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$499,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,724 Sq. Ft.
  • Updated 9 days ago
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Welcome to this completely reimagined 4 bedroom, 2 bath, single story home in Maitland's English Estates. 1220 Winston Road features a completely open kitchen with beautiful granite counter tops, 42" cabinets, marble backsplash, newer kitchen appliances, and a breakfast bar. From here you have views to the living room and the gorgeous custom accent wall with built-in lighting. Two generous sized bedrooms to the right share a jack-n-jill bathroom, and have fantastic storage and natural light. The master bedroom is a suite of its own and hosts TWO walk-in closets and an oversized primary bathroom with dual sinks. The 4th bedroom is across the primary bedroom and would make a great den, office, nursery, or guest room. Just off the kitchen, you'll find an adorable mudroom with newer washer and dryer, pantry storage, and a built-in wooden bench-because real life deserves smart design. Outside, the fully fenced backyard provides plenty of room to relax or entertain, while a separate paved parking pad offers space for an additional vehicle, boat, or future shed. English Estates is known for its strong sense of community and low turnover, with an optional HOA that hosts neighborhood events like the annual fall festival. The location is hard to beat: quick access to 436, 17-92, Red Bug Lake Road, and the I-4 Express Lanes via the Maitland Boulevard exit makes commuting to Downtown Orlando smooth, even during rush hour. Bottom line: this is one of those homes that checks the boxes and feels good the moment you walk in.

Full Property Details for 1220 Winston Rd

General

  • Price: $499,000
  • Taxes: $5,647 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6369769
  • Updated: 1/7/2026
  • Added to Site: 16 day(s) ago

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 3
  • Interior Features: Eating Space In Kitchen, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor
  • Appliances: Convection Oven, Dishwasher, Dryer, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Laminate, Terrazzo

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Exterior

  • Exterior Features: Lighting, Private Yard, Sliding Doors
  • Deck/Patio: Rear Porch, Screened
  • Porch/Patio/Deck: Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway

Location

  • Area: 32751 - Maitland / Eatonville
  • County: Seminole
  • Development Name: 32751 - Maitland / Eatonville
  • Subdivision: ENGLISH ESTATES UNIT 2
  • Driving Directions: From Derbyshire turn onto Winston Road. Home is located on the right side.
  • Direction Faces: West

School Information

  • Elementary School: English Estates Elementary
  • Middle School: South Seminole Middle
  • High School: Lake Howell High

Community

  • Community Name: 32751 - Maitland / Eatonville
  • Pet Restrictions: Check with community and city guidelines

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Available

Structural Information

  • Architectural Info: Colonial, Contemporary
  • Architectural Style: Colonial, Contemporary
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,724
  • Sq. Ft. Source: Public Records
  • Year Built: 1964

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.26
  • Lot Size (Sq. Ft.): 11,200
  • Lot Size: 11200
  • Street/Road Desc.: Paved
  • Fencing (Description): Chain Link

Financial Considerations

  • Tax Amount: $5,647.67
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 10 BLK M ENGLISH ESTATES UNIT 2 PB 13 PG 85
  • Flood Zone Info: X
  • APN: 2021305030M000100
  • Property ID: 2021305030M000100
  • Block/Lot/Section: M

Listed by Re/Max Town & Country Realty

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Listing agent

— 1220 Winston Rd —

  • Re/Max Town & Country Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1220 Winston Rd

School District:Seminole County School District
NameGradesDistance
English Estates Elementary School
299 Oxford Road, Fern Park, FL 32730
K-50.7 mi
Seminole Academy Of Digital Learning
450 Technology Park, Lake Mary, FL 32746
6-86.8 mi
Lake Howell High School
4200 Dike Road, Winter Park, FL 32792
9-123.7 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1220 Winston Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/01/2026
Listed
$499,000
—
MLS
2/29/2024
Sold
$499,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1220 Winston Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,263
-7%
$386,442
-4%
2024
$5,648
260%
$402,201
203%
2023
$1,569
3%
$132,633
3%
2022
$1,523
5%
$128,770
3%
2021
$1,450
—
$125,019
1%
2021
$1,450
5%
$123,293
4%
2018
$1,386
1%
$118,274
2%
2017
$1,375
-2%
$115,841
2%
2016
$1,401
-1%
$113,458
1%
2015
$1,411
—
$112,669
-7%
2019
$1,409
1%
$120,521
8%
2014
$1,392
-1%
$111,775
2%
2013
$1,406
—
$110,123
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 1220 Winston Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Re/Max Town & Country Realty

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1220 Winston Road, Maitland, FL 32751 (MLS# O6369769) is a Single Family property with 4 bedrooms and 2 full bathrooms. 1220 Winston Road is currently listed for $499,000 and was received on January 01, 2026. Want to learn more about 1220 Winston Road? Do you have questions about finding other Single Family real estate for sale in Maitland? You can browse all Maitland real estate or contact a Coldwell Banker agent to request more information.

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