Kenilworth Shores Sec 1
Homes for Sale in Winter Park, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Kenilworth Shores Sec 1 is an older Winter Park pocket where price is driven by the house itself, not by a uniform product. With a build range spanning 1925 to 2024 and a median year built of 1958, you are comparing homes that have been renovated, expanded, or rebuilt against ones that are still largely original. That spread is why condition — not square footage alone — sets value here, and why the single median figure tells you less than the specific home in front of you.
The typical home is modest in footprint, with a median living area around 1,799 square feet, so a lot of value hinges on how well the space has been updated and reworked. For buyers, that means underwriting each property on its own merits and budgeting for the work an older home may need. For sellers, condition and updates are the lever you actually control, and they matter more here than they would in a uniform subdivision.
Kenilworth Shores Sec 1 right now
🔴 Off the recent peak. The trailing-12-month median ($627K) is down 14.4% from the prior 12 months ($732K) and up 142% since 2012. With about 18 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending July 15. Confidence: High (25 and 30 sales in the two windows).
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Updated July 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Kenilworth Shores Sec 1 market snapshot (as of July 15, 2026): the median sale price is about $627K ($396 per sq ft over the trailing 12 months of closed sales), and a median 5 days on market for closed sales. The trailing-12-month median is down 14% from the prior 12 months and up 142% since 2012, computed from record-level Stellar MLS closed sales (25 closings in the current window).
Kenilworth Shores Sec 1 is a community of 917 homes in Winter Park, Orange County, built between 1924 and 2024 (median 1961.0), with a median living area of about 1,900 square feet. 75% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a long-established Winter Park neighborhood of roughly 308 homes with a mix of vintage and rebuilt housing stock, where the story is variety and condition rather than a single standard floor plan.
Who Kenilworth Shores Sec 1 is best for.
Best for
- Buyers who want an established Winter Park location and will budget for updates on an older home
- Renovation-minded buyers comfortable underwriting a property by its condition rather than its list price
- Long-hold owner-occupants seeking a stable, largely owner-held neighborhood
Probably not for
- Buyers who need a turnkey, uniform new-construction product
- Shoppers relying on a single median figure to gauge value without a home-by-home review
- Buyers unwilling to compete for the occasional well-priced, well-maintained listing
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 15 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($627K) IS the median in the snapshot above, and the move from 2025 ($732K) IS the -14.4% one-year change.
Windows contain 1 to 43 sales each (25 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Deemed reliable but not guaranteed.
The Kenilworth Shores Sec 1 buying strategy.
If we were buying in Kenilworth Shores Sec 1 today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Kenilworth Shores Sec 1.
An older neighborhood that never stopped changing
The century-wide build range is the defining trait. A 1958 median tells you the core of the neighborhood is mid-century, but the presence of homes built as recently as 2024 means teardowns and rebuilds are part of the fabric. Expect to walk from an original cottage to a new-construction infill on the same street, which makes comparable analysis genuinely important before you make an offer.
About 70.5% of homes carry a homestead exemption, which points to a neighborhood held largely by owner-occupants rather than dominated by rentals or turnover. That kind of ownership stability tends to show up in maintained yards and long-held homes, but it also means well-priced, well-condition listings can be less frequent — patience and preparation matter when the right one surfaces.
The location and the amenities are priced into every listing in Kenilworth Shores Sec 1. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Kenilworth Shores Sec 1 buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (6.9). Basis: Long-Term Appreciation +142% since 2012; Recent Direction -14.4% year-over-year; Owner Commitment 75% owner-occupied; Pricing Power 98.6% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a neighborhood this varied, the median price is a starting point, not an answer. We underwrite each home on its own condition, vintage, and updates, and we will tell you plainly when a listing is priced for a renovation it has not had. Whether you are buying or selling, that home-by-home discipline is where the real numbers get made.
Kenilworth Shores Sec 1 in 15 seconds.
HOA, CDD & Fees
- Mandatory HOA — confirm current dues
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Kenilworth Shores Sec 1 buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Kenilworth Shores Sec 1 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Kenilworth Shores Sec 1, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Kenilworth Shores Sec 1 home worth?
Get a no-obligation home value based on real comparable sales in Kenilworth Shores Sec 1, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Kenilworth Shores Sec 1?
How long do homes in Kenilworth Shores Sec 1 take to sell?
How many homes are in Kenilworth Shores Sec 1?
What share of Kenilworth Shores Sec 1 is owner-occupied?
When were the homes in Kenilworth Shores Sec 1 built?
Do cash buyers compete in Kenilworth Shores Sec 1?
Have Kenilworth Shores Sec 1 home prices gone up?
Who is the best real estate agent for Kenilworth Shores Sec 1?
How do I find a top Winter Park real estate agent who knows Kenilworth Shores Sec 1?
Can Momentum Realty connect me with an agent for Kenilworth Shores Sec 1?
Should you buy in Kenilworth Shores Sec 1?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 15, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (19 streets, ZIP 32789/32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2004 (345 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.
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