Kenilworth Shores is a neighborhood in east Winter Park, in the 32792 zip code, built mostly in the 1950s. Homes are block and stucco, predominantly single story. Most homes fall between about 1,400 and 3,000 square feet under air, the median lot is roughly a quarter acre, and a two car garage is standard.
Kenilworth Shores has an optional homeowners association rather than a mandatory one, so there is no deed restricted membership to inherit. Dues run about $30 annually for those who join. Confirm the position on a specific parcel before relying on it.
Winter Park High School sits inside the subdivision.
The neighborhood was platted in eight secs, which is why listings appear under Kenilworth Shores, Kenilworth Shores Sec 1, Sec 02, Sec 03, Sec 04, Sec 05, Sec 06 and Sec 07. They are one community and they trade as one market.
What the homes are
Built Mostly built in the 1950s, with homes from 1936 to 2027.
Construction Block and stucco. Shingle roofs are near universal.
Style Ranch, Traditional. Predominantly single story.
Size Most homes fall between about 1,400 and 3,000 square feet under air.
Bedrooms Three bedrooms is the most common plan, then four.
Garage A two car garage is standard.
Lot The median lot is roughly a quarter acre.
HOA Optional rather than mandatory, so there is no deed restricted membership. Dues run about $30 annually for those who join. Confirm on a specific parcel before relying on it.
Where Kenilworth Shores is
Kenilworth Shores, centered at 28.588935, -81.326247. Drag to explore.Street level, inside the neighborhood. Drag to look around.
Drive times below are measured on the road network from the center of Kenilworth Shores, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.
Driving to
Time
Miles
Downtown Orlando
21 min
6.2
Walt Disney World
37 min
28.7
Orlando International Airport
30 min
12.1
Universal Orlando
29 min
16.7
Public schools nearby
Winter Park High School 4 min, 0.9 mi
Brookshire Elementary School 4 min, 1.0 mi
Winter Park High School, South Gate (Baldwin Park) 6 min, 1.6 mi
Lakemont Elementary School 5 min, 1.4 mi
Private schools nearby
Christian Education at Woodruff Academy 5 min, 1.3 mi
Parks and recreation
Ward Park 2 min, 0.5 mi
Windsong North Shore Park 4 min, 1.0 mi
Ward Park Loch Lomond Trail 3 min, 0.8 mi
Marvin Smiley Park 3 min, 0.9 mi
Groceries and errands
Sprouts Farmers Market 4 min, 1.1 mi
Publix Super Market at Aloma Shopping Center 5 min, 1.4 mi
Nearest is not the same as zoned. The schools above are the closest ones to Kenilworth Shores by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.
Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Kenilworth Shores actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 25 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.
What homes sold for in Kenilworth Shores
$689,000Median sale price
$418Median per square foot
7 daysMedian days to contract
25Homes sold in 12 months
Sale prices ran from $450,000 to $2,475,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
By size
Home size
Sales
Median price
Median $/sq ft
Median days
Under 2,000 sq ft
16
$604,000
$407
4 days
2,000 to 3,000 sq ft
6
$822,000
$367
14 days
3,000 sq ft and up
3
$2,285,000
$588
118 days
Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.
What a pool is worth here
Homes with a private pool sold at a median $431 per square foot against $369 without one, a difference of $63 per square foot. That comes from 13 sales with a pool and 12 without.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Never reduced 17 sales, closed at 100% of asking3 days
Reduced at least once 8 sales, closed at 98% of the reduced price92 days
Sellers who priced correctly and held their number went under contract in a median 3 days. Sellers who had to reduce took 92 days and still closed at 98% of their already reduced price, after a typical cut of $47,500. Opening high costs time and money, in that order.
Seller concessions
20%Of sales included a seller credit
$5,000Typical credit when there was one
5 of 25Sales carrying a credit
A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.
How buyers paid
Conventional 13 sales52%
Cash 11 sales44%
Private 1 sales4%
Cash was 44% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.
Questions about a specific home in Kenilworth Shores, or want to know what yours would sell for? Call or text Brenden Rendo at 407-616-9019 or send a message.
About this data. Source is the Stellar MLS feed for Kenilworth Shores in Winter Park, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. 5 records were excluded as off-market transfers rather than open market sales. Data believed accurate but not guaranteed; listings and closings change daily.
