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40 W Smith St, Winter Garden, FL 34787

PENDING $750,000
Charming two-story home with a well-manicured lawn, classic architecture, and inviting front entrance at 40 W Smith St, Winter Garden, FL 34787

  • Bedrooms

    3

  • Baths

    2

  • Sq. Feet

    2225

  • Year Built

    1923

  • Days On Market

    45

  • $/SqFt

    $337

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43 Photos

  • Charming two-story home with a well-manicured lawn, classic architecture, and inviting front entrance at 40 W Smith St, Winter Garden, FL 34787
  • Inviting sun porch with rocking chairs, carpet floor, and an abundance of natural light through the windows at 40 W Smith St, Winter Garden, FL 34787
  • Cozy living room with a painted fireplace, wood floors, grey sofa, and stylish decor at 40 W Smith St, Winter Garden, FL 34787
  • Bright living room featuring hardwood floors, a fireplace, stylish furniture, and an open layout at 40 W Smith St, Winter Garden, FL 34787
  • Open-concept layout connecting the living room with hardwood floors to the dining area and lots of natural light at 40 W Smith St, Winter Garden, FL 34787
  • Elegant dining room featuring hardwood floors, neutral walls, stylish light fixture and a decorative painting at 40 W Smith St, Winter Garden, FL 34787
  • Bright dining area with hardwood floors, chandelier, open to the living area, and ample natural light at 40 W Smith St, Winter Garden, FL 34787
  • Cozy kitchen featuring stainless steel appliances, ample natural light, and black-and-white checkered floors at 40 W Smith St, Winter Garden, FL 34787
  • Bright kitchen with stainless steel appliances, hardwood floors, shaker cabinets, and an open design at 40 W Smith St, Winter Garden, FL 34787
  • Cozy dining nook with a breakfast table, natural light, and the black-and-white checkered flooring at 40 W Smith St, Winter Garden, FL 34787
  • Galley kitchen featuring checkerboard floors, white cabinetry, and stainless steel appliances at 40 W Smith St, Winter Garden, FL 34787
  • Bedroom with hardwood floors, ceiling fan, and four-poster bed in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Bedroom with hardwood floors, ceiling fan, fireplace and period furnishings in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Bedroom with hardwood floors, and antique furnishings in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Sitting room with hardwood floors and a mini fridge off of bedroom in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Hallway and stairway with hardwood floors and white molding in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Bedroom with hardwood floors and white furniture in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Bedroom with hardwood floors, white furniture, and ensuite bathroom in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Bedroom with hardwood floors, white furniture, and walk-in closet in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Bathroom with green walls and a walk-in shower in a home for sale at 40 W Smith St, Winter Garden, FL 34787
  • Bright home office with custom shelving, hardwood floors, a computer, and a comfortable vintage style chair at 40 W Smith St, Winter Garden, FL 34787
More Photos \/
  • Retro pink and white tiled bathroom with a vintage sink, bathtub, shower, and black and white checkerboard flooring at 40 W Smith St, Winter Garden, FL 34787
  • Classic pink and white bathroom featuring pedestal sink, toilet and a doorway showing an adjacent office space at 40 W Smith St, Winter Garden, FL 34787
  • Well-lit laundry room with black and white checkerboard floor, and updated countertops and cabinets at 40 W Smith St, Winter Garden, FL 34787
  • Laundry room with a full sized washer and dryer and black and white checkerboard floors near the back door at 40 W Smith St, Winter Garden, FL 34787
  • Bright attic space with finished walls, carpet and a staircase leading to another level of the home at 40 W Smith St, Winter Garden, FL 34787
  • Spacious attic with carpet, white paneled walls, a window, and ample storage space with sliding closet doors at 40 W Smith St, Winter Garden, FL 34787
  • Spacious attic with carpet, finished walls, and a view of the door leading to a separate room at 40 W Smith St, Winter Garden, FL 34787
  • Bright attic with paneled walls, large windows, finished carpet, sliding closet doors, and unique ceiling at 40 W Smith St, Winter Garden, FL 34787
  • Spacious attic with carpet, paneled walls, a door to closet, and a unique ceiling at 40 W Smith St, Winter Garden, FL 34787
  • Relaxing sunroom with rocking chairs, large windows and carpeted floors offering a tranquil space to unwind at 40 W Smith St, Winter Garden, FL 34787
  • Outdoor deck featuring a seating area with an umbrella providing a cozy spot for entertaining and relaxing at 40 W Smith St, Winter Garden, FL 34787
  • Backyard deck overlooking mature trees, a detached garage, and providing a serene outdoor living space at 40 W Smith St, Winter Garden, FL 34787
  • Charming single-Gathering home boasting a screened porch, mature landscaping, and a detached garage at 40 W Smith St, Winter Garden, FL 34787
  • Backyard featuring a detached garage, brick patio, well-manicured lawn, and mature landscaping at 40 W Smith St, Winter Garden, FL 34787
  • Spacious backyard with a deck, mature trees, providing ample space for outdoor activities and relaxation at 40 W Smith St, Winter Garden, FL 34787
  • Backyard with a trellis and detached garage with mature trees, offering a peaceful and private outdoor setting at 40 W Smith St, Winter Garden, FL 34787
  • Aerial view of a home with a well-maintained roof, backyard deck, and mature trees surrounding the property at 40 W Smith St, Winter Garden, FL 34787
  • Aerial view showcasing the roof, backyard, detached garage, and mature trees creating a private oasis at 40 W Smith St, Winter Garden, FL 34787
  • Aerial view featuring a house surrounded by mature trees and foliage providing shade and privacy at 40 W Smith St, Winter Garden, FL 34787
  • Expansive aerial view showcases downtown area with mature trees and a large parking garage at 40 W Smith St, Winter Garden, FL 34787
  • Charming traditional home with a gabled roof, covered porch, and lush landscaping at 40 W Smith St, Winter Garden, FL 34787
  • Close-up of front exterior with a cozy screened in porch and manicured hedges at 40 W Smith St, Winter Garden, FL 34787
Less Photos /\

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Home Description

Under contract-accepting backup offers. Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled in the heart of downtown Winter Garden, enjoy easy access to the widely popular Plant Street farmer's market, West Orange Trail, and the famed Crooked Can Brewery. This prime location home is nestles in the heart of downtown Winter Garden with easy access to local shops, restaurants, parks, and the vibrant community events that define this sought-after area. Original architectural details reflects the home's 1920's heritage, offering a unique blend of past and present. Some of modern highlights include Brazilian Cherry hardwood floors, Roof 2018, AC 2019, and replumbed in 2020. Your spacious living amenities include 3 bedrooms with large walk-in closets, 2 full bathrooms, and an ample upstairs retreat generous enough for families or those seeking to room to grow. Don't miss the opportunity to own a piece of Winter Garden's history. Schedule your private showing today and envision the endless possibilities this home has.

  • MLS #: O6306766
  • Address: 40 W Smith St
  • Levels: Two
  • City: Winter Garden
  • Zip: 34787
  • County: Orange
  • Community Features: Street Lights
  • Elementary School: Dillard Street Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High
  • Private Pool: False
  • Water Feet: 0
  • Interior Features: Ceiling Fans(s),Primary Bedroom Main Floor,Walk-In Closet(s)
  • Appliances: Cooktop,Dishwasher,Dryer,Microwave,Tankless Water Heater,Washer
  • Fireplace Desc: Family Room,Wood Burning
  • Floor Covering: Hardwood,Luxury Vinyl
  • Exterior Features: Garden
  • Exterior Contruction: Frame
  • Foundation: Crawlspace
  • Front Exposure: North
  • Roof: Shingle
  • Building Sqft: 2225

Approximate Room Sizes / Descriptions

Living Room13x13FirstWood
Dining Room13x13First
Kitchen13x10FirstVinyl
Laundry12x11Basement
Office7x7First
Bathroom 15x7First
Primary Bathroom7x5First
Media Room24x14Second
Primary Bedroom13x13First
Bedroom 213x13First
Bedroom 314x12Second
  • Attached Garage: False
  • Garage: True
  • Garage Spaces: 1
  • Garage Feature: Garage Door Opener,Golf Cart Garage
  • Carport: False
  • Carport Spaces: 0
  • Air Conditioning: Central Air
  • Heating: Central
  • Utilities: Public,Water Connected
  • Lot Sqft: 9464.00
  • Lot Acres: 0.2200
  • Total Acre: 0 to less than 1/4
  • Lot Num: 1
  • Senior Community: False
  • Style: Single Family Residence
  • Building Num Floors: 2
  • : 407-203-6903

Neighborhood

The average asking price of a 3 bedroom Winter Garden home in this zip code is $575,404 (23.3% less than this home).

This home is priced at $337/sqft, which is 10.8% less than similar homes in the 34787 zip code.

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Financial

  • Approx Payment:$3,648*
  • Taxes:$1,679

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (386) 801-5417 and speak with one of our real estate consultants.

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Listing Courtesy of NATIONAL REAL ESTATE LLC.

40 W Smith St, Winter Garden FL is a single family home of 2225 sqft and is currently priced at $750,000 . This single family home has 3 bedrooms. A comparable home for sale at 11188 Hollow Bay Dr in Winter Garden is listed at $584,190. In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures in Winter Garden, FL. Oxford Chase, Watermark and Courtlea Oaks are nearby neighborhoods. MLS O6306766 has been posted on this site since 5/14/2025 (today).

2025 6/26/2025.

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