1407 Winter Ave, Highlands

A Derby Dream in the Historic Highlands – 1407 Winter Avenue

Welcome to the Derby Dream Home nestled in the Original Highlands of Louisville, KY. You’ll love this spacious, equestrian-themed, 120 year old historic Sears Catalog House with intricate woodwork and stained glass accents; oozing Southern Charm. With sleeping accommodations for six, you’ll have plenty of time and space to enjoy the races, relax, and take in the culture of Louisville. A leisurely five-minute walk will find you at some of the best restaurants and nightlife in the city.

Home Features:

Main floor

Detached 2 Car Garage and Parking Pad for 4 Vehicles
Guest Bedroom with Four Poster Queen Bed
Full bathroom with Clawfoot Tub
Formal Living Room with Steinway Grand Piano and Art Deco Fireplace
Formal Dining Room with seating for 6
Game Room with Billiards Table and Upright Arcade with multiple games (PacMan, Frogger, Mario, etc)
Renovated Kitchen with Stainless Steel Appliances and Coffee Bar (seats 2)
Cozy Movie Room with Surround Sound
Private Back Yard with Fence and Patio Seating for 10
ADT Security System and Outdoor Google Nest Cameras

Second floor

Master bedroom with King Bed
Guest Bedroom with Queen Bed
Full Bathroom

Location:

Situated in the Original Highlands Neighborhood of Louisville, either walking distance or just minutes away from attractions, including:

5 minutes to Downtown

Churchill Downs: Less than 5 miles to the Track and Kentucky Derby Museum

Walking Distance to Bardstown Road Nightlife and Restaurants: Jack Fry’s, The Holy Grale, Ramsi’s Café on the World, O’Sheas Irish Pub, Quills Coffee, Neat Bourbon Bar, and many more

Urban Bourbon Trail: Less than 2 miles to bourbon staples such Old Forester, Michter’s, Peerless, Evan Williams, Angel’s Envy, Rabbit Hole, Copper & Kings, Whiskey Thief, and many more

Germantown Nightlife and Restaurants: Shop Bar, Full Stop Station, The Fish House, Perso, Nord’s Bakery, and many more

Paristown Point Restaurants: The Café, Jeff’s Donuts, Wiltshire Pantry

NULU Restaurants and Shopping: Lou Lou on Market, Guacamole, Mayan Café, Red Tree Gifts, and many more

Louisville Slugger Museum: 2 Miles

Muhammad Ali Center: 2 Miles

5 miles to Louisville International Airport

Whether you’re here for the Kentucky Derby, Breeder’s Cup, a Bourbon Trail adventure, or a long weekend to enjoy Louisville’s hospitality, the Derby Dream Home is your perfect getaway spot.

Terms:

Guests will have access to the entire house (with the exception of Master Closet and Office) and private fenced backyard. You’ll receive a set of keys, garage door opener, WiFi password, and code for the ADT security system should you wish to use it.

$4500 Thursday thru Sunday of Derby Week
Check-in: 3 PM Thursday (flexible upon request)
Check-out: 1PM Sunday (flexible upon request)
$1000 per additional night
Home is available Monday thru Monday of Derby Week
$2000 non-refundable booking deposit in order secure your booking, balance due two weeks prior to arrival: Cash, Check, or Zelle
$1000 refundable security deposit due on arrival and will be returned provided there is no significant damage to the house: Cash, Check, or Zelle
Also available for Breeders Cup and Bourbon Trail Adventures – contact Jordan (contact info below)
Concierge Services Available on Request

House Rules: