Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
Mid-2000s, 2010sYears built
1,200 to 1,700 sq ftHome size
Varies by floor planBedrooms
Stoneybrook & East Winter GardenArea
Why people move here

Condos and villas with a resort-style pool and lakeside picnic area.

Tucker Oaks is a condo and villa community off SR 50 and Winter Garden Vineland Road, with about 255 condos and 90 villas built from the mid-2000s into the 2010s. Condos start around 1,200 square feet.
Residents share a resort-style pool and clubhouse, basketball courts, a dog park, a playground and a lakeside picnic and barbecue area. Downtown Winter Garden and SR 50’s shopping are close. It is one of the more affordable ways to own in Winter Garden.
First-time buyers and investors looking for value near downtown.

Tucker Oaks at a glance

Location: Winter Garden Vineland Road and Tucker Oaks Circle

Builder: Custom and individual builders

Built: Mid-2000s, 2010s

Homes: 255 condos

Home types: Condominiums and Townhomes

Size: About 1,200 to 1,700 sq ft

Bedrooms: Varies by floor plan

Area: Stoneybrook & East Winter Garden

Life here

What Tucker Oaks has

🏊Resort-style community pool and clubhouse
🏀Basketball courts
🐕Dog park
🛠Playground
🌊And lakeside picnic and barbecue area
Proximity

What is close to Tucker Oaks

  • Westpoint Commons with Publix Grocery Store ~2 mi
  • Stoneybrook West Village with Publix Grocery Store ~3.5 mi
  • Winter Garden Village ~4 mi
  • Cornerstone at Summerport with Publix Grocery Store ~7.5 mi

Approximate distances from the community entrance. Walt Disney World is roughly 15 to 20 minutes away off-peak. SR 50, the 429 interchanges and Avalon Road back up at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 SunRidge Elementary

🏫 Lakeview Middle

🏫 West Orange High

Orange County Public Schools. Zoning changes, so verify every address.

OCPS school locator
The numbers

Tucker Oaks market snapshot

Homes in Tucker Oaks come in more than one type, and each sells at its own price, so I report them separately. Property type is how the listing agent entered it in Stellar MLS.

$295,500Condos, median sale price8 closed sales, 34 days on market, 98% of list price.
$347,000Townhomes, median sale price5 closed sales, 10 days on market, 96% of list price.

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 16, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Tucker Oaks homes for sale right now

Straight from Stellar MLS. Save the search and get new Tucker Oaks listings the day they hit.

Start of list of properties

Active Under Contract, 1424 SCARLET OAK LOOP, , ,press enter for more details, To favorite this property press control+s.
$379,000
$218
Active Under Contract
1424 SCARLET OAK LOOP
Winter Garden, FL 34787
3
Beds
,
3
Baths
,
1,737
square feet,
Under contract-accepting backup offers. Welcome to your beautifully updated home in the gated community of Winter Garden. This charming residence offers 3 bedrooms, 2.5 baths, 2-car garage, and approximately 1, 737 sq. ft. of comfortable living space. In 2025, this home underwent a $53K renovation, featuring a modern kitchen with 42” shaker white cabinets with undermount lighting and quartz counters, stainless steel appliances, and a double oven for added convenience. The renovation also includes kitchen and bathroom upgrades, frameless shower doors, LVP flooring on the upstairs level and stairs, interior and exterior paint, new drapes, and elevated finishes throughout. Additional details include crown molding and 5” baseboards. Enjoy peace of mind with an A/C unit (3 years old) and a new roof (2025). Relax or entertain on the screen-covered patio with pond views. The garage floors feature non-slip coating, and the home includes all-new light fixtures, ceiling fans, and updated lighting. Additional benefits include a security system for added safety and convenience. Community amenities include a pool, playground, dog park, basketball courts, BBQ grills, and walking trails, perfect for everyday enjoyment. Located near Downtown Plant St, Fowler’s Grove, and with convenient access to 429 and the Florida Turnpike, you’re close to dining, shopping, entertainment, and major travel routes. Schedule your showing today!
Residential
MLS# O6436325 Teamconnect Realty LLC
More Details
Active, 15625 BOGGY OAK CIRCLE, , ,press enter for more details, To favorite this property press control+s.
$335,000
$236
Active
15625 BOGGY OAK CIRCLE
Winter Garden, FL 34787
3
Beds
,
3
Baths
,
1,419
square feet,
SELLER MOTIVATED! OFFERING CONCESSIONS TOWARDS FLOORING. Beautifully maintained 3-bedroom, 2.5-bath townhome located in the gated Tucker Oaks community in Winter Garden. This home features an open-concept floor plan with abundant natural light, a functional layout, and an attached garage for added convenience. The kitchen offers ample cabinet and counter space and overlooks the living and dining areas. Upstairs, the primary suite includes a private bath and walk-in closet, while the additional bedrooms provide flexibility for guests, work-from-home space, or other uses. Recent updates include a new roof, dishwasher, and garbage disposal installed in August 2024, along with an HVAC system replaced in 2022. Community amenities include a pool, playground, basketball courts, scenic areas, and dog parks — including one conveniently located on the same cul-de-sac as the condo. Conveniently located near Downtown Winter Garden, Winter Garden Village, SR-429, Florida’s Turnpike, shopping, dining, hospitals, and area attractions. This property offers low-maintenance living with convenient access to major commuter routes and Central Florida destinations.
Residential
MLS# G5112579 Scates Realty & Investment Pro
More Details
Active Under Contract, 15357 OAK APPLE COURT, , ,press enter for more details, To favorite this property press control+s.
$300,000
$177
Active Under Contract
15357 OAK APPLE COURT
Winter Garden, FL 34787
3
Beds
,
3
Baths
,
1,699
square feet,
Under contract-accepting backup offers. Seller motivated, under appraised value, and back on the market. This Winter Garden Corner unit is located in the gated community of Tucker Oaks in sought-after Winter Garden. This beautifully upgraded condo-townhome style offers a bright open-concept layout along with 3 bedrooms and 2.5 bathrooms. This home offers the perfect blend of modern upgrades and serene privacy. As one of the few units backing directly onto a lush conservation lot, you’ll enjoy peaceful, wooded views and extra natural light that only a corner position can provide. Relax on your back patio with no rear neighbors and a private forest backdrop. The community offers a pool, walking paths, basketball courts, BBQ area, playground, not to mention, minutes from the West Orange Trail and downtown Winter Garden’s charm. You deserve this home.
Residential
MLS# O6401625 The Simon Simaan Group
More Details
Active, 15613 BOGGY OAK CIRCLE, , ,press enter for more details, To favorite this property press control+s.
$299,900
$247
Active
15613 BOGGY OAK CIRCLE
Winter Garden, FL 34787
2
Beds
,
2
Baths
,
1,216
square feet,
MAINTENANCE-FREE LIVING IN DESIRABLE TUCKER OAKS! Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo with an attached single car garage, ideally located in the sought-after Tucker Oaks community. Situated on a quiet, lightly traveled cul-de-sac-style road with a dog parkconveniently located directly across the street, this home offers comfort, convenience, and an easy Florida lifestyle.This is one of the newer-built models in the community and features an expanded kitchen layout with additional counter space and a convenient eat-in area. The kitchen is equipped with stainless steel appliances, including a French-door refrigerator, dishwasher, microwave, and range, alongwith upgraded counters, sink, and faucet. The appliances are approximately four years old. Additional kitchen conveniences include pull-out/roll-out cabinet shelving and upper and lower cabinet lighting.The spacious family room features a beautiful focal wall with a floating shelf, electric fireplace, and wall-mounted flat-screen TV, creating a warm and inviting space to relax or entertain. Step outside to the larger upper-level balcony, the perfect spot to enjoy your morning coffee or unwind at the end of the day.The second bathroom features a walk-in shower for added convenience. An interior laundry room includes installed shelving for additional storage.The attached garage offers storage shelving, a painted and sealed floor, and convenient attic storage for seasonal items and belongings.Tucker Oaks offers an array of amenities, including a community pool, basketball courts, playground, dog park, and picnic/BBQ area. Enjoy an unbeatable location close to Winter Garden Village, restaurants, shopping, the farmers market, and Central Florida’s world-famous attractions. Witheasy access to the Florida Turnpike, SR 429, SR 408, and Highway 50, getting around Central Florida is quick and convenient.Come enjoy low-maintenance living, wonderful community amenities, and an incredible location—all in one great condo!
Residential
MLS# O6450253 Coledev Real Estate LLC
More Details
See all Tucker Oaks homes for sale
Free guides

Buying or selling in Tucker Oaks?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Tucker Oaks works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Tucker Oaks FAQ

Where is Tucker Oaks in Winter Garden?

Tucker Oaks is in east Winter Garden near Stoneybrook West, Daniels Road and Tilden Road, at Winter Garden Vineland Road and Tucker Oaks Circle.

How far is Tucker Oaks from Walt Disney World?

Roughly 15 to 20 minutes off-peak from this part of Winter Garden. I will map the exact drive from the entrance before you choose.

When were homes in Tucker Oaks built?

Mid-2000s, 2010s. Most homes were built by individual or custom builders.

What amenities does Tucker Oaks have?

Resort-style community pool and clubhouse, Basketball courts, Dog park, Playground, And lakeside picnic and barbecue area.

Is Tucker Oaks a gated community?

Tucker Oaks is not listed as gated. Ask me about gated options nearby.

What schools serve Tucker Oaks?

Schools commonly listed for this community: SunRidge Elementary, Lakeview Middle, West Orange High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Tucker Oaks inside Winter Garden city limits?

Many homes with a Winter Garden 34787 address, including much of Horizon West, sit in unincorporated Orange County rather than the City of Winter Garden. Taxes, utilities and services differ, so I confirm the jurisdiction for every address.

What do homes in Tucker Oaks sell for?

It depends on the type of home. Per Stellar MLS, for the 12 months ending September 30, 2026, Tucker Oaks condos sold at a $295,500 median across 8 sales, and townhomes sold at a $347,000 median across 5 sales. Call or text me at 407.502.4719 for recent sales that match your home.

Your next step

Thinking about Tucker Oaks?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Tucker Oaks, straight from Stellar MLS
  • City or county, HOA and CDD for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719
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Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify city or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.