$759,900
- 5 Beds
- 5 Baths
- 4,491 sqft (on 0.32 acres)
20 Winterfield Dr, Jackson, MS 39211
Est. Refi. Payment $4,810/mo*
Refinance Your HomeHome Value
Trulia Estimate
$760KSince last month
Decreased$15K (-1.9%)Since last year
Decreased$25K (-3.2%)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 +12% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $760K |
| August 2026 | $775K |
| July 2026 | $748K |
| June 2026 | $791K |
| May 2026 | $737K |
| April 2026 | $740K |
| March 2026 | $744K |
| February 2026 | $735K |
| January 2026 | $758K |
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 |
|---|---|---|---|---|---|---|---|
0.19 | Single-Family Home | - | 05/28/26 | 4 | 3.5 | 3,515 | |
0.21 | Single-Family Home | - | 04/15/26 | 4 | 3.5 | 3,869 | |
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 | |
0.08 | Single-Family Home | - | 05/13/26 | 4 | 4 | 2,273 | |
0.38 | Single-Family Home | - | 03/20/26 | 5 | 2.5 | 3,200 | |
0.56 | Single-Family Home | - | 11/07/25 | 7 | 4 | 3,760 | |
0.29 | Single-Family Home | - | 05/29/26 | 3 | 2.5 | 3,250 | |
0.39 | Single-Family Home | - | 07/31/26 | 4 | 2.5 | 2,867 |
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 |
|---|---|---|---|---|---|---|
0.05 | $1,035,900 | 4 | 4.5 | 5,206 | Off Market | |
0.06 | $208,000 | 2 | 2 | 1,848 | For Sale | |
0.08 | $290,100 | 4 | 2.5 | 3,159 | Off Market | |
0.08 | - | 4 | 3.5 | 2,945 | Recently Sold | |
0.08 | - | 4 | 4 | 2,273 | Recently Sold | |
0.10 | $904,900 | 6 | 5.5 | 5,911 | Off Market | |
0.11 | $161,900 | 3 | 2 | 1,735 | Off Market | |
0.09 | $258,400 | 3 | 2.5 | 2,707 | Off Market | |
0.12 | $182,100 | 3 | 2 | 1,710 | Off Market | |
0.12 | $177,500 | 3 | 2 | 1,710 | Off Market | |
0.12 | $141,700 | 2 | 2.5 | 1,350 | Off Market |
Local Information
-- mins to
Home Highlights
Single-Family Home
Built in 2000
0.32 acre lot
4,491 sqft
$169/sqft
Garage
HOA $208/mo
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 was last sold on Oct 8, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $759,900, with a rent estimate of $3,346/month.
Last check for updates: about 4 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
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 |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Oct 8, 2025 Source: MLS United #4113634 | Sold | -- |
Sep 4, 2025 Source: MLS United #4113634 | Pending | $828,000 |
May 17, 2025 Source: MLS United #4113634 | Listed For Sale | $828,000 |
Jan 24, 2018 Source: Agent Provided | ListingRemoved | $549,000 |
Dec 4, 2017 Source: Agent Provided | PriceChange | $549,000 Price decreased by 8% |
Jun 26, 2017 Source: Agent Provided | Listed For Sale | $595,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $9,419 | $500,190 |
Home facts updated by county records
Market trends in Jackson
Last updated August 2026
Avg. sale price
$142K
Sale-to-List Price
97.0%
0.1%MoM
Price per sq ft
$87
$2MoM
Available listings
753
11MoM
Around this home
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Information is deemed to be reliable but not guaranteed. Copyright 2026 MLS United, LLC.
Frequently asked questions about 20 Winterfield Dr
- What is 20 Winterfield Dr estimated to be worth?Trulia's estimated value for 20 Winterfield Dr in Jackson, MS is $759,900.
- What is the price history for 20 Winterfield Dr?20 Winterfield Dr in Jackson, MS last sold in October 2025.
- Is Jackson a buyer's or seller's market?Jackson is currently a buyer's market, based on recent for-sale activity.
- What's the median sale price in Jackson?The median sale price in Jackson is $142K. That is roughly unchanged from the prior month.
- Does 20 Winterfield Dr have air conditioning?Yes, 20 Winterfield Dr in Jackson, MS has air conditioning.
- How big is the lot at 20 Winterfield Dr?The lot at 20 Winterfield Dr in Jackson, MS is about 0.32 acres (13,939 sq ft).

