Home in 442 Woodland St Orlando for sale with MLS# O6411598

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

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Days on the market

442 Woodland St, Orlando, FL 32806

Price
Price:
$1,279,000.00
Original List Price:
$1,279,000.00
List Price per Sq Ft (Calculated, Approx.):
$452.26
Property Status and Type
Listing Type:
For Sale
Status:
Active
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
O6411598
Rooms Distribution
Bedrooms:
4
Bathrooms Total:
4
Full Bath:
3
Half Bath:
1
Measures
Living Area:
2,828 Sqft
Built-Up Area:
4,260 Sqft
Lot Area:
7,722 Sqft
Building Area Source:
Owner
Living Area Source:
Owner
Lot Size Acres:
0.18
Property Features
Waterfront:
No
Private Pool
Swimming Pool Features:
Gunite, Heated, In Ground, Salt Water, Tile, Fiber Optic Lighting, Pool Alarm
Furnished:
Unfurnished
Appliances:
Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Gas Water Heater, Range, Tankless Water Heater, Touchless Faucet
Interior:
Eat-in Kitchen, Walk-In Closet(s), Built-in Features, Ceiling Fans(s), Stone Counters, Thermostat, Solid Surface Counters, Solid Wood Cabinets, Crown Molding, Primarybedroom Upstairs
Exterior:
Awning(s), Balcony, Courtyard, Sliding Doors, Rain Gutters, Garden
Laundry:
Laundry Room, Upper Level
Fireplace
Fireplace:
Gas, Living Room
Air Conditioning System:
Zoned, Central Air
Heating System:
Central, Zoned, Heat Pump
Basement:
Full
Property Entrance Faces:
North
Other Equipment:
Irrigation Equipment
Construction
Year Built:
1927
Roof:
Shingle
Levels:
Two
Construction Materials:
Stucco
Flooring:
Tile, Wood
Foundation Details:
Basement
Flood Zone Code:
X
Taxes and Expenses
Tax Annual Amount:
$12,517.00
Tax Year:
2025
Parking
Carport Spaces:
2
Carport
Utilities
Sewer:
Public Sewer
Utilities Available:
Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected, Cable Connected, Sprinkler Well, Fiber Optics
Water Source:
Public
Community
Minimum Lease Term:
1 Month
Subdivision Name:
LANCASTER HEIGHTS
Senior Community:
No
Terms
Listing Terms Considered by Seller:
Cash, Conventional, FHA, VA Loan, Other
Occupant Type:
Owner
Lease Considered:
Yes
Zoning and Legal
Tax Legal Description:
LANCASTER HEIGHTS H/77 LOT 9 BLK J
Real Estate Folio Number (Parcel Number):
01-23-29-4960-10-090
Zoning:
R-1/T
Title to the property is held by owner as:
Fee Simple
Listing History
Originally published on:
May 28, 2026 4:43 pm
Active on the market since:
May 28, 2026
Listing Agreement executed on:
May 28, 2026
Listing Status Last Changed On:
May 28, 2026 4:43 pm
Photos updated on:
May 28, 2026 8:57 pm
Last Modified:
May 31, 2026 3:02 pm
Additional Information
Courtesy of:
BEYCOME OF FLORIDA LLC
Attribution:
844-239-2663
Road Surface Type:
Paved
Location
Street Name:
WOODLAND
Street Number:
442
City:
ORLANDO
State:
Florida
Zip Code:
32806
County:
Orange
Latitude:
N28° 31' 20.2''
Longitude:
W82° 37' 46.2''
Property Map

Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $86,653
Median Home Value $415,800
Median Rent $1,500/mo
Median Age 40
Population 26,423

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Association of REALTORS®
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