442 WOODLAND STREET ORLANDO FL 32806 MLS #O6411598

442 WOODLAND STREET ORLANDO FL 32806 MLS #O6411598

442 WOODLAND STREET
ORLANDO, FL, 32806
$1,279,000
4 Beds
2.5 Baths
2,828 SqFt
0.18 Acres
Add
MLS #O6411598 image #0
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

Property Details

Price:
$1,279,000
MLS #:
O6411598
Status:
Active
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
LANCASTER HEIGHTS
Neighborhood:
32806orlandodelaneyparkcrystallake
Listed Date:
May 28, 2026
Finished Sq Ft:
2,828
Total Sq Ft:
4,260
Lot Size:
7,722 sqft / 0.18 acres (approx)
Year Built:
1927
Pool32806 – Orlando/delaney Park/crystal Lake32806orlandodelaneyparkcrystallakeLancaster HeightsN/a1 Month

Ask a Question

See this Listing

Send
  

Schools

Interior

Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Touchless Faucet, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Tile, Hardwood
Heating
Central, Heat Pump, Zoned
Interior Features
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)
Laundry Features
Laundry Room, Upper Level
Levels
Two

Exterior

Construction Materials
Stucco
Covered Spaces
2
Direction Faces
North
Exterior Features
Awning(s), Balcony, Courtyard, Garden, Irrigation System, Rain Gutters, Sliding Doors
Roof
Shingle

Financial

Tax Year
2025
Taxes
$12,517

Map

Community

Subdivisions in ORLANDO

Market Summary

Current real estate data for Single Family in ORLANDO as of May 31, 2026
3,110
Single Family Listed
98
Avg DOM
288
Avg $ / SqFt
$674,184
Avg List Price

Property Summary

    Located in the LANCASTER HEIGHTS subdivision, 442 WOODLAND STREET ORLANDO FL is a Single Family for sale in ORLANDO, FL, 32806. It is listed for $1,279,000 and features 4 beds, 3 baths, and has approximately 2,828 square feet of living space, and was originally constructed in 1927. The current price per square foot is $452. The average price per square foot for Single Family listings in ORLANDO is $288. The average listing price for Single Family in ORLANDO is $674,184. To schedule a showing of MLS#o6411598 at 442 WOODLAND STREET in ORLANDO, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.

Similar Listings Nearby

broker reciprocity
MLS# O6403476broker reciprocity
18 E STEELE STREET
ORLANDO, FL

$1,650,000

4.0 miles away

broker reciprocity
MLS# O6407841broker reciprocity
1841 LAKE SPIER DRIVE
WINTER PARK, FL

$1,650,000

4.5 miles away

broker reciprocity
MLS# O6398694broker reciprocity
1565 FOREST AVENUE
WINTER PARK, FL

$1,650,000

4.5 miles away

broker reciprocity
MLS# S5145299broker reciprocity
3807 S SEMORAN BOULEVARD
ORLANDO, FL

$1,649,000

4.1 miles away

broker reciprocity
MLS# O6385666broker reciprocity
1326 W NEW HAMPSHIRE STREET
ORLANDO, FL

$1,649,000

3.5 miles away

broker reciprocity
MLS# O6384756broker reciprocity
2501 ROAD
WINTER PARK, FL

$1,649,000

3.7 miles away

broker reciprocity
MLS# O6404418broker reciprocity
722 GOLFVIEW STREET
ORLANDO, FL

$1,629,900

3.1 miles away

broker reciprocity
MLS# A4667662broker reciprocity
4358 TIDEWATER DRIVE
ORLANDO, FL

$1,625,000

3.1 miles away

broker reciprocity
MLS# O6363933broker reciprocity
5526 PARKDALE DRIVE
ORLANDO, FL

$1,599,999

3.1 miles away

broker reciprocity
MLS# O6350503broker reciprocity
1510 MILLER AVENUE
WINTER PARK, FL

$1,599,900

4.5 miles away

442 WOODLAND STREET
ORLANDO, FL

Schedule An Appointment!

Our team has decades of experience working with buyers and sellers, providing a stress-free experience with proven results.