Sarasota's Premier Homes

Mid-Century Modern, Ranch

1434 WINSTON ROAD

MAITLAND , FL 32751

MLS#: O6337790

$579,000

Status: Active
Listing number: O6337790
Listing provided by: COMPASS FLORIDA LLC
Listing agent phone: None
Last update: 3 days ago
On site: 5 days ago
Browse Properties
ENGLISH ESTATES UNIT 3 - Residential

Property

Beds

4

Full Baths

2

1/2 Baths

None

Year Built

1971

Sq.Footage

2,312

Welcome to 1434 Winston Road, located in Seminole County’s desirable English Estates neighborhood. This beautifully maintained midcentury modern–inspired 4-bedroom, 2-bathroom pool home offers 2,312 square feet of bright and functional living space, filled with natural light and thoughtful updates throughout. Step inside to discover a warm, inviting layout with bamboo wood and tile flooring in all the main living areas and freshly painted interiors that create a crisp, modern feel. The kitchen features a peninsula with seamless flow to the dining and living rooms, along with an updated backsplash that highlights the home’s timeless design and provides a perfect gathering spot for family and friends. The primary suite features a spacious bathroom with a new vanity, walk in shower and a dreamy walk-in closet with plenty of natural light. A generously sized Florida room overlooks the pool area and has been recently equipped with a new split AC system—perfect for lounging, working out, or working from home all year long. Recent upgrades include a roof (2022), new HVAC system (2025), and full repiping with an updated electrical panel (2022). Additional improvements include hurricane-rated smart garage doors and openers (2023), dual-pane windows for energy efficiency, and a new pool pump and filter tank (2024). The backyard is fully fenced and showcases lush, mature landscaping, creating a private and serene outdoor escape. Exterior maintenance is a breeze with recently installed gutters and a new front yard smart irrigation system. Bonus—this home sits on a conservation lot! No rear neighbors!! With its midcentury charm, modern updates, and major systems already in place, this move-in-ready home is the perfect blend of style and function. Just minutes from parks such as Kewannee, shopping, and top-rated schools, it offers the best of Maitland and Seminole County living. <iframe src="https://www.zillow.com/view-imx/ca9004b4-036a-46c6-adbf-3df42117962d?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard" width="100%" height="790px" frameBorder="0" style="border: 0;"></iframe><br>Brought to you by <a href="" target="_blank">The A List</a>

Features & Amenities

Interior

  • Other Interior Features

    High Ceilings, Stone Counters, Vaulted Ceiling(s)

  • Total Bedrooms

    4

  • Bathrooms

    2

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    NO

  • Heating YN

    YES

  • Heating

    Central

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Block, Stucco

  • Other Exterior Features

    Rain Gutters

  • Parking

    Attached

  • Patio and Porch Features

    Covered, Enclosed, Rear Porch, Screened

  • Pool

    Yes

  • Pool Features

    In Ground, Screen Enclosure, Private

  • Waterfront YN

    NO

  • View

    Trees/Woods

Area & Lot

  • Lot Features

    Greenbelt

  • Lot Size(acres)

    0.26

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Mid-Century Modern, Ranch

Price

  • Sales Price

    $579,000

  • Tax Amount

    5962.7

  • Sq. Footage

    2, 312

  • Price/SqFt

    $250

HOA

  • Association

    NO

School District

  • Elementary School

    English Estates Elementary

  • Middle School

    South Seminole Middle

  • High School

    Lake Howell High

Property Features

  • Stories

    1

  • Foundation Details

    Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Septic Tank

  • Tax Lot

    9

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

Seminole

Elementary School

English Estates Elementary

Middle School

South Seminole Middle

High School

Lake Howell High

Listing Courtesy of Abby Greenberg , COMPASS FLORIDA LLC

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent MichaelGraf

Business Coach | Executive Sales Associate | Realtor®

MichaelGraf

Call Michael today to schedule a private showing.

(941) 315-6980

michael@thegrafgroupvip.com


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
Welcome to 1434 Winston Road, located in Seminole County’s desirable English Estates neighborhood. This beautifully maintained midcentury modern–inspired 4-bedroom, 2-bathroom pool home offers 2,312 square feet of bright and functional living space, filled with natural light and thoughtful updates throughout. Step inside to discover a warm, inviting layout with bamboo wood and tile flooring in all the main living areas and freshly painted interiors that create a crisp, modern feel. The kitchen features a peninsula with seamless flow to the dining and living rooms, along with an updated backsplash that highlights the home’s timeless design and provides a perfect gathering spot for family and friends. The primary suite features a spacious bathroom with a new vanity, walk in shower and a dreamy walk-in closet with plenty of natural light. A generously sized Florida room overlooks the pool area and has been recently equipped with a new split AC system—perfect for lounging, working out, or working from home all year long. Recent upgrades include a roof (2022), new HVAC system (2025), and full repiping with an updated electrical panel (2022). Additional improvements include hurricane-rated smart garage doors and openers (2023), dual-pane windows for energy efficiency, and a new pool pump and filter tank (2024). The backyard is fully fenced and showcases lush, mature landscaping, creating a private and serene outdoor escape. Exterior maintenance is a breeze with recently installed gutters and a new front yard smart irrigation system. Bonus—this home sits on a conservation lot! No rear neighbors!! With its midcentury charm, modern updates, and major systems already in place, this move-in-ready home is the perfect blend of style and function. Just minutes from parks such as Kewannee, shopping, and top-rated schools, it offers the best of Maitland and Seminole County living. <iframe src="https://www.zillow.com/view-imx/ca9004b4-036a-46c6-adbf-3df42117962d?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard" width="100%" height="790px" frameBorder="0" style="border: 0;"></iframe><br>Brought to you by <a href="" target="_blank">The A List</a>

1434 WINSTON ROAD

Message successfully sent.

What would you like to know?

Related Properties

New on site 2 days ago
Lovely direct waterfront condominium with large screen porch overlooking beautiful 451 acre Lake Maitland. Screened terrace is wonderful for enjoying the lake. Share the same view as multimillion dollar homes. Updated floor plan with open kitchen, tile throughout, French doors. Maitland is a very central community of greater Orlando. Close to many great restaurants along Orlando Avenue and Winter Park. Great place to walk, bike, kayak, paddleboard. This is a great place to live!
#TB8420863

MAITLAND

1140 S ORLANDO AVENUE 16

2 Beds

1 Baths

816 Sq.Ft.

$498,000

MLS#: TB8420863

New on site 3 days ago
Welcome to 1411 Glastonberry Road, a spacious 5-bedroom, 2-bathroom home tucked within the desirable English Estates community in Maitland. This established neighborhood is known for its tree-lined streets, sense of community, and highly sought-after location within the top-rated Seminole County Public School System, making it an excellent choice for those looking for both comfort and convenience. Step inside and you will find a thoughtfully designed split floorplan that maximizes space and privacy. The home has been updated with laminate flooring throughout, providing a modern look that is both stylish and low-maintenance. The bathrooms have been tastefully renovated, giving a fresh and contemporary feel that complements the home’s overall design. Essential updates have already been taken care of for you, a durable metal roof provides peace of mind for years to come, a complete re-plumb in 2021. One of the most notable features is that the home has been converted to public sewer! The heart of the home features open living and dining areas that flow seamlessly, creating the perfect setting for both everyday living and entertaining. With five bedrooms, there is ample flexibility for a growing household, guests, or even creating a home office or hobby room to suit your lifestyle needs. Outdoors, the home continues to impress with a spacious fenced backyard that offers plenty of room to play, garden, or simply relax in privacy. Enjoy evenings on the covered patio, or step out to the additional brick paver patio, an ideal spot for hosting barbecues, gatherings, or simply soaking up Florida sunshine. Location is key, and this property delivers. You are just a short 10–15 minute drive to Park Avenue in Winter Park, where you can enjoy upscale dining, boutique shopping, and cultural attractions. Easy access to major roadways ensures quick commutes to Downtown Orlando, the Maitland Business District, and surrounding areas, making this home as practical as it is inviting.
#O6337857

MAITLAND

1411 GLASTONBERRY ROAD

5 Beds

2 Baths

2,966 Sq.Ft.

$535,000

MLS#: O6337857

New on site 4 days ago
One or more photo(s) has been virtually staged. Located in the heart of Maitland on a quiet cul-de-sac, this 3 bedroom, 2 bath single-story ranch home is a hidden gem. Light and bright with clean lines, this charming, renovated home is in move-in condition. The functional kitchen features stainless steel appliances, tile backsplash, ample cabinetry, a breakfast bar and an adjoining dining area overlooking the living room. With a wall of windows, the spacious living area is the heart of the home. The primary suite includes a walk-in closet, while the ensuite bath showcases a tiled shower updated vanity, lighting and fixtures. Two secondary bedrooms overlook the front yard and share a hall bath with dual sinks and a tub/shower combo. Outdoor living is a delight with an open-air covered patio, built-in grill, and a fenced back yard accented with flowering foliage. There is plenty of room to add a pool. Additional highlights include a long driveway with ample parking, a shed, a storage room off the patio and a whole-home water purification system. Conveniently located near I-4, Winter Park, SunRail, Maitland Farmer's Market and local area restaurants. Recent improvements include a dishwasher in 2025, 3-ton AC in 2022 and windows in 2020. This property combines charm, function and location in one exceptional package. Welcome home!
#O6338131

MAITLAND

170 E FAITH TERRACE

3 Beds

2 Baths

2,667 Sq.Ft.

$525,000

MLS#: O6338131

Prepare to be captivated by this fully renovated gem located in the highly sought after English Estates neighborhood. Offering 1,798 square feet of meticulously designed living space, this three bedroom, two bathroom home blends timeless charm with modern luxury. Every inch has been thoughtfully updated, including a brand new air conditioning system, new thermostat, and a newer roof. The home features an open layout with custom details such as designer sconces, a fluted accent wall, and an abundance of natural light throughout. The spacious primary suite includes a spa inspired bathroom designed to feel like a private retreat. Step outside to a fully fenced backyard oasis complete with a sparkling pool and outdoor shower, perfect for entertaining or relaxing in total privacy. Located in a no flood zone, this property offers peace of mind and lifestyle convenience. Just minutes from I-4, the Altamonte Mall, and a short walk or bike ride to the scenic Kawannee Trail, this location provides easy access to everything Orlando has to offer. This is a rare opportunity to own a stunning home in a well established neighborhood. Schedule your private showing today.
#TB8414987

MAITLAND

1231 SIDCUP ROAD

3 Beds

2 Baths

2,498 Sq.Ft.

$575,000

MLS#: TB8414987

Welcome to this generously sized home offering a rare opportunity to create the space you’ve always dreamed of. Situated in a desirable Maitland neighborhood, this property features 3 bedrooms, 2 bathrooms, a 2-car garage, and a private pool — all on a fully fenced lot with NO HOA. Inside, you’ll find a traditional layout with a formal living and dining room, a cozy family room, and an oversized bonus room perfect for a home office, game room, or guest space. The guest bathroom has already been beautifully updated, and the windows have been replaced for added efficiency and comfort. While the home does need updating — the solid bones, spacious layout, and prime location make this a great opportunity for buyers with vision. Whether you're looking to renovate and make it your own or invest in a property with strong potential, this Maitland pool home is a must-see.
#O6333203

MAITLAND

637 MAGNOLIA DRIVE

3 Beds

2 Baths

2,370 Sq.Ft.

$479,000

MLS#: O6333203

One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 2-bathroom pool home nestled in the heart of Maitland, within sought-after Seminole County. Offering over 1,600 square feet of bright and open living space, this home is designed for comfort and functionality. The sun-filled floor plan features an inviting layout with large windows that bathe the interior in natural light throughout the day. The kitchen is open and functional, seamlessly flowing into the dining and living areas—ideal for entertaining or simply enjoying everyday life. With ample cabinetry and sleek stainless steel appliances, it’s both stylish and practical for modern living. Each of the four bedrooms offers comfort, flexibility, and generous space. The primary suite is a private retreat, complete with its own spa-like bathroom featuring dual vanities, a soaking tub, and a walk-in shower. The remaining three bedrooms are equally spacious and well-lit, perfect for guest accommodations, children’s rooms, or home offices—offering a layout that easily adapts to your lifestyle needs. Step outside to your own private oasis, where a sparkling pool and expansive backyard provide the perfect setting for relaxing weekends, gatherings, or outdoor fun. Located just minutes from top-rated schools, parks, shopping, and dining, this home blends comfort, convenience, and Florida charm. Don’t miss this opportunity to make it yours!
#O6332033

MAITLAND

736 FOREST GLEN COURT

4 Beds

2 Baths

2,175 Sq.Ft.

$499,999

MLS#: O6332033

This residence exemplifies pride of ownership, boasting a beautifully appointed kitchen with high-quality, updated cabinetry and granite countertops, complemented by upper-end stainless steel appliances. Upon arrival, the exceptional workmanship evident in the pavers driveway is immediately apparent, and this attention to detail extends to the nicely landscaped backyard, complete with a paver patio. The roof was installed in September 2020. Prospective buyers may be interested in assuming the seller's 2.76% interest rate. Please note that the sellers are currently in the process of vacating the property, a few large items remain.
#V4944096

MAITLAND

356 CROTON DRIVE

4 Beds

2 Baths

2,964 Sq.Ft.

$535,000

MLS#: V4944096

You know it is your house as you walk on your cobblestone to your front porch. As you enter the wide double doors they beckon you inside. This is your Ruttenberg floor plan home which is designed for both comfort and style. Heart of the Home: The Kitchen At the center of the home, the kitchen has been thoughtfully updated with solid wood cabinets, a functional working island, ample drawer space, and a spacious pantry. The cozy eat-in nook overlooks your cobblestone-surrounded, screened-in pool, creating a perfect spot for morning coffee or casual meals. Living Spaces The family room opens easily, featuring a charming brick fireplace with an electric crackle for ambiance. Three additional bedrooms are thoughtfully arranged, including a pool-planned bathroom and a secondary ensuite bath for guests or family. Formal Living & Dining An L-shaped formal living and dining room divides the home, offering elegant spaces for entertaining or relaxing. Primary Suite Retreat The updated primary suite is a true retreat, featuring a private water closet, step-in shower, double sinks, and double closets. Wide doors throughout make movement easy and accessible. Convenience & Extras Laundry facilities are conveniently located on the way to the two-car garage, where you’ll also find a carbonated water filter just outside the door for fresh, sparkling water. Outdoor Living For those who love the outdoors, the large cobblestone deck wraps around the screened-in pool, providing plenty of space for entertaining year-round. There’s a fire pit in the backyard to enjoy.
#O6330873

MAITLAND

2318 CASTLEWOOD ROAD

4 Beds

3 Baths

3,381 Sq.Ft.

$595,000

MLS#: O6330873

One or more photo(s) has been virtually staged. Welcome to 2632 Derbyshire Road in the Charming Indian Hills Neighborhood of Maitland, FL! This is your opportunity to move into the highly desirable and established Indian Hills community—where comfort, style, and location come together effortlessly. This beautifully updated 4-bedroom, 2-bath home is situated on a spacious corner lot just over a quarter-acre, offering both privacy and room to spread out. Step inside to discover a thoughtfully designed split floor plan, with three bedrooms on one side and a private primary suite on the other, creating an ideal layout for families or guests. The primary bedroom features direct access to the pool and an en-suite bathroom, complete with a modern barn door entry for added charm and functionality. This home offers multiple living areas, including a formal living room, a cozy family room, and a formal dining area—plenty of space for both everyday living and entertaining. The fully updated kitchen shines with new cabinets, butcher block countertops, a chef’s sink, and brand-new stainless steel appliances. Both bathrooms have been fully renovated and include granite countertops and updated fixtures. Enjoy Florida living at its finest in your screened-in pool and private fenced backyard—perfect for relaxing weekends, family gatherings or your fur babies. The pool area is very spacious and screened, offering ample room for patio furniture so you can lounge and unwind in your own personal private oasis retreat. A spacious laundry room adds even more convenience, complete with a bonus laundry sink to make everyday cleaning tasks easier and more efficient. The home has been freshly painted inside and out and features important recent upgrades: a new roof (2023), new A/C unit (2022), and replumbing completed approximately 10 years ago. Conveniently located near SR 436, 17/92, and just minutes from Altamonte Mall, AdventHealth Hospital, and a variety of local shops and restaurants. You're also less than 15 minutes from the vibrant dining, shopping, and cultural attractions of downtown Winter Park, making this location ideal for both convenience and lifestyle. Plus, this home is zoned for Seminole County’s top-rated public schools, making it perfect for families seeking excellent education options. And don’t forget—NO HOA! Whether you're looking for space, style, or a family-friendly location, 2632 Derbyshire Road is the total package. Come discover this tranquil, well-established neighborhood and make this home yours! Schedule your showing today!
#O6331860

MAITLAND

2632 DERBYSHIRE ROAD

4 Beds

2 Baths

2,452 Sq.Ft.

$575,000

MLS#: O6331860

- property

Send a message

Message successfully sent.

Your message

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to receive some additional information on this specific property or similar properties?

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here