1099 Henry Street, Wellesley - SOLD!
- The Lambert Group
- Sep 23, 2025
- 4 min read
Updated: Oct 17, 2025
Thank you, Henry Street!
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Charming Bungalow Living in the Heart of Wellesley
Above Grade Square Feet: 1,109.86 (iGuide Measurement)
Below Grade Square Feet: 1,201.65 (iGuide Measurement)
Total Square Feet: 2,311.51 (iGuide Measurement)
Welcome Home to 1099 Henry Street!
Welcome to 1099 Henry Street, a charming bungalow nestled in the heart of Wellesley. Set on nearly half an acre, this property boasts a backyard that stretches over 260 feet deep—perfect for families who love spending time outdoors. With its blend of small-town charm, spacious layout, and a warm, tight-knit community, this home offers the ideal setting to grow, gather, and create lasting memories. Step inside, settle in, and discover why 1099 Henry Street might just be the perfect place to call home.
A Floorplan Offering a Comfortable Family Living Experience
From the moment you step through the front door, you'll notice that this home feels bright, comfortable, and offers some great updates.
Step into the bright and inviting living room, recently updated with luxury vinyl plank flooring and fresh, neutral finishes that suit any style. An oversized front window fills the space with natural light, creating a warm and welcoming atmosphere from the moment you walk in.
Continue toward the rear of the home to discover a thoughtfully designed eat-in kitchen, complete with built-in cabinetry and plenty of room for family meals or casual entertaining. Practicality meets comfort here, with direct access to both the attached garage and the back deck—perfect for outdoor dining thanks to a natural gas BBQ hookup.
The main level also features three spacious bedrooms, each with its own distinctive charm, and a freshly painted 4-piece bathroom that ties the space together beautifully.
Endless Possibilities Below
With a spacious main floor comes nearly 1,200 square feet of potential downstairs — a partially finished lower level that’s ready for your personal touch.
The heavy lifting has already been done: the space has been professionally spray-foamed right up to the subfloor, with drywall installed on both the walls and ceiling. Recent electrical work has been completed throughout by a licensed electrician, so you're off to a solid start.
Even better? Key features have already been roughed in, including a full bathroom, bar area, and gas fireplace — giving you a true blank canvas to create the perfect rec room, guest suite, home gym, or whatever your lifestyle calls for.
They Don't Make Lots Like This Anymore!
The backyard is truly the showstopper of this property. At 65' wide and 260' deep, this lot spans nearly half an acre, giving you space that's usually only found in the country.
The backyard here truly sets this home apart, offering a fully featured outdoor oasis with endless possibilities. The spacious deck and patio come equipped with a natural gas hookup—ideal for hosting barbecues and gatherings with family and friends.
Pet lovers will appreciate the fully fenced yard, providing a safe and secure space for your furry friends to roam freely. Plus, mature trees line the perimeter, creating a natural privacy screen that enhances the sense of tranquility and seclusion.
Welcome to This Amazing Community!
Wellesley is known for its strong sense of community, where small-town charm and local traditions truly shine. Families will especially appreciate the close proximity to Wellesley Public School, just a 5 minute walk from the home—making the morning school run a breeze.
Beyond the school, the neighborhood offers plenty to enjoy: Pym’s Village Market, the newly built Recreation Centre, and the famous Apple Butter & Cheese Festival, all contributing to a vibrant, welcoming community spirit. And with Kitchener-Waterloo just a quick drive away, you can enjoy peaceful small-town living without sacrificing easy access to big-city amenities.
Wonderful Wellesley!
Moving to Wellesley is so much more than just buying a house in a neighbourhood - It's buying a home in a community! And we mean community in the truest sense of the word!
Wellesley is the kind of town where your entire street spends hours with you searching for your lost dog in the rain. A community that comes together to support each other as one of their own face a devastating house fire that leaves them with barely the clothes on their back. It's a place where hot, home cooked meals are left on your doorstep when a new baby is born and you can't remember the last time you brushed your teeth, let alone ate something.
Wellesley is a special place- a community in every sense of the word and we are waiting for you!
Everything You Need Is Here!
The town of Wellesley offers everything you could possibly need- all within walking distance from your home!
The new Wellesley Recreation Centre provides something for everyone in the family - it includes a fitness centre, gymnasium, meeting rooms, and of course a hockey arena - home of the Wellesley Apple Jacks! Outside you can enjoy a playground, skate parking, basketball courts, soccer fields and plenty of walking trails. All of this located a very short walk from your home!
The Wellesley Community Centre is close by and includes soccer fields, baseball diamonds, an accessible children's park, splash pad and a leash-free dog park! Truly something for everyone in the family!
Restaurants:
Home to renowned Schmidtsville Restaurant, your dining out options are simply delicious!
Craving Pizza? Stop by Olympic Pizza for a slice to a signature meal including chicken wings, subs and wraps!
The Wellesley Lounge caters to all your pub needs, whether you're enjoying a meal with family or catching the game with a cold drink at the bar.
Looking for an exceptional coffee and Smooties?
Don't hesitate to check out Resolute Smoothie and Espresso Bar for one of the most delicious hand-made lattes you have ever had.
Not far from your home is Wellesley Public School! Known in the community as an excellent school with some of the brightest and most engaged teachers! Go Eagles!
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