49 Chestertown Dr, Pinehurst, NC 28374
Property image
Property image
OFF MARKET

$2,480,300

Trulia Estimate
  • 5 Beds
  • 5.5 Baths
  • 7,193 sqft (on 1.39 acres)

49 Chestertown Dr, Pinehurst, NC 28374

Est. Refi. Payment $13,937/mo*
Refinance Your Home
Currently Off Market - Sold Mar 9, 2022 for $1,725,000

Home Value

Trulia Estimate
$2.48M
Since last month
Increased$28K (+1.1%)
Since last year
Increased$162K (+7%)
Since last sale
Increased$755K (+43.8%)
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 +90% in the last 10 years
MonthEstimated value
2026
August 2026$2.48M
August 2026$2.47M
July 2026$2.45M
June 2026$2.52M
May 2026$2.46M
April 2026$2.42M
March 2026$2.4M
February 2026$2.32M
January 2026$2.32M
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
0.03
Single-Family Home
$1,350,000
11/20/25
4
6
5,382
0.05
Single-Family Home
$3,650,000
12/18/25
5
5
6,244
0.27
Single-Family Home
$1,675,000
05/21/26
4
4.5
3,663
0.26
Single-Family Home
$1,899,000
04/01/26
4
3.5
4,479
0.46
Single-Family Home
$2,125,000
10/27/25
4
5
5,884
0.13
Single-Family Home
$1,240,000
02/09/26
3
3.5
3,301
0.31
Single-Family Home
$2,725,000
11/20/25
7
6.5
6,320
0.36
Single-Family Home
$1,345,000
06/02/26
3
4.5
3,393
0.53
Single-Family Home
$1,350,000
01/08/26
4
4.5
4,258
0.56
Single-Family Home
$1,699,000
03/27/26
4
4.5
3,628

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
0.03
$1,350,000
4
6
5,382
Recently Sold
0.05
$3,650,000
5
5
6,244
Recently Sold
0.12
-
-
-
-
Off Market
0.14
$495,000
-
-
-
For Sale
0.14
$665,500
4
3
3,029
Recently Sold
0.13
$1,240,000
3
3.5
3,301
Recently Sold
0.16
$658,250
4
4
3,040
Recently Sold
0.16
$673,250
5
3.5
3,244
Recently Sold
0.17
$450,000
-
-
-
Recently Sold
0.16
$445,000
-
-
-
For Sale
0.19
$450,000
-
-
-
Recently Sold
0.16
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 49 Chestertown Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2010
1.39 acre lot
7,193 sqft
$345/sqft
Garage

About this House

Incredible custom designed brick and stone home in Forest Creek Golf Club, one of area's premier gated communities and private courses. . A Certified Gold Green Home and Energy Star Qualified Home built by Will Huntley with Huntley Design Build, one of the area's premier builder, is situated on 1.3 acres just off hole #3 of the South Course. This home boasts approx. 7,000 sq. ft. of heated living space, + 1,100 sq. ft. veranda hosting a 20 ft. stone/ wood burning fireplace, vaulted pine ceilings and outdoor kitchen. An additional 2000 sq. ft. of walk-in attic space accounts for almost 10,000 sq. ft. of useable space. The home encompasses architectural details and exceptional craftsmanship. This golf course elegance offers numerous stunning features:< Leather finished Granite
< Entry barrel- vaulted ceiling embedded with crystals
< Main level owner's suite
< Guest suites
< 3 stop hydraulic elevator
< 900 bottle wine cellar
< Workout room
< Golf simulator/theatre room
< Gourmet expansive kitchen with leathered granite + walk-in pantry
< Separate hobby/cigar room with own venting
< 2 Tankless water heaters for instant hot water
< Geothermal 5-zone HVAC system
< Sealed-conditioned attic and crawl space + under slab drain system
< Four car garage w/ 3 large doors
< Irrigation well
< Whole house generator
< Intercom+16 zone whole house audio
< Central vac
< Covered gutters
< Security system
< Many more outstanding features...
49 Chestertown Dr, Pinehurst, NC 28374 is a 5 bedroom, 6 bathroom, 7,193 sqft single-family home built in 2010. It last sold for $1,725,000 on Mar 9, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,480,300, with a rent estimate of $4,896/month.

Home Details for 49 Chestertown Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9Types of Rooms: Breakfast Nook, Dining Room, Family Room, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1ElevatorFloors: Tile, Carpet, Hardwood
Appliances & Utilities
Washer
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: CompositionExterior: StonePorch
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2010
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 1.39 acres

Price and Tax history

DateEventPrice
Mar 9, 2022
Source: N/A
Sold
$1,725,000
Oct 7, 2020
Source: Agent Provided
ListingRemoved
$1,895,000
Sep 13, 2019
Source: Agent Provided
Listed For Sale
$1,895,000
Apr 20, 2018
Source: Hive MLS #185096
Sold
$1,725,000
Feb 21, 2006
Source: N/A
Sold
$265,000

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

Frequently asked questions about 49 Chestertown Dr

  • What is 49 Chestertown Dr estimated to be worth?
    Trulia's estimated value for 49 Chestertown Dr in Pinehurst, NC is $2,480,300.
  • What is the price history for 49 Chestertown Dr?
    49 Chestertown Dr in Pinehurst, NC last sold for $1,725,000 in March 2022.
  • 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 49 Chestertown Dr have air conditioning?
    Yes, 49 Chestertown Dr in Pinehurst, NC has air conditioning.
  • How big is the lot at 49 Chestertown Dr?
    The lot at 49 Chestertown Dr in Pinehurst, NC is about 1.4 acres.

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