Castellano
Castellano Building Company Custom homes, Orlando Established 1979 214 houses finished
ProjectCastellano Building Co
DrawingWinter Park
Typical lot0.25 to 0.40 acre
IssuedFebruary 2026
Sheet08 of 21

In Winter Park you are building around trees that were here before the street.

Two reviews happen before a building official reads a single sheet, the canopy has legal standing, and the lot you are buying almost certainly has a house standing on it already.

The lot

A teardown, and the trees are the survey.

Nearly everything available here is a quarter to four tenths of an acre with a 1950s or 1960s house on it. Asking prices ran $650,000 to $1,900,000 through last year, and what separates the two ends is the block, the width and how many protected trees sit in the middle of where a house wants to go.

Demolition runs $18,000 to $34,000, an asbestos survey is required on anything built before 1981, and the existing water and sewer taps can usually be reused, which quietly saves eight to twelve thousand dollars. Get the tree survey before the inspection period ends, not after. On this side of town it is the document that decides the floor plan.

The eight lot checks, sheet 06

What is different about building here
  • The canopy has standingA live oak over a certain trunk diameter is not coming down for your convenience. Removal needs a permit, a reason and mitigation in replacement inches, and the root protection zone gets fenced and inspected. On Via Tuscany the house was drawn as an L around two ninety year old oaks and the driveway was routed to miss the roots.
  • Two reviews before the cityTree review and design review both run ahead of building review, which is why Winter Park permits take 12 to 16 weeks rather than the 8 that Lake Nona can manage. Nothing about this is negotiable and everything about it is predictable, so it belongs in the schedule from day one.
  • Size is capped by the lot, not the budgetFloor area ratio, height and setbacks together decide the largest house that can stand there, and on a narrow lot the limit usually arrives before the money does. We draw the envelope to scale before anybody sketches a plan.
  • The street is finished and watchingBrick roads, no laydown space, and neighbors who have lived there thirty years. Deliveries get staged offsite, the dumpster sits where we agreed with the house next door, and the crew parks where we said it would.
  • The context is realA 6,000 square foot house dropped between two 1950s cottages is why design review exists. The good outcome here is a house that looks like it has been on the street for a while, which is a drawing problem rather than a budget problem.
The house we built here
The Via Tuscany house from the street after rain, standing seam metal roof, board and batten walls and two live oaks over the driveway
Via Tuscany house. Completed March 2024Both oaks kept, and the driveway routed around the root zone of the larger one.

The Via Tuscany house

The two oaks sat exactly where a rectangular house wanted to go. The alternative to drawing an L was removing a tree that was standing before the street had a name, so the house bent instead. The screened porch across the back sits under the larger of the two.

The Via Tuscany house, sheet 16

Area4,180 sq ft
Lot0.34 acre, teardown
ArchitectHalsey Ward
Permit to keys14 months
What a house here runs

Winter Park is the second most expensive place we build.

Not because of the finishes. Because of the site: a demolition, a tree protection plan, a longer permit and a street with nowhere to put anything.

Typical size here3,800 to 5,200 sq ft
Construction, per square foot$395 to $525
The house itself$1,500,000 to $2,730,000
Demolition and site work$46,000 to $94,000
Permits, impact fees, tree mitigation$22,000 to $44,000
Before the lot, design or pool$1,568,000 to $2,868,000

The full arithmetic, sheet 03

Questions

Three questions about Winter Park.

Can I take a tree down if it is where the house needs to go?

Sometimes, and it is not a conversation you win by wanting it. The city looks at species, trunk diameter, condition and whether a reasonable alternative exists, and a healthy specimen oak in good condition is generally staying. Mitigation is paid in replacement inches, which on a large tree can run past $12,000. Our usual advice is cheaper and better: draw the house around it. On Via Tuscany that decision produced the best room in the house.

Why does a Winter Park permit take longer than one in Lake Nona?

Because three separate reviews run in sequence rather than at the same time. Tree review comes first, design review second, and only then does a plans examiner open the structural set. Budget 12 to 16 weeks and treat anything faster as a gift. Sheet 04 breaks the whole schedule down and shows where the weeks actually go.

We already own a house here and want to rebuild on the same lot. Is that different?

It is simpler in one way and harder in another. You already know the utilities, the drainage and the neighbors, which removes most of the unknowns. What you gain in certainty you spend on living somewhere else for fourteen to eighteen months, and that rent belongs in the budget from the first conversation rather than the eighth.

Closing

Two hundred and fourteen plates.
We know where all of them are.

Four to six houses a year, on purpose. Tell us where the lot is, or tell us you are still looking, and we will say honestly whether we are the right company for it. If we are not, we will tell you who is.

Read by Miguel Castellano, usually the same day