this property is the massive vertical clearance above the garage doors—an ideal footprint for a future yoga studio, private home office, or secondary loft space. Upper-Level Retreat The second floor features brand-new, plush carpeting and upgraded hardware on every door. Primary Suite: A true sanctuary featuring a large en-suite bathroom, walk-in closets, and a jetted soaking tub for ultimate relaxation. Modern Bathrooms: Completely updated with new flooring and "new-age" LED-lit faucets that add a touch of modern luxury. Ultimate Convenience: Enjoy the dedicated second-story laundry room, eliminating the need to haul hampers up and down the stairs. Quality & Value This home isn’t just beautiful; it’s built for peace of mind: Newer Roof: Recently replaced and built to last. High-Efficiency HVAC: Less than 5 years old, ensuring low utility costs and year-round comfort. Instant Equity: Offered below a recent professional appraisal (see attached report). Expansion Ready: The vast, unfinished basement is a blank canvas for a home gym, theater, guest suite, or basically what you can imagine. Step outside to your private rear yard—perfect for summer BBQs and quiet evenings. This rare find combines a premier location with turn-key updates. Schedule your tour today before it's gone!

4 Beds ⋅ 3 Baths

Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly to sell by motivated seller. Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready for you to call home. Main Level Elegance & Modern Upgrades From the moment you step onto the extended front porch and through the foyer, you are greeted by freshly refinished hardwood floors and an abundance of natural light. The main level has been extensively refreshed with: Gourmet Kitchen Updates: BRAND New Granite countertops, deep-basin sink, modern faucets, and brand-new stainless microwave and dishwasher. Designer Lighting: Updated recessed lighting, new ceiling fans, and contemporary fixtures throughout. Cozy Living Spaces: Choose between the sophisticated study with a gas fireplace or the expansive family room featuring new premium carpet and padding. Unrivaled Garage & Bonus Potential The oversized two-car garage is a standout feature, boasting freshly painted floors and ample room for tools, bikes, and outdoor gear. Unique to this property is the massive vertical clearance above the garage doors—an ideal footprint for a future yoga studio, private home office, or secondary loft space. Upper-Level Retreat The second floor features brand-new, plush carpeting and upgraded hardware on every door. Primary Suite: A true sanctuary featuring a large en-suite bathroom, walk-in closets, and a jetted soaking tub for ultimate relaxation. Modern Bathrooms: Completely updated with new flooring and "new-age" LED-lit faucets that add a touch of modern luxury. Ultimate Convenience: Enjoy the dedicated second-story laundry room, eliminating the need to haul hampers up and down the stairs. Quality & Value This home isn’t just beautiful; it’s built for peace of mind: Newer Roof: Recently replaced and built to last. High-Efficiency HVAC: Less than 5 years old, ensuring low utility costs and year-round comfort. Instant Equity: Offered below a recent professional appraisal (see attached report). Expansion Ready: The vast, unfinished basement is a blank canvas for a home gym, theater, guest suite, or basically what you can imagine. Step outside to your private rear yard—perfect for summer BBQs and quiet evenings. This rare find combines a premier location with turn-key updates. Schedule your tour today before it's gone!

620 Crystal Ct, Winchester

Listing courtesy of Realty FC. Contact:

Selling Office: Impact Real Estate, LLC.

$305,000

HERE IS YOUR CHANCE! BACK ON THE MARKET DUE TO NO FAULT OF THE SELLERS!! DIRECTIONS FOR PARKING; FROM NAT AVE TAKE RIGHT ON ATHEY ALLY TO 4 CAR PARKING AREA ON LEFT - LOOK FOR 406 MARKER. Located in The Historic Old Town Winchester area with private parking right off of Athey Alley, we are happy to list this nicely remodeled 2 story circa 1930s, center hall home.. Since the purchase of this home, the owners have totally resurfaced and painted the metal roof, installed windows,installed all new plumbing and electrical services, a dual zoned HVAC system in 2024, sanded the gleaming pine floors, installed new vanities,new stainless appliances, installed a vinyl picket fence out front, new exterior doors and a privacy fence in the back. The only things left are cosmetic. This home still has the features we look for in an older home. There is a turned staircase, 6" base molding, original doors and doorknobs. an upstairs enclosed sleeping porch and more. An added bonus is a 4 car off street parking area that is a part of this property. There is very little left to do here, So, move in and enjoy it.

3 Beds ⋅ 2 Baths

HERE IS YOUR CHANCE! BACK ON THE MARKET DUE TO NO FAULT OF THE SELLERS!! DIRECTIONS FOR PARKING; FROM NAT AVE TAKE RIGHT ON ATHEY ALLY TO 4 CAR PARKING AREA ON LEFT - LOOK FOR 406 MARKER. Located in The Historic Old Town Winchester area with private parking right off of Athey Alley, we are happy to list this nicely remodeled 2 story circa 1930s, center hall home.. Since the purchase of this home, the owners have totally resurfaced and painted the metal roof, installed windows,installed all new plumbing and electrical services, a dual zoned HVAC system in 2024, sanded the gleaming pine floors, installed new vanities,new stainless appliances, installed a vinyl picket fence out front, new exterior doors and a privacy fence in the back. The only things left are cosmetic. This home still has the features we look for in an older home. There is a turned staircase, 6" base molding, original doors and doorknobs. an upstairs enclosed sleeping porch and more. An added bonus is a 4 car off street parking area that is a part of this property. There is very little left to do here, So, move in and enjoy it.

406 Highland Ave, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: Samson Properties.

$360,000

Welcome to this beautifully updated brick home offering the perfect blend of charm and modern updates. Major improvements completed in 2021 include a new roof, windows, HVAC system, kitchen cabinets with granite countertops, and a renovated main-level bathroom. A new water heater was installed in 2024. In 2026, a city-permitted addition created a spacious new primary bedroom and bathroom, along with new roof framing, siding, and plumbing. Conveniently located close to shopping, dining, and commuter routes, this move-in-ready home is ready for its next owner. The chimney in basement the only chimney is sealed off and can’t be used *Agent is related to landlord* 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.

4 Beds ⋅ 2 Baths

Welcome to this beautifully updated brick home offering the perfect blend of charm and modern updates. Major improvements completed in 2021 include a new roof, windows, HVAC system, kitchen cabinets with granite countertops, and a renovated main-level bathroom. A new water heater was installed in 2024. In 2026, a city-permitted addition created a spacious new primary bedroom and bathroom, along with new roof framing, siding, and plumbing. Conveniently located close to shopping, dining, and commuter routes, this move-in-ready home is ready for its next owner. The chimney in basement the only chimney is sealed off and can’t be used *Agent is related to landlord* 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.

236 Shawnee Ave, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Dream Real Estate.

$274,999

Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and low-maintenance townhouse living make this property an excellent choice for first-time buyers, downsizers, or anyone looking for a move-in-ready home. Conveniently located near Old Town Winchester's shopping, dining, and commuter routes. Don't miss your opportunity to make this beautiful home yours! 🏡✨

2 Beds ⋅ 3 Baths

Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and low-maintenance townhouse living make this property an excellent choice for first-time buyers, downsizers, or anyone looking for a move-in-ready home. Conveniently located near Old Town Winchester's shopping, dining, and commuter routes. Don't miss your opportunity to make this beautiful home yours! 🏡✨

206 Kimberly Way, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: M.O. Wilson Properties.

$1,000,000

Landmark, historic building for sale, Downtown Winchester, Virginia. Outstanding tenant history. Sold with 1st and 3rd floors leased, 2nd floor available for lease or end-user occupancy! A total of 7500 SF on three floors, located immediately adjacent to City Hall, across the street from public parking garage, and one block from Old Town Walking Mall and County municipal buildings. LOCATION LOCATION LOCATION. Iconically known as the Odd Fellows Building, built in 1930 and meticulously and historically restored for Class A office space with all modern amenities. Proforma GOI $100K+/annual. OPEX averages $20K/year (majority passed through to tenants via NNN fees). Ideal for owner-occupant wanting residual income, opportunity for growth, and a legacy investment. Two retail/office spaces on 1st floor, elevator to 2nd and 3rd floor office suites. Vaulted ceilings, massive, oversized windows, classic hardwood finishes, a true First Class building in meticulously cared-for condition. 2nd & 3rd floor residential conversion permitted under current zoning. See Agent Remarks for all recent upgrades, including NEW ROOF in 2023. Asking $1,299,000.

45 Boscawen St E, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Coldwell Banker Premier.

$580,000

Open House Sunday, July 19th from 12pm - 2pm! Welcome home to this spacious single-family home in the sought-after Williamsburg Heights community! This great home, located in the Winchester City limits, features 4 bedrooms, 2.5 bathrooms, 1 car detached garage, 3200 finished square feet on 2 levels, a huge deck, brick patio and vinyl fenced backyard. Recent updates include the kitchen with new white cabinetry, countertops, lighting and flooring (2019). Roof and HVAC (2019), composite deck (2026), vinyl fence (2025), water heater (2024), insulation and ductwork in the crawl space (2024), laundry room flooring (2024), seamless gutters (2023), wood burning stove (2025), and updated bathrooms (2020). The main level features an open kitchen with stainless steel appliances and a breakfast area. Great living room with hardwood floors, crown and chair moldings and a gas fireplace. Spacious family room with hardwood floors and a wood burning stove. Situated off the family room is the dining room and a huge open & bright sunroom with a bonus room. Completing the main level is the laundry room and half bathroom. Head upstairs to your large primary bedroom, which features an inviting sitting room with hardwood floors and built-in shelving and an updated bathroom. The bedroom level also includes 3 large bedrooms and a full bathroom. Looking to entertain, head outside to your fully fenced backyard featuring an oversized composite deck, brick patio, vinyl fence and tons of great landscaping. You are just minutes from Winchester Medical, schools, shopping, parks and restaurants! Don't miss the opportunity to make this amazing property your next home. Schedule a showing today!

4 Beds ⋅ 3 Baths

Open House Sunday, July 19th from 12pm - 2pm! Welcome home to this spacious single-family home in the sought-after Williamsburg Heights community! This great home, located in the Winchester City limits, features 4 bedrooms, 2.5 bathrooms, 1 car detached garage, 3200 finished square feet on 2 levels, a huge deck, brick patio and vinyl fenced backyard. Recent updates include the kitchen with new white cabinetry, countertops, lighting and flooring (2019). Roof and HVAC (2019), composite deck (2026), vinyl fence (2025), water heater (2024), insulation and ductwork in the crawl space (2024), laundry room flooring (2024), seamless gutters (2023), wood burning stove (2025), and updated bathrooms (2020). The main level features an open kitchen with stainless steel appliances and a breakfast area. Great living room with hardwood floors, crown and chair moldings and a gas fireplace. Spacious family room with hardwood floors and a wood burning stove. Situated off the family room is the dining room and a huge open & bright sunroom with a bonus room. Completing the main level is the laundry room and half bathroom. Head upstairs to your large primary bedroom, which features an inviting sitting room with hardwood floors and built-in shelving and an updated bathroom. The bedroom level also includes 3 large bedrooms and a full bathroom. Looking to entertain, head outside to your fully fenced backyard featuring an oversized composite deck, brick patio, vinyl fence and tons of great landscaping. You are just minutes from Winchester Medical, schools, shopping, parks and restaurants! Don't miss the opportunity to make this amazing property your next home. Schedule a showing today!

608 Bellview Ave, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$385,000

. Vintage 1950's Build, In The City of Winchester. Perfect City living, across from Virginia Avenue Elementary and Post Office! Walking Distance from Old Town Winchester VA!. Blocks from grocery stores, gas stations, bus stops, shopping, City transit and just of I 81 and Rt 7 for easy commuting ! This 4 Bedroom, 1 and half bath Cape Cod is spacious and ready for the new owner! The curb appeal is inviting. The home is well kept and has some updates. Inside the home, you will find a spacious living room with fireplace, and all hardwood floors on the main level. The kitchen is a large space with the total vintage look and feel, from cabinetry, countertops and the original flowered vinyl flooring. There are 2 bedrooms on the main level, kitchen, large living room and seperate dining room. The upper level has the full bathroom, still in its original vintage style with original tile flooring. The upper level also boasts 2 large bedrooms with window seats and lots of light! The basement is an unfinished space with a walk up stairway to the back yard. The Furnace is newer, roof is newer, basement walls have been sealed(will upload receipts into bright by 7/3 Home is sold as is. Inspections for information purposes only. Clarification the oil tanks in basement are from previous oil furnace. The heat is natural gas and the airnin centr

4 Beds ⋅ 2 Baths

. Vintage 1950's Build, In The City of Winchester. Perfect City living, across from Virginia Avenue Elementary and Post Office! Walking Distance from Old Town Winchester VA!. Blocks from grocery stores, gas stations, bus stops, shopping, City transit and just of I 81 and Rt 7 for easy commuting ! This 4 Bedroom, 1 and half bath Cape Cod is spacious and ready for the new owner! The curb appeal is inviting. The home is well kept and has some updates. Inside the home, you will find a spacious living room with fireplace, and all hardwood floors on the main level. The kitchen is a large space with the total vintage look and feel, from cabinetry, countertops and the original flowered vinyl flooring. There are 2 bedrooms on the main level, kitchen, large living room and seperate dining room. The upper level has the full bathroom, still in its original vintage style with original tile flooring. The upper level also boasts 2 large bedrooms with window seats and lots of light! The basement is an unfinished space with a walk up stairway to the back yard. The Furnace is newer, roof is newer, basement walls have been sealed(will upload receipts into bright by 7/3 Home is sold as is. Inspections for information purposes only. Clarification the oil tanks in basement are from previous oil furnace. The heat is natural gas and the airnin centr

419 Van Fossen St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Burch Real Estate Group, LLC.

$360,000

Welcome home to this charming 3-bedroom duplex nestled in the highly desirable Orchard Hill neighborhood of Winchester City. Enjoy the convenience of tree-lined sidewalks, street lights, and an easy walk to Park Place Park, making this location perfect for outdoor recreation and neighborhood strolls. Inside, you'll find three finished levels designed for comfortable living. The inviting living room features a cozy wood-burning fireplace, while the separate formal dining room provides the perfect space for entertaining family and friends. The kitchen is equipped with stainless steel appliances and offers plenty of functionality for everyday living. Upstairs, you'll find three spacious bedrooms, along with one full bath and two convenient half baths throughout the home. The finished walkout lower level expands your living space with a welcoming recreation room complete with a wet bar—ideal for game nights, movie marathons, or hosting guests. A dedicated laundry room includes the washer and dryer for added convenience. Step outside to enjoy a peaceful backyard with patio that backs to mature trees, providing privacy and a relaxing natural setting. Combining comfort, character, and an unbeatable location close to parks, shopping, dining, and commuter routes, this delightful Orchard Hill duplex is ready to welcome you home!

3 Beds ⋅ 3 Baths

Welcome home to this charming 3-bedroom duplex nestled in the highly desirable Orchard Hill neighborhood of Winchester City. Enjoy the convenience of tree-lined sidewalks, street lights, and an easy walk to Park Place Park, making this location perfect for outdoor recreation and neighborhood strolls. Inside, you'll find three finished levels designed for comfortable living. The inviting living room features a cozy wood-burning fireplace, while the separate formal dining room provides the perfect space for entertaining family and friends. The kitchen is equipped with stainless steel appliances and offers plenty of functionality for everyday living. Upstairs, you'll find three spacious bedrooms, along with one full bath and two convenient half baths throughout the home. The finished walkout lower level expands your living space with a welcoming recreation room complete with a wet bar—ideal for game nights, movie marathons, or hosting guests. A dedicated laundry room includes the washer and dryer for added convenience. Step outside to enjoy a peaceful backyard with patio that backs to mature trees, providing privacy and a relaxing natural setting. Combining comfort, character, and an unbeatable location close to parks, shopping, dining, and commuter routes, this delightful Orchard Hill duplex is ready to welcome you home!

824 Appleseed Ct, Winchester

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

Selling Office: Real Broker, LLC.

$349,990

Expect a long love affair with this home. Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a front-row seat to one of Winchester’s most exciting visions for tomorrow. Inside, tall ceilings give the rooms an airy, gracious presence, while the preserved woodwork around the door frames and staircases brings in the kind of craftsmanship that is nearly impossible to recreate. Every doorway feels intentional. Every turn of the staircase reminds you this home has a story. Even better, the home features two staircases, plus an additional staircase leading to the attic—an uncommon old-house detail that adds character, convenience, and intriguing future flexibility. The attic offers potential for a finished loft or creative bonus space later, subject to buyer due diligence, permits, and approvals. With 3 bedrooms and 1 full bath, the home feels warm, grounded, and refreshingly authentic—never cookie-cutter, never stripped of its soul. The kitchen has been refreshed with new drywall and pendant lighting in 2026, adding a clean, current touch while still letting the home’s original personality shine. The bathroom was recently remodeled in 2026, electrical has been updated, new plumbing pipes were run in 2024, and the windows have been replaced within the last three years. The roof was replaced in 2021, the upstairs HVAC was replaced in 2019, and a new hot water heater was installed in 2026. These are the improvements that matter: the ones that help you enjoy the tall ceilings, old-house texture, and beautiful woodwork with added confidence. The back of the home is just as inviting. Dual rear porches create two easy places to start the morning, wind down in the evening, or enjoy the backyard from a shaded perch. Beyond them, a generous 20 by 20 patio gives you room for outdoor dining, container gardens, a firepit setup, or a relaxed weekend gathering space. The flat lot keeps the yard practical and flexible, with open space that feels simple to use and easy to enjoy. The location is where this home becomes especially compelling. Old Town Winchester is known for its local dining, shopping, events, museums, and attractions, giving the surrounding area a lively historic-downtown feel. First Fridays bring local artists, live music, sip-and-stroll energy, and special events to the heart of Old Town. Jim Barnett Park adds more than 170 acres of green space and amenities, while the Museum of the Shenandoah Valley offers galleries, gardens, and daily trail access. Then add Cider Hill. The City of Winchester describes the Cider Hill Neighborhood Design District as an approved future vision focused on revitalizing a historically industrial area into a vibrant mixed-use community through adaptive reuse, enhanced connectivity, and a balance of residential, commercial, and public spaces. In plain language, that means this home is positioned beside an area planned to become more active, more connected, and more useful over time—placing it in the middle of several attractive Winchester destinations as the district evolves. That combination is hard to duplicate: historic architecture, meaningful updates, outdoor living, a flat backyard, proximity to Old Town, adjacency to a planned mixed-use district, two staircases, and attic access with future upside. This is not a house trying to look historic. It is the real thing, with height, texture, craftsmanship, porches, and practical improvements already in place. For anyone hoping to find a home with genuine old-house warmth near Winchester’s historic core—and near a city-backed district with a bold future vision—this one is easy to love and hard to forget. Owner is an inactive Virginia realtor.

3 Beds ⋅ 1 Baths

Expect a long love affair with this home. Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a front-row seat to one of Winchester’s most exciting visions for tomorrow. Inside, tall ceilings give the rooms an airy, gracious presence, while the preserved woodwork around the door frames and staircases brings in the kind of craftsmanship that is nearly impossible to recreate. Every doorway feels intentional. Every turn of the staircase reminds you this home has a story. Even better, the home features two staircases, plus an additional staircase leading to the attic—an uncommon old-house detail that adds character, convenience, and intriguing future flexibility. The attic offers potential for a finished loft or creative bonus space later, subject to buyer due diligence, permits, and approvals. With 3 bedrooms and 1 full bath, the home feels warm, grounded, and refreshingly authentic—never cookie-cutter, never stripped of its soul. The kitchen has been refreshed with new drywall and pendant lighting in 2026, adding a clean, current touch while still letting the home’s original personality shine. The bathroom was recently remodeled in 2026, electrical has been updated, new plumbing pipes were run in 2024, and the windows have been replaced within the last three years. The roof was replaced in 2021, the upstairs HVAC was replaced in 2019, and a new hot water heater was installed in 2026. These are the improvements that matter: the ones that help you enjoy the tall ceilings, old-house texture, and beautiful woodwork with added confidence. The back of the home is just as inviting. Dual rear porches create two easy places to start the morning, wind down in the evening, or enjoy the backyard from a shaded perch. Beyond them, a generous 20 by 20 patio gives you room for outdoor dining, container gardens, a firepit setup, or a relaxed weekend gathering space. The flat lot keeps the yard practical and flexible, with open space that feels simple to use and easy to enjoy. The location is where this home becomes especially compelling. Old Town Winchester is known for its local dining, shopping, events, museums, and attractions, giving the surrounding area a lively historic-downtown feel. First Fridays bring local artists, live music, sip-and-stroll energy, and special events to the heart of Old Town. Jim Barnett Park adds more than 170 acres of green space and amenities, while the Museum of the Shenandoah Valley offers galleries, gardens, and daily trail access. Then add Cider Hill. The City of Winchester describes the Cider Hill Neighborhood Design District as an approved future vision focused on revitalizing a historically industrial area into a vibrant mixed-use community through adaptive reuse, enhanced connectivity, and a balance of residential, commercial, and public spaces. In plain language, that means this home is positioned beside an area planned to become more active, more connected, and more useful over time—placing it in the middle of several attractive Winchester destinations as the district evolves. That combination is hard to duplicate: historic architecture, meaningful updates, outdoor living, a flat backyard, proximity to Old Town, adjacency to a planned mixed-use district, two staircases, and attic access with future upside. This is not a house trying to look historic. It is the real thing, with height, texture, craftsmanship, porches, and practical improvements already in place. For anyone hoping to find a home with genuine old-house warmth near Winchester’s historic core—and near a city-backed district with a bold future vision—this one is easy to love and hard to forget. Owner is an inactive Virginia realtor.

519 Fairmont Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$450,000

Ideal concept for one-level living with an open floor plan that still provides areas for private spaces. Lovely hardwood floors tie the plan together, from the cozy fireplace to warm winter evenings, to the shady screened porch to catch the Spring and Fall breezes. Well maintained neighborhood near services, shopping, schools and access to commuting thoroughfares. Newer roof, new rear fence, new HVAC and all new kitchen appliances!!! Samsung TV in family room conveys too..... Seller has added extra layers of insulation in the attic to augment the comfort level in both winter and summer and add life to the HVAC unit.

3 Beds ⋅ 3 Baths

Ideal concept for one-level living with an open floor plan that still provides areas for private spaces. Lovely hardwood floors tie the plan together, from the cozy fireplace to warm winter evenings, to the shady screened porch to catch the Spring and Fall breezes. Well maintained neighborhood near services, shopping, schools and access to commuting thoroughfares. Newer roof, new rear fence, new HVAC and all new kitchen appliances!!! Samsung TV in family room conveys too..... Seller has added extra layers of insulation in the attic to augment the comfort level in both winter and summer and add life to the HVAC unit.

209 W Cedarmeade, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: RE/MAX Roots.

$302,000

Step into a world of timeless elegance and modern luxury with this stunning Colonial residence, beautifully renovated in 2015 while preserving its historic charm. Nestled in a serene setting, this detached home offers a perfect blend of classic architecture and contemporary comforts, making it an ideal retreat for those seeking an exclusive lifestyle. As you enter, you are greeted by rich hardwood floors that flow seamlessly throughout the main living areas, accentuated by exquisite crown moldings that add a touch of sophistication. The traditional floor plan invites you to explore a spacious dining area, perfect for hosting intimate gatherings or festive celebrations. The heart of the home features a gourmet kitchen equipped with high-end appliances, including a built-in microwave, gas oven/range, and a sleek dishwasher, ensuring culinary adventures are a delight. The upgraded countertops provide ample space for meal prep, while the pantry offers convenient storage for all your essentials. This residence boasts four bedrooms, each designed with comfort in mind. The primary suite features a luxurious walk-in closet, providing an abundance of storage space, while the three full bathrooms are elegantly appointed with modern fixtures and finishes, ensuring a spa-like experience at home. The upper floor laundry adds a layer of convenience to your daily routine, making chores a breeze. Ceiling fans throughout the home enhance airflow and comfort, creating a welcoming atmosphere year-round. This outdoor space is perfect for morning coffee or evening gatherings under the stars, offering a seamless transition from indoor to outdoor living. With a lot size of 0.09 acres, this property is easy to maintain, allowing you to spend more time enjoying the finer things in life. On-street parking provides convenience for you and your guests. Located just under a mile from public transportation, this home offers easy access to the vibrant local community while maintaining a peaceful ambiance. Experience the perfect balance of historic charm and modern luxury in this exceptional property, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. Embrace a lifestyle of comfort and elegance in this remarkable home.

4 Beds ⋅ 3 Baths

Step into a world of timeless elegance and modern luxury with this stunning Colonial residence, beautifully renovated in 2015 while preserving its historic charm. Nestled in a serene setting, this detached home offers a perfect blend of classic architecture and contemporary comforts, making it an ideal retreat for those seeking an exclusive lifestyle. As you enter, you are greeted by rich hardwood floors that flow seamlessly throughout the main living areas, accentuated by exquisite crown moldings that add a touch of sophistication. The traditional floor plan invites you to explore a spacious dining area, perfect for hosting intimate gatherings or festive celebrations. The heart of the home features a gourmet kitchen equipped with high-end appliances, including a built-in microwave, gas oven/range, and a sleek dishwasher, ensuring culinary adventures are a delight. The upgraded countertops provide ample space for meal prep, while the pantry offers convenient storage for all your essentials. This residence boasts four bedrooms, each designed with comfort in mind. The primary suite features a luxurious walk-in closet, providing an abundance of storage space, while the three full bathrooms are elegantly appointed with modern fixtures and finishes, ensuring a spa-like experience at home. The upper floor laundry adds a layer of convenience to your daily routine, making chores a breeze. Ceiling fans throughout the home enhance airflow and comfort, creating a welcoming atmosphere year-round. This outdoor space is perfect for morning coffee or evening gatherings under the stars, offering a seamless transition from indoor to outdoor living. With a lot size of 0.09 acres, this property is easy to maintain, allowing you to spend more time enjoying the finer things in life. On-street parking provides convenience for you and your guests. Located just under a mile from public transportation, this home offers easy access to the vibrant local community while maintaining a peaceful ambiance. Experience the perfect balance of historic charm and modern luxury in this exceptional property, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. Embrace a lifestyle of comfort and elegance in this remarkable home.

317 N Kent St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$285,000

Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The property also features an amazing yard with plenty of space for gardening, entertaining, pets, or simply enjoying the outdoors. Inside, you'll find comfortable living spaces, 2 bedrooms, a partially finished basement, and a walk-up attic providing excellent storage and flexibility. Recent major improvements help make homeownership worry-free, including a new roof (2025), new AC condenser (2022), and new water heater (2021). Enjoy being close to Winchester's vibrant downtown pedestrian mall, local restaurants, coffee shops, parks, museums, and year-round community events that make the city such a desirable place to call home. Commuters will appreciate the easy access to Routes 50, 7, 522, and I-81, providing convenient travel throughout the Shenandoah Valley and beyond. A wonderful opportunity to own a well-maintained home with character, outdoor space, and an unbeatable location.

2 Beds ⋅ 1 Baths

Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The property also features an amazing yard with plenty of space for gardening, entertaining, pets, or simply enjoying the outdoors. Inside, you'll find comfortable living spaces, 2 bedrooms, a partially finished basement, and a walk-up attic providing excellent storage and flexibility. Recent major improvements help make homeownership worry-free, including a new roof (2025), new AC condenser (2022), and new water heater (2021). Enjoy being close to Winchester's vibrant downtown pedestrian mall, local restaurants, coffee shops, parks, museums, and year-round community events that make the city such a desirable place to call home. Commuters will appreciate the easy access to Routes 50, 7, 522, and I-81, providing convenient travel throughout the Shenandoah Valley and beyond. A wonderful opportunity to own a well-maintained home with character, outdoor space, and an unbeatable location.

102 N Purcell Ave, Winchester

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

Selling Office: Unrepresented.

$569,000

Welcome to this stunning, custom-built Craftsman-style home that perfectly balances contemporary elegance with everyday functionality. Located in a prime, highly convenient Winchester location, this property immediately captivates with its striking curb appeal, highlighted by a large covered front porch and a classic architectural silhouette. Step inside to discover an immaculate interior bathed in natural light, showcasing high-end finishes, a classic neutral color palette, and durable LVP flooring that flows seamlessly throughout. Expertly crafted with an emphasis on comfort and flow, the designer-inspired living room is anchored by a cozy electric fireplace that creates a warm, inviting atmosphere for family, friends, and guests. This level also features a convenient half bath, an oversized mudroom housing the laundry facilities, and a clever under-the-stairs nook complete with a built-in dog gate for your four-legged family members. Serving as the true heart of the home, the sleek, gourmet kitchen effortlessly unfolds from the living area in a brilliant open-concept design perfect for entertaining. It comes fully equipped with premium stainless steel appliances, bright white cabinetry, a walk-in pantry, a stylish backsplash, and a large center island accented by elegant pendant lighting and breakfast bar seating. Host unforgettable dinners in the gorgeous formal dining room, which offers an ideal backdrop for gatherings and seamless access to the outdoor living space. For ultimate convenience, the main-level primary bedroom serves as a private retreat, complete with a spa-like ensuite bathroom outfitted with double sinks and a massive walk-in glass shower. Upstairs, the home continues to impress with three additional generous bedrooms and a sizable full bathroom. The exterior amenities are just as impressive as the interior, featuring a 1-car attached garage and a fully fenced-in backyard with a spacious patio, manicured lawn, and beautiful mountain views. This pristine, turnkey property offers a rare combination of custom craftsmanship, high-end style, and an unbeatable location.

4 Beds ⋅ 3 Baths

Welcome to this stunning, custom-built Craftsman-style home that perfectly balances contemporary elegance with everyday functionality. Located in a prime, highly convenient Winchester location, this property immediately captivates with its striking curb appeal, highlighted by a large covered front porch and a classic architectural silhouette. Step inside to discover an immaculate interior bathed in natural light, showcasing high-end finishes, a classic neutral color palette, and durable LVP flooring that flows seamlessly throughout. Expertly crafted with an emphasis on comfort and flow, the designer-inspired living room is anchored by a cozy electric fireplace that creates a warm, inviting atmosphere for family, friends, and guests. This level also features a convenient half bath, an oversized mudroom housing the laundry facilities, and a clever under-the-stairs nook complete with a built-in dog gate for your four-legged family members. Serving as the true heart of the home, the sleek, gourmet kitchen effortlessly unfolds from the living area in a brilliant open-concept design perfect for entertaining. It comes fully equipped with premium stainless steel appliances, bright white cabinetry, a walk-in pantry, a stylish backsplash, and a large center island accented by elegant pendant lighting and breakfast bar seating. Host unforgettable dinners in the gorgeous formal dining room, which offers an ideal backdrop for gatherings and seamless access to the outdoor living space. For ultimate convenience, the main-level primary bedroom serves as a private retreat, complete with a spa-like ensuite bathroom outfitted with double sinks and a massive walk-in glass shower. Upstairs, the home continues to impress with three additional generous bedrooms and a sizable full bathroom. The exterior amenities are just as impressive as the interior, featuring a 1-car attached garage and a fully fenced-in backyard with a spacious patio, manicured lawn, and beautiful mountain views. This pristine, turnkey property offers a rare combination of custom craftsmanship, high-end style, and an unbeatable location.

2532 Middle Rd, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Pearson Smith Realty, LLC.

$424,000

Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main level includes a spacious primary suite with a walk-in closet and beautifully renovated bathroom showcasing a tiled shower with glass doors. An additional generously sized bedroom and full bath complete are also on the first floor. There is also a mud room/laundry area that has brand new flooring and leads out to the backyard. Upstairs you’ll find two more bedrooms plus access to a large attic , providing abundant storage space. The finished basement offers incredible flexibility — ideal for an in-law suite — complete with a full kitchen, spacious living area, two bedrooms, and a full bathroom. Outside, enjoy a long driveway with ample parking, two detached garages, and a sprawling flat yard designed for entertaining. The in-ground pool makes summer living even better!

6 Beds ⋅ 3 Baths

Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main level includes a spacious primary suite with a walk-in closet and beautifully renovated bathroom showcasing a tiled shower with glass doors. An additional generously sized bedroom and full bath complete are also on the first floor. There is also a mud room/laundry area that has brand new flooring and leads out to the backyard. Upstairs you’ll find two more bedrooms plus access to a large attic , providing abundant storage space. The finished basement offers incredible flexibility — ideal for an in-law suite — complete with a full kitchen, spacious living area, two bedrooms, and a full bathroom. Outside, enjoy a long driveway with ample parking, two detached garages, and a sprawling flat yard designed for entertaining. The in-ground pool makes summer living even better!

2250 Roosevelt Blvd, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$704,000

Available now in One of Winchester's Most Sought-After Locations. Opportunities like this don't come along often. Nestled on one of the most desirable streets in Winchester, just behind John Handley High School, this charming Cape Cod offers the perfect blend of character, comfort, and location. Lovingly maintained and full of curb appeal, this delightful four-bedroom, two-and-a-half-bath home welcomes you with timeless charm and thoughtful updates throughout. From the moment you arrive, you'll appreciate the warmth and care that has gone into preserving this special property. One of the home's most desirable features is the main-level primary bedroom, offering convenience and flexibility for a variety of lifestyles. Inside, you'll find inviting living spaces, an abundance of natural light, and the kind of character that's increasingly hard to find. A new roof installed in 2024 provides added peace of mind, while the home's thoughtful upkeep shines throughout. Whether you're drawn to the walkable neighborhood, the established setting, or the opportunity to own a home on one of Winchester's most treasured streets, this is a property you'll want to see as soon as it becomes available. Beautifully maintained. Perfectly positioned. Come see for yourself.

4 Beds ⋅ 3 Baths

Available now in One of Winchester's Most Sought-After Locations. Opportunities like this don't come along often. Nestled on one of the most desirable streets in Winchester, just behind John Handley High School, this charming Cape Cod offers the perfect blend of character, comfort, and location. Lovingly maintained and full of curb appeal, this delightful four-bedroom, two-and-a-half-bath home welcomes you with timeless charm and thoughtful updates throughout. From the moment you arrive, you'll appreciate the warmth and care that has gone into preserving this special property. One of the home's most desirable features is the main-level primary bedroom, offering convenience and flexibility for a variety of lifestyles. Inside, you'll find inviting living spaces, an abundance of natural light, and the kind of character that's increasingly hard to find. A new roof installed in 2024 provides added peace of mind, while the home's thoughtful upkeep shines throughout. Whether you're drawn to the walkable neighborhood, the established setting, or the opportunity to own a home on one of Winchester's most treasured streets, this is a property you'll want to see as soon as it becomes available. Beautifully maintained. Perfectly positioned. Come see for yourself.

622 Tennyson Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: RE/MAX Roots.

$1,688,000

Professional office building for sale in downtown Historic Winchester. Located at the Intersection of W. Piccadilly Street and N. Braddock Street. Located directly across the street from the Handley Public Library and Kimberly's Gifts & Boutique. Great downtown location with off-street parking. Interior features include beautiful hardwood floors, updated cherry molding and wainscotting. This historic building is 60% leased and known as the Old Post Office, which was built in 1910. This building has first and second floor area totaling 11,060 SF. The basement level is leased and finished and features total floor area of 3,333 SF. NOTE: There are two offices available. One has a floor area of 3,000 SF and the second has a floor area of 2,705 SF. $17,335.75/MO + $4.00 CAM

40 W Piccadilly St, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

Selling Office: Oakcrest Commercial Real Estate.

$440,000

Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for hosting unforgettable gatherings or enjoying quiet evenings under the stars. The main living level is a showstopper with a large quartz island, sleek stainless steel appliances, and luxury vinyl plank flooring that blends modern elegance with everyday comfort. Downstairs, the versatile lower-level family room and attached garage add both function and flexibility. Set in an amazing location and designed with a true Pinterest-worthy aesthetic, this home feels like a dream—and lives even better.

3 Beds ⋅ 3 Baths

Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for hosting unforgettable gatherings or enjoying quiet evenings under the stars. The main living level is a showstopper with a large quartz island, sleek stainless steel appliances, and luxury vinyl plank flooring that blends modern elegance with everyday comfort. Downstairs, the versatile lower-level family room and attached garage add both function and flexibility. Set in an amazing location and designed with a true Pinterest-worthy aesthetic, this home feels like a dream—and lives even better.

3137 Eton Pl, Winchester

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

Selling Office: EXP Realty, LLC.

$140,000

Tucked away on a quiet cul-de-sac, this 0.4174-acre lot offers a fantastic opportunity to build your dream home in a highly desirable Winchester location. Enjoy the convenience of being just minutes from Handley High School and the charm, dining, and shopping of downtown Winchester. The property features a 30' easement, allowing for access while still providing ample space for your vision. With its prime location and neighborhood setting, this lot is the perfect blend of privacy and accessibility.

1322 Vanceright Cir, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Colony Realty.

$600,000

Finally, a five-bedroom, 3.5 bath home in the city of Winchester with over 4200 sq ft of living space within minutes of Valley Health and shopping. Beautifully landscaped yard, including a vegetable garden, deck, and walkout basement. 2-zone heating and cooling, natural gas heat for the main floor and lower level, and a heat pump for the second floor.

5 Beds ⋅ 4 Baths

Finally, a five-bedroom, 3.5 bath home in the city of Winchester with over 4200 sq ft of living space within minutes of Valley Health and shopping. Beautifully landscaped yard, including a vegetable garden, deck, and walkout basement. 2-zone heating and cooling, natural gas heat for the main floor and lower level, and a heat pump for the second floor.

974 Wayne Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Realty ONE Group Old Towne.

$372,500

Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to an extended stone patio, plus enjoy the convenience of a 1-car garage for storage. Recent updates include a new HVAC (2024) and a new roof (2025). Low-maintenance living includes lawn care and snow removal, allowing more time to enjoy the community’s clubhouse, exercise room, game room, and scenic walking paths. Conveniently located near shopping, dining, and healthcare, Winchester Medical Center and close to local attractions, including performances at Shenandoah University Theatre, exhibits at the Shenandoah Valley Discovery Museum, and the galleries at the Museum of the Shenandoah Valley. A wonderful blend of comfort, convenience, and active 55+ community living in the heart of Winchester, Virginia. All sizes are approximate.

2 Beds ⋅ 2 Baths

Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to an extended stone patio, plus enjoy the convenience of a 1-car garage for storage. Recent updates include a new HVAC (2024) and a new roof (2025). Low-maintenance living includes lawn care and snow removal, allowing more time to enjoy the community’s clubhouse, exercise room, game room, and scenic walking paths. Conveniently located near shopping, dining, and healthcare, Winchester Medical Center and close to local attractions, including performances at Shenandoah University Theatre, exhibits at the Shenandoah Valley Discovery Museum, and the galleries at the Museum of the Shenandoah Valley. A wonderful blend of comfort, convenience, and active 55+ community living in the heart of Winchester, Virginia. All sizes are approximate.

1851 Melvor Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Realty ONE Group Old Towne.

$487,500

Conveniently located in the heart of Winchester, this spacious brick ranch offers the perfect combination of timeless character, thoughtful updates, and flexible living space. Situated on a nearly half-acre corner lot, the property provides room to spread out while remaining just minutes from Winchester Medical Center, shopping, dining, and major commuter routes. Inside, you'll find beautiful hardwood flooring throughout much of the main level and an abundance of natural light pouring through oversized windows. The updated kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances, butcher block countertops, tile backsplash, and a large peninsula that creates additional seating and workspace. The adjoining dining area opens to a charming sunroom that can be enjoyed year-round. Exposed brick accents, a wood-burning stove, and easy access to the kitchen make this a favorite gathering space for relaxing with family and friends. The main level offers four generously sized bedrooms, including a private primary suite with an updated bath featuring a walk-in glass shower and modern finishes. A conveniently located laundry area adds everyday practicality. One secondary bedroom showcases its own wood-burning fireplace, creating a cozy retreat ideal for guests, a home office, or hobby space. A second updated full bathroom serves the additional bedrooms and features stylish finishes, a double vanity, and a tiled tub/shower combination. Downstairs, the partially finished basement expands the home's living potential with a large recreation area centered around a striking brick fireplace. Whether used as a family room, game room, home gym, or media space, the possibilities are endless. An unfinished section provides ample storage space for seasonal items and equipment. Outside, mature trees frame the backyard, creating a peaceful setting for outdoor enjoyment. A rear patio, charming brick walkway, pergola, storage shed, oversized attached two-car garage, and expansive driveway complete the property, offering both functionality and outdoor appeal. With generous living space, desirable updates, and an exceptional Winchester location, this home is ready to welcome its next owners. Some photos have been virtually staged to illustrate potential furniture placement and room design

4 Beds ⋅ 2 Baths

Conveniently located in the heart of Winchester, this spacious brick ranch offers the perfect combination of timeless character, thoughtful updates, and flexible living space. Situated on a nearly half-acre corner lot, the property provides room to spread out while remaining just minutes from Winchester Medical Center, shopping, dining, and major commuter routes. Inside, you'll find beautiful hardwood flooring throughout much of the main level and an abundance of natural light pouring through oversized windows. The updated kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances, butcher block countertops, tile backsplash, and a large peninsula that creates additional seating and workspace. The adjoining dining area opens to a charming sunroom that can be enjoyed year-round. Exposed brick accents, a wood-burning stove, and easy access to the kitchen make this a favorite gathering space for relaxing with family and friends. The main level offers four generously sized bedrooms, including a private primary suite with an updated bath featuring a walk-in glass shower and modern finishes. A conveniently located laundry area adds everyday practicality. One secondary bedroom showcases its own wood-burning fireplace, creating a cozy retreat ideal for guests, a home office, or hobby space. A second updated full bathroom serves the additional bedrooms and features stylish finishes, a double vanity, and a tiled tub/shower combination. Downstairs, the partially finished basement expands the home's living potential with a large recreation area centered around a striking brick fireplace. Whether used as a family room, game room, home gym, or media space, the possibilities are endless. An unfinished section provides ample storage space for seasonal items and equipment. Outside, mature trees frame the backyard, creating a peaceful setting for outdoor enjoyment. A rear patio, charming brick walkway, pergola, storage shed, oversized attached two-car garage, and expansive driveway complete the property, offering both functionality and outdoor appeal. With generous living space, desirable updates, and an exceptional Winchester location, this home is ready to welcome its next owners. Some photos have been virtually staged to illustrate potential furniture placement and room design

1317 Caroline St, Winchester

Listing courtesy of Weichert Realtors - Blue Ribbon. Contact:

Selling Office: RE/MAX Roots.

$335,000

Welcome to 517 Dunlap St — a beautifully renovated 3-bedroom, 1.5-bath home set on a nicely sized, fully fenced lot in the heart of Winchester, where modern updates meet everyday comfort and a backyard designed for making the most of every season, complete with your own private pool. The main level welcomes you with a bright and inviting layout, where the living and dining spaces flow seamlessly together (the current LVP flooring is above the original oak hardwoods and could be restored if preferred)—creating a comfortable setting for both everyday living and entertaining. The kitchen shines with newer appliances and updated finishes, offering both style and functionality while remaining the heart of the home. New LVP flooring runs throughout, adding durability and a clean, cohesive look, while a conveniently located half bath enhances everyday convenience. Upstairs, you’ll find three well-proportioned bedrooms and a full bath, offering practical and efficient use of space with flexibility for a variety of living needs. The lower level provides useful utility and storage space, with laundry hookups already in place and room for additional organization or workshop-style use—an added bonus for functionality without taking away from the main living areas. Step outside to a backyard that truly sets this home apart—a fully fenced space with plenty of room to relax, entertain, and unwind, highlighted by a private pool that’s perfect for summer days and weekend gatherings. Whether hosting friends or enjoying a quiet evening, this outdoor space is ready to deliver. Major updates include a full interior renovation, new LVP flooring throughout, newer appliances (approximately 2 years old), a roof replaced approximately 3 years ago, and newly installed HVAC system with heat and AC (June 2026) Located in the City of Winchester, you’re just minutes from the charm of Old Town, with its shops, restaurants, walking mall, and year-round events, while still enjoying quick access to Route 7 and I-81 for an easy commute into Northern Virginia and beyond—all without the restrictions of an HOA.

3 Beds ⋅ 2 Baths

Welcome to 517 Dunlap St — a beautifully renovated 3-bedroom, 1.5-bath home set on a nicely sized, fully fenced lot in the heart of Winchester, where modern updates meet everyday comfort and a backyard designed for making the most of every season, complete with your own private pool. The main level welcomes you with a bright and inviting layout, where the living and dining spaces flow seamlessly together (the current LVP flooring is above the original oak hardwoods and could be restored if preferred)—creating a comfortable setting for both everyday living and entertaining. The kitchen shines with newer appliances and updated finishes, offering both style and functionality while remaining the heart of the home. New LVP flooring runs throughout, adding durability and a clean, cohesive look, while a conveniently located half bath enhances everyday convenience. Upstairs, you’ll find three well-proportioned bedrooms and a full bath, offering practical and efficient use of space with flexibility for a variety of living needs. The lower level provides useful utility and storage space, with laundry hookups already in place and room for additional organization or workshop-style use—an added bonus for functionality without taking away from the main living areas. Step outside to a backyard that truly sets this home apart—a fully fenced space with plenty of room to relax, entertain, and unwind, highlighted by a private pool that’s perfect for summer days and weekend gatherings. Whether hosting friends or enjoying a quiet evening, this outdoor space is ready to deliver. Major updates include a full interior renovation, new LVP flooring throughout, newer appliances (approximately 2 years old), a roof replaced approximately 3 years ago, and newly installed HVAC system with heat and AC (June 2026) Located in the City of Winchester, you’re just minutes from the charm of Old Town, with its shops, restaurants, walking mall, and year-round events, while still enjoying quick access to Route 7 and I-81 for an easy commute into Northern Virginia and beyond—all without the restrictions of an HOA.

517 Dunlap St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Non Subscribing Office.

$560,000

BEAUTIFUL NEW PRICE FOR A BEAUTIFUL HOUSE! ELEGANT AND SPECTACULAR! DRAMATIC SHOW STOPPER HOME IN MEADOW BRANCH SOUTH. If your passion is entertaining and fine living, this well-appointed, custom-built home is for you! Open floor plan with cathedral and multi-tiered tray ceilings, arches and plantation shutters. Fresh paint and newly refinished hardwood floors. In-town convenience near shopping, services and restaurants. A short drive to Winchester Medical Center and Old Town Winchester. Plenty of opportunities for exercise with a nearby city playground and green space and community walking/biking trails. Come inside to an inviting living room with a gas log fireplace. Adjoining kitchen offers granite countertops, a tile backsplash and newer stainless steel appliances. Two eating areas - a formal dining room with an intricate tray ceiling and chair rail plus an ample breakfast nook with bay windows overlooking the back yard. The primary bedroom is on the main level with a sitting area, large walk-in closet and ensuite bath with a walk-in shower, jetted tub, double vanities and a makeup area. Two more bedrooms on the main level plus two upstairs bedrooms, including a spacious room over the garage that could also be a home office or play area. The grounds have polished look - concrete driveway, beautiful landscaping with mature trees and shrubbery, and a tree-line at the rear for backyard privacy. Covered front porch. Trex deck with a pergola and a covered patio below plus a large brick patio at the rear. Bring your imagination to the ground-level, unfinished walk-out basement that opens to the patio. Plenty of possibilities for future living space in the basement with three large framed rooms that could be finished as an in-law suite with a full bath, game room, exercise room and home theater. Main-level laundry room off the two-car garage. Two-zone HVAC. Lawn watering system. New roof, new gas furnace, new gas hot water heater in 2025. Water softener not in use. Refrigerator icemaker as-is.

5 Beds ⋅ 3 Baths

BEAUTIFUL NEW PRICE FOR A BEAUTIFUL HOUSE! ELEGANT AND SPECTACULAR! DRAMATIC SHOW STOPPER HOME IN MEADOW BRANCH SOUTH. If your passion is entertaining and fine living, this well-appointed, custom-built home is for you! Open floor plan with cathedral and multi-tiered tray ceilings, arches and plantation shutters. Fresh paint and newly refinished hardwood floors. In-town convenience near shopping, services and restaurants. A short drive to Winchester Medical Center and Old Town Winchester. Plenty of opportunities for exercise with a nearby city playground and green space and community walking/biking trails. Come inside to an inviting living room with a gas log fireplace. Adjoining kitchen offers granite countertops, a tile backsplash and newer stainless steel appliances. Two eating areas - a formal dining room with an intricate tray ceiling and chair rail plus an ample breakfast nook with bay windows overlooking the back yard. The primary bedroom is on the main level with a sitting area, large walk-in closet and ensuite bath with a walk-in shower, jetted tub, double vanities and a makeup area. Two more bedrooms on the main level plus two upstairs bedrooms, including a spacious room over the garage that could also be a home office or play area. The grounds have polished look - concrete driveway, beautiful landscaping with mature trees and shrubbery, and a tree-line at the rear for backyard privacy. Covered front porch. Trex deck with a pergola and a covered patio below plus a large brick patio at the rear. Bring your imagination to the ground-level, unfinished walk-out basement that opens to the patio. Plenty of possibilities for future living space in the basement with three large framed rooms that could be finished as an in-law suite with a full bath, game room, exercise room and home theater. Main-level laundry room off the two-car garage. Two-zone HVAC. Lawn watering system. New roof, new gas furnace, new gas hot water heater in 2025. Water softener not in use. Refrigerator icemaker as-is.

813 Chelsea Dr, Winchester

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

Selling Office: Keller Williams Realty.

$332,000

Tucked away on a quiet cul-de-sac in the desirable Stonecrest Village community, 419 Stone Meadow Court offers a perfect blend of comfort, style, and convenience. Built in 1997 and thoughtfully maintained by its single in-residence owner, this charming home features easy one-level living with a spacious, light-filled layout ideal for both everyday living and entertaining. Recent updates include fresh interior paint, new kitchen flooring, a new HVAC system, and refreshed landscaping and mulch. Built by Oakcrest Builders, this unit is the Andover floor plan with the sunroom option, offering 1132 sq ft with carpeting throughout bedrooms and living/dining area. The galley-style kitchen is efficiently designed and updated with stainless steel appliances, vinyl flooring, and includes enclosed washer and dryer units. The open living and dining area creates an inviting space for gathering, with direct access to a private deck - perfect for relaxing or entertaining. A bright sunroom also opens to the fenced garden, offering a peaceful retreat filled with natural light. Generously sized bedrooms provide comfortable accommodations, while an oversized one-car garage and off-street parking for two additional vehicles add everyday convenience. Pull down attic access offers more storage. Residents of Stonecrest Village enjoy access to the community center, along with planned activities that foster a welcoming neighborhood atmosphere. HOA fees cover common grounds maintenance and landscaping, including snow removal and street maintenance, adding ease and convenience to daily living. Conveniently located within Winchester City, this home is just minutes from local shops, dining, parks, and commuter routes, delivering the best of low maintenance living in a prime location. With just 34 homes in the community, it is truly a hidden gem! Please note: the owner requests that you kindly remove your shoes when viewing, or utilize the provided booties. White carpeting has just been cleaned.

2 Beds ⋅ 1 Baths

Tucked away on a quiet cul-de-sac in the desirable Stonecrest Village community, 419 Stone Meadow Court offers a perfect blend of comfort, style, and convenience. Built in 1997 and thoughtfully maintained by its single in-residence owner, this charming home features easy one-level living with a spacious, light-filled layout ideal for both everyday living and entertaining. Recent updates include fresh interior paint, new kitchen flooring, a new HVAC system, and refreshed landscaping and mulch. Built by Oakcrest Builders, this unit is the Andover floor plan with the sunroom option, offering 1132 sq ft with carpeting throughout bedrooms and living/dining area. The galley-style kitchen is efficiently designed and updated with stainless steel appliances, vinyl flooring, and includes enclosed washer and dryer units. The open living and dining area creates an inviting space for gathering, with direct access to a private deck - perfect for relaxing or entertaining. A bright sunroom also opens to the fenced garden, offering a peaceful retreat filled with natural light. Generously sized bedrooms provide comfortable accommodations, while an oversized one-car garage and off-street parking for two additional vehicles add everyday convenience. Pull down attic access offers more storage. Residents of Stonecrest Village enjoy access to the community center, along with planned activities that foster a welcoming neighborhood atmosphere. HOA fees cover common grounds maintenance and landscaping, including snow removal and street maintenance, adding ease and convenience to daily living. Conveniently located within Winchester City, this home is just minutes from local shops, dining, parks, and commuter routes, delivering the best of low maintenance living in a prime location. With just 34 homes in the community, it is truly a hidden gem! Please note: the owner requests that you kindly remove your shoes when viewing, or utilize the provided booties. White carpeting has just been cleaned.

419 Stone Meadow Ct, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$590,000

Welcome to 1613 Van Couver St. in the sought-after Williamsburg Heights neighborhood, just minutes from downtown Winchester. This well-maintained colonial offers 4 bedrooms and 2.5 baths with timeless charm and modern comfort throughout. Step into the inviting foyer featuring gorgeous hardwood floors that flow through most of the home. French doors lead to a spacious family room, while the cozy living room showcases a wood-burning fireplace. The gourmet kitchen is equipped with stainless steel appliances, granite countertops, abundant cabinetry, and space for both table seating and counter seating. A separate formal dining room is perfect for gatherings. Upstairs, the spacious primary suite features an ensuite bath and a large walk-in closet. Three additional bedrooms offer generous space and flexibility. The finished lower level provides endless potential for additional living space, along with a large utility room with shelving—ideal for storage or a workshop. Walk out to the patio and enjoy the fully fenced backyard. Outdoor living shines with a sunroom, deck, and beautifully landscaped, low-maintenance yard. An oversized 2-car garage and concrete driveway provide ample parking. Conveniently located near the hospital, schools, shopping, and commuter routes.

4 Beds ⋅ 3 Baths

Welcome to 1613 Van Couver St. in the sought-after Williamsburg Heights neighborhood, just minutes from downtown Winchester. This well-maintained colonial offers 4 bedrooms and 2.5 baths with timeless charm and modern comfort throughout. Step into the inviting foyer featuring gorgeous hardwood floors that flow through most of the home. French doors lead to a spacious family room, while the cozy living room showcases a wood-burning fireplace. The gourmet kitchen is equipped with stainless steel appliances, granite countertops, abundant cabinetry, and space for both table seating and counter seating. A separate formal dining room is perfect for gatherings. Upstairs, the spacious primary suite features an ensuite bath and a large walk-in closet. Three additional bedrooms offer generous space and flexibility. The finished lower level provides endless potential for additional living space, along with a large utility room with shelving—ideal for storage or a workshop. Walk out to the patio and enjoy the fully fenced backyard. Outdoor living shines with a sunroom, deck, and beautifully landscaped, low-maintenance yard. An oversized 2-car garage and concrete driveway provide ample parking. Conveniently located near the hospital, schools, shopping, and commuter routes.

1613 Van Couver St, Winchester

Listing courtesy of Re/Max Roots. Contact:

Selling Office: NextHome Realty Select.

$429,000

Opportunity is knocking! This 3-unit multifamily property is centrally located in downtown Winchester, just minutes from the Walking Mall. The property is fully occupied and offers immediate rental income with strong upside potential. The property currently has a long term tenants with leases as follows: One month-to-month tenant , One tenant with a lease ending June 5, 2026 , One tenant with a lease ending March 14, 2027. All three units offer the potential for rent increases, providing an excellent value-add opportunity for investors. Conveniently located near shopping, dining, entertainment, and downtown amenities, this property is well-positioned for long-term growth and cash flow.

406-408 S Cameron St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Pearson Smith Realty LLC.

$490,000

Exceptional 5-bedroom, 3 full bath home offering space, comfort, and numerous updates—all with NO HOA! This beautifully maintained property combines functional living spaces with charming details throughout. Major improvements include a roof approximately 5 years old, heating and cooling systems replaced approx. 3 years ago, and several newer windows for added efficiency and peace of mind. Step inside through the impressive 2-story foyer featuring hardwood flooring and an inviting layout designed for both everyday living and entertaining. The main level includes a convenient bedroom and full bath, ideal for guests, multigenerational living, or a private home office setup. A dedicated office with elegant glass doors provides the perfect work-from-home space, while the separate formal dining room is ready for gatherings and special occasions. The spacious family room is warm and welcoming, featuring a fireplace with a beautiful mantle that creates a cozy focal point. The thoughtfully designed kitchen offers soft-close cabinetry, tile backsplash, a center island, and not one but two pantry spaces providing exceptional storage and organization. Adjacent to the kitchen, the lovely sunroom is filled with natural light and showcases custom built-ins, blackout blinds, and sliding glass doors leading directly to the rear deck. Outdoor living is equally enjoyable with raised garden beds for gardening enthusiasts and a peaceful backyard pond that adds beauty and tranquility to the setting. The backyard creates a relaxing retreat perfect for entertaining, enjoying nature, or unwinding at the end of the day. This spacious and well-cared-for home offers the perfect blend of updates, character, and functionality in a desirable no-HOA setting.

5 Beds ⋅ 3 Baths

Exceptional 5-bedroom, 3 full bath home offering space, comfort, and numerous updates—all with NO HOA! This beautifully maintained property combines functional living spaces with charming details throughout. Major improvements include a roof approximately 5 years old, heating and cooling systems replaced approx. 3 years ago, and several newer windows for added efficiency and peace of mind. Step inside through the impressive 2-story foyer featuring hardwood flooring and an inviting layout designed for both everyday living and entertaining. The main level includes a convenient bedroom and full bath, ideal for guests, multigenerational living, or a private home office setup. A dedicated office with elegant glass doors provides the perfect work-from-home space, while the separate formal dining room is ready for gatherings and special occasions. The spacious family room is warm and welcoming, featuring a fireplace with a beautiful mantle that creates a cozy focal point. The thoughtfully designed kitchen offers soft-close cabinetry, tile backsplash, a center island, and not one but two pantry spaces providing exceptional storage and organization. Adjacent to the kitchen, the lovely sunroom is filled with natural light and showcases custom built-ins, blackout blinds, and sliding glass doors leading directly to the rear deck. Outdoor living is equally enjoyable with raised garden beds for gardening enthusiasts and a peaceful backyard pond that adds beauty and tranquility to the setting. The backyard creates a relaxing retreat perfect for entertaining, enjoying nature, or unwinding at the end of the day. This spacious and well-cared-for home offers the perfect blend of updates, character, and functionality in a desirable no-HOA setting.

3017 Saratoga Dr, Winchester

Listing courtesy of Re/Max Roots. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

$309,000

Welcome home to 1026 S. Kent Street, a charming and well-maintained property that blends timeless character with thoughtful updates. Beautiful hardwood floors flow throughout the home, creating warmth and continuity in every room. The kitchen features durable Corian countertops and newer appliances, making it both functional and inviting for everyday living and entertaining. Improvements provide peace of mind, including quality Andersen windows and exterior paint completed within the last four years. Outside, you'll appreciate the home's attractive curb appeal and convenient Winchester location close to shopping, dining, schools, and commuter routes. This move-in ready home offers the perfect combination of classic charm, modern updates, and pride of ownership throughout. Don't miss the opportunity to make this Winchester gem your next home.

2 Beds ⋅ 2 Baths

Welcome home to 1026 S. Kent Street, a charming and well-maintained property that blends timeless character with thoughtful updates. Beautiful hardwood floors flow throughout the home, creating warmth and continuity in every room. The kitchen features durable Corian countertops and newer appliances, making it both functional and inviting for everyday living and entertaining. Improvements provide peace of mind, including quality Andersen windows and exterior paint completed within the last four years. Outside, you'll appreciate the home's attractive curb appeal and convenient Winchester location close to shopping, dining, schools, and commuter routes. This move-in ready home offers the perfect combination of classic charm, modern updates, and pride of ownership throughout. Don't miss the opportunity to make this Winchester gem your next home.

1026 S Kent St, Winchester

Listing courtesy of Crum Realty, Inc.. Contact:

Selling Office: Crum Realty, Inc..

$188,000

968 sf of B2 space in Opequon Center. Very clean and well maintained condo. One private office and one bathroom - open space with carpet. Condo fees $184 per month. Easy to rent out makes this unit ideal for investors. Call broker for a tour.

3042 Valley Ave Unit 104, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

Selling Office: Funkhouser Real Estate Group.

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