65 Chestertown Drive, Pinehurst, NC 28374
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Property image
OFF MARKET

65 Chestertown Drive
Pinehurst, NC 28374

  • 6 Beds
  • 6 Baths
  • 5,056 sqft (on 0.96 acres)

$1,841,000

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $10,103/mo*

$1,841,000

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $10,103/mo*
6 Beds
6 Baths
5,056 sqft
(on 0.96 acres)

Local Information

  • Map ViewExplore the area around 65 Chestertown Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

The moment you enter this masterpiece by Fernando Silva, you'll be blown away by the elevated details throughout. Situated on the 3rd tee of the South Course in Forest Creek, you'll step into a soaring great room finished with wood accent ceilings. A showstopping kitchen boasts custom inset cabinetry, handmade Moroccan tile backsplash, unlaquered brass fixtures, a marble island, and soapstone perimeter tops. Thermador appliances include a 48'' gas range, a column freezer, and a refrigerator. You'll also find a wet bar with an ice maker and a wine fridge, and a color-drenched butler's pantry with natural stone floors. The heart of this home is made to show off.

The living room sliders open to achieve a seamless indoor/ outdoor space. The covered back patio is complete with marble pavers, an outdoor kitchen, and a fire pit.

A main floor primary retreat welcomes you at the end of every day with a spa-inspired bathroom that leaves nothing to be desired. Enjoy a soaking tub and a zero-entry shower with Kohler brass plumbing fixtures. Dual custom closets flank the primary bathroom. With direct access to the back patio, start your morning with a quiet coffee or enjoy a cocktail at sundown. A dedicated office with built-ins provides a sophisticated space to work from home. Down the hall, your guests will have privacy with an ensuite of their own. The laundry room has ample storage and a porcelain utility sink.

Upstairs, find a sitting area, 4 generous bedrooms, and 3 bathrooms. A separate stairwell leads to a massive bonus room with commanding golf views and full bath.

But it's what you can't see that makes this home spectacular. It's spray foam insulation, Pella windows, a fully encapsulated crawlspace, 8' solid core doors, epoxy floors in the 3-car garage, a full home Generac generator, and so much more.

Life in Forest Creek is a dream. Access to two Tom Fazio golf courses (club membership separate), a pool, fitness facility, clubhouse, and more.
65 Chestertown Drive, Pinehurst, NC 28374 is a 6 bedroom, 7 bathroom, 5,056 sqft single-family home built in 2025. It last sold for $1,800,000 on Jul 30, 2025 (9% below the $1,975,000 asking price). It is currently off market. The Trulia Estimate is $1,841,000, with a rent estimate of $4,605/month.

Home Highlights

Parking
3 Car Garage
Outdoor
Porch
A/C
Heating & Cooling
HOA
$176/Monthly
Price/Sqft
No Info
Listed
118 days ago

Home Details for 65 Chestertown Drive

Interior Features

Interior Details
Basement: NoneNumber of Rooms: 10Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Bedroom 6, Bonus Room, Dining Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 7Number of Bathrooms (full): 5Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 5056 Square Feet
Appliances & Utilities
Utilities: Sewer Connected, Water ConnectedAppliances: Double Oven, DishwasherDishwasherLaundry: Laundry Room
Heating & Cooling
Heating: Electric,Heat PumpHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: Gas LogHas a Fireplace
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, PorchFencing: NoneExterior: Outdoor KitchenFoundation: See Remarks, Crawl Space
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Has a GarageHas an Attached GarageParking Spaces: 3Parking: Garage Faces Side,Attached,Garage Door Opener
Frontage
Frontage Type: Golf CourseRoad Frontage: Private RoadNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 39

Property Information

Year Built
Year Built: 2025
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Wood Frame, Stick BuiltArchitecture: Wood Frame,Stick Built
Building
Construction Materials: Stone, Fiber Cement, Wood FrameIs a New Construction
Property Information
Parcel Number: 98000927

Price & Status

Price
List Price: $1,975,000
Status Change & Dates
Off Market Date: Thu Jun 26 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: 5056 Square Feet

HOA

HOA Name: Forest Creek Property Owners AssociationHOA Phone: 910-295-3791HOA Fee Frequency (second): AnnuallyAssociation for this Listing: Mid Carolina Regional MLSHas an HOAHOA Fee: $2,117/Annually

Lot Information

Lot Area: 0.96 acres

Listing Info

Special Conditions: Standard

Offer

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

Miscellaneous

Mls Number: 100508483Living Area Range: 5000 - 5499Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square FeetShowing Requirements: Appointment Only, No SignStart Showing Date: Mon Jun 02 2025

Additional Information

HOA Amenities: Golf Course
Last check for updates: about 12 hours ago
Listed by Leigh Amigo, (706) 728-4108
Keller Williams Pinehurst
Bought with: Jenny Simmons, (704) 574-6285, Call It Closed International Realty
Originating MLS: Mid Carolina Regional MLS
Source: Hive MLS, MLS#100508483

Price History for 65 Chestertown Drive

DatePriceEventSource
01/19/2026$190,000ListingRemovedHive MLS #100366920
07/30/2025$1,800,000Sold
Hive MLS #100508483
06/26/2025$1,975,000ContingentHive MLS #100508483
06/02/2025$1,975,000Listed For SaleHive MLS #100508483
04/12/2023ListingRemovedLPRMLS #697324
01/23/2023$190,000Listed For SaleLPRMLS #697324
01/22/2023ListingRemovedHive MLS #100363923
01/08/2023$190,000Listed For SaleHive MLS #100363923
12/09/2022ListingRemovedDoorify MLS #LP693990
10/25/2022$190,000Listed For SaleLPRMLS #693990
06/01/2022$150,000Sold
Hive MLS #100298319
03/16/2022$150,000PendingHive MLS #100298319
03/02/2022$150,000PendingToActiveHive MLS #100298319
02/02/2022$150,000PendingHive MLS #100298319
01/04/2022$150,000PriceChange
Hive MLS #100298319
05/25/2021$140,000Listed For SaleMCR #206208

Market trends in Pinehurst

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$514K
$20.42K
MoM
Sale-to-List Price
97.3%
0.3%
MoM
Price per sq ft
$242
$5
MoM
Available listings
220
2
MoM
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Property Tax and Assessment

Year2024
Tax$1,020
Assessment$160,000
Home facts updated by county records

Comparable Sales for 65 Chestertown Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.12
Single-Family Home
$1,899,000
04/01/26
4
3.5
4,479
0.19
Single-Family Home
$2,725,000
11/20/25
7
6.5
6,320
0.27
Single-Family Home
$3,650,000
12/18/25
5
5
6,244
0.25
Single-Family Home
$3,192,500
05/28/26
4
5.5
5,141
0.19
Single-Family Home
$1,350,000
11/20/25
4
6
5,382
0.41
Single-Family Home
$1,699,000
03/27/26
4
4.5
3,628
0.43
Single-Family Home
$1,675,000
05/21/26
4
4.5
3,663
0.44
Single-Family Home
$1,425,000
11/04/25
5
4.5
3,360
0.36
Single-Family Home
$1,345,000
06/02/26
3
4.5
3,393

Nearby homes

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Assigned Schools

These are the assigned schools for 65 Chestertown Drive.
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."

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Homes for sale near 65 Chestertown Drive

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Off Market Homes Near 65 Chestertown Drive

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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 2026-07-09 15:32:35 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