227 houses for sale in Ole Orchard Estates

Fresh, move-in ready, and conveniently located! This well-maintained townhome has been freshly painted throughout and offers an easy-flowing floor plan designed for comfortable everyday living. Step inside to a bright, open main level where the living room, dining area, and kitchen flow seamlessly togetherperfect for entertaining or simply relaxing at home. The kitchen offers the added convenience of a walk-in pantry, while a half bath and access to the one-car garage complete the main level. Upstairs, youll find a spacious primary bedroom suite featuring a vaulted ceiling, along with two additional bedrooms and another full bath. LVP flooring throughout provides a clean, cohesive look and easy maintenance. Outside, enjoy your own fenced rear yard and patio, offering privacy and a great space for relaxing, grilling, pets, or outdoor entertaining. Located in an easy-access commuter location just minutes from I-81, offering commuter conveniencethis one is ready to welcome you HOME!

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

To Be Built home in the Cressen Run community. This exquisite new construction residence is poised to redefine country living. Set on a sprawling 33.16-acre lot, the property offers a breathtaking panorama of majestic mountains and serene woodlands, creating an idyllic retreat that feels worlds away from the everyday hustle. This stunning farmhouse-style home, designed with meticulous attention to detail, features four spacious bedrooms and two and a half nicely appointed bathrooms. The heart of the home boasts a workable kitchen equipped with stainless steel appliances, including a built-in microwave, electric oven/range, and a sleek refrigerator, perfect for culinary enthusiasts. The inviting living area, complete with a cozy gas fireplace, sets the stage for intimate gatherings or tranquil evenings. The ability to select your color selections for construction presents a unique opportunity for personalization, allowing you to tailor the space to your discerning tastes. Imagine crafti

Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas. The updated kitchen features new cabinetry and stainless steel appliances, creating a clean, contemporary space perfect for everyday living and entertaining. Both bathrooms have also been thoughtfully updated, adding to the homes fresh and modern appeal. Enjoy your morning coffee or unwind at the end of the day on the covered front porch. The partially fenced yard provides space to enjoy the outdoors, while the storage shed offers convenient additional space for tools, lawn equipment, and seasonal items. Convenient rear-entry parking provides easy access to the home, with additional street parking available in front. The unfinished basement provides valuable a

Welcome to a MidCentury Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 34 bedroom midcentury modern home, where timeless character meets modern sophistication in one of Winchesters most convenient and walkable locations. The large covered front porch immediately sets the tonean inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The wellproportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling yearround, a new ductless minisplit system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainlesssteel appliances, and a pantry with builtin cabinetry, provid

Welcome to 769 Seldon Drivean elegant brick-front colonial situated on nearly half an acre in one of Winchesters most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. Create wealth with this income producing opportunity. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along with formal living and dining rooms, a warm and inviting family room with fireplace, and a well-equipped kitchen with center island and breakfast area. Hardwood floors and detailed trim work add classic character throughout. A standout feature of this home is the private ground-level apartment with its own entrancecomplete with a full kitchen, bedroom, bathroom, living space, and dedicated laundry. Perfect for guests, extended family, or potential rental income. Upstairs, you'll find additional spacious bedrooms and full baths, offering plenty

Affordable Winchester Townhome with Investment Potential! Welcome to 107 Little River Dr, a conveniently located 2-bedroom, 1-bath townhome offering an excellent opportunity for a first-time buyer, downsizer, or investor. This two-level home provides approximately 900+ square feet of living space with a practical layout and plenty of potential to make it your own. Located in the Brookland Heights community, the property offers easy access to Winchester-area shopping, dining, employment centers, and major commuter routes. The low-maintenance townhome lifestyle makes this an attractive option for buyers looking for affordability and convenience. Whether you're searching for a primary residence, rental property, or value-add investment, 107 Little River Dr is worth a look. Bring your vision and unlock the potential of this Winchester opportunity!

New End Unit Under Construction for Fall Move In! Main-level living at its best in Hiatt Pointe at Snowden Bridgea gated 55+ active adult community. This low-maintenance villa features a primary bedroom and laundry on the entry level, a screened rear porch, and a one-car garage. Upstairs offers two spacious bedrooms with walk-in closets and a full bath, plus a finished storage area! Enjoy a stylish kitchen with quartz counters and stainless steel appliances. Resort-style amenities include pickleball and bocce courts, clubhouse, fitness and yoga studios, outdoor kitchen, pool and hot tubplus snow removal, trash, and recycling included. Ask about builder incentives today!

Under construction for fall move in! Discover relaxed, lowmaintenance living in this beautifully crafted twin/semidetached home, coming this summer to a soughtafter gated activeadult community. Designed with todays vibrant 55+ lifestyle in mind, the home offers effortless mainlevel living with both a primary and secondary bedroom conveniently located on the first floor, along with a versatile denideal for a home office, creative space, or quiet retreat. The openconcept design brings the kitchen and family room together, creating a warm, welcoming space perfect for hosting friends or simply enjoying everyday living. The gourmet kitchen features a generous island, stainless steel appliances, colada cabinetry, and elegant quartz countertopsblending style with functionality. Sunfilled rooms and modern finishes throughout add to the homes airy, inviting feel. Upstairs, a private third bedroom and full bath provide the perfect accommodations for visiting guests or additional flexible living

Main level living in an idyllic setting. Welcome to Stonymeade! 2 acre Home Site in Winchester Virginia Base price shown is for the Boxwood MAIN LEVEL Owners Suite FLOORPLAN and we have many other plans including those with first floor primary suites, farmhouse kitchens, and multi-generational options. All homes include exceptional standard features including 10' main level ceilings, Hardwood floors, upgraded cabinetry and countertops, extensive trim package, and HardiePlank exterior. Plans are ready to be customized! DECORATED MODEL HOME located at 156 Covey Lane Winchester Va Open SATURDAYS and SUNDAYS from 11am to 5pm Call Sales Manager for Appointment

Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath. The properties are deeded separately as two parcels (tax #193-01-T-9 & 193-01-T-8), providing added flexibility for future investment strategies. All occupied units are currently rented on month-to-month leases, offering the new owner maximum flexibility to adjust rents, renovate, or continue operating as investment properties. As of the listing date, one unit is vacant, presenting an immediate opportunity to place a new tenant at market rent or occupy the property. Prospective buyers are welcome to drive by and walk the exterior of the properties. Interior showings are by appointment only. Whether you're looking to expand your rental

Wow! *. New price + exceptional value in winchester! Move-In Ready No HOA Fantastic Location Across from Winchester Country Club! Tucked away on a quiet cul-de-sac in the desirable Rolling Fields community, this beautifully updated Split Foyer offers a spacious. 38-Acre Lot, peaceful tree-lined backyard & an EXTRA-DEEP OVERSIZED 2-CAR GARAGE! Freshly Painted throughout with Brand-New Carpet, Gleaming Hardwood Floors & updated Luxury Vinyl Plank Flooring, this home is truly Move-In Ready | The bright & inviting Main Level features a spacious Living Room, Formal Dining Room & Eat-In Kitchen with Granite Countertops & Stainless Steel Appliances | 3 Main-Level Bedrooms & 2 Full Baths include a comfortable Primary Suite with Private Bath | The Finished Lower Level provides even more flexible living space with a Large Recreation Room, 4th Bedroom, Laundry Area & direct access to the Oversized Garageoffering exceptional room for Vehicles, Storage, Hobbies or a Workshop | Relax on the Covered

Welcome to 114 Settlers Circle, a spacious 5-bedroom, 3.5-bathroom home nestled on a quiet street in a prime east-side Winchester location. Classic curb appeal greets you with a timeless brick front, framed by gorgeous mature trees that offer natural shade, privacy, and lush beauty. Step inside to an elegant two-story foyer flanked by formal living and dining rooms, setting the stage for easy entertaining. The main level shines with gleaming hardwood floors throughout most of the living areas and flows effortlessly into a sun-filled kitchen. Outfitted with a convenient breakfast bar and pantry, the kitchen centers around a bright eat-in nook surrounded by wall-to-wall windows, seamlessly opening to a family room complete with a cozy gas fireplace. A convenient half bath rounds out the main floor. Upstairs, you will find a spacious primary suite featuring a large walk-in closet and a beautifully appointed attached bath with dual/split vanities and a relaxing corner soaking tub. The uppe

If you've been waiting for a home that offers both character and modern convenience, this one deserves a close look. This all-brick, charming Cape Cod is located on a beautiful tree-lined street in the heart of Winchester with more space & versatility than meets the eye. Cross the threshold into the large, welcoming foyer and let your gaze take it all in. Large living room, large dining room, gorgeous staircase and center hall that draws you toward the beautifull, newly installed gourmet kitchen with butlers pantry. With 3 finished levels this home delivers space, comfort, and an unbeatable location in highly desired Downtown Winchester. Thoughtfully maintained and recently refreshed, this home features 4 bedrooms, 2 full baths, and a half bath, beautiful refinished wood floors and a newly remodeled kitchen that is sure to impress. Completed in September 2026, the kitchen dazzles with ample gorgeous cabinetry, extra-depth quartz counter tops, stunning center island with modern pendant

Classic all-brick home in a highly desirable Winchester location! Well maintained and thoughtfully designed, this five bedroom, three full bath home offers timeless character, spacious living areas and exceptional convenience. The main level features a gracious living room with fireplace, cozy den with fireplace and bookshelves and a primary bedroom on the main level. Four additional bedrooms provide excellent flexibility for family or guests. The finished basement offers valuable living and recreational space. Outside, enjoy the beautifully landscaped level lot and inviting brick patio. Two car garage. Ideally situated within walking distance to Handley High School and downtown Winchester

Welcome to this beautifully refreshed two-story home in the desirable Chandlers Glen community! This home offers comfortable living spaces with thoughtful updates throughout. New carpet and fresh paint throughout give the interior a clean, bright, move-in-ready feel. The main level offers a functional layout with a spacious living area, and well-appointed kitchen, along with convenient access to the attached garage. Upstairs, you'll find comfortable bedrooms and additional living space, including a generously sized primary suite. The unfinished basement provides excellent potential for future expansion, whether you envision a recreation room, home office, gym, or additional living space. A rough-in for a bathroom is already in place, offering even more possibilities for the next owner. Outside, enjoy a manageable quarter-acre lot with a paved driveway, attached garage, and plenty of yard space. Located in Bunker Hill with convenient access to Winchester, Martinsburg, major commuter rou

450,000 4 bedrooms, 2 Full baths, (Price is negotiable! )2,493 square feet living space with a full basement 501 Fox drive is strategically located 1.5 miles from the Valley Health Hospital, 1.4 miles from James Wood High School and one mile from the highway at Route 37. Talk about great location! This four bedroom family home is on a perfect corner lot for added space. Recently renovated with Fresh paint throughout, New laminate flooring, New blinds, Updated bathroom that includes a new sink/cabinet and a new toilet, The bedrooms include new carpeting and new ceiling fans. The new renovations also include a brand new dishwasher and dryer. To add on to the list this property add's new backyard fencing and new all weather 10 X 12 storage unit. Dream house for the first time buyer, Dont miss this opportunity!

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the res

Welcome to beautiful Chandlers Glen, where outdoor living takes center stage. Situated on a spacious 0.38-acre lot that backs directly to the woods, this property offers the privacy and peaceful setting homeowners are looking for. The backyard is truly a standout feature, highlighted by a brand-new vinyl privacy fence that completely encloses the rear yard, creating a secure and secluded space for relaxing, entertaining, pets, or outdoor activities. With wooded views beyond the fence, you'll enjoy an added sense of privacy and a natural backdrop rarely found in neighborhood living. Adding even more value is the impressive 12' x 20' storage shed, providing exceptional space for lawn equipment, tools, seasonal dcor, recreational gear, or workshop use. Whether you need extra storage or a dedicated hobby space, this oversized shed offers endless possibilities. The outdoor amenities continue with a charming gazebo, creating the perfect gathering spot for morning coffee, weekend cookouts, or

Your Next Chapter Starts Here! Space, style, flexibility, and a backyard made for entertaining all tucked away on a quiet cul-de-sac in desirable Oakdale Crossing. This impressive 5-bedroom, 4-bathroom, three-level Colonial, with new roof (2026), delivers the kind of versatile space todays buyers are looking for, with room to work from home, host friends, grow your household, or create the ultimate hangout zone. Start with the front wraparound porch, the perfect spot for morning coffee or winding down at the end of the day. Out back, the fun really begins: multiple composite decks with a pergola overlook a private, fully fenced yard backed by mature trees, creating your own outdoor retreat. The 20' x 30' saltwater above-ground pool takes summer entertaining to the next level. Inside, beautiful hardwood floors run throughout the main and upper levels. The main level offers an easy-flowing layout with a welcoming family room featuring a gas fireplace, separate dining and living rooms, pl

NEW BUILD, move in ready single-family home at Hiatt Pointe, 55+ community at Snowden Bridge by Van Metre Homes! The Sierra 39-F2 at Hiatt Pointe is stunning! This home offers 3 bedrooms, 3 full bathrooms, a 2-car front load garage, a finished basement and much more! As you enter the home you are greeted with 9' ceilings, luxury vinyl plank flooring, recessed lighting throughout, programmable thermostat, tankless gas water heater, solar panel ready, open floor plan, huge rec room on the lower level, all spanning over 3200 sq ft. The kitchen is a chef's dream with all stainless-steel appliances, white quartz counters, a spacious island and a walk-in pantry with solid shelving. Off the great room is your 20x12 deck, making it easy to entertain your family and friends! Cozy up by your electric fireplace to unwind or enjoy a good book. The primary suite offers a large bath with quartz counters, dual vanities, soaking tub and a roll. In frameless tile shower. On the lower level of the home,

Offering three luxuriously finished levels, extensive upgrades, and a backyard designed for entertaining, this 4 bed/3.5 bath colonial is a MUST-SEE! Step inside to a grand foyer with soaring 12-foot ceilings and walls of windows flooding the home with natural light throughout. The main level features a dedicated study room accented by striking arched windows, spacious living and dining areas, an open kitchen with a window overlooking the serene backyard, and a showstopping family room wrapped in eight oversized windows with transoms that frame views of the outdoors and create a bright, airy gathering space centered around a cozy fireplace. Step outside to your own backyard retreatan entertainers dream with an expansive, fully fenced lawn, large low-maintenance composite deck, spacious brick patio, and custom-built outdoor brick fireplace. Imagine summer cookouts on the deck, evenings around the fire, or simply enjoying the abundance of your own private open space. Upstairs, the expans

This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the updates today's buyers are looking for. Homes in this sought-after neighborhood rarely come to market, making this a special opportunity in one of the area's most convenient commuter locations. Inside, you'll find a comfortable blend of hardwood, tile, and carpet flooring, built-in shelving, fresh paint in many areas, and charming details including chair rail and crown molding in select rooms. The living area features an antique stained-glass mantle that has been beautifully refinished and incorporated above the gas fireplace, creating a distinctive focal point. Upstairs, four large bedrooms provide plenty of comfortable living space, including a spacious primary bedroom with its own private bathroom. A finished and conditioned third-floor loft adds a huge, flexible bonus space ready to meet your needs; perfect for a 5th bed

Welcome home to 100 Winns Circle, perfectly situated on a generous 0.4-acre corner lot in Pioneer Heights. Located less than 5 minutes from Route 7 east of Winchester, this beautifully updated property offers the rare combination of neighborhood living without close neighbors or crowded structures. Step inside to find a freshly painted interior bathed in natural light, thanks to oversized Andersen windows and new LED lighting throughout. The main level features gleaming hardwood floors in the formal dining room and a massive living room centered around a magnificent floor-to-ceiling stone wood-burning fireplace. From here, premium patio swing doors open to a large rear deckideal for entertaining or relaxing. The kitchen is a chef's delight, outfitted with pristine oak cabinets, Corian countertops, brand-new LVP flooring, and new appliances, including a side-by-side refrigerator and slim-profile microwave. Upstairs, the layout is designed for modern living. The spacious primary suite ac

Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This single-level home offers a practical layout with comfortable living spaces and plenty of potential to make it your own. The main-level living design provides easy access throughout the home, making this property a great fit for first-time buyers, downsizers, or anyone looking for a manageable home without stairs. The level lot offers space for outdoor enjoyment, gardening, entertaining, or future improvements. With three bedrooms, a full bath, and a manageable footprint, this home offers an excellent opportunity for a buyer looking for affordability and convenience. Bring your vision and add your personal touches to create the home you've been looking for

Discover a rare opportunity to own a piece of Frederick County history with this unique farmette property offering approximately 9.79 acres, a charming farmhouse, extensive outbuildings, and an established farm market setup. Originally built in the 1800s with later additions, the home offers character that is difficult to replicate while providing the space and functionality today's buyers appreciate. Beyond the residence, this property truly shines through its improvements, including a large approximately 2,400-square-foot wooden barn with three stalls, multiple storage buildings, workshop space, greenhouse/storage building, orchard and garden area, and a separate farm market building. The farm market features separate electric service, insulation, gas heaters, refrigerators, counters, shelving, and a layout that has supported farm market operations. (Buyer to verify all intended uses with Frederick County) Whether your vision includes homesteading, raising animals, growing produce, o

Unique 5+ acre property in Winchester. Beautiful home with plenty of space for everyone's interests. 5 bedrooms. All with en suite bathrooms. High end kitchen designed by a chef. Plenty of outdoor entertaining areas. 2400 sq ft garage/workshop, green house, extensive gardens including koi pond. Abrams Creek runs along the back of property. Wildlife including Bald eagles, Blue heron, and deer frequent the property. All this within minute to Winchester

Move-in ready and well maintained! This charming 2-bedroom, 1.5-bath townhome offers comfortable living with a spacious main-level living area, eat-in kitchen, and convenient laundry. The partially finished basement adds a large family room and plenty of storage, with walk-out access to a shaded patio and large, private fenced backyard. Relax on the back deck surrounded by mature trees, offering a peaceful and private outdoor setting. Conveniently located near shopping and Routes 81 & 7. Updates include: HVAC (2022), hot water heater and pressure tank (2024), roof (2008), all-new blinds, and a freshly painted and refreshed deck

Nestled in the charming Copperfield neighborhood, this delightful townhouse offers a perfect blend of comfort and convenience. Built in 2002, this well-maintained home features 2 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and everyday living. With 1,868 square feet of thoughtfully designed interiors, you'll find a cozy atmosphere that invites you to unwind. The inviting layout includes a versatile basement, perfect for a home office, gym, or additional storage. The exterior boasts classic vinyl siding, enhancing the home's curb appeal while ensuring durability. Enjoy the ease of parking with two dedicated spaces in the nearby lot, making coming home a breeze. Copperfield is more than just a location; it's a vibrant community. Residents appreciate the nearby trails and parks, perfect for leisurely strolls or weekend picnics. Local shops and dining options are just a short drive away, offering a variety of choices to satisfy every palate. The neighborhood i

This is the one you have been waiting for! Well cared for home, one story living in desirable Briarwood Estates. East side location convenient to commuter routes, shopping and Old Towne Winchester. Open floor plan with close to 1700 square feet. Three bedrooms, two full baths with hardwood floors in living/family room and dining area. Gas fireplace in family room, two walk in closets in master suite. Two car garage, two decks (enjoy your morning coffee on deck off of master bedroom! )and large fenced backyard with storage shed