The Appeal

Cherry Grove and Winding Way represent the best of established Hendersonville — neighborhoods where mature oak and maple trees arch over quiet streets, lots are generously sized, and homes have the kind of character that only comes with time. These are the neighborhoods that longtime Hendersonville residents point to when they talk about the city's charm.

What Cherry Grove and Winding Way lack in HOA amenities, they more than make up for in space, privacy, and value. Lot sizes commonly range from 0.3 to 0.5 acres — significantly larger than what you'll find in newer master-planned communities. Mature trees provide natural shade and privacy that no amount of newly planted landscaping can replicate. And the absence of HOA fees (in most sections) means lower monthly carrying costs.

Home Styles

These neighborhoods offer an eclectic mix of traditional brick ranches, two-story colonials, modern farmhouse remodels, and the occasional new construction infill. The variety means buyers can often find a home with character and bones that can be updated over time, rather than a cookie-cutter new build. This also means values can vary significantly from street to street — a home that's been tastefully renovated can command $100K+ more than an original-condition comp.

What to Know

• Most sections have no HOA — keep your boat, RV, or workshop without restriction (check deed restrictions on your specific property)
• School zoning varies by specific address; Jeff can verify exact school assignments for any property you're considering
• Older homes may need updates — budget for HVAC, roof, and cosmetic renovations if buying original-condition
• The mature tree canopy is beautiful but requires maintenance — factor in arborist costs for large trees near structures
• Location is central: 5 minutes to Indian Lake shopping, 5 minutes to Drakes Creek Park, 25 minutes to Nashville
• These neighborhoods rarely have multiple homes for sale simultaneously — inventory is naturally low due to high owner satisfaction