$3,697,700
- 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 HomeCurrently Off Market - Sold Dec 18, 2025 for $3,650,000 (24% above list price)
Home Value
Trulia Estimate
$3.7MSince 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
| Month | Estimated 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
-- mins to
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
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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 |
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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 |
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Cumulative Days on Market: 675 |
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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 |
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Price List Price: $2,950,000Price Per Sqft: $585/sqft |
Status Change & Dates Off Market Date: Mon Oct 20 2025Possession Timing: Close Of Escrow |
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MLS Status: Closed |
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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 |
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Building Area Building Area: 6244 Square Feet |
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HOA Name: CASHOA Phone: 910-295-3791HOA Fee Frequency (second): AnnuallyAssociation for this Listing: Mid Carolina Regional MLSHas an HOAHOA Fee: $1,890/Annually |
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Lot Area: 0.91 acres |
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Special Conditions: Standard |
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Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, VA Loan |
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Mls Number: 100500878Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square FeetShowing AttendedShowing Requirements: Appointment Only |
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HOA Amenities: Maintenance Common Areas,Maintenance Roads,Management,Security,Street Lights |
Price and Tax history
| Date | Event | Price |
|---|---|---|
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 |
Nov 29, 2024 Source: Hive MLS #100444998 | PriceChange | $2,950,000 Price decreased by 6% |
May 16, 2024 Source: Hive MLS #100444998 | Listed For Sale | $3,150,000 |
May 1, 2024 Source: Hive MLS #100413278 | ListingRemoved | |
Nov 6, 2023 Source: Hive MLS #100413278 | Listed For Sale | $3,150,000 |
Mar 1, 2023 Source: Hive MLS #100313219 | ListingRemoved | |
Apr 5, 2022 Source: Hive MLS #100313219 | Listed For Sale | $3,150,000 |
Feb 23, 2022 Source: Hive MLS #100313219 | ListingRemoved | |
Feb 21, 2022 Source: Hive MLS #100313219 | Listed For Sale | $3,150,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2024 | $8,737 | $1,370,440 |
Home facts updated by county records
Market trends in Pinehurst
Last updated August 2026
Avg. sale price
$598K
$7.92KMoM
Sale-to-List Price
98.0%
0.1%MoM
Price per sq ft
$249
$1MoM
Available listings
231
2MoM
Around this home
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.
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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 2026-09-13 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).

