Stipley Real Estate for Sale

A Rare and exceptional downtown Hamilton investment opportunity not to be missed! This meticulously owner-operated 7-unit building comprising all self-contained one-bedroom units has been maintained since 2008 and underwent a complete gut renovation across every floor, delivering a truly turnkey asset in clean, move-in ready condition. Spanning approximately 4,580 sq ft across four levels (basement 1,425 sq ft main 1,689 sq ft 2nd 1,061 sq ft 3rd 405 sq ft), the property features comprehensive 2 lb spray foam insulation across all levels, in-floor heating throughout, a German boiler system that efficiently serves both building heat and hot water, a single garage with side door, separately metered hydro for 5 of 7 units, parking for 5 vehicles, and additional laundry income. What truly sets this property apart is its coveted C2 zoning, opening the door to a commercial component on the main floor - whether a boutique retail shop, café, professional office, or personal service use - while the live-work opportunity allows an owner-occupant to run their business from the ground floor while residing above, dramatically reducing overhead and maximizing lifestyle flexibility. Positioned in an excellent central downtown location with outstanding visibility along a high-traffic corridor, this building benefits from strong daily foot traffic, exceptional signage exposure, and effortless access to Hamilton's vibrant amenities, restaurants, and transit routes. A true turnkey investment with significant upside, and opportunities like this are few and far between!

Welcome to a well-cared-for 3-bedroom, 2-bathroom home offering comfort, function, and meaningful updates throughout in an area that's steadily evolving. Over the past several years (2018 onward), the home has seen important improvements including the roof shingles, windows, electrical panel, air conditioning, appliances, and laundry-providing a solid foundation for peace of mind. The main level offers a practical layout with bright living spaces and the convenience of a mudroom, supporting everyday ease of living.Outside, enjoy a fully fenced backyard with room to relax, garden, or further enhance the outdoor space, along with two dedicated parking spaces.The neighbourhood continues to see positive momentum, with a growing mix of local businesses, creative spaces, and community-driven energy. Nearby amenities include independent cafes, restaurants, and cultural spots such as the Cotton Factory arts collective, independent cinema, local coffee houses, and popular neighbourhood eateries. A solid opportunity for first-time buyers, investors, or those looking to get into an area with long-term upside and a strong sense of local character.

This 2.5-storey home sits in the heart of Central Hamilton, just steps from Gage Park. Thoughtfully updated, it blends timeless character with modern comfort across 3 bedrooms and 2.5 baths. A covered front porch welcomes you into a spacious foyer that opens to a bright living and dining area, where pot lighting highlights updated flooring and a striking feature wall. The updated kitchen impresses with white cabinetry, stainless steel appliances, and butcher block countertops-perfect for family meals or entertaining. A piano-style staircase leads to the second level, offering two generous bedrooms, including one with a sun-filled bay window. An exterior door accesses the flat roof over the kitchen-a space full of potential. The elegant 3-piece bath features an oversized glass shower. The third level is a true primary retreat with two closets and a spa-inspired 3-piece bath with a stand-up glass shower. The lower level adds excellent storage, laundry, and a finished 2-piece powder room. Outside, enjoy a low-maintenance turf yard with a deck, leading to an oversized 1.5-car garage with an updated door. Recent updates include windows, roof shingles and eavestroughs (2017), flooring and light fixtures (2020), central air (2020), electrical panel (2020), main drain replacement (2020), and furnace (2023). California shutters and oversized mouldings throughout preserve the home's original character. With cafes, shops, and transit just steps away, 39 East Bend Avenue South is the perfect blend of location, character, and quality upgrades.

Welcome to 37 Connaught Avenue South, where timeless character meets one of Hamilton's most connected, neighbourly communities. Set on a quiet, tree-lined street in Gibson/Stipley South, this is more than a home, it's a place where neighbours know each other, kids play outside, and there's a true sense of community. This beautifully updated 2.5-storey home offers 4 spacious bedrooms and 2.5 bathrooms, blending historic charm with thoughtful modern upgrades. Freshly painted and move-in ready, every space feels warm and refined. At the heart of the home is a stunning renovated kitchen with soaring ceilings, custom cabinetry, stainless steel appliances, granite countertops, and a functional peninsula perfect for everyday living and entertaining. It flows into a welcoming dining area with hardwood floors and an original beam ceiling. The cozy family room features pocket French doors, hardwood flooring, a gas fireplace with natural stone surround, and custom built-ins, the perfect place to unwind. Original character shines throughout with coffered ceilings, walnut trim, solid wood doors, antique hardware, inlay floors, and beautiful stained glass details. Location is everything. Just minutes to Ottawa Street's vibrant shops, cafés, antique markets, and local dining, plus close to Gage Park where you can enjoy trails, the greenhouse, playgrounds, festivals, and year-round outdoor activities. 37 Connaught Avenue South isn't just a home, it's a lifestyle rooted in community, character, and convenience.

This solid brick 2.5 story home with many upgrades and improvements is fully finishedfrom top to bottom. Layout allows for single family with in-law suite setup. Featuring an inviting entry, foyer with spacious closet, living room, dining room, kitchen and two-piece bathroom all in the main level. Second level displaysa second kitchen with walkout to the deck overlooking the backyard. Also on the second level is the familyroom with hardwood floors (can be a 4th bedroom to suit your needs) and 2-piece bathroom with laundry. The third level has the primary bedroom with 3pc ensuite bathroom plus cubby space for additional storage.Make your way down into the basement level where you'll find a 4- piece bathroom, twobedrooms, laundry and utility room. The fully gated backyard is well manicured with lovely gardens and a concrete patio +pathway to a BONUS SOLID 392 sqft BLOCK GARAGE which is perfect for a variety of usesgiving you a secure parking space plus plenty of room for tools and storage. Plus thisawesome garage includes a natural gas furnace, 30 amp dedicated electrical serviceand hoist (negotiable). Additional Features worth noting: backflow valve, oak railings &risers, air-conditioning units, brand new roof in 2026, sewer line, electrical, all ductwork andattic insulation all upgraded and replaced in 2010. Walking distance to most essentialamenities, plus parks, schools and public transit.

Opportunity knocks at 153 Gage Ave N! This beautifully updated 3-bedroom home offers the perfect blend of timeless character, modern comfort, and unbeatable convenience in Hamilton's vibrant Central East neighbourhood. Walk to Tim Hortons Field, explore the trendy shops, cafés, restaurants, and local markets of the Ottawa Street North shopping district, or enjoy the gardens, trails, and year-round community events at nearby Gage Park. With quick access to the Red Hill Valley Parkway, Nikola Tesla Boulevard, the QEW, and public transit, commuting throughout Hamilton and the GTA is a breeze.Freshly painted from top to bottom, this move-in-ready home welcomes you with new tile flooring through the foyer, kitchen, and main floor powder room. The updated kitchen flows seamlessly into bright and inviting living and dining spaces, where original inlaid hardwood flooring, elegant coved ceilings, and beautiful stained-glass accents showcase the home's classic charm.The second floor has been completely refreshed with new luxury vinyl plank flooring throughout and features a spacious primary bedroom, two additional generously sized bedrooms, and a stunning brand-new 4-piece bathroom with a subway tile surround. Outside, you'll find a private backyard, detached single garage, and driveway parking for two additional vehicles. As an added bonus, the quiet church next door creates a uniquely peaceful setting rarely found in the city.Whether you're a first-time buyer, young family, or investor, this is an exceptional opportunity to own a beautifully updated home in one of Hamilton's most sought-after urban neighbourhoods. Don't miss your chance-schedule your private showing today and discover everything 153 Gage Ave N has to offer.

A stately home rich in old-world charm, timeless craftsmanship, & the kind of space today's buyers dream of-a home to grow into, make your own, & cherish for years to come. Filled with original character & beautifully preserved details. From the moment you step inside you will be in awe of the unspoiled wood accents, rich hardwd flrs,elegant pocket doors, coffer ceiling & two incredible original fireplace mantles (one featuring a functioning gas fireplace). A double staircase to the 2 nd lvl adds to the appeal. Unwind in the inviting den, cozy up by the fire in the living rm, host memorable dinners in the formal dining rm, or prepare family favourites in the functional galley kitchen. Just beyond, a bonus pantry rm adds incredible practicality with extra storage,sink, & additional counter space. Upstairs, the 2 nd lvl offers four bedrms & a full bathrm complete with clawfoot tub. The primary bedrm features access to a rear balcony-an ideal spot to enjoy a quiet morning coffee or unwind at day's end. The finished attic provides even more space, ready to suit your lifestyle as a studio, home office, or private escape complete with another full bathroom. Downstairs, the partially finished basement boasts ample storage, workshop potential, & a 3-piece bathrm ready for a thoughtful refresh. This is more than just a house-it's a home with soul ready for its next chapter and for a new owner to make it their own while preserving the beauty of its remarkable past. RSA

Stunning 1,427 sq. ft. semi-detached century home just steps from Hamilton Stadium! This beautifully updated home blends historic charm with modern finishes. Soaring ceilings and an open-concept layout create a comfortable, airy feel. The custom kitchen is a showstopper - featuring oversized tile, quartz island and counters, sleek backsplash, and custom cabinetry perfect for entertaining. New hardwood flooring throughout the main floor adds warmth and style. Upstairs offers spacious bedrooms and updated bathrooms. The primary bedroom includes newer hardwood and a rare, beautifully finished ensuite bathroom a unique feature in homes of this era. The finished attic adds a versatile 4th bedroom or ideal office space, complete with recent spray foam insulation for year-round comfort. Newer Central A/C. Enjoy both front driveway parking and private rear parking via the laneway. Live just steps from Tim Hortons Field and experience the vibrant community spirit, nearby parks, shopping at Centre Mall, easy QEW access, and more. A truly exceptional opportunity in a fantastic location!

Welcome to 34 Edward Street!This Gibson all brick home is the perfect opportunity for first time buyers to start their home ownership journey. Main floor features a well lit living space, large dedicated dining room and kitchen with access to back deck and yard. Upstairs you'll find 3 bedrooms, renovated 4-piece bath and linen closet. The basement has laundry and tons of storage space. 34 Edward Street offers parking for 1 car, covered front porch, large back deck with pergola and yard space to exercise your green thumb. Located in the Gibson neighbourhood this home is very walkable with proximity to transit routes, Tim Horton's Field, shopping, dining, parks and schools. Updates include rewiring (2020), pest prevention from Skedaddle (2023), paint, most light fixtures, furnace (2017), bathroom reno (2023).

Welcome to 127 Barnesdale Avenue N, a thoughtfully updated, move-in-ready detached bungaloft offering exceptional versatility in Hamilton's North Sherman neighbourhood. Situated on a 23 x 129 ft lot, this charming home features 2 bedrooms, 1.5 bathrooms, main-floor laundry, and a functional layout that maximizes both living and storage space. A standout feature of this property is the impressive 1,100 sqft detached garage/workshop with laneway access at the rear. Equipped with electrical service, roughed-in plumbing for a future bathroom, and a newly insulated potential office area, the space presents a wide range of possibilities for hobbyists, tradespeople, entrepreneurs, or buyers seeking additional workspace. Property zoning permits one and two-family dwellings, potential to convert the garage into laneway auxiliary unit. The bright main level has been extensively updated with new flooring throughout, updated kitchen cabinetry, refreshed bathroom finishes, and fresh paint. Upstairs, the loft-style second bedroom and flex-space provide additional storage space, creating flexibility for a variety of living arrangements. Numerous exterior improvements have been completed, including new siding with an additional R-4.5+ insulation value, new soffits, fascia, gutters and downspouts, and all new windows in both the house and garage. Cement parging has been applied to the basement walls.Conveniently located within walking distance of public and Catholic elementary schools, just steps from Lucy Day Park, and a short walk to Tim Hortons Field, this property offers an excellent opportunity for first-time buyers, investors, and those seeking a home with exceptional workshop space.

Absolute show stopper!! Fully renovated top to bottom home with high quality finishes, very bright and large windows. Located in sought after Gibson-Stipley neighborhood is a turn-key move in ready home. Main level features a open concept Living and Dining room with accent wall and new flooring throughout featuring a built in coffee station. Powder room features designer touches and modern light fixtures throughout. Brand new custom kitchen is a chefs delight featuring quartz countertop and backsplash, large island with storage, brand new S/S appliances and new washer dryer. Second level has spacious 3 bedrooms with designer accent walls and a bathroom with modern vanity and glass standing shower. Basement is fully finished with a rec room and a full bath with modern touch. Backyard oasis with fully fenced providing full privacy. Close to grocery stores, bus route, shopping, Tim Hortons field, Restaurants, schools, hospitals and many more! Shows AAA, wont disappoint!!Excellent home for First Time buyers!

Over a century old and better than ever. This solid brick Hamilton home is the kind of property that earns a second look, and a third. Original stained glass windows frame a beautiful living room with soaring ceilings and ornate white millwork. High ceilings throughout. Thoughtfully styled and genuinely well cared for, every room tells you this home has been loved! The layout offers serious flexibility Three bedrooms on the second floor, a massive third-floor loft that functions as an entire additional level. The loft could be used as a fourth bedroom, home office, or secondary living space. The home also has a fully self-contained basement suite with its own private entrance, full kitchen, bedroom, and bathroom. The basement has just been fully renovated (2026) and a brand new furnace installed (2026) - move in and enjoy it from day one. Two full bathrooms across three levels means everyone has what they need. Out back, a private patio surrounded by mature landscaping, lush garden beds, and a fully fenced yard. The fence was replaced in 2023, a gated driveway added in 2021, and a detached shed and utility shed are already in place. In a neighbourhood where private parking is almost unheard of, the wide concrete driveway makes this property stand out before you even step inside.

Welcome to Unit 15 at 2 Vineland Ave, Hamilton! This beautiful 2-bedroom, 1-bathroom corner unit features charming hardwood floors that bring character and warmth to the sun-filled living and dining rooms. The spacious kitchen includes stainless steel appliances, tiled floors, and a breakfast area, and opens onto a cozy, private outside deck-perfect for relaxing or entertaining. One of the few units that includes parking and in-suite laundry, this home offers two equal-sized bedrooms, ideal for sharing or accommodating guests. Enjoy bright, airy interiors, modern finishes, and serene street and garden views. Residents benefit from a secure building with professional property management, on-site maintenance, and easy access to public transit, shopping, parks, and Tim Hortons Field. Ideal for first-time buyers, downsizers, or investors, this turnkey condo combines urban convenience with community charm-a truly rare find!

Welcome to 3-9 Sherman Ave South-a thoughtfully updated boutique condominium offering stylish, low-maintenance living in the heart of Hamilton. Designed with both comfort and functionality in mind, the spacious kitchen overlooks the open-concept living and dining area, creating an inviting space for everyday living, entertaining, or working from home. Two well-proportioned bedrooms provide exceptional flexibility for a guest room, office, or growing family, while custom closets and thoughtfully designed storage solutions add both style and everyday practicality throughout the unit. Enjoy your own private balcony retreat, ensuite laundry, surface parking, and the benefits of a well-managed low-rise building with affordable maintenance fees. Perfectly positioned in central Hamilton, this home offers convenient access to downtown amenities, transit routes, parks, cafes, restaurants, and major commuter connections including the QEW and GO transit. Enjoy being minutes from Gage Park, Tim Hortons Field, the Cotton Factory, independent cinemas, local markets, and Hamilton's growing arts and dining scene. A rare opportunity to enjoy practical, connected condo living with boutique charm in one of Hamilton's most accessible and evolving neighbourhoods.

This beautiful two and a half storey solid break home in a vibrant sought-after Stipley neighborhood. Close distance to schools, community center, public transit, and all amenities. Attention Investors, Renovators and Fist Time Buyers, this home is zoned TOC3 which with the right person and TLC will have lots of room for potential expansion and income. It comes with separate entrance (walk-up) to the loft on the third floor. Also comes with enclosed hot tub, detached double garage and 4 outside parking Do not loss this rare chance.

Excellent value for a legal duplex with a separate entrance into a fully finished in-law suite. This solid brick 2.5-storey home offers a rare combination of character, space, and flexibility for today's buyers. Set on a spacious corner lot with a RARE 2 Car Garage, the home features original details including wood beams and stained glass, adding charm while maintaining functionality. The layout is ideal for a variety of living arrangements. The main level provides a comfortable space for an owner-occupant, with the option to use the lower-level suite for personal use or extended family. The 3-bedroom upper unit offers a great opportunity to generate rental income to help offset monthly expenses. With 6 bedrooms and 3 full bathrooms, this property can accommodate multi-generational living or a mix of personal use and income. Key updates include a new boiler (2025) and basement waterproofing (2018). Each unit has its own owned hot water tank. The private fenced yard and detached 2-car garage add everyday convenience. Located close to highways, transit, schools, parks, and amenities, this is a versatile property offering both lifestyle and financial flexibility in a central Hamilton location.

Welcome to this solid-brick 2.5-storey detached home, nestled in the vibrant, evolving Stipley neighbourhood in North Hamilton. Offering an exceptional opportunity for affordable homeownership, this residence combines timeless character with untapped potential, making it an ideal choice for families, professionals, or investors seeking to thrive in a community bursting with possibilities. Boasting three bedrooms and two bathrooms, this well-maintained home features a functional layout that maximizes living space. New The real highlight is the third-floor loft, an unfinished blank canvas ready to be transformed into your dream retreat. The possibilities are endless, whether you envision a luxurious primary suite, a cozy home office, or additional bedrooms. The Stipley district adds to the home's appeal with its vibrant atmosphere. Enjoy the eclectic eateries along the Barton Street strip, explore nearby parks and green spaces, or cheer on your favourite team at Tim Hortons Field, steps away. With the West Harbour GO Station and downtown Hamilton just a short drive away, this location offers unparalleled convenience and connectivity. Don't miss your chance to own a piece of this dynamic neighbourhood. Book your showing today and imagine the possibilities!

Welcome to 63 Carrick Avenue! Timeless Character in a Spacious 2.5-Story Home with Loft and Detached Garage. Full of warmth and original charm, this property offers generous living space, rich character details, and a versatile layout ideal for a range of lifestyles. Featuring three spacious bedrooms plus a bright third-floor loft, this home retains its historical appeal while providing everyday functionality. The main floor showcases original hardwood flooring and detailed wood trim, with ornate pocket doors leading from the living room to the formal dining room and an elegant original staircase anchoring the space. Exposed brick accents throughout the home add unique texture and visual interest. A thoughtfully updated kitchen blends seamlessly with the home's character, while a main floor half bath adds convenience. The second level includes three bedrooms, sunroom at the rear and a full bath with clawfoot tub. The bonus loft space above offers the perfect retreat, studio, or workspace. The unfinished basement, accessible also from a separate side entrance, includes laundry and excellent potential for additional storage or workshop space. Outside, enjoy a spacious yard, detached garage, and shared driveway parking. Important infrastructure improvements include updated roof shingles and newer furnace. This home is a rare find, filled with preserved character and craftsmanship that's becoming harder to come by. A must-see for those who value quality details and timeless style! Don't miss out!!

Attention investors and opportunity seekers-welcome to this spacious 2.5-storey semi-detached home located in Hamilton's evolving Stipley neighbourhood, an area known for strong rental demand and proximity to downtown amenities. Offering over 1,500 sq ft above grade, this property features 5 bedrooms and 2 full bathrooms, providing flexible potential for multi-tenant rental, student housing, or multi-generational living. The functional layout spans three levels with generously sized bedrooms, while the home also includes forced air gas heating, central air conditioning, and an unfinished basement offering additional storage or future value-add potential. Situated minutes from Tim Hortons Field, Gage Park, Barton Street amenities, transit routes, schools, and downtown Hamilton, this centrally located property sits in a neighbourhood experiencing continued revitalization and strong tenant demand. A compelling opportunity for buyers searching for a Hamilton investment property, income property, or large home with future upside in a well-connected urban location. Immediate possession available. Buyer to verify measurements and future use potential. Some photos have been virtually staged to illustrate potential use of the space.

Sought after and rarely available home. Elegant and spacious Cape Cod Style with bonus loft level. Character home with many original features plus many updates. Basement walk up with separate entrance with partially finished in-law suite with bath,2nd kitchen, 2 bedrooms PLUS bonus loft level. Spacious 1920 Sq Ft above grade plus basement. Beautiful hardwood floors, stairs, pillars, pocket doors. Side drive with 2 parking spaces and potential to reconvert side drive and huge workshop to double car garage in backyard. Super convenient to schools, community centre, pool, Hamilton Stadium. Beautiful pink Magnolia tree in front yard. fenced backyard with deck, patio and gazebo. All sizes approximate and irregular. Don't miss this fantastic home.

Situated on the highly desirable south side of Gage Avenue, just footsteps from Gage Park, the Tropical Greenhouse, major transit routes, and the future LRT line, this property offers an exceptional location with strong long-term potential. An ideal investment opportunity, the home features a basement currently functioning as a third unit, creating additional income potential. This property is also an excellent option for first-time home buyers looking to offset mortgage and carrying costs while owning a home in a well-established south side neighbourhood. A rare opportunity to secure a versatile property in one of Hamilton's most desirable pockets.

Welcome to unit 10 at 97 Connaught Avenue South, a well-maintained 1-bedroom 1-bathroom condo offering 627 square feet of comfortable living space in a convenient Hamilton location. This condo offers excellent value and accessibility in the heart of Hamilton. This thoughtfully laid-out unit is ideal for first-time buyers, downsizers, or investors seeking low-maintenance living. The open and functional floor plan maximizes space and natural light, with a spacious living area that flows seamlessly into the kitchen and dining space. The generously sized bedroom provides a relaxing retreat with ample room for storage and furnishings. Located close to transit, shopping, Gage Park and everyday amenities. A great opportunity to own an affordable and practical condo in a well-established neighborhood. RSA.