1013 - OO Old Oakville Real Estate for Sale

Lakefront home, nestled on Old Oakville's Second Street, this residence offers a blend of timeless elegance, luxury, and unparalleled waterfront living. Completely reimagined top to bottom, showcasing an aesthetic designed for both family living and comfortable downsizing. Bathed in natural light, offering breathtaking lake views from nearly every room, you will find tranquility and grandeur from the moment you enter. Glowing hardwood flooring, custom millwork and paneling, recessed lighting, and designer finishes elevate every space.The kitchen, with panoramic lake views, features custom cabinetry, integrated top-of-the-line appliances, and an oversized island with seating for four. Quartz countertops and full-height quartz backsplash create a striking focal point, complemented by gold pendant lighting.The living room is designed for both comfort and style, featuring custom built-in cabinetry with illuminated shelving, gas fireplace, and expansive windows framing the sparkling waters of Lake Ontario. The main-floor primary suite, spacious and serene, featuring a walk-in closet. Spa-inspired ensuite with a freestanding soaker tub, glass walk-in shower, vanity, and gold fixtures and lighting. Two additional bedrooms on the upper level for family and guests, with private balcony overlooking the waterfront. Enjoy a beautifully appointed main-floor laundry room with custom cabinetry and stacked appliances. Enjoy riparian rights from a spectacular waterfront deck featuring glass railings and steps to the shoreline. Maximizing the panoramic water views, an unrivaled setting for entertaining, relaxing, and embracing Oakville's most prestigious waterfront lifestyle. Complete with a detached 2 car garage and ample private parking. Furniture by FOR living, Art by Harbour Gallery. Luxury Certified.

A rare opportunity to create a new, luxurious custom-home on one of Old Oakville's most coveted streets, set on an exceptionally private, tree-lined lot. This rarely offered design features a double-car garage and a fully finished lower level, thoughtfully crafted to deliver both elegance and functionality. Enjoy the expertise of a dedicated interior designer throughout the entire building process, ensuring every finish and detail is tailored to your vision. Features include: Curated luxury finishes throughout. Personalized interior design consultation and selection services. Optional elevator upgrade available with a three bedroom floorplan. Exceptional craftsmanship by a trusted custom builder with nearly 20 years of experience. An extraordinary opportunity to build a timeless custom home in one of Oakville's most prestigious neighbourhoods. Drawings are approved by Committee of Adjustments. Projected completion date August 2027 /Permit Process Underway

RESTORATION HARDWARE SHOW SUITE: Welcome to the crown jewel of The Randall Residences, Oakville's most prestigious address. This sun-filled Signature Penthouse Suite is the largest residence inside and out, offering approximately 3,337 sq. ft. of sophisticated living plus a 386 sq. ft. second-storey lounge with skylight and an expansive 1,327 sq. ft. southeast-facing terrace. Enter through a grand rotunda foyer with marble floors and an impressive RH chandelier, setting the tone for this exceptional home. The open-concept living and dining areas boast 12-foot ceilings, floor-to-ceiling wrap-around windows, custom Downsview cabinetry, top-of-the-line appliances, and a gas fireplace - an entertainer's dream. Restoration Hardware fixtures illuminate throughout the suite exuding an atmosphere of sophisticated refinement. The principal bedroom retreat is a haven of tranquility with a custom zebra-wood dressing room and a spa-inspired 6-piece ensuite, complete with heated marble floors, polished nickel fixtures, and a freestanding soaking tub. Two additional bedrooms each feature their own private ensuites for ultimate comfort and privacy. Ascend to the second-storey lounge, ideal for a home gym, office, or serene retreat, and step out to your private rooftop terrace designed for entertaining, featuring multiple lounging and dining zones with a gas BBQ hookup. Additional luxuries include a Crestron home automation system, integrated entertainment features, 3 parking spaces, and 2 storage lockers. Residents enjoy 24-hour concierge service in this award-winning Rosehaven Homes development, celebrated for its impeccable craftsmanship and timeless elegance. Sotto Sotto on the ground floor. Located steps from Lake Ontario, fine dining, boutique shopping, and just minutes to major highways, this penthouse represents the pinnacle of luxury living in Oakville. If you demand the best, look no further. Luxury Certified.

Nestled in the heart of downtown Oakville, this magnificent historical home offers unparalleled charm and elegance, combined with modern amenities. Spanning over 8,000 square feet, the expansive layout provides both grandeur and comfort, perfect for family living or entertaining on a grand scale. With stunning views of the sparkling waters of Lake Ontario, every room is designed to maximize the beauty of its lakeside setting. The home boasts high ceilings, intricate architectural details and walnut hardwood floors, blending timeless craftsmanship with contemporary design. The private lush yard with 104 feet of frontage is a rare gem, providing a serene outdoor oasis with mature trees and ample space for outdoor activities or quiet relaxation and complete privacy. Whether you're enjoying a morning coffee while gazing at the lake or hosting a summer gathering, the outdoor space is as inviting as the interiors. The property's prime location puts you just steps from Oakville's charming downtown, offering convenient access to world-class dining, shopping, and cultural attractions, while still providing the tranquility of lakeside living. With its rich history, extraordinary space, and unbeatable location, this is a once-in-a-lifetime opportunity to own a piece of Oakville's heritage.

Rare opportunity in coveted Orchard Beach, just steps from Lake Ontario and the waterfront trail. Set on a premium 50 x 160 ft lot, this property comes with completed architectural and engineering drawings and Committee of Adjustment approval for a proposed 3,800 sq ft residence. An exceptional offering for a buyer looking to move forward with confidence, with extensive completed work including floor plan and exterior concepts, colour renderings, arborist report, architectural drawing package, sealed roof truss package, sealed LVL layout, sealed structural engineering package, HVAC design, grading and drainage plan, soil test, and stormwater management report.The existing home was updated in 2024 with electrical improvements, a renovated bathroom, updated flooring, a new kitchen, and new appliances, offering flexibility to live in or hold the property while completing the final permit stage. Zoning and Committee of Adjustment approvals are already in place, with remaining steps in progress. Located a short stroll from downtown Oakville, the lake, and top schools, this is a rare opportunity to secure a prime property with meaningful value already created.

Nestled in Southeast Oakville, this beautifully renovated heritage home on Palmer Avenue offers timeless character, modern comfort and an exceptional lifestyle on a premium south-facing lot. Thoughtfully updated while preserving its architectural charm, the residence is filled with natural light and enjoys seamless connections to its private outdoor living spaces. The expansive south-facing backyard is a true retreat, featuring two spacious decks that provide multiple areas for entertaining, and relaxing while overlooking the mature grounds. Inside, the home blends heritage elegance with contemporary functionality. The welcoming great room is anchored by rich plank flooring and a stunning Rumford fireplace, creating a warm and sophisticated atmosphere for everyday living. The kitchen showcases clean lines and timeless design, complemented by a practical rear pantry hallway offering exceptional storage and organization. Large principal living and dining rooms provide generous space for formal entertaining while maintaining a sense of comfort and flow throughout the main level. The upper level offers four bedrooms, including a primary suite that features a Rumford fireplace, walk-in closet and a five-piece ensuite and laundry room The additional large fifth bedroom is on the main floor providing flex space for guests or home office. The finished lower level extends the living space with versatile area ideal for recreation, fitness, media or play, ensuring ample room for every stage of family life. Recent mechanical updates provide peace of mind, including a new furnace, owned hot water tank and central air conditioning. Combining heritage character, thoughtful renovations and an exceptional location in one of Oakville's most established neighbourhoods, this distinguished property offers a rare opportunity to enjoy sophisticated family living just moments from the lake, top-ranked schools, parks, shopping and the vibrant amenities of downtown Oakville.

Penthouse Perfection with Lake Ontario & Toronto Skyline Views. Welcome to Oakridge Heights, one of Oakville's most prestigious addresses, where this 1,956 square foot, 3-bedroom, 2.5-bath penthouse delivers a rare combination of size, style, and spectacular wraparound views. Renovated to exacting standards, this home offers an open, light-filled layout with south exposure over the Sixteen Mile Creek with vistas of Lake Ontario and east exposure to the glittering Toronto skyline, enjoyed from a private wraparound balcony that spans multiple living areas and offers an additional 486 square feet of space. The owners have invested heavily in this beautiful suite, upgrading it to its present stylish state since they purchased it in 2019. No expense has been spared, and the new owner will benefit from the ultimate turnkey experience, able to relax and enjoy all that this spectacular unit has to offer. For commuters, access to the Oakville GO station and the highway is a dream. A brisk 15 minute walk to downtown Oakville. Whole Foods and other gourmet shopping is just down the road. Two side by side parking spaces right by the elevator, and two lockers. Get in soon before you miss your opportunity!

Welcome to Oakridge Heights, where comfort, convenience, and lifestyle come together in the heart of Old Oakville. This bright and beautifully maintained 1+1 bedroom condo offers an ideal layout for young professionals, couples, downsizers, or anyone seeking flexible living space. The spacious primary bedroom features hardwood flooring, double closets, and semi-ensuite access to a 4-piece bath complete with a relaxing whirlpool tub. Soaring 9-foot ceilings and an open-concept living/dining create an airy, inviting atmosphere throughout. The versatile den is perfect as a home office, guest room, nursery, or creative studio-adapting effortlessly to your lifestyle. Complete with 1 parking space and 1 locker, this home offers both convenience and functionality. Commuters will love the easy access to the GO Station, QEW, and Highway 403, while weekends can be spent exploring Downtown Oakville's vibrant shops, cafés, and restaurants. Enjoy nearby trails along 16 Mile Creek and the shores of Lake Ontario, offering the perfect balance of urban convenience and outdoor living. Whether you're starting your next chapter together or looking for a stylish space to call your own, this Oakville gem is ready to welcome you home.

Steps to GO Station & Lake Ontario, Welcome to Unit 703 at 40 Old Mill Road, a beautifully upgraded 1-bedroom plus den condo available for lease in the prestigious Oakridge Heights community in South Oakville. Ideally located just a 10-minute walk from Downtown Oakville, the Lake Ontario waterfront, and the Oakville GO Station, this spacious suite offers approximately 820 square feet of refined living space with upscale finishes and tranquil views.The modern, open-concept kitchen features granite countertops, a breakfast bar, under-cabinet lighting, and a double stainless-steel sink, perfect for both everyday use and entertaining. The living and dining areas are enhanced by hardwood floors, 9-foot ceilings, crown molding, and a built-in gas fireplace set against a custom stone accent wall. Floor-to-ceiling windows and a Juliet balcony bring in natural light and provide beautiful sunset views.The large primary bedroom offers brand new laminate flooring, a walk-in closet, and a second mirrored double closet. A spacious den, currently used as a second bedroom, makes an ideal home office or private dining area. The elegant bathroom includes a Jacuzzi tub and a separate glass shower. Additional features include in-suite laundry, excellent storage, and underground parking with a private locker. This well-maintained and secure building offers 24-hour gatehouse security, an indoor swimming pool, fitness centre, renovated party room, outdoor BBQ area, and plenty of visitor parking. The location is unbeatable within walking distance to Whole Foods, Starbucks, Shoppers Drug Mart, and all the shops and restaurants in Kerr Village and Old Oakville. With quick access to the QEW, public transit, scenic parks, and top-rated schools, this condo offers a convenient and comfortable lifestyle in one of Oakville's most desirable communities. Enjoy Indoor pool and world class Building amenities

SPECTACULAR !! "One of a Kind" 2630 Sqft Unit, South/West facing Luxury Condo offering Panoramic RAVINE AND SIXTEEN MILE CREEK Views. 3 Spacious Bedrooms (plus one), 4 Baths, extra large Den with w/o Balcony overlooking Wooded Ravine. Private Sauna, Large Family Room w/Elegant Fireplace and Ravine Views. Two Private Balconies overlook Sixteen mile Creek and Wooded Ravine. A Fabulous location in Old Oakville, offers 2 Parking Spots, Double Size Locker, Walk to 'Go" Train, Shops, Restaurants, Downtown Oakville and Lake. Ideal for Couple downsizing or Family in need of a Nanny suite. Gleaming Hardwood Floors , Crown Molding, Elegant Lighting, in a unique 3 building development with security gate, sitting up on a hill overlooking nature.

Transitional Elegance in the Heart of Olde Oakville. A rare property on one of the community's most coveted streets. Experience refined living in this exceptional residence- set on a triple lot over 1/2 acres with an impressive 154.73 ft frontage, curated for those who value privacy, design and indoor-outdoor living at its finest. Beautifully reimagined in 2024, the main level showcases a sophisticated blend of transitional elegance and casual upscale comfort, perfect for both everyday living and effortless entertaining. A Main Floor Redesigned for Modern Luxury. Step inside to wide-plank oak hardwood floors, luxurious finishes, and stunning sightlines to the property's park-like grounds. The brand-new designer kitchen is a true showpiece, featuring: Main kitchen+ second "messy kitchen" for concealed prep, storage, and small appliances. Silk granite farmhouse sink with brushed gold gooseneck faucet and gold hardware accents throughout- Oversized picture window overlooking the gardens. Square island with integrated fridge/freezer drawers. Quartz countertops & full-height backsplash in both kitchens. Built-in wine/beverage station. Dedicated coffee bar. A walk-out from the dining room and a large picture window open to views of the serene screened-in sun porch ,creating a seamless flow for indoor-outdoor enjoyment. The magnificent great room features dramatic cathedral ceilings, a stone wood-burning fireplace (forced-air assist) with aged beam mantel, and wiring/rough-ins for a full theatre- quality sound system. A second walk-out continues to the sun porch- offering year-round enjoyment framed by nature. Flexible living spaces: Third floor loft/suite ideal for guests, teens, studio oroffice.4+1 bedrooms, 4 bathrooms, and over 5200 sq ft of total finished living space. Finished basement with heated floors in media room (or current gym). Dust-free heat system with individually controlled room zones. **Remarks continued in Attachments

Welcome to one of Downtown Oakville's most celebrated residential addresses, imagined and brought to life by an exceptional local team, the internationally acclaimed luxury designer whose signature detailing elevates this landmark building into a work of art. Together, they crafted a boutique residence that seamlessly blends sophistication, exclusivity, and enduring elegance. This expansive suite features grand principal rooms, soaring ceiling heights, and refined architectural proportions throughout. The Great Room and adjoining Kitchen/Dining Room provide an impressive setting for both relaxed living and elegant entertaining, while the formal Foyer and circular entry gallery create a memorable sense of arrival. The private primary wing offers a gracious Master Bedroom with Juliet balcony, ensuite bathroom, with walk through dressing room, delivering a true luxury retreat. A second bedroom is perfect for guests or extended family and is thoughtfully preceded by its own private vestibule, enhancing comfort and privacy. Additional conveniences include a separate Laundry Room, dedicated Storage Room, and a Powder Room that complements the home's generous flow. The building also features the renowned Sotto Sotto restaurant on the main level - a testament to the calibre of the address and a unique lifestyle benefit for residents. Steps to the lake, marina, shops, cafés, and cultural venues, this residence offers a rare blend of boutique luxury and walkable urban convenience. A distinguished opportunity to live in one of Oakville's landmark buildings.

Welcome to Oakridge Heights in coveted Old Oakville, where bespoke design, elevated finishes, and effortless convenience come together in a truly refined condominium residence. Thoughtfully renovated with a discerning eye, this 2 bedroom + den, 2 bathroom suite offers a sophisticated sense of flow, with wide-plank flooring, expansive floor-to-ceiling windows, and sweeping treetop and lake views that bring a quiet elegance to every principal space. The open-concept living and dining area is warm, stylish, and inviting, featuring custom lighting, balcony access, and a seamless connection to the designer kitchen. Finished with dramatic stone countertops and backsplash, sleek flat-panel cabinetry, stainless steel appliances, built-in oven and microwave, and a waterfall-style peninsula, the kitchen makes an impressive statement. The suite also features a well-designed home office with custom built-ins, a spacious primary bedroom with panoramic views, luxurious 5 pc ensuite beautifully updated bathrooms with glass showers, designer tile, gold and black accents. A well-appointed second bedroom, stylish 3-piece bathroom, dedicated office with French door and built-in shelving/desk, plus in-suite laundry with stackable washer/dryer and laundry sink add everyday function and comfort. Residents enjoy outstanding building amenities, including an indoor pool, gym, hobby room, and party space. Ideally positioned just steps to the GO/VIA Station, Whole Foods, and Olde Oakville Market Place, and only a short stroll to downtown Oakville's boutiques, restaurants, lakefront, parks, and trails, this exceptional residence offers a polished lifestyle with easy highway access and a convenient commute to downtown Toronto. Thoughtfully finished from top to bottom, this condo blends comfort, style, storage, and incredible views in one sophisticated package.

A complete renovation & restoration was undertaken to this circa 1890 home. Exceptional attention to detail created a functional layout enhanced by superb finishings. An inviting front covered porch draws you into this 4 + 1 bdrm, 3 bath home in the heart of Old Oakville. The spacious front Foyer is finished with double closet & Powder Room with the added bonus of a separate side entrance from the driveway into functional mudroom with built-in cupboards. A private home Office with custom built-in bookcases is located at the front of the home. Sunshine from the south facing windows floods the open concept Family Room with gas fireplace, Dining Room, Kitchen & Breakfast Room with sunlight. The renovated Kitchen with built-in appliances, centre island & separate Breakfast Room can seat your family comfortably. Or enjoy more formal entertaining in the Dining Room adjacent to the Family Room. The Breakfast Room, enhanced with corner windows o/l the garden, has a walk-out to covered BBQ area, flagstone patio & lush backyard.The Primary Bedroom is enhanced with 12 ft cathedral ceilings, his & hers walk-in closets & 5 piece ensuite bathroom. Three other bedrooms & 5 pc family bathroom, complete the 2nd level.The fully finished lower level has a cozy Recreation Room with B-I entertainment unit & wall of south facing windows offering ample natural light. A separate Exercise Room with built-in double desk could function as Playroom or 5th Bedroom. Ample storage under the stairs & in the Utility Room plus a spacious Laundry Room are bonus spaces. The private drive allows for 3 car parking. Enjoy the landscaped front & rear gardens with sprinkler system, new fence & patio. Or sit with morning coffee on the front porch & watch the world wake up. Situated in a much desired pocket of Olde Oakville w/ close proximity to Oakville GO Station, top tier public, private & Catholic schools, parks, shops & new Community Center. A opportunity not to be missed!

Welcome to Oakridge Heights - right in the heart of Oakville and perfectly placed just minutes from Highway 403 and the Oakville GO. Translation? Getting around is easy, if you need to go somewhere. But we think you'll feel right at home here, and won't need to leave. This bright, corner 2-bed, 2-bath unit has that airy, open feel you want, plus an electric fireplace for those cold, moody nights and a private balcony for the sunny ones. Best of both worlds. The primary bedroom comes with a full four-piece ensuite and a proper walk-in closet (not one of those "technically a closet" situations). The second bedroom pulls its weight too, with its own three-piece cheater ensuite - great for guests, roommates, or a home office setup. As for amenities? You're covered. Indoor pool, gym, sauna, billiards room, party space - it's all here. There's even visitor parking on site, so hosting doesn't turn into a logistical nightmare. And you'll never have to start a cold engine with your own underground parking space. Set in one of Oakville's most sought-after communities, you're close to great shopping, dining, parks, waterfront trails, and easy transit into Toronto. Basically, it's comfortable, convenient, and checks all the boxes - without trying too hard. Bonus - now offering $5000.00 towards new appliances.

Welcome to 135 Deane Ave, where modern comfort meets the charm of Kerr Village. Just a short stroll from local cafes, boutique shops, and the shores of Lake Ontario, this beautifully renovated bungalow invites you to slow down and feel at home. Step into the sun-filled four-season sunroom, wrapped in windows and natural light - the perfect spot for morning coffee as the neighbourhood comes to life. From there, the home opens into a warm and welcoming living and dining space, anchored by an exposed brick fireplace that tells its own story of character and comfort. At the back of the home, the thoughtfully updated kitchen awaits, complete with quartz countertops, crisp white subway tile, and stainless steel appliances. Whether you're preparing a quiet weeknight dinner or hosting friends, this space flows effortlessly onto a spacious deck overlooking a private, tree-lined backyard - ideal for summer evenings under the stars. Two generous bedrooms and a sleek three-piece bath complete the main level, while a mudroom offers practical everyday convenience and access to the lower level. Downstairs, the fully finished basement expands the possibilities, featuring a large recreation room, two additional bedrooms, a full bath, and a separate entrance with laundry and kitchen rough-ins - ready to be converted into a self-contained unit for guests or extended family. With a detached garage and ample driveway parking, this home is more than a place to live - it's a place to belong.

Nestled Just Moments From The Shores Of Lake Ontario In One Of Oakville's Most Coveted Neighbourhoods, 298 Douglas Avenue Offers The Perfect Blend Of Lakeside Living And Refined Family Comfort. This Beautifully Renovated 4+1 Bedroom, 3 Bathroom Residence Has Been Thoughtfully Redesigned From Top To Bottom, Combining Timeless Character With Elevated Modern Finishes. The Main Floor Features Rich Hardwood Flooring, Elegant Mouldings, Pot Lights, And Expansive Windows That Fill The Home With Natural Light. The Custom Chef's Kitchen Is A True Showpiece With Quartz Countertops, Stainless Steel Appliances, Designer Lighting, A Large Centre Island With Seating, And Seamless Access To The Backyard, Ideal For Entertaining. The Inviting Living Spaces Provide Warmth And Sophistication, Including A Cozy Fireplace And Effortless Flow For Everyday Living. Upstairs, 4 Spacious Bedrooms Offer Flexibility For Growing Families, Highlighted By A Stunning Primary Retreat With A Walk In Closet And Beautifully Updated Ensuite. The Additional Bedrooms Are Bright, Generous In Size, And Finished With Tasteful Detailing And Neutral Tones. The Fully Finished Lower Level Expands Your Living Space With A Large Recreation Room, Additional Bedroom, And Versatile Space Perfect For A Home Gym, Media Room, Or Guest Suite. Enjoy The Best Of Oakville Living Just Steps To Waterfront Trails, Parks, And Minutes To Vibrant Downtown Shops, Restaurants, And Top Rated Schools.

Nestled behind private gates on one of Oakville's most coveted "Street of Dreams," this exceptional estate sits on a spectacular 100 x 225 ft lot and offers over 7,500 sq ft of luxurious finished living space. Surrounded by manicured gardens and mature trees, the home blends timeless architecture with sophisticated, on-trend finishes and commanding curb appeal. A grand double-height foyer introduces an elegant interior designed for refined living and effortless entertaining. The main level features a chef-inspired kitchen with custom cabinetry, seamlessly open to a spacious family room. A private office, formal living room, piano lounge, and a stunning three-season Muskoka room extend the living space into the tranquil backyard. Upstairs, the luxurious principal retreat showcases a sleek linear gas fireplace, dual spa-inspired ensuites, separate walk-in closets, and a boutique-style dressing room, with a private balcony overlooking the Muskoka-like setting. Three additional bedrooms each offer private ensuites and generous custom closets for ultimate comfort and privacy. The fully finished lower level-accessible by both the main staircase and a unique main-floor slide-offers expansive recreation and games areas, a theatre, gym/fifth bedroom, full bath, and abundant storage. Two laundry rooms provide exceptional convenience for modern family living.Since 2025, the owner has invested significantly in premium upgrades, including enhancements to the kitchen cabinetry, custom closet built-ins, lower-level laundry room, fireplaces in the living and family rooms, window treatments, appliances, primary dressing area, and multiple bathrooms-further elevating the home's quality and turnkey appeal. A rare opportunity to own a gated estate of scale, elegance, and enduring value in prestigious S.E Oakville.

Set on a beautiful 100' x 136' lot in Prestigious Olde Oakville, this exceptional family home offers 4,752 sq ft of total living space of refined timeless design & impeccable craftsmanship all just a short stroll to Downtown Oakville, the lake, and some of Oakville's most sought-after schools. classic brick exterior, solid wood front door, and towering mature trees create a warm and elegant first impression. This home exudes an inviting aesthetic that feels made for family living and effortless entertaining.The kitchen features top-of-the-line appliances, two Miele dishwashers, dual walk-in pantries, water filtration system, three sinks including a coffee station/wet bar, and an oversized island that comfortably gathers family and friends for everything from casual breakfasts to holiday celebrations. The adjoining dining room is anchored by a charming wood-burning fireplace, while the spacious family room, also with a wood-burning fireplace, opens seamlessly to the private backyard, creating an ideal indoor-outdoor connection. Enjoy sunny south exposure, a sparkling saltwater swimming pool(liner/pump/heater 2024), Maibec deck with sleek glass railings, and a beautiful stone patio ideal for summer dining and lounging. Despite the impressive outdoor amenities, there remains abundant green space for children to play and the whole family to gather. The functional mudroom and sophisticated main floor den complete the thoughtfully designed main level. The second floor is equally impressive, highlighted by a luxurious primary retreat with its own gas fireplace, walk-in closet, custom built-in storage, and five-piece ensuite with heated flooring. Three additional generously sized bedrooms and a beautifully appointed full bathroom provide ample space for a growing family. Finished to the highest standards, this extraordinary residence offers the rare combination of timeless style, family-focused functionality, and an unbeatable Olde Oakville location. Welcome Home.

Located in coveted Old Oakville, this charming 3-bedroom, 2-bath bungalow sits on a mature 50 x 142 ft treed lot. Just steps to the GO Train and Whole Foods plaza, and a short walk to downtown Oakville restaurants, shops, Lake Ontario. Close to top-rated schools. The renovated main level features a two-tone kitchen with stainless steel appliances, custom penny round and ceramic backsplash, high-gloss cabinetry, pot lights, hardwood flooring, bright living and dining rooms, and a renovated 5-piece main floor bath. The lower level offers a spacious family room with oversized windows and excellent additional living space. Enjoy a large fully fenced backyard, poured concrete driveway with carport parking for 4+ cars, and a convenient separate side entrance. Minutes to GO/VIA, QEW, downtown Oakville, shops, restaurants, and the lake. Please note that some of the backyard photos have been virtually staged for illustration purposes.

Walk to downtown Oakville from this 2024 custom-built residence, third house from Lake Ontario on a 65 x 158 lot south of Lakeshore. A rare new-construction opportunity in Old Oakville's most walkable pocket: minutes walk to the harbour, the Oakville Club, Lakeshore Road shops and restaurants, and waterfront trails.4,362 sqft above grade plus 2,468 sqft finished lower level (6,830 sqft total). Net Zero Ready, Tarion warranty.Designed by Chatsworth Fine Homes with architect John Willmott and designer Jane Lockhart. Herringbone white oak floors, panel mouldings throughout, and a formal dining room with dual chandeliers. The chef's kitchen is equipped with Miele appliances including built-in coffee system plumbed to the waterline, dual Miele ovens (standard & steam), SubZero refrigeration, and a SubZero wine and beverage column. Opens to a great room anchored by a linear fireplace, custom built-ins, and expansive rear-yard windows. Servery, custom mudroom with exterior access, and private main-floor office.The primary suite is a quiet retreat with spa-inspired ensuite: freestanding tub, oversized shower, double vanity, and dressing-island walk-in closet. Secondary bedrooms each with private ensuite. Heated floors and curbless showers throughout. Upper-level laundry with 2 washer/dryer sets.The lower level (10' ceilings) is built for entertaining: rec room with custom bar and kitchenette, additional bedroom, gym, theatre room, full bath, and walk-up access to the rear yard.West-facing rear yard with covered heated lounge, in-ground pool with waterfall, and hot tub: built for afternoon sun and long summer evenings. Heated driveway, partial lake views, radiant in-floor heating, Crestron home automation, Tesla charger rough-in, and standby generator.A new-construction home in walkable Old Oakville, steps from the lake. Morning coffee on the porch, lunch on Lakeshore Road, dinner by the pool. Inventory like this rarely comes to market in this pocket.LUXURY CERTIFIED.

Downtown Oakville at your doorstep! Impeccably maintained 2-bedroom, 2-bathroom condo combines comfort and convenience with a rare private balcony, all just moments from Oakville's renowned dining scene, boutique shopping, and picturesque waterfront trails. Offering 975 sq. ft. of thoughtfully designed living space, this unit features a functional split bedroom layout, two walk-in closets, upgraded light fixtures and a bright, carpet-free open-concept design. The kitchen is both stylish and functional, featuring matte black tile flooring, white cabinetry & countertops, and three full size appliances including a new dishwasher. The open-concept layout makes everyday living and entertaining effortless. Kitchen is ideally connected to the great room, plus large sunny sliding glass windows to the private balcony!The spacious primary bedroom includes a walk-in closet, a 4-piece ensuite with a glass-enclosed shower and direct access to your private balcony-perfect for morning coffee or evening relaxation. The second bedroom is equally generous, also featuring a walk-in closet. The main 4-piece bathroom offers tile flooring and a glass-enclosed shower. Insuite laundry room with additional storage & cabinets adds to the convenience. BRAND NEW furnace (to be installed this fall 2026)!Complete with 1 underground parking space and 1 locker, this home checks all the boxes. This well managed building is a boutique style low rise condominium that has been beautifully updated and features a party room, visitor parking and landscaped courtyard. Located in the heart of quaint Downtown Oakville, just steps to boutiques, bakeries, cafés, Oakville Centre for performing arts centre, renowned restaurants. Your Downtown Oakville lifestyle starts here!

Exceptional opportunity to own a beautifully updated 5-bedroom, 4-bath executive home on a rare 50 ft*350 ft lot in the heart of prestigious Old Oakville. Nestled on a quiet, tree-lined street, this over 4,000 sq ft residence features a stunning great room with 18' vaulted ceiling and French doors opening to a huge two-level deck overlooking a private Muskoka-style backyard oasis, offering the perfect blend of cottage-style living and city living comfort. The bright open-concept kitchen with skylights and stainless steel appliances is ideal for entertaining, while the main-floor in-law/guest suite with private ensuite provides flexibility for multi-generational families. Freshly painted, carpet-free, and filled with natural light, the home includes new LED lighting, two furnaces, Heatpump and AC. With two separate basement entrances and a walk-out lower level, there's exceptional potential for a private suite, home office, or future expansion. Walking distance to the new community centre, lakeshore, top-rated schools, parks, and transit, and just minutes to the QEW, this property offers the perfect balance of luxury, privacy, and convenience - a rare chance to live, invest, or build your dream home in one of Oakville's most prestigious neighborhoods.

Carefree living reaches its finest expression in this spectacular, completely renovated 2-bdrm,2-bath residence in one of downtown Oakville's most coveted lakefront addresses. Spanning 1,863 sq ft,Suite303 offers a rare south/southwest exposure with captivating views toward the Oakville Club,marina & Lake Ontario.Best enjoyed from three private terraces and an extraordinary glass-enclosed sunroom.Located on the 3rd floor but considered the ground floor due to the slope of the land,this Suite gives you easy step-out access to the roadEvery detail of this Suite has been renovated without compromise using high quality finishes.Heated floors run thru/out,ceilings raised in the Kitchen,Dining Room & Living Room,and custom Misani cabinetry brings a refined,tailored finish to the open-concept interiors.The kitchen is a true culinary showpiece,appointed with built-in Wolf/SubZero appliances and designed for effortless entertaining complete with breakfast counter bar and walk out to enclosed terrace.Open concept Living Room & Dining is perfect for entertaining or just relaxing to watch TV.The fireplace and built-in cabinetry add warmth and a place to display collectibles.The oversized primary retreat features terrace access, bespoke closet cabinetry,and a luxurious 5-pc ensuite w/heated floors.The second bedroom also opens to a terrace and enjoys a semi-ensuite 3-pc bath.The sunroom is a standout sanctuary-bright,serene & perfectly suited for morning coffee or an evening unwind.A large laundry room w/ sink and addt'l storage adds practicality, while two side-by-side parking spaces (no pillar between) and an oversized locker complete the offering.Residents enjoy updated amenities incl 24 hour concierge,guest suites,fitness center, newly renovated party room & pool area.Steps to the lake,charming downtown Oakville of boutique shopping with acclaimed dining.This Suite with its quality finishes & multiple walk outs with spectacular views gives the condo life you dream of!

15 Chartwell Rd offers a lifestyle of unparalleled luxury. Drive through the gates & discover the grandeur of this palatial estate. South of Lakeshore,1 door from the lake on a HALF ACRE LOT. Painstakingly curated, the contemporary limestone masterpiece you've been waiting for. Solid iron doors lead to a grand foyer revealing the opulent book matched marble floors. Floor to ceiling wdws & French doors flood the house with light. Cascading waterfalls fank the hall.The Dining Room has statement lighting & servery making hosting a breeze. Soaring 18-ft ceilings & a grand gas f/p are focal points of the Great Room,w/captivating views of the resort style yard. Experience culinary excellence in the black lacquer& glass kitchen by NEFF that features top of the line appliances & a B/I coffee machine & butlers pantry. The intimate Living Room with f/p is the ideal retreat. A main floor office w/built-in cabinetry.2 powder & 2 laundry rooms. The backyard oasis has a gunite pool, waterfalls, fire bowls, covered terrace & outdoor kitchen & f/p.The pool house has a change room,3-pc bath & servery. Towering trees surround the home & are positioned to create privacy. A stone driveway,circular fountain & lush gardens create a breathtaking landscape.Floating marble stairs divide the 3 levels of this home or, you can take the elevator. Skylights make the upstairs airy & bright.The principal suite has nearly 13-ft ceilings, an exquisite 6-piece ensuite & 2 W/I closets. A private balcony overlooks the yard.3 add'l bdrms have 10-ft ceilings,private ensuites & W/I closets. The LL caters to all family members. A 5th bdrm/ensuite makes an ideal guest suite.Gym,R/I Golf Simulator,home theatre,Wine Cellar& doggie Spa. The Games & Rec Rooms have a 2nd kitchen & W/O.Heated garage,baths &LL flrs.Automation. Designed by Bill Hicks & features the artistic creativity of the KT Design Group. Located on Oakville's Street of Dreams, this is an iconic living space designed to impress! LUXURY CERTIFIED

LIVE NOW, BUILD LATER. Ideal for end-users and investors alike, this beautifully updated 3+1 bedroom home is located just minutes from the lake and Downtown Oakville. Set on a 62.8 x 110 ft lot, the home offers a warm, well-designed layout with bright principal rooms, a separate dining area, and a stylish eat-in kitchen. The entire home has been thoughtfully improved throughout, creating a clean, move-in ready space that feels comfortable and inviting. Upstairs features three well-sized bedrooms and a fully updated bath.The fully finished basement includes a fourth bedroom and separate walk-up entrance, offering excellent potential for extended family living, rental income, or a private workspace. Enjoy a private, fully fenced backyard, all within walking distance to the lake, parks, shops, and restaurants that define Old Oakville living.Zoned RL4-0, permitting 35% lot coverage and currently allowing up to 4 units (buyer to verify). Situated within a heritage area with precedent for redevelopment and intensification nearby. Potential land assembly with neighbouring property (~124 ft combined frontage). Future possibilities may include luxury townhomes, boutique condos, or rental units, subject to approvals.

Welcome to 417 Union Street, an exceptional modern home nestled in the heart of prestigious Old Oakville. Completed in 2023, this one-of-a-kind residence blends modern farmhouse inspiration with refined contemporary and traditional design elements, creating a home that is both striking and timeless. The modern farmhouse exterior showcases clean lines, black-framed windows, and a harmonious mix of materials, complemented by a covered porch, professionally landscaped front and back yards, and a stone six-car driveway. The backyard offers a private retreat with a deck, stone patio, and custom garden shed. Inside, the home is filled with natural light and defined by a modern, sleek interior. Wide-plank engineered hardwood flooring, custom ceilings with integrated LED lighting, and large-format matte tiles elevate the main living areas. The chef-inspired kitchen features quartz countertops and backsplash, an oversized centre island, built-in Bosch appliances, and a convenient adjoining servery. A tiered maple staircase with glass railings leads to the upper level, where skylights continue the home's bright and airy feel. The expansive primary suite spans over 700 square feet and offers two walk-in closets and a luxurious five-piece ensuite with double vanity, freestanding tub, and glass-enclosed rainfall shower. Three additional bedrooms each include their own custom three-piece ensuite with modern walk-in showers. The fully finished lower level adds outstanding versatility with a second kitchen, large recreation room, two additional bedrooms with ensuites, and a powder room. Additional highlights include an elevator servicing all three levels, 10-ft ceilings on the main and lower levels, pot lights, blackout blinds, built-in speakers, and a security system. Ideally located minutes from Lake Ontario, parks, trails, Oakville GO, the QEW, and top-ranked schools including Appleby College, this home delivers modern luxury, thoughtful design, and an exceptional lifestyle.

Welcome to this beautifully updated 2-bedroom, 2-bath, with parking condo right on Oakville's renowned Town Square. With tasteful finishes and a timeless design, this residence offers elegant living in one of the most walkable and coveted locations in town. Enjoy sunset views from your covered terrace, steps from boutique shops, acclaimed dining, the lake, marina, and the Oakville Centre for the Performing Arts. The building itself has been fully refreshed inside, blending classic sophistication with modern comfort. Includes one parking space, with guest parking available. A rare opportunity to live in the heart of Old Oakville without the million-dollar price tag.

Set in the heart of Old Oakville on a generous, tree-lined lot, this distinguished red brick residence blends timeless architecture with thoughtful modern updates. Featuring 3+1 bedrooms and 5 bathrooms, each upper bedroom offers its own private ensuite, delivering a rare level of comfort and privacy. The main level is defined by rich character and natural flow, with original wood detailing, oak hardwood flooring, and a gradual-rise staircase anchoring the space. The living room is both refined and inviting, centered around a gas fireplace with custom paneling, while the formal dining room provides an elegant setting for entertaining. At the heart of the home, the kitchen features Blue Lagos soapstone countertops, custom cabinetry, a large island with integrated cooktop, and dual dishwashers. A built-in wet bar enhances functionality, while large windows connect the space to the surrounding greenery. A standout feature is the carriage house-inspired bar area with original doors offering a unique blend of heritage charm and everyday use. A sunroom with terracotta tile flooring provides a bright, relaxed retreat with direct access to the outdoors. The finished lower level extends the living space with a recreation room featuring a second gas fireplace, additional living areas, a bedroom, full bathroom, and dedicated wine display. Complete with a detached two-car garage, mature landscaping, and located just steps to the shops, restaurants, and waterfront of Old Oakville, this is a rare opportunity to own a character home in one of the area's most sought-after neighbourhoods. Luxury Certified.

IMPROVED OPPORTUNITY! Discover this charming family home nestled in the heart of Old Oakville, one of the area's most desirable neighbourhoods. Meticulously maintained 1.5-storey residence on a beautifully landscaped 50' x 141.8' lot, tucked away on a quiet, tree-lined cul-de-sac. Surrounded by inviting covered porches and decks, a peaceful setting to enjoy nature while remaining close to all amenities. Originally purchased over 40 years ago as a quaint cottage and thoughtfully renovated in 1992, features generously sized principal rooms, including a sunken, oversized family room. This inviting space showcases a reclaimed brick, wood-burning fireplace with a barn board mantel, along with a matching bar and sliding doors that open to a Muskoka-inspired backyard.Expansive rear-facing windows flood the home with natural light and lead to a spacious 36'4" x 14'6" deck-perfect for entertaining or relaxing year-round. With over 2,050 sq. ft. of above-grade living space, this home seamlessly blends timeless character with modern comfort. The home offers 3+1 well-appointed bedrooms, 4 bathrooms, and a versatile living room currently used as a formal dining space. The finished basement provides additional flexibility for growing families. The main floor includes a bedroom that can also serve as a home office or den, along with an updated bathroom. Hardwood flooring and ceramic tiles enhance the main level, while the spacious kitchen features abundant cabinetry, a large pantry, and a double sink. Additional highlights include a separate main floor laundry room with a utility sink, folding counter, and ample storage. At the rear of the property, two detached outbuildings, with electricity offer excellent potential for a workshop, studio, or garden storage. This property offers endless possibilities for renovation or addition. Just minutes from top-ranked public and private schools, Downtown Oakville, Whole Foods, LCBO, charming shops, the lakefront, parks, walk to GO transit

TWO PARKING SPACES! This 1-bedroom + den condo offers about 800 sq ft of well-designed space in a location that's hard to beat-just steps from the GO Station. It's a great option for anyone who wants an easy commute without giving up comfort at home. The galley-style kitchen is clean and practical, with granite counters, stainless steel appliances, and extra built-in storage. The living and dining area is open and bright, with floor-to-ceiling windows and clear views out over Oakville. The bedroom is a solid size with a walk-in closet, and the den gives you flexibility-home office, reading spot, or just some extra room to tuck things away. The building has everything you'd expect: indoor pool, gym, party room, sauna, plus secure entry with a 24-hour gatehouse. You also get two underground parking spaces, which is a nice bonus. You're within walking distance to the GO, Whole Foods, LCBO, and not far from downtown Oakville and the waterfront. Whether you're looking for something low-maintenance, an investment, or a place to downsize into, this one checks a lot of boxes.

Private, elevated, and unlike anything else in Old Oakville - A true four-season outdoor retreat, your private playground for the outdoor enthusiast-where each day invites skating, paddling, kayaking, hiking, fishing, boating and cross-country skiing, alongside wildlife watching and refined al fresco dining, embracing nature in all its seasons. This lofted waterfront residence commands breathtaking views and unmatched privacy along the tranquil 16 Mile Creek. A testament to craftsmanship and design, this waterfront retreat boasts exclusive riparian rights and a private dock, inviting you to embrace the beauty of Oakville's scenic waterways year-round. .A meticulous 2016 renovation elevated this residence with rich hand-scraped oak floors, solid wood doors, custom millwork, and elegant tray ceilings. The sprawling 1,700 sq. ft. premium Wolf PVC deck includes a hot tub oasis, integrated fire table, and motorized awnings, leading to a dock with a kayak launch, swim ladder, and floating dock. Glass-encased staircases on helical piers deliver striking architectural presence and unbroken sight lines to the creek. Inside, sophistication defines every detail. Floor-to-ceiling windows in the living room frame stunning ravine views and dramatic sunsets, while a gas fireplace with a live-edge mantel adds warmth. The chef's kitchen impresses with a leathered Taj Mahal quartzite island, Wolf and Miele appliances, and an integrated Sub-Zero fridge. Heated floors run throughout, including in the spa-like primary ensuite with marble floors, a rain shower, and double vanity. The lower level offers a linear fireplace, built-in bar, and walkout to the deck. A concrete-lined storage room playfully known as the Bomb Shelter provides additional functionality. Blending natural beauty, refined design, and year-round outdoor living, this one-of-a-kind property is just steps to downtown Oakville and the GO Train offering luxury, serenity, and convenience in equal measure.

This completely renovated contemporary residence represents the pinnacle of modern design and sophisticated living in one of Oakville's most desirable locations of Old Oakville.Every detail of this 4 Bedroom | 4+1 Bathrooms | 4,819 Sq Ft Finished Living Space has been meticulously reimagined to deliver an unparalleled standard of quality and craftsmanship.The highly functional main floor plan centers around an exceptionally sleek kitchen open to the Great Room with gas fireplace and walk out to the resort style backyard and pool.The kitchen is outfitted with luxury high-end appliances, an oversized island seating eight, and an additional peninsula for casual entertaining in the bar area.Adjacent to the kitchen, is a walk in pantry with an additional dishwasher and fridge. Not to be missed is the impressive temperature-controlled wine room accommodates approx 1,000 bottles-a striking feature for the discerning entertainer.A versatile family room/main floor bedroom with ensuite which can be used as a principal bedroom or guest suite, laundry room, walk-in main closet for storage and access to oversized double car garage.The 2nd level principal suite is a private sanctuary featuring juliette balcony, gas fireplace, two walk-in closets and a spa-inspired ensuite with heated floors, walk-in shower, and a standalone soaking tub.Two additional spacious bedrooms each with their own ensuites complete the level. Not to be missed is the finished lower level room with added storage in the pantry and crawl space area. The backyard is an entertainer's paradise, showcasing a saltwater pool, two expansive patio areas, two gazebos with a gas fire table, and premium Dutch-imported artificial turf that remains lush year-round with zero maintenance.Ideally situated steps from Whole Foods Market, Oakville GO Train, for seamless transit connectivity,and the Oakville Trafalgar Community Centre this extraordinary property offers both refined luxury and everyday convenience.LUXURY CERTIFIED

Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. A selection of distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. Impressive detached w/47-foot frontage, 2836 sqft of finished space w/an additional 1,000+ sqft(approx) in the lower level left untouched. Curated:4 beds + 3.5 baths. Utility wing from garage, chef's kitchen w/w/in pantry, expansive breakfast+great room. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment.

Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. A selection of distinct models, each magnificently crafted, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and contemporary gathering spaces. A true exhibit of flawless design and impeccable taste. The Arlington; 3,677 sqft of finished space, 3 beds, 3 full baths + 2 half baths, this model includes 622 FIN sqft in the LL. A few optional layouts ground + upper. Garage w/interior access to mudroom, ground floor laundry, walk-in closet, full bath + family room w/French door to rear yard. A private elevator services all levels. Quality finishes are evident; with 10 ceilings on the main, 9 on the ground & upper levels. Large glazing throughout, glass sliders to both rear terraces & front terrace. Quality millwork & flooring choices. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Chefs kitchen w/top appliances, dedicated breakfast, overlooking great room. Primary retreat impresses with large dressing, private terrace & spa bath. No detail or comfort will be overlooked, with high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Expansive outdoor spaces; three terraces & a full rear yard. Perfectly positioned within a canopy of century old trees, a stones throw to the state-of-the-art Oakville Trafalgar Community Centre and a short walk to Oakvilles downtown core, harbour and lakeside parks. This is a landmark exclusive development in one of Canadas most exclusive communities. Only a handful of townhomes left. Full Tarion warranty. Occupation estimated summer 2026.

Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection is an extension of the inaugural development with an exclusive collection of seven homes located on Douglas Avenue. Distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. "The Chatsworth"; detached home with 48-foot frontage, between 3,188-3,204sf finished space w/an additional 1,000+sf (approx)in the lower level & 4beds & 3.5 baths. Utility wing from garage, chef's kitchen w/w/in pantry+ generous breakfast, expansive great room overlooking LL walk-up. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment.

Gorgeous Family Home on Prestigious Chartwell Road in Old OakvilleNestled on a prime 0.29-acre west-facing lot backing onto serene woodlands, this immaculate 4+2 bedroom residence is situated on the coveted "Street of Dreams" Chartwell Road in the heart of highly sought-after Old Oakville. Offering endless potential, this exceptional property is ideal for families looking to move in, renovate, or build their custom dream home in a prestigious neighbourhood.The beautifully maintained home features gleaming hardwood floors, spacious living, dining, family principal rooms, and a thoughtfully updated patio and deck perfect for outdoor entertaining. The finished basement, with a private separate entrance, includes a 2-bedroom in-law suite complete with a full kitchen and bathroom, offering incredible flexibility for multigenerational living or rental income.Enjoy unparalleled convenience with a short walk to Whole Foods, Longos, charming local restaurants, top-rated schools, and minutes to the GO Station and QEW. This is a rare opportunity to own a slice of Oakville's most desirable enclave where lifestyle, luxury, and location meet.

Perfect for downsizers and long-time Oakville residents seeking peaceful, low-maintenance living in the heart of historic Old Oakville. This beautifully updated 2-bedroom residence in the boutique Mayfair Co-operative offers a bright, welcoming home just steps from one of Oakville's most beloved neighbourhoods. Located on a quiet, tree-lined street, the home is within walking distance to downtown Oakville's shops and restaurants, the lakefront, Oakville GO Station, and the new Oakville Trafalgar Community Centre, offering exceptional walkability and convenient transit access. Inside, you'll find a thoughtfully renovated kitchen with stainless steel appliances, under-cabinet lighting, and modern finishes, an updated bathroom, durable pale wood-grain flooring throughout, and newer energy-efficient windows. Large windows provide natural light and overlook the building's beautifully maintained perennial gardens, creating a calm and inviting atmosphere. The boutique Mayfair Co-operative offers a quiet, owner-occupied community where neighbours take pride in their building and enjoy a peaceful environment. Pride of ownership fosters a strong sense of community while helping maintain long-term value. Monthly fees include property taxes, heat, water, and parking, providing predictable and simplified ownership costs. The building also offers a dedicated parking space, storage locker, on-site laundry, and optional garage rental. A wonderful opportunity for those who love Oakville and want to remain close to the community, friends, and lifestyle they cherish. Co-op Information Package available outlining ownership structure, financing through DUCA, and board approval process. Co-operative ownership requires a minimum 30% down payment.

Nestled south of Lakeshore in the heart of Old Oakvilles historic district, this beautifully restored Georgian-style home, designed by Gren Weis, blends timeless character with modern updates. Steps from the lake, river, and vibrant Downtown, it offers an unmatched lifestyle location.The home boasts exceptional curb appeal with a flagstone path leading to a spacious foyer. Sun-filled interiors feature Farrow & Ball paint, new hardwood on the main level, preserved fir upstairs, smooth ceilings, and recessed LED lighting.The updated kitchen includes a large island, built-in appliances, and desk area. The dining room offers panelled walls, RH sconces, French doors to the garden, and plantation shutters. A charming living room features built-in bookcases, window seat, wood-burning fireplace, and walkouts to a sunroom overlooking the southwest garden and pool. A mudroom and stylish powder room complete the main floor.Upstairs are four bedrooms with ample closets and antique brass hardware. The primary suite offers custom built-ins and a renovated ensuite with heated Carrara marble floors and zero-threshold shower.The fully finished lower level (8 ceilings, slate flooring) adds living space with a media room, workout room, cedar closet, laundry, and storage. Updated mechanicals include a high-efficiency furnace, central AC, 100 AMP panel, irrigation. Cedar roof, new fencing, cobblestone driveway. Outside enjoy a private oasis with saltwater inground pool, brick patios, and landscaped gardens. Steps to the Lake, Oakville Club, Yacht Squadron, Library, Performing Arts Centre, Downtown, and top schools.

Well positioned property in historic Old Oakville, south of Lakeshore, just steps to the beach, Oakville harbour and Town Square. Sitting proudly up on a rise, this 2 1/2 storey home features wonderful views, light and plenty of space to create your dream home. With lot dimensions of 105' x 105' this full-sized 11,044 SF lot is exactly twice the size of adjacent properties. Savvy buyers may investigate opportunities to sever the lot or explore the creation of an accessory dwelling unit on the property. Zoning RL3, Special Provision 11. The existing home sits entirely on one half of the property in the northeast corner leaving the south and the west portions of the lot open to potential. The existing residence features high ceilings, a grand staircase, formal living room with wood burning fireplace and adjacent sunroom. Lovely southeast dining room takes in all the sunlight. The kitchen and back entrance are in the southwest corner of the main floor. The second floor features 4 bedrooms and one main bathroom. The third floor with two large rooms used as the Primary suite features wonderful views over the garden, the lake, church tower and the beautiful trees of Old Oakville.