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Eileen Astra
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442 Woodland Street, Orlando, FL 32806

$1,279,000
  • 442 Woodland Street, Orlando, FL 32806 Main Photo

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New to the Market Active
BEDS4 BATHS2 full 1 partial SQUARE FEET2,828 MLS#O6411598
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONLANCASTER HEIGHTS

Property Description

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

442 Woodland Street | MLS# O6411598

This single family home located at 442 Woodland Street, Orlando, FL 32806 is currently listed for sale with an asking price of $1,279,000. This property was built in 1927 and has 4 bedrooms and 2 full and 1 partial baths with 2828 sq. ft. Woodland Street is located in the LANCASTER HEIGHTS subdivision. Search LANCASTER HEIGHTS real estate on eastra.floridaexecutiverealty.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Cooling: Central Air, Zoned
Heating: Central, Heat Pump, Zoned
Lot Size: 0.18 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $12,517
Year Built: 1927

Amenities

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)
Awning(s)
Balcony
Courtyard
Garden
Rain Gutters
Sliding Doors

Feature Descriptions

Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Touchless Faucet, Washer
Days on Site: 1
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
Exterior: Stucco
Fireplace: Gas, Living Room
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Tile, Wood
Foundation: Basement
Home Warranty Y/N: No
Listing Terms: Cash, Conventional, FHA, Other, VA Loan
Lot Dimensions: 0.18
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Pool: Fiber Optic Lighting, Gunite, Heated, In Ground, Pool Alarm, Salt Water, Tile
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: Call Owner
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Sewer Connected, Sprinkler Well, Water Connected
Water: Public
Water Access Y/N: No
Zoning: R-1/T

Listed By / Shown By

Listed By

Agency Name: BEYCOME OF FLORIDA LLC
Agency Contact: 844-239-2663

Shown By

Agent Name: Eileen Astra
Agent Phone: Cell: (727) 247-9247
Agency Title: Florida Executive Realty

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Estimated Payment

$ 4,262.62 per month $2,846.50 Principal & Interest $1,043.08 Property Tax $373.04 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 05/30/2026. The listing information on this page last changed on 05/30/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 05/30/2026 12:00:23 AM EST) or Stellar MLS (last updated Fri 05/29/2026 11:45:12 PM EST). Real estate listings held by brokerage firms other than Florida Executive Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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