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105 PINE STREET, Windermere, FL 34786 (Sold on )

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 $2,500,000

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  • 5 BedBeds
  • 6 BathBaths
  • 5,696 SqFtSqFt
  • TypeResidential
  • Active
  • MLS# O6405163

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Property Description

Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques, and the weekly farmers market. Built in 2015 and thoughtfully expanded, this 5,696 square foot home features five bedrooms and five and a half bathrooms, including a fully separate casita ideal for in-law living, guests, or private quarters. From the moment you arrive, fresh landscaping and an exposed brick front porch create a warm and inviting entrance. Inside, the open living space is both spacious and comfortable, with high ceilings, wood beams, crown molding, and a gas fireplace, complemented by shiplap and exposed brick accents. The kitchen opens seamlessly to the main living area and overlooks the backyard, featuring a large Cambria quartz island, Kohler farm sink, walk-in pantry, Bosch double ovens, Viking gas cooktop, custom hood, LG refrigerator, soft-close cabinetry, under-cabinet lighting, and a dedicated coffee bar. The primary suite offers peaceful backyard views, two custom walk-in closets, and a well-appointed bath with dual vanities, a makeup station, a garden tub, and a large walk-in shower with floor-to-ceiling tile and dual showerheads. Additional bedrooms are thoughtfully placed, including one with an ensuite bath. A versatile flex room with a coffered ceiling, storage, and its own laundry setup connects to a private office with built-ins and a walk-in closet. A secondary primary suite provides a comfortable space for extended family or guests. In total, the home offers three separate laundry areas for added convenience. Outdoor living is designed for true Florida living. Two sets of sliding glass doors, including one from the flex room, open to a covered lanai with wood plank ceiling and fans, along with a fully equipped summer kitchen featuring an Artisan natural gas grill, vent hood, sink, and icemaker. The space extends to an expansive paver patio surrounding a heated saltwater pool and spa with water features, all overlooking a large fenced backyard. The casita, completed in 2023 and offering over 1,200 square feet, lives like a private residence with its own entrance and Spanish Mediterranean character, including wood beams, hardwood flooring, and a Kiva-style fireplace. It features a full living room, a kitchen with GE Café appliances and a quartz island, and a spacious bedroom suite with a custom walk-in closet and a beautifully finished bath. A screened lanai and separate fenced yard provide added privacy. A three-car garage with high ceilings includes an oversized RV-height door, 50-amp plug, and space for additional storage or lifts, along with a third laundry area. Additional features include dual AC systems, tankless water heaters, and a Generac generator. Residents of Windermere enjoy private access to the Butler Chain of Lakes, parks, tennis courts, and a boat ramp, all golf cart accessible. Golf cart friendly with tree-lined streets and a true small-town feel. No HOA and conveniently located near top-rated schools, major roadways, and world-class dining and entertainment. This is a truly unique Windermere home designed for modern multigenerational living. Schedule your private showing today!

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Property Details 105 PINE STREET, WINDERMERE, FL 34786

Facts & Features

  • MLS #: O6405163
  • Status: Active
  • Type: Residential
  • SubType: Single Family Residence
  • Year Built: 2015
  • Price: $2,500,000
  • Acres: 0.57
  • Area: 34786 - Windermere
  • County: Orange
  • Bedrooms: 5
  • Bathrooms: 6
  • Full Baths: 5
  • Half Baths: 1
  • Total SqFt: 5,696

Amenities

  • Parking: Boat, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Oversized, RV Garage
  • Garage Spaces: 3
  • View: Pool, Water
  • Waterfront: No
  • Pool: Yes
  • Pool Type: Gunite, Heated, In Ground, Salt Water
  • Spa: Yes
  • Spa Type: Heated, In Ground

Interior Features

  • Interior Features: Accessibility Features, Built-in Features, Ceiling Fans(s), Coffered Ceiling(s), Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
  • Flooring: Ceramic Tile, Luxury Vinyl, Tile, Wood
  • Utilities: Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Sprinkler Well, Water Connected
  • Heating: Central, Electric, Zoned
  • Cooling: Central Air, Zoned

Exterior Features

  • Style: Custom, Florida, Other, Mediterranean, Traditional
  • Exterior Features: Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
  • Lot Description: Corner Lot, In County, Landscaped, Oversized Lot, Private
  • Windows: Aluminum Frames, Blinds, Double Pane Windows, Drapes, Rods, Shades, Shutters, Window Treatments
  • Roof: Shingle
  • Construction: Block, Concrete, Stucco

Schools

  • Elementary: Windermere Elem
  • Middle: Gotha Middle
  • High: Olympia High

Additional Information

  • List Date: 05/07/2026
  • Zoning: SFR

Tax Information

  • Tax Amount: $16,804
  • Tax Year: 2025

Estimated Monthly Mortgage Calculator

This calculator is provided for informational purposes. You should not make any decisions based simply on the information provided. Values indicated are estimates and may not be accurate and are only to be used as a guide. This calculator should not be relied upon in any way as the sole source of information. Please consult your financial, tax or legal advisers for an accurate assessment of your mortgage payments and any advice relating to your personal circumstances.

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