Oakville Real Estate | Oakville Homes with a Pool for Sale

Behind its striking curb appeal lies a home that has been thoughtfully reimagined from top to bottom. Nestled on a quiet, tree-lined street in the highly sought-after Iroquois Ridge School district, this beautifully renovated four-level side split offers the perfect balance of style, comfort and functionality. The bright, renovated kitchen and dining area have been designed for everyday living and effortless entertaining. Quality finishes, engineered hardwood on the main and upper levels, modern stairs, and a charming coffee nook create an inviting space for family and friends. Walk out from the kitchen to the expansive entertaining deck overlooking your outdoor oasis. Designed to be enjoyed in every season, the private backyard features an inground pool, oversized deck with glass railings, a second walkout patio off the family room, a secluded deck beside the shed, mature trees, lush landscaping, an extended privacy hedge and plenty of lawn for children and pets to play. Spacious bedrooms are complemented by a luxurious renovated bathroom with ensuite privileges, a freestanding soaker tub, oversized shower and elegant finishes. The huge family room is perfect for relaxing or entertaining. The completely rebuilt lower level offers exceptional flexibility with a spacious bedroom featuring an egress window and walk-in closet, a beautifully renovated bathroom, impressive laundry room and storage-ideal for guests, teens, a home office or gym. Extensive updates mean you can simply move in and enjoy, including the pool with a new pump, ionizer and heat exchanger. Across the street, enjoy easy access to scenic ravine trails and walking paths. Walk to shops, restaurants and everyday amenities, and easy access to highways and the GO for commuters. Beautifully renovated. Exceptionally private. Effortlessly livable. The kind of home you'll love coming home to. For full list of upgrades see the brochure. (id:5764)

1281 LAKEVIEW Drive, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,389,999

4 Beds ⋅ 5 Baths ⋅ 40859223 MLS® #

Welcome to this exceptional executive home in the prestigious Joshua Creek community, offering over 6,200 sq. ft. of finished living space, including approximately 4,100 sq. ft. above grade. Designed with both elegance and functionality in mind, this home features soaring ceilings, hardwood flooring throughout, and a thoughtfully designed layout perfect for family living and entertaining. The main level offers a private office with French doors, a formal living room with a double-sided gas fireplace, and a spectacular family room with soaring 18-foot ceilings. The spacious kitchen is complemented by a convenient servery leading to the formal dining room, while the mudroom, laundry room, and stylish powder room add everyday convenience. Upstairs, the luxurious primary suite features two walk-in closets and a spa-inspired 5-piece ensuite with a freestanding tub, glass shower, and double vanity. Three additional generously sized bedrooms each enjoy ensuite or semi-ensuite access, providing comfort and privacy for family and guests. The finished lower level is designed for both relaxation and entertainment, complete with a recreation room featuring a gas fireplace and custom built-ins, a wet bar, a home gym, and a full bathroom. Step outside to your private backyard oasis with mature landscaping, a spacious deck, built-in gas BBQ, and an inviting in-ground pool—perfect for entertaining or relaxing all summer long. Ideally located close to top-rated schools, parks, scenic trails, shopping, restaurants, and major highways, this remarkable Joshua Creek home offers the perfect combination of luxury, comfort, and convenience. (id:5764)

2384 ROCK POINT Drive, Oakville

Listing courtesy of Keller Williams Edge Realty.

$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..

$1,899,000

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 Oak Bay Homes, 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.

$2,999,000

4 Beds ⋅ 4 Baths ⋅ 40856761 MLS® #

Welcome to 1194 Stirling Drive—an exceptional value and rare opportunity to own a substantial 4,294 sq. ft. home on an expansive private corner lot in one of SW Oakville’s most desirable neighbourhoods. The impressive scale, space and setting of this property truly must be experienced in person. Offering remarkable indoor and outdoor living, this home provides an incredible setting for family life, entertaining and enjoyment through every season. The spectacular backyard retreat features a newly built (2023) Gib-San Gunite pool, professionally landscaped grounds, a sprawling 1,500 sq. ft. deck and powered pergola, creating a private oasis and seamless extension of the home. Inside, expansive windows and skylights fill the open-concept living spaces with natural light, while hardwood floors and two stone gas fireplaces add warmth and character. At the heart of the home, the chef’s kitchen features top-tier Miele appliances, Cambria Quartz countertops, two copper sinks, a walk-in pantry and heated floors extending into the glass-enclosed sunroom. Upstairs, the primary suite offers vaulted ceilings, a walk-in closet and spa-inspired ensuite with steam shower, heated bench and floors, jets and custom cabinetry. Three additional bedrooms provide plenty of space for family and guests, including a unique two-level bedroom with ensuite and partial lake views. A separate west wing features a generous 25' x 16' recreation room, adding even more versatile living space. With over 4,200 sq. ft., an exceptional lot, spectacular pool and outstanding indoor and outdoor living, 1194 Stirling Drive offers tremendous value in a highly sought-after Oakville location. Walk to downtown shops, Bronte Harbour, the lake, trails and restaurants, with excellent public and private schools nearby. A truly unique property offering the space, lifestyle and location that are increasingly hard to find. (id:5764)

1194 STIRLING Drive, Oakville

Listing courtesy of City Brokerage.

$2,999,000

4 Beds ⋅ 6 Baths ⋅ 40852645 MLS® #

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..

$7,249,000

5 Beds ⋅ 5 Baths ⋅ 40852110 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..

$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.

$3,949,000

4 Beds ⋅ 5 Baths ⋅ 40851190 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, and the Oakville Trafalgar Community Centre this extraordinary property offers both refined luxury & everyday convenience. LUXURY CERTIFIED (id:5764)

287 MACDONALD Road, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$1,625,000

5 Beds ⋅ 3 Baths ⋅ 40850343 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 all summer long. 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 with quick access to the QEW. (id:5764)

98 MILLER Road, Oakville

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

$2,180,000

6 Beds ⋅ 4 Baths ⋅ 40849822 MLS® #

STUNNING EXECUTIVE RESIDENCE nestled in prestigious Southeast Oakville. Boasting over 2900 Square Feet with 4+2 Bedrooms, this IMMACULATE & SPACIOUS home offers refined living with top to bottom renovations, showcasing premium upgrades and high-end finishes throughout. The Main Level features elegant dark Brazilian hardwood flooring, a Gourmet Kitchen with granite countertops, high-end built-in appliances, custom cabinetry by Gravelle, a substantial centre Island, heated travertine tiles and a walk-out to a Private backyard Oasis. Hosting a Formal Dining Room with over-sized windows - allowing abundant amount of natural light & a Living Room with high quality crown moulding and an elegant gas fireplace decorated with black granite. Upper Level features Magnificent Primary Retreat with walk-in closet and spa-like 6 piece ensuite featuring his and her sink vanities, air jet soaker tub, and stand-in shower. The fully finished Lower Level is an ENTERTAINER'S dream, complete with a large recreation room along with media surround speaker system plus two additional large Bedrooms and a 3 piece Bathroom. Lower Level hosts a WET BAR created by K Design with granite countertop, Sub-Zero wine fridge, Kitchen Aid Bar fridge, Fisher & Paykel dishwasher drawer, B/I Panasonic Microwave, bar sink and under counter lights. Outdoors, a Private backyard retreat with a Saltwater Inground Pool, 5 Zone Irrigation system, and an inviting lounge patio, ideal for summer gatherings. This LUXURIOUS home is surrounded by parks, scenic walking trails and minutes away to major highways, GO Train, Shopping, Restaurants and TOP-RATED SCHOOLS. This home delivers luxury, comfort and UNBEATABLE LOCATION. DON'T MISS OUT - BOOK TODAY!! (id:5764)

500 BLENHEIM Crescent, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$3,898,000

5 Beds ⋅ 5 Baths ⋅ 40846700 MLS® #

Set on a pristinely landscaped lot in coveted Morrison, this refined family residence blends timeless architecture w/everyday livability in one of Oakville’s most prestigious neighbourhoods. Positioned w/in a supreme school catchment, steps to Oakville Trafalgar HS, & moments to parks, Edgemere Promenade + local amenities, the location is as exceptional as the home itself. Traditional detailing, steep gables + crisp architectural lines lend a classic presence, while mature trees, curated gardens + layered natural stone frame the polished exterior. The resort-inspired rear grounds with a glistening pool, stone lounges + tranquil gardens are ideal for family fun. With over 5500sf of living space, 4+1 beds & 4.5 baths this home space + privacy when needed. Expansive glazing + elevated ceilings define bright, airy principal spaces. The dining room anchors the main level, seamlessly connecting the great room + expansive kitchen for effortless entertaining. The great room is centred around a fireplace + opens through double French doors to a private lounge with concrete gas fire bowl. The oversized kitchen island creates a natural gathering place, while a tucked-away home office overlooks the lush front gardens.The upper level offers four generously sized bedrooms with elevated ceilings, walk-in closets + expansive glazing. Privately positioned, the primary suite features vaulted ceilings, a marble fireplace, fully outfitted dressing room + hotel-inspired ensuite.The LL extends the home’s polished living spaces w/a spacious rec room, wet bar, games area, additional bedroom + full bath. Outdoors, multiple lounge + dining areas surround the resort-style pool beneath a canopy of mature trees, creating a private setting designed for both relaxed living + effortless entertaining. This is a refined home with a polished exterior in one of Oakville’s most established neighbourhoods. (id:5764)

376 WEDGEWOOD Drive, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$3,899,000

4 Beds ⋅ 3 Baths ⋅ 40846419 MLS® #

Exceptional property, situated in prime Morrison area of southeast Oakville, 1.293 Acres with tall trees and English-country gardens, abutting Morrison Creek at the back. The lot measures: 112ft (front and back) x 497ft (south side) x 505ft (north side).The property provides lovely landscaping, trees and fragrant bushes in the expansive backyard, with the lawn extending all the way back to top of bank with the ravine extending to Morrison Creek at the very back of the property. The home offers a sense of timeless elegance and warmth, with rich solid-wood floors in most principal rooms and light pouring in from multiple bay windows throughout. Walk into the refined living room/great room and find a grand, wood-burning fireplace, with lush views of the backyard from both bay windows. The dining room offers a sophisticated light-filled space from a front-facing bay window and provides ample table room for large gatherings. Next to the dining room is the charming office space, with built-in bookshelves and wood floors, plus a walkout to yard. There is a potential in-law suite beside the office with a door separating the suite which includes the 4th bedroom and a 4-pc bathroom (was originally planned as an in-law suite). The eat-in kitchen provides plenty of cupboard space and a cozy sunroom added - a tranquil reading nook looking out to the gardens. The spacious, charming primary bedroom provides a 4-pc ensuite bathroom, walk-in closet, and an adorable alcove/sitting room looking out to the front courtyard. Down the hall, a sunny, quaint walk-through to the back wing looks out to the private, west-facing terrace overlooking the 40', fenced-in, salt-water pool. This wing includes 2nd and 3rd bedrooms plus a 5-pc bathroom. There are multiple entries to the this home plus a detached 2-car garage and ample parking on the interlock driveway. Oakville Trafalgar High School district walk to downtown. Ideal for a new build or renovations! (id:5764)

230 MORRISON Road, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$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..

$4,499,000

5 Beds ⋅ 5 Baths ⋅ 40842845 MLS® #

Set on a rare and private 1/2+ acre estate lot in one of South West Oakville's most coveted lakeside neighbourhoods, this stunning custom designed home offers over 6,500 sq. ft. of luxurious living space just steps from Lake Ontario and within minutes to esteemed Appleby College. Thoughtfully designed for both everyday living and grand-scale entertaining, the home features 10' ceilings on the main level, 9' ceilings on the upper and lower levels, extensive custom millwork, rich hardwood flooring, and exceptional craftsmanship throughout. The Hampton-inspired custom kitchen and butler's pantry serve as the heart of the home, complemented by luxurious ensuite bathrooms and high-end finishes at every turn. The main floor primary retreat offers the convenience of single-level living, complete with a custom walk-in closet, spa-inspired 5-piece ensuite, gas fireplace, and serene backyard views. The fully finished lower level is ideal for multigenerational living, featuring a second kitchen, two additional bedrooms, a gym, wet bar, games area, and expansive recreation room. Step outside to your own private resort, where mature landscaping surrounds a saltwater pool, waterfall feature, and covered outdoor living area. A truly exceptional opportunity to own a custom estate property on one of Oakville's most prestigious streets, surrounded by luxury homes, steps to the lake, and moments to top-ranked schools, parks, and downtown Oakville. Some opportunities are measured in sq footage, others are measured in land, location and the life you'll build there. 1098 Lakeshore Rd is not to be missed. (id:5764)

1098 LAKESHORE Road West, Oakville

Listing courtesy of The Agency.

$1,798,800

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..

$5,998,000

6 Beds ⋅ 8 Baths ⋅ 40834825 MLS® #

Tucked behind stately gates and mature trees for exceptional privacy and security, this custom residence sits on just under half an acre and offers a timeless blend of elegant architecture and resort-inspired outdoor living in prime Southeast Oakville. Designed for both entertaining and everyday living with soaring ceilings, oversized windows and refined finishes which create a bright, sophisticated interior. At the heart of the home is a beautifully appointed chef’s kitchen with a large centre island, premium appliances, servery and a sun-filled breakfast area overlooking the backyard. Just beyond, the dramatic family room with ceiling height and a wood-burning fireplace creates a warm yet impressive gathering space. A true highlight of the home is the main floor primary suite - a rare and highly sought-after feature. Privately positioned and beautifully scaled, this serene retreat offers a spacious walk-in closet and spa-inspired ensuite, creating an ideal layout for long-term living. Thoughtfully designed mudroom/laundry with separate exterior access, garage entry and private access to the second-floor nanny suite complete the main level. The second level provides exceptional family accommodation with generously sized bedrooms, beautifully appointed bathrooms and a flexible in-law/nanny suite. The expansive lower level features a media room, recreation/games areas, wet bar, wine cellar, gym, additional bedroom and ample storage. Outdoors, the property transforms into a private backyard retreat, complete with mature landscaping, a spectacular in-ground pool, multiple seating and entertaining areas, and a charming, covered cabana/lounge designed for unforgettable summer entertaining. Located moments to the lake, top public and private schools, parks, shopping and commuter routes, this is a rare opportunity to own a gated estate in one of Oakville’s most prestigious neighbourhoods. (id:5764)

2096 LAKESHORE Road East, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$2,374,000

4 Beds ⋅ 2 Baths ⋅ 40831242 MLS® #

Bright, well maintained raised bungalow with a stunning backyard oasis available in the well sought out area of the West River neighbourhood. The eat-in sunroom kitchen is infused with natural light, with wraparound windows with views of the private backyard, a long peninsula quartz counter, pantry space, gas stove, reverse osmosis water system under kitchen sink, and patio doors out to decks, patios and an inground pool with spillover hot tub. Combination living room and dining room with built in bookcases is perfect for entertaining family and friends. Large primary bedroom with two other good size bedrooms with the 3rd bedroom currently being used as an office. 4 pc bathroom completes this floor. The finished basement features a den with gas fireplace, large sunlit bedroom, 3 pc bathroom, large rec room currently used as an office and laundry room with counter space and extra cupboards. The backyard gives you lots of options for entertaining or just hanging out. Decks, gazebo, raised reading nook, shed with thoughtfully landscaped mature gardens and trees offer a space to unwind, breath and relax. Walking distance to downtown Oakville, Vibrant Kerr Village, Oakville GO, Forster and Westwood Park and playground with splashpad, Public and school bus routes. (id:5764)

316 RIVER SIDE Drive, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$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..

Oakville Homes with a Pool for Sale

Newest Oakville Homes with a Pool for Sale

Contact Us

Services