$1,279,000
442 Woodland Street
Orlando, FL 32806
Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
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
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
- Status: ActiveMay 28, 2026
- Listed$1,279,000May 28, 2026
- 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
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | Second | |
| Bedroom 1 | Second | |
| Bedroom 2 | Second | |
| Bedroom 3 | Second | |
| Basement | Basement | |
| Basement | Basement | |
| Kitchen | First | |
| Living Room | First | |
| Dining Room | First |
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-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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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.
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