1049 N KENTUCKY AVENUE, WINTER PARK, FL 32789
FAIRBANKS PARK · Orange County
Key Facts
Description
Experience the ultimate in modern Winter Park living in this **fully furnished, European-inspired 3-bedroom residence**, designed by award-winning architect **Phil Kean** and crafted for those who demand style, convenience, and performance. This rare long-term rental offers a seamless blend of luxury and functionality, featuring a **professional-grade gym with high-end equipment**, expansive **indoor–outdoor living**, and a private **two-story courtyard** that floods the home with natural light. Floor-to-ceiling glass doors open completely to create a true resort-style environment, complemented by a glass-wall staircase, premium wood finishes, quartz surfaces, and stainless steel appliances. The oversized primary suite delivers a spa-level retreat with a generous walk-in closet, while the secondary bedrooms provide exceptional comfort and storage. Located in one of Winter Park’s most coveted walkable pockets, you’re steps from Park Avenue, the Farmers Market, parks, sports fields, the library, and everyday conveniences — with I-4 just minutes away for effortless access to Downtown Orlando. With **no HOA**, architectural pedigree, curated furnishings, and a lifestyle unmatched in the rental market, this home is ideal for corporate relocations, professionals, and anyone seeking a sophisticated, low-maintenance living experience in the heart of Winter Park.
Property Information
Property Type
Residential Lease
Sub-Type
Townhouse
Year Built
2017
Stories
2
Living Area
2,741 sq ft
Lot Size
0.07 acres
Garage Spaces
2
Days on Market
19
MLS® Listing#
O6373029
Property Features
Appliances
Cooling
Heating
Parking
Laundry
Community
Financial Details
HOA
None
Parcel Number
12-22-29-2556-02-100
Directions
From Fairbanks follow to right on Denning, then right on S Kentucky.
Affordability Calculator
$1,200
Estimated monthly payment
$32/mo
Principal $4,800 · Est. interest $6,696 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in WINTER PARK, FL
- $380,413
- Median Listing Price
- 77
- Median Days on Market
- 1,673
- Median Sq Ft
- $221
- Median Price / Sq Ft
- 3,284
- Active Listings
- This home’s price is 98% below the area median.
- Its price per sq ft is 99% below the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in WINTER PARK, FL.
Location
Points of Interest in WINTER PARK, FL
Showing the WINTER PARK area map.
Nearby Schools
Keya Academy
School · 0.4 mi away
17吃瓜网
School · 0.4 mi away
51爆料
School · 0.4 mi away
Winter Park 9th Grade Center
School · 0.4 mi away
Park Maitland School
Elementary · 0.7 mi away
Park School
Elementary · 0.7 mi away
Circle Christian School
School · 0.8 mi away
Methodist School for Early Education
School · 0.9 mi away
St Margaret Mary Catholic Church
School · 1.0 mi away
Killarney Elementary School
Elementary · 1.2 mi away
Champions at Killarney Elementary
Elementary · 1.2 mi away
Childrens Academy
School · 1.3 mi away
Orlando Junior Academy
Elementary · 1.4 mi away
Park Maitland School
Elementary · 1.6 mi away
Spring Education Group
School · 1.6 mi away
Bishop Moore Catholic High School
Secondary · 1.7 mi away
St Charles Borromeo Catholic School
School · 1.8 mi away
Morning Star School
School · 1.9 mi away
Ocps Hospital Homebound
School · 1.9 mi away
Celandine Life-Prep Academy
School · 1.9 mi away
Commute Calculator
Nearby Homes
Similar Homes Nearby
Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 660 FANNING DRIVE, WINTER SPRINGS, FL | $4,200/mo | 6 | 5 | 4,172 |
| 1570 NE 30th Place, Oakland Park, FL | $4,200/mo | 2 | 2 | 1,942 |
| 1450 JUNIPER HAMMOCK STREET, WINTER GARDEN, FL | $4,200/mo | 6 | 4 | 4,194 |
| 4530 SW 25th St, West Park, FL | $4,200/mo | 4 | 2 | 1,388 |
| 8009 HAMPTON COURT, UNIVERSITY PARK, FL | $4,400/mo | 3 | 3 | 2,158 |
| 648 FITZWALTER DRIVE, WINTER PARK, FL | $4,400/mo | 3 | 2 | 1,554 |
Moving Cost Estimate
EXIT Agents in WINTER PARK
Listing Courtesy: THE AGENCY FL - 407-335-4119
Last Updated: 2026-01-12