Turnkey Windfall Ski Home - Furnishings Optional + Proven $20K Seasonal Rental Income. Welcome to 106 Sycamore Street - a fully upgraded, move-in-ready home in the heart of Windfall, offering the perfect blend of lifestyle and investment potential. This beautifully finished Bedford model features 3 bedrooms and 2.5 baths above grade, plus a fully finished basement with a full bathroom and media space - ideal for hosting family and guests. Positioned at the top of a quiet T-street, the home offers rare sight lines toward Osler Ski Club and Blue Mountain, setting it apart from typical interior-facing properties. Thoughtfully upgraded throughout, the interior showcases designer lighting, custom feature walls, shiplap and barn board accents, and a warm, inviting layout designed for both comfort and style. Offered with furnishings optional, this home can be purchased fully turnkey for immediate enjoyment or as a clean slate for personal use. With a proven track record of approximately $20,000 in seasonal winter rental income, it offers strong revenue potential. The backyard includes irrigation and added privacy with mature maple trees, while the finished basement provides valuable additional living space not found in many comparable homes. Located just minutes from Blue Mountain, private ski clubs, trails, and all-season amenities, this is a rare opportunity to own a flexible, fully equipped Windfall home ready to enjoy from day one! POTL for this property is $91.88 for use of The Shed - community area with pool, hot tub, gym, sauna, community room!
Private parking with 2 total spaces, including 1 covered space
Has garage
Construction
Vinyl siding and stone exterior
Utilities
Public water
Cable available
Sale and tax history for 106 Sycamore St
Sale History
Tax History
Date
Event
Price
TREB #X13064878
Apr 30, 2026
Listed
$929,900
TREB #X9367335
Nov 1, 2024
Listed
$1,038,000
Nov 1, 2024
Delisted
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Sep 25, 2024
Listed
$1,038,000
TREB #X10404012
Sep 25, 2024
Listed
$1,038,000
Executive Fully Furnished Permanent Or Vacation Home. Nestled In Esteemed Windfall Community, Tastefully Designed 3 Bedroom, 4 Bathroom Short Stroll To Ski Trails Of Blue Mountain Resort And Renowned Blue Mountain Village. Stunning Views Of Both Blue Mountain And Osler Bluff. Numerous Upgrades: Granite Countertops Throughout, Gas Fireplace With Custom Wood Beam Mantel, Stainless Steel Appliances. Kitchen Upgraded Cabinetry With Soft Close Doors & Pot Drawers, Fully Stocked With All Glassware, Dishes, Pots & Pans, Etc. Outdoor Back Deck Equipped With BBQ Gas Line, LED Pot Lights & Designer Lighting Fixtures Enhance Ambiance Throughout. Each Bedroom Is Complemented By Stylish Ceiling Fans, Professionally Installed Feature Walls Add Character. Expansive Primary Bedroom Includes King Sized Bed, Walk-In Closet, 5pc Ensuite With Mountain Views From The Soaker Tub, Double Sink Granite Countertops, Glass Shower. 2 Additional Queen Sized Bedrooms, Walk-In Closets, Full Bathroom. Under Stair Storage, Finished Basement With Full Bathroom And Fireplace. Every Detail Meticulously Considered To Ensure Enjoyment Throughout All Four Seasons In Blue Mountains. Owner Has Access To The Shed, Windfall's Luxurious Multi Million Dollar Recreational Facility Featuring Hot And Cold Pools, Gym, Sauna, Communal Party Room With Kitchen. Endless Biking & Hiking Trails, Multiple Golf Courses, Pickleball Courts. Offers Investment Potential, At Lease Rate Of Approx. $5500/Month.
TREB #X6745326
Apr 26, 2024
Price Changed
$1,059,000
Aug 16, 2023
Listed
$1,180,000
As the MLS and public records start to fill up, we'll list the details here.
Public record
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Style
Single Family Residential
Region
Grey County
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Last updated by owner on Apr 30, 2026.
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