Pittsboro, NC Homes

• 

  

  

  /50

  $1,249,000

  $201K PRICE DROP Pending

  • 4 Beds
  • 4.5 Baths
  • 4,402 Sq Ft

  58 S Julip Ct, Pittsboro, NC 27312

  NEW PRICE — 1,249,000.00!!!! Recently reduced from $1,329,000, this stunning Craftsman retreat in Pennington at Jordan Lake offers nearly 2.5 private acres, over 4,400 sq ft, a resort-style pool, finished basement, and the lifestyle buyers dream about. Built in 2017, this 4BR/4.5BA home features hardwood floors, coffered ceilings, an open flowing layout, fireplace, and a first-floor primary suite

  

  Valerie Deloach

  Keller Williams Elite Realty

  58 S Julip Ct, Pittsboro, NC 27312
• Explore Pittsboro

• 

  

  

  /117

  Starting at $1,930

  Total Monthly Price

  • 1 - 2 Beds

  152 Market Chapel Rd, Pittsboro, NC 27312

  Just outside Raleigh, NC in the beautiful, wooded city of Pittsboro, our 55+ Apartment Community features 1 and 2 bedroom floor plans with upscale amenities so you can live the lifestyle you love. Relax in luxury with chef-inspired kitchens enhanced by granite countertops, vinyl wood flooring, in-unit washer and dryer, oversized closets, and private balconies. Inspiration is just outside your

  Inspire Briar Chapel - 55+ Active Adult Community

  

  152 Market Chapel Rd, Pittsboro, NC 27312
• 

  

  

  /37

  $630,000

  Sold May 29, 2026

  9 Matchwood, Pittsboro, NC 27312

  • 3 Beds
  • 3 Baths
  • 2,769 Sq Ft
  • Built 1976

  Last Sold Summary

  • 3% Below List Price
  • $228/SF
  • 3 Days On Market

  Current Estimated Value $629,559

  Last Listing Agent Tony Hall Berkshire Hathaway HomeService

  9 Matchwood, Pittsboro, NC 27312
• 

  

  

  /17

  Not Listed For Sale

  78 Delia Ln, Pittsboro, NC 27312

  • 2 Beds
  • 2 Baths
  • 1,497 Sq Ft
  • Built 2024

  78 Delia Ln, Pittsboro, NC 27312

  Last Sold Summary

  Last Listing Agent Lisa Skumpija Absolute Realty Company, LLC
• 

  

  

  /97

  $857,000

  • 3 Beds
  • 3 Baths
  • 2,065 Sq Ft

  205 Anolis, Pittsboro, NC 27312

  Rustically handsome and rich with character, 205 Anolis offers approximately 2,700 square feet of living space set on 12 remarkable acres in the Redbud community. Tucked at the end of a gravel road, the property unfolds into a beautiful mix of hardwood and pine forest, rolling pasture, and an intermittent stream that feeds into Temple Creek, a tributary of the Haw River. A vernal pool in the

  

  Catherine Hobbs

  Chatham Homes Realty

  205 Anolis, Pittsboro, NC 27312
• 

  

  /25

  $1,195 Per Month

  • 1 Bed
  • 1 Bath
  • 896 Sq Ft
  • Condo for Rent

  24 Rectory St Unit 82, Pittsboro, NC 27312

  Welcome to this cozy and charming 1-bedroom, 1-bathroom one-story attached home at 25 Creekside Unit 82! This cute and inviting space offers easy, single-level living with a comfortable layout perfect for relaxing or entertaining. A monthly utility fee of $50 covers trash, landscaping, and pest control services. Washer and dryer rental is available for $75 per month. This community offers

  

  Carla Sevilla

  Chanticleer Properties LLC

  24 Rectory St Unit 82, Pittsboro, NC 27312
• 

  

  /22

  $290,000

  Sold Sep 02, 2025

  81 Honeysuckle Dr, Pittsboro, NC 27312

  • 3 Beds
  • 2 Baths
  • 1,198 Sq Ft
  • Built 1990

  Last Sold Summary

  • 12% Below List Price
  • $242/SF
  • 84 Days On Market

  Current Estimated Value $309,881

  Last Listing Agent Lisa Skumpija Absolute Realty Company, LLC

  81 Honeysuckle Dr, Pittsboro, NC 27312
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  /6

  Not Listed For Sale

  7241 U S Highway 64, Pittsboro, NC 27312

  7241 U S Highway 64, Pittsboro, NC 27312

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Kris Howard Chatham Homes Realty
• 

  

  /34

  $925,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,065 Sq Ft

  115 Pheasant Ct, Pittsboro, NC 27312

  4 Bed | 3 Bath | Custom Home on 2 Private Acres with Pool Nestled on a private 2-acre cul-de-sac lot in Pittsboro, just 12 minutes from Carrboro, this beautifully crafted custom home offers the perfect blend of luxury, comfort, and privacy. Surrounded by mature trees and featuring a sparkling pool, the property provides a peaceful retreat while remaining conveniently close to shopping, dining,

  

  Sharon Evans

  EXP Realty LLC

  115 Pheasant Ct, Pittsboro, NC 27312
• 

  

  /51

  Starting at $1,305 Per Month

  • 1 - 3 Beds

  145 Retreat Dr, Pittsboro, NC 27312

  Welcome to Sanctuary at Powell Place, the ultimate destination for comfort living in Pittsboro, NC. Conveniently located with quick and easy access to Chapel Hill, Raleigh, and the entire Triangle area, our community is designed specifically for modern living. With state-of-the-art amenities and a prime location, Sanctuary at Powell Place is the perfect place to call home.As a

  Sanctuary at Powell Place

  

  145 Retreat Dr, Pittsboro, NC 27312
• 

  

  /34

  $310,000

  Sold Feb 12, 2026

  25 Juleann Ln, Pittsboro, NC 27312

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1997

  Last Sold Summary

  • 11% Below List Price
  • $231/SF
  • 57 Days On Market

  Current Estimated Value $330,141

  Last Listing Agent Loci Zsuppan Zsuppan Realty

  25 Juleann Ln, Pittsboro, NC 27312
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  /72

  Not Listed For Sale

  128 Shadowbrook, Pittsboro, NC 27312

  • 3 Beds
  • 3 Baths
  • 2,099 Sq Ft
  • Built 1985

  128 Shadowbrook, Pittsboro, NC 27312

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Colleen Jelley, CSA, PSA Dwell Real Estate
• 

  

  /70

  $975,000

  $35K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,249 Sq Ft

  378 Crimson Way, Pittsboro, NC 27312

  Rare value in Chapel Ridge: 5 bedrooms, 4 baths, and 4,249 square feet on a private 1.78 acre homesite, priced well below the neighborhood average per square foot. The lot slopes back from the road into a canopy of mature hardwoods, providing secluded, natural shade that lowers summer cooling costs. Two professionally installed French drains manage water flow across the property, so the natural

  

  Don Anthony Gomez

  C-A-RE Realty

  378 Crimson Way, Pittsboro, NC 27312
• 

  

  /22

  $2,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,850 Sq Ft
  • Townhouse for Rent

  531 Weathersfield, Pittsboro, NC 27312

  1 story end unit TH in Fearrington Village. 2 BR/2 Bath beautifully kept with gorgeous hardwood flooring, soaring ceilings and built in bookshelves covering one wall. FR features FP w/Gas Logs and a wall of windows overlooking the beautiful treed lot. 2 ample size bedrooms and two full baths compliment the great flow to the floor plan. Home has a beautiful sunroom, nice pantry and fantastic sized

  

  Terri McCall

  Chatham Homes Realty

  531 Weathersfield, Pittsboro, NC 27312
• 

  

  /33

  $489,900

  Sold Mar 13, 2026

  32 Relaxing Way, Pittsboro, NC 27312

  • 3 Beds
  • 2.5 Baths
  • 1,883 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $260/SF
  • 40 Days On Market

  Current Estimated Value $483,736

  David Weekley Homes NoVi Chatham Park - The Mews Collection

  32 Relaxing Way, Pittsboro, NC 27312
• 

  

  /61

  Est $1,060,060

  Not Listed For Sale

  188 E Antebellum Dr, Pittsboro, NC 27312

  • 4 Beds
  • 3.5 Baths
  • 3,844 Sq Ft
  • Built 2021

  188 E Antebellum Dr, Pittsboro, NC 27312

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Anita Oxford Compass -- Raleigh
• 

  

  /34

  $495,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,571 Sq Ft

  200 Imagine Way, Pittsboro, NC 27312

  Skip the wait for new construction and settle right into this like-new ranch home in the highly desirable 55+ community of Encore at Chatham Park. Designed with comfort and convenience in mind, this thoughtfully planned home offers 2 bedrooms, 2 full baths, and a dedicated office/den that's perfect for working from home, pursuing hobbies, or accommodating overnight guests. The open-concept layout

  

  Vicki Diprofio

  DiProfio Homes

  200 Imagine Way, Pittsboro, NC 27312
• 

  

  /54

  Starting at $1,430 Per Month

  • 1 - 3 Beds

  80 Haven Creek Rd, Pittsboro, NC 27312

  Medley at Northwood Landing is a brand-new, pet-friendly apartment community for rent in Pittsboro, NC, located directly across from the gateway to Chatham Park in Pittsboro, NC. Residents enjoy walkable access to grocery stores, medical and veterinary care, dining, and entertainment. On-site amenities include a dog park, pet wash station, business center, collaborative workspaces, fitness

  Medley at Northwood Landing

  

  80 Haven Creek Rd, Pittsboro, NC 27312
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  /49

  $795,000

  Sold Oct 10, 2025

  197 Roads End, Pittsboro, NC 27312

  • 4 Beds
  • 3 Baths
  • 2,708 Sq Ft
  • Built 2011

  Last Sold Summary

  • 2% Above List Price
  • $294/SF
  • 3 Days On Market

  Current Estimated Value $805,398

  Last Listing Agent Tana Widdows Compass -- Chapel Hill - Durham

  197 Roads End, Pittsboro, NC 27312
• 

  

  /37

  Est $407,024

  Not Listed For Sale

  307 Millbrook Dr, Pittsboro, NC 27312

  • 3 Beds
  • 2 Baths
  • 1,661 Sq Ft
  • Built 2008

  307 Millbrook Dr, Pittsboro, NC 27312

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Trevor Smith NextHome RARE Properties
• 

  

  /28

  $375,000

  $25K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  166 Wintersage, Pittsboro, NC 27312

  3 Bed | 2 Bath | True Single-Level Living on a Private Wooded Lot Between Pittsboro & Chapel Hill Experience the ease of true single-level living in this light-filled home, ideally situated between Pittsboro and Chapel Hill in a desirable Village community. Designed with both comfort and accessibility in mind, the home features zero-step entry from the oversized two-car garage, allowing seamless

  

  Sharon Evans

  EXP Realty LLC

  166 Wintersage, Pittsboro, NC 27312
• 

  

  /25

  $1,295 Per Month

  • 1 Bed
  • 1 Bath
  • 719 Sq Ft
  • Condo for Rent

  120 Rectory St Unit 32, Pittsboro, NC 27312

  Welcome to this cozy and charming 1-bedroom, 1-bathroom one-story attached home at 25 Creekside Unit 32! This cute and inviting space offers easy, single-level living with a comfortable layout perfect for relaxing or entertaining. The home features a bright living area, functional kitchen, and well-sized bedrooms, making it a great fit for anyone looking for a comfortable place to call home. Its

  

  Carla Sevilla

  Chanticleer Properties LLC

  120 Rectory St Unit 32, Pittsboro, NC 27312
• 

  

  /62

  $550,000

  Sold Mar 26, 2026

  353 Windsong Dr, Pittsboro, NC 27312

  • 3 Beds
  • 2.5 Baths
  • 2,953 Sq Ft
  • Built 2010

  Last Sold Summary

  • 3% Below List Price
  • $186/SF
  • 31 Days On Market

  Current Estimated Value $565,076

  Last Listing Agent Chanel D'Aprix LPT Realty, LLC

  353 Windsong Dr, Pittsboro, NC 27312
• 

  

  /48

  Est $545,089

  Not Listed For Sale

  499 Chatham Forest Dr, Pittsboro, NC 27312

  • 3 Beds
  • 2 Baths
  • 2,025 Sq Ft
  • Built 2005

  499 Chatham Forest Dr, Pittsboro, NC 27312

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Jeri Pederson Berkshire Hathaway HomeService
• 

  

  /59

  $895,000

  $255K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,640 Sq Ft

  1390 Bradford Place, Pittsboro, NC 27312

  Unique, Fully Custom Fearrington Village ''Gem'' for Sale located in the charming Bradford Place neighborhood of Fearrington Village with ideal east-west exposure, lies this ideal ''Modern Farmhouse'' designed and appointed to fit the Fearrington Village ethos. Upgraded in 2022, the 3640 finished square foot home sits on a .5 acre lot with dense forest and a creek. There is a 1170 sq ft

  

  Jo Ann Gardner

  All About U Real Estate

  1390 Bradford Place, Pittsboro, NC 27312
• 

  

  /35

  Starting at $1,265 Per Month

  • Studio - 3 Beds

  135 Ballentrae Ct, Pittsboro, NC 27312

  Elegant and modern farmhouse chic await you at Knoll at Briar Chapel, the area's first apartment community of its kind. Explore our beautifully appointed studio, one-, two-, and three-bedroom layouts. Discover a variety of amenities that help you relax, recharge and re-connect. Experience an idyllic setting and a warm welcome. Come home to Knoll at Briar Chapel.

  Knoll at Briar Chapel

  

  135 Ballentrae Ct, Pittsboro, NC 27312
• 

  

  /54

  $615,000

  Sold Feb 27, 2026

  83 Autumn Chase, Pittsboro, NC 27312

  • 4 Beds
  • 3 Baths
  • 3,001 Sq Ft
  • Built 2007

  Last Sold Summary

  • $205/SF
  • 2 Days On Market

  Current Estimated Value $634,003

  Last Listing Agent Lori Golden Century 21 Southern Lifestyles

  83 Autumn Chase, Pittsboro, NC 27312
• 

  

  /51

  Est $666,315

  Not Listed For Sale

  457 Poplar Forest Ln, Pittsboro, NC 27312

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2004

  457 Poplar Forest Ln, Pittsboro, NC 27312

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Jan Butta Coldwell Banker - HPW
• 

  

  /7

  $750,000

  $100K PRICE INCREASE

  • Land
  • 2.97 Acres
  • $252,525 per Acre

  383 Westhampton Dr, Pittsboro, NC 27312

  This site is 2.974 Acres. County water, natural gas, fiber optics ready in place! Heavily Wooded. Also protected on one side with a 50 Vegetative Steam Buffer. Surpassing other luxury communities throughout Chatham, Orange, and Wake Counties. Home sites capable of accommodating some of the largest custom residences in the Triangle region, including the most sprawling ranch plans. Exceptional

  

  Rex Osborne

  Windjam Properties

  383 Westhampton Dr, Pittsboro, NC 27312
• 

  

  /20

  $16,582

  Total Monthly Price

  • 4 Beds
  • 4 Baths
  • 1,991 Sq Ft
  • Condo for Rent

  288 Stonewall Rd Unit SI ID1055518P, Pittsboro, NC 27312

  The advertised rate of $16,582/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  288 Stonewall Rd Unit SI ID1055518P, Pittsboro, NC 27312
• 

  

  /95

  $2,199,000

  Sold Jun 23, 2026

  37 Green Turtle Ln, Pittsboro, NC 27312

  • 5 Beds
  • 5.5 Baths
  • 5,253 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $419/SF
  • 82 Days On Market

  Current Estimated Value $2,318,000

  Last Listing Agent Johnathan Stroud The Real Estate Company

  37 Green Turtle Ln, Pittsboro, NC 27312
• 

  

  /53

  Est $514,261

  Not Listed For Sale

  106 Redbud, Pittsboro, NC 27312

  • 3 Beds
  • 2 Baths
  • 2,041 Sq Ft
  • Built 1996

  106 Redbud, Pittsboro, NC 27312

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Nate Howard Howard Group Real Estate LLC
• 

  

  /37

  $465,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,487 Sq Ft

  513 Swim and Croquet Rd, Pittsboro, NC 27312

  A peaceful woodland setting, updated interiors, and the ease of main-level living, this comforting 3-bedroom, 2.5-bath townhome is nestled in the desirable Weathersfield neighborhood of Fearrington Village. You'll enjoy approximately 2,500 square feet of thoughtfully designed living where timeless flow meets effortless comfort. The sought-after main-level primary suite provides a peaceful

  

  Dianne Gray

  Coldwell Banker - HPW

  513 Swim and Croquet Rd, Pittsboro, NC 27312
• 

  

  /20

  $3,956

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 495 Sq Ft
  • Condo for Rent

  288 Stonewall Rd Unit SI ID1055516P, Pittsboro, NC 27312

  The advertised rate of $3,957/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 2, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  288 Stonewall Rd Unit SI ID1055516P, Pittsboro, NC 27312
• 

  

  /77

  $1,740,000

  Sold Jun 17, 2026

  68 Harvest Ln, Pittsboro, NC 27312

  • 4 Beds
  • 3.5 Baths
  • 4,163 Sq Ft
  • Built 2023

  Last Sold Summary

  • 8% Below List Price
  • $418/SF
  • 41 Days On Market

  Current Estimated Value $1,775,871

  Last Listing Agent Gretchen Coley Compass -- Raleigh

  68 Harvest Ln, Pittsboro, NC 27312
• 

  

  /87

  Est $917,225

  Not Listed For Sale

  13 Crosswinds Estates Dr, Pittsboro, NC 27312

  • 3 Beds
  • 3.5 Baths
  • 3,773 Sq Ft
  • Built 1991

  13 Crosswinds Estates Dr, Pittsboro, NC 27312

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Tim Mock Coldwell Banker HPW
• 

  

  /11

  $424,900

  $50K PRICE DROP

  • Land
  • 10.86 Acres
  • $39,114 per Acre

  388 Talon Dr, Pittsboro, NC 27312

  Build Your Dream Home on Top of the Hill!!! Discover this beautiful 10+ acre wooded lot in the established, upscale community of Eagles Ridge. Perfectly situated, this property offers both privacy and convenience—just minutes from Jordan Lake, Pittsboro, and the exciting growth of Chatham Park. The lot features a picturesque rocky creek along the back boundary and a gentle slope, ideal for

  

  Donna Thomas

  Coldwell Banker HPW Pittsboro

  388 Talon Dr, Pittsboro, NC 27312
• 

  

  /43

  $2,795

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft
  • House for Rent

  316 Hillsboro St, Pittsboro, NC 27312

  Is being walking distance to all the shops and restaurants in downtown Pittsboro appealing to you? If so, you have to check out this newly renovated house that is only a couple hundred yards away from the heart of downtown. The kitchen has been completely redone with new cabinets, new island, new appliances, and new countertops. This pet friendly house has a large screened in

  316 Hillsboro St, Pittsboro, NC 27312
• 

  

  /38

  $549,000

  Sold Mar 25, 2026

  32 Freeman Dr, Pittsboro, NC 27312

  • 4 Beds
  • 3.5 Baths
  • 2,948 Sq Ft
  • Built 2013

  Last Sold Summary

  • $186/SF
  • 1 Day On Market

  Current Estimated Value $561,902

  Last Listing Agent Keisha Simpson Omni Realty Group

  32 Freeman Dr, Pittsboro, NC 27312
• 

  

  /41

  Est $863,100

  Not Listed For Sale

  123 Cottage Way, Pittsboro, NC 27312

  • 4 Beds
  • 4.5 Baths
  • 3,296 Sq Ft
  • Built 2022

  123 Cottage Way, Pittsboro, NC 27312

  Last Sold Summary

  • 286 Days On Market

  Last Listing Agent Ryan Ford Triangle Real Estate Journal

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