45 Chestertown Drive, Pinehurst, NC 28374
Property image
Property image
SOLD
DEC 18, 2025

$3,697,700

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 6,244 sqft (on 0.91 acres)

45 Chestertown Drive, Pinehurst, NC 28374

Est. Refi. Payment $21,371/mo*
Refinance Your Home
Currently Off Market - Sold Dec 18, 2025 for $3,650,000 (24% above list price)

Home Value

Trulia Estimate
$3.7M
Since last month
Decreased$6K (-0.2%)
Since last year
Increased$2M (+117.8%)
Since last sale
Increased$50K (+1.4%)
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 +264% in the last 10 years
MonthEstimated value
2026
September 2026$3.7M
August 2026$3.7M
July 2026$3.71M
June 2026$3.7M
May 2026$3.69M
April 2026$3.69M
March 2026$3.69M
February 2026$3.67M
January 2026$3.65M
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
0.35
Single-Family Home
$2,725,000
11/20/25
7
6.5
6,320
0.25
Single-Family Home
$1,675,000
05/21/26
4
4.5
3,663
0.08
Single-Family Home
$1,350,000
11/20/25
4
6
5,382
0.52
Single-Family Home
$3,192,500
05/28/26
4
5.5
5,141
0.30
Single-Family Home
$1,899,000
04/01/26
4
3.5
4,479
0.18
Single-Family Home
$673,250
01/09/26
5
3.5
3,244
0.53
Single-Family Home
$1,350,000
01/08/26
4
4.5
4,258
0.18
Single-Family Home
$658,250
02/20/26
4
4
3,040
0.48
Single-Family Home
$2,125,000
10/27/25
4
5
5,884

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
0.08
$1,350,000
4
6
5,382
Recently Sold
0.11
$1,240,000
3
3.5
3,301
Recently Sold
0.15
$665,500
4
3
3,029
Recently Sold
0.11
-
-
-
-
Off Market
0.14
$2,495,000
5
6.5
4,273
For Sale
0.18
$658,250
4
4
3,040
Recently Sold
0.18
$673,250
5
3.5
3,244
Recently Sold
0.17
-
-
-
-
Off Market
0.18
$495,000
-
-
-
For Sale
0.16
-
-
-
-
Off Market
0.18
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 45 Chestertown Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2000
0.91 acre lot
6,244 sqft
$585/sqft
Garage
HOA $158/mo

About this House

This is an absolutely breathtaking property on nearly one acre in the prestigious gated Community of Forest Creek Golf Club. The grand stone gated entrance to privacy includes a circular driveway lined with gas lanterns and a beautifully landscaped entry walkway. Overlooking the 3rd green of Tom Fazio's South course, the expansive stone patio with wood burning fireplace is great for intimate evenings or entertaining large parties. Inside is full of charm and character, a home easily suited to formal and casual evenings. Special features abound in every room and nothing was spared in either design or quality of materials. Reclaimed heart pine, European stone flooring, custom Rutt cabinetry, and Waterworks fixtures are just a few of the exceptional features. The ground floor boasts an elegant living room, dining room and butler's pantry leading into an expansive gourmet kitchen and spectacular great room with floor to ceiling windows and a wood-burning fireplace. The great room adjoins a Southern-style covered porch and patio with Pennsylvania flagstone paving and an impressive stacked-stone outdoor fireplace, allowing for a great indoor-outdoor experience. All fireplaces are wood burning except in the bedroom and all have gas starters. A luxurious guest suite, that could equally serve as a first floor Master bedroom, as well as a beautifully appointed library with fireplace, and wet bar complete the first floor. A second Master suite with double walk-in closets, balcony, fireplace and sumptuous bathroom is on the 2nd floor. The home has a total of 5 bedrooms, 4 baths, 2 half baths and numerous additional multi use spaces. Completing this remarkable home is a handsome custom wine cellar, designed for storage and entertaining on the lower level. Custom furnishings negotiable. Two adjacent lots, owned by the seller, negotiable. One of a kind! Club membership not required. Exterior recently painted.
45 Chestertown Drive, Pinehurst, NC 28374 is a 5 bedroom, 6 bathroom, 6,244 sqft single-family home built in 2000. It last sold for $3,650,000 on Dec 18, 2025 (24% above the $2,950,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,697,700, with a rent estimate of $4,624/month.
Last check for updates: about 15 hours ago
Listed by Lin Hutaff, (910) 528-6427
Lin Hutaff's Pinehurst Realty Group
Bought with: Dale B Heck, (910) 528-4652, Sandhills Luxury Homes LLC
Originating MLS: Mid Carolina Regional MLS
Source: Hive MLS, MLS#100500878

Home Details for 45 Chestertown Drive

Interior Features

Interior Details
Number of Rooms: 15Types of Rooms: Master Bedroom, Dining RoomWet Bar
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 4Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 6244 Square Feet
Appliances & Utilities
Utilities: Sewer Available, Water Available
Heating & Cooling
Heating: Electric,Heat PumpHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Gas & Electric
No Electric on Property
Levels, Entrance, & Accessibility
Stories: 2Levels: Two
View
View: Golf Course

Exterior Features

Exterior Home Features
Roof: CompositionPatio / Porch: Covered, Patio, PorchFencing: NoneFoundation: Crawl Space
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Circular Driveway,Gravel
Frontage
Road Frontage: Private Road, PavedRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 675

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Wood FrameArchitecture: Wood Frame
Building
Construction Materials: Brick, Stone, Wood SidingNot a New Construction
Property Information
Parcel Number: 98000903

Price & Status

Price
List Price: $2,950,000Price Per Sqft: $585/sqft
Status Change & Dates
Off Market Date: Mon Oct 20 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Closed

Location

Direction & Address
City: PinehurstCommunity: Forest Creek
School Information
Elementary School: McDeeds Creek ElementaryJr High / Middle School: New Century MiddleHigh School: Union Pines HighHigh School District: Moore County Schools

Building

Building Area
Building Area: 6244 Square Feet

HOA

HOA Name: CASHOA Phone: 910-295-3791HOA Fee Frequency (second): AnnuallyAssociation for this Listing: Mid Carolina Regional MLSHas an HOAHOA Fee: $1,890/Annually

Lot Information

Lot Area: 0.91 acres

Listing Info

Special Conditions: Standard

Offer

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

Miscellaneous

Mls Number: 100500878Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square FeetShowing AttendedShowing Requirements: Appointment Only

Additional Information

HOA Amenities: Maintenance Common Areas,Maintenance Roads,Management,Security,Street Lights

Price and Tax history

DateEventPrice
Dec 18, 2025
Source: Hive MLS #100500878
Sold
$3,650,000
Oct 24, 2025
Source: Hive MLS #100500878
Contingent
$2,950,000
Oct 21, 2025
Source: Hive MLS #100500878
Pending
$2,950,000
Apr 12, 2025
Source: Hive MLS #100500878
Listed For Sale
$2,950,000
Mar 19, 2025
Source: Hive MLS #100444998
ListingRemoved
$2,950,000

Market trends in Pinehurst

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$598K
$7.92K
MoM
Sale-to-List Price
98.0%
0.1%
MoM
Price per sq ft
$249
$1
MoM
Available listings
231
2
MoM

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 donโ€™t commuteโ€ฆwork from home. Moving around the neighborhood is easy, just need to drive slowly. "
  • Mobrindley79
    "Weโ€™ve lived here almost 2 years. Love our location and family neighborhood. Weโ€™re in Village acres and weโ€™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! Itโ€™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 thereโ€™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."

LGBTQ Local Legal Protections

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 2026-09-13 22:53:26 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. ยฉ 2025-10-17 12:20:34 PDT Hive MLS

Frequently asked questions about 45 Chestertown Drive

  • What is 45 Chestertown Drive estimated to be worth?
    Trulia's estimated value for 45 Chestertown Drive in Pinehurst, NC is $3,697,700.
  • What is the price history for 45 Chestertown Drive?
    45 Chestertown Drive in Pinehurst, NC last sold for $3,650,000 in December 2025.
  • Is Pinehurst a buyer's or seller's market?
    Pinehurst is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Pinehurst?
    The median sale price in Pinehurst is $598K. That is down $7.92K from the prior month.
  • Does 45 Chestertown Drive have air conditioning?
    Yes, 45 Chestertown Drive in Pinehurst, NC has air conditioning.
  • How big is the lot at 45 Chestertown Drive?
    The lot at 45 Chestertown Drive in Pinehurst, NC is about 0.91 acres (39,640 sq ft).

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