44 Chestertown Dr, Pinehurst, NC 28374
OFF MARKET

44 Chestertown Dr
Pinehurst, NC 28374

  • 4 Beds
  • 3,840 sqft (on 0.91 acres)
4 Beds
3,840 sqft
(on 0.91 acres)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
0.06
Lot/Land
$545,000
06/30/26
-
-
0.10
Lot/Land
$450,000
05/11/26
-
-
0.14
Lot/Land
$300,000
10/07/25
-
-
0.26
Lot/Land
$275,000
04/02/26
-
-
0.25
Lot/Land
$450,000
03/18/26
-
-
0.35
Lot/Land
$375,000
10/28/25
-
-
0.22
Lot/Land
$435,000
12/29/25
-
-
0.64
Lot/Land
$135,000
05/19/26
-
-
0.65
Lot/Land
$400,000
10/08/25
-
-
0.71
Lot/Land
$335,000
04/01/26
-
-

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
0.05
$977,900
4
4.5
4,003
Off Market
0.04
$960,900
4
4.5
3,444
Off Market
0.05
$1,899,000
4
3.5
4,479
Recently Sold
0.06
$545,000
-
-
-
Recently Sold
0.08
$1,845,800
6
6
5,056
Off Market
0.11
$1,299,000
4
2.5
3,206
For Sale
0.10
-
-
-
-
Off Market
0.10
$450,000
-
-
-
Recently Sold
0.12
$495,000
-
-
-
For Sale
0.11
$2,725,000
7
6.5
6,320
Recently Sold
0.16
-
-
-
-
Off Market
0.13
$1,453,300
4
4.5
4,393
Off Market

Local Information

  • Map ViewExplore the area around 44 Chestertown Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Lot/Land
Year Built
2022
Lot Size
0.91 acres
Living Area
3,840 sqft
Parking
Garage

About this House

Build your custom home on this wonderful Forest Creek lot - .91 acre. Located at intersection of Elkton & Chestertown Drive.
44 Chestertown Dr, Pinehurst, NC 28374 is a 4 bedroom, 3,840 sqft lot/land built in 2022. It last sold for $72,500 on Mar 17, 2021. It is currently off market. The Trulia Estimate rent is $3,172/month.

Home Details for 44 Chestertown Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1.5
Interior Details
AtticNumber of Rooms: 9
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 2022
Property Type / Style
Property Type: Lot Land

Exterior Features

Exterior Home Features
DeckFoundation Type: Crawl Raised
Parking & Garage
GarageParking: Garage Attached

Lot Information

Lot Area: 0.91 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Mar 17, 2021
Source: N/A
Sold
$72,500
Aug 12, 2020
Source: Agent Provided
Listed For Sale
$80,000
Jul 3, 2006
Source: N/A
Sold
$130,000

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

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."

LGBTQ Local Legal Protections

Frequently asked questions about 44 Chestertown Dr

  • What is the price history for 44 Chestertown Dr?
    44 Chestertown Dr in Pinehurst, NC last sold for $72,500 in March 2021.
  • 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 $605K. That is up $41.33K from the prior month.
  • 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 recently sold homes in Pinehurst, NC.

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Off Market Homes Near 44 Chestertown Dr

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