$1,279,000

442 Woodland Street

Orlando, FL 32806

Active
4
Beds
3
Baths
2,828
Sq Ft
0.18
Acres
1927
Built
Private poolFireplace$452/sqft360° tour
🏠Single Family Residence

Property type

🏗️1927

Year built

📐7,722 sqft

Lot size

📊$452

Price / sq ft

🏘️No HOA

HOA dues

📅1

Day on market

🌊X

Flood zone

About this home

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

Estimated monthly payment

Principal & interest$6,467
Property taxes$1,043
Home insurance (est.)$586

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history1 days on market

  1. Status: Active
    May 28, 2026
  2. Listed$1,279,000
    May 28, 2026
  3. Price increased$1,279,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
1
Subdivision
Lancaster Heights
County
Orange
Year built
1927
Living area
2,828 sq ft
Price/sq ft
$452
Building area
4,260 sq ft (Owner)
Lot size
7,722 sq ft
Lot category
0 to less than 1/4
Flood zone
X (12095C0265F)
Pool
Private pool
Annual taxes
$12,517 (2025)
Parcel #
01-23-29-4960-10-090
Zoning
R-1/T
MLS #
O6411598

Interior Details

Bedrooms
4
Full bathrooms
2
Half bathrooms
1
Flooring
Tile, Wood
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Touchless Faucet, Washer
Interior features
Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry
Laundry Room, Upper Level
Stories / Levels
Two
Direction faces
North
Fireplace
Yes

Heating & Cooling

Heating
Central, Heat Pump, Zoned
Cooling
Central Air, Zoned

Parking

Carport
Yes

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Min lease term
1 Month
Listing terms
Cash, Conventional, FHA, Other, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
n/a

Exterior & Construction

Exterior features
Awning(s), Balcony, Courtyard, Garden, Rain Gutters, Sliding Doors
Construction materials
Stucco
Roof
Shingle
Foundation
Basement
Pool
Private pool
Road surface
Paved

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Sewer Connected, Sprinkler Well, Water Connected

Room Details

RoomLevelDimensions
Primary BedroomSecond
Bedroom 1Second
Bedroom 2Second
Bedroom 3Second
BasementBasement
BasementBasement
KitchenFirst
Living RoomFirst
Dining RoomFirst

Listing Details

Listing date
2026-05-28
On market date
2026-05-28
Original list price
$1,279,000
Occupant type
Owner
MLS area
32806 - Orlando/Delaney Park/Crystal Lake
Listing AOR
Orlando Regional
Status changed
2026-05-28
Tax legal description
LANCASTER HEIGHTS H/77 LOT 9 BLK J

Flood risk

Minimal riskFEMA Zone XPanel 12095C0265F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of May 29, 2026 at 10:22 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA