5499 Winchester Road

4,909 Sq. Ft.
$188 / Sq. Ft.
4,909
Sq. Ft.
$188
per Sq. Ft.

Description

Welcome to a beautifully preserved estate where timeless elegance offers flexibility for commercial or residential use. It's perfect for a family estate, generational living or a grand event venue! Enjoy the main residence, where each bedroom has it's own private bath, a beautifully updated kitchen boasting marble counter tops with custom cabinetry, updated electrical and plumbing, original hardwood floors through out, all with a NEW copper and shingle roof. The charming original cottage offers a...Welcome to a beautifully preserved estate where timeless elegance offers flexibility for commercial or residential use. It's perfect for a family estate, generational living or a grand event venue! Enjoy the main residence, where each bedroom has it's own private bath, a beautifully updated kitchen boasting marble counter tops with custom cabinetry, updated electrical and plumbing, original hardwood floors through out, all with a NEW copper and shingle roof. The charming original cottage offers a full bath & kitchenette, with herringbone brick floors. Even the oversized 3 car garage provides apartment space, all set on expansive land. A rare opportunity. Schedule your private showing today!
  1. Listed by Susan Gatlin • Leading Edge Real Estate Group
    P: (256)-424-5378 C: (256)-424-5378 susangatlin1@outlook.com

Property Details for 5499 Winchester Road

Subdivision Name
N/A
Waterfront
No
LISTING UPDATED: 07/01/2026 02:53 PM

Property Details for 5499 Winchester Road

StatusActive
MLS #3255903
Days on Market1
Taxes$2,033 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1960
Lot Size2.00 AC / 87,120 SF
CountyMadison County

Location

Listing Courtesy of Leading Edge Real Estate Group
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Building Information for 5499 Winchester Road

Stories3Year Built1960Building Size-Lot Size2.00 AC / 87,120 SF

Payment Calculator

$4,774 per month

30 year fixed, 6.36% Interest

Principal and Interest

$4,604

Property Taxes

$169

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 5499 Winchester Road

Summary
Location and General Information
  • Directions: From I-565 East, turn LEFT on Moores Mill, RIGHT on Winchester Rd & continue straight into New Market.Home is on the LEFT, corner of Winchester Rd & New Market Rd.
  • Elementary School: New Market School
  • High School: Buckhorn High School
  • Levels: Three Or More
  • Living Area Source: Professional Measurement
  • Living Area Units: Square Feet
  • Middle Or Junior School: Buckhorn Middle School
  • Mlg Can View: Yes
Parking
  • Garage Spaces: 3.00
  • Parking Features: Detached
  • Parking Total: 3.00
Taxes and HOA Information
  • Condo Coop Association YN: No
Property
Building Information
  • Above Grade Finished Area Source: Professional Measurement
  • Above Grade Finished Area Units: Square Feet
  • Below Grade Finished Area Source: Professional Measurement
  • Below Grade Finished Area Units: Square Feet
  • Building Area Source: Professional Measurement
  • Building Area Units: Square Feet
  • Flooring: Wood, Tile
Lot Information
  • Lot Size Source: Assessor
  • Lot Size Units: Acres
  • Parcel Number: 0209324001001000
  • Lot Size Area: 2.0
Property and Assessments
  • Construction Materials: Wood Siding
  • Documents Count: 0
  • New Construction: No
  • Possession: Close Of Escrow
  • Property Attached: No
  • Senior Community: No
  • Stories: 3
  • Year Built Details: Existing
Utilities
  • Basement: Crawl Space
  • Cooling: Central Air, Electric
  • Cooling: Yes
  • Heating: Central, Propane
  • Heating: Yes
  • Sewer: Septic Tank
  • Utilities: Electricity Available, Water Available
  • Water Source: Private
Interior and Exterior Features
Interior Features
  • Appliances: Double Oven
Bedroom Information
  • Main Level Beds: 0
Exterior Features
  • Attached Garage: No
  • Covered Spaces: 3.00
  • Exterior Features: No Dock
  • Garage: Yes
  • Pool Private: No
  • View YN: No
Room Information
Room 1
  • Room Dimensions: 14x15
  • Room Features: Suite
  • Room Type: Bedroom 1
Room 2
  • Room Dimensions: 16x13
  • Room Type: Bedroom 2
Room 3
  • Room Dimensions: 16x13
  • Room Type: Bedroom 3
Room 4
  • Room Dimensions: 17x19
  • Room Type: Bedroom 4
Room 5
  • Room Features: Primary Bedroom
  • Room Type: Master Bathroom
Room 6
  • Room Dimensions: 13x15
  • Room Type: Den
Room 7
  • Room Dimensions: 15x15
  • Room Type: Dining Room
Room 8
  • Room Dimensions: 13x18
  • Room Features: Other
  • Room Type: Hobby Room
Room 9
  • Room Dimensions: 17x19
  • Room Type: Kitchen
Room 10
  • Room Dimensions: 16x13
  • Room Type: Living Room
Room 11
  • Room Dimensions: 16x14
  • Room Features: Library
  • Room Type: Other Room

Property History for 5499 Winchester Road

DateEvent & SourcePriceAppreciation
Jul 1, 2026

Listed (Active)

REALTRACS #3255903

$924,000—
Jul 1, 2026

Listed (Active)

REALTRACS #3255907

$924,000—
May 1, 2023

Sold

REALTRACS #2382229

$750,000—
DateEvent & SourcePrice
07/01/2026

Listed (Active)

REALTRACS #3255903

$924,000
07/01/2026

Listed (Active)

REALTRACS #3255907

$924,000
05/01/2023

Sold

REALTRACS #2382229

$750,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Schools near 5499 Winchester Road

This home is within Madison County School District.
Rating
School
Type
Grades
Distance
Public - PK to 6
Public - 7 to 8
Public - 9 to 12
Public - 3 to 5
Rating
School
Distance
New Market School
PublicPK to 6

Buckhorn Middle School
Public7 to 8

Buckhorn High School
Public9 to 12

Moores Mill Intermediate School
Public3 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

5499 Winchester Road is a single family home for sale in New Market, AL 35761. This listing's school district is Madison County School District. Nearby schools include New Market School, Buckhorn Middle School and Buckhorn High School. 5499 Winchester Road is a 4-bed, 5-bath, 4,909 sqft single family home built in 1960.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Leading Edge Real Estate Group

Based on information submitted to the MLS GRID as of 07/01/2026 02:53 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.