Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
2025 to 2026Years built
4,000 to 4,800 sq ftHome size
4+ bedroomsBedrooms
Historic Town CenterArea
Why people move here

Forty-four custom homesites in the heart of Oakland's Harvest District.

The Grove at Oakland is a 44-homesite enclave in the Harvest District, close to the town center. Four custom builders work here, so no two streetscapes look alike, and the first finished homes run from about 4,000 to 4,800 square feet.
Owners get member access to the Briley Farm clubhouse, pool and courts, and the whole neighborhood sits inside the golf cart district. That means a cart ride to the trail, the farmers market and Speer Park instead of a drive.
Upsizers who want new luxury construction and a walkable small-town address.

Grove at Oakland at a glance

Location: The Harvest District off Oakland Avenue, with the sales office at 2 W Oakland Avenue

Builder: Element, Pioneer, Davila Homes and Justice & Wood

Built: 2025 to 2026 (new construction)

Homes: 44 homesites

Home types: Custom luxury homes

Size: About 4,000 to 4,800 sq ft

Bedrooms: 4+ bedrooms

Area: Historic Town Center

Life here

What Grove at Oakland has

🏊Members access to the Briley Farm clubhouse, pool and courts
⛳Golf cart district
🚲Walk to the West Orange Trail
📶Internet service included in the HOA
✨Custom builder program
Proximity

What is close to Grove at Oakland

  • West Orange Trail walking distance
  • Oakland Town Hall and Speer Park ~0.5 mi
  • Oakland Nature Preserve ~1 mi
  • Historic Downtown Winter Garden ~3 mi

Approximate distances from the community entrance. Walt Disney World is roughly about 25 minutes away off-peak. SR 50 and the Turnpike interchange back up at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Tildenville Elementary

🏫 Lakeview Middle

🏫 West Orange High

🏫 Oakland Avenue Charter School (K to 5, enrollment rules apply)

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

OCPS school locator
The numbers

Grove at Oakland market snapshot

$2,353,078Median sale priceLast 12 months.
Under 1 weekDays on marketMost sales were builder closings entered at closing.
5Closed salesLast 12 months.
100%Sale-to-list price ratioMedian for the last 12 months.

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 15, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Grove at Oakland homes for sale right now

Straight from Stellar MLS. Save the search and get new Grove at Oakland listings the day they hit.

Start of list of properties

Active, 1146 PRADO LANE, , ,press enter for more details, To favorite this property press control+s.
$2.361m
$591
Active
1146 PRADO LANE
Oakland, FL 34787
5
Beds
,
6
Baths
,
3,992
square feet,
Under Construction. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3, 992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floor plan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Heath Stone also features a 2-car detached garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30, 000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Hearth Stone model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.
Residential
MLS# O6359354 Regency Real Estate LLC
More Details
Active, 1106 SARAH MATHEWS DRIVE, , ,press enter for more details, To favorite this property press control+s.
$1.975m
$549
Active
1106 SARAH MATHEWS DRIVE
Oakland, FL 34787
5
Beds
,
6
Baths
,
3,596
square feet,
Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3, 596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.
Residential
MLS# O6375487 Regency Real Estate LLC
More Details
See all Grove at Oakland homes for sale
Free guides

Buying or selling in Grove at Oakland?

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

🏡 Buyer Guide

How buying in Grove at Oakland 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

Grove at Oakland FAQ

Where is Grove at Oakland in Oakland?

Grove at Oakland is in the historic town center along Oakland Avenue and the West Orange Trail, at The Harvest District off Oakland Avenue, with the sales office at 2 W Oakland Avenue.

How far is Grove at Oakland from Walt Disney World?

Roughly about 25 minutes off-peak from this part of Oakland. I will map the exact drive from the entrance before you choose.

When were homes in Grove at Oakland built?

2025 to 2026 (new construction), by Element, Pioneer, Davila Homes and Justice & Wood.

What amenities does Grove at Oakland have?

Members access to the Briley Farm clubhouse, pool and courts, Golf cart district, Walk to the West Orange Trail, Internet service included in the HOA, Custom builder program.

Is Grove at Oakland a gated community?

Grove at Oakland is not listed as gated. Ask me about gated options nearby.

What schools serve Grove at Oakland?

Schools commonly listed for this community: Tildenville Elementary, Lakeview Middle, West Orange High, Oakland Avenue Charter School (K to 5, enrollment rules apply). Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Grove at Oakland in the Town of Oakland?

Grove at Oakland is inside the Town of Oakland, its own incorporated town since 1887 with its own government and police department. Many Oakland homes carry a Winter Garden 34787 mailing address, and a few nearby streets are in Winter Garden city limits or unincorporated Orange County, so I confirm the jurisdiction for every address.

What do homes in Grove at Oakland sell for?

Per Stellar MLS, the median sale price in Grove at Oakland was $2,353,078 across 5 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.

Your next step

Thinking about Grove at Oakland?

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

  • Recent closed sales in Grove at Oakland, straight from Stellar MLS
  • Town of Oakland or Winter Garden, HOA, well and septic 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
More in Historic Town CenterBriley FarmDaniels CoveHistoric Town of OaklandOakland PointeRyan CourtAll Oakland communities
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 Town of Oakland, 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.