Henderson South Side, KY homes for sale & real estate

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306 S Elm Pl, Henderson, KY 42420
306 S Elm Pl, Henderson, KY 42420
306 S Elm Pl, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
THIS IS A CUTE STARTER OR RETIREMENT HOME LOCATED CLOSE TO DOWNTOWN. THE SELLER IS A KENTUCKY REAL ESTATE BROKER.

$139,900

2 beds1 bath750 sq ft

306 S Elm Pl, Henderson, KY 42420

4,648 sq ft lot • Car-dependent

226 Oriole Dr, Henderson, KY 42420
226 Oriole Dr, Henderson, KY 42420
226 Oriole Dr, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Don't miss this adorable cottage style home tucked away on a quiet dead-end street in the heart of Henderson, KY. This 3-bedroom, 2-bath home features an updated kitchen with stainless steel appliances and breakfast bar, 2 bedrooms/1 bath on main level and private primary suite with large walk-in closet, bonus room and spacious laundry room in the finished basement. Updates include vinyl and tile flooring throughout, new windows in 2025, new roof in 2021, new heating & air in 2018, basement waterproofed in 2021 and many other improvements throughout. This low maintenance, all electric home is located on Oriole Dr. just steps from all the shopping, activities and events downtown Hender

$199,000

3 beds2 baths1,482 sq ft

226 Oriole Dr, Henderson, KY 42420

5,129 sq ft lot • 2 garage spots • Car-dependent

503 Chestnut St, Henderson, KY 42420
503 Chestnut St, Henderson, KY 42420
503 Chestnut St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Welcome to this well-maintained 3-bedroom, 2-bath home situated on a spacious corner lot in a desirable neighborhood. From the moment you arrive, you'll be captivated by the stunning curb appeal, highlighted by lush landscaping, mature trees, and vibrant flower beds that frame the property. Step inside to find a warm and inviting interior perfect for both relaxing and entertaining. The kitchen offers ample cabinet space, modern appliances, and a convenient layout for everyday living. The primary suite includes a private en-suite bath and generous closet space, while the two additional bedrooms provide flexibility for family, guests, or a home office. Outside, the expansive yard offers plent

$245,000

3 beds2 baths3,640 sq ft

503 Chestnut St, Henderson, KY 42420

0.32 acre lot • Car-dependent

220 S Main St, Henderson, KY 42420
220 S Main St, Henderson, KY 42420
220 S Main St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
The phrase "house with a white picket fence" often symbolizes the American Dream or a vision of an idyllic, suburban life. It represents a longing for a stable and prosperous life, often associated with homeownership and a peaceful, safe environment. 220 South Main Street offers the opportunity to live on Main St, one of the most popular streets in downtown Henderson, with proximity to shops, restaurants, the library, and our Riverfront. It also offers the opportunity to live in your very own “Southern Living” home, with its white picket fence. You’ll first be greeted with the one-of-a-kind double decker front porch, where you can pick a level and relax on the po

$699,900

5 beds2.5 baths5,206 sq ft

220 S Main St, Henderson, KY 42420

0.37 acre lot • 2 garage spots • Somewhat walkable

23 Lett Ct, Henderson (ky), KY 42420
23 Lett Ct, Henderson (ky), KY 42420
23 Lett Ct, Henderson (ky), KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
This 2-bedroom, 1-bathroom property is a diamond in the rough—perfect for investors or renovators looking to add value and maximize returns. Situated in a desirable neighborhood with strong rental demand, this home offers solid bones and a functional layout, ready for your vision and improvement. Highlights include: Two well-proportioned bedrooms, Spacious living area with natural light, Original kitchen and bathroom, generous lot size with potential for landscaping or expansion, off-street parking and storage options. With some TLC, this property could be transformed into a high-yield rental or a profitable flip. Whether you're a seasoned investor or a first-time buyer with renovatio

$62,000

2 beds1 bath1,140 sq ft

23 Lett Ct, Henderson (ky), KY 42420

5,663 sq ft lot • Car-dependent

Property at 10281 Old Highway 60 West, Henderson, KY 42420, 4 beds, 3 baths

$499,000

4 beds3 baths3,834 sq ft

10281 Old Highway 60 West, Henderson, KY 42420

Property at 104 Jackson St, Henderson, KY 42420

$265,000

— beds— baths— sq ft

104 Jackson St, Henderson, KY 42420

Property at 1608 S Main St, Henderson, KY 42420, 3 beds, 1 bath

$230,000

3 beds1 bath1,422 sq ft

1608 S Main St, Henderson, KY 42420

Property at 1515 Smith Ct, Henderson, KY 42420, 3 beds, 2 baths

$219,900

3 beds2 baths1,800 sq ft

1515 Smith Ct, Henderson, KY 42420

Property at Theodore Plan, Henderson, KY 42420, 3 beds, 2 baths

$215,000

3 beds2 baths1,310 sq ft

Theodore Plan, Henderson, KY 42420

Listing provided by Zillow

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Nearby homes that match your criteria

1834 Old Madisonville Rd, Henderson, KY 42420
1834 Old Madisonville Rd, Henderson, KY 42420
1834 Old Madisonville Rd, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Brand new construction in Creekside Condos! This 3 bedroom, 2 bath offers all the luxuries of easy living. Featuring no steps, this one level is all about ease and comfort. With everything being brand you, you can be the first one to cook in this kitchen or the first one to shower in the bathroom. The main living areas feature LVP flooring, while the bedrooms feature carpet. The kitchen is crisp and clean with brand new white cabinets, new SS kitchen appliances, and trendy neutral Formica countertops. One bathroom is a full shower/tub combo while the primary suite bathroom is a stand-up shower surround with a seat. Rest easy with a brand new roof, HVAC, and water heater.

$209,900

3 beds2 baths1,034 sq ft

1834 Old Madisonville Rd, Henderson, KY 42420

2 garage spots • Car-dependent

344 Glover Dr, Henderson, KY 42420
344 Glover Dr, Henderson, KY 42420
344 Glover Dr, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Check out this move-in ready, updated 3 bedroom home! The best part is that you get TWO lots with this purchase, as the empty lot to the right of the house is included, so you have plenty of space at . 52 acres in total with this affordable home situated on the corner lot. Upon arriving, you will be greeted by a huge front porch that is just waiting to be staged with the latest exterior furniture that is perfect for relaxing after a long day with the shade tree. A craftsman style front door, newer vinyl siding, a back ramp for convenience, and newer exterior doors are a few of the updates you’ll find on the exterior. Inside, you will see the entire interior has been updated, featuring

$129,900

3 beds1 bath864 sq ft

344 Glover Dr, Henderson, KY 42420

0.52 acre lot • Garage • Car-dependent

135 S Alvasia St, Henderson, KY 42420
135 S Alvasia St, Henderson, KY 42420
135 S Alvasia St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Welcome to your new home on the hill! This charming, sunny yellow residence features the most welcoming wraparound front porch and beautifully maintained property. Inside, you’ll find a large updated kitchen, hardwood floors and newly carpeted bedrooms. The home offers two full bathrooms and three bedrooms, as well as a versatile bonus room that could be used as a fourth if desired. The 18x36 garage includes enough space for a workshop area, storage, and covered parking for multiple vehicles. Off-street parking is abundant with alley access behind the home and a large driveway for additional parking. Enjoy the peace of mind with a new roof and gutters. Don’t miss out on this cha

$219,900

3 beds2 baths1,849 sq ft

135 S Alvasia St, Henderson, KY 42420

8,000 sq ft lot • 2 garage spots • Somewhat walkable

328 N Adams St, Henderson, KY 42420
328 N Adams St, Henderson, KY 42420
328 N Adams St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Investment Opportunity: 5-Plex in Prime Henderson, Ky Location. This rare opportunity 5-plex features 4 spacious 3-bedrooom 2-bath units that are 1144 sq ft each and a 1 2-bedroom, 1 bath unit that is 900 sq ft. The current rents are below market, offering strong upside potential. The roof is only 8 years old. One unit is updated and another has been completely remodeled. All contain washer/dryer hookups. Located just off 41-A in Henderson, KY. this property is conveniently close to shopping, dining, Interstate 69 and the Audubon Parkway. Great opportunity and all currently rented.

$495,000

7 beds3 baths5,476 sq ft

328 N Adams St, Henderson, KY 42420

0.41 acre lot • Somewhat walkable

1963 Springfield Dr, Henderson, KY 42420
1963 Springfield Dr, Henderson, KY 42420
1963 Springfield Dr, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
GET READY FOR SUMMER with this 3 bedroom, brick home with inground pool! Large detached 2-car garage with its own full bath convenient to the pool area. Privacy fenced backyard. Big eat-in kitchen and separate laundry room.

$170,000

3 beds2 baths1,107 sq ft

1963 Springfield Dr, Henderson, KY 42420

0.27 acre lot • 2 garage spots • Pool

104 S Ingram St, Henderson, KY 42420
104 S Ingram St, Henderson, KY 42420
104 S Ingram St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Are you looking for a great investment opportunity or possibly your first home? If so, this one might be for you. .. Updates since 2015 include: HVAC, water heater, flooring, paint, dishwasher and range/oven. Don't miss out!

$119,900

3 beds1 bath1,170 sq ft

104 S Ingram St, Henderson, KY 42420

3,000 sq ft lot • Somewhat walkable

Property at 917 Washington St, Henderson, KY 42420, 3 beds, 1 bath

$105,000

3 beds1 bath1,184 sq ft

917 Washington St, Henderson, KY 42420

Property at 308 S Bentley Dr, Henderson, KY 42420, 4 beds, 2.5 baths

$419,800

4 beds2.5 baths— sq ft

308 S Bentley Dr, Henderson, KY 42420

Property at 1610 Powell St, Henderson, KY 42420, 2 beds, 1 bath

$30,000

2 beds1 bath1,164 sq ft

1610 Powell St, Henderson, KY 42420

Property at ~6600 Pruitt Agnew Road (hwy 1217), Henderson, KY 42420

$4,000,000

— beds— baths— sq ft

~6600 Pruitt Agnew Road (hwy 1217), Henderson, KY 42420

Property at 1016 Washington St, Henderson, KY 42420

$7,000

— beds— baths— sq ft

1016 Washington St, Henderson, KY 42420

Average home prices near Henderson South Side, KY

Cities

Neighborhoods

Henderson North End homes for sale
$349,900

Henderson South Side, KY real estate trends

All Home Types trends in Henderson South Side, KY

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$176,250

+11.6% YoY | May 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

May 2025

Growth

% YoY

Henderson South Side, KY

$176,250

+11.6%

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