45 Chestertown Drive

Off Market

45 Chestertown Drive

Southern Pines NC 28374

6244 sq. ft.

39640 sq. ft.

Single-Family

Last sold for $3,650,000

Lin Hutaff, last sold this property on 18 December 2025 after 1353 days on market.

Overview

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.

Features

5 bedrooms

6 bathrooms

2 carspaces

2 garage spaces

6244 sq. ft. floor area

39640 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Southern Pines over the last 12 months, the estimated median property value of 45 Chestertown Drive is $1.09m.

Median value

$1.09m

Estimated value range

$425k - $3.65m

Median days on market

Estimated value trend

49%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Southern Pines. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 45 Chestertown Drive

2025

Sold

$3,650,000

18 Dec 2025 by Lin Hutaff, of Lin Hutaff's Pinehurst Realty Group

Happy sellers in Southern Pines

76%

76% of sellers in Southern Pines reported that their sale price either exceeded or met their price expectations.

Southern Pines stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 15 reviews in Southern Pines over the last 12 months.

Local market activity for 5 bedroom single-family properties in Southern Pines

In the last 12 months, 45 five-bedroom single-family properties similar to 45 Chestertown Drive, have been sold.

This represents a 32% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Southern Pines for a market analysis.

Tammy O Lyne

at KELLER WILLIAMS REALTY (PINEHURST)

(383 reviews)

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Colleen Schreiber

(18 reviews)

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Cherry Amanatidis

at PREMIER REAL ESTATE OF THE SANDHILLS LLC

(63 reviews)

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James Hurt

(4 reviews)

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Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Southern Pines

Tammy O Lyne

Sellers who recommend Tammy O Lyne have praised them for being local expert, responsive, clear communication, reliable, stress-free process, supportive, and well-prepared

5 (383 reviews)
6 Reviews in Southern Pines
7 Sales in Southern Pines

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Colleen Schreiber

Colleen Schreiber is a recommended agent for Southern Pines. They have 4 local sales and collected 5 local reviews across the last 12 months.

5 (18 reviews)
5 Reviews in Southern Pines
4 Sales in Southern Pines

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Cherry Amanatidis

Sellers who recommend Cherry Amanatidis have praised them for being local expert, responsive, dedicated, clear communication, friendly, supportive, and patient