442 WOODLAND STREET, Orlando, FL 32806

• 4 beds |
• 4 baths |
• 2,828 sqft

Property Description

Located in Delaney Park, one of downtown Orlando’s most sought-after established neighborhoods, this meticulously restored 1927 residence sits on a generously sized corner lot and blends timeless architectural charm with thoughtful modern luxury. Just minutes from downtown dining, entertainment, and sports destinations, the home combines urban convenience with the warmth and character of a true neighborhood setting. Framed by mature oak trees on a prominent corner lot, the home’s architecture, professionally designed landscaping, and custom entry details create exceptional curb appeal. Unlike many older homes, this property has been extensively upgraded and carefully maintained, preserving its original craftsmanship while modernizing the systems, finishes, and functionality throughout. Original hardwood floors, crown moulding, and architectural details remain beautifully intact, while large windows fill the interior with natural light. The living room features a working gas fireplace, adding warmth and atmosphere to the gathering space. The primary suite renovation completed in 2023 creates a true retreat, featuring elegant wainscoting, dual Restoration Hardware vanities and lighting, and a spa-inspired bath with a massive walk-in shower wrapped in handmade Pratt & Larson ceramic tile. The connected Kohler shower system includes a rain shower, hand spray, body sprays, and built-in speakers, next to a separate private water closet. The kitchen combines custom cabinetry, marble countertops, a gas range, and expansive prep and gathering space designed for both everyday living and entertaining. The adjacent pantry features inset walnut cabinetry and sliding frosted glass doors. The kitchen flows effortlessly into the dining room and charming breakfast nook. A beautifully renovated powder room downstairs includes updated tile flooring, vanity, wainscoting, and designer wallpaper. Upstairs includes three spacious bedrooms, including the primary suite, along with a full hallway bath and a conveniently located second-floor laundry room. Additional living spaces include a vibrant sunroom, creating the perfect flex space for a lounge, reading room, cocktail room, or home office. A detached guest house with a full bath and closet adds flexibility for guests, a private office, gym, studio, or additional living accommodations. The professionally designed backyard creates a private resort-style courtyard retreat centered around the heated pool and spa installed in 2022. A custom block and stucco privacy wall was designed to complement the architecture of the home. The pool and spa can be controlled remotely via app and feature handmade Pratt & Larson ceramic tile with rich tonal variation providing a custom, artisanal feel. Elegant scupper fountains cascade into the spa, while two magnificent Sylvester palms frame the pool area and create the perfect setting for a hammock. Rare in Florida, the property includes both a full basement and a walk-up attic fully insulated with closed-cell spray foam added in 2022, creating exceptional storage space. The home also includes a two-car carport and oversized driveway with ample off-street parking. Major updates include: * New roof, HVAC, and re-pipe in 2016 * Most windows replaced in 2016, with remaining windows replaced in 2021 * Electrical updates completed in 2021 * Exterior and full interior repaint in 2022 * New custom front and rear doors in 2023 * Active termite bond

Listing Status:

Active

Date Added:

May 28, 2026

Data Last Updated:

June 1, 2026 at 3:21AM

Listing Office:

BEYCOME OF FLORIDA LLC : 804-656-5007

Listing Agent:

Steven Koleno : 804-656-5007

MLS ID:

O6411598

Interior

• General: Built-in FeaturesCeiling Fans(s)Crown MoldingEat-in KitchenPrimaryBedroom UpstairsSolid Surface CountersSolid Wood CabinetsStone CountersThermostatWalk-In Closet(s)
• Appliances: DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRefrigeratorTankless Water HeaterTouchless FaucetWasher
• Laundry: Laundry RoomUpper Level
• Basement: Full
• Flooring: TileWood
• A/C: Central AirZoned
• Heating: CentralHeat PumpZoned
• Fireplace: GasLiving RoomFireplace

Exterior

• General: Awning(s)BalconyCourtyardGardenRain GuttersSliding Doors
• Pool: Fiber Optic LightingGuniteHeatedIn GroundPool AlarmSalt WaterTile

Construction

• Roofing: Shingle
• General: StuccoTwoBasement

Location

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

Lot

• Zoning: R-1/TLANCASTER HEIGHTS H/77 LOT 9 BLK J01-23-29-4960-10-090

Utilities

• Utilities: Cable ConnectedElectricity ConnectedFiber OpticsNatural Gas ConnectedSewer ConnectedSprinkler WellWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple