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Rare Builders

Orlando Neighborhoods

Custom Homes in Winter Park

Rare Builders has completed custom and spec residences throughout Winter Park, from established infill streets to lake-oriented properties. That body of work has given us a practical understanding of the city’s varied lots, mature landscapes and architectural character.

Each home begins with its setting. Neighboring residences, trees, privacy, drainage, natural light and outdoor space all influence the plan. The result should feel individual while remaining considered in relation to the street and neighborhood around it.

Front elevation of Dana: a two-storey white stucco home with a dark tile roof, arched entry with a black glass door, a tall arched window and two dark garage doors beside a herringbone paver driveway.

A Home That Belongs Here

Winter Park is not one condition. Its streets include compact infill properties, broad lots and homes oriented toward the water. Planning begins with what is already present: the approach from the street, established tree canopy, neighboring windows, grade and the places where privacy matters most.

Architectural direction can vary from one residence to the next. The consistent work is proportion, siting and the relationship between interior rooms and the landscape around them.

Designed Around Daily Life

The plan is developed around how the rooms connect and how they are used throughout the day. Kitchens, living spaces and conditioned or covered outdoor rooms are considered together, with natural light, circulation and views shaping their arrangement.

Pools, spas, terraces and landscape are coordinated as part of the residence rather than treated as separate additions after the primary plan is resolved.

Built in Winter Park

The residences below show a range of responses within Winter Park: Dana’s arched openings and connected living spaces, Killarney’s lake-oriented rear elevation, Rockwood’s shaded outdoor rooms, Spring’s courtyard plan and Oakwood’s pool-centered composition.

Recognition for Dana

Dana received First Place — Single Family – Owned, 2026 Parade of Homes Orlando.

From Site to Completion

Work begins with the property and the intended program, then moves through design coordination, scope and pricing, planning, construction and completion. Decisions are made in sequence so the architecture, systems, interiors and outdoor spaces can be considered as one project.

Additional Winter Park work

This verified address record includes completed Rare Builders work. A listed address does not imply that a public case study is available.

  • 100 E Rockwood Way
  • 451 W Comstock
  • 1331 Lakeview Drive
  • 2607 Parkland

Begin with the property

Whether you are planning a residence or considering the future of a property, the first step is a direct conversation about the site.