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104 Monet Ter, Winchester
$549,999
4 Beds ⋅ 3 Baths
Opportunities like this don't come around often! Lovingly owned and cared for by the original owners for over 20 years, this beautiful brick Colonial in a highly desirable, established Winchester neighborhood is ready for its next chapter. Step inside to a welcoming foyer and discover a home filled with character, timeless charm, and tons of natural light. Hardwood floors, crown molding, chair rail, and wainscoting add warmth and character throughout the main level. The main level also features a formal dining room, a dedicated office, and a spacious kitchen with Corian countertops, abundant cabinetry, and an archway pass-through. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite with a private bath and large walk-in closet, along with a full hall bathroom and convenient upper-level laundry. The walk-up basement offers additional storage and a blank canvas with endless possibilities to create a space that suits your needs. Additional features include dual-zone HVAC with two gas furnaces and a deep two-car garage. Outside, enjoy a front deck, a covered rear porch overlooking the huge, private fenced backyard, and a 10x12 storage shed. Residents can also enjoy the neighborhood pool, perfect for relaxing and cooling off during the warmer months. Tucked away on a cul-de-sac, this home offers a wonderful combination of privacy, space, and timeless character, all just minutes from downtown Winchester, Shenandoah University, Jim Barnett Park, and Winchester Country Club. After more than two decades of making memories here, these owners are ready to pass the keys to someone new. Don't miss this opportunity to own a beautiful, well-loved brick Colonial in a fantastic location!

104 Monet Ter, Winchester

Listing courtesy of Colony Realty. Contact:

709 Ross St, Winchester
$394,900
3 Beds ⋅ 3 Baths
Pretty as a Picture. Designed for Peace of Mind. With its gorgeous sage-green siding, welcoming paver walkway, and thoughtfully landscaped exterior, this beautiful new-construction home makes a wonderful first impression. Step inside to an open living and dining area that feels connected and inviting, complemented by a kitchen with granite countertops and the everyday convenience of a main-level powder room, laundry, and attached one-car garage. The Kitchen is very spacious with lots of prep space and is highlighed with Brand New stainless appliances and handy breakfast bar area. Served by a large dining area, this space is light and bright with sunny windows and contemporary lighting. Upstairs, you'll find three comfortable bedrooms, including a Private Primary bedroom with it's own private bath and 2 large closets, along with a second full hall bath. Outside, the level backyard offers room to relax, garden, entertain, or simply enjoy a little fresh air. And the front porch is inviting you for a morning cup of coffee to take in the sights of this lovely neighborhood. Located in Frederick County but throw a rock and it will land in Winchester giving you the benefit of convenience with Fred Co taxes. Minutes from Jim Barnett Park, Restaurants, Winchester's Old Town Mall, commuter routes, Winchester Medical Center, and shopping...this affordable New Construction has it all. From its charming curb appeal to its practical layout, this home offers the fresh start of new construction, modern comfort, and the peace of mind that comes with a Brand New Home. Come see how beautiful a fresh start can be at 709 Ross Street.

709 Ross St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

318 Stonehenge Rd, Winchester
$399,900
3 Beds ⋅ 2 Baths
Looking for a ranch-style home with plenty of potential and NO HOA? Offered for the first time by its original owner, this home offers convenient main-level living plus a finished bonus room above the garage, accessed by interior stairs located just off the kitchen. This additional finished space offers plenty of flexibility for a home office, hobby room, playroom, or whatever best fits your needs. Inside, you’ll find hardwood flooring in the foyer and living room, along with a gas fireplace that adds warmth and character to the main living space. The spacious primary suite features a walk-in closet, jetted tub, and an upgraded tiled walk-in shower with a built-in seat. A ramp at the front entrance provides easier access into the home. Outside, enjoy the spacious backyard, along with the convenience of an attached 2-car garage. The most recent updates that have already been completed are the HVAC system replaced in 2019 and a roof that was replaced approximately 6-7 years old. This home is being sold AS-IS and has been priced with its current condition in mind. While there are cosmetic updates a new owner may want to make, the home is move-in ready and can be enjoyed as it is today, allowing you to make updates and personal touches over time. It’s a great opportunity to move in, settle in, and make the home your own at your own pace. Convenient Winchester location close to restaurants, shopping and highways.

318 Stonehenge Rd, Winchester

Listing courtesy of NextHome Realty Select. Contact:

411 Mosby St, Winchester
$429,900
3 Beds ⋅ 1 Baths
Welcome home to this charming all-brick rancher, offering timeless appeal, beautiful hardwood floors throughout, and wonderful potential to make it your own! The inviting living room features a wood-burning fireplace, while the dining area provides a comfortable space for everyday meals and entertaining. The updated kitchen boasts granite countertops, and the remodeled bathroom adds a fresh, modern touch. Enjoy relaxing in the sun porch or entertaining outdoors on the stamped concrete patio, surrounded by gorgeous mature trees in the backyard. Replacement windows and architectural shingles, approximately nine years old, provide additional peace of mind. The walk-up attic offers exciting possibilities for additional living space, while the unfinished basement features a rough-in for a future bathroom and the opportunity to expand your finished living area. With three bedrooms, classic brick construction, and room to grow, this home is full of possibilities. Don't miss the opportunity to make it yours!

411 Mosby St, Winchester

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

317 S Kent St, Winchester
$399,000
4 Beds ⋅ 2 Baths
Welcome to this charming brick home located in the heart of Winchester! Filled with historic character, this home features beautiful hardwood floors throughout, spacious living areas, and oversized bedrooms. Enjoy relaxing on the covered front porch or entertaining on the covered back porch overlooking the large backyard. The home's timeless charm and generous room sizes offer a wonderful opportunity to make it your own. Location is a highlight! Situated right next to Ruth Jackson Memorial Park, within walking distance of Patsy Cline Memorial Park, and directly across the street from the Green Circle Trail, you'll have easy access to walking, biking, and outdoor recreation. Plus, you're just a short stroll from local shops, restaurants, Shenandoah University, and all that downtown Winchester has to offer. Historic charm, spacious living, and a fantastic location make this home a wonderful opportunity!

317 S Kent St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

115 Ware Pl, Winchester
$399,900
3 Beds ⋅ 2 Baths
Beautifully updated and ready for its next owner! This three-bedroom, two-bath home on Winchester’s desirable east side features fresh paint throughout, new luxury vinyl flooring, and new carpet. The refreshed kitchen shines with new quartz countertops and stainless steel appliances, while new light fixtures add a stylish finishing touch. Both bathrooms have been completely renovated, bringing a fresh, modern feel to the home. The unfinished lower level offers ample room for storage, hobbies, or future expansion. Enjoy outdoor living on the deck and make the backyard your own retreat. Conveniently located near shopping, dining, Route 7, and I-81, this home combines thoughtful updates with everyday convenience. Schedule your showing today!

115 Ware Pl, Winchester

Listing courtesy of Compass West Realty, LLC. Contact:

182 Front Dr, Winchester
$429,900
3 Beds ⋅ 2 Baths
Seller-paid interest rate buy down may be available to buyer with acceptable offer, subject to lender credit approval and program guidelines. Please inquire with listing agent for more details. Come check out this Lovely Brick Rancher in an older, established neighborhood close to shopping and commuting. The home is in great condition, recently painted, with new laminated flooring and brand-new appliances. All-brick home that has been meticulously taken care of. Three bedrooms with two baths, including a full, partially finished basement. Huge rec room perfect for a Theater room or man cave. The living room includes a gas fireplace, gas tank would need to be installed. Off the kitchen is a large family room for entertaining. Would also make a perfect sitting room and dining room. The basement has a really nice Rec Room and was remodeled in 2016. A nice flat lot (almost a half acre) with a deck for enjoying the beautiful fall evenings. There is one car garage and a good-size driveway. Roof was put on in 2019 and HVAC was 2016. New Hot water heater in 2024. New Washer and dryer in 2023. In 2026 the basement was waterproofed and a new well pump was installed. Home has both city and a well but the sellers did not use the well. Septic is connected to the city. On the HVAC system when it's 25 degrees out, the oil furnace will automatically cut on. There is a main-level laundry. Washer and Dryer is set up in the Basement but could be moved. All that's left is to move in.

182 Front Dr, Winchester

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

718 Academy Cir, Winchester
$673,000
6 Beds ⋅ 4 Baths
$10K Credit Considered w/ Acceptable Offer - Come Take A Look! Quiet Brick Cape Cod in the heart of Winchester, VA with over 4,000sqft and 6 bedrooms, there is plenty of space for everyone - growing family or combining house holds. 2 bedrooms on main level, 3 fireplaces - colonial style gas in the living room, brick gas in the kitchen, and brick wood burning in the basement. A concrete in-ground pool with built-in entry stairs in the 3 ft shallow end and a built-in sitting shelf in the 9ft deep end. A jumping stone makes for a interesting natural feature that just blends into the landscaping of the backyard oasis. The laundry room is ready to be converted into a kitchenette to further help with combined households. Even with all the finished space in the basement there is still ample storage space. So many ways to enjoy this home: swinging on the front porch watching the world go by, cooking holiday meals in the enormous kitchen, sitting by the fire reading a book, hours swimming in the pool with patio cook-outs. All of this is minutes away from all the necessities of life: shopping, hospital, schools, downtown dining and festivals, museums, trails. As quiet as it is, it is hard to believe you really are in the heart of Winchester. Between the spacious rooms, mid-century craftmanship, and numerous features, you can make this your home for generations to fully enjoy all of what Winchester has to offer.

718 Academy Cir, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

115 Garnett Ct, Winchester
$859,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully crafted new construction home offering approximately 2,400 square feet of high-quality living space, perfectly situated on 2 peaceful acres at the end of a desirable cul-de-sac. Step inside to a thoughtfully designed floor plan filled with natural light and stylish finishes. The kitchen, designed to be the heart of the home, also features a walk-in pantry complete with a sink and under-counter refrigerator, providing storage and functionality for everyday living and entertaining. A charming breakfast nook offers the perfect spot for casual meals, while the separate dining room provides an inviting setting for holidays, dinner parties, and special occasions. The generous living spaces are complemented by well-appointed bedrooms and bathrooms, creating a comfortable and functional home for both everyday living and entertaining. The home also features an unfinished walk-out basement, offering abundant potential for future finished living space, a home gym, recreation room, workshop, or additional storage. Customize it to suit your needs and add even more value to this already exceptional property. Outside, enjoy the freedom and privacy that come with 2 acres, while the cul-de-sac setting provides a quiet, low-traffic environment. Whether you're relaxing outdoors, entertaining guests, or simply enjoying the surrounding space, this property offers room to live, grow, and unwind.

115 Garnett Ct, Winchester

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

1 Swansong Pl Unit TEAGAN 24-F2, Winchester
$399,990
3 Beds ⋅ 4 Baths
New personalized TOWNHOMES by Van Metre Homes at SNOWDEN BRIDGE in Stephenson, VA that will be ready for move in MID 2027 based on build time. Discover the Teagan 24-F2—a two-car, front-load garage townhome with three bedrooms, two full bathrooms, and two half bathrooms. Thoughtfully designed, this townhome makes every day extraordinary—from the lower-level walkout rec room, perfect for relaxation or entertainment to the heart-of-the-home kitchen with a walk-in pantry and a cozy reading nook. The primary suite features an oversized walk-in closet for added comfort and organization, making this home a perfect blend of space and convenience. The Teagan 24-F2 offers build-to-order opportunities on select homesites, allowing you to personalize your new home. Explore a variety of professionally curated interior design packages at different price points to match your style and budget. Certain homesites also offer optional structural enhancements. Contact a Van Metre New Home Advisor to learn how you can bring your vision to life! Being a new build, your home is constructed to the highest energy efficiency standards, comes with a post-settlement warranty, and has never been lived in before! Take advantage of closing cost assistance by choosing Intercoastal Mortgage and Walker Title. Self-schedule a tour today by visiting our website! ----NterNow self-touring is available on select homesites at Snowden Bridge, no agent or appointment required. Buyers may visit independently during daylight hours. For access instructions and availability, contact a Van Metre New Home Advisor directly or visit our website. ------Experience life at Snowden Bridge, a premier master-planned community minutes from Downtown Winchester, where stunning Shenandoah Valley views and endless possibilities await. This vibrant neighborhood offers unparalleled amenities for every lifestyle, from a 15,000-square-foot indoor sportsplex to refreshing swimming pools, playgrounds, scenic paved trails, and more. Families enjoy the convenience of an onsite daycare center and elementary school, while a dog park and picnic pavilion add to the charm. Perfectly situated near major commuter routes like Route 7, I-81, and I-66, Snowden Bridge keeps you effortlessly connected to Northern Virginia. Here, modern conveniences meet a warm, welcoming community, making it the perfect place to call home. -----*Other homes sites and delivery dates may be available. Pricing, offers, and availability are subject to change without notice. Images, renderings, and site plans are for illustrative purposes only and may not reflect actual homes or features. Some renderings may depict a similar home. Additional Terms and Conditions may apply. Please see a Van Metre New Home Advisor for details.

1 Swansong Pl Unit TEAGAN 24-F2, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

114 Princeton Dr, Winchester
$445,000
3 Beds ⋅ 2 Baths
Welcome to 114 Princeton Drive, a beautifully maintained custom-designed brick ranch offering over 2,000 square feet of comfortable one-level living on nearly half an acre in Winchester. This spacious 3-bedroom, 2-full-bath home offers a thoughtfully designed floor plan with plenty of room to relax, entertain, and enjoy everyday living. Warm bamboo hardwood flooring adds character throughout, while the kitchen features Corian countertops and generous workspace. The inviting living room is enhanced by a built-in bookcase, and a separate laundry room adds everyday convenience. One of the highlights of the home is the impressive 16' x 20' sunroom—an ideal spot for morning coffee, relaxing with a good book, or enjoying the backyard throughout the seasons. Step outside to a 16' x 22' Trex deck with a shade sail overlooking the level, privacy-fenced backyard. A separate BBQ and grilling area with electric makes outdoor entertaining easy. The newer storage shed also has electric, providing additional space for hobbies, lawn equipment, or storage. The attached two-car garage offers even more than parking, with a workshop area, additional bump-out space, and a high-powered electric heater—perfect for projects and year-round use. The home has been exceptionally cared for with valuable recent improvements, including a new roof in 2023, new HVAC system in 2024, new exterior paint in 2022, a new shed with electric in 2022, and approximately 18 inches of additional attic insulation added in 2022. Enjoy the space and privacy of an almost half-acre lot while remaining close to everything Winchester has to offer. Downtown Winchester, shopping, restaurants, hotels, and everyday conveniences are just minutes away, with easy access to Route 50, I-81, and I-66 for commuters. Spacious, well maintained, and designed for easy one-level living, 114 Princeton Drive offers the combination of indoor comfort, outdoor living, storage, no HOA and convenience to everything.

114 Princeton Dr, Winchester

Listing courtesy of Samson Properties. Contact:

220 E Cork St, Winchester
$449,000
Situated near the heart of historic downtown Winchester, 220 E Cork Street offers an exceptional commercial opportunity in close proximity to the iconic walking mall, putting your business right in the stream of the area's top dining, shopping and local attractions on a main artery into the City. Featuring a classic brick exterior bursting with character, this versatile property combines timeless historic charm with everyday convenience, complete with easy access and ample parking right out front. The main level boasts a light-filled, expansive open layout accented by updated flooring and a stylish exposed brick wall—offering incredible potential for a welcoming reception area, retail storefront, client showroom or collaborative workspace. The storage/break room is adjacent to this space with two bathrooms The lower level extends the functional footprint with multiple private rooms and dedicated office spaces—a layout perfectly suited for professional suites, administrative headquarters or an attorney’s office situated just blocks from the courthouse. Positioned to take full advantage of everything downtown Winchester has to offer, this adaptable space delivers high visibility, functional flexibility and endless potential for your business.

220 E Cork St, Winchester

Listing courtesy of Colony Realty. Contact:

615 Mahlon Dr, Winchester
$675,000
4 Beds ⋅ 3 Baths
Welcome to 615 Mahlon Drive, Winchester, VA. Custom-built 2023 home offering the perfect blend of modern comfort, thoughtful upgrades, privacy, and country living on 5 unrestricted, peaceful acres. Conveniently located approximately 6 miles from Walmart and the medical center, this property offers a private rural setting with convenient access to Winchester and the beautiful Shenandoah Valley. Featuring 4 bedrooms, 2.5 bathrooms, a desirable main-level primary suite, and an open-concept floor plan, this home is designed for comfortable everyday living and effortless entertaining. The spacious kitchen features upgraded granite countertops, a large center island, and a premium selection of appliances, flowing seamlessly into the main living area. A propane fireplace adds warmth, creating an inviting space to relax and unwind. The main-level primary suite offers the convenience of one-level living, while the additional bedrooms provide flexibility for family, guests, or a home office. The full, mainly unfinished walk-out basement presents an exceptional opportunity to expand your living space with a future recreation room, home gym, workshop, additional storage, or other custom uses. A two-car garage adds everyday convenience. Enjoy the outdoors from the large, covered wraparound porch, where you can take in the peaceful surroundings, entertain guests, or enjoy a quiet morning overlooking your acreage. With 5 acres of privacy and open space, there is room to explore, garden, relax, and make the property your own. This home features an impressive collection of upgraded mechanical systems, electrical infrastructure, and smart-home-ready features. Enjoy the balance of peaceful country living and access to the amenities of Winchester and the surrounding Shenandoah Valley. Nearby attractions include Old Town Winchester's historic pedestrian mall, local dining and shopping, the Museum of the Shenandoah Valley, the Shenandoah Valley Discovery Museum, historic Civil War sites, and outdoor recreation throughout the region. Commuters benefit from access to I-81, Route 7, Route 50, Route 522, and Route 37, connecting the Winchester area with Northern Virginia and the greater Washington, DC region. Winchester is approximately 72 miles northwest of Washington, DC.

615 Mahlon Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

432 N Loudoun St, Winchester
$699,000
4 Beds ⋅ 3 Baths
432 North Loudoun Street sits a half block up from the historic fort and 2 blocks from the Winchester Mall. This completely redeveloped 1915 Craftsman style house in Winchester’s emerging historic district masterfully combines modern purpose with a classic feel using a sustainable redevelopment design. It is a custom home within a historical exterior, offering all the experiences of new construction. This is a high-quality residence for building your life with its 4 bedrooms, 2 ½ bath, dual street access, including a full fenced-in yard with landscaped patio, hot tub, and 10x8 shed. The floor plan is built around original hand-scraped hardwoods, handcrafted Craftsman style door moldings, an abundance of windows, period staircases, and a stunning new main bedroom/kitchen/family room addition to name a few of the fine features. Upstairs has the owner suite with walk-in closet and full bathroom; additional features include two bedrooms, a wired office, laundry center, and full bath. Presenting wide-ranging features from the mahogany front porch to the custom-built basement staircase to the new addition owner’s suite 432 Loudoun showcases quality is a requirement not a luxury.

432 N Loudoun St, Winchester

Listing courtesy of The Greene Realty Group. Contact:

2310 Senseny Rd, Winchester
$320,000
3 Beds ⋅ 1 Baths
**Great investor opportunity or starter home.** This solid 1960s property has the dependable construction of its era and the lived‑in charm of a home cared for over six decades. Like many homes of its age, it shows some wear, but a little “nip and tuck” will easily bring back its shine. You’ll be only the **second owner** of this sweet little gem. The original owners purchased it 60 years ago—before their youngest daughter was born—and her childhood drawings still remain on a closet wall, a sentimental reminder of the home’s history. Recent improvements include an **updated bathroom** with a walk‑in shower and new flooring, **fresh paint** throughout the main living areas, and **new outlets and covers** will be installed on the main floor. The kitchen features **stainless steel appliances** including the stove, refrigerator, and dishwasher. The **partially finished basement** offers versatile space: one side served as a music room with a dry bar, while the other side includes laundry, storage, a tinkering area, a wood‑burning stove connected to the furnace, and an additional multi-purpose room . All windows have been updated to **double‑hung replacements**. Outside, the **large front yard** sets the home back from the road and provides generous parking. The backyard has been lovingly maintained over the years with raised garden beds, a greenhouse, two carports, and a storage shed perfect for lawn equipment. Seasonal flower beds surround the home. The roof was replaced in 2021, and while the HVAC system has backup heat, the owners primarily used the woodstove in the basement. Only kitchen appliances convey; all other items will be cleared out prior to closing. **Home is being sold AS‑IS. Any inspections are to be for informational purposes only.**

2310 Senseny Rd, Winchester

Listing courtesy of NextHome Realty Select. Contact:

310.87/- Acres Off Laurel Grove Rd, Winchester
$1,699,000
OUTSTANDING 310+/- ACRES IN WINCHESTER, VA – BEAUTIFUL VIEWS, EXCELLENT HUNTING, AND INCREDIBLE OPPORTUNITY! These two adjoining properties offer a rare opportunity to own approximately 310+/- acres in a beautiful and private setting just minutes from Winchester. With beautiful views, streams, wooded land, open land, approved perc sites, and excellent hunting opportunities, these properties offer endless possibilities for a dream home, cabin, recreational property, or private country estate. Tract 1: 152± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property features beautiful views, a cleared building site, an approved five-bedroom perc site, and electric has been run to the property, providing an excellent foundation for future development. Outdoor enthusiasts will appreciate the great hunting opportunities, with abundant wildlife including deer, turkey, and more. A stream flows through the property, adding to the natural beauty and creating a peaceful setting. An established road provides access into the property, with access from a deeded right-of-way off Laurel Grove Road. Located just 13 miles from Winchester and less than 9 miles from I-81 and Route 11, the property offers convenient access for commuting while maintaining a private, rural setting. Dulles International Airport is approximately 80 minutes away, with Washington, D.C. approximately 90 minutes away. Whether you're looking to build a home or cabin, enjoy great hunting, or create your own private getaway, this property offers an exceptional opportunity. Come and make this your next great adventure! Buyer is responsible for all due diligence regarding building suitability, permits, zoning, permitted uses, utilities, and any other intended use of the property. Tract 2: 158.43± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property features beautiful views, a cleared building site, an approved five-bedroom perc site, and electric is near to the property, providing an excellent foundation for future development. Outdoor enthusiasts will appreciate the great hunting opportunities, with abundant wildlife including deer, turkey, and more. A stream flows through the property, adding to the natural beauty and creating a peaceful setting. An established road provides access into the property, with access from a deeded right-of-way off Laurel Grove Road. Located just 13 miles from Winchester and less than 9 miles from I-81 and Route 11, the property offers convenient access for commuting while maintaining a private, rural setting. Dulles International Airport is approximately 80 minutes away, with Washington, D.C. approximately 90 minutes away. Whether you're looking to build a home or cabin, enjoy great hunting, or create your own private getaway, this property offers an exceptional opportunity. Come and make this your next great adventure! Buyer is responsible for all due diligence regarding building suitability, permits, zoning, permitted uses, utilities, potential utility projects, and any other intended use of the property. The property is crossed by existing power lines, and there may be a project to add an additional power line to the existing lines. At this time, the potential project has not been confirmed, and buyers should conduct their own due diligence regarding any proposed utility projects.

310.87/- Acres Off Laurel Grove Rd, Winchester

Listing courtesy of Hurley Real Estate & Auctions. Contact:

23 Jigsaw Pl, Winchester
$229,000
2 Beds ⋅ 2 Baths
Affordable homeowership opportunity in city limits. This town home has been cared for by owner for 35 years. Just needs some TLC to make it your own style. Living & dining with hardwood flooring. Bright kitchen with pantry and all appliances to convey. Plenty of storage with coat closet, 2 utility closets & hall closet. Laundry with shelving and space for freezer or more cabinety. Both bedroooms have double wide closets with double doors. 2 Liquid solar walls are an 80's system of plastic wall panels with internal liquid heated by sun to heat room. Owner has maintained regular servicing for gas heat & central AC. Private back yard with fencing . Not a thoroughfare street. Located convenient to dining, schools, retail, parks & rec, Green Circle Trail, just minutes to Shenandoah Universiry, the medical center, Apple Blossom Mall & Downtown Loudoun Street Walking Mall & commute routes 7, 81 and 37. Call today for a private tour

23 Jigsaw Pl, Winchester

Listing courtesy of Coldwell Banker Elite. Contact:

999 Dicks Hollow Rd, Winchester
$412,500
3 Beds ⋅ 3 Baths
Experience effortless main-level living in this charming rancher set on over an acre of scenic, usable land. Inside, an inviting open-concept layout connects the primary living spaces, creating an ideal setting for both everyday life and hosting guests. The split-bedroom design ensures total privacy, placing the spacious primary suite in its own wing, separated from the generously sized secondary bedrooms. Downstairs, a finished walk-out basement provides a versatile recreation room that significantly expands your living and entertaining area. Step out from the family room onto an expansive rear deck overlooking your private backyard—the ultimate backdrop for summer barbecues, lawn games, and quiet evenings outdoors.

999 Dicks Hollow Rd, Winchester

Listing courtesy of Real Broker, LLC. Contact:

3336 Hunting Ridge Rd, Winchester
$524,990
5 Beds ⋅ 3 Baths
Colonial home 21 yrs young on 5 acres in Frederick county 4 bedroom 2 full baths with 1 half bath ., Whole house freshly painted in Jan/Feb 2025, laundry on main level with large pantry and large eat in kitchen with breakfast bar, granite countertops (new in Jan/Feb 2025) Family room formal dining room and living room (currently being used as a dining room) Large flat back yard with above ground pool with decking surround and pool house and BBQ deck for gathering. Pool house has electricity and TV connections . Carpet on Bedroom (new in Jan Feb 2025) level, Large Primary bedroom with ensuite bath with soaking tub and shower stall and double sink and walk in closet. hall bath has 2 sinks. all bedrooms have ceiling fans. Basement has a legal size bedroom rough in and a bath rough-in in the corner by the electric panels. Hot Water Heater replaced in 2024. Well Filter was installed in approx Sept 2025 (Lancaster Iron Filter Service) 2 car garage rear entry and inside entrance to the basement . two 200amp electric panels for plenty of expansion for electrical usage. AND house wired with CAT 5 wiring. Private Well, and Private Septic in Jan/Feb 2025 2 new Tanks , drain lines and Distribution Box Pool house has mini split for AC/Heat, mounted TV, Luxury Vinyl Plank flooring, 2 ceiling fans, Anderson wood windows double pane with a deck area for grilling, storage under pool house for equipment

3336 Hunting Ridge Rd, Winchester

Listing courtesy of Carter Real Estate, Inc.. Contact:

Lot 5 Shuoner, Winchester
$359,990
3 Beds ⋅ 3 Baths
🏡 Your New Home Is Move-In Ready! Discover the St. Paul Townhome, featuring 3 bedrooms, 2.5 bathrooms, a 1-car garage, and a finished lower level—with up to 2,000 sq. ft. of space to make your own. 🌳 Beautiful wooded homesites available! ✨ Room to Gather Enjoy an open-concept main level with granite countertops, stainless steel appliances, and luxury vinyl plank flooring throughout. Whether you’re hosting friends or enjoying a quiet evening at home, this space brings everyone together. 🛌 A Place to Unwind Your primary suite features a spacious walk-in closet and a Deluxe Silver bath with a rain shower. Two additional bedrooms, a full bath, and bedroom-level laundry keep everyday living convenient. 🎬 Space That Fits Your Life The finished lower-level recreation room is ready for your home office, gym, movie nights, or playroom. 🏡 Thoughtful Details Throughout • Beautiful 12" x 24" tile in all full bathrooms and the laundry room • Deako smart light switches and smart home features • Professionally designed landscaping • Energy-efficient construction and modern finishes 💰 Special financing programs and builder incentives available with the preferred lender. 🔑 Ready to make your move? Schedule a tour and see it for yourself! 📲 Contact Jimmy Thomas for current pricing, available homesites, and incentive details. 📸 Photos are representative and may show optional features.

Lot 5 Shuoner, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

205 Crestleigh Dr, Winchester
$630,000
4 Beds ⋅ 3 Baths
Extensively updated and thoughtfully maintained, this beautiful Colonial in the prestigious Oakdale Crossing community offers 3,058 square feet of living space, impressive outdoor amenities, and numerous improvements already completed. Recent updates include new siding and window trim in 2026, a new dishwasher in 2024, and a 2023 pool, tankless water heater, cooktop, refrigerator, and water softener. The roof was replaced in 2022, the HVAC system in 2018, and the front, back, and garage doors have also been replaced. Inside, you'll find four spacious bedrooms, 2.5 baths, rich wood flooring, crown molding, and an inviting layout designed for both everyday living and entertaining. The gourmet kitchen features granite countertops, a wall oven, cooktop, built-in microwave, and butler's pantry, with the dining area flowing naturally into the living space, where a cozy fireplace creates a welcoming focal point. The spacious primary suite offers a private retreat with an en-suite bath featuring a jetted tub. A wet bar and ceiling fans throughout add to the home's comfort and functionality. Looking for additional space? The 640-square-foot unfinished attic features subflooring and offers potential for future finishing, subject to applicable requirements. Create a home office, recreation room, additional living area, or keep it as valuable storage space. Set on a 0.35-acre corner lot, the outdoor living spaces are equally appealing. Enjoy the covered deck or relax beside the lighted, heated in-ground pool installed in 2023, complete with a hot tub for added enjoyment. An oversized side-entry garage and concrete driveway provide convenient parking and easy access. With extensive updates, generous living space, a versatile attic, and an inviting backyard retreat, this Oakdale Crossing Colonial offers a wonderful blend of comfort, functionality, and outdoor enjoyment. Check out the 3-D Tour attached to this listing!

205 Crestleigh Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Lots 10,11 & 12 Lots 10 11 & Rd, Winchester
$114,900
Two Building lots in an established community! Prime opportunity to build some spec homes or build for yourself and a friend or family member. Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have some space between neighbors. Lots 10, 11 & 12 are being sold collectively as two homesites. Only 8 miles to Winchester Medical Center and not on the side of a mountain, you'll love it here! Additional homesites available as well. Perfect opportunity for a builder looking to build in a growing community, or if you're looking to build bring your ideas!

Lots 10,11 & 12 Lots 10 11 & Rd, Winchester

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

Lots 14 & 15 Lots 14 & Rd, Winchester
$61,900
Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have some space between neighbors. Lots 14 & 15 are being sold collectively as one homesite totaling almost 3/4 of an acre. Only 8 miles to Winchester Medical Center and not on the side of a mountain, you'll love it here! Additional homesites available as well. Perfect opportunity for a builder looking to build in a growing community, or if you're looking to build bring your ideas!

Lots 14 & 15 Lots 14 & Rd, Winchester

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

Lots 4 & 5 & Rd, Winchester
$61,900
Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have some space between neighbors. Lots 4 & 5 are being sold collectively as one homesite totaling almost 3/4 of an acre. Only 8 miles to Winchester Medical Center and not on the side of a mountain, you'll love it here! Additional homesites available as well. Perfect opportunity for a builder looking to build in a growing community, or if you're looking to build bring your ideas! Road these lots sit on will be paved this summer.

Lots 4 & 5 & Rd, Winchester

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

611 Fawn Dr, Winchester
$289,900
2 Beds ⋅ 1 Baths
Welcome to this beautifully updated 2-bedroom, 1-bath cottage, perfectly tucked away on two picturesque, serene lots surrounded by mature trees. Offering the perfect blend of charm, privacy, and possibility, this inviting home has been thoughtfully rebuilt and improved over the years and is truly move-in ready. Step inside to find beautiful wood flooring, soaring ceilings in the bedrooms, an updated kitchen, and a cozy fireplace that adds warmth and character. Major improvements, including new siding and a new A/C unit, provide added comfort and peace of mind. Outside, the fully fenced yard creates your own private retreat with plenty of space for pets, gardening, entertaining, or simply enjoying the peaceful surroundings. Relax with your morning coffee on the porch, unwind beneath the trees, and take advantage of the expansive shed for additional storage, hobbies, or outdoor equipment. Situated on two lots with very limited restrictions, the property also offers exciting possibilities for future expansion. Whether you're looking for a peaceful full-time residence, weekend retreat, or a home with room to make your own, this charming cottage is a rare opportunity to enjoy privacy, tranquility, and flexibility all in one beautiful setting.

611 Fawn Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

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