Henderson South Side, KY homes for sale & real estate

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1201 O'byrne St, Henderson, KY 42420
1201 O'byrne St, Henderson, KY 42420
1201 O'byrne St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Welcome to this cozy 750 sq ft gem featuring beautiful hardwood floors throughout and a fresh new coat of paint with new light fixtures that brightens every room. This home offers a functional layout with two comfortable bedrooms and a full bathroom, ideal for starting your homeownership journey or adding to your investment portfolio. This property presents great potential for rental income or personal living, and will be sold in AS-IS condition.

$99,900

2 beds1 bath750 sq ft

1201 O'byrne St, Henderson, KY 42420

5,700 sq ft lot • Garage • Car-dependent

1228 Obyrne St, Henderson, KY 42420
1228 Obyrne St, Henderson, KY 42420
1228 Obyrne St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Welcome to this delightful 2-bedroom, 1-bath home, full of character and modern touches! Built in 1950 and crafted to stand the test of time, this 820 sq ft gem features beautifully preserved original hardwood floors and a recently painted interior that brings a fresh, inviting feel throughout. Enjoy abundant natural light streaming through every room, creating a warm and welcoming atmosphere. The updated roof offers peace of mind, while the spacious corner lot provides plenty of outdoor space for gardening, entertaining, or simply relaxing in your own private retreat. Perfect for first-time buyers, downsizers, or anyone looking for a move-in-ready home with vintage charm and modern reliabi

$98,000

2 beds1 bath820 sq ft

1228 Obyrne St, Henderson, KY 42420

6,780 sq ft lot • Car-dependent

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.

$134,900

2 beds1 bath750 sq ft

306 S Elm Pl, Henderson, KY 42420

4,648 sq ft 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

10281 Old Highway 60 West, Henderson, KY 42420
10281 Old Highway 60 West, Henderson, KY 42420
10281 Old Highway 60 West, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Welcome Home to this beautiful 4 bedroom (possibly 5 with large upstairs bonus room), 3 full baths brick home seated on almost an acre of land in the county. Includes large garden and beautiful courtyard with swing and decorative fish pond. Home includes a pristine attached 2 car garage and a 24x32 detached garage and shop for all of your toys! Fully tiled kitchen has an extra long bar/island with solid surface countertops and lots and lots of white cabinets. Includes a separate huge walk in pantry off of the hallway and a full bathroom conveniently located off of the kitchen hallway as well. Home has a large separate laundry room with built in cabinets and counter space for convenience. Ov

$489,000

4 beds3 baths3,834 sq ft

10281 Old Highway 60 West, Henderson, KY 42420

0.8 acre lot • 3 garage spots • Somewhat walkable

Property at 104 Jackson St, Henderson, KY 42420

$260,000

— beds— baths— sq ft

104 Jackson 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

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Nearby homes that match your criteria

NEW 9 HRS AGO

1927 Powell St, Henderson, KY 42420
1927 Powell St, Henderson, KY 42420
1927 Powell St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Adorable 2-bedroom, 1-bathroom home with lots of curb appeal! This well-maintained home offers a spacious living room with front bay window and eat-in kitchen with ample cabinet space. Outside features a nice size, new deck overlooking the partially fenced backyard and storage shed with loft space. Don't miss this affordable home in a great location near shopping, schools and restaurants.

$139,900

2 beds1 bath768 sq ft

1927 Powell St, Henderson, KY 42420

5,510 sq ft lot • Car-dependent

NEW 26 HRS AGO

18 S Julia St, Henderson, KY 42420
18 S Julia St, Henderson, KY 42420
18 S Julia St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Fixer-Upper Opportunity! This 2-bedroom, 1-bath home is full of potential and perfect for investors or first time home buyer. The updated kitchen, wood floors, and recently replaced roof and HVAC (just 3 years old) provide a solid foundation for your finishing touches. Situated on a nice-sized fenced lot, it also features a 1-car detached garage and a great backyard space. Washer & Dryer to remai. Home will need new windows and some repairs—will not qualify for FHA or VA financing. Cash or conventional financing only. Bring your vision and make this house your own!

$104,900

2 beds1 bath971 sq ft

18 S Julia St, Henderson, KY 42420

6,000 sq ft lot • Garage • Somewhat walkable

2055 Peggy Dr, Henderson, KY 42420
2055 Peggy Dr, Henderson, KY 42420
2055 Peggy Dr, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Calling all first-time home buyers and/or investors!!! This 3 bedroom home in Countryview Subdivision is ready for a new owner. Don't miss out on this opportunity. With hardwood flooring in the bedrooms and living room, there is a lot of orginal charm. There is a covered rear patio and a spacious back yard as well as a one-car attached carport. All of this can be yours for $119,900!

$119,900

3 beds1 bath1,131 sq ft

2055 Peggy Dr, Henderson, KY 42420

9,000 sq ft lot • Garage • Car-dependent

738 First St, Hendeson, KY 42420
738 First St, Hendeson, KY 42420
738 First St, Hendeson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Located just minutes from downtown Henderson, this income-producing 4-plex offers a solid opportunity for investors. Each unit features 1 bedroom and 1 bathroom. Three of the four units have been recently remodeled and are currently leased to tenants, providing immediate rental income. The fourth unit is vacant and ready for renovation—perfect for adding value and increasing future rental potential. Conveniently situated near shopping, dining, and major roadways, this property offers both long-term potential and short-term cash flow.

$225,000

3 beds3 baths2,640 sq ft

738 First St, Hendeson, KY 42420

2,795 sq ft lot • Somewhat walkable

23 Maple St, Henderson, KY 42420
23 Maple St, Henderson, KY 42420
23 Maple St, Henderson, KY 42420
ABOUT THIS HOME
Henderson South Side, KY Homes for Sale
Nice two-bedroom, one-bath home features an open kitchen and living room, lots of storage, and an unfinished basement. The large back lot is fenced in, and there’s a carport for parking. Move-in ready!

$114,000

2 beds1 bath624 sq ft

23 Maple St, Henderson, KY 42420

7,260 sq ft lot • Car-dependent

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

Property at 135 S Alvasia St, Henderson, KY 42420, 3 beds, 2 baths

$214,900

3 beds2 baths1,849 sq ft

135 S Alvasia St, Henderson, KY 42420

Property at 328 N Adams St, Henderson, KY 42420, 7 beds, 3 baths

$495,000

7 beds3 baths5,476 sq ft

328 N Adams St, Henderson, KY 42420

Property at 1963 Springfield Dr, Henderson, KY 42420, 3 beds, 2 baths

$153,000

3 beds2 baths1,107 sq ft

1963 Springfield Dr, Henderson, KY 42420

Property at 1137 Clay St, Henderson, KY 42420, 3 beds, 2 baths

$104,900

3 beds2 baths1,680 sq ft

1137 Clay St, 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 1524/1528 Roosevelt St, Henderson, KY 42420

$25,900

— beds— baths— sq ft

1524/1528 Roosevelt 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
$369,900

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)

$205,502

+30.1% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Henderson South Side, KY

$205,502

+30.1%

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