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Illustrative Winter Park streetscape with mature shade trees, lush landscaping and varied detached homes along a quiet residential road.

Winter Park, Florida

The Vias Homes for Sale

Compare layouts, settings and ownership costs to focus your shortlist. Find The Vias homes for sale.

Individual Homes, Not a Uniform Development

The Vias homes for sale offer individual detached and custom homes around Via Tuscany and Lake Maitland's eastern shore in Winter Park. We help you compare architecture, condition, lot setting and any documented waterfront rights, recognizing that this residential area does not follow one uniform development plan.

Top Villas Intelligence

Compare homes with Top Villas Intelligence

Review available property reports, ownership costs and nearby-sale comparisons. Report availability varies by home.

Sample: $118,400 gross rental revenue at 74% projected occupancy, $61,900 operating income and a 7.2% operating yield, with high confidence.

Browse The Vias properties by price

Search price ranges within this area while keeping the property criteria for this page.

Recent sales near The Vias

29 properties sold within half a mile in the last 12 months · median $750,000

The Vias Market at a Glance

Compare public for-sale inventory and median asking price as a starting point for your property search.

For sale now
10
Median asking price
$1,662,450

The Vias Closed Sales: July–September 2026

The mapped The Vias search area recorded 5 completed sales from July through September 2026. The median closed price was $2,025,000, and the median time on market was 160 days. These are completed-sale measures, separate from the live asking prices above. Different home sizes, conditions and locations can materially change an individual property's value.

Source: Top Villas Realty area sales snapshots, three months ending September 2026; retrieved 29 October 2026. All property types within this page's mapped search area are included.

Map of The Vias in Winter Park, FL

Explore the neighborhood boundary, then consider each home's location in relation to your everyday Winter Park routine.

Public Parks for Everyday Enjoyment

These public spaces offer different ways to enjoy time outdoors. Consider the route from each home, rather than assuming every park is within walking distance.

  • Kraft Azalea Garden

    Enjoy lakeside walks in this 5.22-acre public garden on Lake Maitland, with mature cypress trees, paths, benches and the Exedra.

  • Howell Branch Preserve

    North of Howell Branch Road and west of Temple Drive, this 10.38-acre preserve offers a natural setting surrounded by wetlands and habitat.

  • Phelps Park

    Playground equipment, basketball courts, tennis courts and pavilions give you options for active afternoons and outdoor time with friends.

  • Central Park

    Eleven acres on Park Avenue and events throughout the year make this public park a place to revisit as part of your downtown routine.

Winter Park Racquet Club: A Separate Membership

Winter Park Racquet Club sits at 2111 Via Tuscany on Lake Maitland's eastern shore. Its eight clay Hydro-Courts, pickleball and junior Olympic swimming pool make it relevant if racquet sports or swimming feature in your preferred routine. Lake activities, dining and social programming add other ways to enjoy the setting. This is a separate membership amenity, however, not a facility included with ownership of a nearby home. Prospective members require an invitation, sponsorship by an existing member and satisfaction of the club's requirements. If the club is an important part of your plans, explore its membership process separately from your property search so you can distinguish the home's features from activities that depend on joining.

Lake Recreation and Waterfront Ownership

Living near Lake Maitland and owning waterfront property are different choices. Frontage, a private dock and deeded lake access are features to assess for each home, not benefits that accompany every address in The Vias. Start by deciding whether you want the water to be part of your property or simply part of your wider recreation options. The Winter Park Chain of Lakes provides opportunities for boating, skiing and fishing, with public launching at Dinky Dock Park. Before launching a motorboat on the chain, you need a city boat sticker or day pass. Keeping public recreation separate from property-specific access helps you compare homes according to how you actually expect to spend time on the water.

Broad daylight lake view with gently rippling water and a lush, tree-lined shoreline, evoking Lake Maitland in Winter Park.

A Home Base for Enjoying Winter Park

Owning in The Vias gives you a residential base from which to enjoy the broader Winter Park setting. Park Avenue brings together shopping, dining and cultural interests, offering reasons to spend time downtown beyond an occasional special outing. Think about how those surroundings would fit into an ordinary week: meeting friends for a meal, browsing shops or making time for an event in Central Park. For a second home, consider the routines you would want to return to, not just the places you might visit once. When viewing a property, leave time to explore the surrounding streets and your likely routes to the places you expect to use regularly.

Also Considering Isle of Sicily, FL?

If Isle of Sicily, FL is also on your shortlist, keep your comparison focused on the individual homes. Review layout, outdoor space and the location of each property alongside the homes you are considering in The Vias. Do not assume waterfront frontage, a private dock or deeded lake access from an area name alone. We can help you identify which property details need confirming before you arrange viewings.

Explore Isle of Sicily homes for sale

The Vias Homes for Sale: Buyer FAQs

Gaby Sadler, Property Specialist

Gaby Sadler

Property Specialist, Serhant

Find The Vias homes for sale with Gaby

Tell me your budget and plans for the home. I'll help you compare The Vias homes for sale, weigh layouts, settings and ownership costs, and identify the details to resolve before you choose.

Find Your Home in The Vias

Explore Winter Park homes for sale for a wider view, or use the neighborhood comparison to narrow your shortlist.

Compare Via Tuscany for a street-focused search within the wider vias area, and Park Grove for north park avenue setting and varied single-family homes. Tell Gaby which setting, home features and budget you prefer.