Winchester, VA Condos for Rent under $2,000

We are okay with Short term or Yearly lease. Please contact Property Manager with inquiries.Freshly Remodeled Studio Apartment available. Centered in the heart of Winchester, walking distance to shops, restaurants, and entertainment. Utilities and WIFI are included at no charge. No pets allowed. Come and enjoy all of what Winchester has to offer. $995 per Month or $275 per Week On-site

Raj Patel Ikon Realty - Ashburn

Conveniently located in the heart of Winchester, 2264 Papermill Road #C offers comfortable and affordable living close to shopping, restaurants, and major commuter routes. This 1-bedroom, 1-bath apartment features a functional layout with spacious living areas, natural light, and off-street parking. The home includes forced-air heat, window-unit cooling, and a convenient in-town location just

Joseph Clotzman Cambridge Premier Realty, LLC.

RECENTLY RENOVATED, ALL-BRICK BUILDING THAT WAS COMPLETELY REDONE OVER LAST SEVERAL YEARS * UNIT HAS NEWER STAINLESS-STEEL APPLIANCES AND NEWER VINYL-PLANK FLOORING * EXTERIOR OF BUILDING WAS PAINTED IN 2018. NEW WINDOWS, NEW GUTTERS AND NEW ROOF ADDED IN 2018. ALL NEW ELECTRIC SERVICE IN 2018, ALSO * AWESOME KITCHEN W/NEWER CABINETS & GRANITE C'TOPS * REDONE BATH W/CERAMIC TILE FLOORS & TUB

John Gregory Holmes Samson Properties

One bedroom one bath apartment is ground level has been completely renovated and ready for your personal touch. There is a $25 additional fee monthly for water, sewer trash. Pets on a case by case basis with additional pet deposit required and $25 in monthly pet rent, and no smoking allowed.

Ashley Crabill Coldwell Banker Premier

Charming 1-bedroom, 1-bath apartment located in the heart of historic downtown Winchester! This inviting home features a bright living room with beautiful built-in shelving and passthrough openings to the kitchen, creating an open and connected feel. The updated kitchen includes stainless steel appliances, a stylish tiled backsplash, granite countertops, and crisp white cabinetry. Enjoy the

James King RE/MAX Roots

Welcome to Apt. 1 at 4 W. Cork Street, a beautifully located residence in the heart of historic downtown Winchester. This inviting apartment offers the perfect blend of character, convenience, and city living. Enjoy easy access to local restaurants, coffee shops, boutiques, entertainment, and the vibrant Old Town walking mall—all just steps from your front door.

Patrick Slate Keller Williams Realty

Welcome home to 142 N Washington St #7! This 1-bedroom, 1-bath apartment offers comfortable living in the heart of Winchester with water, sewer, and trash included in the rent. Tenant is responsible for electricity. Enjoy one of Winchester’s most walkable locations, just minutes from the Old Town Winchester Walking Mall. Surrounded by historic charm, local shops, restaurants, boutiques, coffee

Chris Roszko Colony Realty

Welcome home to 105 N Loudoun St #1. This is the apartment you've been searching for! This fantastic second floor apartment is above the Village Square restaurant, on the walking mall. This is a 1 bedroom apartment with an additional "Bonus Room" that could be used as an office, storage or a content creation room! This unit has so much charm and character. Freshly refinished hardwood floors and

Chris Roszko Colony Realty

Historic Downtown Winchester: 1st floor 1 bedroom 1 bath apartment AVAILABLE NOW for rent! Water/sewer/trash included, tenant pays electric. No smoking and no animals please. VAR or NVAR application is fine w/ $50 app fee paid by cash or money order or you may apply online thru website. Max 2 person occupany.

Mandie Gladwell OliveTree Property Group, LLC

Beautifully Renovated Unit Two level townhome with Central A/c and Heat pump*Full size Washer & Dryer*Hardwood like Floors* Huge Brand New Eat-In Kitchen*Granite counters & Stainless Steel Appliances*Spacious bedrooms*Large closets*Individually controlled HVAC and hot water heater*Plenty of parking*1 mile from great shopping on Valley Avenue, 10 minute from downtown Winchester and 9 minute from

Ashley Crabill Coldwell Banker Premier

Historic Downtown Winchester: 2nd floor 1 bedroom apartment AVAILABLE NOW for rent! Water/sewer/trash included, tenant pays electric. No smoking and no animals please. $50 app fee paid by cash or money order or you may apply online thru website.

Mandie Gladwell OliveTree Property Group, LLC

Available Immediately!Character filled second level 2-bedroom, 1-bath apartment available for rent. An affordable opportunity for those seeking a basic and comfortable place to call home. Just minutes to Old Town Winchester, restaurants and grocery stores. Pets allowed with some restrictions and fees.

Danielle Spriggs Samson Properties

Welcome home to 105 N Loudoun St Apartment #2. This fully renovated apartment is the one you've been searching for! This fantastic second floor apartment is above the Village Square restaurant, on the walking mall. Minutes to Shenandoah University. Includes 1 assigned parking spot downtown! Shared washer and dryer a few steps from your door step. Water, Sewer, and trash are included! Call today

Chris Roszko Colony Realty

History Meets Modern Day On the doorstep of Winchester’s Historic Pedestrian Mall this Modern and Chic Apartment awaits your occupancy. The short distance to the walking mall with the perfect new brick sidewalks is a delight! Imagine this stroll every time you would like some fresh air, coffee, a meal or some live music! This historic all brick building has been completely restored with gleaming

Jen Richards MarketPlace REALTY

Welcome to your new home at Brookland Court! This lovely penthouse 2-bedroom, 2-bathroom condo is conveniently located on the 2nd floor of building 121 in Park Place Community. Conveniently located close to I-81 and Rt-7. Newer luxury vinyl plank wood floors throughout the home. Brand new appliances (installed April 2026). The primary bedroom features an attached bathroom and walk in closet,

Yvonne Holland Samson Properties

Downtown 1bedroom, 1 bath apartment within 2 blocks of the downtown walking mall. All utilities are provided (electric, water, sewer, internet and satellite TV) move in an enjoy the location of historic downtown Winchester living. Walk to breweries, restaurants and entertainment.

Curtis Siever NextHome Realty Select