$1,279,000
Off-Market Date: 06/03/2026442 Woodland Street Orlando, FL 32806
Pending MLS# O6411598
4 beds 4 baths 2,828 sq ft Single Family
Details for 442 Woodland Street
MLS# O6411598
Description for 442 Woodland Street, Orlando, FL, 32806
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 Information
Property Type: Residential, Single Family Residence
Status: Pending
Bedrooms: 4
Bathrooms: 4
Lot Size: 0.18 Acres
Square Feet: 2,828 sq ft
Year Built: 1927
Stories: 2 Story
Construction: Stucco
Subdivision: Lancaster Heights
Foundation: Basement
County: Orange
Room Information
Main Floor
Dining Room:
Living Room:
Kitchen:
Upper Floor
Bedroom 3:
Bedroom 2:
Bedroom 1:
Primary Bedroom:
Lower Floor
Basement:
Basement:
Bathrooms
Full Baths: 3
1/2 Baths: 1
Additonal Room Information
Laundry: Laundry Room, Upper Level
Interior Features
Appliances: Tankless Water Heater, Gas Water Heater, Washer, Microwave, Range, Refrigerator, Dishwasher, Disposal, Dryer
Flooring: Tile,Wood
Basement: Full
Fireplaces: Gas, Living Room
Additional Interior Features: Ceiling Fan(s), Eat-In Kitchen, Walk-In Closet(s), Built-in Features, Wood Cabinets, Upper Level Primary, Solid Surface Counters, Stone Counters, Crown Molding
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Connected,Electricity Connected,Fiber Optic Available,Natural Gas Connected,Sewer Connected,Water Connected
Cooling: Zoned, Central Air, Ceiling Fan(s)
Heating: Central, Heat Pump, Zoned
Exterior / Lot Features
Roof: Shingle
Pool: Heated, Tile, In Ground, Salt Water, Gunite, Pool Alarm
Additional Exterior/Lot Features: Garden, Courtyard, Awning(s), Rain Gutters, Sprinkler/Irrigation, Balcony, Balcony
Driving Directions
From South Orange Ave: Turn onto Kaley Street, go straight through the traffic light at the intersection of Kaley and Delaney Ave, then take your next left onto Osceola Ave. Continue straight through the stop sign at Avalon Blvd, then the house is on the left hand side on the corner of Osceola Ave and Woodland St.
Financial Considerations
Terms: Cash,Conventional,FHA,Other,VA Loan
Tax/Property ID: 01-23-29-4960-10-090
Tax Amount: 12517
Tax Year: 2025
A broker reciprocity listing courtesy: BEYCOME OF FLORIDA LLC
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Copyright 2026 Stellar MLS as distributed by the MLS GRID. All Rights Reserved.
Sales History & Tax Summary for 442 Woodland Street
Sales History
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Tax Summary
| Tax Year | Estimated Market Value | Total Tax |
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 442 Woodland Street
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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