Exquisite craftsmanship, timeless architecture, and extraordinary attention to detail define this remarkable custom residence in the prestigious Chestnut Hill community. Situated on 2 beautifully maintained acres with access to the community's 40-acre lake, this exceptional 4-bedroom, 4.5-bath home offers a rare combination of refined luxury, natural beauty, and effortless entertaining. From the moment you enter, rich heart pine flooring, hand-finished pickled wood accents, soaring ceilings, and exposed pine beams create an atmosphere of warmth and sophistication. Upstairs, reclaimed hardwood flooring from a historic business built in 1895 on Pearl Street in downtown Jackson adds a distinctive touch of history and character, reflecting the home's exceptional craftsmanship and thoughtful design. The gourmet kitchen is a true showpiece, featuring an oversized island, Sub-Zero refrigerator, professional six-burner range, custom vent hood, microwave, floating shelving, touch-activated faucet, and beautifully appointed walk-in pantry with custom built-ins. A conveniently located drop zone adds everyday functionality without compromising style. Designed for seamless indoor-outdoor living, the extraordinary covered porch features a fully equipped outdoor kitchen with Viking grill, stainless steel sink, plumbing and drainage, abundant storage, fireplace, and television—creating the ultimate setting for year-round entertaining. Peaceful views of deer, wild turkeys, ducks, and geese provide an ever-changing backdrop of natural beauty. The private primary suite offers a dramatic vaulted ceiling, direct access to the outdoor living area, and a spa-inspired bath with dual vanities, private water closet, and two expansive custom walk-in closets. Two additional main-level bedrooms include a beautifully appointed guest suite with a spacious walk-in closet and private bath. Upstairs, two generous flex spaces connected by a full bath offer exceptional versatility for guest accommodations, executive offices, media or game rooms, or fitness areas. Two separate accesses to spacious storage areas provide remarkable convenience. Even the utility spaces reflect exceptional design. The oversized laundry room features designer tile flooring, ceiling-height custom cabinetry, built-in ironing station, wine cooler, and dedicated space for two additional refrigerators or freezers. The insulated garage is complemented by a heated and cooled workshop with built-in workbench and pegboard storage, ideal for hobbies, projects, or additional conditioned storage. Additional custom features include a sophisticated zoned audio system extending throughout the main living areas, primary suite and bath, covered porch, garage, and workshop; a six-zone irrigation system; underground dog fence; and casement windows with convenient crank-out operation. Thoughtful storage throughout and a whimsical Harry Potter passage connecting the hallway and utility room add another layer of charm and individuality to this extraordinary residence. The Chestnut Hill lifestyle is equally impressive. Residents enjoy two picturesque lakes of approximately 40 and 50 acres, stocked with bass and bream. At the property's lake lot, a specially prepared gravel bream bed and installed fish feeder enhance the fishing experience. The community's distinctive direct side-by-side access to the Township at Livingston places an inviting collection of restaurants, shops, and gathering places just moments away. At 144 Chestnut Hill, luxury extends far beyond the home itself—it's a lifestyle. Imagine mornings watching wildlife from the back porch, afternoons fishing at the lake, evenings entertaining by the outdoor fireplace, or taking the side-by-side to Livingston for dinner. A truly distinctive residence where historic character, uncompromising craftsmanship, natural beauty, and refined Southern living come together in one extraordinary setting.
Chestnut Hill, located between Highland Colony Parkway and Old Canton Road, is a residential and suburban Madison neighborhood with leafy streets and a low-rise, landscaped feel. The neighborhood’s character concentrates around the Highland Colony Parkway corridor near Main Street, where coffee counters, local eateries, and small-shop storefronts set a steady daytime rhythm. Community pillars nearby include the Mississippi Crafts Center for gallery browsing, the Malco Grandview Cinema for movie nights, and the Madison Station Elementary School campus as a familiar landmark. Homes tend toward newer builds with tidy setbacks and garage-forward streetscapes. Sidewalk pockets and pocket greens shape a walk-and-stroll routine. The setting reads calm and commuter-friendly, with retail clusters kept to the main roads.
Provided by Walk Score and Local Logic
Market insights
144 Chestnut Hill Rd · $1,011,000
DAYS ON MARKET
1 days
The average home goes pending in 53 days.
SALE-TO-LIST
97.4%
Most homes are selling 3% below list price.
LIST PRICE
$1,011,000
Median sale price in this area is $373,780. (63% lower than this home)
PRICE DROP
0 price drops
20% of homes in this area have had a price drop in the past month.
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
Gas log and wood-burning fireplaces, including one in the den and an outdoor fireplace
Insulated windows and doors
Ceiling fans
Crown molding
High ceilings
High-speed internet
Storage
Bathrooms
4 full bathrooms
1 half bathroom
Kitchen
Dishwasher, disposal, gas cooktop, microwave, refrigerator, and wine cooler
Eat-in kitchen with granite counters, pantry, and kitchen island
Laundry & utility
Main-level laundry room
Electric dryer hookup
Flooring
Ceramic tile and hardwood
Heating & cooling
Natural gas and fireplace heating
Central air
Exterior features
Wooded lot with lake waterfront
Brick patio
Outdoor kitchen
Private yard
Rain gutters
Home design
Two-story single-family house
Parking
Three-car garage
Concrete and gravel parking
Security
Closed-circuit cameras
Gated community
Security system
Smoke detectors
Construction
Brick and wood siding
Slab foundation
Architectural shingle roof
Utilities
Public water and sewer
Electricity and natural gas connected
Fiber to the house
HOA & community
Annual association fee includes management
Community fishing
Electricity and solar
View estimated energy costs and solar savings for this home
The purposes for Planned Unit Development PUD districts are: To provide for the development of relatively large land areas as total cohesive and coordinated units, rather than development on a lot-by-lot basis.; To permit more flexible and advantageous use of sites, especially with regard to natural features of the landscape, through the relaxation of conventional zoning requirements including minimum lot size and minimum lot width, while at the same time retaining approximately the same overall density as would ordinarily apply if the same areas were developed by conventional methods.; To help reduce the cost of residential development by allowing more dwelling units per gross acre than could be built in a conventional low density subdivision due to the extensive space requirements of streets rights-of-way, utility easements, etc., in a conventional subdivision and by reducing the length of streets and utility extensions through concentration or clustering of housing; To provide for the development of sites in which land not used for structures and yards but not required by the basic zoning of the site shall be reserved collectively in contiguous units accessible to all dwellings within the PUD as open space; this open space will provide recreational opportunities for the residents of the PUD, and will also afford improved, safer pedestrian circulation within the PUD.
Permitted uses
Include but are not limited to:
No uses permitted by right
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
3/10 Fire Factor
0.15% chance of being in a wildfire in next 30 years
6/10 Heat Factor
7 days above 108° expected this year, 19 days in 30 years
6/10 Wind Factor
76% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Flora, MS • 39071
Average low and high temperatures (°F)
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Sun exposure
In this area, properties receive around 9.9 hours in
June and 4.8 hours in December, which is comparable to the
U.S. average for solar exposure.
9.9 hrs
4.8 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 144 Chestnut Hill Rd
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