Niles Harrison Pfeiffer

Niles Harrison Pfeiffer Central Florida REALTOR®

$1,450,000.00
101 STARR STREET, OAKLAND, FL - 34760
3 beds
3.5 baths
2,502 sqft
$1,450,000.00
101 STARR STREET, OAKLAND, FL - 34760
Niles Harrison Pfeiffer
$1,450,000.00
3 beds
3.5 baths
2,502 sqft
101 STARR STREET, OAKLAND, FL - 34760
For Sale
Photo 1
  • Built in 2020
  • 3 garage spaces
  • $579.54/sqft
  • Lot size: 17,146 sqft
  • 183 days on market

Seller is offering First Mortgage Owner Financing up to $750,000 at 4.3% interest rate with a 3-year Balloon structure, to be organized by a real estate attorney. Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly. Set beneath a canopy of majestic, centuries-old oaks, this meticulously designed home offers a rare combination of elegance, comfort, and accessibility. With a spacious open floor plan, soaring 14-foot ceilings, and oversized 8-foot doors throughout, the home is both grand in scale and thoughtfully functional. Fully handicap accessible and designed with mobility in mind, it offers seamless, barrier-free living that accommodates all stages of life. At the heart of the home lies a gourmet kitchen, professionally designed by a chef and custom builder. This culinary centerpiece features top-of-the-line appliances, generous prep space, and luxury finishes—perfect for everything from everyday meals to large-scale entertaining. The open-concept design continues into expansive living and dining areas that flow effortlessly into the outdoors, creating an ideal environment for both intimate gatherings and lively celebrations. Step outside to your own private oasis: a beautifully screened-in pool, complemented by a fully equipped summer kitchen and ample patio space for lounging or dining under the stars. Whether you’re enjoying a quiet morning coffee poolside or hosting a weekend cookout, the outdoor living area is designed to elevate your lifestyle year-round. Located just steps from the Oakland Farmers Market, Charter School, Heritage Center, and Post Office, this home is at the center of a walkable, welcoming community where neighbors know one another and nature thrives. With direct golf cart access to vibrant Downtown Winter Garden, you’re only minutes from award-winning restaurants, unique shops, live entertainment, and a bustling weekly farmers market. Outdoor enthusiasts will love the nearby West Orange Trail and Lake Apopka’s scenic shoreline, perfect for biking, walking, birdwatching, or kayaking. And when adventure calls, you’re a short drive from some of the world’s most celebrated destinations, including Walt Disney World, Universal Studios, and Downtown Orlando. Combining small-town charm with big-city convenience, this location is truly second to none. More than just a residence, 101 N Starr Street is a destination for those seeking refined, accessible living in one of Central Florida’s most desirable communities. With its custom design, premium features, and unbeatable location, this home offers a lifestyle of beauty, comfort, and lasting value.

  • Directions: Traveling on the Turnpike: take exit 272 onto SR-50 toward Winter Garden. 0.9 miles, turn Left onto S Tubb St. 0.3 miles, turn Right onto E Oakland Ave. 0.2 miles, turn Left onto N Starr St. 500 ft, destination on your Left. Traveling on Highway 50 Westbound: turn Right onto S Starr St. (Turn at Tractor Supply). 0.4 miles, destination on your Left.
  • County: Orange
  • Geo subdivision: OAKLAND TOWN

Nearby Schools

Tildenville Elem

Lakeview Middle

West Orange High

Features

Financial

Let's get in touch!

Niles Harrison Pfeiffer

Niles Harrison Pfeiffer

Central Florida REALTOR®

See also

For Sale
16115 JOHNS LAKE OVERLOOK DRIVE, WINTER GARDEN, FL - 34787
$1,420,000.00
5 bds
4.5 ba
4,965 sqft
16115 JOHNS LAKE OVERLOOK DRIVE, WINTER GARDEN, FL - 34787
For Sale
16650 BOLSENA DRIVE, MONTVERDE, FL - 34756
$1,591,995.00
4 bds
4.5 ba
3,878 sqft
16650 BOLSENA DRIVE, MONTVERDE, FL - 34756
For Sale
16669 VARONE COVE COURT, WINTER GARDEN, FL - 34787
$1,450,000.00
7 bds
5 ba
5,613 sqft
16669 VARONE COVE COURT, WINTER GARDEN, FL - 34787
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6323162
Listing updated: January 18, 2026 at 8:29PM
Listing provided by: Andrew Kincaid, BHHS FLORIDA REALTY
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