14 Winfield Pl, Jackson, TN 38305
Property image
Property image
FOR SALE

$599,000

Original price: $629,000
  • 4 Beds
  • 2.5 Baths
  • 4,108 sqft

14 Winfield Pl, Jackson, TN 38305

Est. Mortgage $3,716/mo*
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Home Highlights

Single-Family Home
Built in 1999
$146/sqft
3 Car Garage
HOA $125/mo

Local Information

  • Map ViewExplore the area around 14 Winfield Pl.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Inviting porchesMain-level primary suiteThree-car garageRecently renovated bathThree generously sized bedroomsLarge closets
Within the gates of Winfield Place, one of Jackson's most coveted enclaves, this distinguished residence blends timeless elegance, exceptional privacy, and a premier location just moments from Jackson Country Club and its championship golf course. Thoughtfully designed for sophisticated living, the home features a main-level primary suite with recently renovated bath, a chef's kitchen and a striking great room with custom built-ins and fireplace. A grand staircase leads to three generously sized bedrooms, each offering large closets and new flooring. A massive bonus room offers remarkable versatility as a theater, game room, executive office, fitness studio, or private retreat. Outdoors, manicured grounds, inviting porches, and a three-car garage enhance the property's appeal. The quiet street, mature landscaping, and effortless access to golf, dining, and recreation create a lifestyle defined by comfort and distinction. Experience the enduring allure of Winfield Place—where timeless luxury is always in style.
Last check for updates: about 11 hours ago
Listing courtesy of Tori Wilkerson
Hickman Realty Group Inc.-Jack, (731) 664-1006
Source: CWTAR, MLS#2602864
Also Listed on CWTAR.

Home Details for 14 Winfield Pl

Interior Features

Interior Details
Number of Rooms: 13Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Bonus Room, Breakfast Nook, Dining Room, Foyer, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 1Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 4108 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Fiber Optic Available, Natural Gas Connected, Water Connected, Underground UtilitiesAppliances: Dishwasher, Disposal, Down Draft, Gas Cooktop, Gas Water Heater, Refrigerator, Stainless Steel Appliance(s)DishwasherDisposalLaundry: Electric Dryer Hookup,Laundry Room,Main Level,Sink,Washer HookupRefrigerator
Fireplace & Spa
Fireplace: Gas Log, Great RoomHas a FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Blinds, Wood FramesFlooring: Carpet, Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility
Number of Stories: 1Levels: TwoFloors: Carpet, Ceramic Tile, Hardwood
View
No View
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Patio / Porch: Covered, Front Porch, PatioExterior: Rain GuttersFoundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Has a GarageHas an Attached GarageParking Spaces: 5Parking: Garage Door Opener,Garage Faces Side
Frontage
Road Frontage: Private RoadResponsible for Road Maintenance: Private Maintained RoadNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Days on Market: 96

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: BrickNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 055C E 018.00

Price & Status

Price
List Price: $599,000Price Per Sqft: $146
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: Active

Location

Direction & Address
City: JacksonCommunity: Winfield Place
School Information
Elementary School District: Jackson Madison Consolidated District

Agent Information

Listing Agent
Listing ID: 2602864

HOA

Has an HOAHOA Fee: $125/Monthly

Listing Info

Special Conditions: Standard

Miscellaneous

Mls Number: 2602864

Around this home

What Locals Say about Jackson

At least 428 Trulia users voted on each feature.

  • 88 % Say car is needed

  • 82 % Say yards are well-kept

  • 81 % Say parking is easy

  • 69 % Say there's holiday spirit

  • 68 % Say it's dog friendly

  • 62 % Say kids play outside

  • 60 % Say it's quiet

  • 51 % Say neighbors are friendly

  • 47 % Say people would walk alone at night

  • 46 % Say they plan to stay for at least 5 years

  • 46 % Say streets are well-lit

  • 41 % Say there's wildlife

  • 32 % Say there are sidewalks

  • 28 % Say it's walkable to grocery stores

  • 24 % Say there are community events

  • 24 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Brenda Cole-Sheffield
    "Keep the yards clean and dogs not running around "
    0
    Flag
  • Brenda Cole-Sheffield
    "No area for dogs to walk really "
    0
    Flag
  • Brenda Cole-Sheffield
    "It’s no sidewalk on my street to walk a dog but it’s a park near for the dogs to run and play. Street too busy for a dog to play "
    0
    Flag
  • Sarah L Gowdy
    "It’s convenient. Shopping close by. There is several different restaurants to choose from. The neighborhood is quiet."
    0
    Flag
  • Shaska S.
    "It’s a great neighborhood with friendly neighbors,I’ve had no problem with anyone! The apartments are so nice from the paint job ~to the beautiful floors,Brand new Shiny Appliances as well… Really enjoyable and peaceful environment 💛"
    0
    Flag
  • Kristagrace
    "I’ve lived here for three years and love the area and the neighbors. It is close to shopping, a Kroger grocery store, a Walgreens and a gas station. It is also close access to the interstate. "
    12
    Flag
  • Buddie P
    "Jackson City Beautiful award winner 2023. Love the neighborhood. Well kept lawns. Great walking area. Near Park."
    3
    Flag
  • Ariel Flores
    "Feel free and good safe and I love this place so much and a like the weather is beautiful and perfect for my kids "
    0
    Flag
  • Megan Masga
    "Food trucks events and ymca, parks are huge. Nothing too much to do around here. City is developing rapidly"
    1
    Flag
  • Tonya Chatman
    "Dogs need to be kept on a leash and kept in a fenced backyard. People should pickup after their dogs Z"
    3
    Flag
  • Ohoward789
    "The cleanliness. I like peace of mind that I have knowing I can walk around. I really like Jackson. It is a nice place to live. Everything is nearby. The attractions are in close proximity of my home."
    20
    Flag
  • Sam
    "Quiet, mostly retired people with most people keeping up their homes and maintaining their lawns. Convenient to Lowe’s and WalMart and many fast food restaurants. Not many opportunities for fine dining but there are two locations within 3 miles that are lower than fine dining but not chain restaurants. "
    2
    Flag
  • Lrlytle
    "Fabulous neighbors and neighborhood, in general, until flippers and slum lords started buying properties in the area, Now, the neighborhood is not nearly as safe or serene as it once was. They are slowly destroying it for everyone. "
    8
    Flag
  • Lrlytle
    "Good neighbors who watch out for pets and keep an eye out for neighborhood pets, as well as children."
    0
    Flag
  • Larendamitchell
    "They like everything so there dogs can run and play. There’s always other dogs there too. Everyone seems friendly. Great place."
    8
    Flag
  • Joy C.
    "Restaurants specific for this area, farmers market, fitness gym, amphitheater, and nice size dog park. "
    2
    Flag
  • Syd m
    "North Jackson is better than South Jackson get to the best schools Sacred Heart is one of a great school here off of McClellan"
    0
    Flag
  • LT
    "This is a very quiet neighborhood and I enjoy it very much. I have lived here 3 years and plan to stay for a while. "
    0
    Flag
  • Marebare11856
    "A good neighborhood but there are woods behind that some use for 4 wheelers and target practice. This is the worst of it though."
    0
    Flag
  • Buckster
    "I’ve lived in this neighborhood for 10 years now, and we love it. Very close knit community and friendly neighbors. It’s a small town feel for a bigger community. "
    0
    Flag
  • Feliciapharmer
    "I've lived in Jackson my whole life. I live in South Jackson and prefer it more than North Jackson. Out south does need more apartment complexes and entertainment places like movies and bowling. "
    0
    Flag
  • Tlewis38301
    "Wright’s Mill is a great place to live if you have a family. It’s close to everything that’s fun to do and to eat. "
    0
    Flag
  • Keturah R.
    "It is a very nice place to live you would love it if you was to live here the landlord is sweet to deal with as long as you follow the rules "
    7
    Flag
  • Kate
    "Traffic is not good. The bypass construction sucks. I don’t work in Jackson but the commute in the mornings is rough if you hit rush hour. The bypass construction has caused a lot of different problems. Perhaps when they get it done it’ll be better. "
    5
    Flag
  • Marebare11856
    "We are one of the few neighborhoods that still has trick or treating door to door. There is a park within walking distance that has softball fields, tennis courts and a walking track."
    0
    Flag
  • Alexu
    "Very quiet! Tons of local stuff to do if you are looking for it. Great place to raise kids Very pet friendly"
    0
    Flag
  • Marebare11856
    "The road has a large curve and no sidewalks so the dog must be on a leash. The neighborhood is very dog and cat friendly. "
    0
    Flag
  • Whitney H.
    "Dog walking and holiday yard decor. Convenience store and gym are walking distance. Little traffic. Wooded areas full of deer"
    1
    Flag
  • Loganb4403
    "Pretty average, right next to Jackson General Hospital it’s a generally nice area, most people are gonna respect you in my area, no riff raff"
    0
    Flag
  • Hollie B.
    "Great places to love. Lovely people. Need more lights. Need more than movies and staking for the kids to do in this town "
    6
    Flag
  • Eynbiee75
    "just becare and pay attention to your surroundings. you can never be too safe. I like it but I also cant wait to move. I'm not comfortable."
    5
    Flag
  • Pelvise R.
    "I can easily get to work...few school zones but otherwise nice. I normally take a back route to avoid traffic on oilwell rd wnd pleasant plains"
    0
    Flag
  • Jessica C.
    "Rarely see strays. Low risk of running into other animals that may be agressive. Wide streets with enough room to walk on a leash."
    1
    Flag

Market trends in Jackson

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$245K
$117MoM
Sale-to-List Price
98.4%
0.3%MoM
Price per sq ft
$137
$1MoM
Available listings
403
3MoM

Home Value

Trulia Estimate
$586K
Since last month
Increased$5K (+0.9%)
Since last year
Increased$61K (+11.5%)
Since last sale
Increased$286K (+95.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +81% in the last 10 years
MonthEstimated value
2026
September 2026$586K
August 2026$581K
July 2026$611K
June 2026$623K
May 2026$631K
April 2026$634K
March 2026$670K
February 2026$528K
January 2026$520K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
63 Southwind Dr, Jackson, TN
0.15
Single-Family Home
$607,000
04/24/26
4
3.5
4,041
22 Southwind Dr, Jackson, TN
0.08
Single-Family Home
$725,000
11/17/25
4
4
4,167
88 Southwind Dr, Jackson, TN
0.19
Single-Family Home
$539,650
09/16/26
3
2.5
3,488
34 Castle Pines Dr, Jackson, TN
0.18
Single-Family Home
$587,500
01/15/26
4
3.5
3,528
114 Country Club Ln, Jackson, TN
0.23
Single-Family Home
$323,600
07/10/26
3
2.5
1,886
68 Windemere Cir, Jackson, TN
0.38
Single-Family Home
$400,000
04/21/26
4
2.5
2,526
222 Country Club Ln, Jackson, TN
0.09
Single-Family Home
$860,000
05/04/26
4
4.5
6,570
156 Channing Way, Jackson, TN
0.68
Single-Family Home
$339,900
08/28/26
4
2.5
3,154

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
17 Winfield Pl, Jackson, TN 38305
0.05
$985,800
5
4.5
5,755
Off Market
40 Winfield Pl, Jackson, TN 38305
0.06
$592,600
4
3.5
4,746
Off Market
22 Southwind Dr, Jackson, TN 38305
0.08
$717,800
4
4
4,167
Off Market
46 Southwind Dr, Jackson, TN 38305
0.09
$554,900
5
4
4,042
For Sale
222 Country Club Ln, Jackson, TN 38305
0.09
$860,000
4
4.5
6,570
Recently Sold
63 Southwind Dr, Jackson, TN 38305
0.15
$607,000
4
3.5
4,041
Recently Sold
32 Torrey Pines Dr, Jackson, TN 38305
0.16
$460,300
4
4.5
3,020
Off Market
132 Torrey Pines Dr, Jackson, TN 38305
0.17
$626,500
3
3.5
3,747
Off Market
34 Castle Pines Dr, Jackson, TN 38305
0.18
$587,500
4
3.5
3,528
Recently Sold
80 Winfield Pl, Jackson, TN 38305
0.18
$767,900
5
4.5
5,564
Off Market
88 Southwind Dr, Jackson, TN 38305
0.19
$539,650
3
2.5
3,488
Recently Sold

Price and Tax history

DateEventPrice
Aug 3, 2026
Source: CWTAR #2602864
PriceChange
$599,000
Price decreased by 5%
Jul 7, 2026
Source: CWTAR #2602864
PriceChange
$629,000
Price decreased by 1%
Jun 18, 2026
Source: CWTAR #2602864
Listed For Sale
$634,500
May 22, 2026
Source: RealTracs MLS as distributed by MLS GRID #3156364
ListingRemoved
$649,700
Apr 26, 2026
Source: CWTAR #2600934
PriceChange
$649,700
Price decreased by 4%

LGBTQ Local Legal Protections

Tori Wilkerson, Hickman Realty Group Inc.-Jack, (731) 664-1006
Some or all of the listings displayed may not belong to the firm whose website is being visited. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 14 Winfield Pl

  • What is the estimated monthly payment for 14 Winfield Pl?
    Based on a $599,000 list price with 20% down at today's rates, the estimated monthly payment for 14 Winfield Pl in Jackson, TN is approximately $3,577 (about $3,242 principal & interest, $260 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 14 Winfield Pl compare to homes in Jackson?
    14 Winfield Pl in Jackson, TN is listed at $599,000, about 144% above the $245K median sale price in Jackson.
  • What do residents say about Jackson?
    Residents describe Jackson, TN as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See homes for sale in Jackson, TN.
  • What are the closest schools to 14 Winfield Pl?
    The closest schools to 14 Winfield Pl in Jackson, TN are North Side High School (rated 3/10), Northeast Middle School (rated 6/10), Thelma Barker Elementary School (rated 5/10).
  • Does 14 Winfield Pl have laundry facilities?
    Yes, 14 Winfield Pl in Jackson, TN has laundry facilities.
  • Does 14 Winfield Pl have a garage?
    Yes, 14 Winfield Pl in Jackson, TN has an attached garage.
14 Winfield Pl, Jackson, TN 38305 is a 4 bedroom, 3 bathroom, 4,108 sqft single-family home built in 1999. This property is currently available for sale and was listed by CWTAR on Jun 18, 2026. The MLS # for this home is MLS# 2602864.