Fairbanks Crossing: The Landmark Development Transforming Winter Park in 2025

Winter Park, one of Central Florida’s most established and desirable communities, is entering a pivotal moment of change. Recognized for its historic architecture, lakeside setting, and walkable downtown, this city is now poised to evolve further with the upcoming arrival of Fairbanks Crossing, a new mixed‑use project designed to enhance lifestyle, connectivity, and value.

At ALIGN Real Estate, we believe real estate is about more than just location—it’s about community, design, and forward‑thinking growth. As Winter Park steps into 2025 and beyond, we’re here to guide you through what this means for your next move.

Want a closer look at how Winter Park is evolving in 2025? In this video, we take you inside Fairbanks Crossing, exploring how this landmark mixed-use project is redefining the city’s landscape and enhancing life for residents. From design vision to community impact, see firsthand why this development is set to become one of Winter Park’s most exciting additions.

A Community With Deep Roots and Refined Character

Winter Park’s beginnings trace back to the late 1800s, when it was developed as a resort community along the “Necklace of Lakes” by Lauren A. Chase and Oliver E. Chapman. The city officially became incorporated in 1887 and has retained a unique blend of historical charm and upscale living—from the brick‑lined streets and live‑oak canopies to its elegant downtown core.

Central to the community is Park  Avenue, a pedestrian‑oriented thoroughfare lined with cafés, boutiques, art galleries, and mature trees. Cultural institutions such as the Charles Hosmer Morse Museum (housing the largest collection of Louis Comfort Tiffany art), The Cornell Fine Arts Museum at Rollins College (rotating exhibits), and Rollins College (Florida’s first four‑year college, established in 1885) reinforce the city’s refined identity.

Residential neighborhoods reflect this character, with historic cottage‑style homes, Tudor and Craftsman influences, and walkability that enhances everyday life.

Fairbanks Crossing: A New Chapter in Growth

Fairbanks Crossing is positioned at the northeast corner of Fairbanks Avenue and Denning Drive. Spanning approximately two acres, the project is designed as a mixed‑use retail and dining destination to complement the surrounding neighborhoods and support Winter Park’s evolution.

Key highlights:

• Eleven retail storefronts of around 1,200 square feet each

• Four restaurants of approximately 2,500 square feet, each with outdoor patio space

• A streetscape built with pedestrian experience in mind: wider sidewalks, improved crossings, and thoughtful public realm design

Construction is scheduled to begin in summer 2025 with anticipated completion by 2026. The project is led by Crossmark Services, a Winter Park‑based developer with strong local ties, and fits into the city’s broader corridor plan for Fairbanks Avenue, part of a strategy that includes road widening, streetscape upgrades, and long‑term public space investment.

Enhancing Walkability and Lifestyle

Fairbanks Crossing reflects more than just new retail—it signals an extension of Winter Park’s walkable urban fabric. Situated near Seven Oaks Park and the Minnesota Row mixed‑use redevelopment, the site is one of the next frontiers for lifestyle‑oriented growth in the city.

This initiative aligns with Winter Park’s vision to expand its downtown feel beyond Park  Avenue, creating accessible everyday destinations for dining, shopping, and socializing—all while preserving the town’s historic character.

For residents, the result is clear: increased convenience, enhanced community gathering spaces, and a higher quality of daily living.

Real Estate Context & Buyer Demand

According to Zillow in August 2025, Winter Park’s real estate market remains strong:

• Median home price: approximately $458,370

• Typical time on market: about 35 days

• Cost of living: roughly 35% above the national average, largely driven by housing

While the market reflects premium pricing, the underlying value is supported by location, lifestyle, and community character. The arrival of Fairbanks Crossing strengthens that value proposition by enhancing amenities and local infrastructure.

Who’s Moving to Winter Park?

The appeal of Winter Park is broad and varied:

• Families drawn by top‑rated public and private schools, neighborhood parks, lakeside access, and a walkable town environment

• Professionals seeking proximity to Orlando’s job centers, easy access via SunRail, and a home setting that offers both culture and calm

• Downsizers/empty‑nesters who value walkability, low‑maintenance living, nearby dining and cultural amenities, and preserving lifestyle even as home size changes

Across life stages, the consistent thread is lifestyle—buyers choosing Winter Park often prioritize community intent, school quality, and daily experience over purely transactional factors.

Frequently Asked Questions About Fairbanks Crossing & Winter Park

What is Fairbanks Crossing? 

Fairbanks Crossing is a new mixed‑use development at the corner of Fairbanks Avenue and Denning Drive featuring 11 retail storefronts and four restaurants with outdoor patios. The design prioritizes walkability and will span about two acres.

When is it expected to be completed?

Construction begins in summer 2025, and the project is slated for completion in 2026.

How will it affect the surrounding area?

Fairbanks Crossing is part of a larger corridor upgrade for Fairbanks Avenue, which includes improved roads, wider sidewalks, enhanced pedestrian crossings, and new public space. These upgrades are expected to elevate walkability, local amenities, and community cohesion.

Is Winter Park still a strong market for real estate in 2025?

Yes. With a median list price around $509,000, strong demand, and lifestyle value, Winter Park remains one of Central Florida’s most stable and desirable residential markets. Upcoming developments like Fairbanks Crossing further reinforce potential long‑term value.

What types of buyers will benefit most here?

Buyers who value lifestyle, whether families seeking top schools, professionals seeking city‑access plus quality of life, or downsizers looking for low‑maintenance living and vibrant neighborhoods, will find Winter Park an excellent match.

Who are the top real estate experts in Winter Park?

Navigating Winter Park’s high-demand market requires insight, experience, and local knowledge. ALIGN Real Estate brings a strategic, client-focused approach to every transaction, whether you're buying a historic estate, exploring new developments like Fairbanks Crossing, or selling in a premium neighborhood. With a deep understanding of Winter Park’s unique character and market trends, ALIGN is a trusted partner for buyers and sellers seeking lasting value.

Winter  Park has long been defined by its charm, culture, and walkable neighborhoods. The arrival of Fairbanks Crossing represents an important step forward, extending the town’s distinctive appeal into new territory, enhancing lifestyle options, and reinforcing value.

If you’re considering a move or investment, this moment presents an opportunity. At ALIGN Real Estate, we provide local insight, strategic guidance, and access to a network of listings and resources tailored for the Winter Park market.