Chestnut Hill Real Estate

Welcome to Chestnut Hill, a picturesque subdivision nestled in the heart of Madison County, Mississippi. This charming community is designed for those who appreciate the perfect blend of tranquility and accessibility, making it an ideal place for families, retirees, and everyone in between.

Chestnut Hill boasts beautifully landscaped streets lined with mature trees that provide a serene atmosphere for leisurely strolls or morning jogs. The subdivision features a variety of well-appointed homes, each showcasing unique architectural styles and modern amenities. Whether you’re looking for a cozy single-family home or a spacious abode perfect for entertaining, Chestnut Hill has something to suit every taste and lifestyle.

One of the standout features of this community is its commitment to creating a welcoming environment. Residents enjoy a sense of camaraderie, with neighborhood events and gatherings that foster connections among neighbors. The nearby parks and recreational facilities offer plenty of opportunities for outdoor activities, from picnics to sports, ensuring there's always something fun to do.

Conveniently located just minutes from the vibrant town of Madison, Chestnut Hill provides easy access to shopping, dining, and entertainment. Families will appreciate the top-rated schools in the area, which are known for their commitment to academic excellence and community involvement.

If you’re seeking a peaceful retreat with a strong sense of community, look no further than Chestnut Hill. Experience the charm and warmth of this delightful subdivision, where your dream home awaits!

Newest Listings in Chestnut Hill

$175,000

4156194 MLS

Build your dream home on almost 3 acres of lakefront property in the peaceful, gated community of Chestnut Hill in Flora. Nestled among rolling woods, scenic lakes, and abundant wildlife, this beautiful homesite offers a rare opportunity to enjoy privacy, serenity, and natural beauty just minutes from Madison. Residents enjoy neighborhood gatherings around the fire pit, fishing, walking trails, and breathtaking sunsets over the lakes. Conveniently located just 8.5 miles from Highland Colony Parkway and adjacent to the charming Town of Livingston, you'll love the ability to take a golf cart to dinner, shops, and local amenities. Experience the perfect blend of quiet country living and everyday convenience in one of Madison County's most picturesque communities.

177 Chestnut Hill Road, Flora

Listing courtesy of BHHS Gateway Real Estate.

$90,000

4153394 MLS

Special Opportunity for 2 Acre lot is NOW in Chestnut Hill subdivision! Private & Gated Community of only 95 homesites on 430 acres of beautifully rolling hills in Madison County, Mississippi! Highly regarded for fishing and convenient, direct access to the Town of Livingston with its restaurants, shopping and events! Call your favorite realtor today - gate code required! Come see the beauty you have heard everyone talking about!

205 Chestnut Spring Road, Flora

Listing courtesy of Bowie & Co Real Estate, LLC.

$89,500

4149950 MLS

This is your chance to own a beautiful lot in Chestnut Hill in Flora of Madison County. The setting on this gorgeous, corner lot will be perfect to build your dream home and watch the sunsets in the afternoon. Call your agent today to get the covenants and plat available!

177 Chestnut Hill Road, Flora

Listing courtesy of Polles Properties, LLC.

$195,000

4140061 MLS

Welcome to the picturesque Chestnut Hill Community in Madison, where luxury living meets natural beauty. This 3.55-acre residential lot offers an opportunity to build your dream home amidst tranquil water front views of a 44-acre stocked fishing lake. Situated within 2 miles of the charming Town of Livingston, you'll enjoy easy access to local amenities, schools, and entertainment while still relishing the privacy and exclusivity of your expansive lot. Whether you're an avid angler looking forward to fishing right from your front yard or simply seeking a serene retreat to call home, this property offers the perfect blend of convenience with a peaceful atmosphere for you and your family. Don't miss this opportunity to own a piece of Chestnut Hill and create your own private oasis in this desirable Madison location.

Chestnut Hill Road, Flora

Listing courtesy of Weichert Realtors - Innovations.

$139,999

4126806 MLS

In search of privacy in Chestnut Hill, this is it. Heavily wooded, and just down the street from the boat launch, you can build your dream home tucked up in the woods! The town of Livingston is just minutes away and offers dining options, and an upscale cocktail lounge!

Lot 97 Chestnut Hill Road, Flora

Listing courtesy of The Compass Group.

$174,000

4113816 MLS

This beautiful waterfront lot is located in the Chestnut Hill Subdivision. It is approximately 2.58 acres. The man made lake is 50 acres. The lake is maintain by Southeqster Pond Management. I is perfect for fishing and picturesque sunsets.

No Lot #22 Chestnut Hill, Madison

Listing courtesy of Keller Williams.

$489,500

4108110 MLS

15.36 acres to build your dream home in the beautiful gated neighborhood of Chestnut Hill off highway 463 in Madison County. Chestnut Hill offers 3 lakes, incredible views and seconds away from the Town of Livingston. Enjoy serene natural beauty in a peaceful tranquil setting just 8.5 miles away from Madison. Call today for more information.

Chestnut Hill Road, Flora

Listing courtesy of Nix-Tann & Associates, Inc..

$247,500

4108109 MLS

11.9 acre lot to build your dream home in the beautiful gated neighborhood of Chestnut Hill off highway 463 in Madison County. Ask about the possibility of dividing this lot. Chestnut Hill offers 3 lakes, incredible views and seconds away from the Town of Livingston. Enjoy serene natural beauty in a peaceful tranquil setting just 8.5 miles away from Madison. Call today for more information.

Chestnut Hill Road, Flora

Listing courtesy of Nix-Tann & Associates, Inc..

$159,900

4030699 MLS

Take advantage of this once-in-a-lifetime opportunity to build your dream home on a prime, 2.8-acre WATERFRONT lot in the stunning Chestnut Hill Subdivision. This up-and-coming area offers the perfect balance of urban conveniences and rural charm, with access to restaurants, shopping, and the town of Livingston just minutes away. The lot boasts breathtaking views, featuring beautiful big trees and rolling hills, and its location on the water makes it ideal for fishing and water activities. Don't miss this chance to enjoy the best of both worlds in a truly unique and special location. Min sq footage is 3500. Call your agent today

138 Chestnut Hill Rd, Flora

Listing courtesy of Polles Properties, LLC.

Start Your Search

Copyright 2026 Mississippi Gulf Coast Multiple Listing Service, Inc. Buyer and/or Buyer's Agent should verify data and evaluate source. This information is furnished by the Mississippi Gulf Coast Multiple Listing Service, Inc. This data is copyrighted and may not be transmitted, retransmitted, copied, framed, repurposed, or altered in any way for any other site, individual and/or purpose without the express written permission of the Mississippi Gulf Coast Multiple Listing Service, Inc. All properties are subject to prior sale, change or withdrawal. Neither the MLS nor the Listing Broker will be held responsible for any typographical errors, misinformation and misprints and shall be held totally harmless. Data displayed is a portion of, and not a complete listing of all listing information published in the Mississippi Gulf Coast Multiple Listing Service, Inc.