About this home

Welcome to 342 Canyon Rd, a spacious and beautifully maintained home in the desirable Twin Lakes Overlook community on Winchester's east side close to Rt 7. Situated on a beautifully landscaped corner lot of nearly .40 acres where the schoolbus stop is at the front door, this impressive home offers over 4,264 finished square feet with a thoughtfully designed floor plan perfect for both everyday living and entertaining. The inviting great room features a stunning stone fireplace, while the gourmet kitchen boasts a large center island, abundant cabinetry, and a bright breakfast area. A private main-level office provides the ideal space for working from home or a quiet study. Upstairs, you'll find four generously sized bedrooms, two full bathrooms, dual staircases, and an additional hallway for added convenience. The oversized primary suite has been custom expanded to include a spacious sitting area, creating a true owner's retreat. The partially finished walk-out basement includes a full bedroom, full bath and a wide staircase leading to the backyard, offering excellent flexibility for a recreation room, guest space, home gym, or future finishing. Enjoy outdoor living on the rear deck overlooking mature landscaping that provides exceptional privacy, with seasonal lake views and a nearby walking path to the lake. Additional highlights include a side-loading garage, one of the largest floor plans in the neighborhood, and high-speed Glo Fiber Optic internet. Conveniently located near shopping, dining, schools, and major commuter routes, this exceptional home offers the perfect combination of space, comfort, and versatility. This property is under active video surveillance, all access codes are extremely confidential. Huge primary suite and bonus room/bedroom over garage. School bus stop is at the front door so kids can wait inside for the bus! Water oriented properties don't last long , so schedule your private showing today!

Facts and features

Schools

• Millbrook High School

  high · 9-12 · 1.9 mi

  4

• Admiral Richard E. Byrd Middle School

  middle · 6-8 · 4.3 mi

  5

• Greenwood Mill Elementary School

  elementary · K-5 · 0.7 mi

  4

• Keystone Christian Academy

  elementary · K-12 · 1.6 mi

• Redbud Run Elementary School

  elementary · K-5 · 1.9 mi

  2

• Northwestern Regional Educational Programs

  elementary · 3.5 mi

Price history

• Sep 14, 2026 · Price Changed$699,900
• Aug 19, 2026 · Price Changed$714,000
• Jul 17, 2026 · Listed$724,000
• Aug 24, 2022 · Listing Removed—
• Jul 23, 2022 · Price Changed$599,500
• Jul 3, 2022 · Listed$610,000
• May 31, 2006 · Sold$511,238

Tax history

• 2026$3,622 tax · $683,500 assessed
• 2025$3,280 tax · $683,500 assessed
• 2024$3,096 tax · $607,200 assessed
• 2023$3,096 tax · $607,200 assessed
• 2022$3,012 tax · $493,800 assessed
• 2021$3,012 tax · $493,800 assessed
• 2020$2,598 tax · $425,900 assessed
• 2019$2,597 tax · $425,900 assessed

Home value

$693,000

• Collateral Analytics$693,000
• Cotality$684,600
• Quantarium$705,589

Where it is