Pittsboro, NC Homes

• 

  

  

  /79

  $990,000

  Pending

  • 4 Beds
  • 4 Baths
  • 3,109 Sq Ft

  443 Valley Ln, Pittsboro, NC 27312

  Nestled in Monterrane, one of Chatham County's most coveted neighborhoods, this exceptional custom-built home blends timeless English cottage charm with warm, inviting living spaces designed for comfort and connection. Featuring 4 bedrooms, 2 full and 2 half baths, and situated on just under 3 private acres, this cedar shake-sided home with an architectural roof showcases quality construction and

  Katy McReynolds Chatham Homes Realty

  443 Valley Ln, Pittsboro, NC 27312
• 

  

  

  /66

  $935,000

  Sold Mar 02, 2026

  93 Bur Oak Ct, Pittsboro, NC 27312

  • 4 Beds
  • 4 Baths
  • 3,250 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $288/SF
  • 251 Days On Market

  Current Estimated Value $971,541

  Last Listing Agent Bradley Phelps Long & Foster Real Estate INC/Raleigh

  93 Bur Oak Ct, Pittsboro, NC 27312
• 

  

  

  /65

  Est $372,261

  Not Listed For Sale

  467 Red Coon Run Unit 467 & 551, Pittsboro, NC 27312

  • 6 Beds
  • 4 Baths
  • 1,979 Sq Ft
  • Built 1993

  467 Red Coon Run Unit 467 & 551, Pittsboro, NC 27312

  Last Sold Summary

  • 121 Days On Market

  Last Listing Agent Bonnie Strowd NorthGroup Real Estate, Inc.
• 

  

  

  /27

  $485,000

  $90K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,021 Sq Ft

  39 Banning Dr, Pittsboro, NC 27312

  Like new, 3-bedroom, 2.5-bath home, upscale living with high-end finishes at every turn. Located in the heart of sought-after Chatham Park, Vineyards collection. Walk to amenities, pool, playground plus much more! The open-concept main level is a showstopper, featuring gleaming hardwoods and a chef's kitchen anchored by an oversized marble island and a premium gas range. The living room exudes

  Devin G Home Team Realty Robbins and Associates Realty

  39 Banning Dr, Pittsboro, NC 27312
• 

  

  /2

  $736,067

  Sold Jul 13, 2026

  13 Englehart Ct, Fearrington, NC 27312

  • 3 Beds
  • 3 Baths
  • 2,452 Sq Ft
  • Built 2026

  Last Sold Summary

  • $300/SF
  • 0 Days On Market

  Last Listing Agent Erin Messier Weekley Homes, LLC

  13 Englehart Ct, Fearrington, NC 27312
• 

  

  /18

  Not Listed For Sale

  257 Circle City Way, Pittsboro, NC 27312

  • 4 Beds
  • 3.5 Baths
  • 3,037 Sq Ft
  • Built 2024

  257 Circle City Way, Pittsboro, NC 27312

  Last Sold Summary

  • 178 Days On Market

  Last Listing Agent Alex Lilly Pulte Home Company LLC
• 

  

  /36

  $610,000

  • 3 Beds
  • 2 Baths
  • 2,106 Sq Ft

  1396 Bynum Ridge Rd, Pittsboro, NC 27312

  Welcome to your own private retreat! Nestled on approximately 8 wooded acres between Pittsboro and Chapel Hill, this charming rustic home offers the perfect blend of privacy, comfort, and country living. An inviting front deck welcomes you into an open foyer and spacious family room featuring a stunning cathedral ceiling with exposed wood ceiling and beams, creating a warm and inviting

  Paul Russell Coldwell Banker HPW

  1396 Bynum Ridge Rd, Pittsboro, NC 27312
• 

  

  /53

  $525,000

  Sold Jan 23, 2026

  1838 Alex Cockman Rd, Pittsboro, NC 27312

  • 3 Beds
  • 2.5 Baths
  • 2,301 Sq Ft
  • Built 1985

  Last Sold Summary

  • 5% Below List Price
  • $228/SF
  • 30 Days On Market

  Current Estimated Value $555,814

  Last Listing Agent Eric Andrews Realty World Carolina Prop

  1838 Alex Cockman Rd, Pittsboro, NC 27312
• 

  

  /18

  Not Listed For Sale

  247 Circle City Way, Pittsboro, NC 27312

  • 5 Beds
  • 4 Baths
  • 3,284 Sq Ft
  • Built 2024

  247 Circle City Way, Pittsboro, NC 27312

  Last Sold Summary

  • 129 Days On Market

  Last Listing Agent Alex Lilly Pulte Home Company LLC
• 

  

  /23

  $310,000

  $10K PRICE DROP

  • Land
  • 5.08 Acres
  • $61,000 per Acre

  334 Deer Run, Pittsboro, NC 27312

  Discover the perfect setting for your custom home in the wooded surroundings of Mount Gilead Woods. This rare 5-acre homesite offers a beautiful level landscape with mature hardwoods, partial clearing already completed, and over 700 feet of road frontage for exceptional privacy and flexibility. A new gravel drive and private gated entrance are already in place, creating an easy path to start

  Dennis de Jong Redfin Corporation

  334 Deer Run, Pittsboro, NC 27312
• 

  

  /34

  $600,000

  Sold Sep 10, 2025

  114 Bridle Path, Pittsboro, NC 27312

  • 5 Beds
  • 3 Baths
  • 3,354 Sq Ft
  • Built 2007

  Last Sold Summary

  • 5% Below List Price
  • $179/SF
  • 35 Days On Market

  Current Estimated Value $637,467

  Last Listing Agent Tlynthia Crews Tlynthia Crews

  114 Bridle Path, Pittsboro, NC 27312
• 

  

  /13

  Not Listed For Sale

  137 Highpointe Dr, Pittsboro, NC 27312

  • 4 Beds
  • 3 Baths
  • 2,762 Sq Ft
  • Built 2024

  137 Highpointe Dr, Pittsboro, NC 27312

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Alex Lilly Pulte Home Company LLC
• 

  

  /90

  $799,900

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,657 Sq Ft

  89 Lauren Ct, Pittsboro, NC 27312

  Every day is a vacation at this marvelous 4 bedroom 3 1/2 bath Chatham County home! Let's start with the outside: A 24' diameter pool, hot and cold water shower with changing room plus a water slide with custom surround decking and clubhouse anchors the backyard, a wooded setting perfect for big gatherings or just relaxing with the family. There's also a deck and patio near the grill, and all the

  Ken Tunnell Weaver Street Realty & Auction

  89 Lauren Ct, Pittsboro, NC 27312
• 

  

  /86

  $560,000

  Sold Nov 10, 2025

  329 Windsong Dr, Pittsboro, NC 27312

  • 4 Beds
  • 3 Baths
  • 2,904 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $193/SF
  • 39 Days On Market

  Current Estimated Value $569,147

  Last Listing Agent Catherine Hobbs Chatham Homes Realty

  329 Windsong Dr, Pittsboro, NC 27312
• 

  

  /51

  Est $806,701

  Not Listed For Sale

  66 N Holiday Dr, Pittsboro, NC 27312

  • 5 Beds
  • 4 Baths
  • 3,606 Sq Ft
  • Built 2023

  66 N Holiday Dr, Pittsboro, NC 27312

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Danni Napoli DRB Group North Carolina LLC
• 

  

  /40

  $550,000

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,999 Sq Ft

  402 N Village Pkwy, Pittsboro, NC 27312

  Welcome to 402 North Village Parkway in NoVi Chatham Park, a thoughtfully designed home offering comfort, style and versatility. This Atkinson B floor plan features 1,999 square feet of living space with three bedrooms, two and a half baths, a main level Owner's Retreat, a study and a two car garage. The open layout connects the family room, dining area and kitchen, creating a bright and inviting

  David Weekley Homes Builder

  402 N Village Pkwy, Pittsboro, NC 27312
• 

  /2

  $463,900

  Sold Sep 05, 2025

  70 Tantara Bend, Pittsboro, NC 27312

  • 2 Beds
  • 2 Baths
  • 1,469 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $316/SF
  • 13 Days On Market

  David Weekley Homes Encore at Chatham Park - Villa Series

  70 Tantara Bend, Pittsboro, NC 27312
• 

  

  /11

  Est $246,978

  Not Listed For Sale

  961 Hamlets Chapel Rd, Pittsboro, NC 27312

  • 3 Beds
  • 1 Bath
  • 866 Sq Ft
  • Built 1962

  961 Hamlets Chapel Rd, Pittsboro, NC 27312

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Tabitha Elien Berkshire Hathaway HomeService
• 

  

  /50

  $399,990

  New Construction $69K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,724 Sq Ft

  56 Wandering Way, Pittsboro, NC 27312

  Corner homesite. More windows. More natural light. More privacy. Welcome to 56 Wandering Way, where thoughtful design meets one of the Triangle's most exciting master planned communities. This move in ready Sampson townhome offers an open concept layout filled with natural light, creating a home that feels bright, spacious, and inviting from the moment you walk in. The gourmet kitchen features

  Gabriell Taylor Tri Pointe Homes Inc

  56 Wandering Way, Pittsboro, NC 27312
• 

  

  /59

  $875,000

  Sold Oct 30, 2025

  109 Henrys Ridge Rd, Pittsboro, NC 27312

  • 4 Beds
  • 3.5 Baths
  • 3,357 Sq Ft
  • Built 2016

  Last Sold Summary

  • 3% Below List Price
  • $261/SF
  • 65 Days On Market

  Current Estimated Value $923,072

  Last Listing Agent Cara Pierce Compass -- Raleigh

  109 Henrys Ridge Rd, Pittsboro, NC 27312
• 

  

  /32

  Est $428,646

  Not Listed For Sale

  577 Woodbury, Pittsboro, NC 27312

  • 3 Beds
  • 2.5 Baths
  • 2,270 Sq Ft
  • Built 1991

  577 Woodbury, Pittsboro, NC 27312

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Cappy Hagman Coldwell Banker - HPW
• 

  

  /83

  $1,150,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,730 Sq Ft

  148 Tobacco Rd, Pittsboro, NC 27312

  Tucked away on almost two private acres with room for a pool, this custom designed Craftsman estate blends timeless architecture with refined luxury. The MAIN FLOOR PRIMARY SUITE with vaulted ceilings, his & her walk-in closets and spa bath make for a wonderful retreat. Also on the MAIN FLOOR is an IN-LAW/GUEST SUITE with it's own spa bath, living area, kitchen and private entrance. The open

  Kathy Shaw Keller Williams Elite Realty

  148 Tobacco Rd, Pittsboro, NC 27312
• 

  

  /96

  $1,575,000

  Sold Mar 30, 2026

  243 Sunset Grove Dr, Pittsboro, NC 27312

  • 4 Beds
  • 4.5 Baths
  • 3,563 Sq Ft
  • Built 2018

  Last Sold Summary

  • 15% Above List Price
  • $442/SF
  • 2 Days On Market

  Current Estimated Value $1,575,086

  Last Listing Agent Chanel D'Aprix LPT Realty, LLC

  243 Sunset Grove Dr, Pittsboro, NC 27312
• 

  

  /57

  Est $729,362

  Not Listed For Sale

  289 Stoneview, Pittsboro, NC 27312

  • 2 Beds
  • 2 Baths
  • 2,260 Sq Ft
  • Built 2016

  289 Stoneview, Pittsboro, NC 27312

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Bonnie Strowd NorthGroup Real Estate, Inc.
• 

  

  /16

  $2,500,000

  New Construction Pending

  • 5 Beds
  • 5.5 Baths
  • 5,251 Sq Ft

  410 Firefly Overlook, Pittsboro, NC 27312

  PRESALE NEW CONSTRUCTION: This is your opportunity to build this plan or work with the builder, Hurst Home Company, to build your own plan. Located in Firefly Overlook at Jordan Lake, a new custom home community that consists of 30 acreage homesites, situated in the midst of natural beauty and in walking distance to Jordan Lake. Homesite 26 has an overlooking view of the community, with 1.55

  Johnathan Stroud The Real Estate Company

  410 Firefly Overlook, Pittsboro, NC 27312
• 

  

  /86

  $1,575,000

  Sold Dec 01, 2025

  170 Kenwood Ln, Pittsboro, NC 27312

  • 4 Beds
  • 3.5 Baths
  • 4,103 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Above List Price
  • $384/SF
  • 2 Days On Market

  Current Estimated Value $1,632,249

  Last Listing Agent Brooke Gelhaus Compass -- Chapel Hill - Durham

  170 Kenwood Ln, Pittsboro, NC 27312
• 

  

  /33

  Est $601,894

  Not Listed For Sale

  856 Millcroft, Pittsboro, NC 27312

  • 2 Beds
  • 2 Baths
  • 2,057 Sq Ft
  • Built 2004

  856 Millcroft, Pittsboro, NC 27312

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Lee Waters Waters Real Estate Brokerage
• 

  

  /16

  $227,000

  $53K PRICE DROP

  • Land
  • 5.01 Acres
  • $45,309 per Acre

  100 Rolling Acres, Pittsboro, NC 27312

  Do not miss the opportunity to own approximately 5 acres of land in Pittsboro. The property includes an existing mobile home structure that has not been occupied in over 15 years and is not considered livable. The home is being conveyed at no value. The property is equipped with a well and septic system; however, the seller makes no representations or guarantees regarding their condition or

  Bobbie Boghosian RE/MAX One Hundred

  100 Rolling Acres, Pittsboro, NC 27312
• 

  

  /37

  $1,960,000

  Sold Aug 06, 2026

  1601 Montvale Grant Way, Pittsboro, NC 27312

  • 5 Beds
  • 5.5 Baths
  • 4,117 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Above List Price
  • $476/SF
  • 5 Days On Market

  Last Listing Agent Michelle Roberts Keller Williams Legacy

  1601 Montvale Grant Way, Pittsboro, NC 27312
• 

  

  /45

  Est $709,653

  Not Listed For Sale

  10 E Madison, Pittsboro, NC 27312

  • 3 Beds
  • 2.5 Baths
  • 2,731 Sq Ft
  • Built 1993

  10 E Madison, Pittsboro, NC 27312

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Bonnie Strowd NorthGroup Real Estate, Inc.
• 

  

  /26

  Price To Be Determined

  New Construction

  • 2 - 3 Beds
  • 2.5 - 3.5 Baths
  • 2,179 Sq Ft

  Stardom Plan at Del Webb at Chatham Park - Echelon, Pittsboro, NC 27312

  Feel the impact of the Stardom with a home that is open, bright, and designed to impress. Natural light fills the gathering space, drawing you toward the covered patio where indoor and outdoor living come together. At the center, an expansive kitchen creates the perfect place to connect, while the owner's suite offers a relaxing retreat at the end of the day.

  Del Webb Builder

  1377 Sanford St Unit 41298654, Pittsboro, NC 27312
• 

  

  /34

  $395,000

  Sold Jun 09, 2026

  40 Broadoak Ln, Pittsboro, NC 27312

  • 3 Beds
  • 3 Baths
  • 1,864 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 14% Below List Price
  • $212/SF
  • 69 Days On Market

  Current Estimated Value $477,000

  Homes By Dickerson NoVi Chatham Park - Elements Collection

  40 Broadoak Ln, Pittsboro, NC 27312
• 

  

  /73

  Est $1,186,154

  Not Listed For Sale

  292 Stoneview, Pittsboro, NC 27312

  • 5 Beds
  • 5 Baths
  • 4,623 Sq Ft
  • Built 2003

  292 Stoneview, Pittsboro, NC 27312

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Chanel D'Aprix LPT Realty, LLC
• 

  

  /36

  $466,980

  New Construction Pending

  • 2 Beds
  • 2 Baths
  • 1,469 Sq Ft

  156 Tantara Bend, Pittsboro, NC 27312

  Welcome to The Ambition, a beautifully designed paired villa in sought-after Encore at Chatham Park, offering elegant one-level living with upscale finishes and abundant natural light. A private front courtyard welcomes you into the open-concept layout featuring a gourmet kitchen with gas cooktop, built-in wall oven, oversized island, and walk-in pantry. The spacious family and dining areas are

  Tracey Riordan Weekley Homes, LLC

  156 Tantara Bend, Pittsboro, NC 27312
• 

  

  /15

  $552,300

  Sold Aug 26, 2025

  252 Beacon Dr, Pittsboro, NC 27312

  • 3 Beds
  • 2.5 Baths
  • 2,054 Sq Ft
  • Built 2025

  Last Sold Summary

  • 17% Above List Price
  • $269/SF
  • 90 Days On Market

  Last Listing Agent Jessie Krieger EXP Realty LLC

  252 Beacon Dr, Pittsboro, NC 27312
• 

  

  /28

  Est $634,399

  Not Listed For Sale

  34 Karlie Ct, Pittsboro, NC 27312

  • 4 Beds
  • 3 Baths
  • 3,156 Sq Ft
  • Built 2019

  34 Karlie Ct, Pittsboro, NC 27312

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Brianna Lane Costello Real Estate & Investm
• 

  

  /17

  $260,000

  $15K PRICE DROP

  • Land
  • 8.36 Acres
  • $31,100 per Acre

  177 Karen Calhoun Rd, Pittsboro, NC 27312

  Secluded & private homesite - minutes from town! Tucked away off a quiet road, this unrestricted vacant land backs up to Pokeberry Creek and offers the perfect setting for your dream home or private retreat. Surrounded by mature vegetation, the property provides exceptional privacy and seclusion - yet remains just a short drive to downtown Pittsboro, Chatham Park, Chapel Hill, Apex, Cary, RTP,

  Eric Andrews Realty World Carolina Prop

  177 Karen Calhoun Rd, Pittsboro, NC 27312
• 

  

  /71

  $950,000

  Sold Jul 06, 2026

  701 Spindlewood, Pittsboro, NC 27312

  • 4 Beds
  • 6 Baths
  • 5,417 Sq Ft
  • Built 2002

  Last Sold Summary

  • 13% Below List Price
  • $175/SF
  • 107 Days On Market

  Current Estimated Value $1,044,461

  Last Listing Agent Brigitte Condoret Century 21 Southern Lifestyles

  701 Spindlewood, Pittsboro, NC 27312
• 

  

  /22

  Est $640,930

  Not Listed For Sale

  103 Highpointe Dr, Pittsboro, NC 27312

  • 5 Beds
  • 4 Baths
  • 2,744 Sq Ft
  • Built 2024

  103 Highpointe Dr, Pittsboro, NC 27312

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Alex Lilly Pulte Home Company LLC
• 

  

  /9

  $10,750,000

  • Land
  • 43.18 Acres
  • $248,981 per Acre

  TBD US 15 501 Hwy N, Pittsboro, NC 27312

  Seller will consider a long-term ground lease. Don't miss out on this 43-acre parcel with unlimited potential. It's located on the corner of 15-501 and Hamlets Chapel creating exceptional access to the highway which makes traveling to Pittsboro or Chapel Hill easy. There are several developments being constructed up and down Hamlets Chapel proving that this location is highly desirable. Being a

  Riz Siddiqui Riz Realty LLC

  TBD US 15 501 Hwy N, Pittsboro, NC 27312

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