OFF MARKET

Off market apr 2024 for $1.4M

$1,698,370

Est. refi paymentEst. refi $6,420/mo

•

6,111

sq ft

4464 Bent Tree Farm Rd, Winston Salem, NC 27106

About this home

Total privacy surrounds this custom in-town estate on 3.75 acres in Bent Tree Farm! The winding driveway passes a charming 2-car detached garage (w/642-sq-ft apartment above) before arriving at the stone-accented, New England-style home; Elegant entry hall with grand staircase introduces an interior richly detailed w/fine woodwork & 10-foot ceilings on ML; Stunning kitchen w/island, 6-burner range, 2 dishwashers, built-in refrigerator & bar w/wine cooler & icemaker; Great room w/FP & arched windows; Spectacular 2-story study w/bar & balcony library; ML guest suite; Front/rear stairs lead to 2nd floor w/9-foot ceilings; Luxurious primary suite w/FP, spa-like bath & private balcony; Finished daylight/walkout LL with rec/play areas, bar & bath; Amazing salt-water pool/spa with rock formations and stone patios/sidewalks; Enormous screened porch & adjacent deck; Most windows replaced with Andersen Renewal; Control4 light, security & sound system; Sellers are licensed NC brokers.

Single-familyProperty Type

1990Year Built

3.75 acresLot Size

$278Est. Price/Sq.Ft.

4 car garageParking

Listed by Lloyd Dillon • Berkshire Hathaway HomeServices Carolinas Realty

Bought with Clare Fader • Fader Real Estate at ERA Live Moore

Redfin checked: 2 minutes ago

•Source:Triad MLS #1125373

Redfin Estimate

$1,698,370

$203K since sold in April 2024$71K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 58.5% higher than the average sale price ($1.07M) 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 SEP 28, 2026
$1,170,000
B
4 beds6 baths5,493 sq ft
3732 Kaismore Ct, Winston-Salem, NC 27106
SOLD JUL 30, 2026
$612,500
C
5 beds4.5 baths3,944 sq ft
4244 Saddlewood Forest Dr, Winston Salem, NC 27106
SOLD JUN 23, 2026
$1,200,000
D
4 beds6 baths5,900 sq ft
4141 Shattalon Dr, Winston Salem, NC 27106
SOLD OCT 28, 2025
$1,485,000
E
6 beds7 baths8,625 sq ft
3940 Beechridge Rd, 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

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$455,799

Est. take-home

List your home with Redfin and save $16,984

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,389/mo

Redfin rental estimate

List your home for rent

Market trends in 27106, NC

Last updated September 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

COMING SOON
$715,000
4 beds3.5 baths3,858 sq ft
4225 Holly Hill Ln, Winston Salem, NC 27106
OPEN SAT, 1PM TO 3PM
$769,000
3 beds3 baths2,834 sq ft
5435 Fern Bank Cir, Winston Salem, NC 27106
NEW 25 HRS AGO
$1,695,000
5 beds7 baths9,404 sq ft
4620 Cherryhill Ln, Winston Salem, NC 27106
$299,000
3 beds2 baths3,318 sq ft
3890 Whitehaven Rd, Winston Salem, NC 27106
$150,000
2 beds1 bath877 sq ft
4660 Tobacco St, Winston Salem, NC 27106
3D WALKTHROUGH
$970,000
4 beds5.5 baths5,016 sq ft
3736 Burbank Ln, Winston Salem, NC 27106
$440,000
3 beds2 baths2,147 sq ft
5275 Jacobs Way, Winston Salem, NC 27106
$445,000
3 beds2.5 baths1,967 sq ft
1264 Stadler Ridge Rd, Winston Salem, NC 27106
$558,000
4 beds4 baths3,787 sq ft
105 Ridgemere Ct, Winston Salem, NC 27106
$439,900
4 beds3 baths2,578 sq ft
4270 Lindsey Ln, Winston Salem, NC 27106
See all

Provided by Redfin

Sale history for 4464 Bent Tree Farm Rd

Year

Property tax

Land + Additions

Assessment*

2025

$16,316 (+2.8%)

$257,300 + $1,223,000

$1,480,300

2024

$15,864 (+6.8%)

$236,300 + $894,600

$1,130,900

2022

$14,858 (+1.8%)

$236,300 + $894,600

$1,130,900

2021

$14,591 (−2.1%)

$236,300 + $894,600

$1,130,900

2020

$14,907 (−0.7%)

$221,600 + $857,900

$1,079,500

2019

$15,015 (+5.3%)

$221,600 + $857,900

$1,079,500

2018

$14,259

$221,600 + $857,900

$1,079,500

2017

$14,259 (+17.6%)

$221,600 + $857,900

$1,079,500

2016

$12,125 (+1.5%)

$221,600 + $857,900

$1,079,500

2015

$11,941 (+3.1%)

$221,550 + $699,808

$921,358

2014

$11,580

$221,550 + $699,808

$921,358

Tax history for 4464 Bent Tree Farm Rd

Year

Property tax

Land + Additions

Assessment*

2025

$16,316 (+2.8%)

$257,300 + $1,223,000

$1,480,300

2024

$15,864 (+6.8%)

$236,300 + $894,600

$1,130,900

2022

$14,858 (+1.8%)

$236,300 + $894,600

$1,130,900

2021

$14,591 (−2.1%)

$236,300 + $894,600

$1,130,900

2020

$14,907 (−0.7%)

$221,600 + $857,900

$1,079,500

2019

$15,015 (+5.3%)

$221,600 + $857,900

$1,079,500

2018

$14,259

$221,600 + $857,900

$1,079,500

2017

$14,259 (+17.6%)

$221,600 + $857,900

$1,079,500

2016

$12,125 (+1.5%)

$221,600 + $857,900

$1,079,500

2015

$11,941 (+3.1%)

$221,550 + $699,808

$921,358

2014

$11,580

$221,550 + $699,808

$921,358

*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

Stories

Lot width

—

Lot depth

—

Lot size

3.75 Acres

Year renovated

1990

Sq. Ft.

6,246

Year built

1990

Style

Single Family Residential

County

Forsyth County

APN

6806363845

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

Property details

Parking

Parking / Garage Information
# of Garage Spaces: 4
Garage Description: Attached Garage, Detached Garage
Parking Features: Driveway, Garage, Circular Driveway, Garage Door Opener, Attached, Detached

Interior

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (1/2): 2

Basement Information
Basement YN: Yes
Has Basement
Basement: Finished, Basement, Crawl Space
Basement Area: 1124

Room Information
# of Rooms: 13

Interior Features
Attic Description: Eave Storage, Floored Attic, Permanent Stairs
Energy Features: Insulated Windows
Flooring: Carpet, Tile, Wood
Interior Features: Great Room, Arched Doorways, Built-in Features, Ceiling Fan(s), Dead Bolt(s), Kitchen Island, Sauna, Separate Shower, Solid Surface Counter, Vaulted Ceiling(s), Wet Bar

Exterior

Exterior Features
Exterior Features: Sprinkler System
Other Equipment: Irrigation Equipment
Fencing: Fenced, Privacy

Pool Information
Pool Features: In Ground, Private

Guest House Information
Has Second Living Quarters
Attached: No
# of Rooms: 1
# of Baths (Full): 1

Lot Information
Lot Number: 12
Lot Features: City Lot, Partially Wooded, Subdivided, Sloped
Lot Size Acres: 3.75
Lot Size Dimensions: 120 x 354 x 652 x 85 x 713
Miscellaneous: Great Room

Land Information
Land Description: Fence(s), Partially Wooded, Subdivision, Sloping
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Stick/Site Built
Structure Type: House
Built Information: Existing
Year Built: 1990
# of Fireplaces: 3
Fireplace Features: Gas Log, Basement, Great Room, Primary Bedroom
Appliances: Microwave, Built-in Refrigerator, Dishwasher, Disposal, Double Oven, Range, Gas Cooktop, Ice Maker, Range Hood, Gas Water Heater
Laundry Features: Dryer Connection, Main Level, Washer Hookup
Security Features: Security Lights, Security System, Carbon Monoxide Detector(s), Smoke Detector(s)

Building Information
Building Area Total: 6,111
Foundation Details: Slab
Levels: Two
Construction Materials: Brick, Stone, Vinyl Siding, Wood Siding

Financial

Tax Information
Tax Annual Amount: $15,140.49

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Gas

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

Location

HOA Information
Association: Winston-Salem
Association YN: Yes
Association Fee: $930
Association Fee Frequency: Annually

Location Details
Directions: Robinhood Road West past intersection with Shattalon Drive; Take second road on the right -- Cherryhill Lane; Go to stop sign and turn right on Beechridge Road; Go to stop sign and turn left on Bent Tree Farm Road; 4464 is first house on the left.

Community Information
Subdivision Name: Bent Tree Farm

Public facts

Beds: 5
Baths: 6.0
Sq. Ft.: 6,246
Stories: 2.0
Lot Size: 3.75 acres
Style: Single Family Residential
Year Built: 1990
Year Renovated: 1990
County: Forsyth County
APN: 6806363845

Home facts updated by county records on Aug 17, 2026

Around this home

Schools

Jefferson Elementary

Public PreK-5 • Assigned • 0.3mi

9/10

Jefferson Middle

Public 6-8 • Assigned • 1.4mi

7/10

Mount Tabor High

Public 9-12 • Assigned • 1.6mi

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, 17 days in 30 years

3/10 Wind Factor

6% 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

$1.61M – $1.95M

Reach more buyers when you sell with Redfin. Save up to $16,984 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

$334,900

3 beds1.5 baths1,640 sq ft

575 Alpine Rd, Winston Salem, NC 27104

$377,700

4 beds3 baths2,551 sq ft

590 N Peace Haven Rd, Winston Salem, NC 27104

$399,000

4 beds2.5 baths1,891 sq ft

4816 Welwyn Rd, Winston Salem, NC 27104

OPEN SUN, 2PM TO 4PM3D WALKTHROUGH

$376,900

3 beds2.5 baths2,027 sq ft

256 Brooks Landing Dr, Winston Salem, NC 27106

$379,000

3 beds2 baths2,088 sq ft

139 Brooks Landing Dr, Winston Salem, NC 27106

NEW 22 HRS AGO

$429,000

3 beds2.5 baths2,413 sq ft

821 Chancy Ln, Winston Salem, NC 27104

New listings for sale in 27106

COMING SOON

$715,000

4 beds3.5 baths3,858 sq ft

4225 Holly Hill Ln, Winston Salem, NC 27106

OPEN SAT, 1PM TO 3PM

$769,000

3 beds3 baths2,834 sq ft

5435 Fern Bank Cir, Winston Salem, NC 27106

NEW 25 HRS AGOVIDEO TOUR

$1,695,000

5 beds7 baths9,404 sq ft

4620 Cherryhill Ln, Winston Salem, NC 27106

$299,000

3 beds2 baths3,318 sq ft

3890 Whitehaven Rd, Winston Salem, NC 27106

$150,000

2 beds1 bath877 sq ft

4660 Tobacco St, Winston Salem, NC 27106

3D WALKTHROUGH

$970,000

4 beds5.5 baths5,016 sq ft

3736 Burbank Ln, Winston Salem, NC 27106

$440,000

3 beds2 baths2,147 sq ft

5275 Jacobs Way, Winston Salem, NC 27106

$445,000

3 beds2.5 baths1,967 sq ft

1264 Stadler Ridge Rd, Winston Salem, NC 27106

$558,000

4 beds4 baths3,787 sq ft

105 Ridgemere Ct, Winston Salem, NC 27106

Home values near 4464 Bent Tree Farm Rd

Data from public records.

Address	Redfin Estimate
4441 Bent Tree Farm Road, Winston Salem, NC 4 Beds \| 5.5 Baths \| 5164 Sq. Ft.	$1,326,612
4457 Bent Tree Farm Road, Winston Salem, NC 5 Beds \| 4.5 Baths \| 5287 Sq. Ft.	$1,064,996

Address	Redfin Estimate
4473 Bent Tree Farm Road, Winston Salem, NC 4 Beds \| 5.5 Baths \| 5469 Sq. Ft.	$1,118,977
4465 Bent Tree Farm Road, Winston Salem, NC 4 Beds \| 5 Baths \| 4863 Sq. Ft.	$1,283,153

Address	Redfin Estimate
4472 Bent Tree Farm Road, Winston Salem, NC 5 Beds \| 4.5 Baths \| 6345 Sq. Ft.	$1,324,639
4449 Bent Tree Farm Road, Winston Salem, NC 4 Beds \| 5.5 Baths \| 5760 Sq. Ft.	$1,371,969

Property information provided by Triad MLS when last listed in 2023. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

27103 homes for sale
27104 homes for sale
27106 homes for sale
27023 homes for sale
27012 homes for sale

Houses for rent in Winston-Salem	Agents near me	Asheville, NC homes for sale	Winston-Salem Housing Market
Houses for sale near me	Charlotte, NC homes for sale	Apex, NC homes for sale
Land for sale near me	Raleigh, NC homes for sale	Greensboro, NC homes for sale
Open Houses near me	Cary, NC homes for sale	Winston-Salem Property Records
Condos for sale near me	Durham, NC homes for sale	NC New Listings

High Point homes for sale
Kernersville homes for sale
Greensboro homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 27106, NC

Sale history for 4464 Bent Tree Farm Rd

Tax history for 4464 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 4464 Bent Tree Farm Rd

More real estate resources