PENDING
$25K PRICE DROP
2880 Old Castle Dr Winter Park, FL 32792
Lake Howell NeighborhoodEstimated payment $6,810/month
Total Views
97,793
5
Beds
4.5
Baths
3,839
Sq Ft
$287
Price per Sq Ft
Highlights
- In Ground Pool
- 0.41 Acre Lot
- Family Room with Fireplace
- Lake Howell High School Rated A-
- Open Floorplan
- Vaulted Ceiling
About This Home
Under contract-accepting backup offers. 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.
Listing Agent
CORCORAN PREMIER REALTY Brokerage Phone: 407-965-1155 License #3012268 Listed on: 05/31/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $8,351
Year Built
- Built in 1993
Lot Details
- 0.41 Acre Lot
- Northeast Facing Home
- Corner Lot
- Irrigation Equipment
- Property is zoned PUD
HOA Fees
- $167 Monthly HOA Fees
Parking
- 3 Car Attached Garage
Home Design
- Slab Foundation
- Shingle Roof
- Stucco
Interior Spaces
- 3,839 Sq Ft Home
- 2-Story Property
- Open Floorplan
- Vaulted Ceiling
- Wood Burning Fireplace
- Blinds
- Sliding Doors
- Family Room with Fireplace
- Family Room Off Kitchen
- Separate Formal Living Room
- Formal Dining Room
- Inside Utility
- Laundry Room
Kitchen
- Eat-In Kitchen
- Range
- Dishwasher
- Stone Countertops
- Solid Wood Cabinet
- Disposal
Flooring
- Wood
- Carpet
- Ceramic Tile
Bedrooms and Bathrooms
- 5 Bedrooms
- Primary Bedroom on Main
- Walk-In Closet
- In-Law or Guest Suite
Pool
- In Ground Pool
- Gunite Pool
- In Ground Spa
Utilities
- Central Heating and Cooling System
- Natural Gas Connected
- Cable TV Available
Community Details
- Michael Leqve Association
- Bear Gully Pointe Subdivision
Listing and Financial Details
- Visit Down Payment Resource Website
- Tax Lot 52
- Assessor Parcel Number 36-21-30-508-0000-0520
Map
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Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2024 | $8,351 | $622,999 | -- | -- |
| 2023 | $8,168 | $604,853 | $0 | $0 |
| 2021 | $7,906 | $570,132 | $0 | $0 |
| 2020 | $7,868 | $562,260 | $0 | $0 |
| 2019 | $7,779 | $549,619 | $0 | $0 |
| 2018 | $7,729 | $539,371 | $0 | $0 |
| 2017 | $7,701 | $528,277 | $0 | $0 |
| 2016 | $6,832 | $525,443 | $0 | $0 |
| 2015 | $6,316 | $447,586 | $0 | $0 |
| 2014 | $6,316 | $444,034 | $0 | $0 |
Source: Public Records
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 08/29/2025 08/29/25 | Pending | -- | -- | -- |
| 08/04/2025 08/04/25 | For Sale | $1,100,000 | 0.0% | $287 / Sq Ft |
| 07/25/2025 07/25/25 | Pending | -- | -- | -- |
| 07/24/2025 07/24/25 | Price Changed | $1,100,000 | -1.8% | $287 / Sq Ft |
| 07/07/2025 07/07/25 | Price Changed | $1,120,000 | -0.4% | $292 / Sq Ft |
| 05/31/2025 05/31/25 | For Sale | $1,125,000 | -- | $293 / Sq Ft |
Source: Stellar MLS
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $638,000 | Attorney | |
| Warranty Deed | $800,000 | First Southwestern Title Com | |
| Warranty Deed | $425,000 | -- | |
| Warranty Deed | $425,000 | -- | |
| Warranty Deed | $379,900 | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $579,860 | New Conventional | |
| Closed | $605,000 | New Conventional | |
| Previous Owner | $96,661 | New Conventional | |
| Previous Owner | $398,118 | New Conventional | |
| Previous Owner | $394,060 | Unknown | |
| Previous Owner | $400,000 | Unknown | |
| Previous Owner | $163,733 | New Conventional | |
| Previous Owner | $275,000 | New Conventional | |
| Previous Owner | $75,000 | Credit Line Revolving |
Source: Public Records
About the Listing Agent
With an impressive past and her eye perpetually toward the future, Jennifer King has made a name for herself in Central Florida real estate as one of the most accomplished, respected, and well-liked real estate agents. Recognized by Orlando Magazine as one of Metro Orlando’s Hot 100 Realtors twice before the age of 30 and holding the title ever since then for fourteen consecutive years, Jennifer has made her mark with her commitment to exceptional service—because achieving true distinction can
Jennifer's Other Listings
Source: Stellar MLS
MLS Number: O6313631
APN: 36-21-30-508-0000-0520
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Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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