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$315,000
4146221 MLS
Welcome to this Leflore County commercial property located in downtown Greenwood. Positioned in a highly accessible and well-traveled area, this property offers a strong opportunity for both investors and business owners. Just steps away from Greenwood's historic downtown district, the city's primary retail corridor, the property benefits from close proximity to law offices, banks, churches, and a variety of established businesses, adding to its visibility and long-term value. The property features a 4,400± square foot building along with a dedicated parking lot capable of accommodating customers and daily business operations. With two current tenants in place, the property is already generating steady income, making it a solid investment from day one. Whether you are looking to expand your business footprint or secure a reliable income-producing property, this offering provides flexibility and long-term potential in a prime downtown location.

309 W Church Street, Greenwood

Listing courtesy of Wilson Britt with Smalltown Hunting Properties &

$1,000,000
4144748 MLS
Exceptional historic commercial property overlooking the Yazoo River in Greenwood, thoughtfully adapted for modern use as a high-tech training center and culinary facility. Originally constructed circa 1920 for Hohenberg Bros. Cotton Company, the building later served as Hamrick Ford and was home to the well-known Cotton Factor restaurant, making it an important part of Greenwood's commercial and culinary history. The one-story brick structure features a distinctive nine-bay façade highlighted by decorative brick buttresses and terra-cotta panels. Architectural details include a flat roof with parapet and concrete coping and large plate-glass windows that reflect the building's early twentieth-century industrial design. Inside, the building has been repurposed to accommodate a variety of modern uses including conference rooms, technology-equipped training galleries, commercial kitchen and culinary teaching areas, office suites, and flexible warehouse-style space. The open industrial layout and high ceilings create a versatile environment suitable for corporate training, culinary programs, events, creative workspace, or continued commercial use. Located along the Yazoo River, the property offers a distinctive historic setting with convenient access and a large adjacent parking area for employees, clients, and visitors. The flexible layout and historic character provide opportunities for a wide range of commercial or institutional uses. ⸻ Architectural Description Constructed circa 1920, this historic one-story brick commercial building features a distinctive nine-bay façade with terra-cotta panels and decorative brick buttresses. The structure is topped by a flat roof with parapet and concrete coping, while large plate-glass storefront windows reinforce its historic commercial character. ⸻ Property Highlights • Historic commercial building (circa 1920) • Originally home to Hohenberg Bros. Cotton Company • Later operated as Hamrick Ford dealership • Former location of The Cotton Factor restaurant • Overlooks the Yazoo River • Conference and training rooms • Commercial culinary kitchen and demonstration space • Office suites and administrative areas • Flexible warehouse or gallery-style space • Industrial architectural character with high ceilings • Large adjacent parking lot • Adaptive reuse opportunity ⸻ Ideal Uses • Corporate training center • Culinary school or teaching kitchen • Event or hospitality venue • Professional offices • Creative studio or gallery space • Institutional or educational facility • Redevelopment opportunity

101 Main Street, Greenwood

Listing courtesy of Pam Powers with Powers Properties

$450,000
4144355 MLS
A rare opportunity to own one of Greenwood's most architecturally distinctive commercial properties, ideally positioned in the heart of the Historic Downtown District overlooking the Yazoo River. This completely renovated building blends historic character with modern functionality, creating a dynamic environment suited for creative office, studio, or innovation-driven use. Dramatic floor-to-ceiling storefront windows flood the interior with natural light, while soaring ceilings, exposed ductwork, and clean architectural lines provide a sophisticated, industrial-modern aesthetic. The flexible floor plan includes expansive open work areas, multiple private offices, conference space, and collaborative zones—perfect for a wide range of professional, creative, or entrepreneurial uses. A striking central staircase and elevator access enhance both form and function, while thoughtfully designed break areas and support spaces add everyday convenience. Situated along Greenwood's charming brick streets and within walking distance to dining, retail, and cultural amenities, this property offers both visibility and inspiration in one of Mississippi's most authentic downtown settings. An exceptional offering for those seeking a signature space with character, light, and limitless potential.

101 W Front Street, Greenwood

Listing courtesy of Pam Powers with Powers Properties

$123,900
4142341 MLS
COME TAKE A LOOK AT YOUR NEXT MULTI-USE LOT IN GREENWOOD, MS. Welcome to the Leflore 29.5, located within the Greenwood-Leflore Industrial Park. This 29.5± acre tract is currently being farmed in dryland soybeans and cotton, with soils consisting primarily of Askew silt loam and Tensas silty clay loam. The farm can bring a rental income of $2,950 annually. With its prime location and proximity to surrounding businesses, this property offers strong potential for commercial or multi-family residential development. The tract features excellent road access and sits directly across the street from the future Leflore County High School, making it a highly visible and well-positioned investment opportunity. If you are looking for a property with both current agricultural use and future development potential, the Leflore 29.5 is worth a closer look.

Cypress Avenue, Greenwood

Listing courtesy of Wilson Britt with Smalltown Hunting Properties &

$260,000
4 Beds 4 Baths 4140619 MLS
Gracious classic two-story residence situated on a rare double lot along a magnificent oak-lined street in Northeast Greenwood, Mississippi. A separate two-story guest house offers outstanding potential for additional living space, rental income, or a studio.This elegant home blends timeless character with thoughtful updates, featuring beautifully refinished hardwood floors, freshly painted interiors, and tall ceilings. Spacious formal living and dining rooms provide ideal entertaining spaces, while a warm and inviting den with fireplace and brick floors opens to a generously sized kitchen complete with breakfast bar, Viking gas range, new dishwasher and refrigerator and indoor washer&dryer. The flexible floor plan includes a main-level bedroom and bathroom suitable for guests or a private office. Upstairs, the primary suite features a charming balcony overlooking the property and surrounding neighborhood. Two additional bedrooms and a full hall bath provide comfortable accommodations for family or guests. Significant recent improvements include new roofs on both the main house and guest house, along with a freshly painted exterior that enhances the home's classic Southern appeal. A separate two-story guest house offers outstanding potential for additional living space, rental income, or a studio. The structure features a new roof and exterior paint, with new windows and exterior entrance doors already installed on the lower level. Windows for the second floor are included and ready for installation. The spacious interior is ready for renovation, providing an excellent opportunity to customize the space to your needs and vision. Located within walking distance of historic downtown Greenwood, this home offers convenient access to the Yazoo River Trail and Arboretum and to one of the Mississippi Delta's most charming shopping districts. Explore distinctive boutiques, antique galleries, artisan-crafted Mississippi goods, beautiful home decor, and stylish fashions -- all part of Greenwood's vibrant and welcoming downtown experience. Classic architecture, modern updates, and exceptional potential make this a rare Northeast Greenwood opportunity.

404 E Adams Avenue, Greenwood

Listing courtesy of Pam Powers with Powers Properties

$595,000
4 Beds 4 Baths 4140001 MLS
The Grandeur of this custom built home captures you immediately as you walk in the front door into the Grand foyer boasting 20 foot tall ceilings with beautiful chandelier that is highly visible from the exterior through the perfectly placed Arched Picture window in the Clear Story! A True Chef's kitchen with Viking Appliances including Double Electric Steam Oven, 4 Burner Gas Cooktop with Full Size Griddle, and Island with Prep Sink and Seating area being open to the Keeping Room with Double Sided Fireplace. The Dining Room with Tall Ceilings is Situated just off of the Kitchen and Just Across the Main entry Foyer from the Study. Primary Bedroom and Bathroom on Main Level with Heated Floors controlled by wall thermostats. There are 3 additional Upstairs Bedrooms all having access to bathrooms from the bedrooms which make for a nice layout with Media Room separating each. This home also has a totally separate Guest Apartment that has generated an additional $1,600 per month in revenue by leasing to professionals and is currently Leased, but offers separate Living space for Extended Family or perfect In-Law Apartment!

1600 River Oaks Drive, Greenwood

Listing courtesy of Jackie L Sims with Sims Realty & Development LLC

$450,000
5 Beds 4 Baths 4137375 MLS
Stately Southern brick residence designed by renowned architect Frank McGeoy, gracefully set on 1.8 acres with a swimming pool and charming screened pool house, an exceptional offering in one of Greenwood's most established settings. This 4-bedroom, 3.75-bath home is defined by its scale and craftsmanship, featuring 10-foot ceilings, classic crown molding, and beautiful 9-over-9 windows with concrete sills. The main level offers formal living and dining rooms, a guest bedroom with full bath, and a renovated kitchen with beamed ceiling, double ovens, and abundant cabinetry. A breakfast room, sunroom, and utility room add both comfort and functionality. Upstairs, a gracious staircase leads to a wide central landing, four bedrooms, three private baths, and a richly appointed wood-paneled study--spaces that reflect the home's timeless design and livability. Built for George Durden Pillow and Frances Dale Pillow, this residence carries a remarkable legacy. Mr. Pillow, a Mississippi State graduate and one of the last athletes to letter in four sports, was inducted into both the Mississippi State and Mississippi Sports Halls of Fame and served in numerous civic leadership roles throughout the region. Mrs. Pillow was a visionary in cultural and civic life across Mississippi--serving as President of the Garden Clubs of Mississippi, leading the development of the state Garden Club Headquarters, and contributing to preservation, beautification, and community initiatives statewide. She was also honored as Mississippi Mother of the Year. Her belief that ''flowers and greenery are not luxuries, but necessities'' is a philosophy that resonates in the setting and spirit of this property. Still held within the original family, this home represents a rare continuity of ownership--an enduring testament to its quality, design, and significance. A timeless Southern residence offering not just a place to live, but a place to carry forward a legacy.

2502 W Claiborne Avenue, Greenwood

Listing courtesy of Pam Powers with Powers Properties

$450,000
2 Baths 4136918 MLS
Positioned along highly traveled US Highway 82, this well-known commercial property offers exceptional visibility with approximately 125 feet of highway frontage in the heart of Greenwood, Mississippi. Built in 1977, the building contains approximately 3,672 square feet and is ideally suited for restaurant or food service operations. The property features ample parking with approximately 45 dedicated spaces, ensuring convenient access for customers and staff. Accessibility features are already in place, enhancing usability and compliance. The interior is equipped with multiple commercial coolers, cookers, and restaurant furniture, providing a strong foundation for immediate operation or an efficient restart with minimal build-out. The freestanding structure and prominent signage opportunities make this location ideal for a restaurant, take-out concept, or other high-traffic commercial use. Its strategic highway location offers excellent exposure to daily commuter traffic and regional travelers alike. Whether you're an owner-operator looking to establish a presence or an investor seeking a visible commercial asset, this property presents a rare opportunity in a proven corridor of Greenwood.

917 W Highway 82, Greenwood

Listing courtesy of Elecia Elmore with Powers Properties

$322,000
2.5 Baths 11629240 MLS
Prime commercial property offering 6,640± square feet on .84 acres with excellent highway visibility and ample parking. Previously designed for medical/office use, this versatile building is ideal for a medical clinic, dental practice, professional offices, counseling center, training facility, or multi-tenant investment. The layout includes a kitchen/break area, 2.5 bathrooms, approximately 20 exam/office rooms, reception/office area, spacious waiting area, medical filing area, conference room, and a locked supply/stock room. The flexible floor plan allows for easy reconfiguration to suit a variety of business needs. Convenient location with strong access and visibility makes this an excellent opportunity for owner-occupants or investors. $50,000 below appraisal. Owner financing will be an option. Price: $322,000

201 Hwy 7 N, Greenwood

Listing courtesy of Rhonda Lee with Landmark Realty

$299,000
6 Beds 5 Baths 4118057 MLS
Timeless Treasure on River Road - A True Colonial Revival Classic Rustic kisses pristine in this one-of-a-kind Colonial Revival home on River Road—designed by noted King's Daughters architect, Frank McGeoy. Nestled in a meadow-like setting behind a gated entrance, this stately historic brick home is brimming with charm, elegance, and space galore. Remodeled in the 1990s and refreshed again in 2024, the home features fresh interior and exterior paint, epoxied tile kitchen counters, and a newly constructed 2-car garage completed in 2025. The elegant formal living and dining rooms include a gorgeous real wood fireplace and stunning crown molding, while the sunken playroom and columned back porch offer inviting spaces to gather and relax. The kitchen is filled with custom cabinetry, a center island, and flows beautifully for entertaining. Original hardwood floors run throughout the home, which boasts six oversized bedrooms and four and a half baths—all with impeccable tilework and fixtures. A handsome study with brick floors and its own fireplace opens onto a charming brick patio—perfect for working from home or quiet reflection. This property also includes a bonus lot on the river and would qualify for the National Register of Historic Places. A rare offering on Greenwood's storied Doctor's Row, this home blends timeless architecture, thoughtful renovations, and gracious Southern living—all in one unforgettable address, walking distance to UMMC Hospital.

1211 River Road, Greenwood

Listing courtesy of Pam Powers with Powers Properties

$515,000
5 Beds 4 Baths 4117885 MLS
Historic Victorian Gem on Grand Boulevard - Greenwood, MS Welcome to this breathtaking 1904 Victorian home, ideally positioned on the corner of Greenwood's iconic Grand Boulevard. Listed on the National Historic Registry, this residence has been thoughtfully remodeled to provide all the modern conveniences of new construction while preserving the timeless character that makes it so special. From the intricate millwork and soaring ceilings to the inviting wraparound porch, every detail reflects the elegance of a bygone era. Step inside and you'll find gracious living spaces filled with warmth and charm. Step outside and discover your own backyard oasis, complete with a luxurious pool—perfect for relaxing or entertaining. This property is more than just a home—it's a piece of Greenwood's history, ready to be cherished by its next owner.

101 E President Avenue, Greenwood

Listing courtesy of Lyn McCool with Powers Properties

$45,000
2 Beds 1 Baths 11433569 MLS
Property is being sold in an as is condition, and the condition is unknown and may include defects, possible health or safety hazards, or debris, or be located in a Special Flood Hazard Area. Proof of Funds Required. The seller requires that the high bidder be able to demonstrate proof of funds or financing pre-qualification within 24 hours of the auction. Buyer must obtain a pre-qualification letter from a lender of their choice. If buyer intends to pay with cash, a bank letter or other financial account statement showing proof of sufficient funds to cover 100% of the purchase price will be required (account numbers should be removed or redacted). Buyer understands and agrees to submit said documentation to auctioneer within 24 hours of the auction. Occupation and Utilities Disclosure. To the best of Seller's knowledge, the property is vacant. The utilities to this property are not currently turned on and the property may be winterized. Utilities will not be turned on prior to closing, regardless of inspections. Buyer will need to consider this and account for it if/when inspecting the property. Buyer is responsible for utility transfer post-closing. Title Disclosure. Closing must occur on or before 30 days from seller's acceptance of offer provided title is clear. If a valid objection or preclusion to title is identified by the Closer, seller shall, at seller's option: have one-hundred and twenty (120) days from the date of the original closing (the Cure Period) or such additional time as may be agreed to in writing by the Parties to satisfy such objections and preclusions; or, choose to terminate the transaction by returning Buyer's down payment upon which the parties shall incur no further liability to the transaction or each other. For further clarification, please read the sample contract available on our website. Buyer understands and acknowledges that square footage, acreage, and/or bedroom and bathroom count for the building sited on the property is based on an appraisal or county assessor information. Buyer further understands and acknowledges that measurements/acreage/count can vary from a few feet to several hundred feet regardless of source (County Assessor's records, appraisal, or appraisal measurement report, etc.) and that said sources may contain erroneous information or measurements/acreage/count. Buyer should conduct their own investigation and satisfy that the size and/or square footage, acreage, and bedroom/bathroom count of the dwelling/building is acceptable to the Buyer prior to placing any bid or offer on a property. By placing a bid or offer on a property, Buyer is accepting the property in as-is where-is condition and agrees to be bound to the bid or offer should a discrepancy arise. The Buyer will be responsible for the payment of all UCC Liens of Record on the property and the clearance from the title commitment of the lien if so required. On this Second Chance property the foreclosure deed may not yet be recorded. Seller will make every reasonable effort to ensure the deed is filed of record as soon as possible.

411 W Jefferson Ave, Greenwood

Listing courtesy of Keith Babb with Williams & Williams Real Estate Auctions

$280,000
3 Baths 4098708 MLS
This is an incredible opportunity to own a prime property in the heart of historic downtown Greenwood, MS! This two-story commercial building offers a perfect blend of retail and residential spaces, making it an ideal investment for entrepreneurs and visionaries looking to be part of the vibrant downtown scene. Features: • Retail Potential: Two separate retail spaces on the first floor, currently leased on a month-to-month basis. Tenants can remain or vacate based on the new owner's preference. • Residential Opportunity: The second floor features a spacious apartment with all-new windows and potential for additional living spaces. Downtown living is highly desirable, with apartments and flats rarely available! • Prime Location: Situated near popular landmarks such as the Alluvian Hotel, Viking Cooking School and Retail Store, boutique shops, and banks, this property is at the heart of Greenwood's bustling downtown district. • Historic Charm: A contributing building in the Greenwood Downtown Historic District, this two-story brick building blends historic significance with modern updates. • Architectural Details: • Tall ceilings, adding character and charm • Modern glass storefront with a canvas awning • Metal and glass display windows • Historic cast-iron posts, likely preserved within the supporting piers This well-maintained property is perfect for anyone looking to invest in Greenwood's thriving downtown area. With its mix of rental income, residential appeal, and historic character, it's an opportunity not to be missed!

220 Howard Street, Greenwood

Listing courtesy of Pam Powers with Powers Properties

$55,000
4093862 MLS
This 7.5± acre tract of land presents a prime investment opportunity in the heart of Leflore County, Mississippi. Situated just 2.5 miles south of the city of Greenwood, this property offers immense potential for residential, commercial, industrial, or mixed-use development. Whether you're an investor or developer, this versatile land is a blank canvas awaiting your vision. Key Features: Versatile Zoning: With a range of zoning possibilities, this property can accommodate residential, commercial, industrial, or mixed-use projects, making it a flexible investment opportunity. Strategic Location: Located just minutes from Greenwood, this property provides easy access to major highways and city amenities, enhancing its appeal for a variety of development options. Multi-Family Housing: Perfectly suited for multi-family housing units, providing an ideal solution for the growing demand in the area. Industrial Potential: The property's location includes frontage on the Illinois Central Railroad, making it an attractive prospect for manufacturing, logistics, and warehouse development. Highway Frontage: Boasting frontage on Hwy 49E, this property offers excellent visibility and accessibility for commercial ventures.

U.S. 49, Greenwood

Listing courtesy of Billy Carpenter with Smalltown Hunting Properties &