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Winchester, VA Homes for Rent

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  • /74

    Starting at $1,700 Plus Fees

    • 1 - 4 Beds

    230 Spring St, Winchester, VA 22601

    Modern designs, elegant finishes, and the most desirable amenities await you at the area's newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

    The Local

    (434) 443-7642

    230 Spring St, Winchester, VA 22601
  • /8

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    619 S Cameron St Unit 1, Winchester, VA 22601

    Charming apartment located in 2 family unit, walking distance to Old Town Winchester. Original hardwood floors, light and bright unit with washer and dryer in unit. Landlord pays water and sewer and tenant pays electric. Shared yard.

    Agent Photo

    Brock Harris

    Samson Properties

    (540) 235-5717

    619 S Cameron St Unit 1, Winchester, VA 22601
  • /38

    Starting at $1,837 Plus Fees

    • 1 - 3 Beds

    424 Ridgewood Ln, Winchester, VA 22601

    Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

    Denstock Meadow Branch LLC

    (540) 502-3204

    424 Ridgewood Ln, Winchester, VA 22601
  • /22

    $2,225 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,260 Sq Ft
    • Townhouse for Rent

    314 E Piccadilly St, Winchester, VA 22601

    Freshly updated and just two blocks from the Old Town Pedestrian Mall — this charming downtown duplex is the perfect blend of historic character and modern comfort. Recently renovated, this 3-bedroom, 1.5-bath home features gleaming hardwood floors, beautifully updated tile bathrooms, stainless steel appliances, abundant natural light, and timeless architectural details throughout. Enjoy relaxing

    Agent Photo

    Jeanne Mezzatesta

    Colony Realty

    (540) 507-2501

    314 E Piccadilly St, Winchester, VA 22601
  • /46

    Starting at $1,745 Plus Fees

    • 1 - 3 Beds

    1981 Randolph Place, Winchester, VA 22601

    Welcome to Stuart Hill Apartments — comfortable living in scenic Winchester, VA. Nestled in the picturesque Shenandoah Valley and just minutes from Historic Downtown Winchester, dining, shopping, Shenandoah University, and Winchester Medical Center, this well-maintained community offers spacious 1-, 2-, and 3-bedroom homes with full-size in-unit washers and dryers, generous closet space, and

    Stuart Hill

    (540) 546-6430

    1981 Randolph Place, Winchester, VA 22601
  • /10

    $1,700 Per Month

    • 1 Bed
    • 1 Bath
    • 9,518 Sq Ft
    • Condo for Rent

    44 S Loudoun St Unit 12, Winchester, VA 22601

    Charming one-bedroom apartment in the heart of historic downtown Winchester! Located right on the Walking Mall, you’ll be surrounded by local shops, restaurants, and entertainment. This inviting apartment features a spacious living room, an updated kitchen with newer cabinets and stainless steel appliances, convenient in-unit laundry, and one assigned parking space in a private lot. Enjoy

    Agent Photo

    Brock Harris

    Samson Properties

    (540) 413-0384

    44 S Loudoun St Unit 12, Winchester, VA 22601
  • /50

    Starting at $1,875 Plus Fees

    • 1 - 2 Beds

    2351 Quinn Ct, Winchester, VA 22601

    This new mixed-use community is centrally located in Winchester with quick access to Routes 522 and I-81. Designed for modern, convenient living, Carl's Corner features three residential buildings and a standalone commercial complex.The community offers 18 one-bedroom and 60 two-bedroom apartments, all within walking distance of shopping centers and just minutes from restaurants and

    CARLS CORNER RESIDENTIAL

    (540) 773-2474

    2351 Quinn Ct, Winchester, VA 22601
  • /7

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 2,124 Sq Ft
    • Condo for Rent

    619 S Cameron St Unit 2, Winchester, VA 22601

    Charming apartment located in 2 family unit, walking distance to Old Town Winchester. Original hardwood floors, light and bright unit with washer and dryer in unit. Landlord pays water and sewer and tenant pays electric. Shared yard.

    Agent Photo

    Brock Harris

    Samson Properties

    (540) 584-8644

    619 S Cameron St Unit 2, Winchester, VA 22601
  • /50

    Starting at $1,866 Plus Fees

    • 1 - 3 Beds

    1864 Old Jube Square, Winchester, VA 22601

    We've got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good

    The Lofts at Jubal Square

    (540) 837-6802

    1864 Old Jube Square, Winchester, VA 22601
  • /11

    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    44 S Loudoun St Unit 9, Winchester, VA 22601

    Charming 1 bedroom, 1 bathroom apartment located on the Historic Downtown walking mall, with access to all of the Shops, restaurants, museums, and more right out the front door! Just minutes from Shenandoah University, Apple Blossom Mall, and Winchester Medical Center. Parking for each unit.

    Agent Photo

    Brock Harris

    Samson Properties

    (540) 516-4753

    44 S Loudoun St Unit 9, Winchester, VA 22601
  • /40

    Starting at $1,222

    Total Monthly Price

    • 1 - 3 Beds

    121 Fay St, Winchester, VA 22602

    Live on your own terms with Fay Street Apartments. Find the comfort and convenience you crave among our one, two, and three-bedroom residences, on our well-kept premises, and in the nearby, city of Winchester, VA in the Shenandoah Valley. The property is conveniently located near top employers like Shenandoah University and Valley Health System. Our apartments open doors to a myriad of

    Fay Street Apartments

    (540) 508-8339

    121 Fay St, Winchester, VA 22602
  • /8

    $1,450 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Townhouse for Rent

    2256 Roosevelt Blvd, Winchester, VA 22601

    Very spacious 2-bedroom, 1-bathroom townhouse offering comfortable living in a well-maintained setting. Features include a rear entrance leading to a private porch area and convenient parking. Shared laundry facilities are located within the complex. Ideally situated near shopping, restaurants, and Shenandoah University. Tenant pays all utilities. No smoking, no pets, and no vaping permitted.

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    (540) 386-1044

    2256 Roosevelt Blvd, Winchester, VA 22601
  • /40

    Starting at $1,272

    Total Monthly Price

    • 1 - 3 Beds

    900-1024 N Braddock St, Winchester, VA 22601

    Welcome to Fort Collier Terrace, an inviting community you'll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, you'll find everything you need to feel right at home. Located near N Cameron Street and Martinsburg Pike, you're a stone's throw away from the top dining,

    Fort Collier Terrace

    (540) 502-3449

    900-1024 N Braddock St, Winchester, VA 22601
  • /14

    $1,700 Per Month

    • 1 Bed
    • 1 Bath
    • 9,518 Sq Ft
    • Condo for Rent

    44 S Loudoun St Unit 8, Winchester, VA 22601

    Charming one-bedroom apartment in the heart of historic downtown Winchester! Located right on the Walking Mall, you’ll be surrounded by local shops, restaurants, and all the charm downtown living has to offer. This cozy apartment features a functional layout with plenty of storage space throughout. The bedroom includes an attached sunroom, perfect for a home office, reading nook, or extra lounge

    Agent Photo

    Brock Harris

    Samson Properties

    (540) 505-0691

    44 S Loudoun St Unit 8, Winchester, VA 22601
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    Starting at $1,420

    Total Monthly Price

    • 2 - 4 Beds

    2260 Wilson Blvd, Winchester, VA 22601

    Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

    Blue Ridge Apartments

    (844) 431-3204

    2260 Wilson Blvd, Winchester, VA 22601
  • /11

    $1,350 Per Month

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Townhouse for Rent

    233 Kern St, Winchester, VA 22601

    Downtown Winchester location, full of light and super cute! This 2 bed/1 bath duplex offers a private, fenced in backyard on the north side of town. Completely renovated in 2022. Available for immediate occupancy. Application fee $50 for everyone 18 or older, no pets, monthly income minimum of 3x the monthly rent, security deposit is $1350, no previous evictions, credit score 620+, no

    Agent Photo

    Anna Fox

    NextHome Realty Select

    (540) 299-2935

    233 Kern St, Winchester, VA 22601
  • /33

    Starting at $1,550 Plus Fees

    • 1 - 2 Beds

    110 Bulmer Loop, Winchester, VA 22602

    Our community is perfect for those who enjoy spending time outside living a healthy, lively lifestyle by using the walking trails, outdoor common areas, and dog park, as well as for those who appreciate a home that is a retreat from the business of everyday life. We are conveniently located a few short miles from Shenandoah University, I-81, Rt. 8 and Rt. 50 in Winchester, VA. Our apartments

    Madison Village Apartments (Winchester)

    (540) 306-5683

    110 Bulmer Loop, Winchester, VA 22602
  • /8

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 10,400 Sq Ft
    • Condo for Rent

    23 Taft Ave Unit 3, Winchester, VA 22601

    One of the largest 2-bedroom, 2-bathroom apartments in Winchester! This spacious second-floor unit offers comfortable living in a convenient location close to shopping, restaurants, and Shenandoah University. The apartment features central air, a full-size washer and dryer, and a generous layout with plenty of living space. Step outside to enjoy a private porch, perfect for relaxing, sitting, or

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    (540) 329-2681

    23 Taft Ave Unit 3, Winchester, VA 22601
  • /17

    $1,975

    Total Monthly Price

    • 3 Beds
    • 3.5 Baths
    • 1,900 Sq Ft
    • Townhouse for Rent

    200 Tudor Dr, Winchester, VA 22603

    Gorgeous 2/3 bedroom, 3 1/2 bath beautiful town home and quiet TUDOR SQUARE TOWNHOUSES. Brand-new kitchen with walnut cabinets and granite countertops. Finished walkout basement with a full bath and plenty of closet space conserve as third bedroom or game room suite. Walk in closets. Brand-new paint job. Very private End unit. Wood floors on the main level. Washer and dryer in laundry room.

    200 Tudor Dr, Winchester, VA 22603
  • /24

    $2,225 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,260 Sq Ft
    • Townhouse for Rent

    312 E Piccadilly St, Winchester, VA 22601

    Freshly updated and just two blocks from the Old Town Pedestrian Mall — this charming downtown duplex is the perfect blend of historic character and modern comfort. Recently renovated, this 3-bedroom, 1.5-bath home features gleaming hardwood floors, beautifully updated tile bathrooms, stainless steel appliances, abundant natural light, and timeless architectural details throughout. Enjoy relaxing

    Agent Photo

    Jeanne Mezzatesta

    Colony Realty

    (540) 516-3301

    312 E Piccadilly St, Winchester, VA 22601
  • /17

    Starting at $500 Plus Fees

    • 1 - 2 Beds

    548 Brookfield Dr, Winchester, VA 22601

    We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

    Brookfield Corporate Apartments

    (540) 546-5968

    548 Brookfield Dr, Winchester, VA 22601
  • /34

    $2,100 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,369 Sq Ft
    • Townhouse for Rent

    6 E Cecil St, Winchester, VA 22601

    Charming Historic 2-Bedroom Rental Just Two Blocks from the Loudoun Street Walking Mall! Live steps from downtown in this beautifully appointed duplex featuring 2-bedrooms and an additional small office/den upstairs. The home is full of historic character and modern comfort, boasting original hardwood floors, soaring ceilings, and timeless architectural charm throughout. A dedicated dining room

    Agent Photo

    Jeanne Mezzatesta

    Colony Realty

    (540) 251-7132

    6 E Cecil St, Winchester, VA 22601
  • /20

    Starting at $1,685 Plus Fees

    • 2 - 3 Beds

    2250 Sofia Way, Winchester, VA 22601

    Cedar Hill Apartments offers well-appointed accommodations located in a convenient and relaxing environment. Only minutes away from Route 37, Route 11, and Jubal Early Drive, Cedar Hill apartments offers its tenants easy access to the Winchester Medical Center, Shenandoah University, loads of shopping and restaurants. Interior features include vaulted ceilings, gas fireplace, wood vanity

    CEDAR HILL APARTMENTS

    (540) 502-3991

    2250 Sofia Way, Winchester, VA 22601
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    $2,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    21 S Stewart St Unit 4, Winchester, VA 22601

    Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    (540) 318-1292

    21 S Stewart St Unit 4, Winchester, VA 22601
  • /20

    Starting at $1,525 Plus Fees

    • 1 - 3 Beds

    221 Peppertree Ln, Winchester, VA 22601

    Tastefully designed 1, 2 and 3 bedroom floor plans and richly landscaped surroundings make for a welcome sight to call your home. Located in the heart of Winchester, Peppertree offers the conveniences of city living in a park-like setting. Peppertree is in close proximity to shopping, restaurants, schools and Winchester Medical Center.

    Peppertree VA

    (540) 502-4841

    221 Peppertree Ln, Winchester, VA 22601
  • /13

    $1,500 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    21 S Stewart St Unit 2, Winchester, VA 22601

    2 Bedroom Apartment for Rent – Downtown Winchester Great 2nd-floor apartment located in downtown Winchester with 2 bedrooms and 1 bathroom. This home is just a short walk from Old Town Winchester, giving you easy access to local restaurants, shops, and entertainment. The apartment features very spacious bedrooms, a comfortable family room, and a fully enclosed back porch, perfect for relaxing or

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    (540) 534-4239

    21 S Stewart St Unit 2, Winchester, VA 22601
  • /20

    Starting at $1,565 Plus Fees

    • 2 - 3 Beds

    660 Pemberton Dr, Winchester, VA 22601

    Pemberton Village Apartments in Winchester VA is located in the prestigious Meadow Branch subdivision near the intersection of Jubal Early Drive and Harvest Drive. It is a ten building, 120 unit community easily assessable from Interstate 81 or Route 37. Conveniently located near the Apple Blossom Mall, fitness centers, John Handley High School, and Valley Health Medical Center; Pemberton Village

    PEMBERTON

    (540) 502-4138

    660 Pemberton Dr, Winchester, VA 22601
  • /20

    Starting at $1,610 Plus Fees

    • 1 - 2 Beds

    2310 Valor Dr, Winchester, VA 22601

    Harrison Plaza is a new mixed-use development located at the intersection of Hope Drive and Valor Drive in the heart of Winchester, VA. This three-building community offers 70 one- and two-bedroom spacious modern apartments minutes away from local shopping centers, restaurants, and entertainment venues.Interior features include an open floor plan with stylish cabinets, granite countertops,

    HARRISON PLAZA RESIDENTIAL

    (540) 502-3969

    2310 Valor Dr, Winchester, VA 22601
  • /9

    Starting at $1,800 Plus Fees

    • 1 - 2 Beds

    210 S Cameron St, Winchester, VA 22601

    This fully furnished and recently renovated property is located in the heart off Old Town Winchester and includes a log cabin structure, premium appliances, granite countertops and assigned parking spaces.Come and enjoy the excitement of living in Old Town with many excellent restaurants and drinking establishments , six breweries, multiple music venues, fabulous shopping, museums and art

    (540) 486-2865

    210 S Cameron St, Winchester, VA 22601
  • /20

    Starting at $1,150 Plus Fees

    • 1 - 2 Beds

    800 Thomas Ct, Winchester, VA 22601

    Now Leasing: 1 & 2 Bedroom Apartments Available Now! In-unit washer and dryerWater and garbage includedEnjoy a serene, peaceful settingDon't miss out—these are first come, first serve!

    North Winchester Apartments

    (540) 546-5335

    800 Thomas Ct, Winchester, VA 22601
  • /20

    Starting at $1,600 Plus Fees

    • Studio - 2 Beds

    114 N Loudoun St, Winchester, VA 22601

    Brand new fully furnished extended stay apartments in the heart of Old Town Winchester Virginia including all utilities, washer /dyer, high speed internet, free nightly and weekend parking ( 5pm to 8 am), keyless entry, 10' ceilings, exposed brick interior partitions and optional weekly cleaning.. More information can be found at themerchantsuites

    (540) 486-2842

    114 N Loudoun St, Winchester, VA 22601
  • /20

    Starting at $1,469

    Total Monthly Price

    • 2 - 3 Beds

    124 Castlebridge Ct, Winchester, VA 22602

    Preston Place Apartments and Townhomes are a remarkable blend of style and value. Almost everything is nearby, from schools to shopping, restaurants, parks and interstate highways. Conveniently located on Airport Drive one-half mile from the Winchester Regional Airport. Dulles Airport is also less than thirty minutes away. It’s hard to find a more convenient location.

    Preston Place

    (540) 306-5726

    124 Castlebridge Ct, Winchester, VA 22602
  • /10

    $995 Plus Fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    406 N Loudoun St Unit 3, Winchester, VA 22601

    Property Id: 2365934Efficiency Apartment for Rent - Downtown WinchesterEnjoy simple, affordable living in this bright efficiency apartment conveniently located in Downtown Winchester. This open-concept unit features a private bathroom and kitchenette.Large windows fill the apartment with natural light, creating a comfortable and inviting atmosphere. The kitchenette includes a

    (540) 546-4495

    406 N Loudoun St Unit 3, Winchester, VA 22601
  • /20

    $2,450 Plus Fees

    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft
    • Townhouse for Rent

    117 Lakota St, Winchester, VA 22602

    Welcome to your new home in beautiful Winchester, VA! This inviting property offers a perfect blend of comfort and convenience, ideal for anyone looking to settle in a vibrant community.Key property features include spacious living areas designed for relaxation. The location is simply fantastic, with several great restaurants and department stores nearby. For healthcare needs, Valley

    (540) 486-2697

    117 Lakota St, Winchester, VA 22602
  • /20

    $2,312

    Total Monthly Price

    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft
    • Townhouse for Rent

    189 Sioux Lp, Winchester, VA 22602

    This spacious 4-bedroom, 3.5-bathroom townhome offers comfort and modern conveniences, spanning over 1889 sq ft. - Electric range, dishwasher, microwave, garbage disposal, and refrigerator- Stainless steel appliances and stone countertops- Garage attached for easy parking- In-unit laundry for added convenience- Wood plank and carpet flooring throughout- Central cooling

    (659) 204-1241

    189 Sioux Lp, Winchester, VA 22602
  • /11

    $1,498 Plus Fees

    • 2 Beds
    • 1.5 Baths
    • 1,047 Sq Ft
    • Condo for Rent

    1105 Franklin St, Winchester, VA 22601

    Welcome to your new home in the charming city of Winchester, VA! This delightful property is perfectly situated near a vibrant selection of restaurants and department stores, making it easy to enjoy local dining and shopping experiences. For outdoor enthusiasts, Jim Barnett Park is within walking distance, offering a serene escape for leisure activities. Plus, Valley Health is just a quick

    (540) 573-2162

    1105 Franklin St, Winchester, VA 22601
  • /9

    $1,495 Plus Fees

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    2640 Valley Ave Unit 1, Winchester, VA 22601

    Property Id: 2608151If interested, please call, we do not respond to email or requests. 1 Bedroom 1 Bath 600 sqft. $1395/Month 1 Year Lease. All Utilities Included. First and Security Due at Signing. Stove, dishwasher, fridge, washer, and dryer provided inside unit. Individual Unit Central heat and air. No Smoking. No Pets.. Meticulously maintained, serious inquiries ONLY!

    (540) 534-0993

    2640 Valley Ave Unit 1, Winchester, VA 22601
  • /17

    $2,200 Plus Fees

    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft
    • Condo for Rent

    129 Garber Ln, Winchester, VA 22602

    Agents welcome!Welcome to your new home in the heart of Winchester, VA! This charming rental property offers an inviting atmosphere and is ideally situated near various local amenities that enhance your lifestyle.This property features spacious bedrooms and bathrooms, providing comfortable living spaces for you and your family. With a well-designed floor area, you will feel right at

    (540) 386-1610

    129 Garber Ln, Winchester, VA 22602
  • /9

    $1,300 Plus Fees

    • 1 Bed
    • 1 Bath
    • 712 Sq Ft
    • Condo for Rent

    115 W Monmouth St Unit 2, Winchester, VA 22601

    Property Id: 2606494One bedroom, one bath (115 W. Monmouth Street) in a beautiful area of Historic Downtown Winchester; just minutes from Shenandoah University, Apple Blossom Mall, Winchester Medical Center, and major commuter routes, this apartment is ideally suited for professionals, students, or anyone seeking a blend of convenience and neighborhood community. $1300/month. 712 square

    (540) 486-2712

    115 W Monmouth St Unit 2, Winchester, VA 22601
  • /25

    $1,800

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,250 Sq Ft
    • Condo for Rent

    21 N Braddock St, Winchester, VA 22601

    Located in Historic Downtown Winchester on North Braddock Street- 1 block west of Walking Mall. Restaurants, shops, transportation all within walking distance.Hardwood floors throughout historic property, large open rooms, 9' ceilings. 1 of 4 units total in building. Second Floor. No Pets/No Smoking. Large Kitchen features Stove, Microwave, Oven, Full size Fridge -AND a large walk-in

    21 N Braddock St, Winchester, VA 22601

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Why Live in Winchester

Winchester, located in the Shenandoah Valley of Virginia, is a small but rapidly growing town known for its apple-themed events, historic downtown, and accessibility to larger cities like Washington D.C. and Loudoun County. The town's economy is driven by health care, retail, and manufacturing, with Valley Health being a major employer. Commuters often use Interstate 81 and U.S. Route 50 for the 75-mile trip to Northern Virginia and D.C. Winchester Transit provides local bus services, and Dulles International Airport is 50 miles away. The town experiences humid summers and mild winters, with occasional minor flooding due to heavy rainfall. Winchester's housing market offers more affordable options compared to neighboring counties, with historic homes near downtown featuring Craftsman and Colonial Revival designs. The Shenandoah Apple Blossom Festival is a major annual event, attracting around 250,000 visitors. Residents enjoy performances at local theaters, shopping at the Apple Blossom Mall, and dining in Old Town Winchester. Outdoor enthusiasts can explore Jim Barnett Park, the Museum of the Shenandoah Valley, and nearby Shenandoah National Park. Winchester City Public Schools serve over 4,000 students and are highly rated, while Shenandoah University offers strong liberal arts and performing arts programs. Despite its small size, Winchester boasts a rich history with several Civil War sites and the Patsy Cline Historic House.

Frequently Asked Questions

How much does it cost to rent a home in Winchester, VA?
The median rent for a home in Winchester, VA is $1,725 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while single-family homes and townhouses are currently more expensive.
How much do you need to make to afford rent in Winchester, VA?
To comfortably afford the median rent in Winchester, VA, a household needs to earn roughly $69,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,725 per month in Winchester, VA, renters typically need to show $5,175 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Winchester, VA?
In Winchester, VA, the price-to-rent ratio is 20.0, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Trends in Winchester, VA

Rental Home Trends

Number of Homes for Rent
158
Median Rent
$1,725
Median Single Family Home Rent
$1,900
Median Townhouse Rent
$2,000
Median Condo Rent
$1,400
How to Rent a Home