Winchester, VA Homes for Sale with AC under $300,000

Great Investment property or 1st home! Charming and spacious 2 bedroom, 1.5 baths Townhouse. Extra large living room has hardwood floors, lots of natural light, Eat in Kitchen with full size washer & dryer and powder room on the main level. Back door opens to fenced backyard with small storage area. Upstairs has two XL large bedrooms (can fit a king & queen bed), both with hardwood floors, 2

Nancy Tessman EXP Realty, LLC

Move‐in ready 2 bedroom, 1 bath rancher featuring easy one‐level living and a covered front porch on a quiet lot. This home has been updated throughout, including LVP flooring, mini‐split heating and cooling with back up propane wall heat, new water heater, updated kitchen, and new washer and dryer.A circular driveway provides convenient access, and the nice‐sized outbuilding with electric

Julie Shiley Coldwell Banker Realty

Tucked away at the end of the neighborhood and surrounded by serene woods, 610 Puma Trl offers the perfect blend of privacy and charm. This adorable 2-bedroom, 1-bath rancher is a true retreat, featuring modern updates and a warm, inviting layout. Enjoy peaceful living with beautiful natural surroundings while still being conveniently located near town. A rare opportunity to own your own slice of

James Podoley EXP Realty, LLC

Don't miss your opportunity to own this turn key, meticulously maintained 3 bedroom/2.5 bath townhome in sought after Carlisle Heights! The main level is the heart of the home and features gleaming hardwood flooring throughout, a large living room, gourmet updated kitchen with white cabinetry, stainless steel appliances, quartz counters and a modern sink that opens to an oversized dining room.

Paul Thistle Take 2 Real Estate LLC

Great investment opportunity! This tenant-occupied property is currently rented for $1,650/month with a lease in place through January 2027, offering immediate income. Ideal for investors looking for a turnkey rental. Seller is motivated, don’t miss this opportunity! Welcome to 138 Parkside Drive, a charming 3-bedroom, 1.5-bath townhome in a quiet, convenient Winchester neighborhood! This home

Jas Kaur Prime Properties DMV, LLC.

Major Price Reduction! Welcome to this beautifully renovated 2-bedroom, 1-bath ranch-style home nestled in the peaceful, private community of Wild Acres. Surrounded by trees, this cozy 960 sq ft retreat offers the perfect blend of modern updates and natural charm. Inside, you’ll find a bright, refreshed interior with thoughtful updates throughout. Major improvements—including a new well, septic

Brandy Clem Johnston and Rhodes Real Estate

Conveniently located in Winchester City, this 3-bedroom, 1.5-bath ranch-style home features a primary bedroom with a private half bath, two additional bedrooms, and a hall bath. The spacious living room opens to the dining area and kitchen, creating a comfortable flow for everyday living. The kitchen includes a newer refrigerator. Step outside to a screened-in back porch overlooking the level,

Leah Clowser RE/MAX Roots

Nestled in Orchard Terrace, this beautifully updated Colonial home is ideally located within Winchester city limits, just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen features new cabinets, granite countertops, stainless steel appliances, a new sink and faucet, and vinyl plank flooring. The bathroom includes a new vanity, vanity

Jennifer Sacco RE/MAX Roots

Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painted with new luxury vinyl planking throughout the entire house. Brand new bathroom with tub /shower. Open floor plan with bedrooms on each end of the house for privacy. 2 sheds that convey to store whatever your heart desires. Front deck to be stained as soon as weather permits. Come out and and enjoy all the

Jacquelyn Rizzari MarketPlace REALTY

Newly remodeled turn-key starter home with modern updates. 2-bedroom 1-bathroom rancher just minutes from Winchester! Situated on a private .29-acre lot that backs to trees, this home offers peaceful country living with convenient access to Route 50 and town amenities. Interior features include luxury vinyl plank flooring throughout, stainless steel appliances, upgraded countertops, and a modern

Sheila Pack RE/MAX Roots

Time to sell - you get a great deal - $36,000 rental income, low maintenance, tenants in place. This is a great starter property for those looking to build a real estate portfolio or add to an existing one. Both apartments were completely rehabbed last year - new wiring and plumbing, new appliances, including washer and dryer, new carpet and vinyl plank flooring installed and fenced backyards.

Teri Domanski Corcoran McEnearney

Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large windows that let in plenty

Heloisa Amar Samson Properties

Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of

Jodi Costello ERA Oakcrest Realty, Inc.

Rebecca Sims Century 21 Redwood Realty

Coming June 2026. Blue Ocean Modulars introduces The Laurel, a new modular home to be located at 603 Opossum Trail in Wilde Acres. Nestled against a forested backdrop and built with high-quality workmanship, this residence showcases modern modular construction designed for durability, comfort, and long-term value. The home features Insul-Stud framing, a cutting-edge system that enhances

Rebecca McTavish Long & Foster Real Estate, Inc.

Welcome to 149 Royal Avenue, a charming Winchester home offering 2 bedrooms, 1 full bath, and approximately 936 square feet of comfortable living space. Built in 1943, this home blends timeless character with a practical layout and everyday comfort. Nestled on a quiet street, the property features a large fenced-in yard with plenty of space to relax, garden, or enjoy the outdoors. Conveniently

Holly Slawter Samson Properties