Recently Listed Open House 10/4 2pm - 4pm
401 Winding Way
Shelbyville, KY, 40065 $ 399,000
Bedrooms4 Baths2.0 Sq 3,111 Monthly Estimate*
$ 2,519
for $399,000 with 4 bedrooms and 2 full baths. This 3,111 square foot home was built in 1980 on a lot size of 0.5.
**FIRST SHOWINGS AT OPEN HOUSE, SUNDAY, OCTOBER 4, 2-4 PM** Be THE FIRST to see this beautifully upgraded home and be settled in before the holidays. Tucked on a half-acre lot backing to private woods, this 4-bedroom, 2-bath home has been lovingly updated from top to bottom, so all that's left to do is move in. Gather family in the formal living and dining rooms, framed by custom draperies and made for holiday dinners. Cook with joy in the remodeled kitchen with custom shaker cabinets, granite countertops, a pantry with slide-out shelves, and stainless appliances that stay. Then settle into the showstopping great room, where a brick wood-burning fireplace and vaulted tray ceiling with in-wall 7.2 surround sound create the ultimate spot for cozy nights, movie marathons, and game days. The primary bedroom impresses with a barrel-stave feature wall and a spacious walk-in closet (custom shelving), and the newly finished lower level adds a fourth bedroom, sitting area, and laundry. Both baths were remodeled within the past year with gorgeous floor-to-wall tile, and the hall bath's deep soaking tub is your personal retreat. Step outside to your own backyard escape: a sparkling pool with surrounding deck, plus a large deck (Trex decking) and patio overlooking the trees, perfect for summer parties or quiet mornings. New laminate floors, LED lighting, and an extra-deep, extra-wide two-car garage add everyday ease. Best of all, the big-ticket items are done: HVAC within 8 years, roof and windows within 10 (windows have a transferable warranty), water heaters (2) within 3, and A BRAND-NEW ELECTRIC PANEL. Homes this cared for don't last. See it Sunday, it may be gone Monday....
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Open House
10/4/2026 2:00 PM - 4:00 PM
401 Winding Way Shelbyville, KY
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesGeneralHeating Heat Pump
Cooling Central Air
Utilities Electricity Connected
Roof Shingle
HOA Fee 0
Garage Spaces 2
Architectural Style Ranch
Construction Materials Brick Veneer
Year Built 1980
Stories Count 1
Property Subtype Single Family Residence
County Shelby
Property Type Residential
HOA false
Attached Garage true
Subdivision Name ROLLING HILLS
Garage Y/N true
Total Rooms 12
Full Baths 2
Status Active
Directions I-64 E exit 35 North on Hwy 53 (Mt. Eden Rd) Right on US 60 E (Frankfort Rd) past high school left into Rolling Hills (next to church) right on Winding Way to YOUR new home!
City Shelbyville
MLS Area 30-Shelby County
Lot Size Units Acres
Lot Size Square Feet 21780
MLS Area Minor 30-Shelby County
Standard Status Active
Tax Lot 37
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InteriorBasement Walkout Finished
Total Fireplaces 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Above Grade Finished Area 1603
Half Baths 0
Total Bedrooms 4
Below Grade Finished Area 1508
Total Baths 2
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ExteriorFencing None
Parking Features Attached Entry Side Lower Level Driveway
Lot Features See Remarks Cleared
Water Source Public
Lot Size Area 0.5
Foundation Details Poured Concrete
Building Area Total 1603
Lot Dimensions 000
Lot Size Acres 0.5
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* Excluded FeaturesList Bymelissa@lapinskyrealty.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $2,519
- Monthly Property Taxes
- --
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Shelbyville, KY
Average List Price $460,165
Percent of Sale Price 15%
About Shelbyville, KY 15,735 Population
44% Since 2002
$ 45,401 Median Income
36.27 Median Age
35% Households with Children
Trends Information provided by ATTOM Data Solutions.
0 Elementary School
0 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 9/30/2026 | $399,000 | | Listed Price |