209 houses for sale in Ole Orchard Estates

1019 Berryville Ave, Winchester, VA 22601 | Income-Producing Multi-Family Triplex Prime Winchester location! This approximately 3,000+ square foot finished triplex offers flexible, multi-level living with three full, independent residential/commercial units, each featuring a private entrance, full kitchen, and separate electric. Zoned for multi-family use, the property provides an excellent opportunity for investors, owner-occupants, or buyers seeking multiple income streams and versatile space. The property currently offers two leased units, providing established rental income, while the third unit is currently being utilized as an Airbnb, creating additional income-producing potential. A rear parking lot provides convenient off-street parking for tenants, guests, and occupants. Located on Berryville Avenue with convenient access to Downtown Winchester, Old Town Winchester, shopping, dining, entertainment, schools, medical facilities, and major commuter routes. The property offers eas

Location Location Location, Nice home tucked away in a cul-de-sac, this ranch style home offers 4 bedrooms and 2 full bathrooms. Eat in kitchen that has room for a table and chairs. This home has an addition built on that offers a large family room and the fourth bedroom. The floors have not been finished in the addition and is waiting for your touches. There is a deck off of the kitchen waiting for your backyard entertainment or just to relax on in the mornings with your cup of coffee. Just minutes from Rt 7 for easy commuting. Make an appointment to see what this home offers

Charming cape cod in an ideal intown location, this home has a welcoming ease to it, offering 34 bedrooms and 2.5 bathrooms with a layout that adapts beautifully to everyday living. The main level includes two convenient bedrooms, a comfortable, lightfilled living room, a separate dining area, and a renovated kitchen featuring new cabinets and stainlesssteel appliances. In 2021, the home received a thoughtful refresh: new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, new receptacles/switches/covers, a new roof, and more paired with updated plumbing for added peace of mind. Upstairs, youll find two additional rooms and a bathroom, including a potential fourth bedroom or bonus room ideal for an office or extra space. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and a door leading directly to the backyard, offering room to expand, unwind, or create a second living area. Outside you will find a spaci

Discover a new MOVE-IN READY and thoughtfully designed home for active 55+ living. This BRAND NEW END VILLA gives you more time to enjoy what matters most. Main-level living and a low-maintenance design means less time on upkeep and more time enjoying Hiatt Pointe's RESORT-STYLE AMENITIES and active social calendar events. From pickleball and the pool to water aerobics, Mahjong nights, and Friday happy hours, every day offers a new opportunity to stay active, connected, and engagedall within a gated community. Explore Homesite 1090, the final move-in ready end villa home at Hiatt Pointe (55+). Offering a two-car front-load finished garage, with three bedrooms, two full bathrooms, and one half bathroom. With 9 ft. ceilings on both levels, Luxury Vinyl Plank (LVP) flooring, oak main stairs, and expertly selected finishes, this villa feels effortlessly unique. The kitchen, central to the entire home, is complete with white soft-close cabinetry, white quartz countertops, a large island, Sa

Price adjustment. Welcome to this beautifully remodeled end-unit townhouse offering three spacious levels of comfortable living. The main level features a refreshed kitchen with brand-new cabinets, new flooring, and recessed lighting, creating a bright and inviting space for everyday living and entertaining. Upstairs, youll find two generously sized rooms, each with its own full bathroom, providing comfort and privacy. The fully finished walk-out basement offers a bedroom, full bathroom, laundry area, and direct access to the outdoors. A versatile bonus room provides additional space that can be used as a home office, storage area, or flex space to suit your needs. With its desirable end-unit location, spacious layout, multiple bedrooms and bathrooms, and recent updates, this townhouse offers a wonderful combination of style, functionality, and convenience. Professional pictures coming soon! Schedule your showing today, this will not last!

Charming 2-bedroom, 1-bath bungalow just blocks from the heart of downtown Winchester! This beautifully maintained home offers the character and convenience you're looking for, with gorgeous hardwood floors, a spacious fenced yard, and inviting covered front and side porches. The bright, comfortable interior offers a functional layout with two bedrooms and one full bath, while the full unfinished basement provides excellent storage and potential for future use. An updated roof adds peace of mind. Outside, enjoy the surprisingly spacious lot, with plenty of room for gardening, pets, entertaining, or simply relaxing outdoors. The backyard includes a shed for additional storage, while off-street parking adds everyday convenience. Located just a few blocks from Winchester's vibrant walking mall, you'll be close to local restaurants, coffee shops, boutiques, parks, entertainment, and community events. A wonderful opportunity to enjoy the charm of an established downtown neighborhood with th

Rare cul-de-sac opportunity in sought-after Snowden Bridge! This stunning 5-bedroom Sinclair is under construction for a year-end move-in and offers the perfect blend of space, style, and location. Unwind on the screened porch overlooking your backyard retreat, while luxury vinyl plank flooring flows throughout the main level. The gourmet kitchen shines with stainless steel appliances, a designer hood, quartz countertops, farmhouse sink, and abundant gathering space. A flexible front room is ideal for a home office, while the mudroom keeps everyday living organized. Upstairs, the luxurious primary suite features a spa-inspired bath with a freestanding soaking tub, frameless glass shower, and quartz vanities. Three additional bedrooms, two full baths, and a convenient laundry room with sink complete the second floor. The finished lower level adds even more living space with a recreation room, fifth bedroom, and full bath. Located just minutes from shopping, dining, and entertainment in

Welcome home to 103 Trade Wind Lane, a beautifully updated townhome offering low-maintenance living on Winchesters desirable east side! Perfectly situated near top schools, shopping, dining, and major commuter routes, this turn-key residence delivers both comfort and ultimate convenience. Natural light pours into the bright living room, where modern flooring lead you straight into the open kitchen and dining area designed for easy everyday living. Outfitted with brand-new granite countertops, a center island, plentiful cabinetry, and a new dishwasher, this space effortlessly opens to the rear deck for peaceful outdoor relaxation. Rounding out the main level are a conveniently located half bath and main-level laundry setup. Upstairs, retreat to the primary suite featuring a spacious layout, a walk-in closet, and a private ensuite bath. Two additional well-proportioned bedrooms share a second full bath, perfect for family, guests, or a flexible work space. The upper level shines with bra

Historic Farmhouse Charm with Exceptional Farm Potential Welcome to this remarkable farmhouse-style residence, originally built in 1790 and beautifully situated on 2.46 acres. Offering a wonderful blend of historic character, modern comfort, and exceptional outdoor amenities, this property is the perfect opportunity for those looking for a versatile family homestead with room for animals, gardening, hobbies, and outdoor enjoymentall conveniently located just 2 miles from I-81. Classic vinyl siding and extensive hardscaping welcome you to the home and create inviting spaces for relaxing and entertaining. Inside, the home's historic charm is complemented by thoughtful updates and modern conveniences. Exposed beams add warmth and character throughout the spacious living areas. The heart of the home is the gourmet kitchen, featuring ample cabinetry, a pantry, and a spacious breakfast area. The kitchen and dining area flow effortlessly into the family room, where exposed beams and a wood-bu

Priced at recent appraised value. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level washer/dryer. The second level of the home offers a sitting area, primary bedroom with its own half bath and two addtional bedrooms with a shared bathroom. Accessed by the third bedroom, the attic offers a blank canvas and could be easily transformed into a secondary living area, home office, or a recreation and fitness room. Wide plank pine flooring remains throughout most of the home along with many traditional fiixtures. Recent improvements include a new gourmet kitchen with SS appliances, hvac, water heater, exterior clapboard cedar siding replaced where nee

Great Commuter Location in Brookland Manor! 3 level townhome features 3 bedrooms, 2 full baths, 2 half baths, one car garage, master suite with full bath (shower and soaking tub) and walk-in closet, family room on lower level, large living room and kitchen on main level. 50-year shingles installed in 2022, new air handler in 2025. Seller is listing both for sale or lease

Beautifully maintained by its original owner, this all-brick Colonial in the desirable Windsor Hill community reflects years of thoughtful care and pride of ownership. Set on a beautifully landscaped 0.3-acre lot, the home offers more than 3,300 finished square feet, 4 bedrooms, 3.5 baths, and a side-load garage. All just minutes from downtown Winchester. Inside, the warm and inviting floor plan features hardwood floors, crown molding, built-ins, and spacious formal living and dining rooms. The gorgeous renovated kitchen offers upgraded countertops, abundant cabinetry, and a sunny breakfast area that opens to the family room with a gas fireplace. An ideal layout for everyday living and entertaining. Upstairs, the spacious primary suite includes a private bath with a jetted tub and separate walk-in shower, while the additional bedrooms offer plenty of space. Outside, mature landscaping, extensive hardscaping create a beautifully established setting with wonderful curb appeal. Meticulous

Move-In Ready Villa in Hiatt Pointe at Snowden Bridge's Premier Gated 55+ Community! Experience the ease of low-maintenance living in this beautifully designed home, ready for immediate move-in. Enjoy the convenience of a main-level primary suite and laundry, plus a screened rear porch perfect for relaxing with morning coffee or entertaining friends. The stylish kitchen showcases quartz countertops, stainless steel appliances, and striking two-toned white and admiral cabinetry. Upstairs, you'll find two spacious bedrooms with walk-in closets, a full bath, and a flexible study ideal for hobbies or a home office. Live the resort-style lifestyle you've been dreaming of with pickleball and bocce courts, a clubhouse, fitness and yoga studios, an outdoor kitchen, pool, and hot tub. Snow removal, trash, and recycling are included, allowing you more time to enjoy every day. Ask about special financing, closing cost assistance, and limited-time builder incentives available now!

Charming 3-bedroom, 2-bathroom cottage located off Berryville Ave. This inviting home features a large fully fenced back yard complete with a firepit, perfect for outdoor gatherings and relaxation. On the main level, you'll find two cozy bedrooms, kitchen with stainless appliances and a living room with shiplap accent wall. Upstairs, the spacious primary suite awaits, boasting a large dual head shower for luxurious comfort. This cottage offers a blend of modern amenities and quaint charm, making it a delightful retreat in a desirable and convenient commuter location. Ideal for those seeking comfort, privacy, and a touch of outdoor leisure, this home is ready to welcome its next residents. Recent updates to the home include electric anode installation to water heater 2024, Culigan Sulfur Cleer System in 2025, New Goodman heat pump and air handler in 2026

Four month build time from contract. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house (Aspen); it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate, brand-new residence, meticulously designed with a flowing 2,512 sq. Ft. open floor plan. The builder has redefined'standard features, integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the ent

This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great'Handyman's Delight' as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water heater installed in 2012 and the oil furnace is a newer model. This house currently is winterized and electricity shut off. (There is no lighting in the basement)

Classic charm in this brick Cape Cod located in Winchester City, just minutes from shopping, dining, and commuter routes. Set in a sidewalk-lined neighborhood, this home is full of character with arched doorways, hardwood floors throughout, and a wood-burning fireplace that creates a warm focal point in the living room. The kitchen features white cabinetry, stainless steel appliances, and granite countertops, offering both style and functionality. A bright sunroom provides additional living space overlooking the backyard, while the deck is perfect for relaxing or entertaining outdoors. A detached one-car garage in the backyard adds convenient parking and extra storage, making this home an exceptional opportunity

Welcome to this spacious 4-bedroom, 2.5-bath home offering a desirable MAIN LEVEL PRIMARY SUITE and plenty of room for everyday living and entertaining. *their va loan with a 3.25% interest rate is eligible for assumption by a veteran or active duty person or available to be assumed by a non-va person as long as they reach the credit qualifications. Contact listing agent for details. Enjoy the convenience of one-level living with the primary bedroom, laundry, kitchen, dining, and living areas all on the main floor. 3 bedrooms upper level and a loft and full bath! The well-appointed kitchen features granite countertops, a center island, pantry, Bosch cooktop, updated refrigerator and oven, and a new dishwasher. The adjoining dining area offers dimmer lighting, while the inviting living room is highlighted by dramatic cathedral ceilings, a bumpout window, and a gas fireplace. The main-level primary suite features a tray ceiling and private bath with a soaking tub, separate walk-in shower

Investors take Notice' Here's a 2 unit with long term tenants on a month to month. There is much room for growth. 1 bedroom 1 bath in the back lower level has a Brand-New Gas Heat pump installed in this unit. The Front house is a 3-bedroom 1 bath 2 level. New siding over the last couple years. New Windows & New roof 2025. Fenced backyard. Close to Downtown & Shopping

One level living in The Downs at Meadow Branch, a sought after community convenient to shopping, medical center, and Old Town Winchester. Expansive all-brick home offers 3 bedrooms, 2 bathrooms, attached 2-car garage and 2450 square feet of living space! What's better than an idyllic 1/5 acre corner lot. How about an idyllic 1/5 acre corner lot you don't have to mow? HOA fees include lawn mowing, mulching, leaf clean up, and tree and shrub maintenance! Six-panel front door with sidelights opens into a welcoming tiled foyer. Hardwood floors run through the kitchen, living and dining rooms, as well as the 2nd and 3rd bedrooms. Charming country kitchen features granite counters and stainless steel appliances, as well as a cozy breakfast nook, and access to the screened porch with ceiling fan. Large living room with gas fireplace. Formal dining room boasts chair and crown molding (note, chandelier does not convey, lighting fixture has been ordered for replacement). Primary bedroom has walk

Listing Agent Will be Hosting an Open House to the Public on Saturday 8-15-2026 from 1-4PM*. Conveniently Located Near Major Commuter Routes, Schools & Shopping Centers This Home Provides an Incredible Opportunity to Secure a Well-Priced Turn-Key 4 Bedroom 2 Bathroom Split Foyer Situated on a Private Lot Backing to Trees in Sought After Carlisle Heights Subdivision! The Sellers Addressed ALL of the Major Buyer Concerns in Preparing This Home to List Including a Brand-New HVAC System, Recently Replaced Roof, Stainless Kitchen Appliances, Granite Counter Tops, Ceramic Tile Backsplash & Main Level LVP Flooring! Custom Walk-Out Level Recreation Room, 4th Bedroom, Utility/Laundry Room, and Oversized Garage!

Welcome to 107 Ardeyth Lane! This well-maintained 4-bedroom, 3.5-bath Colonial offers generous living space, thoughtful updates, and an inviting backyard retreat. The bright kitchen features white cabinetry, Corian solid-surface countertops, stainless steel appliances, tile backsplash, and pendant and recessed lighting. Attractive laminate wood flooring flows through the main living areas, creating a warm and updated feel. The finished basement provides valuable additional living space with plenty of room for recreation, entertaining, a home office, or hobbies. Numerous improvements add comfort and peace of mind, including a new HVAC system in 2025, newer hot water heater, water softener, updated kitchen appliances, washing machine, and laminate wood flooring. The roof was reshingled approximately 7 years ago, per seller, and the storage building also received a newer roof. Step outside to a backyard designed for relaxing and entertaining. The spacious patio features a covered gazebo a

Welcome to this stunning 1997 Colonial set on 2 private acres, offering a perfect blend of main-level convenience and exceptional entertainment spaces. The main floor features a primary bedroom suite with a private bath, a light-filled living room with a cozy stone fireplace, a formal dining room, main-floor laundry, mud room, and an eat-in kitchen with stainless steel appliances. The upper level has 2 bedrooms, 1 full bathroom, a large F. R.O.G. and lots of storage. Outstanding big-ticket upgrades provide total peace of mind: reverse osmosis, softener (2025). Including a new HVAC (2023) for both zones, a 50-year roof, downspouts, and gutters (2025), a brand-new pool liner (2024), pump/filter (2026), and cover replaced 2023. Step outside to your private resort-style backyard complete with a screened-in porch, an in-ground vinyl pool, an attached garage, an asphalt driveway, and 2 detached outbuildings ideal for extra storage and with summer still in full swing, there's still plenty of

Move in ready st. Paul Townhome TBB | 3 BR | 2.5 BA | 1-Car Garage | Finished Lower Level Beautiful wooded homesites available! Offering up to 2,000 sq. Ft. of modern, open-concept living designed for today's lifestyle. Home Highlights Open-concept main level perfect for entertaining family and friends Granite countertops Stainless steel appliances Luxury vinyl plank flooring throughout the main level Upper Level Retreat Deluxe Silver primary bath with spa-inspired rain shower Spacious walk-in closet Convenient bedroom-level laundry Two additional bedrooms and a full bath Finished Lower Level Finished recreation room with full bathroom Beautiful 12' x 24' tile in all full bathrooms and laundry room Perfect space for guests, a home office, gym, media room, or playroom Additional Features Professionally designed townhome landscaping package Deako smart light switches and smart home features Energy-efficient construction and modern finishes throughout Special financing programs available

Move right into the effortless lifestyle you've been dreaming of with this beautifully designed single-level semi-attached home, ready for immediate move-in. The open-concept layout centers around a stunning kitchen featuring two-tone white and admiral cabinetry, granite countertops, and gourmet stainless steel appliances, all flowing seamlessly into the family room and inviting screened porch, perfect for relaxing or entertaining with minimal upkeep. At Hiatt Pointe, low-maintenance living extends beyond your front door. Enjoy a vibrant, active lifestyle with resort-style amenities including a sparkling outdoor pool, fitness center, tennis courts, and the peace of mind of a gated community. Spend less time on home maintenance and more time enjoying friends, wellness, and the activities you love. This is your opportunity to embrace comfort, convenience, and connection in a thoughtfully designed community. Ask about current builder incentives and make your move to easy living today