Cheap homes for sale & real estate in Winchester, VA

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OPEN SUN, 12PM TO 3PM

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
Welcome to 912 Opequon Ave! This versatile, beautifully updated split-foyer home offers 5 bedrooms, 2 full bathrooms, and approximately 1,810 finished square feet of living space in a convenient, walkable Winchester neighborhood. Whether you're looking for a spacious primary residence, room for multigenerational living, or an opportunity to generate rental income, this property offers the flexibility to fit your needs. The main level features a bright, inviting living and dining area that flows seamlessly onto a spacious, brand-new TREX deck—perfect for relaxing, entertaining, or enjoying the outdoors. The kitchen is equipped with stainless steel appliance, including a smooth-top rang

$409,900

5 beds2 baths1,710 sq ft

912 Opequon Ave, Winchester, VA 22601

New kitchenette • Large rear deck • Remodeled full bath

(703) 539-7062

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
Welcome to 338 E Piccadilly Street, a beautifully updated 3-bedroom, 2-bathroom home perfectly positioned in a highly convenient Winchester location. Overflowing with natural light and seamless charm, this move-in ready residence effortlessly blends classic architectural characteristics with high-end modern finishes and thoughtful details throughout. The inviting curb appeal begins with a freshly paved front walkway leading to a covered front porch framed by classic arches and complete with an adorable porch swing. Inside, the bright foyer opens into a warm living room with rich hardwood flooring that flows seamlessly into the beautifully redesigned kitchen. A standout focal point of the ma

$399,900

3 beds2 baths1,422 sq ft

338 E Piccadilly St, Winchester, VA 22601

Covered front porch • Exposed brick pillar • Separate wet bar

(540) 662-0323

OPEN SUN, 1PM TO 3PM3D WALKTHROUGH

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
Looking for a ranch-style home with plenty of potential and NO HOA? Offered for the first time by its original owner, this home offers convenient main-level living plus a finished bonus room above the garage, accessed by interior stairs located just off the kitchen. This additional finished space offers plenty of flexibility for a home office, hobby room, playroom, or whatever best fits your needs. Inside, you’ll find hardwood flooring in the foyer and living room, along with a gas fireplace that adds warmth and character to the main living space. The spacious primary suite features a walk-in closet, jetted tub, and an upgraded tiled walk-in shower with a built-in seat. A ramp at the

$399,900

3 beds2 baths1,818 sq ft

318 Stonehenge Rd, Winchester, VA 22601

Hardwood flooring • Main level living • Finished bonus room

(540) 667-9097

FOR SALE BY OWNER

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
This house was completely rebuilt. It has new HVAC, electrical, plumbing, windows, bathrooms, kitchen and a new large garage. Two new bedrooms and a full bathroom in the finished basement.

$425,000

4 beds2 baths2,000 sq ft

719 Pennsylvania Ave, Winchester, VA 22601

New plumbing • New kitchen • New hvac

NEW 26 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Winchester, VA:
Charming duplex priced ready to sell! Both sides renovated in 2026 as tenants have moved out, incredibly strong demand for more affordable rentals in this area. Both sides offer 2 bedrooms upstairs and 1 bathroom downstairs with kitchen, living room and separate back yards which tenants appreciate. Unit 7 is ready to tour - Unit 5 will be ready October 30th. Both units have similar floor plans. Seller offering potential discounted pricing if offer is made on both this property and 9 & 11 next door!

$310,000

4 beds2 baths1,260 sq ft

5 E Pall Mall St, Winchester, VA 22601

Renovated in 2026 • Separate back yards • 1,830 sq ft lot

(678) 894-9744

Property at 322 Highland Ave, Winchester, VA 22601, 4 beds, 2.5 baths

$269,900

4 beds2.5 baths1,484 sq ft

322 Highland Ave, Winchester, VA 22601

(866) 825-7169

Property at 2926 Sorrell Ct, Winchester, VA 22601, 3 beds, 1.5 baths

$279,900

3 beds1.5 baths1,251 sq ft

2926 Sorrell Ct, Winchester, VA 22601

(866) 825-7169

Property at 411 Mosby St, Winchester, VA 22601, 3 beds, 1 bath

$439,900

3 beds1 bath1,247 sq ft

411 Mosby St, Winchester, VA 22601

(540) 665-0360

Property at 1013 Orchard Hill Dr, Winchester, VA 22601, 3 beds, 1.5 baths

$299,900

3 beds1.5 baths1,648 sq ft

1013 Orchard Hill Dr, Winchester, VA 22601

(540) 773-8475

Property at 329 Fairview Ave, Winchester, VA 22601, 3 beds, 2 baths

$247,000

3 beds2 baths1,386 sq ft

329 Fairview Ave, Winchester, VA 22601

(480) 462-5392

Property at 317 S Kent St, Winchester, VA 22601, 4 beds, 1.5 baths

$399,000

4 beds1.5 baths1,800 sq ft

317 S Kent St, Winchester, VA 22601

(540) 773-8475

Property at 9 & 11 E Pall Mall St, Winchester, VA 22601, 4 beds, 2 baths

$340,000

4 beds2 baths1,612 sq ft

9 & 11 E Pall Mall St, Winchester, VA 22601

(678) 894-9744

Property at 103 E Germain St, Winchester, VA 22601, 2 beds, 1.5 baths

$240,000

2 beds1.5 baths1,068 sq ft

103 E Germain St, Winchester, VA 22601

(540) 686-7362

Property at 3 S Euclid Ave, Winchester, VA 22601, 3 beds, 2 baths

$305,500

3 beds2 baths1,350 sq ft

3 S Euclid Ave, Winchester, VA 22601

(703) 625-4269

Property at 1 E Hart St, Winchester, VA 22601, 4 beds, 2.5 baths

$299,900

4 beds2.5 baths1,680 sq ft

1 E Hart St, Winchester, VA 22601

(540) 773-8475

Property at 2919 S Pleasant Valley Rd, Winchester, VA 22601, 3 beds, 2 baths

$320,000

3 beds2 baths1,387 sq ft

2919 S Pleasant Valley Rd, Winchester, VA 22601

(571) 313-5831

Property at 23 Jigsaw Pl, Winchester, VA 22601, 2 beds, 1.5 baths

$229,000

2 beds1.5 baths1,160 sq ft

23 Jigsaw Pl, Winchester, VA 22601

(703) 445-9100

Property at 2660 Daniel Ter, Winchester, VA 22601, 2 beds, 1.5 baths

$335,000

2 beds1.5 baths1,352 sq ft

2660 Daniel Ter, Winchester, VA 22601

(540) 450-2747

Property at 116 E Cork St, Winchester, VA 22601, 2 beds, 1 bath

$389,000

2 beds1 bath1,216 sq ft

116 E Cork St, Winchester, VA 22601

(703) 669-0099

Property at 1008 S Cameron St, Winchester, VA 22601, 4 beds, 1.5 baths

$350,000

4 beds1.5 baths1,588 sq ft

1008 S Cameron St, Winchester, VA 22601

Property at 1847 Melvor Ln, Winchester, VA 22601, 2 beds, 2 baths

$339,900

2 beds2 baths1,234 sq ft

1847 Melvor Ln, Winchester, VA 22601

(540) 259-4090

Property at 501 Fox Dr, Winchester, VA 22601, 4 beds, 2 baths

$450,000

4 beds2 baths2,493 sq ft

501 Fox Dr, Winchester, VA 22601

(540) 662-9937

Property at 621 Watson Ave, Winchester, VA 22601, 3 beds, 1.5 baths

$285,000

3 beds1.5 baths1,138 sq ft

621 Watson Ave, Winchester, VA 22601

(703) 378-8810

Property at 5 E Hart St, Winchester, VA 22601, 2 beds, 2.5 baths

$284,900

2 beds2.5 baths1,540 sq ft

5 E Hart St, Winchester, VA 22601

(540) 773-8475

Property at 812 Appleseed Ct, Winchester, VA 22601, 3 beds, 1.5 baths

$359,000

3 beds1.5 baths1,710 sq ft

812 Appleseed Ct, Winchester, VA 22601

(540) 931-0144

Property at 2519 Hockman Ave, Winchester, VA 22601, 2 beds, 2 baths

$299,900

2 beds2 baths800 sq ft

2519 Hockman Ave, Winchester, VA 22601

(540) 450-0142

Property at 1048 Woodland Ave, Winchester, VA 22601, 3 beds, 1.5 baths

$320,000

3 beds1.5 baths1,507 sq ft

1048 Woodland Ave, Winchester, VA 22601

(540) 686-7362

Property at 310 Bellview Ave, Winchester, VA 22601, 2 beds, 1 bath

$300,000

2 beds1 bath1,097 sq ft

310 Bellview Ave, Winchester, VA 22601

(703) 669-0099

Property at 313 Avon Ct, Winchester, VA 22601, 2 beds, 1.5 baths

$177,000

2 beds1.5 baths896 sq ft

313 Avon Ct, Winchester, VA 22601

(703) 901-3400

Property at 805 S Kent St, Winchester, VA 22601, 4 beds, 2 baths

$325,000

4 beds2 baths1,592 sq ft

805 S Kent St, Winchester, VA 22601

(703) 264-0000

Property at 2817 Papermill Rd, Winchester, VA 22601, 3 beds, 1.5 baths

$325,000

3 beds1.5 baths1,248 sq ft

2817 Papermill Rd, Winchester, VA 22601

(703) 726-3909

Property at 1125 Conway St, Winchester, VA 22601, 2 beds, 1 bath

$250,000

2 beds1 bath870 sq ft

1125 Conway St, Winchester, VA 22601

(540) 667-9097

Property at 1314 S Braddock St, Winchester, VA 22601, 3 beds, 1 bath

$270,000

3 beds1 bath960 sq ft

1314 S Braddock St, Winchester, VA 22601

(480) 462-5392

Property at 519 Virginia Ave, Winchester, VA 22601, 3 beds, 1.5 baths

$274,000

3 beds1.5 baths1,161 sq ft

519 Virginia Ave, Winchester, VA 22601

(540) 662-0323

Property at 115 S Purcell Ave, Winchester, VA 22601, 3 beds, 3 baths

$280,000

3 beds3 baths1,281 sq ft

115 S Purcell Ave, Winchester, VA 22601

(540) 450-2747

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

$376,990

3 beds3.5 baths1,806 sq ft

Monteith Dr #3, Winchester, VA 22601

Listing provided by Zillow

Property at 1853 Rosser Ln, Winchester, VA 22601, 2 beds, 2 baths

$385,000

2 beds2 baths1,186 sq ft

1853 Rosser Ln, Winchester, VA 22601

(540) 931-0144

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

$376,990

3 beds3.5 baths1,806 sq ft

HOMESITE 3 Monteith Dr, Winchester, VA 22601

(240) 457-9391

Property at 305 Smalts Cir, Winchester, VA 22601, 3 beds, 2.5 baths

$329,990

3 beds2.5 baths1,576 sq ft

305 Smalts Cir, Winchester, VA 22601

Listing provided by Zillow

Property at 413 Superior Ave, Winchester, VA 22601, 3 beds, 2 baths

$425,000

3 beds2 baths2,030 sq ft

413 Superior Ave, Winchester, VA 22601

(540) 348-4911

Property at 229 Monteith Dr, Winchester, VA 22601, 3 beds, 3.5 baths

$369,990

3 beds3.5 baths1,756 sq ft

229 Monteith Dr, Winchester, VA 22601

(240) 457-9391

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Cheap Homes for Sale in Winchester

There are currently 86 cheap homes for sale in Winchester at a median listing price of $385K. 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 1 offers. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 26 homes have been sold in Winchester. In addition to houses in Winchester, there were also 2 condos, 28 townhouses, and 6 multi-family units for sale in Winchester last month. 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. 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.

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