20 Winterfield Dr
Jackson, MS 39211
Rolling Hills- 5 Beds
- 5 Baths
- 4,491 sqft (on 0.32 acres)
5 Beds
5 Baths
4,491 sqft
(on 0.32 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
2000
Lot Size
0.32 acres
Living Area
4,491 sqft
Price/Sqft
$167
Parking
Garage
HOA
$208/Monthly
About this House
Stately and elegant, this 5-bedroom, 5-bathroom residence is ideally situated on a gated, quiet, and private 5-home cul-de-sac with easy golf-cart access to the Country Club of Jackson. Showcasing timeless architectural detail and superb craftsmanship, the home features 10 inch heart pine floors, spacious formal and informal living areas, and a striking double-sided fireplace between the formal living and dining rooms. The chef's kitchen is well-appointed for entertaining, and the primary suite offers a luxurious retreat with an updated en suite bath and generous closet space. A charming New Orleans-style courtyard with fountain enhances the outdoor living experience, complemented by an indoor/outdoor sound system for seamless entertaining. Additional amenities include a two-car garage, separate golf cart garage, and beautifully landscaped grounds. A rare opportunity in one of Jackson's most desirable and established neighborhoods.
20 Winterfield Dr, Jackson, MS 39211 is a 5 bedroom, 5 bathroom, 4,491 sqft single-family home in Rolling Hills, built in 2000. It last sold for the $828,000 asking price on Oct 8, 2025. It is currently off market. The Trulia Estimate is $750,500, with a rent estimate of $3,276/month.
Home Details for 20 Winterfield Dr
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MLS Status: Closed |
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Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 5 |
Dimensions and Layout Living Area: 4491 Square Feet |
Appliances & Utilities Utilities: Cable Connected, Natural Gas Connected, Sewer Connected, Underground Utilities, Natural Gas in KitchenAppliances: Built-In Freezer, Built-In Gas Oven, Built-In Gas Range, Built-In Refrigerator, Dishwasher, Disposal, Exhaust Fan, Ice Maker, Microwave, Range Hood, Tankless Water Heater, Wine RefrigeratorDishwasherDisposalMicrowave |
Heating & Cooling Heating: Central,Natural GasHas CoolingAir Conditioning: Central Air,Gas,Multi UnitsHas HeatingHeating Fuel: Central |
Fireplace & Spa Fireplace: Dining Room, Double Sided, Gas Log, Gas Starter, Great Room, Living Room, VentlessHas a Fireplace |
Levels, Entrance, & Accessibility Stories: 2Levels: Two |
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Exterior Home Features Roof: Architectural ShinglesExterior: Gas Grill, Lighting, Outdoor Grill, Rain GuttersFoundation: SlabNo Private Pool |
Parking & Garage Number of Garage Spaces: 2.5Number of Covered Spaces: 2.5No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 2.5Parking: Driveway,Garage Faces Side,Golf Cart Garage,Parking Pad |
Water & Sewer Sewer: Public Sewer |
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Year Built Year Built: 2000 |
Property Type / Style Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceStructure Type: HouseArchitecture: House |
Building Construction Materials: StuccoNot a New Construction |
Property Information Condition: Move In ReadyParcel Number: 07510301002 |
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Price List Price: $828,000 |
Status Change & Dates Off Market Date: Thu Sep 04 2025 |
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Direction & Address City: JacksonCommunity: Country Club Of Jackson |
School Information Elementary School: SpannJr High / Middle School: Bailey APACHigh School: Murrah |
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Building Area Building Area: 4491 Square Feet |
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HOA Fee Includes: Accounting/Legal, Maintenance Grounds, Management, Security, OtherHOA Fee (second): 280HOA Fee Frequency (second): AnnuallyHas an HOAHOA Fee: $2,500/Annually |
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Lot Area: 0.32 acres |
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Mobile Home Park Mobile Home Units: Feet |
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Mls Number: 4113634 |
Last check for updates: about 3 hours ago
Listed by Brooks Poole, (601) 540-0951
The Furr Group
Bought with: Juanita Kennedy, (601) 955-9731, Kennedy & Company Real Estate
Source: MLS United, MLS#4113634
Price History for 20 Winterfield Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 10/08/2025 | -- | Sold | MLS United #4113634 |
| 09/04/2025 | $828,000 | Pending | MLS United #4113634 |
| 05/17/2025 | $828,000 | Listed For Sale | MLS United #4113634 |
| 01/24/2018 | $549,000 | ListingRemoved | Agent Provided |
| 12/04/2017 | $549,000 | PriceChange | Agent Provided |
| 06/26/2017 | $595,000 | Listed For Sale | Agent Provided |
Market trends in Jackson
Last updated June 2026
Avg. sale price
$146K
$18.83KMoM
Sale-to-List Price
96.4%
Price per sq ft
$84
$5MoM
Available listings
730
8MoM
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $9,030 |
| Assessment | $482,620 |
Home facts updated by county records
Comparable Sales for 20 Winterfield Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.19 | Single-Family Home | - | 05/28/26 | 4 | 3.5 | 3,515 | |
0.08 | Single-Family Home | - | 08/22/25 | 4 | 2.5 | 3,159 | |
0.21 | Single-Family Home | - | 04/15/26 | 4 | 3.5 | 3,869 | |
0.40 | Single-Family Home | - | 08/08/25 | 5 | 4 | 3,846 | |
0.32 | Single-Family Home | - | 12/30/25 | 5 | 3.5 | 3,341 | |
0.08 | Single-Family Home | - | 01/13/26 | 4 | 3.5 | 2,945 | |
0.36 | Single-Family Home | - | 09/05/25 | 4 | 3.5 | 3,181 | |
0.45 | Single-Family Home | - | 08/15/25 | 5 | 3.5 | 3,340 | |
0.08 | Single-Family Home | - | 05/13/26 | 4 | 4 | 2,273 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 20 Winterfield Dr.
What Locals Say about Rolling Hills
At least 16 Trulia users voted on each feature.
92 % Say car is needed
89 % Say parking is easy
82 % Say it's dog friendly
75 % Say yards are well-kept
64 % Say there's holiday spirit
61 % Say there are sidewalks
55 % Say it's quiet
47 % Say people would walk alone at night
46 % Say kids play outside
45 % Say streets are well-lit
36 % Say neighbors are friendly
27 % Say it's walkable to restaurants
19 % Say they plan to stay for at least 5 years
11 % Say it's walkable to grocery stores
11 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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Information is deemed to be reliable but not guaranteed. Copyright 2026 MLS United, LLC.

