227 Windlestraw, Pittsboro, NC 27312
Property image
Property image
SOLD
NOV 24, 2025

227 Windlestraw
Pittsboro, NC 27312

  • 3 Beds
  • 2 Baths
  • 1,960 sqft

$532,500

Last Sold: Nov 24, 2025
3% below list $550K
$272/sqft
Est. Refi. Payment $3,091/mo*
Refinance Your Home

$532,500

Last Sold: Nov 24, 2025
3% below list $550K
$272/sqft
Est. Refi. Payment $3,091/mo*
Refinance Your Home
3 Beds
2 Baths
1,960 sqft

Home Value

Trulia Estimate
$522K
Since last month
Decreased$5K (-1%)
Since last year
Increased$12K (+2.4%)
Since last sale
Decreased$11K (-2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +98% in the last 10 years
MonthEstimated value
2026
August 2026$522K
July 2026$527K
June 2026$532K
May 2026$529K
April 2026$530K
March 2026$527K
February 2026$522K
January 2026$534K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
223 Windlestraw, Pittsboro, NC
0.06
Single-Family Home
$580,000
06/02/26
3
2
2,239
251 Fox Rdg, Pittsboro, NC
0.16
Single-Family Home
$581,000
04/24/26
3
2
2,146
260 Clover Thatch, Pittsboro, NC
0.13
Single-Family Home
$595,000
05/29/26
3
2
2,820
182 Hedgerow, Pittsboro, NC
0.22
Single-Family Home
$590,000
05/20/26
3
2
2,079
191 Weatherbend, Pittsboro, NC
0.18
Single-Family Home
$637,500
06/17/26
2
2
1,708
127 Creekwood, Pittsboro, NC
0.43
Single-Family Home
$645,000
12/15/25
3
2
2,047
40 McDowell, Pittsboro, NC
0.43
Single-Family Home
$592,000
03/18/26
3
2
2,253

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
266 Clover Thatch, Pittsboro, NC 27312
0.07
$456,000
3
2
1,474
Off Market
217 Summerwood, Pittsboro, NC 27312
0.08
$452,300
3
3
1,732
Off Market
223 Windlestraw, Pittsboro, NC 27312
0.06
$580,000
3
2
2,239
Recently Sold
270 Quail Run, Pittsboro, NC 27312
0.13
$519,000
3
2
1,825
Off Market
196 Weatherbend, Pittsboro, NC 27312
0.10
$452,200
3
2
1,675
Off Market
260 Clover Thatch, Pittsboro, NC 27312
0.13
$595,000
3
2
2,820
Recently Sold
199 Weatherbend, Pittsboro, NC 27312
0.14
$742,600
3
3
2,260
Off Market
210 Hollyhock, Pittsboro, NC 27312
0.18
$454,600
3
2
1,756
Off Market
243 Fox Rdg, Pittsboro, NC 27312
0.13
$461,300
2
2
1,353
Off Market
374 Wintercrest W, Pittsboro, NC 27312
0.17
$409,800
3
2
1,841
Off Market
252 Fox Rdg, Pittsboro, NC 27312
0.15
$366,500
2
2
2,002
Off Market

Local Information

  • Map ViewExplore the area around 227 Windlestraw.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1983
Living Area
1,960 sqft
Price/Sqft
$272/sqft
Parking
Garage
HOA
$25/Monthly

About this House

One-level contemporary home in the Fearrington Historic District! This home features an entry foyer that opens to a large living room with high ceilings, built-ins, a gas fireplace, and many windows with lovely, wooded views. There is a formal dining area plus a breakfast nook with a bay window in the kitchen. The spacious kitchen features an island and good counter and cabinet space. A laundry room with a freezer adjoins the kitchen. The primary bedroom has good closet space and a beautifully updated private bath with a tile shower. There are two additional bedrooms and another full bathroom. The sunroom has two walls with windows and a door that opens to a fenced area in the back yard. A covered walkway leads to the two-car garage with a storage room, workbench, skylight, and updated lighting. The covered front porch has phantom screen. Brick patio. Generator. Quiet, low-traffic cul-de-sac that is convenient to the village shops and swim club.
227 Windlestraw, Pittsboro, NC 27312 is a 3 bedroom, 2 bathroom, 1,960 sqft single-family home built in 1983. It last sold for $532,500 on Nov 24, 2025 (3% below the $550,000 asking price). It is currently off market. The Trulia Estimate is $521,700, with a rent estimate of $2,590/month.
Last check for updates: 1 day ago
Listed by Tony Hall, (919) 740-9611
Tony Hall & Associates
Bought with: Brigitte J Condoret, (404) 295-8980, Century 21 Southern Lifestyles
Source: Doorify MLS, MLS#10127366

Home Details for 227 Windlestraw

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 8
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1960 Square Feet
Appliances & Utilities
Appliances: Disposal, Dryer, Freezer, Gas Water Heater, Range Hood, Refrigerator, WasherDisposalDryerLaundry: Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: Electric, Forced Air, Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Fireplace & Spa
Number of Fireplaces: 1Fireplace: GasHas a Fireplace
Windows, Doors, Floors & Walls
Window: Bay Window(s), Skylight(s)Flooring: Carpet, Hardwood, Parquet, Tile, Vinyl
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Hardwood, Parquet, Tile, Vinyl
View
Has a View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Patio, PorchFencing: Back YardNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageNo Attached GarageParking Spaces: 2Parking: Detached,Driveway,Garage,Garage Faces Front,Workshop in Garage
Pool
Pool: Swimming Pool Com/Fee
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1960 Square Feet

Property Information

Year Built
Year Built: 1983
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialStructure Type: House, Site BuiltArchitecture: Contemporary
Building
Construction Materials: Masonite, Wood SidingNot a New Construction
Property Information
Parcel Number: 0019167

Price & Status

Price
List Price: $550,000Price Per Sqft: $272/sqft

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: PittsboroCommunity: Fearrington
School Information
Elementary School: Chatham - Perry HarrisonJr High / Middle School: Chatham - Margaret B PollardHigh School: Chatham - Seaforth

Building

Building Area
Building Area: 1960 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: NoneHas an HOAHOA Fee: $300/Annually

Listing Info

Special Conditions: Standard

Miscellaneous

Mls Number: 10127366Above Grade Unfinished Area: 1960

Price and Tax history

DateEventPrice
Nov 24, 2025
Source: Doorify MLS #10127366
Sold
$532,500
Oct 28, 2025
Source: Doorify MLS #10127366
Pending
$550,000
Oct 13, 2025
Source: Doorify MLS #10127366
Listed For Sale
$550,000
May 23, 2025
Source: Doorify MLS #10088938
Sold
$502,500
Apr 21, 2025
Source: Doorify MLS #10088938
Pending
$500,000

Market trends in Pittsboro

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$600K
$8.33KMoM
Sale-to-List Price
99.1%
0.4%MoM
Price per sq ft
$253
$9MoM
Available listings
128
15MoM

Around this home

What Locals Say about Pittsboro

At least 45 Trulia users voted on each feature.

  • 96 % Say car is needed

  • 91 % Say parking is easy

  • 88 % Say yards are well-kept

  • 87 % Say there's holiday spirit

  • 87 % Say it's dog friendly

  • 84 % Say people would walk alone at night

  • 82 % Say there's wildlife

  • 73 % Say neighbors are friendly

  • 73 % Say it's quiet

  • 63 % Say kids play outside

  • 57 % Say they plan to stay for at least 5 years

  • 56 % Say streets are well-lit

  • 50 % Say there are community events

  • 32 % Say there are sidewalks

  • 31 % Say it's walkable to restaurants

  • 15 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Daniela Speer
    "Many walk their dogs daily, and they respect their neighbors property by picking up after their dogs."
    0
    Flag
  • Kapreshia C.
    "Small children running and playing in the culdesac. Quiet neighborhood with no commotion, minimal to no crime in Pittsboro. Pittsboro Elementary school directly across the street."
    3
    Flag
  • Rmstein.83
    "I have lived in this neighborhood for four years and love living in a neighborhood with a country environment, chickens clucking, birds singing, barns in the distance, etc..."
    2
    Flag
  • James K.
    "very liberal area... nice views with the Haw River, Jordan lake... quaint downtown. there's a lot of improvements coming with the construction of Chatham park."
    0
    Flag
  • Daniela
    "Custom homes, no 2 are alike, acre lots, beautiful trees, perfect sunrises and sunsets, wonderful neighbors!!!"
    1
    Flag
  • James K.
    "this neighborhood is tucked away and had beautiful views. the are large and there is a lot of green space and trees. it's very quiet which allows for quite evenings on the front porch. there is very little through traffic."
    0
    Flag
  • Trulia User
    "Easy access to Pittsboro and Chapel Hill. Traffic moves smoothly, rarely experience extended slow downs. Traffic lights well synced. "
    1
    Flag
  • Andre B. D.
    "country roads to work for a nice calm drive. very rarely any traffic. wildlife and river crossings along the way."
    0
    Flag
  • Leah H.
    "All of my neighbors are awesome. This neighborhood is super friendly and there are lots of families with children. There is a good range of younger families and older adults. "
    0
    Flag
  • Andre B. D.
    " laid back and progressive at the same time. the city area is fun and quaint. you can live 5 minutes from town and be in the country away from everything. "
    0
    Flag
  • Michael D.
    "Pittsboro is awesome place to live new and up and coming parks and already has great vibe and atmosphere in town"
    0
    Flag
  • Jjoyms1
    "There’s a wonderful family atmosphere here with a Small town feel, and a variety of locally owned restaurants and shops."
    2
    Flag
  • Carol A. G.
    "Live in Fearrington Village and love it! Great neighborhoods, easy to assimilate, beautiful wooded countryside. walking paths & trails."
    0
    Flag
  • A L. T.
    "We purchased a home just off of the Haw River & couldn't be more pleased about it. Accessibility to so many different highways makes it easy to commute to several surrounding areas to include: Chapel Hill, Raleigh, Durham, Apex, Cary, Southern Pines just to name a few. Small town with a lot to offer. The projected growth in the area is quite overwhelming. Hoping the community pushes green building practices as much as possible seeing as it will be along the Haw River and Jordan Lake. "
    0
    Flag
  • Laurie J.
    "I live in Chapel Ridge Golf Community. We have so many activities going on here, that you rarely need to leave the community. Pool, Exercise Room, Homeowners Clubhouse, golf course, tennis, lessons for kids, holiday activities and parties, book clubs, wine club, dinner clubs, poker group. Easy to start a new group. Prettiest views in the area, and no traffic."
    0
    Flag

LGBTQ Local Legal Protections

The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
Copyright 2026 Doorify MLS of North Carolina. All rights reserved.

Frequently asked questions about 227 Windlestraw

  • What is 227 Windlestraw estimated to be worth?
    Trulia's estimated value for 227 Windlestraw in Pittsboro, NC is $521,700.
  • What is the price history for 227 Windlestraw?
    227 Windlestraw in Pittsboro, NC last sold for $532,500 in November 2025.
  • Is Pittsboro a buyer's or seller's market?
    Pittsboro is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Pittsboro?
    The median sale price in Pittsboro is $600K. That is up $8.33K from the prior month.
  • Does 227 Windlestraw have air conditioning?
    Yes, 227 Windlestraw in Pittsboro, NC has air conditioning.
  • Does 227 Windlestraw have a pool?
    Yes, 227 Windlestraw in Pittsboro, NC has a pool.

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