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© 2026 DockOnly™. All rights reserved.

DockOnly™ and Dock Score™ are trademarks of Blue Mar Real Estate Group Inc.

Blue Mar Real Estate Group Inc. — Licensed Florida Real Estate Broker

Blue Mar Real Estate Group Inc.

Licensed Florida Real Estate Broker · DBPR License CQ1018554

4000 Ponce De Leon Blvd, Suite 470, Coral Gables, FL 33146

[email protected]

Listing data is provided by participating Multiple Listing Services and is deemed reliable but not guaranteed. Each listing's MLS source and its required disclosures appear with that listing. Dock Score™ is a DockOnly.com rating and is not provided by or affiliated with any MLS or listing broker. NOAA chart data is public domain and for reference only — not for navigation. Full MLS Compliance

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+20

4469 OLD BEAR RUN

WINTER PARK, FL, 32792

Active Under Contract

$1,799,999

4469 OLD BEAR RUN

WINTER PARK, FL, 32792

Active Under Contract

$1,799,999

5

Bedrooms

5

Bathrooms

4,288 sqft

Living Area

1978

Year Built

$1,799,999Tour the dockSchedule a Showing
Navigation note: Navigation routes show the shortest mapped path to open water. A vessel taller than the binding bridge clearance may still reach open water via a longer alternate route that we don't currently map — verify navigability with a local captain or surveyor before relying on it.

32,200

Lot Size (sqft)

155

Days on Market

Dock Score™

DockOnly
27
Limited

What shaped this score

✓Dock with boat lift
✓Fits boats up to ~46ft (est.)
✓deep water
·Lake/Lagoon

DockOnly.com rating — not provided by the MLS or listing broker.

Dock & Water AccessMLS

Lake Front

AI Aerial Imagery Detection

Dock DetectedBoat Lift DetectedDeep Water Indicators~39-53 ft dock

Detected by AI from open-source aerial mapping imagery and may not reflect current conditions. This information was not provided by the MLS or listing broker. Always verify dock infrastructure with the listing agent.

Navigation RouteDockOnly

Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.

Description

Under contract-accepting backup offers. Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.

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Location

WINTER PARK, FL, 32792

No price history available for this property.

Displayed by Blue Mar Real Estate Group Inc. — Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]

Listing courtesy of LPT REALTY, LLC via Stellar MLS

Last updated: 7/14/2026

© 2026 Stellar MLS. All rights reserved. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) program of Stellar MLS. Information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal.

IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Dock Score™

DockOnly
27
Limited

What shaped this score

✓Dock with boat lift
✓Fits boats up to ~46ft (est.)
✓deep water
·Lake/Lagoon

DockOnly.com rating — not provided by the MLS or listing broker.

FEMA Flood Zone X
BFE: -9999ft

Minimal Flood Hazard

View FEMA Flood Map →
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Mortgage Calculator

Estimate your monthly payment for this waterfront property

20%

$360,000 down

%
Principal & Interest$9,340/mo
Property Tax (est. ~1.2%, varies by county)$1,800/mo
Home Insurance (est.)$250/mo
Total Monthly Payment$11,390
Loan Amount: $1,439,999Rate: 6.75%
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Estimated payments only. Actual rates and terms may vary.

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