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Back 2880 Old Castle Dr
Off Market

2880 Old Castle Dr

Winter Park FL 32792

5
5
3
5133 sq. ft.
17764 sq. ft.
Single-Family
Last sold for $1,010,000
Jennifer KingJennifer King, last sold this property on 30 September 2025 after 121 days on market.

Overview

Welcome to this beautifully designed executive pool home with private in-law quarters, nestled on an oversized corner lot in the gated community of Bear Gully Pointe in Winter Park. Thoughtfully crafted with architectural elegance, this residence features timeless details including plantation shutters, crown molding, and hardwood flooring throughout the first floor. Step inside and be greeted by soaring ceilings, a sweeping circular staircase, and expansive views of the screened lanai and sparkling pool and spa. The bright, open layout includes a spacious first-floor primary suite with a sitting area, spa-like bath, and a custom walk-in closet, as well as a second bedroom conveniently located on the main level. Upstairs you’ll find two additional bedrooms, two full bathrooms, and a versatile loft. Ideal for multi-generational living or guest privacy, the detached in-law suite offers its own living space, full bath, and private access from across the pool. At the heart of the home is a gourmet kitchen equipped with granite countertops, stainless steel appliances, gas cooktop, double ovens, center island, butler’s pantry, oversized walk-in pantry, and a cozy breakfast nook—perfect for entertaining. Additional features include a generous laundry room with washer and dryer, a spacious 3-car side-entry garage with epoxy floors, gas water heater, circular front drive, extended side driveway, and beautifully manicured landscaping. Bear Gully Pointe offers community tennis courts and a playground, all just minutes from Trinity Prep, major highways, UCF, and Orlando International Airport. This is Florida living at its finest.

Features

5 bedrooms
5 bathrooms
3 carspaces
3 garage spaces
5133 sq. ft. floor area
17764 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Winter Park over the last 12 months, the estimated median property value of 2880 Old Castle Dr is $739k.

Median value
$739k
Estimated value range
$430k - $2.5m
Median days on market
35
Estimated value trend
6%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Winter Park. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 2880 Old Castle Dr

2025
Sold
$1,010,000
30 Sep 2025 by Jennifer King, of CORCORAN PREMIER REALTY
2016
Sold
$638,000
13 May 2016 by DIANE STERLING, of KELLER WILLIAMS ADVANTAGE REALTY
2007
Sold
$800,000
15 Mar 2007 by KENNETH HANSON, of KELLY PRICE & COMPANY LLC

Happy sellers in Winter Park

89%
89% of sellers in Winter Park reported that their sale price either exceeded or met their price expectations.

Winter Park stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 17 reviews in Winter Park over the last 12 months.

Local market activity for 5 bedroom single-family properties in Winter Park

In the last 12 months, 24 five-bedroom single-family properties similar to 2880 Old Castle Dr, have been sold.

This represents a 41% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winter Park

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Abby Greenberg

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Jorge Martinez, Jr

Sellers who recommend Jorge Martinez, Jr have praised them for being clear communication, local expert, supportive, friendly, hard-working, well-prepared, and responsive

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Lisa Gould

Sellers who recommend Lisa Gould have praised them for being local expert, clear communication, supportive, responsive, patient, reliable, and empathetic

  •   5   (204 reviews)
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Allison Day

Sellers who recommend Allison Day have praised them for being local expert, responsive, clear communication, supportive, patient, friendly, and empathetic

  •   5   (109 reviews)
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