Neighborhood · Winter Park, Florida
Kenilworth
Established Winter Park living minutes from downtown Orlando
10
Homes for sale
$1,124,500
Median list price
$500
Avg price / sqft
41
Median days on market
Kenilworth sits in the heart of Winter Park, where mature tree canopy, pool-ready backyards, and a walkable pace define daily life. It's the kind of community where you can reach downtown Orlando in about 18 minutes yet come home to quiet streets near Lake Killarney and the shops around Hannibal Square. Families are drawn here in part for the assigned schools — Brookshire Elementary, Glenridge Middle, and Winter Park High.
For buyers today, this is a move-up market with real range. Ten homes are active right now, priced from $599,000 up to $2,995,000, with a median list of $1,130,750 — and half the available inventory crosses the $1M mark. Homes are moving in a median of 28 days and sellers are collecting about 98% of asking, so well-priced listings don't linger. If you're comparing options nearby, it's worth looking at Eastbrook and Winter Park Pines too.
Kenilworth is a community in Winter Park, Florida.
Quick facts
$599,000 – $3.0M price range
2,831 sqft median home
$3,400/mo median rent
30 sold in 12 months
Drive times
On the market now
Homes for sale in Kenilworth
$675,000
2322 WOODCREST DRIVE, WINTER PARK
4 bd · 2 ba · 1,650 sqft
$1,950,000
513 DUNRAVEN DRIVE, WINTER PARK
5 bd · 4.5 ba · 3,560 sqft
$2,990,000
532 LANGHOLM DRIVE, WINTER PARK
5 bd · 4.5 ba · 4,050 sqft
$675,000
2215 WOODCREST DRIVE, WINTER PARK
4 bd · 2 ba · 1,688 sqft
$629,000$639,000
508 BRECHIN DRIVE, WINTER PARK
3 bd · 2 ba · 1,783 sqft
$2,700,000
648 WORTHINGTON DRIVE, WINTER PARK
5 bd · 4.5 ba · 3,588 sqft
$599,000$625,000
1946 STRATHAVEN ROAD, WINTER PARK
4 bd · 3 ba · 2,102 sqft
$2,995,000$3,245,000
1836 WHITEHALL DRIVE, WINTER PARK
5 bd · 6.5 ba · 4,168 sqft
$1,250,000$1,262,500
2015 SUMMERFIELD ROAD, WINTER PARK
4 bd · 4 ba · 3,024 sqft
$999,000$1,045,000
616 BRECHIN DRIVE, WINTER PARK
4 bd · 4.5 ba · 2,638 sqft
Every active listing inside the Kenilworth boundary
Open full map search →Find your fit
Browse Kenilworth
By feature — on the live map
Where the market lives
The numbers that matter
The Kenilworth market
30
Sold, last 12 months
$706,500
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
4 days
Median time to sell
Kenilworth vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 1.4% 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
≈ $6,722/mo
$1,124,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$3,400/mo
Median rent
Homes for rent inside the boundary
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
Straight answers
Kenilworth FAQs
Is Kenilworth a good place to live?+
It's an established Winter Park community with tree-lined streets, pool homes, and quick access to downtown Orlando in about 18 minutes. The assigned schools — Brookshire Elementary, Glenridge Middle, and Winter Park High — are a major draw for families. You're also close to Lake Killarney and the dining and shops of Winter Park proper.
Is Kenilworth expensive?+
It skews upscale: the median list price is $1,130,750 and five of the ten active homes are priced above $1 million. That said, there's room at the entry point, with listings starting around $599,000, so it's not a single-price neighborhood.
What do homes cost in Kenilworth?+
Active listings run from $599,000 to $2,995,000 at a median of $1,130,750, averaging about $500 per square foot on a median home size of 2,831 square feet. Over the last 12 months, 30 homes sold at a median price of $706,500, which reflects a broader mix of what actually trades hands here.
How is the market in Kenilworth right now?+
It's active and efficient — homes sell in a median of 28 days and sellers are getting about 98% of their asking price. With only 10 homes on the market and 30 sold in the past year, inventory is tight enough that priced-right listings move quickly. If you want more options, Eastbrook is worth a look nearby.
What about HOA fees and property taxes?+
Most of Kenilworth isn't governed by a mandatory HOA, so there's no typical monthly dues figure to report. Property taxes run around $7,041 per year at the median, and the median rent in the area is about $3,400 a month if you're weighing renting versus buying.
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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