5 Undercliffe Avenue

Durand, Hamilton, L8P 3G9
FOR SALE
$2,395,000
5 Undercliffe Avenue, Hamilton
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
5 Undercliffe Avenue
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6
BEDROOMS
6
BATHROOMS
1
KITCHENS
19 + 7
ROOMS
X13810426
MLSID
Contact Us
Property Description
Nestled beneath the escarpment in Hamilton's prestigious Durand neighbourhood, this stately Georgian Revival residence offers a rare opportunity to own a piece of architectural and cultural history. Built in 1924 by the Levy family, this distinguished home was once owned by philanthropist and art collector Herman H. Levy, whose notable collections were later donated to McMaster University and the Royal Ontario Museum. Offering over 5,000 sq. ft. of living space with ample room for both comfortable family-living and elegant entertaining, the home blends timeless character with thoughtful updates. A classic centre hall layout and 9-foot ceilings create an elegant flow throughout the main level, complemented by original millwork, detailed mouldings, and three fireplaces. The walnut library provides a warm and refined retreat, while the updated kitchen features granite counters, a large island, quality appliances, and a secondary staircase that reflects the original design. The second level offers four spacious bedrooms, each with ensuite access. The primary dressing area includes original built-ins, a vintage ironing board, and a discreetly integrated safe installed by the Levy family. The third floor adds flexibility with two additional bedrooms, a full bathroom, and a separate living area ideal for a nanny suite, multigenerational living or a private workspace. The lower level includes a laundry area with original cedar chute servicing all levels, a workshop, bathroom, walk-in safe or wine cellar, and interior access to the heated garage. Additional features include a slate roof, copper downspouts, central vacuum, EV charging station, and zoned heating and cooling. Set on a private, treelined lot, the backyard features a heated saltwater pool, year-round hot tub, and covered porch, offering a quiet setting for relaxation and entertaining. Located close to parks, schools, hospitals, the Bruce Trail, downtown amenities, and Highway 403, this is a truly rare offering.
Property Features
Electric Car Charger, Fenced Yard, Golf, Hospital, School, Arts Centre, Auto Garage Door Remote, Bar Fridge, Central Vacuum, Floor Drain, Guest Accommodations, Storage, Water Heater Owned, Private, Alarm System, Monitored, Security System, Smoke Detector, Carbon Monoxide Detectors, Living Room, Natural Gas, Wood
Property Details
Address
5 Undercliffe Avenue
Community
Postal Code
L8P 3G9
Property Type
Detached, Detached
Zoning
R2
Lot Size
120' x 70'
Taxes
$22,951 (2025
Basement
Full, Walk-Out
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Pool
Inground, Salt
Parking Spaces
2
Garage Type
Attached
Listing contracted with Royal Lepage State Realty
102 Cumming Court, Hamilton
5+1
BEDS
6
BATHS
$2,349,900
FOR SALE
Crafted with exceptional attention to detail and completed in 2025 (Tarion warranty), this custom two-storey luxury home offers nearly 6,000 sqft. of finished living, 5+1 bedrooms, 6 total baths, and a contemporary transitional design blending sophistication with family-friendly functionality. Situated on a 75 x 105 ft lot in Ancaster's Nakoma neighbourhood, it features striking curb appeal with a stone-and-stucco exterior and a 2.5-car triple tandem garage. Inside, soaring 9 ft ceilings on all three levels, wide-plank white oak hardwood, 8 ft solid core doors, 9" baseboards, and oversized windows create a sense of grandeur. The 19-ft great room showcases floor-to-ceiling windows and a 42" gas fireplace flanked by custom cabinetry. A main-floor office with built-ins, formal dining room, and powder room provide elegant, purposeful spaces, while the dining table converts into a pool table for dual-purpose entertaining. The gourmet kitchen features black cabinetry, a 9' x 5' waterfall quartz island, full-slab quartz backsplash, champagne and honey bronze fixtures, Bertazzoni appliances, and a walk-in pantry and servery with black stainless-steel sink. Adjacent are the mudroom/laundry with garage entry and a main-level bedroom with ensuite. Upstairs, four bedrooms each have ensuite access, including a primary retreat with 10 ft tray ceiling, oversized walk-in closet, linear fireplace, and spa-inspired 5-piece ensuite with heated floors. The finished lower level offers 9 ft ceilings, oversized windows, sixth bedroom, full bathroom, linear fireplace, and endless possibilities. Additional features include radon mitigation, 200-amp service, hardwired security system, and DryCore subfloor. Outside, the back patio provides a starting point for a dream outdoor space, with a pre-approved building permit for an in-ground pool and gas lines for BBQ. Centrally located, this home offers walkability to schools, parks, shops, and quick access to Hwy 403.
79 Amelia Street, Hamilton
5+1
BEDS
6
BATHS
$2,189,000
FOR SALE
An unparalleled mid-century modern masterpiece, designed by renowned architect Jerome Markson and built by Charles Oliver in 1959, sits on one of Hamilton's prestigious Kirkendall neighbourhoods. This sprawling 4,643-square-foot home boasts 5 bedrooms, 6 bathrooms, and is set on a premium lot backing onto the scenic Carolinian Forest of the Niagara Escarpment. Designed with an exceptional open-concept floor plan, the home features floor-to-ceiling, extra-wide patio doors that flood the main level with natural light. The formal living room highlights a wood-burning fireplace with a stunning fieldstone surround, while the formal dining room offers hardwood floors and sliding door access. A sunken great room with dramatic floor-to-ceiling windows features two sets of custom German patio doors leading to an interior courtyard and the rear yard. The spacious kitchen is equipped with in-floor radiant heat, an office nook, stainless steel appliances, a dinette with a bay window, and an indoor grilling station with a reclaimed brick surround. The L-shaped bedroom wing includes two guest rooms with private ensuite baths and a luxurious primary suite featuring an updated ensuite with a glass shower, soaker tub, double vanity, and in-floor heating. The lower level offers incredible in-law potential with a separate on-grade entrance, a large family room, recreation room, studio, and a 3-piece bath. Steps to Locke Street, restaurants, parks and hospitals. A rare find on one Hamilton's most magnificent streets. Lets get you home! Luxury Certified.
345 Mountain Brow Road, Hamilton
7
BEDS
5
BATHS
$2,395,000
FOR SALE
Set on approximately 3-acres (per MPAC) this property overlooks the breathtaking natural landscape of Smokey Hollow and backs directly onto the iconic Bruce Trail. This remarkable gated estate offers a rare opportunity to acquire one of the area's most picturesque and private estates. A graceful, swooping driveway leads through expansive, awe-inspiring grounds, creating a dramatic sense of arrival while remaining discreet and private from the road. The 2.5-storey residence offers 7 bedrooms and 5 bathrooms, along with a library with a fireplace. The home in its current state needs to be renovated. Outdoor features include an inground swimming pool and a detached double-car garage, all set within the property's remarkable estate setting. For those with a vision for transformation, a new house rendering design by SMPL Design Studio offers inspiration for a spectacular modern residence. Ideally located just minutes from downtown Waterdown, Burlington, and the convenient Aldershot GO Station, providing easy access to amenities and commuting options. Property and all structures are being sold in AS-IS condition. Floor plans and a survey are available. Either renovate the existing house or build a new one. Exterior photos are current and from a few years ago. Interior photos and new home renderings are for creative / illustrative purposes only.
58 Forsyth Avenue, Hamilton
5+1
BEDS
7
BATHS
$2,180,000
FOR SALE
Nestled in the prestigious Westdale community of Hamilton, this exceptional custom-built residence sits on a rare 75 x 100 ft lot and offers over 3,500 sq ft of refined living space above grade. A grand 2-storey detached home featuring 5+1 bedrooms and 5 bathrooms, designed for both elegant family living and sophisticated entertaining. Spacious principal rooms, a finished basement, and a built-in 2-car garage complement the expansive circular driveway with parking for up to 8 vehicles. Carpet-free interior with thoughtfully updated finishes throughout, including built-in oven and ample storage. Flexible layout ideal for multigenerational living or executive families. Located steps to prestigious schools, McMaster University, parks, trails, and vibrant Westdale Village shops, cafes, and restaurants. Minutes to Royal Botanical Gardens, Cootes Paradise, and easy access to Highway 403, making commuting seamless. A rare opportunity to own a distinguished home in one of Hamilton's most sought-after neighbourhoods
22 Burt Court, Hamilton
5+1
BEDS
5
BATHS
$2,099,000
FOR SALE
Nestled on a spectacular private ravine setting, this exceptional custom residence offers over 6,200 square feet of beautifully finished living space designed for both grand entertaining and comfortable family living. A dramatic two-storey foyer welcomes you to this impressive home featuring six spacious bedrooms and five bathrooms. The thoughtfully designed layout includes a main floor primary retreat with an ensuite complete with Jacuzzi tub and separate shower. The expansive main level boasts a gracious living room, an elegant formal dining room with seating for 12, and a spacious kitchen with separate breakfast area overlooking the backyard oasis. The stunning family room showcases a soaring cathedral ceiling and french doors opening onto a balcony with panoramic views of the resort-inspired swimming pool seamlessly integrated into the natural ravine landscape. The upper level features four generously sized bedrooms with convenient adjoining and main baths, providing exceptional accommodation for family and guests. The fully finished lower level offers an additional 2,400 square feet, highlighted by a spectacular 1,000 square foot recreation room and a private suite complete with bedroom, 3 piece bath, sauna, kitchenette, laundry area, abundant storage and a large fruit cellar - ideal for extended family or multi-generational living. Surrounded by mature trees and offering unparalleled privacy, this remarkable residence combines timeless elegance, generous living spaces and a truly extraordinary setting. A rare opportunity to own one of Stoney Creek's finest ravine properties.
77 Flanders Drive, Hamilton
5+1
BEDS
5
BATHS
$1,999,999
FOR SALE
Tucked into one of Waterdown's most coveted enclaves of executive homes, this Georgian residence offers over 4,000 square feet of above-grade living and a setting that feels worlds away, while remaining minutes from everything. Set against a backdrop of protected, naturalized parkland governed by the Niagara Escarpment and Bruce Trail, this is a property defined as much by what surrounds it as what's within it. Deer, wild turkey, and songbirds move through the tree line beyond the backyard. You have a view that changes with the season and never gets old. Inside, four bedrooms fill the main house, complemented by a fully finished basement with an additional bedroom, plus a striking 1,000-square-foot above-grade accessory apartment (built 2017) with one bedroom and full living space. This gives endless flexibility for multi-generational living or in-home nanny. The gourmet kitchen anchors the main level: a commanding island, quality Miele appliances and sightlines straight out to the escarpment beyond. It's a space built for both the people who cook...and for the people who'd rather watch the view while someone else does. Freshly painted throughout in a bright, neutral palette, the home is ready to move into and make your own. Outside, the landscaping has been thoughtfully designed with drought-tolerant native plantings, low-maintenance and built for the long term. A hot tub anchors the backyard, offering a quiet spot to unwind after a day on the Bruce Trail or a walk into the village. Practical comforts are built in too: two furnaces, two A/C units, and a location that keeps you close to Waterdown Village's shops and restaurants on foot, with easy access to Aldershot GO and the major highways for the commute. This is Waterdown living at its finest. RSA.
149 Miller Drive, Hamilton
5+1
BEDS
5
BATHS
$1,999,900
FOR SALE
Welcome to 149 Miller Drive, an exceptional luxury residence nestled in one of Ancaster's most prestigious & sought-after neighbourhoods. Set on an impressive 62x235 ft lot surrounded by mature trees & beautifully landscaped grounds, this extensively renovated home offers over 6000 sq ft of finished living space designed for upscale family living & entertaining. Featuring 5+1 bedrooms & 4 1/2 bathrooms, this stunning property showcases a seamless blend of timeless elegance, quality craftsmanship, & modern functionality. The heart of the home is the spectacular custom gourmet kitchen, complete with premium built-in appliances, quartz countertops, oversized island with breakfast bar seating, custom cabinetry, & designer finishes, all flowing seamlessly into expansive principal living & dining spaces ideal for everyday living & hosting guests. Multiple fireplaces, spacious family areas, & refined finishes throughout create a warm yet sophisticated atmosphere. A beautifully designed indoor inground pool & fitness retreat offers a true year-round resort-style experience rarely found in residential homes. Upstairs, the luxurious primary suite serves as a private retreat featuring a spa-inspired ensuite & walk-in closet. Above the triple car garage, you'll find a separate private suite complete with its own 3-piece bathroom, making it ideal as a nanny suite, guest retreat or multi-generational living space. The fully finished lower level further enhances the home's versatility including a recreation room, office space, additional bedroom, & walk-out access. Outside, enjoy the serenity & privacy of the expansive backyard featuring mature landscaping, multiple entertaining areas, hot tub, concrete patio, & tiered deck space perfect for relaxing or entertaining. The beautifully designed exterior is complemented by a circular concrete driveway, triple car garage, & ample parking. Located near top-rated schools, parks, shopping, dining, golf, highway access, & major amenities.
43 Third Road, Hamilton
5
BEDS
5
BATHS
$1,998,000
FOR SALE
Don't miss this incredible opportunity to own a stunning custom built home (2019) that offers the privacy of country living on a 1.4 acre lot, while still being very close to all the city amenities! With over 5,000 sq ft of living space (not including the full , unfinished basement with endless potential -9 ft ceilings and over 2600 sq ft), this home is ideal for multi-generational families with a seperate 1 bedroom in-law suite on the main level- with it's own laundry room and direct entry into the 4 car garage. Enjoy the beautiful sunsets on the covered porch with no rear neighbours and create your dream backyard oasis on this expansive lot! When you walk into this home, you will be amazed by the elegant detailed finishings including 10 ft coffered ceilings on the main level, hardwood and tile floors and a chef's dream kitchen with a walk-in pantry, oversized centre island, breakfast area and beautiful stonework around the stove. Relax in the family room with a gas fireplace or enjoy your favorite book in your own library! Enjoy the convenience of having a mudroom with custom built shelves and closets and lots of storage space. On the upper level, you will find the primary bedroom retreat with a 5 pc spa-like ensuite, walk-in closet and a direct walkout to your private balcony. Enjoy family time in the upstairs game room that overlooks the backyard or work from home in your own private office. There are also 3 additional bedrooms with walk-in closets, hardwood floors and large windows overlooking the front yard (with no neighbours at the front and a view of an open field). This luxurious custom home is a must-see!
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