Cheap homes for sale & real estate in Winchester, VA

172 homes

Sort:

Recommended

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
This beautifully updated all-brick ranch in Winchester offers true main-level living and a peaceful country setting with incredible mountain views. A long circular driveway welcomes you to this turnkey home featuring a brand-new HVAC system, architectural roof, and modern finishes throughout. Inside, enjoy a renovated kitchen with stainless steel appliances, new cabinetry, and gorgeous countertops, opening to a cozy breakfast nook and a spacious family room framed by breathtaking views. The main level includes four bedrooms, one a private primary suite with en-suite bath, plus an updated hall bath. Luxury vinyl flooring flows throughout the living areas, with new carpet in the bedrooms. The

$325,000

4 beds2 baths1,450 sq ft

3221 Laurel Grove Rd, Winchester, VA 22602

1.74 acre lot • Built 1950 • Listed 3 days

(240) 309-6000

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
Step into this well-cared-for home in the peaceful Greenwood Heights neighborhood convenient to Route 50, Route 7, and Winchester. This easy single-floor layout features 3 bedrooms and 1.5 baths and is ideal for those just starting out or looking to downsize. The comfortable floor plan is ready for your personal touch, and the spacious fenced backyard with deck and storage shed are perfect for kids, pets, tools and toys. With its solid brick construction and inviting setting, this home offers a wonderful opportunity to settle in and make it your own. And with the holidays approaching, why not give yourself the gift of a new place to call home?

$356,000

3 beds1.5 baths1,164 sq ft

111 Meadowview Ct, Winchester, VA 22602

Built 1988

(540) 665-0360

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
Great opportunity to own this 2-bed, 1-bath Winchester City charmer that sits just minutes from Shenandoah University and the Old Town walking mall. Main level living with a bright comfortable living area, an eat-in kitchen home that includes a bonus room providing flexible space for an office, playroom, fitness area, or guest room, central air and the convenience of an in-home washer & dryer Outdoors, the large, fenced in backyard is ready for pets, play, or gardens, and the storage shed keeps tools and gear organized. Whether you’re seeking a first home, downsizing, or investing near campus, this location delivers everyday convenience, and a welcoming neighborhood feel! clos

$265,000

2 beds1 bath882 sq ft

204 Shenandoah Ave, Winchester, VA 22601

Built 1954 • Listed 2 days

(703) 669-0099

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
Turn Key + Convenience + Outstanding Value! Perfect 2/1 open floorplan single family home on Senseny Road with HUGE backyard! Hardwood floors, newer roof, updated throughout! Best value in Frederick County! Meticulous condition and will go fast! Only $279K!

$279,000

2 beds1 bath800 sq ft

2003 Senseny Rd, Winchester, VA 22602

Built 1967 • Listed 3 days

(540) 662-9937

COMING SOON

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
Beautiful 3 bed, 2.5 bath split foyer on a gorgeous . 52-acre lot backing to mature trees. Enjoy outdoor living on the paver patio with built-in firepit, surrounded by thoughtful landscaping that enhances curb appeal and privacy. Spacious interior layout, bright natural light, and a peaceful setting make this home an ideal blend of comfort and convenience. Enjoy granite countertops, table space, stainless steel appliances, electric cooking, and a center island with breakfast seating in the kitchen. Luxury vinyl plank flooring throughout. Let this one impress from the moment you arrive.

$359,000

3 beds2.5 baths1,719 sq ft

415 Quail Dr, Winchester, VA 22602

0.52 acre lot • 2 garage spots • Built 2021

(540) 686-7362

Property at 114 Woodys Pl, Winchester, VA 22602, 3 beds, 2 baths

$299,999

3 beds2 baths1,615 sq ft

114 Woodys Pl, Winchester, VA 22602

(540) 662-3484

Property at 127 Shirley St, Winchester, VA 22601, 4 beds, 2 baths

$365,000

4 beds2 baths1,780 sq ft

127 Shirley St, Winchester, VA 22601

(540) 665-0360

Property at 225 Fox Dr, Winchester, VA 22601, 3 beds, 1.5 baths

$395,000

3 beds1.5 baths1,274 sq ft

225 Fox Dr, Winchester, VA 22601

(540) 665-0360

Property at 108 Martin Dr, Winchester, VA 22602, 2 beds, 1 bath

$285,000

2 beds1 bath997 sq ft

108 Martin Dr, Winchester, VA 22602

(540) 348-4911

Property at 126 Plainfield Dr, Winchester, VA 22602, 4 beds, 1.5 baths

$335,000

4 beds1.5 baths1,456 sq ft

126 Plainfield Dr, Winchester, VA 22602

(540) 686-7362

Property at 203 Crestwood Ln, Winchester, VA 22602, 2 beds, 2 baths

$379,000

2 beds2 baths1,590 sq ft

203 Crestwood Ln, Winchester, VA 22602

(540) 450-2747

Property at 207 Eastside, Winchester, VA 22602, 4 beds, 3.5 baths

$314,000

4 beds3.5 baths1,840 sq ft

207 Eastside, Winchester, VA 22602

(540) 662-4500

Property at 230 Monteith Dr, Winchester, VA 22601, 3 beds, 3.5 baths

$379,990

3 beds3.5 baths1,784 sq ft

230 Monteith Dr, Winchester, VA 22601

(240) 457-9391

Property at 222 Monteith Dr, Winchester, VA 22601, 3 beds, 3.5 baths

$379,990

3 beds3.5 baths1,784 sq ft

222 Monteith Dr, Winchester, VA 22601

(240) 457-9391

Property at TBB Monteith Dr Unit DEEP CREEK II, Winchester, VA 22601, 3 beds, 2.5 baths

$409,990

3 beds2.5 baths2,060 sq ft

TBB Monteith Dr Unit DEEP CREEK II, Winchester, VA 22601

(240) 457-9391

Property at 209 Monteith Dr, Winchester, VA 22601, 3 beds, 3.5 baths

$379,990

3 beds3.5 baths1,784 sq ft

209 Monteith Dr, Winchester, VA 22601

(240) 457-9391

Property at 166 Graywolf Trl, Winchester, VA 22602, 4 beds, 3 baths

$374,900

4 beds3 baths1,840 sq ft

166 Graywolf Trl, Winchester, VA 22602

(866) 825-7169

Property at 100 Winns Cir, Winchester, VA 22602, 4 beds, 2.5 baths

$400,000

4 beds2.5 baths2,636 sq ft

100 Winns Cir, Winchester, VA 22602

(540) 662-4500

Property at 3339 N Frederick Pike, Winchester, VA 22603, 5 beds, 2 baths

$349,999

5 beds2 baths3,378 sq ft

3339 N Frederick Pike, Winchester, VA 22603

(540) 635-8000

Property at 7 N Purcell Ave, Winchester, VA 22601, 3 beds, 3 baths

$375,000

3 beds3 baths2,016 sq ft

7 N Purcell Ave, Winchester, VA 22601

(540) 773-8475

Property at 163 Denny Ln, Winchester, VA 22603, 3 beds, 2 baths

$344,990

3 beds2 baths1,152 sq ft

163 Denny Ln, Winchester, VA 22603

(866) 825-7169

Property at 815 Pheasant Dr, Winchester, VA 22602, 2 beds, 1 bath

$245,000

2 beds1 bath960 sq ft

815 Pheasant Dr, Winchester, VA 22602

(540) 686-7362

Property at 1080 Airport Rd, Winchester, VA 22602, 2 beds, 2 baths

$300,000

2 beds2 baths1,099 sq ft

1080 Airport Rd, Winchester, VA 22602

(540) 433-7369

Property at 1006 S Cameron St, Winchester, VA 22601, 4 beds, 1 bath

$289,500

4 beds1 bath1,732 sq ft

1006 S Cameron St, Winchester, VA 22601

(540) 665-0360

Property at 100 Maury Way, Winchester, VA 22602, 3 beds, 2.5 baths

$385,000

3 beds2.5 baths1,678 sq ft

100 Maury Way, Winchester, VA 22602

(703) 430-9008

Property at 115-12 Brookland Ter #12, Winchester, VA 22602, 2 beds, 2 baths

$250,000

2 beds2 baths1,173 sq ft

115-12 Brookland Ter #12, Winchester, VA 22602

(540) 662-0323

Property at 728 Green St, Winchester, VA 22601, 4 beds, 1.5 baths

$325,000

4 beds1.5 baths1,659 sq ft

728 Green St, Winchester, VA 22601

(304) 262-8700

Property at 423 Highland Ave, Winchester, VA 22601, 3 beds, 2 baths

$269,000

3 beds2 baths1,300 sq ft

423 Highland Ave, Winchester, VA 22601

(540) 348-4911

Property at 627 Watson Ave, Winchester, VA 22601, 3 beds, 1 bath

$299,990

3 beds1 bath1,205 sq ft

627 Watson Ave, Winchester, VA 22601

(540) 348-4911

Property at 117 W Oates Ave, Winchester, VA 22601, 3 beds, 1 bath

$330,000

3 beds1 bath1,237 sq ft

117 W Oates Ave, Winchester, VA 22601

(540) 773-8475

Property at 2901 Sorrell Ct, Winchester, VA 22601, 3 beds, 1.5 baths

$279,900

3 beds1.5 baths1,332 sq ft

2901 Sorrell Ct, Winchester, VA 22601

(540) 259-4090

Property at 4403 Back Mountain Rd, Winchester, VA 22602, 3 beds, 2.5 baths

$449,900

3 beds2.5 baths2,012 sq ft

4403 Back Mountain Rd, Winchester, VA 22602

(540) 686-7362

Property at 305 Sutton Ct, Winchester, VA 22601, 2 beds, 1.5 baths

$305,000

2 beds1.5 baths1,214 sq ft

305 Sutton Ct, Winchester, VA 22601

(540) 348-4911

Property at 129 Brookland Ter #1, Winchester, VA 22602, 2 beds, 2 baths

$250,000

2 beds2 baths1,173 sq ft

129 Brookland Ter #1, Winchester, VA 22602

(540) 662-0323

Property at 1133 Tomahawk Trl Trl, Winchester, VA 22602, 3 beds, 2 baths

$419,000

3 beds2 baths2,325 sq ft

1133 Tomahawk Trl Trl, Winchester, VA 22602

(540) 662-3484

Property at 177 Dicks Hollow Rd, Winchester, VA 22603, 2 beds, 1 bath

$275,000

2 beds1 bath572 sq ft

177 Dicks Hollow Rd, Winchester, VA 22603

(540) 662-2300

Property at 107 Dale Ct, Winchester, VA 22602, 4 beds, 2 baths

$375,000

4 beds2 baths1,608 sq ft

107 Dale Ct, Winchester, VA 22602

(540) 662-0323

Property at 119 Buffalo Trl, Winchester, VA 22602, 5 beds, 3.5 baths

$349,900

5 beds3.5 baths2,440 sq ft

119 Buffalo Trl, Winchester, VA 22602

(703) 679-1700

Property at 2660 Wardensville Grade, Winchester, VA 22602, 3 beds, 2.5 baths

$400,000

3 beds2.5 baths1,920 sq ft

2660 Wardensville Grade, Winchester, VA 22602

(304) 262-0800

Property at 309 Raccoon Dr, Winchester, VA 22602, 3 beds, 2 baths

$252,900

3 beds2 baths931 sq ft

309 Raccoon Dr, Winchester, VA 22602

(540) 686-7362

Property at 222 Crestwood Ln, Winchester, VA 22602, 2 beds, 2 baths

$369,000

2 beds2 baths1,260 sq ft

222 Crestwood Ln, Winchester, VA 22602

(540) 665-0360

Viewing page 1 of 5

Cheap Homes for Sale in Winchester

There are currently 172 cheap homes for sale in Winchester at a median listing price of $400K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 51 days and receive 3 offers. Popular neighborhoods include Historic District, and Kernstown. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 25 homes have been sold in Winchester. In addition to houses in Winchester, there was also 1 condo, 16 townhouses, and 5 multi-family units for sale in Winchester last month. Winchester is a moderately walkable city in Frederick County with a Walk Score of 51. Winchester is home to approximately 25,909 people and 22,642 jobs. Find your dream home in Winchester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. Our Winchester real estate stats and trends will give you more information about home buying and selling trends in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Winchester, VA

Neighborhoods

Nearby Cities

Zip Codes

Nearby Cities with Cheap Homes

Nearby Neighborhoods with Cheap Homes

Kernstown cheap homes for sale

More to explore in Winchester, VA

Featured
Price

How to buy a house in Winchester, VA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Virginia

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.