NOT LISTED FOR SALE

423 N Main St Winter Garden, FL 34787

Estimated Value: $617,000 - $655,000

3 Beds
2 Baths
1,668 Sq Ft
$382/Sq Ft Est. Value

Sale Details

Date Sold: September 26, 2025

Last sale price $655,000 $393 Per Sq Ft

Est. 3% decrease in value since last sale

Current estimated payment $4,042 / mo

26 Days on Market

Highlights

  • Heated In Ground Pool
  • Ranch Style House
  • Mud Room
  • West Orange High School Rated A
  • Engineered Wood Flooring
  • Stone Countertops

About This Home

As of September 2025

Mid-Century Charm Meets Modern Comfort in Winter Garden!

Discover the perfect blend of classic appeal and contemporary upgrades in this delightful 3-bedroom, 2-bath pool home, ideally situated on a generous .30+ acre lot just blocks from downtown Winter Garden. Best of all, there's no HOA!

Step inside and appreciate the thoughtful updates that complement the home's timeless mid-century architecture. The kitchen boasts updated Bosch appliances, including a 2021 induction range and 2023 wall oven for a total of two ovens, along with quartz countertops and an updated farm sink. You'll find engineered hardwood floors in the family room, kitchen, and hallway, and custom window blinds throughout. Peace of mind comes with a brand-new roof (July 2025), rain gutters, an AC unit replaced in 2019, and a gas hot water heater from 2018.

The primary bedroom suite offers three deep closets with custom doors and a renovated en-suite bath (2021) featuring new tile, a walk-in low threshold shower, and modern fixtures that maintain the home's classic character. The hall bath was also renovated in 2023 with new tile and paint. The dining room provides a cozy ambiance with a gas fireplace and built-in shelves, while French doors open to a spacious 26x17 covered and screened back porch wired with Bluetooth speakers and also has a 220 power hookup for a hot tub. A versatile mud room/art studio/office and a dedicated laundry room add to the home's functionality.

The outdoor living space is a true oasis, featuring a fenced backyard (2019) with an amazing heated saltwater pool (2019), complete with a sun ledge. The yard is kept lush with an irrigation system fed by a well (pump replaced 2020) and a French drain system (2019) for optimal drainage. The north gate is a double gate, allowing boat or RV parking behind the fence, with an RV electric outlet on the side of the house. Plus, there's a large elevated workshop building with electricity and AC for your projects (As Is). In 2023, a variance was obtained through the City of Winter Garden to build a new structure where the current workshop sits, which also allows for an attached covered veranda to be built.

Beyond your doorstep, the vibrant heart of Winter Garden awaits. This home is located in the golf cart district, allowing you to drive your own golf cart on approved roads. Enjoy leisurely strolls to the weekend farmers market, participate in festive holiday events, and explore a diverse array of restaurants and shops. You're also within walking distance to Lake Apopka, where breathtaking sunsets are a daily spectacle, and it's renowned as one of Florida's top three birding areas. The Jessie Brock Community Center (offering exercise and Crealde art classes) and its pond with a paved walking circuit and exercise stations are also just a short walk away, as is the West Orange Bike Trail.

This Winter Garden gem offers not just a home, but a lifestyle. Don't miss your chance to own a piece of this charming and convenient community!

Last Agent to Sell the Property

Paul Giles

COMPASS FLORIDA LLC Brokerage Phone: 407-203-9441 License #678941 Listed on: 08/01/2025

COMPASS FLORIDA LLC

Last Buyer's Agent

Andrea Summers

COLDWELL BANKER HUBBARD HANSEN License #3277956

COLDWELL BANKER HUBBARD HANSEN

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $3,410

Year Built

  • Built in 1957

Lot Details

  • 13,147 Sq Ft Lot
  • West Facing Home
  • Vinyl Fence
  • Landscaped

Parking

  • 2 Car Attached Garage
  • Driveway

Home Design

  • Ranch Style House
  • Slab Foundation
  • Shingle Roof
  • Block Exterior

Interior Spaces

  • 1,668 Sq Ft Home
  • Ceiling Fan
  • Gas Fireplace
  • Double Pane Windows
  • Blinds
  • Mud Room
  • Living Room
  • Formal Dining Room
  • Home Office
  • Inside Utility
  • Laundry Room

Kitchen

  • Built-In Convection Oven
  • Cooktop
  • Bosch Dishwasher
  • Stone Countertops
  • Farmhouse Sink
  • Disposal

Flooring

  • Engineered Wood
  • Parquet
  • Concrete
  • Ceramic Tile

Bedrooms and Bathrooms

  • 3 Bedrooms
  • 2 Full Bathrooms

Pool

  • Heated In Ground Pool
  • Saltwater Pool

Outdoor Features

  • Covered Patio or Porch
  • Separate Outdoor Workshop
  • Rain Gutters

Schools

  • Dillard Street Elementary School
  • Lakeview Middle School
  • West Orange High School

Utilities

  • Central Heating and Cooling System
  • Gas Water Heater
  • High Speed Internet
  • Cable TV Available

Community Details

  • No Home Owners Association
  • Winter Garden Shores First Add Subdivision

Listing and Financial Details

Home Details

Home Type

Single Family

Est. Annual Taxes

$3,410

Year Built

Built in 1957

Lot Details

0.3 Acres

Parking

2

Listing Details

  • Property Type: Residential
  • Property Condition: Completed
  • Property Sub Type: Single Family Residence
  • Architectural Style: Ranch
  • Construction Materials: Block
  • Fireplace: Yes
  • Living Area: 1668
  • Lot Size Acres: 0.3
  • New Construction: No
  • Year Built: 1957
  • Building Area Total: 2249
  • Lot Size Sq Ft: 13147
  • Status: Sold
  • Street Direction: N
  • Ownership: Fee Simple
  • Building Area Total Srch Sq M: 208.94
  • Escrow City: DeLand
  • Escrow State: FL
  • Escrow Street Name: E New York Avenue ste 103XX
  • Minimum Lease: 8-12 Months
  • RATIO Current Price By Calculate: 392.69
  • Total Acreage: 1/4 to less than 1/2
  • Water Access YN: 0
  • MFR_InLawSuiteYN: 0
  • Attribution Contact: 407-203-9441
  • Tax Year: 2024
  • Special Features: VirtualTour

Interior Features

  • Fireplace Features: Gas
  • Living Area Units: Square Feet
  • Flooring: Ceramic Tile, Concrete, Hardwood, Parquet
  • Full Bathrooms: 2
  • Interior Amenities: Ceiling Fans(s), Solid Surface Counters, Stone Counters
  • Appliances Included: Built-In Oven, Convection Oven, Cooktop, Disposal, Gas Water Heater, Refrigerator
  • Foundation Details: Slab
  • Total Bedrooms: 3
  • Levels: One
  • Spa Yn: No
  • Window Features: Blinds, Double Pane Windows
  • Additional Rooms: Den/Library/Office,Formal Dining Room Separate,Inside Utility
  • Living Area Meters: 154.96

Exterior Features

  • Direction Faces: West
  • Other Structures: Workshop
  • Pool Features: Heated, In Ground, Salt Water
  • Exterior Features: Rain Gutters
  • Roof: Shingle
  • Pool Private: Yes
  • Waterfront: No
  • Patio and Porch Features: Covered, Patio, Rear Porch, Screened
  • Road Surface Type: Asphalt, Paved
  • Water View YN: 0
  • Waterfront Feet Total: 0
  • Flood Zone Panel: 12095C0205H

Garage/Parking

  • Attached Garage: Yes
  • Carport Y N: No
  • Garage Spaces: 2
  • Garage Yn: Yes
  • Parking Features: Driveway

Utilities

  • Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Fiber Optics, Natural Gas Available, Natural Gas Connected, Public, Sewer Connected
  • Cooling: Central Air
  • Heating: Central
  • Laundry Features: Inside, Laundry Room
  • Sewer: Public Sewer
  • Water Source: Public

Condo/Co-op/Association

  • Association: No
  • Senior Community: No
  • Association 2 YN: 0
  • Pet Restrictions: Check with City and County

Fee Information

  • Total Annual Fees: 0.00
  • Total Monthly Fees: 0.00

Schools

  • Elementary School: Dillard Street Elem
  • High School: West Orange High
  • Middle Or Junior School: Lakeview Middle

Lot Info

  • Zoning: R-1
  • Parcel Number: 14-22-27-9388-01-090
  • Additional Parcels: No
  • Fencing: Vinyl
  • Lot Features: Landscaped, Paved
  • Flood Zone Code: X

Rental Info

  • Pets Allowed: Cats OK, Dogs OK
  • Lease Restrictions YN: 0
  • Additional Lease Restrictions: Check with city and county

Tax Info

  • Tax Annual Amount: 3410
  • Tax Block: A
  • Tax Book Number: T-86
  • Tax Lot: 9

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
Aug 1, 2025
Closed on
Sep 26, 2025
Sold by
Headley Thomas and Headley Family Trust
Bought by
Ferguson Sky W and Brown Kimberly D
Seller's Agent
Paul Giles
COMPASS FLORIDA LLC
Buyer's Agent
Andrea Summers
COLDWELL BANKER HUBBARD HANSEN
List Price
$680,000
Sold Price
$655,000
Premium/Discount to List
-$25,000
-3.68%
Views
48
Current Estimated Value
$637,376

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
-$17,624
Avg. Annual Appreciation
-4.30%

Purchase Details

Closed on
Feb 4, 2021
Sold by
Headley Thomas and Headley Lisa T
Bought by
Headley Family Trust and Headley

Purchase Details

Closed on
Mar 9, 2017
Sold by
Peters William R and Peters Vicki L
Bought by
Headley Thomas W and Headley Lisa T

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$215,200
Interest Rate
3.41%
Mortgage Type
New Conventional

Purchase Details

Closed on
Mar 11, 1998
Sold by
Harry L Miller Tr and Esther H Miller Tr
Bought by
Peters William R and Peters Vicki L

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$70,800
Interest Rate
7.07%
Mortgage Type
New Conventional
Source: Public Records
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Buyer Sale Price Title Company
Ferguson Sky W $655,000 Premier Partners Title
Headley Family Trust $100 None Listed On Document
Headley Thomas W $275,000 Equitable Title Of Mid Flori
Peters William R $73,000 --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Borrower Loan Amount
Previous Owner Headley Thomas W $215,200
Previous Owner Peters William R $101,000
Previous Owner Peters William R $70,800
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
09/26/2025 09/26/25 Sold $655,000 -0.6% $393 / Sq Ft
08/27/2025 08/27/25 Pending -- -- --
08/26/2025 08/26/25 Price Changed $659,000 -3.1% $395 / Sq Ft
08/01/2025 08/01/25 For Sale $680,000 -- $408 / Sq Ft
Source: Stellar MLS

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2026 $7,717 $468,170 $175,500 $292,670
2025 $7,717 $473,580 $175,500 $298,080
2024 $3,283 $260,980 -- --
2023 $3,283 $246,238 $0 $0
2022 $3,181 $239,066 $0 $0
2021 $3,130 $232,103 $0 $0
2020 $2,980 $228,898 $0 $0
2019 $2,665 $199,314 $0 $0
2018 $2,638 $195,598 $0 $0
2017 $1,164 $222,073 $75,000 $147,073
2016 $1,155 $167,908 $60,000 $107,908
2015 $1,176 $163,627 $60,000 $103,627
2014 $1,182 $138,816 $60,000 $78,816
Source: Public Records

Agents Affiliated with this Home

  • Section Image
  • Section Image
See All Agents

Map

Source: Stellar MLS

MLS Number: O6331314

Stellar MLS

APN: 14-2227-9388-01-090

Your Personal Tour Guide

Ask me questions while you tour the home.