Winston-Salem's go-to neighborhood west of Buena Vista. Established in the 1950s, expanded through the '80s and '90s, and still one of the most consistently in-demand areas in the city. Strong schools and homes that actually have room for a family to live in them.
Sherwood Forest
27104
Sherwood Forest started as farmland on the western edge of Winston-Salem.
As the tobacco and textile businesses boomed and pushed residential development west past Ardmore and Buena Vista, Sherwood Forest was developed through the 1950s, 1960s, and 1970s as a solid, unpretentious neighborhood for working professionals and families building stable lives. At one point there was a local racetrack here. That era is long gone — but the character of the neighborhood (brick homes on real lots, neighbors who know each other, and a pool at the center of summer) has held.
The name distinction matters locally. What most people call Sherwood Forest is now referred to as Old Sherwood Forest — the original development, homes built between the 1950s and 1970s, predominantly brick single-story ranch homes ranging from around 1,600 to 3,000-plus square feet with three to five bedrooms. Styles include Traditional, Mid-Century Modern, Tudor, Split-Level, and Contemporary — more variety than a single description captures. New Sherwood Forest refers to the developments built north of Peacehaven Road from the 1980s through the early 2010s, featuring brick Colonial Revival and Traditional homes with spacious lots, larger square footage, and a slightly more suburban feel than the older section.
Both sections share the same central amenity: Peacehaven Pool, Playground, and Tennis Courts at 420 Hearthside Drive — a community pool with a pavilion, tennis courts, and playground that has been the center of neighborhood summer life for decades. Membership is optional and runs a few hundred dollars annually.
Leinbach Park sits within the neighborhood with a nautical-themed playground and seasonal water feature. The Sherwood Parcourse, a paved exercise trail, runs through the area connecting to Shaffner Park. The private Forsyth Country Club is nearby for buyers who want that access. Robinhood Road handles most daily errands — The Fresh Market, Harris Teeter, Momo Ashi Café, River Birch Lodge, and additional retail all within easy reach. Silas Creek Parkway provides access to Wake Forest University and Novant Health Forsyth Medical Center. Downtown Winston-Salem is about 12 minutes on US-421.
Old Sherwood — the 1950s–1970s brick ranches — has the more established character and the longer community history. New Sherwood — Colonial Revivals and Traditionals from the 1980s–2010s — is slightly more suburban in feel with larger footprints and newer systems. Both share the same school zone and the same general community identity. Knowing which section you're in when you're comparing listings matters for understanding what you're getting.
It earns strong ratings and has been consistently one of the better-regarded public high schools in Forsyth County. Sherwood Forest Elementary and Thomas Jefferson Middle round out the pipeline. Confirm current boundary lines directly with Winston-Salem/Forsyth County Schools before buying based on school assignment.
Homes in Old Sherwood Forest have been going under contract in around 12–27 days depending on price and condition. Many receive multiple offers. If this is your neighborhood, pre-approval ready before you tour — you won't have time to get it together after you fall in love with a house.
If you wanted Sherwood Forest because you expected a more affordable option than Buena Vista, you may need to recalibrate. Ardmore (low $200,000s to mid-$400,000s), Washington Park (median around $315,000), and West End (median around $324,000) are all established neighborhoods with active community associations and genuine character at price points that work for the $200K–$500K buyer.
The best way to know if a neighborhood is right for you is to spend a Saturday morning in it. I'll meet you for coffee and we'll walk a few blocks.