442 BRIERCLIFF DRIVE, Orlando, FL 32806

• 4 beds |
• 4 baths |
• 2,688 sqft

Property Description

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 Status:

Active

Date Added:

September 18, 2026

Data Last Updated:

September 28, 2026 at 7:21AM

Listing Office:

HOPKEY REALTY : 407-454-1217

Listing Agent:

Michael Dudley : 407-575-8126

Contact:

407-454-1217

MLS ID:

O6441912

Interior

• General: Built-in FeaturesCeiling Fans(s)Dry BarEat-in KitchenHigh CeilingsOtherPrimaryBedroom UpstairsStone CountersVaulted Ceiling(s)
• Rooms: Family Room
• Appliances: DishwasherMicrowaveRangeRefrigerator
• Laundry: InsideLaundry Room
• Flooring: TileWood
• A/C: Central Air
• Heating: CentralElectric
• Fireplace: Living RoomWood BurningFireplace

Exterior

• General: LightingOtherSidewalk
• Other Structures: Guest HouseRear Porch
• Parking: DrivewayElectric Vehicle Charging Station(s)

Construction

• Roofing: Shingle
• General: StuccoFrameTwoCrawlspace

Location

• Road/Access: AsphaltPaved
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1/T/ANBEG 510 FT E OF NW COR OF SE 1/4 OF SW 1/4 RUN S 165 FT E 50 FT N 165 FT W 50 FTTO POB (LESS ST ON N) IN SEC 36-22-2936-22-29-0000-00-062
• View: Trees/Woods
• Fencing: FencedWood

Utilities

• Utilities: Cable AvailableElectricity ConnectedSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple