Is a car needed in Pittsboro, NC?

As of early 2026, 96% of users say car is needed

Is parking easy in Pittsboro, NC?

As of early 2026, 91% of users say parking is easy

Are yards well-kept in Pittsboro, NC?

As of early 2026, 88% of users say yards are well-kept

Does Pittsboro, NC show holiday spirit?

As of early 2026, 87% of users say there's holiday spirit

Is Pittsboro, NC dog-friendly?

As of early 2026, 87% of users say it's dog friendly

Would people walk alone at night in Pittsboro, NC?

As of early 2026, 84% of users say people would walk alone at night

Is there wildlife in Pittsboro, NC?

As of early 2026, 82% of users say there's wildlife

Are neighbors friendly in Pittsboro, NC?

As of early 2026, 73% of users say neighbors are friendly

Is Pittsboro, NC quiet?

As of early 2026, 72% of users say it's quiet

Do kids play outside in Pittsboro, NC?

As of early 2026, 63% of users say kids play outside

Do residents of Pittsboro, NC plan to stay at least 5 years?

As of early 2026, 57% of users say they plan to stay for at least 5 years

Are the streets well-lit in Pittsboro, NC?

As of early 2026, 54% of users say streets are well-lit

Are there community events in Pittsboro, NC?

As of early 2026, 51% of users say there are community events

Does Pittsboro, NC have sidewalks?

As of early 2026, 32% of users say there are sidewalks

Is Pittsboro, NC walkable to restaurants?

As of early 2026, 31% of users say it's walkable to restaurants

Is Pittsboro, NC walkable to grocery stores?

As of early 2026, 15% of users say it's walkable to grocery stores

PENDING

0.64 ACRES

223 Windlestraw
Pittsboro, NC 27312

3 Beds
2 Baths
2,239 sqft (on 0.64 acres)

$575,000

Est. Mortgage $3,291/mo*

Get Pre-Qualified

$575,000

Est. Mortgage $3,291/mo*

Get Pre-Qualified

3 Beds

2 Baths

2,239 sqft

(on 0.64 acres)

Local Information

-- mins to

Commute Destination

Description

*Now Under Contract* 223 Windlestraw sits on a deep, wooded lot offering exceptional privacy and scenic views in the Fearrington Village Historic District. This one-level contemporary home features high ceilings, abundant natural light from expansive windows, and parquet wood floors. A front walkway leads to a deck with seating and a welcoming foyer that opens to a spacious living room with a fireplace, along with a separate dining room. The remodeled kitchen includes stainless-steel appliances, a breakfast area, and adjacent laundry room with ample pantry storage. The primary suite, located at the rear of the home, offers a private bath and two walk-in closets, complemented by two additional bedrooms and a full bath. A sunroom with three walls of windows overlooks the natural landscape. An oversized two-car garage with workshop space is connected by a covered walkway, and a lower-level workshop/storage area opens to the backyard. The mature landscaping - featuring rhododendrons, camellias, azaleas, dogwoods, and a cherry tree - ensures seasonable color from late winter through summer, with brick walkways and a patio completing the setting.

Home Highlights

Parking

Garage

Outdoor

Porch, Deck

A/C

Heating & Cooling

HOA

$26/Monthly

Price/Sqft

$257

Listed

30 days ago

Home Details for 223 Windlestraw

Interior Features
Interior Details Basement: Crawl Space, Exterior Entry, Storage Space, Unfinished, WorkshopNumber of Rooms: 8
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 2239 Square Feet
Appliances & Utilities Appliances: Dishwasher, Dryer, Gas Range, Gas Water Heater, Range Hood, Refrigerator, Stainless Steel Appliance(s), WasherDishwasherDryerLaundry: Laundry Room,SinkRefrigeratorWasher
Heating & Cooling Heating: Forced Air, Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Fireplace: Living RoomHas a Fireplace
Windows, Doors, Floors & Walls Window: Skylight(s)Flooring: Parquet, Tile
Levels, Entrance, & Accessibility Stories: 1Levels: OneFloors: Parquet, Tile
View Has a View

Exterior Features
Exterior Home Features Roof: ShinglePatio / Porch: Covered, Deck, Front PorchFoundation: OtherNo Private Pool
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageNo Attached GarageParking Spaces: 2Parking: Asphalt,Detached,Driveway,Garage,Garage Faces Front
Pool Pool: Swimming Pool Com/Fee
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 2239 Square Feet

Days on Market
Days on Market: 30

Property Information
Year Built Year Built: 1983
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialStructure Type: Site BuiltArchitecture: Contemporary
Building Construction Materials: Wood SidingNot a New Construction
Property Information Parcel Number: 19123

Price & Status
Price List Price: $575,000Price Per Sqft: $257

Active Status
MLS Status: Pending

Media
See Virtual Tour

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

Agent Information
Listing Agent Listing ID: 10161334

Building
Building Area Building Area: 2239 Square Feet

Community
Not Senior Community

HOA
HOA Fee Includes: UnknownHas an HOAHOA Fee: $315/Annually

Lot Information
Lot Area: 0.64 acres

Listing Info
Special Conditions: Standard

Miscellaneous
BasementMls Number: 10161334Above Grade Unfinished Area: 2239

Additional Information
Source Internet Entire Listing Display

Last check for updates: about 8 hours ago

Listing courtesy of Tony Hall, (919) 740-9611

Berkshire Hathaway HomeService

Source: Doorify MLS, MLS#10161334

Also Listed on Doorify MLS.

Price History for 223 Windlestraw

Date	Price	Event	Source
04/24/2026	$575,000	Pending	Doorify MLS #10161334

04/20/2026	$575,000	Listed For Sale	Doorify MLS #10161334

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Property Tax and Assessment

Year	2025
Tax	$4,114
Assessment	$563,715

Home facts updated by county records

Comparable Sales for 223 Windlestraw

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
182 Hedgerow, Pittsboro, NC	0.16	Single-Family Home	$590,000	05/20/26	3	2	2,079
251 Fox Rdg, Pittsboro, NC	0.21	Single-Family Home	$581,000	04/24/26	3	2	2,146
94 Meadow Run, Pittsboro, NC	0.46	Single-Family Home	$400,000	12/19/25	3	2	1,878
127 Creekwood, Pittsboro, NC	0.43	Single-Family Home	$645,000	12/15/25	3	2	2,047
252 Fox Rdg, Pittsboro, NC	0.20	Single-Family Home	$375,000	07/18/25	2	2	2,002
128 Shadowbrook, Pittsboro, NC	0.45	Single-Family Home	$705,000	08/01/25	3	3	2,099

Assigned Schools

These are the assigned schools for 223 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
72 % Say it's quiet
63 % Say kids play outside
57 % Say they plan to stay for at least 5 years
54 % 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
Resident
7mo ago
"Many walk their dogs daily, and they respect their neighbors property by picking up after their dogs."
0
Flag
Kapreshia C.
Resident
5y ago
"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
Resident
5y ago
"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.
Resident
5y ago
"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
Resident
6y ago
"Custom homes, no 2 are alike, acre lots, beautiful trees, perfect sunrises and sunsets, wonderful neighbors!!!"
1
Flag
James K.
Resident
6y ago
"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
Resident
6y ago
"Easy access to Pittsboro and Chapel Hill. Traffic moves smoothly, rarely experience extended slow downs. Traffic lights well synced. "
1
Flag
Andre B. D.
Resident
7y ago
"country roads to work for a nice calm drive. very rarely any traffic. wildlife and river crossings along the way."
0
Flag
Leah H.
Resident
7y ago
"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
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Andre B. D.
Resident
7y ago
" 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
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Michael D.
Resident
7y ago
"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
Resident
7y ago
"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.
11y ago
"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.
12y ago
"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.
12y ago
"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
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LGBTQ Local Legal Protections

Tony Hall, Berkshire Hathaway HomeService

Agent Phone: (919) 740-9611

223 Windlestraw, Pittsboro, NC 27312 is a 3 bedroom, 2 bathroom, 2,239 sqft single-family home built in 1983. This property is currently available for sale and was listed by Doorify MLS on Apr 20, 2026. The MLS # for this home is MLS# 10161334.

223 Windlestraw
Pittsboro, NC 27312

$575,000

$575,000

Local Information