Chestnut Bend

FRANKLIN’S WALKABLE LUXURY COMMUNITY

Location and Daily Life in Chestnut Bend

Chestnut Bend sits off Hillsboro Road in Franklin, Tennessee, making it one of the most walkable luxury neighborhoods in Williamson County. In a market where walkability is usually a tradeoff against lot size or square footage, Chestnut Bend manages to deliver both. Residents can walk to historic downtown Franklin in about 15 minutes, reach Harlinsdale Farm in 5 minutes on foot, and access Franklin High School the same way.

The neighborhood connects directly to Franklin’s trail system through a back gate, putting The Factory at Franklin, the Franklin Farmers Market, Bicentennial Park, and the pedestrian bridge over the Harpeth River within easy reach on foot or by bike. This is not a stretch claim for marketing purposes. Multiple sellers in the neighborhood have specifically called out this access in their listing descriptions because buyers keep asking about it.

Hillsboro Road provides quick access to I-65 and Cool Springs, but the neighborhood itself feels removed from the corridor’s commercial activity. Streets like Walden Drive, Harrow Lane, Ploughman’s Bend Drive, and Prairie View Drive are shaded by mature trees and designed to move slowly. Chestnut Bend was developed in phases through the late 1990s and early 2000s, which means the landscaping has had 20-plus years to mature.

Daily errands are handled easily via the Cool Springs area to the east or the Mack Hatcher Parkway corridor. The new H.G. Hill grocery and the Whole Foods on Columbia Avenue are within a short drive. For families prioritizing walkability, the Franklin High School location is a genuine everyday convenience.

The Homes

Chestnut Bend is an all-brick, established community built primarily between 1999 and 2002. Homes range from approximately 3,150 to over 5,500 square feet on lots averaging between 0.37 and 0.46 acres, which is notably generous for a neighborhood this close to downtown Franklin. The community includes multiple sections, with street names and lot configurations varying slightly by phase.

Architecture across the neighborhood leans traditional, with brick exteriors, side-entry garages (common in the later phases), covered front porches, and two-story layouts. Primary suites on the main floor appear in a meaningful percentage of the inventory. Interior features commonly include hardwood floors on main levels, gas fireplaces, granite or quartz countertops, formal dining rooms, and bonus rooms over the garage that owners have converted into offices, playrooms, or flex space.

Crawl space foundations are standard throughout the community. Most homes have 2- to 3-car garages. Lot sizes in the 0.37 to 0.46 acre range give most backyards room for decks, fenced yards, and significant landscaping without feeling cramped. Several homes include 3-car side-entry garages, which is uncommon at this price point in Franklin’s established neighborhoods.

Because the community is fully built out, every transaction is a resale. That means buyers are evaluating individual updates and conditions rather than standard builder finishes. Homes that have been updated in kitchens, baths, and primary suites are commanding the upper end of the price range. The 5,574 square foot home on Walden Drive that sold for $1,355,000 is a good example of what a larger, updated home on this street can achieve.

Chestnut Bend Market Data (Past 12 Months)

Data from RealTracs MLS. Rolling 12-month period.

Active Homes for Sale in Chestnut Bend

Recently Sold Homes in Chestnut Bend

Amenities

Chestnut Bend’s HOA maintains a full amenity package that is uncommon for a neighborhood built in the late 1990s era. The community has a pool, clubhouse, tennis courts, park, and walking trails, all maintained through quarterly dues of approximately $220, which annualizes to around $880 per year. For context, that’s a competitive rate for Franklin neighborhoods with this level of amenity infrastructure.

The walking trail network within the neighborhood connects to the broader Franklin trail system through the rear of the community. That connection gives residents access to Harlinsdale Farm, the pedestrian bridge, The Factory at Franklin, and downtown’s restaurant and retail district. This trail linkage is one of the features that most distinguishes Chestnut Bend from comparable price-tier neighborhoods that have pools but no meaningful connectivity to the rest of the city.

The clubhouse and pool area serve as a gathering point during summer months. Tennis courts are maintained as part of the HOA amenity package. The park area within the neighborhood provides green space for informal recreation. Underground utilities throughout most sections of the neighborhood eliminate overhead lines and contribute to the polished, established feel of the streetscape.

Schools Serving Chestnut Bend

Elementary: Johnson Elementary School serves Chestnut Bend. The school is part of Williamson County Schools, consistently ranked among the top school districts in Tennessee.

Middle: Freedom Intermediate School (grades 5-6) and Freedom Middle School (grades 7-8) serve Chestnut Bend students. The combined intermediate and middle school structure is standard for this zone within Williamson County Schools.

High: Franklin High School serves Chestnut Bend, and the school is walkable from the neighborhood. This is a practical daily advantage for families with high school students, since the walk from the neighborhood to the school does not require crossing any major roads.

Why Work with Nashville Home Guru?

Chestnut Bend is a fully built-out neighborhood with limited turnover, which makes knowing the data before you negotiate more important than in a higher-volume market. Over the past 12 months, Compass and Parks agents were involved in 1 of the 5 closed transactions in Chestnut Bend, representing 20% of sales activity. Statewide, Compass and Parks represent approximately 1 in 4 homes sold in Tennessee following the 2024 merger.

Patrick Higgins has completed more than 1,100 transactions totaling over $500 million in residential sales across Middle Tennessee. He has been named a RealTrends Top Tennessee Agent six consecutive times and leads the #1 ranked team in Nashville and #7 in Tennessee by the Wall Street Journal’s RealTrends report. That production level means he tracks this market every week, not just when a listing goes active.

For buyers in Chestnut Bend, the key advantage is knowing which floor plans command premium pricing, which streets and lot positions have the best trail access, and how individual updates translate to value at this price point. For sellers, positioning a home in the $1.1M to $1.4M range in Franklin requires specific comparative analysis against the broader 37064 luxury inventory, and that is exactly the kind of work Nashville Home Guru does before setting a price.

Compass is the #1 residential real estate brokerage in the United States by sales volume. That network gives Nashville Home Guru clients access to off-market opportunities, Compass Private Exclusive listings, and a referral pool that extends far beyond Middle Tennessee.

For sellers, the Compass 3-Phase Marketing Strategy delivers measurable results. Homes pre-marketed through Compass Private Exclusive and Coming Soon programs sell for 2.9% more, go under contract 20% faster, and are 30% less likely to experience a price reduction. Learn more about selling your home on your terms.

Nashville Home Guru is also a strong resource for sellers considering the Compass Concierge program, which covers pre-listing updates like flooring, paint, landscaping, and kitchen refreshes with no upfront costs or interest. In a neighborhood like Chestnut Bend, where buyers are comparing recently updated resales against each other, condition and presentation at the time of listing directly affect both speed and price. If you have questions about the best listing agent in Franklin or want to discuss your specific home’s positioning, Patrick is the right call.

Frequently Asked Questions About Chestnut Bend

What is the price range for homes in Chestnut Bend?

Based on the past 12 months of closed sales, homes in Chestnut Bend have sold between $1,150,000 and $1,355,000. The median sale price was $1,275,181. Price per square foot ranged from $239 to $391 depending on size, condition, and updates. There is currently one active listing priced at $1,200,000.

How walkable is Chestnut Bend to downtown Franklin?

Chestnut Bend is one of Franklin’s most walkable luxury neighborhoods. Downtown Franklin is approximately a 15-minute walk from most parts of the community. Harlinsdale Farm is about a 5-minute walk. The neighborhood connects to Franklin’s trail system through a rear gate, giving residents walking and biking access to The Factory at Franklin, Bicentennial Park, and the pedestrian bridge over the Harpeth River.

What are the HOA fees in Chestnut Bend?

HOA dues are approximately $220 per quarter, which equals roughly $880 per year. This covers maintenance of common areas and the community’s amenity package, which includes a pool, clubhouse, tennis courts, park, and walking trails.

What schools serve Chestnut Bend?

Chestnut Bend is zoned for Johnson Elementary School, Freedom Intermediate School (grades 5-6) and Freedom Middle School (grades 7-8), and Franklin High School. All are part of Williamson County Schools. Franklin High School is walkable from the neighborhood.

What amenities does Chestnut Bend have?

Chestnut Bend has a community pool, clubhouse, tennis courts, park, walking trails, and sidewalks throughout the neighborhood. The trail network connects to Franklin’s broader trail system. Most sections of the neighborhood also have underground utilities.

When was Chestnut Bend built?

Chestnut Bend was developed in multiple phases, with most homes built between 1999 and 2002. The community is fully built out with no new construction available. All transactions are resales.

How large are the homes and lots in Chestnut Bend?

Based on recent sales, homes range from approximately 3,150 to over 5,500 square feet. Lot sizes for closed sales have ranged from 0.37 to 0.46 acres. The community is all-brick with traditional architecture, and most homes have 2- to 3-car attached garages.

Who is the best real estate agent for Chestnut Bend in Franklin TN?

Patrick Higgins with Nashville Home Guru at Compass is one of the most experienced agents in the Chestnut Bend and Franklin 37064 market. With over 1,100 transactions and $500 million in Middle Tennessee residential sales, Patrick brings deep data expertise and Compass’s national marketing platform to every Chestnut Bend listing and buyer search. Call 615-682-1718 to discuss your goals.

Does Chestnut Bend have off-market or coming-soon listings?

Chestnut Bend is a desirable, low-turnover neighborhood, and some sellers choose to test the market quietly before going public. As a Compass agent, Patrick Higgins has access to Compass Private Exclusive listings and coming-soon opportunities that never appear on Zillow or Realtor.com. Contact Nashville Home Guru directly at 615-682-1718 to ask about current off-market availability.

Nearby Neighborhoods

If you’re exploring Chestnut Bend, these nearby Franklin communities may also be worth a look:

Brownstones, Downtown Franklin, Harpeth Meadows, Idlewood, Lockwood Glen, Magnolia Place, Rebel Meadows, Rizer Point, Rogersshire, Splendor Ridge, Stream Valley, Westfield

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