A rare opportunity to own a beautifully renovated historic home with a detached guest house in the heart of Delaney Park. Set on a charming residential street surrounded by some of Downtown Orlando’s most sought-after neighborhoods, this 4-bedroom, 4-bath residence offers 2,688 square feet of thoughtfully designed living space with a seamless blend of original character and modern updates.
From the moment you enter, the home feels warm and inviting, with beautiful wood floors, a spacious living room with a wood-burning fireplace, and a separate dining area ideal for entertaining. The updated kitchen serves as the centerpiece of the home, featuring custom cabinetry, stone countertops, stainless steel appliances, a large center island, dry bar, and abundant storage.
The kitchen opens directly to an impressive vaulted family room surrounded by oversized windows and glass doors, creating a bright and airy gathering space with views of the private backyard. The first floor also offers two bedrooms and two full bathrooms, providing excellent flexibility for guests, family, or a home office.
Upstairs, the primary suite offers a private retreat with generous built-in closet space and a beautifully updated bathroom featuring dual vanities, a large glass-enclosed walk-in shower with built-in bench, and a separate soaking tub. An additional bedroom and full bathroom complete the upper level.
Adding exceptional versatility, the detached guest house includes its own full bathroom, air conditioning, and kitchenette. Whether used for guests, extended family, a private office, creative space, or an additional living area, this separate structure adds a level of flexibility rarely found in the neighborhood.
Outside, the fenced backyard and expansive stone porch create an inviting setting for outdoor dining, entertaining, or relaxing in privacy. The location is equally impressive, placing you minutes from Lake Davis, Lake Cherokee, Delaney Park, Thornton Park, Downtown Orlando, restaurants, coffee shops, shopping, and major roadways, while Orlando International Airport and Central Florida’s world-famous attractions are easily accessible.
A distinctive home, an exceptional location, and the flexibility of a detached guest house make 442 Briercliff Drive a truly special Delaney Park offering.
Listing updated: 2026-10-31T17:04:32.337Z
Listed by Realtor: Michael Dudley
Listed by office: HOPKEY REALTY
Source: Stellar MLS
Property Details
Listing Id: O6441912
Price: $849,000
Property Size:2,688 ft2
Property Lot Size:0 ft2
Rooms: 5
Bedrooms: 4
Bathrooms: 4
Bathrooms Full: 4
Modification Timestamp: 2026-10-31T17:11:21.312Z
Building Area Total: 2868
Construction Materials: Stucco, Wood Frame
Cooling: Central Air
CumulativeDaysOnMarket: 218
DaysOnMarket: 43
DirectionFaces: North
ElementarySchool: Blankner Elem
Fencing: Fenced, Wood
FireplaceFeatures: Living Room, Wood Burning
Flooring: Tile, Hardwood
FoundationDetails: Crawlspace
Furnished: Unfurnished
HighSchool: Boone High
Laundry Features: Inside, Laundry Room
Levels: Two
List AOR: Orlando Regional
List Agent AOR: Orlando Regional
List Agent Email: mike@dudleyeliterealty.com
List Agent Full Name: Michael Dudley
List Agent MlsId: 261208174
ListOfficeMlsId: 261017758
List Office Name: HOPKEY REALTY
ListOfficePhone: 407-454-1217
Listing Terms: Cash, Conventional, FHA, VA Loan
Living Area Source: Public Records
Lot Features: Landscaped, Level, Sidewalk
LotSizeArea: 7267
LotSizeSquareFeet: 7267
MLS Area Major: 32806 - Orlando/Delaney Park/Crystal Lake
MiddleOrJuniorSchool: Blankner School (K-8)
MlsStatus: Active
ModificationTimestamp: 2026-10-31T17:04:32.337Z
OnMarketDate: 2026-09-18
Originating System Name: Stellar MLS
Other Structures: Guest House
Ownership: Fee Simple
Parcel Number: 362229000000062
Parking Features: Driveway, Electric Vehicle Charging Station(s)
Pets Allowed: Yes
Roof: Shingle
Sewer: Public Sewer
State Or Province: FL
Status Change Timestamp: 2026-09-19T01:46:09.793Z
Street Name: BRIERCLIFF
Street Number: 442
Street Number Numeric: 442
Street Suffix: DRIVE
Tax Annual Amount: 13489
Tax Block: 00
Tax Book Number: 00
Tax Year: 2025
Utilities: Cable Available, Electricity Connected, Sewer Connected, Water Connected
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