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$449,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,140 Sq. Ft.
  • 0.37 Acres
  • 2 Car Garage
  • Updated 9 hours ago
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First time offering for sale since custom construction in 2005! Wonderfully maintained, move-in ready one-level home w/ bonus room in the desirable, convenient Prestwick neighborhood. Thoughtfully designed with an easy-flowing floor plan, generously sized rooms, upgraded kitchen cabinetry w/ granite countertops. The spacious primary suite offers a relaxing retreat with dual vanities, separate soaking tub/shower, and two large walk-in closets. Split-bedroom design provides excellent privacy for family and guests. Versatile room just off the kitchen can serve as a formal dining room, sunroom, or flexible living space. The inviting great room features a vaulted ceiling and gas fireplace, creating a warm and welcoming gathering space. The covered porch is perfect for entertaining or relaxing while overlooking the spacious backyard. New roof Spring 2026 and new carpet on the main level September 2026. A beautifully cared-for home ready for its next chapter! See Agent Only.

Full Property Details for 5299 Jacobs Way

General

  • Price: $449,900
  • HOA FEE: $13/month
  • HOA FEE FREQ.: Annually
  • Taxes: $4,944
  • Status: Active
  • Type: Single Family
  • Source: Triad_MLS
  • MLS ID: 1238807
  • Updated: Today (10/13/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 9
  • Interior Features: Ceiling Fan(s), Dead Bolt(s), Soaking Tub, Separate Shower, Solid Surface Counter
  • Number of Fireplaces: 1
  • Fireplace(s): Gas Log, Great Room
  • Appliances: Microwave, Dishwasher, Disposal, Range, Gas Water Heater
  • Flooring: Carpet, Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 3
  • 1st/Main Floor Primary: Yes

Other Rooms

  • Laundry: Dryer Connection, Main Level, Washer Hookup

Additional Information

  • Security/Safety: Security System

Exterior

  • Patio/Terrace: Yes

Parking

  • Garage Description: Attached Garage
  • Garage Spaces: 2
  • Parking Features: Garage, Driveway, Garage Door Opener, Attached

Location

  • County: Forsyth
  • Subdivision: Prestwick
  • Driving Directions: Robinhood Rd to left onto Norman Rd., Left onto Tallison, Right onto Huntscroft Lane, Right onto Fairburn Dr, m Right onto Prestwick Crossing, Left onto Jacobs Way, house on the corner.
  • City Limits: Yes

School Information

  • Elementary School: Call School Board
  • Middle School: Call School Board
  • High School: Call School Board

Community

  • Association: Yes
  • Assoc. Name: Prestwick HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Forced Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Traditional
  • Exterior Const.: Brick, Vinyl Siding
  • Stories/Levels: One
  • Square Feet: 2,140
  • Heated/Cooled: 2,140 Sq. Ft.
  • Year Built: 2005

Additional Structures

  • Other Structures: Storage

Lot Features

  • Lot Size (Acres): 0.37
  • Lot Dimensions: 71 x 154 x 107 x 94 x 96
  • Road Maintenance: Public Maintained Road
  • Lot Features: City Lot, Cleared, Corner Lot, Subdivided
  • Fencing (Description): None

Financial Considerations

  • Price Per Acre: $1,215,945.9459
  • Association Fee: $150
  • Assoc Fee Freq.: Annually
  • Tax Amount: $4,944.61
  • Terms: Cash, Conventional, FHA, VA Loan

Disclosures and Reports

  • Special Conditions: Owner Sale
  • Deed Restrictions: Yes
  • Lot Number: 29

Listed by Berkshire Hathaway HomeServices Carolinas Realty

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Listing agent

— 5299 Jacobs Way —

  • Berkshire Hathaway HomeServices Carolinas Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5299 Jacobs Way

School District:Forsyth County Schools
NameGradesDistance
Jefferson Elementary, Winston-Salem, NC
4000 Jefferson School Lane, Winston-Salem, NC 27106
PK-51.1 mi
Jefferson Middle
3500 Sally Kirk Road, Winston-Salem, NC 27106
6-80.6 mi
Mount Tabor High
342 Petree Road, Winston-Salem, NC 27106
9-121.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5299 Jacobs Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/13/2026
Listed
$449,900
93.09%
MLS
9/01/2005
Sold
$233,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5299 Jacobs Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,768
20%
$432,600
53%
2024
$3,960
5%
$282,300
—
2023
$3,779
4%
$282,300
—
2021
$3,642
-2%
$282,300
—
2022
$3,709
2%
$282,300
10%
2021
$3,642
2%
$257,400
—
2019
$3,580
5%
$257,400
—
2018
$3,400
—
$257,400
—
2017
$3,400
6%
$257,400
6%
2016
$3,193
2%
$242,600
—
2015
$3,144
3%
$242,600
—
2014
$3,049
1%
$242,600
—
2013
$3,025
—
$242,600
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Berkshire Hathaway HomeServices Carolinas Realty

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5299 Jacobs Way, Winston-Salem, NC 27106 (MLS# 1238807) is a Single Family property with 3 bedrooms and 2 full bathrooms. 5299 Jacobs Way is currently listed for $449,900 and was received on October 13, 2026. Want to learn more about 5299 Jacobs Way? Do you have questions about finding other Single Family real estate for sale in Reynolda? You can browse all Reynolda real estate or contact a Coldwell Banker agent to request more information.

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