AgentLogo

20 E DIVISION STREET

WINTER GARDEN, FL 34787

MLS#: O6413659

$1,149,000

Status: Active
Listing number: O6413659
Listing provided by: CHARLES RUTENBERG REALTY ORLANDO
Listing agent phone: None
Last update: 3 days ago
New on site 4 days ago
Browse Properties
WINTER GARDEN SHORES FIRST ADD - Residential

Property

Beds

4

Full Baths

3

1/2 Baths

None

Year Built

1959

Sq.Footage

2,729

Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!

Features & Amenities

Interior

  • Other Interior Features

    Eat-in Kitchen, Open Floorplan, Sauna, Walk-In Closet(s)

  • Total Bedrooms

    4

  • Bathrooms

    3

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Central

  • Pet friendly

    N/A

Exterior

  • Garage

    Yes

  • Garage spaces

    1

  • Construction Materials

    Concrete

  • Other Exterior Features

    Garden, Private Yard, Rain Gutters

  • Parking

    Attached

  • Pool

    Yes

  • Pool Features

    In Ground, Private

  • Waterfront YN

    NO

Area & Lot

  • Lot Size(acres)

    0.3

  • Lot Size(square feet)

    12982.0

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

Price

  • Sales Price

    $1,149,000

  • Tax Amount

    $7,197

  • Sq. Footage

    2, 729

  • Price/SqFt

    $421

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • New Construction

    NO

  • Foundation Details

    Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    1

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


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

Orange

Elementary School

Middle School

High School

Listing Courtesy of Liz Boyce , CHARLES RUTENBERG REALTY ORLANDO

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 Ashley Baillio

FOUNDER

Ashley Baillio

Call Ashley today to schedule a private showing.

(561) 609-2391

franko+southflorida@init.hr


* 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 one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!

20 E DIVISION STREET

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Sell South Florida via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Related Properties

New on site today
Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Palmetto floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open-concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.
#O6413483

WINTER GARDEN

642 MEDORA WAY

4 Beds

3 Baths

3,109 Sq.Ft.

$1,137,150

MLS#: O6413483

New on site today
Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Cypress floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.
#O6413464

WINTER GARDEN

650 MEDORA WAY

4 Beds

3 Baths

2,902 Sq.Ft.

$1,157,190

MLS#: O6413464

New on site today
Located in the highly sought-after Orchard Hills community and served by top-rated A schools, this Beazer-built home offers nearly 5,000 square feet of thoughtfully designed living space. Features include a dedicated home office, expansive bonus room, media room, fitness space, and flexible living areas designed for the way families live today. An outdoor fireplace and entertaining area extend the living space beyond the walls of the home, while the tile roof and quality finishes add lasting value. Residents enjoy resort-style amenities including a community pool, fitness center and playground. This is the kind of home that adapts to the way families live today.
#O6412376

WINTER GARDEN

5048 PALMETTO PARK DRIVE

5 Beds

3 Baths

4,933 Sq.Ft.

$990,000

MLS#: O6412376

New on site 1 day ago
Welcome to the luxury of 7699 Bowery Dr, located within the highly desirable, master-planned Ravenna community of Horizon West. This exquisite home offers a rare combination of upscale lifestyle flexibility and long-term value. Grand 8-foot double front doors open into a towering, sun-drenched two-story foyer, setting the stage for an expansive, masterfully designed floor plan featuring 5 bedrooms, 4.5 bathrooms, and an office and over 4,000 square feet of high-end living space. INTERIOR HIGHLIGHTS: Designed for both grand entertaining and comfortable everyday living, the main level features a bright, seamless open-concept great room and dining area, complemented by a dedicated private office or study. At the heart of the home is a chef’s gourmet kitchen, fully anchored by 42" Cherry Slate cabinetry with crown molding, elegant quartz countertops, a drop-in cooktop, and a double wall oven. The spacious main-level primary suite serves as a true sanctuary, looking out over the garden and boasting dual walk-in closets alongside a spa-style bath with a frameless, dual-headed luxury shower. SECOND-LEVEL FLEXIBILITY: An oversized staircase leads to a massive second-story loft, a second primary suite, a private movie theater/media room, and two additional bedrooms. The layout is perfectly optimized as a primary residence, multi-generational retreat, or premium long-term asset. Slide open the doors from the upper loft onto a private covered balcony, offering front-row seats to breathtaking sunset water views and nightly theme park fireworks. PEACE OF MIND & CONVENIENCE: This property is thoughtfully upgraded with an energy-efficient solar panel system and a whole-house water filtration system, providing significant savings and exceptional modern utility. Step outside to a beautifully landscaped, oversized 0.45-acre fully fenced backyard with a covered lanai. Residents of Ravenna enjoy a walkability-focused neighborhood with a community pool, playgrounds, low HOA fees, and NO CDD. PRIME LOCATION: Perfectly positioned in Winter Garden, you are zoned for top-rated public schools and sit just minutes from Hamlin Town Center, premium shopping, dining, and major transport corridors including the 429, 408, and Florida’s Turnpike for a swift commute to downtown Orlando. Schedule your private showing today and discover the ultimate Central Florida lifestyle!
#O6415055

WINTER GARDEN

7699 BOWERY DRIVE

5 Beds

4 Baths

4,222 Sq.Ft.

$1,130,000

MLS#: O6415055

New on site 4 days ago
Under Construction. .
#O6414289

WINTER GARDEN

12570 GOLD HONEYSUCKLE STREET

5 Beds

4 Baths

3,636 Sq.Ft.

$962,892

MLS#: O6414289

New on site 4 days ago
Welcome home to this beautifully maintained 4-bedroom, 3 full bath, residence in sought-after Twinwaters. Featuring a designer kitchen with full-extension soft-close drawers and cabinets, 10-foot ceilings on the main level, 9-foot ceilings upstairs, crown molding, and central vacuum, this home offers both comfort and thoughtful upgrades throughout. Enjoy peaceful views of the expansive conservation area from your backyard with no rear neighbors, creating a private and relaxing setting. Professionally designed landscaping provides year-round color and fragrance, while local songbirds add to the natural charm. On clear evenings, catch a glimpse of Disney fireworks from home. Conveniently located just minutes from historic Downtown Winter Garden, shopping, dining, and premier golf destinations including Orange County National. Complete with a spacious 2-car garage, this warm and inviting home is ready for its next owner. Schedule your private showing today!
#O6414027

WINTER GARDEN

1651 AMSEL FALLS PARK TERRACE

4 Beds

3 Baths

3,881 Sq.Ft.

$1,080,000

MLS#: O6414027

New on site 4 days ago
Welcome to what may be the most impeccably maintained and beautifully upgraded home in Oakland Park! This stunning 4-bedroom, 3.5-bath residence showcases designer-inspired finishes throughout, featuring soaring ceilings, modern color palettes, and countless custom enhancements that make it truly one of a kind. Built just four years ago and nestled on a quiet street directly across from green space, this exceptional David Weekley Seaside model offers the perfect blend of elegance, comfort, and convenience. The thoughtfully designed floor plan features a luxurious first-floor owner's retreat complete with a spacious spa-like bath, while the additional bedrooms, study, dining area, and generous living spaces provide room for everyone to spread out and enjoy. No detail has been overlooked. The current owners have invested extensively in premium upgrades, including custom wood trim and accent walls, designer wallpaper, upgraded lighting throughout, custom Zebra window shades, professionally designed closets in the owner's suite, secondary bedroom, and laundry room, plus a water softener, gutters, epoxy-coated garage floors, updated landscaping, and an inviting paver patio. Both the interior and exterior have been freshly painted, creating a truly move-in-ready experience. Step outside to the screened rear porch, where you'll enjoy peaceful mornings, evening breezes, and endless opportunities for birdwatching and outdoor dining. The spacious 3-car garage provides ample storage and functionality for today's lifestyle. Beyond the home itself, Oakland Park offers an award-winning lifestyle unlike any other. This celebrated Parade of Homes community is known for its charming streetscapes, abundant green spaces, waterfront gathering areas, parks, and strong sense of community. Golf-cart-friendly and ideally located just minutes from the West Orange Trail, you'll also enjoy the convenience of walking or riding into vibrant downtown Winter Garden for exceptional dining, shopping, entertainment, and year-round events. This is more than a home—it's a lifestyle defined by luxury, connection, recreation, and the timeless charm of Winter Garden Living.
#O6412381

WINTER GARDEN

1219 SADDLEBACK DRIVE

4 Beds

3 Baths

2,667 Sq.Ft.

$1,050,000

MLS#: O6412381

One or more photo(s) has been virtually staged. Welcome to one of the most beautifully designed homes in the highly sought-after Ovation of Horizon West. A master planned community where luxury, lifestyle, and location come together. Built less than 2 years ago, this exceptional 5-bedroom, 4.5-bath residence offers over 3,600 square feet of thoughtfully designed living space, stunning modern farmhouse finishes throughout, and a premium location! From the moment you step inside, the home delivers an unforgettable WOW factor. Anchored by an oversized island and designer gourmet kitchen with natural gas efficiently for any chef’s delight. Includes premium cabinetry, quartz countertops, and premium fixtures. This open-concept floorplan was made for entertaining and everyday living alike. The expansive great room flows seamlessly to the covered lanai and spacious backyard, perfectly positioned to capture breathtaking sunset views over open farmland and has plenty of room to build your dream pool and no rear neighbors! The stellar floorplan features three ensuite bedrooms, including a luxurious primary suite plus two secondary ensuite spaces, one conveniently located downstairs, making it ideal for guests or multigenerational living. This home also provides loads of storage space, which is a rare find. One of the most magical features of this home? Disney fireworks views from the front porch, den, and upstairs bedroom, giving you front-row seating to the nightly magic. Community amenities include: Pool, Splash Pad, Playground, Hiking & Biking Trails. Perfectly situated in the heart of Horizon West, this home is 4 minutes to Disney property, walking distance to Flamingo Crossings shopping and dining, and brand-new Ovation Elementary School opening August 2026. Convenient access to Hamlin, downtown Winter Garden, MCO, major roadways, shopping, dining, and entertainment make this location truly hard to beat. A rare combination of design, quality, functionality, views, and proximity to Disney. This is Central Florida luxury living at its best!
#O6412120

WINTER GARDEN

15652 GENTLE RAIN DRIVE

5 Beds

4 Baths

3,657 Sq.Ft.

$925,000

MLS#: O6412120

Price reduced
Stunning home 4 bedrooms all suites, located in the Lakeshore community. This beautiful residence offers a perfect blend of modern elegance and comfort. House just has been used from Original owner twice a year since built as a second home, looks brand new! Fully upgraded Kitchen with High end Jen Air appliances, Quartz Waterfall Island countertop, upgraded cabinets and quartz countertops thru out the house.. Extensive custom Carpentry work thru out the house. Deep Lot with plenty of space for a large pool with pre wired and pre plumbing for a future summer kitchen. Residents enjoy resort-style amenities, including clubhouse, fitness center, resort-style pool and proximity to top-rated schools, shopping, and major highways.
#S5151179

WINTER GARDEN

8289 TOPSAIL PLACE

4 Beds

4 Baths

2,755 Sq.Ft.

$920,000

MLS#: S5151179

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Sell South Florida via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

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

I agree to receive communications and understand I can unsubscribe at any time.

I agree to be contacted by Sell South Florida via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service