50 Mccaskill Road W, Pinehurst, NC 28374
Property image
Property image
FOR SALE
1.02 ACRES

$2,495,000

  • 5 Beds
  • 5.5 Baths
  • 5,972 sqft (on 1.02 acres)

50 Mccaskill Road W, Pinehurst, NC 28374

Est. Mortgage $14,112/mo*
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Home Highlights

Single-Family Home
Built in 1917
1.02 acre lot
$418/sqft
2 Car Garage

Local Information

  • Map ViewExplore the area around 50 Mccaskill Road W.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

''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
Last check for updates: about 1 hour ago
Listing courtesy of Lin Hutaff, (910) 528-6427
Lin Hutaff's Pinehurst Realty Group
Originating MLS: Mid Carolina Regional MLS
Source: Hive MLS, MLS#100538542
Also Listed on Hive MLS.

Home Details for 50 Mccaskill Road W

Interior Features

Interior Details
Basement: Finished,OtherNumber of Rooms: 14Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bonus Room, Dining Room, Kitchen, Laundry, Living Room, Media Room, Office, Other, SunroomWet Bar
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5972 Square Feet
Appliances & Utilities
Utilities: Natural Gas Available, Sewer Connected, Water Connected, See RemarksAppliances: Vented Exhaust Fan, Mini Refrigerator, Gas Oven, Gas Cooktop, Built-In Microwave, Washer, Refrigerator, Ice Maker, Dryer, Double Oven, Disposal, DishwasherDishwasherDisposalDryerLaundry: Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: Electric,Heat Pump,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Electric
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Gas & Electric
No Electric on Property
Windows, Doors, Floors & Walls
Door: Storm Door(s)Flooring: Carpet, Marble, Tile, Wood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Marble, Tile, Wood
View
View: None

Exterior Features

Exterior Home Features
Roof: Architectural Shingle MembranePatio / Porch: Patio, BalconyFencing: Metal/Ornamental, Brick, Chain Link, Partial, Back YardOther Structures: FountainExterior: Shutters - Functional, Irrigation System, Gas Grill, Outdoor Kitchen, Storm DoorsFoundation: Brick/Mortar
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4Other Parking: circular&side driveHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Circular Driveway,See Remarks,Paved
Pool
Pool: In Ground, Pool/Spa ComboPool
Frontage
Waterfront: NoneFrontage Type: See RemarksRoad Frontage: City Street, State RoadNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 296Days on Market: 180+

Property Information

Year Built
Year Built: 1917
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Wood Frame, Stick BuiltArchitecture: Historic District
Building
Construction Materials: Aluminum Siding, Brick, Wood Siding, Wood FrameNot a New Construction
Property Information
Parcel Number: 00029115

Price & Status

Price
List Price: $2,495,000Price Per Sqft: $418
Status Change & Dates
Possession Timing: See Remarks

Active Status

MLS Status: Active

Location

Direction & Address
City: PinehurstCommunity: Old Town
School Information
Elementary School: Pinehurst ElementaryJr High / Middle School: West PineHigh School: Pinecrest HighHigh School District: Moore County Schools

Agent Information

Listing Agent
Listing ID: 100538542

Building

Building Area
Building Area: 5972 Square Feet

HOA

HOA Fee Frequency (second): AnnuallyAssociation for this Listing: Mid Carolina Regional MLSNo HOA

Lot Information

Lot Area: 1.018 Acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional

Miscellaneous

Mls Number: 100538542Living Area Range: 5500 - 5999Attic: Access Only, Attic FanAbove Grade Unfinished Area Units: Square FeetBack On Market Date: Fri May 01 2026Below Grade Unfinished Area Units: Square FeetShowing AttendedShowing Considerations: OccupiedShowing Requirements: Appointment Only, Lockbox

Around this home

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 Pinehurst

At least 101 Trulia users voted on each feature.
  • 94 % Say car is needed

  • 89 % Say parking is easy

  • 88 % Say yards are well-kept

  • 86 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 83 % Say it's quiet

  • 76 % Say people would walk alone at night

  • 62 % Say kids play outside

  • 62 % Say they plan to stay for at least 5 years

  • 56 % Say neighbors are friendly

  • 55 % Say there's wildlife

  • 40 % Say there are community events

  • 29 % Say streets are well-lit

  • 26 % Say there are sidewalks

  • 22 % Say it's walkable to restaurants

  • 14 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Kimojha Brooks
    "The town is unique and friendly and everything is close by. There are plenty of stores and restaurants too. "
  • Spencer James
    "health lectures senior friendly community events and input include movies music food farmers market etc"
  • Patrick Norris
    "I don’t commute…work from home. Moving around the neighborhood is easy, just need to drive slowly. "
  • Mobrindley79
    "We’ve lived here almost 2 years. Love our location and family neighborhood. We’re in Village acres and we’re also not far from Taylortown or Pinehurst Village. We are golfers, however my husbands recovery from major back surgery last year has put our golf on hold. But there are lots of golf carts driving on our roads to their tee times! It’s great!"
  • Gretchengeorge1
    "Easy and convenient. Not too ouch traffic. The roundabout keeps things moving well. Pinehurst is a great place! "
  • Madison M.
    "There are a lot of pet owners in the neighborhood. People really like dogs and stop to say hi. There is not a fenced dog park and very few doggy/bag stations."
  • Lizabthn
    "I've lived here now 7 months and we love it. Neighbors are super friendly and always helpful. Love that you see your neighbors either walking their dogs or pushing a stroller. I especially like that when you drive by someone, they wave hello. Great family friendly neighborhood! Lots of kids! "
  • Tina A. K.
    "It takes me about 15 minutes to get to work, 7 miles. The traffic circle usually takes the most time but there’s also a stop light along the way. "
  • Liz
    "Very family-friendly neighborhood with many activities and local shops. Great place to raise a family, vacation and retire. Big on Golfing! "
  • BCW
    "Friendly people. Famous for its golf courses. Great restaurants. Quaint village. Great newcomers clubs with many activities on a weekly basis...something for everyone."
  • Cindy S.
    "I work part time and work is only 10 minutes away. This is a very small community. No public transportation needed. "
  • HH
    "Lived here for 12 years...safe and very comfortable! Good neighbors and very child friendly. The schools assigned to this neighborhood are also exceptional."
  • Jill F.
    "It is a very family friendly area that is super safe, reminds me of how it use to be when we were young."
  • Jill F.
    "Every month in each town there are local concerts that are family friendly during the spring through fall months. "
  • Sean K.
    "We like the quiet, quaint neighborhood. We are very close to the village and grocery stores and shopping. "
  • Kyndalboykin
    "I've lived here for 1 year now. I feel extremely safe in my neighborhood. We love the quite laid back feeling, also a good mix of people within our community. Also I love that Aberdeen, Pinehurst and Southern Pines are ALL very convenient and great cities! "
  • Unspecified
    "Low crime rate and a reasonable cost of living. Excellent medical care abounds and there are several miles of walking trails."

Market trends in Pinehurst

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$605K
$41.33K
MoM
Sale-to-List Price
98.1%
Price per sq ft
$250
$1
MoM
Available listings
229
13
MoM

Home Value

Trulia Estimate
$2.25M
Since last month
Decreased$6K (-0.3%)
Since last year
Increased$325K (+16.9%)
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 +149% in the last 10 years
MonthEstimated value
2026
August 2026$2.25M
August 2026$2.25M
July 2026$2.26M
June 2026$2.26M
May 2026$2.27M
April 2026$2.27M
March 2026$2.27M
February 2026$2.27M
January 2026$2.28M
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
0.19
Single-Family Home
$2,900,000
10/16/25
6
5.5
5,600
0.10
Single-Family Home
$1,250,000
10/27/25
4
5
3,817
0.31
Single-Family Home
$1,962,500
11/21/25
5
5.5
4,650
0.28
Single-Family Home
$2,295,000
02/06/26
4
4.5
4,608
0.26
Single-Family Home
$1,725,000
03/31/26
4
4.5
3,824
0.39
Single-Family Home
$855,000
12/23/25
4
4
3,834
0.35
Single-Family Home
$1,700,000
08/14/26
5
3.5
4,983
0.20
Single-Family Home
$1,895,000
05/18/26
3
3.5
2,968
0.37
Single-Family Home
$650,000
12/29/25
4
2.5
2,566

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
0.04
$2,245,000
4
5.5
5,286
For Sale
0.08
-
-
-
-
Off Market
0.10
$1,271,500
4
5
3,817
Off Market
0.12
-
-
-
-
Off Market
0.12
-
-
-
-
Off Market
0.13
-
-
-
-
Off Market
0.16
$2,795,000
7
8.5
10,405
For Sale
0.19
$2,943,500
6
5.5
5,600
Off Market
0.17
$1,401,300
4
4.5
5,100
Off Market
0.20
$1,895,000
3
3.5
2,968
Recently Sold
0.22
$2,073,400
4
4
5,540
Off Market

Price and Tax history

DateEventPrice
Oct 29, 2025
Source: Hive MLS #100538542
Listed For Sale
$2,495,000
Oct 13, 2025
Source: Hive MLS #100335282
ListingRemoved
$1,850,000
Feb 21, 2023
Source: Coldwell Banker Advantage
ListingRemoved
Jun 23, 2022
Source: Hive MLS #100335282
Listed For Sale
$1,850,000

LGBTQ Local Legal Protections

Lin Hutaff, Lin Hutaff's Pinehurst Realty Group
Agent Phone: (910) 528-6427
The data relating to real estate on this web site comes in part from the Internet Data Exchange program of Hive MLS, and is updated as of 2026-09-05 00:50:10 PDT. All information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal. Neither listing broker(s) nor Zillow, Inc. shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. © 2025-10-17 12:20:34 PDT Hive MLS

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Frequently asked questions about 50 Mccaskill Road W

  • What is the estimated monthly payment for 50 Mccaskill Road W?
    Based on a $2,495,000 list price with 20% down at today's rates, the estimated monthly payment for 50 Mccaskill Road W in Pinehurst, NC is approximately $14,291 (about $13,072 principal & interest, $1,144 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 50 Mccaskill Road W compare to homes in Pinehurst?
    50 Mccaskill Road W in Pinehurst, NC is listed at $2,495,000, about 312% above the $605K median sale price in Pinehurst.
  • What do residents say about Pinehurst?
    Residents describe Pinehurst, NC as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See homes for sale in Pinehurst, NC.
  • What are the closest schools to 50 Mccaskill Road W?
    The closest schools to 50 Mccaskill Road W in Pinehurst, NC are Pinecrest High School (rated 6/10), Pinehurst Elementary School (rated 10/10), West Pine Middle School (rated 6/10).
  • Does 50 Mccaskill Road W have air conditioning?
    Yes, 50 Mccaskill Road W in Pinehurst, NC has air conditioning.
  • Does 50 Mccaskill Road W have a pool?
    Yes, 50 Mccaskill Road W in Pinehurst, NC has a pool.
50 Mccaskill Road W, Pinehurst, NC 28374 is a 5 bedroom, 6 bathroom, 5,972 sqft single-family home built in 1917. This property is currently available for sale and was listed by Hive MLS on Oct 29, 2025. The MLS # for this home is MLS# 100538542.