442 BRIERCLIFF DRIVE, Orlando, FL 32806

• 4 beds |
• 4 baths |
• 2,688 sqft

Property Description

Timeless charm meets refined living in this beautifully updated historic home in the heart of Delaney Park, complete with a detached guest house and thoughtfully designed living spaces. Offering 4 bedrooms, 4 bathrooms, and 2,688 square feet, this residence blends classic character with modern comfort in one of downtown Orlando’s most desirable neighborhoods. Inside, a welcoming living room with a built-in wood-burning fireplace creates a warm focal point and flows seamlessly into the separate dining room, both highlighted by wood flooring. Just beyond, the kitchen is designed for both everyday living and entertaining, featuring custom cabinetry, stone countertops, stainless steel appliances, a spacious island, dry bar, and generous cabinet and counter space. The kitchen overlooks a stunning family room with vaulted ceilings and an abundance of large windows and doors that fill the space with natural light while offering views of the backyard. The main level includes two bedrooms and two full bathrooms, providing flexibility for a variety of living arrangements. Upstairs, the private primary suite serves as a peaceful retreat with large built-in closets and a beautifully renovated en suite bathroom featuring dual sinks, a spacious glass walk-in shower with a built-in bench, and a separate soaking tub. The detached guest house includes a full bathroom, air conditioning, and a convenient kitchenette, providing a perfect space for guests, work, or hobbies. The fenced backyard with a large stone porch is ideal for entertaining or quiet evenings outdoors. Perfectly situated in the heart of downtown Orlando, this home offers effortless access to dining, shopping, and major roadways, with world-famous theme parks and Orlando International Airport just a short drive away—combining timeless elegance with modern city living. Mortgage savings may be available for buyers of this listing.

Listing Status:

Active

Date Added:

March 19, 2026

Data Last Updated:

March 27, 2026 at 8:22PM

Listing Office:

REDFIN CORPORATION : 407-708-9747

Listing Agent:

Wylie Devlin : 407-463-1014

MLS ID:

O6390631

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
• Fencing: FencedWood

Utilities

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

Financial

• Source: Stellar MLS
• Ownership: Fee Simple