Neighborhood · Winter Park, Florida
Kenilworth
Established Winter Park living, minutes from downtown Orlando
9
Homes for sale
$1,275,000
Median list price
—
Avg price / sqft
—
Median days on market
Kenilworth sits in the heart of Winter Park, an Orange County community known for tree-lined streets, walkable pockets, and quick access to the city's cultural core. It's the kind of place where mature landscaping and settled neighborhoods carry the character, with nearby Lake Killarney, Hannibal Square, and Winter Park Pines rounding out the area. Downtown Orlando is roughly 18 minutes away, and Orlando International Airport about 32, so you're connected without living in the middle of the noise.
For buyers, the market here reads as small and premium. There are 10 active listings right now with a median list price of $1,160,000, which puts Kenilworth firmly in the upper tier of Winter Park real estate. With limited inventory and no recorded sales in the past year, this is a neighborhood where the right home doesn't come around often — worth watching alongside nearby Winter Park homes for sale and pockets like Eastbrook.
Kenilworth is a community in Winter Park, Florida.
Quick facts
Drive times
On the market now
Homes for sale in Kenilworth
$594,500
2010 SUMMERFIELD ROAD, WINTER PARK
3 bd · 2 ba · 1,889 sqft
$3,500,000
1836 WHITEHALL DRIVE, WINTER PARK
5 bd · 6.5 ba · 4,168 sqft
$1,275,000
2015 SUMMERFIELD ROAD, WINTER PARK
4 bd · 4 ba · 3,024 sqft
$695,000$719,000
2215 WOODCREST DRIVE, WINTER PARK
4 bd · 2 ba · 1,688 sqft
$2,099,990$2,199,000
525 S LAKEMONT AVENUE, WINTER PARK
4 bd · 3.5 ba · 3,330 sqft
$1,888,888$1,988,888
2032 KIMBRACE PLACE, WINTER PARK
5 bd · 4 ba · 3,382 sqft
$1,045,000
616 BRECHIN DRIVE, WINTER PARK
4 bd · 4.5 ba · 2,638 sqft
$625,000$650,000
1946 STRATHAVEN ROAD, WINTER PARK
4 bd · 2 ba · 2,102 sqft
$2,829,000
609 S PHELPS AVENUE, WINTER PARK
5 bd · 4.5 ba · 4,018 sqft
Every active listing inside the Kenilworth boundary
Open full map search →The numbers that matter
The Kenilworth market
Kenilworth vs Winter Park
Median list price
Median sold price — 3-yr, 3-mo rolling
▲ 12.6% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Kenilworth boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Kenilworth is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Kenilworth home
≈ $8,097/mo
$1,275,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
1,151
Median age
44
Median income
$131,286
Median home value
$564,647
Beyond the listings
Living in Kenilworth
Hobbies & Interests
Top 3% in the U.S.Dog Lovers
Pups are just another member of the family. Dog lovers adore their tail-wagging friends and are looking for new ways to make them happy.
Hobbies & Interests
Top 4% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Emotional
Top 7% in the U.S.Happy Place
Expressing feelings of safety, comfort and happiness - especially with loved ones.
Active
Top 14% in the U.S.Outdoor Adventures
Appreciating the outdoors, this population wants to actively engage with nature. Whether it's finding a new hiking trail or looking for the perfect spot to catch the sunset, they seek to explore the world around them.
Relationships
Top 15% in the U.S.Dating Life
With dating comes highs, lows, and lots of questions. You can find this population talking about dating advice, breakups and how to express their feelings.
Relationships
Top 18% in the U.S.Connected Motherhood
Motherhood is a unique journey for every woman. There are highs, lows,and lots to celebrate. These moms seek to share their experiences and engage with a community of moms.
People who close here
Our Winter Park experts
Keep exploring
More Winter Park neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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