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442 WOODLAND STREET ORLANDO FL 32806

$1,279,000
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Under Contract
442 WOODLAND STREET, ORLANDO, FL 32806 - MLS#MFRO6411598 442 WOODLAND STREET, ORLANDO, FL 32806 - MLS#MFRO6411598 442 WOODLAND STREET, ORLANDO, FL 32806 - MLS#MFRO6411598 442 WOODLAND STREET, ORLANDO, FL 32806 - MLS#MFRO6411598

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 442 Woodland St

4 Bedrooms
3/1 Bathrooms
Car Garage
4,260 Square Feet
2,828SF Living Area
Pool:
Yes
Water: None
Year Built 1927
Listed For 6 Days

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

This luxury single family home was built in 1927 and features 4 bedrooms, and 3 full bathrooms plus 1 half bath. This home for sale is 4,260 square feet, with 2,828 sq ft being air conditioned living space. The home has a has a private swimming pool.

Directions to this property are as follows: 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.

Please contact your BEX agent for more information about MLS# MFRO6411598 or any other homes for sale in Orlando or elsewhere in the Orange County area.

Features & Amenities

Appliances

Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Touchless Faucet, Washer

Other Equipment

Irrigation Equipment

Cooling

Central Air, Zoned

Heating

Central, Heat Pump, Zoned

Flooring

Tile, Wood

Lot Size

7722

View

view

Construction Materials

Stucco

Interior Features

Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Primary Bedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)

Furnished

Unfurnished

Exterior Features

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

Pool Features

Fiber Optic Lighting, Gunite, Heated, In Ground, Pool Alarm, Salt Water, Tile

Roof

Shingle

Utilities

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

Laundry

Laundry Room, Upper Level

Fireplace

Gas, Living Room

Zoning

R-1/T

Year Built

1927

Annual Real Estate Taxes

$12,517 (2025)

Legal Description

Lancaster Heights H/77 Lot 9 Blk J

Property Type

Single Family Home

Direction Faces

North

MLS Number

MFRO6411598

Universal Property Id

U S-12095-N-012329496010090-R-N

Days On Market

6

Community Name

Lancaster Heights

442 Woodland Street Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 442 Woodland St should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $12,517 but will likely change when this home sells. These estimations are calculated from a list price of $1,279,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 442 Woodland Street

Address Sale Price Bed Bth Size Location Sale Date
No comps found for this property

MLS# MFRO6411598 Listing History

05/28/2026 Listed for sale by BEYCOME OF FLORIDA LLC with MLS# MFRO6411598 with a list price of $1,279,000.

Orange County Schools

High School

This listing of 442 Woodland Street Orlando FL 32806 was last updated on 2026-06-03 15:12:10. Listing courtesy of BEYCOME OF FLORIDA LLC.
MLS

Map of 442 Woodland Street Orlando FL 32806

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the BEX Realty website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. BEX Realty, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed.

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