291 properties for sale in Ole Orchard Estates

Upgraded home in a desirable 55+ community on Winchester's east side! Thoughtfully upgraded and beautifully maintained, this exceptional residence offers the perfect blend of comfort, convenience, and low-maintenance living. Inside, you'll find upgraded flooring, elevated finishes, and an open-concept layout designed for both everyday living and entertaining. The beautifully appointed kitchen flows seamlessly into the spacious family room, while the main-level primary suite features a private en suite bath and easy access along with two additional bedrooms on the main level. One of the few homes in the community offering both a composite deck and fully fenced backyard, this property provides a rare opportunity to enjoy privacy and outdoor living. The partially finished basement with half bath, adds flexible space for a rec room, home office, fitness area, or guest retreat, while still offering plenty of storage. As one of the first resale opportunities in this newer, highly sought-afte

Adorable Cape Cod in the heart of Winchester! Beautifully appointed with hardwood floors, signature arched doorways from that era adding tons of charm to this lovely home. Two main floor bedrooms, renovated and updated bath, living room with gas fireplace and brick surround, kitchen with brand new gas range, expanded space perfect for dining and entertaining with doors to the front and rear yards. Upper level is open for a bedroom or recreation room, tons of storage on either side of the room. Lower level with a workshop, built in corner cupboards, laundry, back room with shelving, separate lower level space with walkout to the front yard and driveway. The rear yard is HUGE! Fully fenced with two large storage sheds, covered back patio perfect for entertaining and all anchored by a gorgeous old Magnolia tree. New main roof in 2022, Roof on addition replaced in 2025, new water heater in 2025

Move-in ready 3-bedroom, 1 full bath, 1 half bath townhouse in a convenient Winchester location, offering easy access to commuter routes, just minutes from I-81 and Route 7. The interior is freshly painted with brand-new carpet and features an eat-in kitchen with stainless steel appliances that opens to a private patio, great for relaxing or entertaining. Conveniently located just minutes from shopping, dining, schools, and everyday conveniences

Charming All-Brick Rancher with inground pool and landscaped backyard. No hoa! This well maintained 3-bedroom, 1 full bath and two half baths home offers classic charm in one of Winchesters most desirable east-side locations. This home is move-in ready with freshly painted walls and new carpet in the basement. The roof was replaced in 2019. The main level showcases spacious living areas with a fireplace in living room flanked with built-ins adding warmth and character. Step onto the deck overlooking the backyard oasis including a small Koy pondcomplete with an inground pool perfect for summer fun. The pool liner will be replaced May/June 2026. The partially finished basement expands your living space with a large recreation room including a half bath and easy access to the poolideal for guests or gatherings. A one-car garage completes this inviting home. Dont miss the opportunity to own this home in an excellent location, just steps from Winchester Country Club and minutes to shopping,

2 Level Rambler Featuring Spacious Bedrooms and a Functional Layout Perfect for Comfortable Living. Enjoy Quiet Mornings or Evening Relaxation on the Inviting Covered Front Porch, and Take Advantage of the Rear Deck for Outdoor Dining and Entertaining. The Property Also Includes a Walk Out Basement and Storage Shed Providing Extra Space For Tools, Equipment, or Seasonal Items. Situated on a Desirable Lot, This Home Presents a Fantastic Opportunity for Buyers Seeking Value and Potential. With Some Cosmetic Updates and Renovations, This Property Can Truly Shine and be Transformed into a Beautiful Personalized Residence or Investment Opportunity. Sold As-Is

WellMaintained Ranch Home in a Peaceful, Convenient Winchester Location. This wellcaredfor ranch home offers an inviting blend of comfort, updates, and flexible living across both levels. Fresh paint and an upgraded kitchen set the tone, featuring stainless steel appliances, granite countertops, and plenty of workspace. A dedicated dining room and a spacious family room create an easy flow for everyday living. The main level includes a primary bedroom with its own ensuite bath, along with two additional bedrooms and a full hall bath. The lower level opens up even more possibilities with a large family/rec room anchored by a cozy fireplace, an exercise area, a separate room currently used as a bedroom, a full bathroom, and a laundry room with cabinetry. Whether you need guest space, hobby space, or a home office, the layout adapts to whatever you need next. Outside, the fully fenced, flat yard is a standout featureideal for pets, play, gardening, and all your summer activities. The new

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

Welcome to 237 Asbury Road in Winchester tucked away on a quiet cul-de-sac yet perfectly located just off Rt. 7 for an easy commute. This 4-bedroom, 2.5 bath home offers a spacious, functional layout with multiple living areas, including a living room, separate dining room, and a family room with fireplace. The custom kitchen features granite countertops, a center island with prep sink, ample cabinet space, a pantry for additional storage and a breakfast nook. The spacious primary suite includes a walk-in closet and a private bath with double vanities, a jetted tub, and a stand-up shower. In addition to the primary suite, there are three spacious bedrooms offering flexibility for family, guests, or home office space. Also, has a huge full unfinished basement that walks out to the wooded backyard and offers endless possibilities for storage, recreation space, or future expansion. Step outside to enjoy a private, tree-lined backyard that backs to woodsgiving you both space and privacy. T

Welcome home to 103 E Germain St, a rare end-of-row townhouse combining the historic elegance of downtown Winchester with the modern ease of late-80s construction. Whether you are a first-time buyer looking for a move-in ready home or a savvy investor looking for a high-demand rental with excellent yield potential, this property ticks every single box. Flooded with natural light, the main level features a desirable open floor plan that effortlessly flows from the inviting living room into a bright, combination kitchen and dining area. Beautiful hardwood floors anchor the main living level, complemented by a convenient half-bath. Step through the rear door to your Trex sun deck complete with cocktail railthe perfect spot for morning coffee or casual weekend entertaining. Upstairs, you will find two spacious, newly carpeted bedrooms with ample closet space and a full primary bathroom. Need extra storage? The home includes a massive unfinished attic and crawlspace basement to keep your li

110 SHUONER Ct Model Home | We Have spec homes Summer 2026 Delivery Available St. Paul tbb | 4 br | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger Deck Beautiful wooded homesites available! Offering up to 2,000 sq. Ft. of modern, open-concept living customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom. Home Highlights Open-concept main level perfect for entertaining Granite countertops Stainless steel appliances Luxury vinyl plank flooring Upper Level Retreat Deluxe Silver primary bath with rain shower Spacious walk-in closet Bedroom-level laundry Two additional bedrooms + full bath Finished Lower Level 4th bedroom Full bathroom Ideal for guests, home office, gym, or media room Additional Features Townhome landscaping package Deako smart light switches (smart home features) Larger composite deck Special financing programs available Builder incentives available with preferred lender Summer 2026 Delivery Available Contact listing ag

Fully renovated in 2021 and move-in ready! This charming home is conveniently located just off Route 7 Eastperfect for commuters! Enjoy peace of mind with major updates throughout, including brand-new windows, new HVAC, updated electrical system, and all-new appliances, including washer and dryer. The stunning, completely remodeled kitchen features granite countertops, stainless steel appliances, and brand-new cabinetry. Gleaming, refinished hardwood floors flow throughout the home, enhancing its warmth and character. Flexible living spaces include formal living and dining rooms, plus a main-level bedroom or office and a full bathideal for guests or remote work. Convenient main-floor laundry adds to the home's functionality. The basement offers excellent storage space, while outside you'll find a huge fenced yard with a shed and outbuilding perfect for hobbies, storage, or workshop potential. Don't miss this one!

Some homes check a few boxes. 440 Bristol Drive showed up with its own notebook and started making new boxes. Nestled on 13.8 gorgeous acres in Winchester, this stunning log cabin retreat offers just under 4,500 finished square feet, 5 bedrooms, and 3 full bathrooms. It feels less like a house and more like the place people imagine when they say, One day I'd love to own some land. Want to fish after work? There's a stocked pond with its own dock. Want to hike without driving anywhere? Step outside. Thinking about horseback riding, ATV adventures, gardening, watching wildlife, or simply sitting on a porch swing while pretending your phone doesn't exist? That's all here too. Inside, the home is every bit as impressive. The beautiful loft and elevated deck overlook the backyard and surrounding property, creating the kind of views that make coffee taste better and stress disappear faster. The soaring log cabin design delivers warmth, character, and enough charm to make you start shopping f

Brand-New Dual Primary TownhomeLate Summer Move-In! Step into modern living with this beautifully designed dual primary bedroom home, ideally located just steps from Snowden Bridges newest amenities. The entry-level bedroom with a full bath offers flexible space for guests, multigenerational living, or a private office. Upstairs, the light-filled open-concept layout features a stylish kitchen that flows seamlessly into the spacious family roomperfect for entertaining or everyday comfort. The top level showcases two spacious primary suites, each with a walk-in closet and private en suite bath, plus a conveniently located laundry area. Theres still time to personalize your finishes and make it your own! Enjoy resort-style living at Snowden Bridge with a pool, pirate-themed water park, indoor sportsplex, trails, dog park, and moreall just minutes from Winchester shopping and dining. Secure your new home now for a late summer move-in! Note. Photos are similar while home is under constructi

Fully Renovated 2026 | Turnkey 2BR/2BA Condo in Park Place Welcome to 136-8 Brookland Ctwhere style, comfort, and convenience come together. This stunning second-floor condo has been completely renovated in 2026, offering a like-new feel without the wait! Step inside to discover all-new flooring, appliances, lighting, fixtures, vanities, doors, and countertopsevery detail thoughtfully updated for modern living. The bright, open floorplan is perfect for both everyday life and entertaining, featuring a cozy electric fireplace that adds warmth and charm. The spacious primary suite boasts a walk-in closet and private en-suite bath, while the second bedroom offers flexibility for guests, a home office, or more. Enjoy the ease of one-level living with in-unit laundry and step out onto your private balconyperfect for morning coffee or unwinding at the end of the day. Located in the sought-after Park Place community, youll love the peaceful setting with plenty of parking, all just minutes from

Move-In Ready! No hoa! Updated Split Foyer with Fresh Paint from Top to Bottom, All New Carpet, Granite Counters & Stainless Steel Appliances In Kitchen, Gleaming Hardwoods & New LVP on the Main Level, 3 BR & 2 BA Upstairs, 4th BR + Large Rec Room & Laundry Room in Basement, Deck off the Main Level overlooks treed back yard. Covered Front Porch, Oversized 2 Car Garage + Ample Driveway Parking & Storage Shed on a Spacious 1/3ac Lot Backing to Trees. More Details Coming Soon!

Remarkable and new to the market Anderson subdivision lots. Located 5 minutes from downtown Winchester and Valley Health Medical Center (2 minutes from James Wood High School) off Apple Pie Ridge. Entrance Road Under Construction, currently. These lots feature panoramic views of the entire Shenandoah Valley from Harper's Ferry to Strasburg to the Western Mountains, providing stunning views from an elevated, very private environment. These 5 acre lots are available through Merrifield Homes, whereby homeowners can utilize plans offered by builder, or bring their own. 14 remaining lots with construction available starting in 2026. Lots have VDH-approved septic design, mainly CONVENTIONAL septic systems. Cable TV and power already on-site. Buyers can choose cabinets, finishes, appliances, countertops, interior and exterior colors, etc. Full customization available, or buyer can choose from standard finishes. Separate, free-standing garage option available. 3-car option available. These wil

Welcome to 5242 Mulberry Run Ctan inviting and well-maintained townhome in the heart of Stephens City offering space, comfort, and everyday convenience. This 3-bedroom, 2.5-bath home features nearly 1,900 square feet of living space with a functional layout designed for modern living. Step inside to find a bright and open main level perfect for both relaxing and entertaining. The spacious living area flows seamlessly into the dining space and kitchen, creating an easy, connected feel. Upstairs, youll find generously sized bedrooms, including a comfortable primary suite with its own private bath. Additional highlights include a 1-car direct-access garage, off-street parking, and low-maintenance exterior construction. Built in 2007, this home offers the reliability of newer construction within an established community. Located in the desirable Mulberry Terrace subdivision, youll enjoy quick access to shopping, dining, commuter routes, and nearby Winchestermaking this an ideal location fo

Up to $10,000 closing cost assistance for primary residence with use of approved lender and title! *. Discover exceptional value in the newest phase of Boyds Crossing! Ideally located in South Berkeley, this community offers the closest new construction townhomes to the Virginia state lineperfect for commuters seeking easy access to Interstate 81 and nearby Northern Virginia. Enjoy some of the largest townhome homesites in the area, designed with both comfort and convenience in mind. Plus, low-maintenance living comes standard, with the HOA covering front yard landscaping and trash service. Dont miss your opportunity to be among the first to call this exciting new phase home! Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing

Wow recently remodeled home that checks all the boxes. Main level features beautiful kitchen with quartz countertops and stainless steel appliances. New flooring and paint throughout home. 3 Beds and 2 baths on this level with a large living room and kitchen. Large back deck off the kitchen with stairs that go down into your fenced in backyard. The corner lot allows for a larger backyard that can also be extended for more room. Downstairs you will find a fully finished basement for even more space. Also major systems like hvac, water heater and roof are less then 5 years old

Price improvement. Motivated sellers. Bring offers! Fully Renovated SFH in Historic Winchester! Prime location. Just minutes from charming Historic Downtown Winchester featuring local shops, restaurants, entertainment, and more! Beautifully Updated throughout. This charming home offers bright, inviting living spaces with modern finishes and thoughtfully updates designed for comfortable everyday living. W Just Move Right In! Major improvements include: New roof New siding New flooring Fresh drywall New appliances New A/C mini splits Updated systems throughout Practically everything has been replaced! Rare Upper-Level Layout 3 bedrooms upstairs Full bath on upper level Convenient half bath on main level Outdoor Features You'll Love Relaxing front porch perfect for your morning coffee or evening beverage Fenced yard for pets, play, or entertaining Plenty of street parking nearby Perfect Opportunity For: First-time home buyers Students Investors seeking a turnkey property low maintenance p

Welcome to 113 Gretchen Court, a beautifully maintained 3-bedroom, 3.5-bath home tucked away on a quiet cul-de-sac in the heart of Stephenson, Virginia. Offering a perfect balance of comfort and functionality, this home is ideal for both everyday living and effortless entertaining. Step inside to a warm and inviting main level, where natural light fills the spacious living areas. The cozy gas fireplace creates the perfect focal point for relaxing evenings, while the open flow makes hosting family and friends a breeze. The kitchen provides ample cabinetry and workspace, seamlessly connecting to the dining and living areas with hardwood flooring throughout the living and dining rooms and stainless appliances in this beautiful sun kissed kitchen. Upstairs, youll find three generously sized bedrooms, including a comfortable primary suite designed for rest and privacy. Hardwood flooring throughout the upper level. Laundry room is on the bedroom level for convenience and comfort. The fully f

Located just minutes from Winchester, I-81 and Route 7. Perfect for investors looking for a great rental or an easy handyman update and flip opportunity. This home is 1,288 sq ft on a full 1.3 acre lot. Featuring 3 bedrooms and 2 bathrooms, the property provides solid space and privacy with a country setting. Home is move in ready but in tired and outdated condition. With the light improvements, there is strong upside potential. ALSO INCLUDED is a second, adjoining parcel, which is just under half an acre, for a combined total of 1.7 acres

This charming home, a short walk from historic Winchester, underwent a complete studs up renovation a few years ago. With all new insulation, roof, energy efficient double pane windows, and updated systems, it offers efficiency and ease. The open floor plan flows into a kitchen with a dedicated pantry closet. Three appropriately sized bedrooms include a master with its own bath. Plus, enjoy upgraded padded laminate flooring, a fenced backyard, and low maintenance vinyl siding-ready to move in and enjoy!

Easy living starts hereand time is running out to move in this year. Construct this thoughtfully designed mainlevel living home and have the opportunity to personalize your style with your choice of flooring, cabinets, countertops, and fixtures. The main level features lowmaintenance LVP flooring throughout, vaulted ceilings in the family room, and a spacious primary suite with a deluxe bath showcasing a frameless shower and relaxing soaking tub. Two additional bedrooms and a conveniently located laundry room keep daily living effortless. The kitchen is already equipped with gourmet stainless steel appliances with a statement hood, and a farmhouse sinkjust waiting for your selected quartz counters and cabinet colors to complete the look. Oak stairs lead to the finished lower level, offering even more living space with a recreation room, fourth bedroom, and full bath. A rear screened porch provides the perfect spot to unwind. Located in the premier Snowden Bridge community, enjoy resort

Claim your spot in the heart of the city with this authentic 1866 gem, perfectly positioned to enjoy everything downtown Winchester has to offer. Proudly displaying its Winchester Historic Building plaque, this home is just steps from the vibrant local dining scene, boutique shopping, parks, and schools. Its a rare find that pairs 19th-century soul with modern reliability, featuring the coveted convenience of off-street parking in the rear, a one-year-old roof and a dual-zone climate system with two AC units and two Lennox furnaces. The main level is full of original character, anchored by beautiful hardwood floors. The kitchen serves as a functional and warm centerpiece, featuring granite counters, stainless appliances, and a stunning wall of original exposed log beams. Just off the kitchen, the formal dining room retains its classic charm with a decorative fireplace and original period details, while the rest of the floor opens into a large, versatile living room framed by custom bui