51 Chestertown Dr

Off Market

51 Chestertown Dr

Southern Pines NC 28374

5382 sq. ft.

78408 sq. ft.

Single-Family

Last sold for $1,350,000

Leigh Amigo, last sold this property on 20 November 2025 after 888 days on market.

Overview

Welcome home to the prestigious Forest Creek Golf Club. 51 Chestertown Drive boasts over 5,300 square feet of living space on a 1.79-acre lot with unobstructed golf views of the 3rd fairway on the South Course. Built in 2002, this three-level residence includes an elevator and a 3-car garage. On the main floor, you'll enjoy abundant natural light throughout the open kitchen, living, and dining space. A primary retreat welcomes you home at the end of each day—a dedicated office, walk-in pantry, and guest bedroom round out the main floor. Two bedrooms upstairs, a loft, and a dedicated second laundry offer privacy for kids and guests alike. Downstairs, find an epic walk-out basement with a well-appointed bar, a game area, space to lounge, an additional bedroom, and bathrooms, as well as flex space. Some recent updates include full home theater wiring complete with Sonos speakers, a full home mesh system with backup power, and additional finished heated and cooled attic space off the third floor. With access to two elite Tom Fazio golf courses and resort-style living, don't miss your opportunity to view this one-of-a-kind property.

Features

4 bedrooms

7 bathrooms

3 carspaces

3 garage spaces

5382 sq. ft. floor area

78408 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Southern Pines over the last 12 months, the estimated median property value of 51 Chestertown Dr is $806.86k.

Median value

$806.86k

Estimated value range

$300k - $3.19m

Median days on market

Estimated value trend

11%

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 51 Chestertown Dr

2025

Sold

$1,350,000

20 Nov 2025 by Leigh Amigo, of Keller Williams Realty

2020

Sold

$603,900

11 Nov 2020 by KENNETH SHAW, of DEVELOPMENT MARKETING 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 4 bedroom single-family properties in Southern Pines

In the last 12 months, 183 four-bedroom single-family properties similar to 51 Chestertown Dr, have been sold.

This represents a 6% increase in four-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)

(382 reviews)

Get a market analysis

Colleen Schreiber

(18 reviews)

Get a market analysis

Cherry Amanatidis

at PREMIER REAL ESTATE OF THE SANDHILLS LLC

(63 reviews)

Get a market analysis

James Hurt

(4 reviews)

Get a market analysis

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 (382 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

View profile

Cherry Amanatidis

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