269 E CANTON AVENUE UNIT 269, WINTER PARK, FL, 32789
Active64 days on marketListed May 21, 2026MLS #O6404706
About this home
269 E CANTON AVENUE UNIT 269
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.
Facts & features
The home at a glance
1
Bedrooms
1.5
Bathrooms
1,109
Sqft
0.03 ac
Lot size
1971
Year built
Three Or More
Levels
$892
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$7,199 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$7,199/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs Winter Park actives
$892 vs $343
Days on market
64 vs 34 typical
Where $892/sqft sits among the 316 Winter Park actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Winter Park
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
WINTER PARK 32789 — neighborhood snapshot
Population
26,884
Median age
44.4
Median income
$100,213
Median home value
$695,000
Avg household
2.13
Households w/ children
2,125
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$473K → $500K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
149 of 316
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 16% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 269 E CANTON AVENUE UNIT 269
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$632,100
225 E CANTON AVENUE UNIT 225 · same community
2 bd · 2 ba · 1,057 sqft · $598/sqft · 117 DOM
Sold · Feb ’26$586,000
265 E CANTON AVENUE UNIT GE · same community
2 bd · 2 ba · 1,057 sqft · $554/sqft · 83 DOM
Sold · Jun ’26$612,500
259 E CANTON AVENUE UNIT 259 · same community
2 bd · 2 ba · 1,040 sqft · $589/sqft · 45 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 269 E CANTON AVENUE UNIT 269 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 269 E CANTON AVENUE UNIT 269 — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
269 E CANTON AVENUE UNIT 269 FAQs
What would the monthly payment be for 269 E CANTON AVENUE UNIT 269?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $7,199/mo — principal and interest, the actual property-tax bill, the $1,039/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 269 E CANTON AVENUE UNIT 269?+
The association fee works out to $1,039 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 269 E CANTON AVENUE UNIT 269?+
The most recent tax bill on record (2025) was $3,470. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 269 E CANTON AVENUE UNIT 269?+
The listing reports pets: No. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Park?+
At $989,500, this home is listed about 58% above the Winter Park median of $627,000. The market section on this page shows how the area is trending.
Which schools are assigned to 269 E CANTON AVENUE UNIT 269?+
Lakemont Elementary (elementary), Maitland Middle (middle), Winter Park High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$989,500 runs 16% above the WINTER PARK 32789 median.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Know the monthly fee
The association fee is $1,039/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Strong assigned schools
Lakemont Elementary, Maitland Middle, Winter Park High — Winter Park High rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of COLDWELL BANKER REALTY · Cathy Sawruk Williams. MLS #O6404706.
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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