Single Family Residence at 50 Mccaskill Road W, Pinehurst
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$2,495,000

50 Mccaskill Road W
Pinehurst, NC 28374
Listed by Lin Hutaff · Lin Hutaff's Pinehurst Realty Group
Bedrooms
5
Bathrooms
5.5
Living area
5,972 sqft
Year built
1917

About this home

''Blinkbonnie'' located in one of Pinehurst's most desirable neighborhoods, Old Town, was built by Simon B. Chapin,a New York financier and philanthropist. Mr. Chapin built five other cottages in Pinehurst during his time. Chapin was also credited with developing Myrtle beach, S.C. ''Blinkbonnie'' ,a popular name for 18th century estates in Scotland, conveyed a sense of charm, pastoral beauty and peace. Built in 1917, a formative period of Pinehurst's development, 50 McCaskill Rd is a fine example of the architecture and lifestyle that defined OLD TOWN in the early 1900s. Close to the Village shops, Carolina Hotel and Pinehurst Country Club, this 1.018 acre lot is full of old world charm. Upon entering the foyer, an exquisite living room with a stunning wood burning fireplace awaits. The sunny, elegant dining room entertains easily for small or large gatherings. The Carolina Sunroom boasts French doors, an oversized curved bay window, and a view overlooking pool area, Large den at end of hallway, can convert to 5th bedroom if desired. Kitchen has Subzero refrigerator, double Viking oven, 6 gas burner stove, large island. Butlers pantry has built in glass door cabinetry, lockable liquor cabinet and wine cooler. Easy access to kitchen and garage, first floor mudroom has washer, dryer, cubbies, and closet. Downstairs, a finished basement with rec room, kitchenette, mini fridge, ice maker, dishwasher, pool table, large closets. Media room has TV, full bath, closets, restaurant size walk in refrigerator. Upstairs, a beautiful staircase leads to 4 bedrooms, all with ensuite baths. Light and airy master bedroom has private sitting room, multiple closets and large bathroom. Library sits at the end of hallway with fireplace.Mature landscaping and vintage iron gates lead to brick and blue stone pathways, a tranquil French garden, fenced in area for dog park. Classic rectangular POOL (20x45) and POOL HOUSE with sauna, wet bar, wood smoker grill, full bath. GENERATOR

Highlights

Fireplace

Property details

MLS
Hive MLS
MLS #
100613779
Property type
Single Family Residence
Subdivision
Old Town
Status
Active
Days on market
739
On market date
November 1, 2026
Stories
N/A
Total bathrooms
5.5
Garage spaces
2
Parking spaces
2
Lot size
1.02 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
West Pine Elementary
3.57 mi away · Grades 0-5
Zoned school (attendance boundary, 2015-16 data)
3.7
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
395
Student:teacher ratio
15.8:1
District
Moore County Schools
Middle
West Pine Middle
3.52 mi away · Grades 6-8
Zoned school (attendance boundary, 2015-16 data)
3.7
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
710
Student:teacher ratio
17.3:1
District
Moore County Schools
High
Pinecrest High
2.58 mi away · Grades 9-12
Zoned school (attendance boundary, 2015-16 data)
3.4
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
2,219
Student:teacher ratio
21.1:1
District
Moore County Schools

Walkability

Blended score for Pinehurst's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

58
Somewhat walkable
out of 100
EPA National Walkability Index
7.8 / 20 -- Below average walkable
Google Places amenity density
85 / 100
Restaurants & cafes20
Grocery stores3
Parks9
Schools4
Transit stops0
Pharmacies5

Market position

How this listing compares to current activity in Pinehurst, from live MLS data.

On the market 739 days -- 623 more days than Pinehurst's current average of 116 days.
For reference, the median list price across 311 active listings in Pinehurst right now is $582,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

Adjust tax / insurance estimates
Est. monthly payment
$15,175/mo
$499,000 down
$1,996,000 loan
Principal & interest$12,946
Property tax (est.)$2,079
Home insurance (est.)$150

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Data source: Listing information provided by Hive MLS. Last updated 1 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.