# 4469 OLD BEAR RUN, Winter Park, FL 32792

> **TL;DR:** 5bd/5ba single family, $1,799,999 ($420/sqft), built 1978, 4,288 sqft.
> Pool, Waterfront. Est. $7,800/mo. Listed 147 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $1,799,999 |
| Price/sqft | $420 |
| Bedrooms | 5 |
| Bathrooms | 4 full, 1 half |
| Square Feet | 4,288 |
| Year Built | 1978 |
| Lot Size | 32,234 sqft (0.74 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 147 |

## Why This Home Stands Out

- **Pool** - Private pool
- **Waterfront** - Direct water access

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $7,800 |
| **Total** | **$7,800** |

## Nearby Schools

- **Elementary:** Red Bug Elementary
- **Middle:** Tuskawilla Middle
- **High:** Lake Howell High

## Key Amenities

- Pool
- Waterfront

## Property Highlights

- Built in 1978
- 0.74 acre lot
- Private pool
- Waterfront

## Description

### Agent Description
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.

## Location

- **Address:** 4469 OLD BEAR RUN, Winter Park, FL 32792
- **County:** Seminole
- **Neighborhood:** PERVIS SURVEY FOR R E
- **Coordinates:** 28.623765, -81.267965
- **Google Maps:** https://www.google.com/maps?q=28.623765,-81.267965

## Listing Agent

- **Name:** Keigan Lewis
- **Brokerage:** LPT REALTY, LLC
- **Phone:** 3053938683
- **Email:** Keiganlewis@legacyestatesfl.com

## Primary Photo

![4469 OLD BEAR RUN - Primary Photo](http://lh.rdcpix.com/4be07a92248d9705a1223958694ab40cl-f1104497491r.jpg)

*77 total photos available on [listing page](https://www.propertysimple.com/listing/4469-old-bear-run-winter-park-fl-32792-o6375415)*

---

**MLS#:** O6375415 | **Updated:** 2026-06-17
**Source:** listhub

*Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.com/listing/4469-old-bear-run-winter-park-fl-32792-o6375415)

---

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