Taylor Wood Retreat presents an exceptional opportunity in the heart of Kentucky's Bluegrass region. Over the past 12 months (June 18, 2024 to June 17, 2025), this property has generated $188,000 in short-term rental income and is projecting over $200,000 for the next 12 months, including a confirmed 2026 Kentucky Derby reservation worth $10,865. Offered fully furnished and turnkey, this 6-bedroom, 3.5-bath home offers 4,799 total finished square feet, including a walkout basement, all situated on 5 beautiful acres with a pond, fire pit area, and peaceful views. With an estimated 30% expense ratio, the current net income provides an 11% cap rate. Whether you're looking for a high-performing STR or a private retreat to call home, this property delivers. Located just 20 minutes from Louisville and minutes from the Outlets of the Bluegrass and Weissinger Hills Golf Course, the home blends rural charm with urban access. The seller is only parting with this high-performing asset to redeploy capital into revitalization projects in downtown Shelbyville, creating a rare chance for buyers to step into a proven income-producing property.
Sold for $1,136,000
$1,136,000
1416 Taylor Wood Rd, Simpsonville, KY 40067
6beds
4,799sqft
Single Family Residence
Built in 1985
5 Acres Lot
$1,164,500 Zestimate®
$237/sqft
$3,994 Estimated rent
Home value
$1,164,500
$850,000 - $1.61M
$3,994/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: September 10, 2025 at 10:17pm
Listed by:
Alex T Doyle 502-633-0220,
Torrey Smith Realty Co., LLC
Bought with:
Toni R Boer, 267827
Keller Williams Collective
Source: Metro Search Inc. LLC DBA Apex MLS,MLS#: 1688861
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 4
- Full bathrooms: 4
Primary bedroom
- Level: First
Bedroom
- Level: Second
Bedroom
- Level: Second
Bedroom
- Level: Second
Bedroom
- Level: Basement
Bedroom
- Level: Basement
Primary bathroom
- Level: First
Full bathroom
- Level: Second
Full bathroom
- Level: Basement
Dining room
- Level: First
Great room
- Level: First
Great room
- Level: Basement
Kitchen
- Level: First
Laundry
- Level: First
Heating
- Heat Pump
Cooling
- Central Air
Features
- Basement: Walkout Finished
- Number of fireplaces: 2
Interior area
- Total structure area: 3,083
- Total interior livable area: 4,799 sqft
- Finished area above ground: 3,083
- Finished area below ground: 1,716
Property
Parking
- Total spaces: 2
- Parking features: Attached, See Remarks
- Attached garage spaces: 2
Features
- Stories: 2
- Patio & porch: Deck, Porch
- Exterior features: See Remarks
- Has spa: Yes
- Spa features: Heated
- Fencing: Partial,Wood
Lot
- Size: 5 Acres
- Dimensions: 250 x 821
- Features: See Remarks
Details
- Parcel number: 01600063C
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Cement Siding, Wood Frame, Stone Veneer
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Year built: 1985
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Electricity Connected
Community & neighborhood
Location
- Region: Simpsonville
- Subdivision: None
HOA & financial
HOA
- Has HOA: No
Price history
| Date | Event | Price |
|---|---|---|
| 8/11/2025 | Sold | $1,136,000-6.5%$237/sqft |
Source:  Metro Search Inc. LLC DBA Apex MLS #1688861 Report a problem | ||
| 7/1/2025 | Pending sale | $1,215,000$253/sqft |
Source: Metro Search Inc. LLC DBA Apex MLS #1688861 Report a problem | ||
| 6/26/2025 | Price change | $1,215,000-0.3%$253/sqft |
Source: Metro Search Inc. LLC DBA Apex MLS #1688861 Report a problem | ||
| 6/17/2025 | Price change | $1,219,000-0.5%$254/sqft |
Source: Metro Search Inc. LLC DBA Apex MLS #1688861 Report a problem | ||
| 6/5/2025 | Listed for sale | $1,225,000+63.3%$255/sqft |
Source: Metro Search Inc. LLC DBA Apex MLS #1688861 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2023 | $5,001 +0.6% | $425,000 |
| 2022 | $4,974 +91.3% | $425,000 +97.7% |
| 2021 | $2,601 -0.3% | $215,000 |
Find assessor info on the county website
Neighborhood: 40067
Nearby schools
GreatSchools rating
- 6/10Simpsonville Elementary SchoolGrades: K-5Distance: 2.4 mi
- 3/10Shelby County West Middle SchoolGrades: 6-8Distance: 7.1 mi
- 4/10Martha Layne Collins High SchoolGrades: 9-12Distance: 5 mi
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$1,164,500
2% more
+$23,290
With Zillow Showcase(estimated)
$1,187,790
- Kentucky
- Shelby County
- Simpsonville
- 40067
- 1416 Taylor Wood Rd