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408 S Winter St

Summer view. All yard maintenance is included in rental fee. This is the "front" facing S. Winter St.
Side view; note side yard, fenced in back yard with privacy arborvitae trees.
Summer view; all yard maintenance included in rental fee. Porch view is of pasture with plank fencing.
Close up of S. Winter (front) entrance. Main entrance with parking is from Charlie Lane. Full restored vintage front door with original glass allows light into front hallway.
View from Front/S. Winter entrance to back of house/kitchen - main hallway. Note restored original plank flooring.
Hall entry view from back to front of house. Note restored original plank flooring. Second bedroom entrance is on the left.
View from entrance from Charlie Lane, optional use of two car garage. Landlord's Woodworking Workshop located on the property.
Main entrance view from Charlie Lane, the "back" of the house where entrance is located. Ample parking. Backyard is fenced in (safe for pets). Option of two car garage available. Seasonal raised bed herb garden (see bourbon barrel planters).
Back entrance, "keeping room" from back deck. Converts to dining room for easy entertaining - two tables can be placed that expand with leaves to seat 6-8 each. Room can convert to TV room if Living room is used as 3rd bedroom/other. Photo - Feb decor.
View of keeping room from kitchen which is adjacent. Handmade cherry book cases store serving ware, books. Table expands with leaves to seat 6-8.
View from Kitchen of Keeping Room/Living Room entrance: pocket doors located in doorway to close off LR for privacy (if used as a 3rd bedroom). Buffet on right holds everyday place settings, serving ware for eight.
Panoramic view from living room entrance; pocket door can be closed for privacy between Keeping room/dinning room and Living Room if converted to a bedroom. Bourbon bar set up to the right.
Living area with ample closets. Period mantle; leather chairs and reclining love seat. Pocket door separates living area from Keeping Room/area for privacy. Ceiling fan.
View of Keeping room and back entrance from corner of Living room. Tables fold up, can be moved to accommodate different layout/use of area. Love seat is a recliner; chairs are vintage leather.
Living area view from corner door to hallway can be closed or left open depending on tenant's preference. Equine decor featuring Kentucky artists. Dog/pet friendly!
View from LR to Keeping Room/back entrance - to see room flow for entertaining.
View from corner of LR of Keeping Room, back entrance.
Panoramic view from back entrance of LR and Kitchen entrances to see space flow.
Panoramic view of kitchen with partial keeping room. Dining room table to right expands out to seat 8-10 guests. See view of Laundry/Mud Room and side entrance, off of Kitchen. Note glassware, Bybee serving dishes, cook books in bookcase.
Full kitchen view from Keeping Room: Island rolls and can be turned in any direction desired or stored discreetly in the Laundry area when not in use. Note two wall ovens to the right: upper high end convection/microwave oven, lower electric oven.
Full view of sink, dishwasher and coffee station.
Gourmet quality gas range/hood.
Refrigerator view with counter space.
View from Laundry/Mudd room of Kitchen and Keeping Rooms/ LR entrance.
Full sized stacking washer and dryer next to half bath/powder room. View from kitchen. Views of side porch entry with keypad lock. Note live edge shelf on right under cabinet.
Close up of Mud/laundry room (off side porch entrance): live edge counter for folding clothes, project work; rack for air drying clothing; storage. Storage space for kitchen rolling island underneath counter.
Half bath located off of laundry area and next to side porch entry.
View of main hallway from kitchen to front door - full guest bath, two bedrooms are located off of this hallway.
Full guest bath (tub/shower on left); ample storage.
Panoramic view of primary bedroom from hallway: ample storage. Queen sized vintage four poster bed. Seasonal decor included in furnishings - July 4th, Fall Keeneland Racing Season, Thanksgiving/Christmas, Spring - Keeneland/Derby Racing Season.
Panoramic view of primary BR with Spring/summer decor. Queen sized four poster bed. Black out curtains (light, sound). Ceiling fan.
View of primary bedroom entrance from hallway. Table to the left of door is a game table that can flex to other rooms for card, board games!
View of master bath suite from corner of primary bedroom: pocket doors located in doorway and close for privacy.
View from entrance of master bath. Low step shower to the right (not pictured).
Panoramic view of master bath area.
Private water closet with ample storage cabinets.
Master vanity with makeup mirror. Soaking tub area to the left.
View of soaking tub "alcove'. Peaceful, relaxing
Soaking tub cove.
Panoramic view of second (front) bedroom from hallway entrance. Original fire place; Kentucky artwork featured (Alan Brewer and Joseph Petro); sitting area and vintage wardrobe for ample storage. Black out curtains; queen sized bed; ceiling fan.
Panoramic view from front corner of bedroom - mirror/dresser; book shelves. Room can convert to office, game room or exercise room (bed flips up to store); table opens up and other furniture can be added per tenant's preference.
Panoramic view from front center of bedroom - mirror/dresser; book shelves. Room can convert to office, game room or exercise room (bed flips up to store); table opens up and other furniture can be added per tenant's preference.
View of hallway entrance of second bedroom. Queen sized bed. Bed flips up for storage to create an office or exercise/flex room.
Full bed view.
View of bed with door closed; book case to right of door.
  • Furnished

$4,000/ mo
Total price
Now includes required monthly fees in total price
2 beds2.5 baths1960 sqft house
Available July 16
408 S Winter St

Your booked tour

What you get

Dog-friendlyIn-unit laundryParkingAir conditioning

Costs, fees, and lease terms

Special offer!
Rental rate determined by final terms and length of lease.… Range of rent: $3800 - $6,000; base of $4000/mo. with 6 month lease. This period of time includes Keeneland Sales and Keeneland Racing season.

Lease terms

Mid term rental - rent set per final negotiated terms of lease. Range: $3800 - $6000 depending on final terms and length of lease. Fully furnished, Owner pays for all utilities/maintenance: Internet/Spectrum, water/sewer, garbage, and all yard maintenance. Tenant has option of partially furnished (classic equestrian/KY decor) or in special cases - totally unfurnished, cleaning services; grocery/stocking service. Optional use of two car garage.

Pricing comparison

$2000

At $4,000, this listing is priced $2000 more than the current market rate for a 2 bedroom home in Midway.

Pets

  • Dogs

    Allowed
    Number allowed1

  • Cats

    Not allowed

The neighborhood

About the building

Blacksmith Cottage Historic Furnished Rental in Midway, Kentucky Experience the charm of Kentucky horse country at Blacksmith Cottage, a beautifully… restored historic home in the heart of Midway, Kentucky. Ideal for a 3 - 6+ month lease, this fully furnished residence is perfect for professionals relocating to the area, those building or renovating a home, traveling healthcare professionals, equestrian enthusiasts, or anyone seeking an extended stay near Keeneland and Lexington. Available July 17, 2026 Property Highlights Lovingly renovated by local craftsmen, this historic 1890 cottage combines timeless character with modern comfort. The home offers approximately 1,960 square feet of living space, including: 2+ bedrooms with queen-sized beds 2.5 bathrooms Spacious living room Flexible dining room, entrance foyer, or "keeping room" Primary suite featuring a soaking tub and low-step walk-in shower 10-foot ceilings and oversized 9-foot windows throughout Original trim, period mantels, and fireplaces in each bedroom and living area Refinished original hardwood floors in living spaces and bedrooms High-quality waterproof flooring in kitchen, mudroom, and baths for easy maintenance Gourmet Kitchen & Comfortable Living The fully equipped gourmet kitchen features a gas range and three ovens, making it ideal for both everyday living and entertaining. The home is furnished in traditional Kentucky style with tasteful equestrian accents and artwork by Kentucky artists. A partially furnished option may also be available. Additional amenities include: Full-size stacked washer and dryer Abundant storage space 80-gallon water heater Excellent water pressure High-speed Wi-Fi Ample off-street parking Optional use of a two-car garage Outdoor Features Enjoy beautiful views of plank-fenced horse pastures from the front porch. The newly fenced backyard features attractive plank fencing with wire fill, creating a secure outdoor space for approved pets. Rent Includes All utilities High-speed internet/Wi-Fi All furnishings Basic kitchen and bath essentials Complete lawn and landscape maintenance This is a truly turnkey, stress-free home designed for professionals and others seeking a peaceful retreat in one of Kentucky's most desirable small towns. Exceptional Location Blacksmith Cottage is within a five-minute walk of the renowned Midway Bakery and just minutes from Wallace Station and the acclaimed Holly Hill Inn. The property is also conveniently located: A few blocks from downtown Midway and Midway University Approximately 20 minutes to Keeneland Race Course and Blue Grass Airport Easy access to I-64 and I-75 Convenient commute to Lexington, the University of Kentucky, Baptist Health Lexington, and Saint Joseph Hospital Approximately 12 minutes to Frankfort Approximately 1 hour to Louisville For outdoor enthusiasts, scenic Kentucky back roads are just outside your door, offering wonderful opportunities for cycling, walking, and enjoying the beauty of horse country. Leasing Information Non-smoking, tobacco-free property Pets considered on a case-by-case basis Zillow application preferred Tours provided to qualified applicants only Local ownership and professional management ensure responsive service and meticulous property care throughout your stay.

The property manager

Nearby schools

Students who live in 408 S Winter St attend the following Woodford County School District (Unified School District) public schools:

GreatSchools ratings are based on test scores and additional metrics when available.

408 S Winter St

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