OFF MARKET

Off Market Jun 2021 for $740K

$1,257,733

Est. refi paymentEst. refi $4,543/mo

•

5,411

sq ft

4424 Bent Tree Farm Rd, Winston Salem, NC 27106

About this home

MOTIVATED SELLERS! Beautifully updated on secluded 2.8-acre lot in prestigious Bent Tree! Gracious formal rooms. Master Bedroom Retreat w/private balcony! Gorgeous Chef’s Kit w/double islands, Wolf 6-Burner Professional Range, Butler’s Pantry & sun-filled breakfast area. Bright & airy sunrm w/FP, accented w/reclaimed wooden beams. Large family rm w/ fireplace opens onto UL patio overlooking private back yard. ML guest suite; LL playrm/den, guestrm & full BA.

Single-familyProperty Type

1999Year Built

2.8 acresLot Size

$232Est. Price/Sq.Ft.

2 car garageParking

Listed by Gail Sullivan • Berkshire Hathaway HomeServices Carolinas Realty

Listed by Mary Gettys Hardwick • Leonard Ryden Burr Real Estate

Bought with Amanda Pino • Coast 2 Coast Triad Home Team

Redfin checked: 3 minutes ago

•Source:Triad MLS #993926

Redfin Estimate

$1,257,733

$518K since sold in June 2021$6,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 32.9% higher than the average sale price ($947K) of 6 comparable homes.

SOLD JUN 15, 2026
$1,210,000
A
4 beds5 baths4,863 sq ft
4465 Bent Tree Farm Rd, Winston Salem, NC 27106
SOLD JUL 30, 2026
$612,500
B
5 beds4.5 baths3,944 sq ft
4244 Saddlewood Forest Dr, Winston Salem, NC 27106
SOLD JUN 22, 2026
$1,400,000
C
5 beds4.5 baths4,340 sq ft
1391 Pheasant Ln, Winston Salem, NC 27106
SOLD JUL 14, 2026
$890,000
D
4 beds4.5 baths5,218 sq ft
1513 Barrington Way Ct, Winston Salem, NC 27106
SOLD JUN 17, 2026
$817,000
E
4 beds4.5 baths4,443 sq ft
1004 Blakeford Ct, Winston Salem, NC 27106
SOLD JUN 22, 2026
$750,000
F
5 beds4.5 baths4,455 sq ft
3822 Ryan Way, Winston Salem, NC 27106

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Earn from this home

Sell

$652,454

Est. take-home

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Refinance

Est. cash available

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Rent

$3,403/mo

Redfin rental estimate

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Market trends in 27106, NC

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.0%

+0.0% MoM

Median sale price

$397K

$7K MoM

Avg. days on market

38d

3 days MoM

Recently sold homes

183

4 MoM

New listings for sale

NEW 12 HRS AGO
$1,325,000
5 beds4.5 baths5,312 sq ft
5330 Summer Hill Ln, Winston Salem, NC 27106
NEW 18 HRS AGO
$189,000
2 beds3 baths2,338 sq ft
803 Aspen Trl, Winston Salem, NC 27106
NEW 25 HRS AGO
$749,000
4 beds4.5 baths4,586 sq ft
810 Poplar Grove Rd, Winston Salem, NC 27106
$325,000
3 beds2 baths1,720 sq ft
5059 Ramillie Run, Winston Salem, NC 27106
OPEN SUN, 2PM TO 4PM
$389,900
4 beds2.5 baths1,890 sq ft
4219 Honeysuckle Vine Dr, Winston Salem, NC 27106
$252,000
3 beds2 baths1,564 sq ft
5750 Harpers Ferry Rd, Winston Salem, NC 27106
$250,000
3 beds2.5 baths537 sq ft
2618 Speas Rd, Winston Salem, NC 27106
$279,900
3 beds2 baths1,855 sq ft
3915 Avera Ave, Winston Salem, NC 27106
$738,000
5 beds4 baths3,835 sq ft
4610 Century Oaks Ln, Winston Salem, NC 27106
$215,000
3 beds1.5 baths1,001 sq ft
4154 Edgeware Rd, Winston Salem, NC 27106
See all

Provided by Redfin

Sale history for 4424 Bent Tree Farm Rd

Date

Event

Price

Triad MLS #993926

Jun 2, 2021

Sold

$740,000

$137/sq ft

May 6, 2021

Pending

—

Apr 8, 2021

Contingent

—

Sep 11, 2020

Listed

$799,000

$148/sq ft

Triad MLS #1

Aug 3, 2020

Price Changed

$799,000

$148/sq ft

Jun 10, 2020

Price Changed

$849,000

$157/sq ft

Mar 24, 2020

Price Changed

$859,900

$159/sq ft

Nov 13, 2019

Price Changed

$875,000

$162/sq ft

Aug 6, 2019

Price Changed

$889,900

$164/sq ft

May 28, 2019

Price Changed

$920,000

$170/sq ft

Public Records

Mar 21, 2013

Sold

$870,000

$161/sq ft

Triad MLS #661381

Mar 21, 2013

Sold

$869,900

$161/sq ft

Jan 10, 2013

Listed

$859,900

$159/sq ft

+11

Stunning custom built Tuscan Inspired Italian Country Villa located on exquisite, secluded 2.8 acre site in prestigious Bent Tree Farm! Gracious formal areas; fabulous gourmet Kitchen for the serious chef is highlighted by a handsome island & Spanish gates leading to Great Room with fireplace with acanthus detailed mantel! Glorious Sunroom accented with re-claimed wood beams; Upper and Lower Patios overlook the private, lushly landscaped yard! Extraordinary in every way!

Public Records

Apr 18, 1994

Sold

$150,000

$28/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$12,698 (+4.5%)

$245,000 + $907,100

$1,152,100

2024

$12,157 (+6.8%)

$225,000 + $641,600

$866,600

2022

$11,385 (+1.8%)

$225,000 + $641,600

$866,600

2021

$11,181 (+0.5%)

$225,000 + $641,600

$866,600

2020

$11,122 (−0.7%)

$211,000 + $594,400

$805,400

2019

$11,202 (+5.3%)

$211,000 + $594,400

$805,400

2018

$10,639

$211,000 + $594,400

$805,400

2017

$10,639 (+28.4%)

$211,000 + $594,400

$805,400

2016

$8,285 (+1.5%)

$211,000 + $594,400

$805,400

2015

$8,159 (+3.1%)

$211,000 + $418,557

$629,557

2014

$7,912

$211,000 + $418,557

$629,557

Tax history for 4424 Bent Tree Farm Rd

Year

Property tax

Land + Additions

Assessment*

2025

$12,698 (+4.5%)

$245,000 + $907,100

$1,152,100

2024

$12,157 (+6.8%)

$225,000 + $641,600

$866,600

2022

$11,385 (+1.8%)

$225,000 + $641,600

$866,600

2021

$11,181 (+0.5%)

$225,000 + $641,600

$866,600

2020

$11,122 (−0.7%)

$211,000 + $594,400

$805,400

2019

$11,202 (+5.3%)

$211,000 + $594,400

$805,400

2018

$10,639

$211,000 + $594,400

$805,400

2017

$10,639 (+28.4%)

$211,000 + $594,400

$805,400

2016

$8,285 (+1.5%)

$211,000 + $594,400

$805,400

2015

$8,159 (+3.1%)

$211,000 + $418,557

$629,557

2014

$7,912

$211,000 + $418,557

$629,557

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

121,967

Year renovated

1999

Sq. Ft.

5,411

Year built

1999

Style

Single Family Residential

County

Forsyth County

APN

6806561812

Parking Spaces

Basement

Yes

Accessible

Yes

HOA Dues

$75 /month

Garage

Yes

Features

Views, Green, Pool

Last updated by owner on Nov 5, 2022.

Property details

Parking

Parking / Garage Information
# of Garage Spaces: 2
Garage Description: Attached Garage
Parking Features: Driveway, Garage, Paved, Garage Door Opener, Attached

Interior

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (1/2): 1

Basement Information
Basement YN: Yes
Has Basement
Basement: Finished, Unfinished, Basement
Basement Area: 1473

Room Information
# of Rooms: 14

Interior Features
Flooring: Carpet, Tile, Wood
Interior Features: Built-in Features, Ceiling Fan(s), Dead Bolt(s), Kitchen Island, Pantry, See Remarks, Separate Shower, Wet Bar

Exterior

Exterior Features
Exterior Features: Sprinkler System
Other Equipment: Irrigation Equipment

Pool Information
Pool Features: None

Lot Information
Lot Features: Partially Wooded
Lot Size Acres: 2.8
Miscellaneous: Cable

Land Information
Land Description: Partially Wooded
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Stick/Site Built
Structure Type: House
Built Information: Existing
Year Built: 1999
# of Fireplaces: 4
Fireplace Features: Gas Log, Den, Living Room, Playroom, See Remarks
Appliances: Microwave, Built-in Refrigerator, Dishwasher, Disposal, Exhaust Fan, Free-Standing Range, Gas Water Heater
Laundry Features: Dryer Connection, Laundry Room, Washer Hookup
Security Features: Security System, Smoke Detector(s)

Building Information
Building Area Total: 5,411
Levels: Two
Construction Materials: Stucco

Financial

Tax Information
Tax Annual Amount: $11,121.77

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Gas

Heating & Cooling
Cooling: Central Air, Zoned
Heating: Forced Air, Heat Pump, Electric, Natural Gas
Heating Fuel: Electric, Natural Gas

Location

HOA Information
Association: Winston-Salem
Association YN: Yes
Association Fee: $847
Association Fee Frequency: Annually

School / Neighborhood
Elementary School: Call School Board
Middle Or Junior School: Call School Board
High School: Call School Board

Location Details
Directions: Robinhood Rd, R on Shattalon, L into Bent Tree, house on left.

Community Information
Subdivision Name: Bent Tree Farm

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 5,411
Stories: 2.0
Parking Spaces: 2
Basement: Yes
Accessible: Yes
Lot Size: 2.8 acres
Style: Single Family Residential
Year Built: 1999
Year Renovated: 1999
County: Forsyth County
APN: 6806561812
HOA Dues: $75/month
Garage: Yes
Features: Views, Green, Pool

Home facts updated by owner on Nov 5, 2022

Around this home

Schools

Jefferson Elementary

Public PreK-5 • Assigned • 0.6mi

9/10

Jefferson Middle

Public 6-8 • Assigned • 1.1mi

7/10

Mount Tabor High

Public 9-12 • Assigned • 1.3mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 102° expected this year, 18 days in 30 years

4/10 Wind Factor

8% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Winston Salem, NC • 27106

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.1 hours in June and 5.1 hours in December, which is comparable to the U.S. average for solar exposure.

9.1 hrs

5.1 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.20M – $1.45M

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New listings for sale in 27106

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810 Poplar Grove Rd, Winston Salem, NC 27106

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5059 Ramillie Run, Winston Salem, NC 27106

OPEN SUN, 2PM TO 4PM

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4 beds2.5 baths1,890 sq ft

4219 Honeysuckle Vine Dr, Winston Salem, NC 27106

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2618 Speas Rd, Winston Salem, NC 27106

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Home values near 4424 Bent Tree Farm Rd

Data from public records.

Address	Redfin Estimate
4432 Bent Tree Farm Rd, Winston Salem, NC 6 Beds \| 5.5 Baths \| 8979 Sq. Ft.	$2,124,831
4409 Bent Tree Farm Rd, Winston Salem, NC 4 Beds \| 4 Baths \| 5695 Sq. Ft.	$1,508,956

Address	Redfin Estimate
4408 Bent Tree Farm Rd, Winston Salem, NC 5 Beds \| 4 Baths \| 5409 Sq. Ft.	$1,479,811
4401 Bent Tree Farm Rd, Winston Salem, NC 6 Beds \| 5 Baths \| 6256 Sq. Ft.	$1,372,988

Address	Redfin Estimate
4416 Bent Tree Farm Rd, Winston Salem, NC 5 Beds \| 4.5 Baths \| 5479 Sq. Ft.	$1,247,481
4417 Bent Tree Farm Rd, Winston Salem, NC 5 Beds \| 4.5 Baths \| 5756 Sq. Ft.	$1,323,492

Property information provided by Triad MLS when last listed in 2020. This data may not show owner updates. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 27106, NC

Sale history for 4424 Bent Tree Farm Rd

Tax history for 4424 Bent Tree Farm Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 27106

Home values near 4424 Bent Tree Farm Rd

More real estate resources