Oakville Real Estate | Oakville Homes with a Pool for Sale

Straight from the pages of a design magazine, this beautifully renovated, on-trend home offers more than 4,500 sq. ft. of thoughtfully designed living space. Tucked away on a quiet cul-de-sac in prestigious Southwest Oakville, it's just steps from Appleby College and the shores of Lake Ontario. The property is professionally landscaped by award-winning Gildermans, creating a stunning setting that perfectly complements this exceptional home. Designed for both everyday living and effortless entertaining, the main floor features a spacious formal dining room and a warm, inviting family room with a wood-burning fireplace. The stunning chef's kitchen is a true showpiece, featuring a Wolf induction cooktop, two double wall ovens, Sub-Zero refrigerator, two Miele dishwashers, two Marvel wine and beverage refrigerators, quartz countertops, and an impressive 9-foot island. The kitchen flows seamlessly into the family room, creating the perfect setting for gathering with family and friends. Upstairs, the luxurious primary suite serves as a private retreat, complete with a spa-inspired five-piece ensuite, walk-in closet, and an expansive terrace-ideal for enjoying your morning coffee or unwinding in the evening sun. This level also includes a generously sized second bedroom with its own ensuite, two additional bedrooms, a home office, a full bathroom, and a brand-new full laundry room for ultimate convenience. The finished lower level offers exceptional additional living space with a large recreation room, a second laundry room featuring a Miele washer and dryer, and a three-piece bathroom. Step outside to your own private backyard oasis, where a sparkling saltwater pool and beautifully landscaped gardens create the perfect escape. This exceptional home combines luxury, comfort, thoughtful design, and an unbeatable location--an opportunity not to be missed. (id:5764)

105 WHITTINGTON Place, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$3,769,000

4 Beds ⋅ 5 Baths ⋅ 40873505 MLS® #

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 & the Oakville Trafalgar Community Centre this extraordinary property offers both refined luxury and everyday convenience.LUXURY CERTIFIED (id:5764)

287 MACDONALD Road, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$6,500,000

5 Beds ⋅ 5 Baths ⋅ 40872637 MLS® #

Welcome to 54 RAYMAR PL, OAK ON L6J 6M1, a single-family residence built in 1988 that has undergone a complete transformation. This property, fully updated from its recently refreshed exterior to its meticulously remodeled interior, offers a contemporary aesthetic designed for modern living. The heart of this home is undoubtedly the recently updated kitchen, a culinary enthusiast's dream. It features a generous island with a built-in sink, providing ample space for preparation and casual dining, complemented by a convenient wine cooler. Adjacent to this, the living room provides a comfortable gathering space, enhanced by the warmth of a fireplace. The bathrooms throughout the home offer a touch of luxury, with features such as double vanities, floating vanities, and invigorating walk-in showers. Beyond the interior, the private yard is an entertainer's paradise, offering an outdoor living space complete with a fire pit and a dedicated outdoor dining area. For ultimate relaxation, indulge in the private pool or unwind in the private outdoor hot tub. The property also includes a workshop and a patio, along with a built-in garage providing four spaces for vehicles. Discover the exceptional lifestyle this meticulously updated property offers; schedule your private viewing today. Over 7000 Square ft. of Living Space. (id:5764)

54 RAYMAR Place, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$6,199,000

5 Beds ⋅ 7 Baths ⋅ 40870755 MLS® #

Set on an exceptionally private 100' × 272' professionally landscaped lot with mature trees, covered patio, and a horseshoe driveway with two entrances and a double garage with tandem bay and basement access. 368 Fourth Line is a custom 4+1 bedroom bungaloft designed for luxury living and multigenerational flexibility. Floor-to-ceiling windows and a west-facing backyard flood the home with natural light, while the open-concept kitchen, dining, and great room anchor the main living space alongside a main-floor principal bedroom and two front-facing offices. A fully self-contained 900 sq ft main-floor in-law suite with separate entrance, full kitchen, and laundry adds incredible versatility. The loft offers two bedrooms, each with its own ensuite. The resort-inspired indoor amenities include a saltwater pool, infrared sauna, and steam shower. The bright, fully finished lower level features in-floor heating, deep window wells, a bedroom, 3-piece bathroom, wine room, workshop, storage, and walk-up to back garden. Completing the home are a rear covered porch with wood-burning fireplace, built-in BBQ and pizza oven. Premium systems throughout including a security system with cameras, whole-home sound, backup generator, irrigation, central vac, advanced HVAC with full hydronic heating, integrated pool systems, and Seresco dehumidification. (id:5764)

368 FOURTH LINE, Oakville

Listing courtesy of Royal LePage Burloak Real Estate Services.

$3,999,900

5 Beds ⋅ 5 Baths ⋅ 40872032 MLS® #

Rarely does a property offer this combination of land, privacy and lakeside living. Set on a rare 1/2+ acre estate lot in one of South West Oakville's most coveted neighbourhoods, 1098 Lakeshore Rd is a custom 6,500+ sq. ft. home just steps from Lake Ontario and minutes from Appleby College. Designed with both family living and entertaining in mind, the home features 10' ceilings on the main level and 9' ceilings on the upper and lower levels, with rich hardwood floors, extensive custom millwork and thoughtful architectural details throughout. The Hampton-inspired kitchen and adjoining butler's pantry create a beautiful centre for everyday living and effortless entertaining. The large main-floor primary retreat offers the convenience of single-level living, complete with a custom walk-in closet, gas fireplace and spa-inspired 5-piece ensuite. Upstairs, two generously sized bedrooms each enjoy their own ensuite, offering comfort and privacy for family or guests. The finished lower level adds another layer of flexibility, with a second kitchen, two additional bedrooms, gym, wet bar, games area and expansive recreation space - ideal for multigenerational living, older children, extended family or guests. Outside, mature landscaping creates a private backyard retreat with a saltwater pool, waterfall feature and covered outdoor living area - perfect for summer days by the pool and evenings spent together. Beyond the property, top-ranked schools, parks, steps to the lake, trails and the shops and restaurants of downtown Oakville just minutes away. **Land. Privacy. Location. Flexibility.**A rare opportunity to enjoy space, privacy and lakeside living in one of Oakville's most sought-after settings. (id:5764)

1098 LAKESHORE Road West, Oakville

Listing courtesy of The Agency.

$2,699,000

4 Beds ⋅ 5 Baths ⋅ 40869024 MLS® #

Welcome to 2434 Taylorwood Drive, where exceptional design is found in every detail. Owned and thoughtfully curated by an interior designer, this is a home where custom is not an upgrade, it is the standard. The main floor is defined by 10' ceilings, beautifully proportioned spaces and sophisticated finishes throughout. A formal living room and dining room set the tone, complemented by a private home office and walk-in hall closet. The expansive family room features coffered ceilings, custom built-in shelving surrounding the television, a built-in desk and an exquisite marble surround framing the gas fireplace. At the heart of the home, the chef's kitchen is designed for both everyday living and entertaining, while custom drapery, millwork and carefully considered details create a polished, cohesive feel throughout. Upstairs, four bedrooms each enjoy their own ensuite, while custom built-in closet systems provide exceptional organization. The primary suite goes well beyond the expected with a separate dressing room/sitting room that can also function as a private office. A dedicated homework room with chalkboard, second-floor laundry and a window nook between the first and second floors add another layer of thoughtful functionality. For the car enthusiast, the garage may steal the show. Outfitted with a car lift, built-in tool bench and racking system, it has been designed with the same attention to detail as the rest of the home. Outside, an inground pool, pergola and outdoor kitchen create a backyard designed for entertaining and relaxed family living. The pool house with outdoor bathroom tops off the outdoor oasis! This is a home where form and function have been considered in equal measure, and where the difference truly is in the details. (id:5764)

2434 TAYLORWOOD Drive, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$2,998,000

3 Beds ⋅ 3 Baths ⋅ 40867529 MLS® #

Set on a spectacular 0.566-acre lot, this property is enveloped by towering trees and lush gardens, and backing onto the tranquil Kings Park Woods. Offering nearly 25,000 sq. ft. of privacy and tranquility, this Muskoka-like retreat sits on one of Southeast Oakville's most prestigious streets. A generously sized interlocked driveway leads past the elegant front yard to an impressive 3-car garage. Lovingly maintained by the same family for over 40 years, the home is in pristine condition. The interior features expansive principal rooms, including formal living and dining spaces, a large kitchen with a breakfast area addition, and an open-concept family room—perfect for both day-to-day living and entertaining. A wealth of windows throughout brings in abundant natural light and frames beautiful views of the front streetscape as well as the forested backyard. With multiple fireplaces and hardwood floors throughout the main level, the home exudes warmth and charm. Convenient access to the garage is provided through the laundry room. Upstairs, the spacious primary suite is complemented by three double closets, built-in bookcases, a 3-piece ensuite, and additional flexible space. Two more generously sized bedrooms, along with a 4-piece bathroom featuring a jacuzzi tub, complete this level. The true highlight of the home is the backyard—a private oasis of mature trees, manicured gardens, and a well-positioned pool that basks in sunlight. A full irrigation system ensures the landscaping stays lush. Recent upgrades include a new roof, furnace, and electrical panel, while the garage boasts 50-amp service, ideal for a lift or electric vehicle charging. Walking distance to Oakville’s top public and private schools, including OT and St. Mildred’s, and just minutes to shopping, this property offers exceptional potential. Whether you choose to build a custom home or renovate and expand this charming residence, the large lot allows for endless possibilities. (id:5764)

1296 CUMNOCK Crescent, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$2,499,000

4 Beds ⋅ 4 Baths ⋅ 40865765 MLS® #

Welcome to 3270 Shelburne Place, tucked away on a quiet cul-de-sac in sought-after Bronte, south of Lakeshore Road and just steps from Lake Ontario, parks and scenic walking trails. This beautifully updated 4-bedroom home offers an impressive list of improvements and generous living space. The main level features a family room, oak hardwood flooring throughout, 6” baseboards and California shutters. At the heart of the home is the stunning renovated kitchen, featuring an oversized 85” x 42” island, abundant cabinetry and storage, brushed-gold accents, ceramic backsplash, under-cabinet, pot and pendant lighting. The sunny adjoining eating area features a double-sided wood-burning fireplace, skylight, and sliding glass doors, walk out to the patio and pool with waterfall area. The stylish, renovated laundry room features shiplap walls, a butcher-block counter, a laundry sink, custom storage and updated flooring. The main-floor powder room has also been beautifully updated. The upgraded oak staircase adds warmth and character, leading to 4 bedrooms with updated carpeting, lighting and California shutters. The primary suite offers a private sitting area, walk-in closet and 4-piece ensuite with a skylight, while the 5-piece main bath features heated floors, a glass shower, jetted tub and double sinks. The finished lower level provides even more living and entertaining space, new vinyl flooring, pot lights, a wet bar with ceramic backsplash and shelving, an updated 2-piece bathroom, a sauna with a separate shower and plenty of storage. Step outside to your own private backyard retreat featuring a heated saltwater pool and stone patios, perfect for summer entertaining. The property also offers ample driveway parking, security lighting and an updated garage with a newly painted floor. A wonderful opportunity to enjoy a beautiful home in one of Bronte’s most desirable pockets, close to the lake, parks, schools, shopping and restaurants. (id:5764)

3270 SHELBURNE Place, Oakville

Listing courtesy of Real Broker Ontario Ltd..

$2,198,000

4 Beds ⋅ 2 Baths ⋅ 40866851 MLS® #

Welcome to this bright and beautifully maintained raised bungalow, offering over 2,600 sq. ft. of finished living space and a spectacular backyard oasis, ideally situated in the highly sought-after West River neighbourhood. The sun-filled eat-in kitchen is a true highlight, surrounded by wraparound windows overlooking the private backyard and featuring an extended quartz peninsula, generous pantry space, gas stove, reverse osmosis water system, and patio doors leading directly to the outdoor entertaining areas. The inviting living and dining rooms feature built-in bookcases and offer an ideal setting for entertaining family and friends. The main level also includes a spacious primary bedroom, two additional well-sized bedrooms—one currently used as a home office—and a 4-piece bathroom. The finished lower level provides exceptional additional living space with a cozy den featuring a gas fireplace, a large sun-filled bedroom, 3-piece bathroom, spacious recreation room currently used as an office, and a functional laundry room with ample cabinetry and counter space. Step outside and discover your own private backyard retreat, complete with multiple decks and patios, a gazebo, raised reading nook, storage shed, beautifully landscaped mature gardens and trees, and an impressive inground pool with spillover hot tub. Whether entertaining guests, enjoying summer days by the pool, or simply relaxing in the peaceful surroundings, this backyard offers something for everyone. Ideally located within walking distance of downtown Oakville, vibrant Kerr Village, Oakville GO Station, Westwood Park and Forster Park with its playground and splash pad, as well as public transit and school bus routes. A wonderful opportunity to enjoy comfortable family living, exceptional outdoor space, and a convenient Oakville location. (id:5764)

316 RIVER SIDE Drive, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$3,300,000

6 Beds ⋅ 4 Baths ⋅ 40866605 MLS® #

Classic Oakville Setting. Contemporary Family Living. Positioned in one of Southeast Oakville’s most established neighbourhoods. Completely rebuilt from the foundation up in 2009, this distinctive family home offers 3,950 sq. ft. of total living space across three levels, with a well-planned layout designed for both everyday family living and entertaining. The main level is flooded with natural light, with beautiful sightlines from the front entry through to the rear garden and pool. The bright, open-concept kitchen, dining and living areas are complemented by a private office and practical mudroom. A generous kitchen island with seating for six creates a natural gathering point. A complete renovation of the living room, kitchen and mudroom was undertaken in 2022, including a new fireplace and custom mantle, updated stairs and a refreshed overall design that brings a contemporary feel and improved functionality to the main level. The second level offers five spacious bedrooms and two full bathrooms, providing excellent flexibility for family and guests. The lower level adds a walk-up, recreation and games areas, exercise room, three-piece bathroom, laundry and ample storage. Outside, the private, fully fenced backyard (93 ft across the back) is designed for summer living, with a upgraded solar-heated saltwater pool, expansive lawn and generous entertaining areas. 2023 pool improvements include a new heater, liner, chlorinator and pump, while the driveway, deck, walk-up and fencing were also updated that year. Further updates include interior improvements in 2022, along with Hunter Douglas motorized shades, smart lighting controls, motion sensors and security technology added in 2024. An exceptional Southeast Oakville location close to top public and private schools, including Maple Grove Public School and Oakville Trafalgar High School, with easy access to the GO, highways, shopping, Downtown Oakville and the lake. (id:5764)

407 MAPLE GROVE Drive, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$5,799,000

5 Beds ⋅ 6 Baths ⋅ 40866459 MLS® #

Poised along one of Oakville’s finest streets, 1074 Lavender Lane is a custom-built residence where enduring craftsmanship and gracious family living come together. Surrounded by distinguished homes in a prestigious neighborhood, this luxury-certified property offers more than 7,000 square feet of total living space. Inside, refined formal living and dining rooms are complemented by a private office and an inviting family room with built-in television cabinetry. The gourmet kitchen is designed for serious cooking and effortless hosting, showcasing granite surfaces, integrated appliances, a substantial island, and direct connection to the family room. A butler’s pantry elevates entertaining with a dual-zone wine refrigerator, a beverage refrigerator, and a double-drawer dishwasher. Main-floor laundry and a mudroom provide practical access to the garage and outdoors. Upstairs, the primary retreat impresses with a cathedral ceiling and an expansive walk-in closet offering conversion potential. Each upper bedroom enjoys ensuite access. The finished lower level adds a guest bedroom, bathroom, music or exercise room, expansive recreation area, and a remarkable stone-lined wine cellar entered through a hand-carved door. Outside, a screened porch with a gas fireplace overlooks a private, tree-lined, resort-like setting with an inground pool and attached hot tub. Ideally situated near top-rated public, Catholic, and private schools, scenic parks and ravine trails, convenient transit, and the upscale shops and dining of downtown Oakville, this thoughtfully crafted home offers an exceptional setting for refined family living. Built with exceptional care and attention to detail, it combines comfort, privacy, and an enviable Oakville location. Luxury Certified. (id:5764)

1074 LAVENDER Lane, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$1,550,000

3 Beds ⋅ 2 Baths ⋅ 40865357 MLS® #

Attention Builders, Renovators & End Users! An exceptional opportunity in prestigious Bronte East, set on a premium southeast-facing 89.5 x 126 ft corner lot surrounded by mature trees and stunning custom homes. Featuring RL3-0 zoning with 35% maximum lot coverage, this property offers plenty of potential to build your dream home, renovate, or simply move in and enjoy. The existing 3-bedroom home offers a bright and inviting layout with hardwood flooring, an updated kitchen featuring stainless steel appliances and ample storage, and a spacious living room with a gas fireplace. Three generously sized bedrooms are filled with natural light, complemented by a beautifully renovated main bathroom completed in 2024. The finished basement provides additional living and entertaining space complete with a full bathroom, wet bar and wine rack. Step outside to a private, fully fenced backyard with mature landscaping and a heated saltwater in-ground concrete pool with a new liner installed in 2024. It's a great space for relaxing and entertaining throughout the summer. Ideally situated in one of South West Oakville's most established neighbourhoods, just minutes from Lake Ontario, scenic walking and biking trails, Downtown Oakville, YMCA and Appleby College. Morden Public School is within walking distance, with a school bus stop at the corner for St. Nicholas Catholic Elementary School. Suffolk Park is located just steps away at the end of Burton Rd, while nearby public transit provides convenient access to Downtown Oakville, recreation facilities, arenas and outdoor skating. A rare combination of an oversized corner lot, unbeatable location and outstanding future potential in one of Oakville's most sought-after neighbourhoods. **Some photos are virtually staged** (id:5764)

505 PATRICIA Drive, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$1,549,999

5 Beds ⋅ 3 Baths ⋅ 40864269 MLS® #

Welcome to this beautifully updated detached home situated on a spacious 65 x 115 ft lot in one of Oakville’s MOST DESIRABLE FAMILY-FRIENDLY neighbourhoods. Thoughtfully renovated with quality finishes throughout offering over 2200sqft+ of finished living space. Featuring an open-concept layout, a stylish modern kitchen with stainless steel appliances, engineered hardwood flooring, three generously sized bedrooms on the main level, and two full bathrooms, including a private ensuite in the primary bedroom. The fully finished lower level with a separate entrance offers two additional spacious bedrooms, a full bathroom, and a rough-in for a kitchen or wet bar, creating excellent potential for an in-law suite or multi-generational living. Step outside to your impressive private backyard oasis, completely redesigned in 2022. Enjoy the professionally landscaped yard featuring a stunning interlocking patio, spacious entertaining area, and an inviting HEATED IN-GROUND POOL perfect for relaxing or hosting family and friends. Additional updates include Furnace (2019), Pool Liner (2020), and Pool Heater (2024) offering added peace of mind. Ideally located within walking distance to the highly rated Sunningdale Public School and White Oaks Secondary School, as well as White Oaks Park, Oakville Public Library, River Oaks Community Centre, shopping, restaurants, transit, and QUICK ACCESS TO QEW. (id:5764)

98 MILLER Road, Oakville

Listing courtesy of Re/Max Twin City Realty Inc..

$3,995,000

4 Beds ⋅ 4 Baths ⋅ 40862694 MLS® #

An exceptional opportunity on one of Southeast Oakville’s most prestigious streets. Set on a nearly half-acre lot, 16 Colonial Crescent offers approximately 100 feet of frontage and more than 210 feet of depth, with outstanding proportions for a substantial custom build. The lot’s generous dimensions and mature setting allow for an impressive new residence while maintaining exceptional privacy and meaningful outdoor space. Surrounded by mature trees and distinguished homes, the property offers a sense of scale and seclusion rarely found this close to the lake. RL1-0 zoning provides the potential for more than 6,000 square feet of above-grade living space, while still allowing for generous outdoor living, a pool and landscaped gardens, subject to applicable approvals. The property is currently a spacious four-bedroom residence offering approximately 3,700 square feet above grade, plus a finished lower level, attached double garage and inground pool—providing the flexibility to lease the home while planning a future build. Colonial Crescent is a quiet, established enclave known for its large properties, mature tree canopy, and impressive custom homes. Just steps from the lake and Gairloch Gardens, the location also offers convenient access to Downtown Oakville, excellent public and private schools, parks and the waterfront. A rare opportunity to secure a significant building lot on one of Southeast Oakville’s premier streets and create an exceptional custom home in an highly sought-after location. (id:5764)

16 COLONIAL Crescent, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$5,399,000

5 Beds ⋅ 5 Baths ⋅ 40859654 MLS® #

WATERFRONT PROPERTY! Experience the Potential of Lakeside Living. Perfectly situated on a premium 90' x 152' lakefront lot, this residence offers breathtaking, unobstructed water views from every principal room. With over 5,700 square feet of finished living space, the home presents an exceptional opportunity to bring your vision to a truly remarkable waterfront setting. The existing layout offers generous space for family living and entertaining, with rich hardwood flooring, limestone tiles, four skylights, two spacious family rooms, a private office, and a large kitchen with lake views! Upstairs, four generously sized bedrooms provide excellent space and privacy, while the primary suite showcases spectacular lake views. A convenient upper-level laundry room and walkout to the second-floor terrace offer additional potential to create a beautiful retreat overlooking the water. The fully finished lower level includes a fifth bedroom with a private ensuite, ideal for guests, extended family, or a nanny suite. Outdoors, the property offers an incredible foundation for creating your own waterfront oasis. The views, privacy, and ever-changing beauty of the waterfront truly have to be experienced to be fully appreciated, as the changing seasons, light, and skies create a new view from moment to moment. Additional highlights include a three-car garage, four fireplaces, an irrigation system, and ample storage throughout. This is a rare opportunity to transform an expansive waterfront property into a spectacular lakeside home, while enjoying the privacy, scale, and extraordinary setting that cannot be replicated. Luxury Certified. (id:5764)

2372 CARRINGTON Place, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$3,298,000

6 Beds ⋅ 3 Baths ⋅ 40855310 MLS® #

Set on a remarkable estate-sized lot in coveted Morrison, this traditional family home offers an exceptional opportunity in one of SE Oakville’s most established + sought-after neighbourhoods. Surrounded by towering mature trees + an enclave of beautiful homes, the setting offers privacy, character + permanence. Walk to elementary + secondary schools, Lake Ontario, Gairloch Gardens, waterfront trails + parks, while enjoying the rare scale of a 100'x150' lot. The immaculate grounds + private rear yard create a wonderful setting for family life through every season. With 5+1 beds, 3.5 baths + triple car garage, it’s poised to welcome a large family. Expansive principal spaces create a sense of scale across the main level. Beautifully appointed kitchen offers abundant cabinetry, ample workspace + picturesque views of the yard, w/a separate breakfast area connecting easily to the living + dining rooms. Tucked away, the main floor laundry + mudroom add everyday convenience. Bright solarium-style family room w/fireplace provides a warm space to gather, surrounded by generous glazing. Upstairs, five bright bedrooms offer generous proportions + natural light. Refined main bath serves the family bedroom wing, while the expansive primary suite features a very large ensuite + comfortable retreat-like proportions. LL is designed for family life w/a spacious recreation room, wet bar, gym area, 6th bed + full bath. There is room for movie nights, guests, older children + everything in between. Masterfully landscaped + incredibly private, the rear yard is anchored by a linear pool, stone lounges + layered gardens. A cedar-thatched gazebo w/fireplace creates a cozy gathering spot, while the stone patio is ideal for al-fresco dining. Flat grassy areas provide plenty of space for summer games + even a winter rink. Cherished neighbourhood known for its natural beauty, community + enduring appeal, Morrison offers an exceptional place to set down roots + truly enjoy the neighbourhood. (id:5764)

240 COLCHESTER Drive, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$1,780,000

4 Beds ⋅ 4 Baths ⋅ 40857284 MLS® #

Completely renovated, top-to-bottom, inside and out. Set on a leafy residential street, this substantial brick home combines classic curb appeal with generous living space and a private backyard with swimming pool, newer fencing and extensive hardscaping. Inside, the home is bright, meticulous and well designed. New hardwood floors run throughout the main and upper levels, complemented by a contemporary staircase, replaced windows and renovated baths. The large eat-in kitchen is the heart of the home, with bright cabinetry, updated appliances and a generous island overlooking the backyard Formal front room, complete with gas fireplace, provides a quiet retreat or home office, while the family room, with fireplace and two skylights, offers another comfortable gathering space. Upstairs, the exceptionally large primary suite features a walk-in closet and renovated ensuite with double vanity. Two additional bedrooms are generously proportioned, each with double closets, making this a particularly functional home for a growing family. The finished lower level with wide plank hardwood adds considerable living space, with two separate recreation areas with gas fireplace, a private guest bedroom with ensuite bath and a stylish laundry room with loads of storage and raised washer/dryer. Outside, the property delivers the quintessential Oakville setting: a classic red-brick exterior, professionally landscaped grounds, a large double garage and driveway and a backyard designed for summer living around the pool. Surrounded by a mix of newer custom homes and established two-storey residences, this is a neighbourhood that continues to evolve while retaining its leafy, established character. Local schools are within an easy walk, and the location offers the appeal of being south; close to the lake and downtown amenities and a lifestyle that makes this part of Oakville so coveted. (id:5764)

579 FOURTH Line, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$7,599,000

5 Beds ⋅ 7 Baths ⋅ 40857110 MLS® #

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. (id:5764)

46 SECOND Street, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$3,649,999

4 Beds ⋅ 6 Baths ⋅ 40856636 MLS® #

Tucked into a quiet court, this custom modern farmhouse, built by custom home builder Millbay Carpentry, sits on a 66 x 187 ft lot and offers over 3,900 sq ft above grade with 4 bedrooms and 5.5 bathrooms, plus a finished walkout basement for approximately 5,500 sq ft of total living space. A custom EPAL front door opens to a double-height foyer with pine stairs and matte black railings, complemented by 10 ft main-floor and 9 ft upper- and basement-level ceilings. The great room features a wall of windows overlooking the pool and gardens, accented by cedar beams. The chef’s kitchen showcases custom Barzotti cabinetry, a porcelain CIOT backsplash, JennAir appliances and an 8-burner range, along with a hidden walk-in pantry, custom built-ins and designer lighting. The primary ensuite features a steam shower, while the finished basement offers a gym, theatre, bar, lounge, gaming area and ample storage. Outdoors, enjoy a heated saltwater pool with an automatic cover, turf, irrigation and landscape lighting. Conveniently located near Oakville’s only public International Baccalaureate (IB) school, as well as GO Transit, major highways and Oakville Place. (71030456) (id:5764)

1114 TRUMAN Avenue, Oakville

Listing courtesy of Comfree.

$1,999,999

6 Beds ⋅ 5 Baths ⋅ 40851961 MLS® #

Imagine never needing a cottage again. Welcome to one of Lakeshore Woods' most exceptional properties, where luxury living meets the tranquility of a private Muskoka-inspired retreat. Set on a spectacular 50 x 180 ft lot backing onto protected greenspace, this remarkable home offers nearly 3,000 sq. ft. above grade, plus 1,280 sq. ft. of beautifully finished lower-level living space. Designed for both everyday living and effortless entertaining, the resort-style backyard is the true showpiece, featuring a saltwater pool with a stone waterfall, gazebo, cabana, professionally landscaped gardens, and complete privacy surrounded by mature trees. Inside, timeless elegance meets modern comfort with rich hardwood floors, a natural oak staircase, soaring 18-foot cathedral ceilings, and an abundance of natural light. The gourmet kitchen flows seamlessly into the breakfast area and opens directly to the backyard, while the inviting family room with a gas fireplace creates the perfect gathering space. Upstairs, you'll find four spacious bedrooms, including a luxurious primary retreat with a spa-inspired ensuite and custom walk-in closet. The fully finished lower level adds incredible versatility with two additional bedrooms, a brand-new three-piece bathroom, rough-in for a future kitchen, and potential for a separate walk-up—ideal for extended family or multi-generational living. Complete with parking for up to eight or nine vehicles and located just minutes from Lake Ontario, scenic trails, hidden beaches, top-rated schools, shopping, the GO Station, and major highways, this is more than a home—it's a lifestyle. (id:5764)

215 BURLOAK Drive, Oakville

Listing courtesy of Royal LePage Burloak Real Estate Services.

$2,599,999

5 Beds ⋅ 4 Baths ⋅ 40845570 MLS® #

Perfectly positioned in one of Southwest Oakville's most sought-after neighbourhoods, directly across from the prestigious Appleby College, this exceptional family residence offers over 5,000 square feet across all levels, blending timeless elegance with outstanding functionality. Thoughtfully designed for both everyday living and entertaining, the main level showcases expansive principal rooms filled with natural light. The chef-inspired kitchen is the heart of the home, featuring custom cabinetry, granite countertops, a large centre island, quality appliances, and an adjoining breakfast area overlooking the private backyard. The inviting family room offers beautiful seamless access to the outdoor living spaces, while the formal living and dining rooms provide refined spaces for hosting family gatherings and special occasions. A handsome wood-panelled home office creates the perfect work-from-home environment. Upstairs, the home offers 3 spacious bedrooms, highlighted by a luxurious primary retreat complete with a generous walk-in dressing room and spa-inspired ensuite with heated floors. The additional bedrooms are well-proportioned and ideal for family or guests. The finished lower level extends the living space with 2 additional bedrooms, a large recreation/media room, a custom wine cellar, ample storage, and flexible space perfect for extended family, teenagers, or a home gym. Set on a private, mature lot, the backyard features an in-ground pool, hot tub and exceptional privacy, creating the perfect setting for summer entertaining. Ideally located just moments from the lake, parks, downtown Oakville, and top-rated schools, this is an outstanding opportunity to own a distinguished family home in one of Oakville's most coveted neighbourhoods. (id:5764)

104 WHITTINGTON Place, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$1,698,000

4 Beds ⋅ 5 Baths ⋅ 40845026 MLS® #

Welcome to 2330 Valleyridge Drive, an exceptional move-in ready family home offering 4 bedrooms, 5 bathrooms, and 3,937 sf of finished living space in one of Oakville’s most sought-after communities. Deceptively spacious & much larger than it appears, this impressive property backs onto a private ravine and features a saltwater inground pool, professionally landscaped grounds, and a backyard retreat surrounded by mature cedar trees. A 1.5-car garage with inside entry and parking for 4 cars completes the property. Ideally located close to top-rated schools, parks, walking trails, shopping & everyday amenities. Hardwood flooring extends throughout the principal rooms. The living room features 9’ ceilings, a gas fireplace, and built-in surround sound. The family room flows seamlessly into the breakfast area and eat-in kitchen featuring granite countertops, custom cabinetry with soft-close drawers, pot and pan drawers, under-cabinet lighting, stainless steel appliances, pot lights, and a walkout to the backyard. A 2pc powder room completes the main level. The upper level offers four generous bedrooms, including a private primary retreat with a walk-in closet and 5pc ensuite featuring double sinks, a freestanding soaker tub, glass-enclosed shower, and separate water closet. Two additional 4pc bathrooms and upper-level laundry complete this floor. The finished lower level adds exceptional living space with a large recreation room, 3pc bathroom, and abundant storage. Outside, the private backyard showcases a saltwater pool, new deck (2025), mature cedar trees, and a peaceful ravine setting, creating an exceptional space for outdoor entertaining and relaxation. Combining generous living space, a functional family layout, move-in ready (newer roof, furnace, pool heater & pump) convenience, and an exceptional ravine setting, this Oakville home presents an outstanding opportunity in a highly sought-after neighbourhood. (id:5764)

2330 VALLEYRIDGE Drive, Oakville

Listing courtesy of Royal LePage Burloak Real Estate Services.

$33,000,000

7 Beds ⋅ 12 Baths ⋅ 40839819 MLS® #

2054 Lakeshore Rd. East is one of Oakville's finest lakefront estates.Situated on 1.6 acres & 164.22 ft of pristine shoreline, complete with deck & stairway access to the water. Designed by renowned architect Gren Weis & brought to life by the exceptional craftsmanship of Coulson Fine Homes.This magnificent 7-bdrm, 13-bath home spans an impressive 19,210 sq ft.Step into the grand formal entrance where limestone cast walls create a dramatic first impression serving as a prelude to the extraordinary spaces beyond.The residence showcases 12 ft ceilings on the main level, Brazilian walnut flooring thru-out & custom cabinetry adorns this remarkable home.The estate features an expansive living & dining rm w/breathtaking water views, perfect for intimate gatherings or grand celebrations.Step outside to the covered terrace where you can relax to the sounds of the Bellagio inspired fountains & waterfall.The gourmet open-concept kit.flows effortlessly into the fam.rm where water views & fp create a relaxed & comfortable space.The lower-level transforms into an entertainer's paradise, w/a state-of-the-art home theatre, gym w/direct access to the infinity edge pool, steam room, golf simulator, wine cellar, billiards area w/rec room & catering kit.A private 2-bdrm nanny suite w/sep. entrance provides additional flexibility.An elevator gives you convenient access to all 5 levels of this thoughtfully designed home.The outdoors offers multiple entertaining areas nestled within the manicured landscaped grounds, the lakefront deck & poolside.The power screened sunroom offers 3 season enjoyment. His&Her double car garages to accommodate 4 vehicles w/additional parking for 15 more on the circular driveway & auxiliary prkng areas-perfect for hosting memorable events.This waterfront estate represents more than just a home it's a lifestyle statement where every detail has been carefully curated to create an environment of uncompromising luxury & comfort. LUXURY CERTIFIED. (id:5764)

2054 LAKESHORE Road East, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$7,470,000

5 Beds ⋅ 7 Baths ⋅ 40839389 MLS® #

Welcome to 129 Wolfdale Ave, a custom-designed modern craftsman estate, positioned on a premium lot in Southwest Oakville. With approximately 7,300 sq.ft. of living space, and an incredible 1,700 sq.ft. two level garage that stores 6 cars indoors, serviced by a car elevator. This exceptional home blends refined architecture resort-inspired outdoor living, surrounded by a private, tree-lined backdrop. The portico leads into a breathtaking foyer, setting the stage for the elegant interiors beyond. Considered finishes include coffered ceilings, herringbone marble flooring, and wide-plank oak throughout the principal spaces. A stylish main floor office, complete with bespoke millwork. The great room features 14' ceilings, a custom walnut media wall, and a floor-to-ceiling stone fireplace. This space flows effortlessly into the chef's kitchen, beautifully appointed with a full Thermador fridge and freezer, Gaggenau double ovens, range, steam oven, warming drawer, and quartz countertops. A fully equipped butler's pantry that keeps entertaining effortless. The upper-level hosts four spacious bedrooms, each with private ensuites with heated floors. The primary suite is a true retreat, featuring a private balcony, a spa-inspired five-piece ensuite, and a custom walk-through closet. The finished lower level offers additional living space, including a fifth bedroom, walk-up access to the rear garden, gym and home theatre. All six garage spaces, along with driveway and front walkway are radiant heated, ensuring year-round comfort and no snow buildup. (id:5764)

129 WOLFDALE Avenue, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$4,295,000

6 Beds ⋅ 8 Baths ⋅ 40793876 MLS® #

This is a remarkable vacant lot that includes drawings and building permit. House pictures are renderings and details are from the drawings. Embark on a life of uncompromised luxury with this architectural masterpiece by renowned architect David Small. Perfectly located South of Lakeshore steps from Appleby College, lake and downtown Oakville. Evoking a sophisticated Laneway Country atmosphere on a rare 90’ x 340’ lot with walk-out basement. The estate features a long circular private drive that frames a sun-drenched, West-facing backyard. The home is designed as the ultimate multi-generational sanctuary, that offers a rare Double Primary layout: a magnificent main-floor master suite for accessible luxury, plus a second-level master retreat with separate His & Her ensuites. The elevator services all three levels, ensuring effortless movement throughout soaring interiors defined by dramatic cathedral ceilings. With building permits in hand and a bespoke interior package by WOLFE Interior Design, this Net Zero Ready estate blends timeless character with elite modern performance. Car enthusiasts will prize the 5-car capacity, utilizing the attached garage and the detached tandem garage within the cabana. Beyond the essentials, the floor plan is packed with exceptional features, including a main floor office, lower level dedicated music/theater room, glass-walled fitness center, custom sauna and steam room, wine cellar, and private nanny and guest suites. Surrounded by 10M-12M estates. Architectural drawings, interior design, floorplans and building permits available on request. 10+++ (id:5764)

408 LAKESHORE Road West, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

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