227 Windlestraw, Pittsboro, NC 27312
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 $3,054/mo*
Refinance Your Home

$532,500

Last Sold: Nov 24, 2025
3% below list $550K
$272/sqft
Est. Refi. Payment $3,054/mo*
Refinance Your Home
3 Beds
2 Baths
1,960 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from November 25, 2025

Home Highlights

Parking
Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
$25/Monthly
Price/Sqft
$272/sqft
Listed
180+ days ago

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
Last check for updates: about 5 hours 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

Price History for 227 Windlestraw

DatePriceEventSource
11/24/2025$532,500Sold
Doorify MLS #10127366
10/28/2025$550,000PendingDoorify MLS #10127366
10/13/2025$550,000Listed For SaleDoorify MLS #10127366
05/23/2025$502,500Sold
Doorify MLS #10088938
04/21/2025$500,000PendingDoorify MLS #10088938
04/11/2025$500,000Listed For SaleDoorify MLS #10088938
03/28/2012$237,500ListingRemovedAgent Provided
12/05/2011$225,000Sold
N/A
10/02/2011$237,500PriceChange
Agent Provided
06/04/2011$249,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$3,409
Assessment$463,227
Home facts updated by county records

Comparable Sales for 227 Windlestraw

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
251 Fox Rdg, Pittsboro, NC
0.16
Single-Family Home
$581,000
04/24/26
3
2
2,146
182 Hedgerow, Pittsboro, NC
0.22
Single-Family Home
$590,000
05/20/26
3
2
2,079
252 Fox Rdg, Pittsboro, NC
0.15
Single-Family Home
$375,000
07/18/25
2
2
2,002
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
94 Meadow Run, Pittsboro, NC
0.45
Single-Family Home
$400,000
12/19/25
3
2
1,878

Nearby homes

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Assigned Schools

These are the assigned schools for 227 Windlestraw.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

  • 55 % Say streets are well-lit

  • 51 % 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
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  • 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
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  • 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
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  • 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."
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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.

Homes for rent near 227 Windlestraw

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227 Windlestraw, Pittsboro, NC 27312 is a 3 bedroom, 2 bathroom, 1,960 sqft single-family home built in 1983. This property is not currently available for sale. 227 Windlestraw was last sold on Nov 24, 2025 for $532,500 (3% lower than the asking price of $550,000). The current Trulia Estimate for 227 Windlestraw is $531,200.