Set on 1.3 private acres in the established Peppertree community, 64 Winthrop offers a rare combination of space, privacy, and convenience, while being just minutes from some of the Triangle's most important destinations. You're close enough to stay connected, yet far enough away to truly unwind. Enjoy an easy commute to major hospitals, universities, Chatham Park, and RTP. ~20 minutes to UNC Hospital, ~35 minutes to Duke University Hospital, ~20 minutes to Chatham Hospital. Inside, the 2,320 sqft layout is designed for flexibility. With two separate living areas and a massive bonus room, you have options like a home office, gym, media room, play space, or all of the above. Whether you work from home, take calls after hours, or just want space to spread out, this home has something for everybody. Large rooms, 9-ft ceilings, and abundant natural light create a bright, welcoming feel throughout. Lucky for the new owner the big-ticket items are already done, including a BRAND NEW ROOF, updated kitchen, whole- house water filtration system, and fresh interior paint. Step outside, and the setting does the rest. A covered wrap-around porch, expansive back deck, fire pit, and wooded backdrop give you multiple ways to recharge. There is space for morning coffee, weekend BBQs, or a quiet evening after a long day. The flat, usable yard is perfect for play, pets, or gathering with friends, while still offering the privacy of a wooded lot. It feels removed, but you're still part of a neighborhood. A spacious two-car garage includes a built-in Tesla charger with plenty of room for a workshop. Located just 15 minutes from downtown Pittsboro and Chatham Park, you're positioned in one of the Triangle's fastest-growing areas, offering both immediate livability and long-term upside. Homes that offer this much land, flexibility, and proximity are hard to find. This one hits the mark.
For sale
Price cut: $25.1K (4/9)
$599,900
64 Winthrop Rd, Pittsboro, NC 27312
3beds
2,232sqft
Est.:
Single Family Residence, Residential
Built in 2004
1.31 Acres Lot
$594,100 Zestimate®
$269/sqft
$8/mo HOA
What's special
Covered wrap-around porchMassive bonus roomAbundant natural lightBuilt-in tesla chargerExpansive back deckSpacious two-car garageLarge rooms
- 57 days |
- 1,877 |
- 79 |
Likely to sell faster than
Zillow last checked: 7 hours ago
Listing updated: April 09, 2026 at 10:13pm
Listed by:
Cory Sherman 919-849-5592,
Keller Williams Elite Realty
Source: Doorify MLS,MLS#: 10146165
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Heating
- Electric, Forced Air, Heat Pump, Zoned
Cooling
- Central Air, Heat Pump, Zoned
Appliances
- Included: Dishwasher, Electric Range, Microwave, Oven, Stainless Steel Appliance(s), Washer/Dryer, Water Purifier Owned
Features
- Flooring: Carpet, Hardwood, Tile
- Basement: Crawl Space
Interior area
- Total structure area: 2,232
- Total interior livable area: 2,232 sqft
- Finished area above ground: 2,232
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage
- Attached garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Porch, Wrap Around
- Has view: Yes
Lot
- Size: 1.31 Acres
- Features: Back Yard, Front Yard, Garden, Hardwood Trees, Landscaped, Open Lot, Wooded
Details
- Parcel number: 0078369
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Transitional
- Property subtype: Single Family Residence, Residential
Materials
- Fiber Cement
- Roof: Shingle
Condition
- New construction: No
- Year built: 2004
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Community & HOA
Community
- Subdivision: Peppertree
HOA
- Has HOA: Yes
- Services included: Road Maintenance
- HOA fee: $100 annually
Location
- Region: Pittsboro
Financial & listing details
- Price per square foot: $269/sqft
- Tax assessed value: $314,676
- Annual tax amount: $4,108
- Date on market: 2/12/2026
Estimated market value
$594,100
$564,000 - $624,000
$2,607/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 4/9/2026 | Price change | $599,900-4%$269/sqft |
Source: | ||
| 2/12/2026 | Listed for sale | $625,000+2.5%$280/sqft |
Source: | ||
| 4/26/2022 | Sold | $610,000+23.2%$273/sqft |
Source: | ||
| 4/4/2022 | Contingent | $495,000$222/sqft |
Source: | ||
| 4/4/2022 | Listed for sale | $495,000+82%$222/sqft |
Source: | ||
| 10/19/2018 | Listing removed | $2,250$1/sqft |
Source: Fonville Morisey/Chapel Hill Sales Office #2197018 Report a problem | ||
| 6/9/2018 | Listed for rent | $2,250$1/sqft |
Source: Fonville Morisey/Chapel Hill Sales Office #2197018 Report a problem | ||
| 3/29/2017 | Listing removed | $2,250$1/sqft |
Source: Fonville Morisey/Chapel Hill Sales Office #2105286 Report a problem | ||
| 3/2/2017 | Listed for rent | $2,250$1/sqft |
Source: Fonville Morisey/Chapel Hill Sales Office #2105286 Report a problem | ||
| 6/9/2009 | Sold | $272,000-5.9%$122/sqft |
Source: Public Record Report a problem | ||
| 4/3/2009 | Price change | $289,000-3.7%$129/sqft |
Source: Listhub #1644288 Report a problem | ||
| 1/29/2009 | Listed for sale | $300,000+18.9%$134/sqft |
Source: Listhub #1644288 Report a problem | ||
| 10/21/2004 | Sold | $252,400$113/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $2,821 +10.3% | $314,676 |
| 2023 | $2,558 +3.8% | $314,676 |
| 2022 | $2,464 +1.3% | $314,676 |
| 2021 | $2,432 +14% | $314,676 +14.7% |
| 2020 | $2,134 +5.7% | $274,271 |
| 2019 | $2,019 -5.2% | $274,271 |
| 2017 | $2,130 | $274,271 +0.4% |
| 2016 | $2,130 -0.8% | $273,303 |
| 2015 | $2,148 | $273,303 |
| 2014 | -- | $273,303 |
| 2013 | -- | $273,303 |
| 2012 | -- | $273,303 |
| 2011 | -- | $273,303 |
| 2010 | -- | $273,303 |
| 2009 | -- | $273,303 +9.8% |
| 2008 | -- | $248,864 |
| 2007 | $1,758 +7.5% | $248,864 |
| 2005 | $1,635 | $248,864 |
Find assessor info on the county website
Monthly payment
Est. payment
$3,243/mo
Principal & interest
$2915
Property taxes
$320
HOA Fees
$8
More affordability tools
Climate risks
Neighborhood: 27312
Nearby schools
GreatSchools rating
- 7/10Perry W Harrison ElementaryGrades: PK-5Distance: 0.4 mi
- 4/10Margaret B. Pollard Middle SchoolGrades: 6-8Distance: 2.4 mi
- 8/10Northwood HighGrades: 9-12Distance: 4.1 mi
Schools provided by the listing agent
- Elementary: Chatham - Perry Harrison
- Middle: Chatham - Margaret B Pollard
- High: Chatham - Northwood
Source: Doorify MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 27312
- North Carolina
- Chatham County
- Pittsboro
- 27312
- 64 Winthrop Rd





