Tucked into an established, tree-lined pocket with rare walkability, 100 Chudleigh Street is a mature-lot Waterdown home with the main floor opened up and reimagined for how families actually live now. This beautifully updated 4-bedroom, 2.5-bath home has over 2,700 sq. ft of finished living space that perfectly blends the open, connected layout buyers love in newer builds with the privacy, greenery, and lot size of an established neighbourhood. The main floor feels bright, warm, and easy, with designer touches throughout, a cozy fireplace, new luxury vinyl flooring, and a large kitchen featuring quartz counters, quartz backsplash, refreshed cabinetry, and generous space to gather. Carpet-free living continues throughout, with four comfortable bedrooms upstairs and a finished lower level that creates a huge suite-style retreat for teens, guests, long-staying in-laws, movie nights, or play space - with room for the wine collection tucked in too. Outside, the backyard is lush and surprisingly private, surrounded by mature greenery with no rear residential neighbours. Steps to everyday amenities, schools, trails, the YMCA, library, restaurants, shopping, Dairy Queen, and the summer farmers market - this is Waterdown family living with space, style, privacy, and true walkability.More details
Welcome to 215 Briar Hill Crescent, a beautifully maintained 4-bedroom, 4-bathroom home in highly desired High Park Estates, one of Ancaster's most established neighbourhoods. Set on an oversized corner lot with mature trees and landscaping, this home offers privacy, generous living space and timeless character. The traditional floor plan features separate living and dining rooms, plus a warm family room with walnut paneling and a wood-burning fireplace. The renovated kitchen overlooks the backyard and opens to a spacious deck, ideal for entertaining. A large main-floor laundry adds everyday convenience. Upstairs, spacious bedrooms are complemented by a beautifully crafted home office with custom pine cabinetry. The finished lower level offers even more room for recreation, media or play. Enjoy a private backyard and prime Ancaster location close to schools, parks, shopping, restaurants, golf and commuter routes. A wonderful alternative to builder-basic, with character, craftsmanship and generous room sizes. There's still time to make this home yours and celebrate the holidays at 215 Briar Hill Crescent! Furnace & A/C (2023).More details
Listed by RE/MAX Escarpment Realty Inc., Brokerage
Nestled in scenic Ancaster Village, this French Chateau-inspired residence offers over 7,000 sqft of luxury backing onto the iconic Hamilton Golf Club, with sweeping views of one of Canada's premier courses. This 3-storey masterpiece features 4 beds, 7 baths, 10.5' soaring ceilings, custom millwork, and refined European design. The main floor is designed for entertaining, showcasing a gourmet kitchen with high-end appliances, quartz counters, custom cabinetry and a large island. Three sets of double doors open to a covered outdoor dining area. A formal dining room with chandelier, fireplace and wet bar adds elegance, while the family room with built-ins and fireplace connects seamlessly to the landscaped yard. Second level is dedicated to ultimate comfort, 3 spacious bedrooms each with private baths & walk-in closets. Primary suite boasts gorgeous stone fireplace, custom walk-in closet & spa-like ensuite with freestanding tub, rainfall shower, glass shower, and private terrace overlooking the golf course. Third level serves as a secluded refuge with spacious living room, large bedroom, full bath & kitchenette. A walk-out portico terrace offers panoramic views of the golf course. Lower level features 9' ceilings, a recroom, fitness room, family room with another fireplace, full bathroom, heated floors & a kitchenette. A wine cellar completes your chateau experience. The property boasts a cedar-ceiling covered deck, outdoor gas fireplace, mature trees for privacy, 5 fireplaces, 3 dishwashers, Terrazzo concrete driveway & large tandem garage with 4-post car lift for the car enthusiast. Crafted with an ICF foundation and whole-home hydronic in-floor heating across all four levels, the residence delivers year-round comfort, remarkably low operating costs, and a reduced carbon footprint-luxury that's as smart as it is beautiful. Close to fine dining, shopping, trails, and conservation areas, this property is a rare haven of sophistication, luxury, and timeless elegance.More details
You may have driven by a thousand times and never known what was waiting at the end of this quiet dead-end street, perched above the Dundas Valley. Rich in history, character and scale, this remarkable home began as the old barn structure associated with the original South Street property and was later home to a former mayor. Behind the solid wood front door, a grand foyer introduces a home filled with original details, including beautifully restored oak floors, 9' ceilings, deep stone walls and original beveled-glass windows that flood the interior with natural light. The main floor offers an exceptionally functional layout with a sprawling living room featuring crown moulding and pot lights, a powder room, and a bright eat-in kitchen with terracotta flooring, generous workspace and an oversized walk-in pantry. A mahogany-clad office enjoys its own entrance to the rear deck and hides a cathedral ceiling above the existing drywall. The side mudroom addition, renovated in 2016, provides laundry, basement access and a second staircase. Upstairs are four generous bedrooms. The existing primary features double closets and five windows, while the rear bedrooms offer garden views and exciting potential to be combined into an impressive primary suite. A substantial walk-through bathroom includes a Jacuzzi tub and separate shower. Roof replaced in 2023. And then there is what lies beneath. Beyond the conventional basement and wine cellar is an extraordinary approximately 30' x 100' stone-vaulted underground space, soaring to heights approaching 20'. Once used during the Prohibition era, it is a remarkable piece of the property's history and an opportunity unlike anything found in a typical home. Imagine a wine cellar and tasting room, private speakeasy, lounge, games room, golf simulator or unforgettable entertaining space. A home with history, substance and possibilities that simply could not be recreated today.More details
7 Fern Avenue is the kind of home that feels right, from the moment you arrive! Tucked away on a quiet, mature, family friendly street in the heart of Waterdown, this beautifully updated 3 bedroom, 3 bathroom bungalow offers the perfect blend of modern comfort, thoughtful upgrades and neighbourhood charm. Inside, you'll find a bright, welcoming layout with updated flooring, pot lighting and beautifully renovated bathrooms. Generously sized bedrooms offer plenty of room to unwind, while the primary bedroom features the added comfort and convenience of its own private 2 piece ensuite. The kitchen has been refreshed with a new fridge, stove and dishwasher (2026). A walkout to the private backyard makes indoor and outdoor living a breeze. While the fully finished lower level and separate side entrance offer fantastic in law potential or flexible space for guests, teenagers, a playroom or home office. Major updates include a new heat pump, furnace, attic insulation, select windows and exterior doors (2024), water heater (2023) and updated electrical panel (2022). The attached double car garage adds everyday convenience. Just a short walk to parks, shops, restaurants and local amenities, this home offers the best of Waterdown living. But what really makes it special is the neighbourhood itself, where kids still play outside, neighbours know each other and there's a genuine sense of community. Beautifully updated, thoughtfully maintained and ready for its next chapter. Welcome home!More details
Welcome to 23 Laurendale Ave, a truly special Waterdown property offering a rare combination of privacy, space and convenience. With approx. 2,000 sf of beautifully finished living space, 3 bedrooms and 2 full baths, this lovingly cared-for home is completely move-in ready. Situated on a nearly half-acre ravine lot, enjoy a peaceful park-like setting with unobstructed views of mature trees and nature that feels more like country or cottage living all while being within walking distance of parks, shopping, schools and everyday amenities. Step outside and discover what truly sets this property apart. The expansive, private backyard is made for relaxing and entertaining, featuring a stunning gazebo with natural gas fire table, two decks, natural stone steps, beautifully maintained landscaping, an irrigation system and a large heated shed that adds even more versatility. Whether enjoying a quiet evening under the gazebo or hosting family and friends, this outdoor space is truly something special. Inside, you'll find new finishes throughout, engineered hardwood across the main floor and new appliances (2021). The finished lower level is an entertainer's dream, featuring a spacious TV room with integrated in-wall speakers, dry bar, wood-burning fireplace and gas stove, creating multiple warm and inviting spaces to gather and unwind. A finished double-car garage plus driveway parking for 3-4 vehicles provide plenty of space. Additional updates include roof (2018), A/C (2019), new front and side doors and many newer windows. A rare opportunity to enjoy exceptional privacy, natural beauty and nearly half an acre in the heart of Waterdown. Your own urban retreat, offering the feeling of escaping to the country without leaving the convenience of the city awaits.More details
Nestled in Ancaster's highly sought-after Parkview Heights neighbourhood, this impressive custom-built home offers over 3,000 sq. ft. of beautifully finished living space, including a fully finished, soundproof in-law suite that provides exceptional flexibility for today's families. Step inside to soaring ceilings, newer hardwood flooring, crown moulding, California shutters, and custom California Closet systems throughout. Expansive principal rooms, two gas fireplaces, and a bright, open layout create an inviting atmosphere for both everyday living and effortless entertaining, while the convenience of main floor laundry enhances every day living. The fully finished lower level features a private in-law suite complete with its own full kitchen, living area, bathroom, bedroom with an egress window, abundant storage, and rough-ins for a second laundry. Whether accommodating extended family, multigenerational living, long-term guests, or evolving lifestyle needs, this space offers remarkable versatility without compromising comfort or privacy. Additional highlights include an updated primary ensuite, lawn irrigation system, double attached garage, and driveway parking for two vehicles. Set on a quiet street in one of Ancaster's premier family neighbourhoods, you'll enjoy mature surroundings, exceptional schools, nearby parks, shopping, everyday amenities, and convenient highway access. A rare opportunity to own a meticulously maintained custom home where timeless craftsmanship, thoughtful design, and pride of ownership are evident throughout.More details
Set on an exceptional lot in one of Ancaster's most sought-after established neighbourhoods, this sprawling custom-built two-storey residence offers the space, layout and solid construction rarely found in today's market. Lovingly cared for and thoughtfully maintained, the home makes an immediate impression with its grand foyer, sweeping circular staircase and generous principal rooms. The main level is designed for family living and entertaining, with a spacious living room featuring a striking fireplace, dedicated home office, large dining area, expansive kitchen and adjoining family room overlooking the backyard. Direct access to the double-car garage adds everyday convenience. Upstairs, four spacious bedrooms and two bathrooms provide excellent accommodation for a growing family. The finished basement adds an extraordinary amount of flexibility, featuring a secondary kitchen, bedrooms, bathrooms, living and recreation spaces, laundry and a separate entrance from the garage, ideal for extended family, teenagers, guests, entertaining or an in-law arrangement. Tons of appeal here for the family, setting and an opportunity. While the home presents an opportunity to introduce today's finishes and design sensibility, its substantial footprint, generous lot, central location and established neighbourhood provide an exceptional opportunity to create something special. An opportunity to bring new life to a well-built family home in a neighbourhood where space, lot size and location are continually in demand.More details
**First Time Home Buyer Friendly** An opportunity to own a detached home in Dundas at a price point that is rarely seen. This future family home sits on a premium 33ft x 133ft lot and includes a massive backyard with plenty of privacy. Located in a mature and sought-after neighborhood, you're tucked away within a family friendly community with tons of amenities nearby. Minutes walk to St. Thomas the Apostle Catholic Elementary School, Rockcliffe Trails, neighborhood parks, and DQ for ice cream on those summer days. For when you're headed out of the suburbs, you're a short drive to highways 403, and just 11 minutes to Aldershot GO Station with some of the most frequent GO train service to Toronto. Need to run errands? Walmart, FreshCo, Home Hardware, Starbucks, The Keg just to name a few, with plenty more shops and restaurants in the plazas that are only 5 minutes away. For those looking to put in a little TLC, the long term value possibilities are endless.More details
A little less upkeep, a little more Dundas living. Just steps from the beloved Dundas Driving Park, this inviting 2+1 bedroom, 2 bathroom bungalow offers comfortable main floor living with the bonus of a fully finished basement. Whether you're looking to downsize or simply love the ease of a bungalow, there's room here to settle in without sacrificing space for guests, hobbies or everyday life. The spacious primary retreat combines two former bedrooms, while the kitchen offers generous cupboard space, stainless steel appliances and freshly repainted cupboard doors. Downstairs, an additional bedroom and full bathroom provide welcome flexibility for overnight visitors. Outside, the beautifully landscaped backyard and covered porch invite slow mornings with coffee, relaxed summer dinners and time spent enjoying the garden. An outdoor natural gas BBQ connection makes entertaining easy. Notable updates include the roof in 2022, furnace and air conditioning in 2021, and a new front porch in 2025. Finished from top to bottom and available for immediate possession, this charming home brings together practical living, inviting outdoor space and the quaint neighbourhood feel that makes Dundas so special.More details
Welcome to 44 Keewaydin Street! This beautifully updated 4-bedroom, 4-bathroom home is situated in one of Waterdown's most desirable, family-friendly neighbourhoods, just walking distance from local schools, a convenient shopping plaza, and the community YMCA. Step inside the bright front foyer, where oversized windows flood the entrance with natural light, leading you to the main floor featuring stunning scraped hardwood flooring and tasteful updates throughout. The layout perfectly balances elegance and daily comfort, offering a welcoming living room that adjoins an open dining area, seamlessly flowing into a spacious eat-in kitchen. From here, doors open to a low-maintenance backyard oasis complete with a relaxing Jacuzzi hot tub and lounge area. The upper-level oversized family room provides a warm, cozy retreat anchored by a classic gas fireplace. The primary bedroom serves as a true getaway with its beautifully upgraded ensuite bathroom, and the fully finished basement expands your living space with a large recreation room and an additional bedroom. Practicality and curb appeal are front and centre with an expansive double driveway leading to a spacious double-car garage, ensuring plenty of parking and storage space. Beyond the property lines, the location is truly unbeatable. Enjoy Waterdown's Memorial Park just a few minutes away, renowned for its winter skating loop, walking path, playground and the annual Waterdown Ribfest. Waterdown's vibrant downtown core is just a few minutes farther with additional shops, restaurants and businesses, and a breathtaking local scenic waterfall that perfectly highlights the region's stunning natural landscape. For outdoor enthusiasts and active pets, nearby wooded trails lead directly to Joe Sam's Leisure Park, which offers baseball diamonds, playgrounds, and a leash-free zone, all while maintaining incredibly easy access to the QEW, 401, and 407 highways for a seamless daily commute. Enjoy all that Waterdown has to offer!More details
Data was last updated October 8, 2026 at 06:15 AM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website.
The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.