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2873 OLD CASTLE DRIVE, WINTER PARK, FL - photo 1

$1,395,000

2873 OLD CASTLE DRIVE

WINTER PARK, FL 32792

Estimated payment $8,129/month

includes HOA $500/mo · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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4Beds
4Baths
4,247Sq Ft
$328Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

HOA $500/mo
Private Pool
Fireplace
Garage
Built in 1993
25,595 sqft Lot

About This Home

Under contract-accepting backup offers. Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gated community of Bear Gully Pointe in Winter Park. Nestled along the shores of Bear Lake, a 137- acre spring-fed lake, this stunning estate-like property sits on more than half an acre and is surrounded by lush landscaping, mature trees and beautifully maintained grounds. From the moment you arrive, the long, newly paved driveway sets the tone for what awaits. Meticulously maintained, this impressive home offers 4 bedrooms, 4 full bathrooms, a dedicated office and a spacious upstairs loft/bonus room. The dramatic entry features soaring ceilings, expansive windows and sliding glass doors that draw your attention to the pool and picturesque backyard. The formal dining room, accented by coffered ceilings, flows seamlessly into the beautifully appointed kitchen through a wet bar and wine closet. Completely reimagined down to the studs in 2016, the kitchen features gorgeous marble countertops, custom cabinetry with built-in drawers, a brand-new gas cooktop, double wall ovens, Sub-Zero refrigerator, generous breakfast nook and a large picture window overlooking the pool. The kitchen opens directly to the spacious family room, where soaring ceilings, floor- to-ceiling windows, a gas fireplace and custom built-in cabinetry create an inviting gathering space. A secondary bedroom and full bathroom are conveniently located just off the family room. The expansive downstairs primary suite is a true retreat, featuring tall ceilings, abundant windows and a French door providing direct access to the pool and lanai. Completely remodeled in 2019, the luxurious primary bath offers two separate vanities with dual sinks, a spacious shower with dual shower heads, a beautiful soaking tub and a custom walk-in closet. Just beyond the primary suite is a dedicated office and convenient pool bath. Upstairs, a separate living area provides exceptional flexibility with a generous loft/bonus room, two spacious bedrooms and a full bath featuring dual sinks, a soaking tub and separate shower. Designed with entertaining in mind, the home’s indoor and outdoor spaces blend effortlessly together. The heated pool and spa are surrounded by a covered, screened lanai and a lush backyard oasis complete with mature trees and charming walking paths—creating a private setting for relaxing or entertaining. Bear Gully Pointe offers sidewalks throughout the community, a tennis court, playground and a brand-new gazebo overlooking Bear Lake. Ideally located just minutes from downtown Winter Park, Trinity Preparatory School, Winter Springs and Oviedo. Additional updates include a 2021 roof, 2022 gas water heater, 2024 re-pipe, 2016 pool resurfacing, 2025 driveway, 2022 exterior paint and hardwood flooring downstairs added in 2013.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:4
  • •Bathrooms:4
  • •Full bathrooms:4
  • •Half bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:4,247 sqft
  • •Total interior livable area:4,247 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:25,595 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1993

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Price history

DateEventPrice
2026-09-08T00:00:00.000ZListed for sale$1,395,000$328/sqft

Listing Agent

Wendy Williams Crumit

FANNIE HILLMAN & ASSOCIATES

Brokerage Phone: 407-644-1234

Source: Stellar MLS · MLS #O6438691

Data Powered by Home Junction, Inc.

Nearby

Schools

EASTBROOK ELEMENTARY SCHOOL

Elementary · 1.1 mi

TUSKAWILLA MIDDLE SCHOOL

High · 1.1 mi

LAKE HOWELL HIGH SCHOOL

High · 1.2 mi

Supermarkets

Susan Clemons

0.5 mi

Publix

0.8 mi

Walmart Supercenter

0.9 mi

Dining

Wendy's

0.5 mi

Sweet Dream Cakery

0.6 mi

7-Eleven

0.6 mi

Parks

Anson Park

0.5 mi

Calabash Place Park

0.6 mi

Atwater Park

0.8 mi

Beaches

Lake Baldwin Park Beach

4.4 mi

Conrad Beach

21.2 mi

East Beach

21.3 mi

Nearby amenity locations include data © OpenStreetMap contributors.