299 W 4th Ave

Windermere, FL 34786

$895,000
Price
4
Beds
2,410 Sq. Ft.
$371 / Sq. Ft.
2,410
Sq. Ft.
$371
per Sq. Ft.
Pending
Pending
a view of a house with a yard patio and a small yard
a view of a house with a yard porch and sitting area
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a living room with furniture and a large window
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a kitchen with granite countertop a sink and wooden cabinets
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a bedroom with a large bed and a large window
a bedroom with a bed and a large window
a bathroom with a sink and a mirror
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a bathroom with a granite countertop sink a toilet and shower
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Description

This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, relax, and enjoy the neighborhood setting. Step inside to original wood floors that extend throughout the main living areas, enriching the home with warmth and timeless appeal. The family room centers around...This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, relax, and enjoy the neighborhood setting. Step inside to original wood floors that extend throughout the main living areas, enriching the home with warmth and timeless appeal. The family room centers around a charming wood-burning fireplace, surrounded by newly installed windows (2020) that fill the space with natural light. French doors open to a large screened porch — an ideal spot for morning coffee, outdoor dining, or unwinding beneath the shade of mature trees. The island kitchen features granite countertops and generous workspace for cooking and entertaining. The first floor includes a full bedroom and bath, perfect for guests or a home office. Upstairs, the spacious primary suite offers a peaceful retreat, joined by two additional bedrooms and the convenience of a second-floor laundry room. New Septic and drain field 2020, A/C 2024, Well re-sleaved and new pump 2024. A partially air-conditioned, three-car garage provides excellent storage and space for vehicles, golf carts, or weekend adventure gear. Stroll or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience.

Property Details for 299 West 4th Avenue

Architectural Style
Craftsman
Subdivision Name
WINDERMERE TOWN
Township
23
Garage Spaces
3
View
Trees/Woods
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 12/13/2025 06:23 AM

Property Details for 299 West 4th Avenue

StatusPending
MLS #O6357207
Days on Market35
Taxes$10,545 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1984
Lot Size0.38 AC / 16,750 SF
CountyOrange County

Location

Listing Courtesy of UPSIDE REAL ESTATE INC, Judy Black; UPSIDE REAL ESTATE INC, Amanda Black PA
Add your commute

Building Information for 299 West 4th Avenue

Stories2Year Built1984Building Size-Lot Size0.38 AC / 16,750 SF

Payment Calculator

$5,301 per month

30 year fixed, 6.28% Interest

Principal and Interest

$4,423

Property Taxes

$879

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 299 West 4th Avenue

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 3936.0
  • Building Area Units: Square Feet
  • Community Features: Golf Carts OK, Park, Playground, Restaurant, Tennis Court(s)
  • Direction Faces: South
  • Directions: From Main Street go West on 3rd, left on Butler. House on the NE corner of 4th and Butler.
  • Elementary School: Windermere Elem
  • Middle Or Junior School: Gotha Middle
  • High School: Olympia High
  • Mls Major Change Type: Pending
  • Major Change Type: Pending
  • Listing Service: Full Service
  • Road Frontage Type: Street Unpaved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 299
  • Street Direction Prefix: W
  • Street Name: 4TH
  • Street Suffix: AVENUE
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage Dimensions: 34x24
  • Garage: Yes
  • Parking Features: Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Taxes and HOA Information
  • Association Approval Required: No
  • Association: No
  • CDD: No
  • Tax Block: 3
  • Tax Book Number: G-36
  • Tax Legal Description: PLAT OF WINDERMERE G/36 LOT 320 IN SEC 8-23-28 SW1/4
  • Tax Lot: 320
  • Tax Year: 2024
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Additional Water Information: 3 Blocks to public access for Lake Butler
  • Lot Features: Corner Lot, City Lot, Near Golf Course
  • Parcel Number: 172328933603200
  • Total Acreage: 1/4 to less than 1/2
  • Water Access: Lake - Chain of Lakes
  • Water Access: Yes
  • Water Extras: No
  • Zoning: SFR
  • Zoning Compatible: Yes
  • Living Area: 2410
Property and Assessments
  • Year Built Numeric: 1984
  • Amenities Additional Fees: Boat Ramp and Tennis with minimal annual fee.
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0385F
  • Homestead: No
  • New Construction: No
  • Public Survey Range: 28
  • Public Survey Section: 17
  • Dock YN: No
Utilities
  • Green Energy Efficient: Windows
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Electricity Connected
  • Water Source: Well
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Siding
  • Exterior Features: French Doors, Private Mailbox
  • Foundation Details: Crawlspace
  • Levels: Two
  • Patio And Porch Features: Covered, Front Porch, Rear Porch, Screened
  • Pool Private: No
  • Pool: None
  • Pool Private: No
  • Roof: Shingle
  • Spa: No
  • Vegetation: Bamboo, Fruit Trees, Oak Trees
  • Waterfront Feet Total: 0
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 3
  • Additional Rooms: Inside Utility
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Washer
  • Cooling: Central Air
  • Fireplace Features: Family Room, Wood Burning
  • Fireplace: Yes
  • Flooring: Laminate, Hardwood
  • Heating: Central, Electric
  • Interior Features: Ceiling Fan(s), Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s)
  • Laundry Features: Inside, Laundry Room, Upper Level
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 7.0
  • Water View: No
  • Window Features: Insulated Windows
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 0

Property History for 299 West 4th Avenue

DateEvent & SourcePriceAppreciation
Dec 12, 2025

Pending

MFRMLS #O6357207

—
Nov 7, 2025

Listed (Active)

MFRMLS #O6357207

$895,000—
Jan 2, 2025

Sold (Public Record)

Public Record #1548447889

$650,000

+7.7% / yr

Apr 19, 2019

Sold

MFRMLS #O5747950

$425,000—
Apr 18, 2019

Sold (Public Record)

Public Record #643461069

$425,000—
Mar 6, 2019

Pending

MFRMLS #O5747950

—
Nov 20, 2018

Listed (Active)

MFRMLS #O5747950

$549,900—
DateEvent & SourcePrice
12/12/2025

Pending

MFRMLS #O6357207

—
11/07/2025

Listed (Active)

MFRMLS #O6357207

$895,000
01/02/2025

Sold (Public Record)

Public Record #1548447889

$650,000

+7.7% / yr

04/19/2019

Sold

MFRMLS #O5747950

$425,000
04/18/2019

Sold (Public Record)

Public Record #643461069

$425,000
03/06/2019

Pending

MFRMLS #O5747950

—
11/20/2018

Listed (Active)

MFRMLS #O5747950

$549,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 299 West 4th Avenue

Taxable ValueLand-Additions-Total-
Tax Record2024$10,546 ($879 / month)
Home Facts
Beds3Total Finished SqFt2,410 SqFtAbove Grade Finished SqFt2,410 SqFtStories2Lot Size16,750 SqFtStyleSingle Family ResidenceYear Built1984ZoningSFRCountyORANGEAPN17-23-28-9336-03-200Fireplace TypeHas Fireplace

Schools near 299 West 4th Avenue

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Windermere Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Gotha Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Windermere Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Gotha Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of UPSIDE REAL ESTATE INC, Judy Black; UPSIDE REAL ESTATE INC, Amanda Black PA

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 12/13/2025 06:23 AM