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Illustrative Winter Park residential street with varied single-family homes, mature shade trees and lush Florida landscaping.

Winter Park, Orange County, Florida

Kenilworth Shores Homes for Sale

See Kenilworth Shores homes for sale. Compare established houses, renovations and yard space to focus your shortlist.

An Established Winter Park Neighborhood

We help you compare Kenilworth Shores homes for sale by layout, condition and improvements in southeastern Winter Park. Established houses from the 1950s through the 1970s sit alongside later construction around streets such as Loch Berry Road, Selkirk Drive and Balmoral Road. We assess the actual home and yard with your renovation or move-in plans in mind.

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 Kenilworth Shores properties by price

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

Recent sales near Kenilworth Shores

45 properties sold within half a mile in the last 12 months · median $630,000

Kenilworth Shores Market Snapshot

View the number of homes for sale and median asking price as a starting point for your property search.

For sale now
7
Median asking price
$1,950,000

Kenilworth Shores Closed Sales: July–September 2026

The mapped Kenilworth Shores search area recorded 10 completed sales from July through September 2026. The median closed price was $667,000, and the median time on market was 8 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.

Explore the Kenilworth Shores Map

See the neighborhood boundary, then compare each home's location with the parks, trails and everyday destinations that matter to you.

Parks, Courts and Golf Around You

These surrounding public facilities can shape your weekly routine. They are not neighborhood-owned amenities or benefits included with your purchase.

  • Cady Way Park

    Tennis, pickleball, softball fields, a playground, picnic tables and a pool offer options for active afternoons. Check facility access arrangements.

  • Lake Baldwin Park

    An off-leash dog area, picnic facilities and a dock suit outdoor downtime. The boat ramp serves boats without gas engines.

  • Winter Park Pines Golf Club

    The city-owned 18-hole course has a driving range, putting green and chipping area for rounds or practice. Membership is not included with a home.

Walking and Cycling Around Winter Park

The Cady Way Trail gives you options for regular walks and bike rides beyond the neighborhood's residential streets. Its connections lead toward the Cross Seminole Trail, Lake Baldwin and Lake Susannah, opening up different routes for a short outing or a longer ride. Around Lake Baldwin, a 2.5-mile loop provides a defined circuit, with connections to Baldwin Park's restaurants and retail for a stop along the way. If walking or cycling is part of your weekly routine, consider the route from each prospective home to a suitable trail access point. Access varies by address, so compare the actual connection rather than assuming every Kenilworth Shores property sits directly beside the trail.

Shopping, Dining and Everyday Facilities

Everyday ownership also means knowing where you will shop, dine and attend appointments. Aloma Corners provides a local convenience-shopping area, while Park Avenue offers a broader shopping destination and Hannibal Square adds dining options to your Winter Park routine. For healthcare context, AdventHealth Winter Park's campus is around North Lakemont Avenue, Mizell Avenue and Edinburgh Drive. These destinations help you assess the location beyond the home itself, whether you are planning regular errands or an evening out. As you compare addresses, consider the routes you would actually use and visit the surrounding area at times that reflect your schedule. That gives you a practical basis for deciding which location best fits your day.

Kenilworth Shores Homes for Sale: Buyer FAQs

Gaby Sadler, Property Specialist

Gaby Sadler

Property Specialist, Serhant

Find Kenilworth Shores homes for sale with Gaby

Tell me your budget and plans for the home. I'll help you compare Kenilworth Shores homes for sale, weigh established houses, renovations and yard space, and identify the details to resolve before you choose.

Find Your Home in Kenilworth Shores

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

Compare Brookshire Heights for established houses near cady way recreation, and Winter Park Pines for established homes with golf, park and trail destinations nearby. Tell Gaby which setting, home features and budget you prefer.