442 WOODLAND STREET Orlando, FL $ 1,279,000
442 WOODLAND STREET
$ 1,279,000
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442 WOODLAND STREET

Orlando, FL, 32806
$ 1,279,000
Bedrooms4 Baths2.1 Sq 2,828

Monthly Estimate*

$ 7,875

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Single Family Home for sale in Orlando, FL

for $1,279,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,828 square foot home was built in 1927 on a lot size of 0.18.

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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Single Family Active

Price

$ 1,279,000

Bedrooms

4

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 12,517

Style

Single Family Residence

Lot Size

0.18

Year Built

1927

Town/City

Orlando

County/Region

Orange

MLS | Web ID

O6411598

Features
General
Sewer Public Sewer
Heating Central Heat Pump Zoned
Cooling Central Air Zoned
Utilities Cable Connected Electricity Connected Fiber Optics Natural Gas Connected Sewer Connected Sprinkler Well Water Connected
Roof Shingle
Appliances Dishwasher Disposal Dryer Gas Water Heater Microwave Range Refrigerator Tankless Water Heater Touchless Faucet Washer
Zoning R-1/T
Pool Features Fiber Optic Lighting Gunite Heated In Ground Pool Alarm Salt Water Tile
Construction Materials Stucco
Year Built 1927
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Subdivision Name LANCASTER HEIGHTS
Facing Direction North
Garage Y/N false
Total Rooms 9
Full Baths 2
Status Active
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.
City ORLANDO
Senior Community Y/N false
MLS Area 32806 - Orlando/Delaney Park/Crystal Lake
Lot Size Units Square Feet
Lot Size Square Feet 7722
Carport Spaces 2
Carport Y/N true
Listing Terms Cash Conventional FHA Other VA Loan
Land Lease Y/N false
Tax Annual Amount 12517
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6411598
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 9
Legal Description LANCASTER HEIGHTS H/77 LOT 9 BLK J
Minimum Lease 1 Month
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Built-in Features Ceiling Fan(s) Crown Molding Eating Space In Kitchen PrimaryBedroom Upstairs Solid Surface Counters Solid Wood Cabinets Stone Counters Thermostat Walk-In Closet(s)
Basement Full
Flooring Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Gas Living Room
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Laundry Room Upper Level
Total Bedrooms 4
Total Baths 3
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Exterior
Exterior Amenities Awning(s) Balcony Courtyard Garden Irrigation System Rain Gutters Sliding Doors
Water Source Public
Lot Size Area 7722
Foundation Details Basement
Building Area Total 4260
Lot Size Acres 0.18
Road Surface Type Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Beycome Of Florida Llc

Broker

contact@beycome.com

Email

Affordability Calculator

$8,918
Per Month
88%
12%
0%
Monthly Principal & Interest
$7,875
Monthly Property Taxes
$1,043
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
5/28/2026$1,279,000 Listed Price

Map


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442 WOODLAND STREET, Orlando, FL, 32806 is a Single Family Home for sale at $1,279,000 with 2,828 sqft and a lot size of 0.18. 442 WOODLAND STREET has 4 bedrooms, 2.1 baths, and was built in 1927. The property's zip code is 32806 which is in Orlando, FL