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1416 Castlewood 1416 Castlewood
1416 Castlewood Living room
1416 Castlewood Dining room
1416 Castlewood Kitchen
1416 Castlewood Kitchen
1416 Castlewood Media room
1416 Castlewood Rear patio with gas grill
1416 Castlewood Third-floor living area
1416 Castlewood Master bedroom
1416 Castlewood Bedroom 2
1416 Castlewood Bedroom 3
1416 Castlewood Bedroom 4
1416 Castlewood Bedroom 5
1416 Castlewood Master bathroom
1416 Castlewood Master bathroom
1416 Castlewood Second-floor full bath
1416 Castlewood Third-floor full bathroom

1416 Castlewood, Highlands

This historic five-bedroom, three-bath Highlands home has more than 4,000 square feet and overlooks Fredrick Law Olmsted’s Tyler Park, just a few blocks from the fun dining and nightlife of Bardstown Road.

It features a sunny remodeled kitchen, master suite, and renovated master bath with heated marble floors. There is also a guest suite on the third floor with a living room, flat-screen TV, and full bath.

The house sleeps up to 10 people:

  • second-floor master with king-sized bed and renovated master bath with heated marble floors
  • three other second floor bedrooms, each with a queen-sized bed
  • another full bath on the second floor as well as a laundry room
  • third floor guest suite with a double bed, living room with flat-screen TV, and full bath

Other features

  • formal dining room
  • formal living room
  • media room with flat-screen TV
  • renovated, modern eat-in kitchen with new stainless appliances
  • quiet backyard patio with furniture and gas grill
  • off-street parking


  • minutes from Louisville International Airport
  • minutes to Churchill Downs
  • short walk to Bardstown Road
  • across the street from historic Tyler Park
  • short walk to Value Market Grocery
  • short walk to Baxter Avenue Theatres


  • rental agreement required
  • $10,000 for three nights (Thurs., May 3 at noon to Sun., May 6 at noon)
  • $300 cleaning fee
  • 50 percent non-refundable deposit due at signing, remaining due 30 days prior to the Derby with a $2,000 refundable damage deposit
  • non-smoking only
  • no pets
  • no house parties
  • for more information, please contact Kevin at or 502-396-6919

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