Oak Bay Homes with Character Design

Welcome to Oak Bay, a charming seaside community nestled on the southern tip of Vancouver Island in British Columbia. Renowned for its stunning ocean views, vibrant arts scene, and rich history, Oak Bay offers a unique blend of small-town charm and urban sophistication. With its tree-lined streets and picturesque waterfront, residents enjoy a tranquil lifestyle while being just a short drive from the bustling city of Victoria.

One of the standout features of Oak Bay is its stunning collection of homes with character design. This enchanting neighborhood boasts an array of architectural styles, from classic heritage houses to contemporary masterpieces, all harmoniously integrated into the natural landscape. Many of these homes reflect the area's rich history, showcasing intricate craftsmanship and timeless elegance that captures the essence of coastal living.

As you stroll through Oak Bay, you’ll be captivated by the beautifully maintained gardens and vibrant community spirit. The local shops, cafés, and art galleries create a lively atmosphere, making it a perfect place for both families and retirees. Outdoor enthusiasts will appreciate the abundance of parks, beaches, and recreational activities, including kayaking, golfing, and scenic walking trails along the coastline.

Living in Oak Bay means embracing a lifestyle that values community, nature, and architectural beauty. Whether you’re looking for a cozy bungalow or a grand family estate, the homes in this area offer character and charm that truly set them apart. Discover the magic of Oak Bay, where every home tells a story and every street invites you to explore. Your dream home awaits in this picturesque coastal haven!

Newest Oak Bay Homes with Character Design

$1,799,000

4 Beds ⋅ 2 Baths ⋅ 1043967 MLS

By Appointment Only - Classic South Oak Bay living with the space and flexibility today’s families want. Located in one of Victoria's most sought-after neighbourhoods, this updated character home blends charm with thoughtful upgrades. The main level is designed for connection, with a renovated open-concept kitchen, dining area, and living room centred around a wood-burning fireplace. French doors open to a west-facing deck and heated patio, ideal for summer dinners and easy indoor-outdoor entertaining. Upstairs are two spacious bedrooms, while the lower level offers two more bedrooms and a generous rec room, perfect as a children’s play space, media room, or teen retreat. A backyard studio adds flexibility for a home office, gym, or creative space. Enjoy renovated bathrooms, heated tile baths, HVAC heating/cooling, newer appliances, custom finishings, garage, storage, fenced yard, driveway, re-stuccoed exterior, and recent survey. Close to beaches, parks, schools, and Oak Bay Village.

916 Monterey Ave, Oak Bay

Courtesy of RE/MAX Camosun

$1,650,000

4 Beds ⋅ 3 Baths ⋅ 1043580 MLS

This lovingly cared for 4 bedroom, 3 bathroom Oak Bay character home has come to market for the first time in 70 years, w/a 3 bed, 1 bath main living area w/a full height 1 bed, 1 bath walkout suite. This beautiful home has undergone extensive renovations, incl. complete foundation replacement & excavation resulting in the 8' lower level, hurricane strapping, new perimeter drains, plumbing upgrades, 200 amp service, new gas furnace & HVAC & renovated main level w/new kitchen. Enjoy the modern comforts of these upgrades in a home rich w/character, natural light & spaciousness. The upper level has 3 large bedrooms w/a 4pc bath, ideal for a family. The private, fully-fenced yard has direct access via the deck off the kitchen, perfect for summer entertaining & kids. The home has plenty of storage, closets throughout & spacious driveway parking. Bring your ideas to the unfinished bsmt area, ready for additional bedrooms, bathrooms or flex space. This home is a rare offering & a must-see!

1597 Monterey Ave, Oak Bay

Courtesy of Coldwell Banker Oceanside Real Estate

$3,649,900

5 Beds ⋅ 3 Baths ⋅ 1043163 MLS

Rising above the Juan de Fuca Strait in Oak Bay's Harling Point neighbourhood, this remarkable home pairs panoramic Olympic Mountain views w/ architectural character and refined contemporary design. Extensively upgraded over the past 3 years, the custom Douglas Grant kitchen features marble countertops, premium appliances, and herringbone oak flooring. The primary suite offers vaulted ceilings, sweeping strait views, and a multi-room ensuite. French doors connect the main living areas to an ocean-view deck and a south-facing garden patio beneath Walbran Park, extending the private backyard outdoors. Rear parking provides stair-free entry and convenient main-level living, while integrated UniFi WiFi, smart-home features, privacy-focused security, and weather-aware irrigation round out the home's systems. Just a short walk to Gonzales Beach, this Harling Point home offers elegant, oceanside living on one of Canada's most desirable streets.

100 King George Terr, Oak Bay

Courtesy of Oakwyn Realty Ltd.

$3,175,000

5 Beds ⋅ 5 Baths ⋅ 1043040 MLS

One of Oak Bay’s finest ARTS AND CRAFTS character homes built in 1913, steeped in history, beautifully maintained and updated by a master craftsman. Positioned on a quiet, tree-lined street within the very heart of South Oak Bay. The residence is beautifully framed within the streetscape as the front entryway borders the mature landscaping and perennial gardens. A large entry hall invites you into the spacious principal rooms overflowing with character. Features include inlaid oak flooring, coffered ceilings, wainscotting, bay windows and lovely, original stained and leaded glass. The bright, spacious, modern kitchen fits with the grand character. Upstairs are three corner bedrooms and two bathrooms, the principal bedroom features a walk-in closet and modern ensuite. A sky-lit upper loft is made for an exercise room or child’s play area. The full height lower floor includes a separate two-bedroom guest suite, spacious den and office with a separate entrance from the back garden.

1043 St. Patrick St, Oak Bay

Courtesy of Newport Realty Ltd.

$2,489,000

4 Beds ⋅ 4 Baths ⋅ 1042541 MLS

Set on a quiet, tree-lined curve in the heart of the Uplands, this classic Tudor offers timeless architecture, exceptional privacy, and a rare sense of calm. The home blends storybook charm with light-filled interiors and thoughtful updates that respect its original character. Warm hardwood floors and generous principal rooms create an inviting atmosphere for everyday living and entertaining. The living and dining areas flow naturally, anchored by traditional fireplaces and large windows that fill the home with soft natural light. Upstairs features peaceful, well-proportioned bedrooms, including a spacious primary ideal for family, guests, or a home office. The lower level includes a comfortable rec room, and benefits from a separate exterior entrance. Outdoors, the southwest-facing backyard enjoys wonderful afternoon and evening sun providing privacy and tranquility. A true Uplands classic, offering architectural beauty, functional living space, and enduring appeal.

3400 Upper Terrace Rd, Oak Bay

Courtesy of The Agency

$1,580,000

5 Beds ⋅ 4 Baths ⋅ 1042420 MLS

Oak Bay Character. Beautifully re-imagined, this 1931 residence blends timeless charm with the comfort & efficiency of modern family living. Fully renovated with permits in 2018, the home retains much of its original character while offering a bright, contemporary interior designed for today’s lifestyle. The sunny open plan layout centres around a crisp white kitchen with entertainment-sized island, stainless steel appliances & seamless flow to the principal living spaces filled with natural light throughout the day. A main floor primary suite provides convenience for families of all stages. Upstairs are 2 bedrooms & a 2-piece bathroom, while the lower level mirrors the accommodation with excellent suite potential for extended family or additional income. An attached single car garage. The large, level property is fully fenced-ideal for children and pets alike. Perfectly located within walking distance of Estevan Village & a short hop to UVic.

2052 Carrick St, Oak Bay

Courtesy of Sotheby's International Realty Canada

$2,299,900

3 Beds ⋅ 4 Baths ⋅ 1042063 MLS

Nestled on a beautifully landscaped 10,000+ sq ft lot in the heart of South Oak Bay, this timeless character home blends classic charm w/ thoughtful modern updates. Offering over 2,400 sq ft, the home features 3 bedrooms, each w/ its own ensuite, including a spacious main-level primary retreat. Bright, inviting living & dining rooms flow into the updated kitchen, while French doors open to a sunny deck & private backyard, ideal for entertaining or quiet mornings. A family room, powder room & mudroom complete the main level. Upstairs, 2 generous bedrooms w/ renovated ensuites provide excellent space for family or guests. Detached double garage w/ rear lane access. Just one block to the ocean & moments from Victoria Golf Club, Oak Bay Beach Hotel, Oak Bay Marina & McNeill Bay. A fantastic opportunity to enjoy the character of a classic Oak Bay home in one of the area's most coveted neighbourhoods.

1036 Deal St, Oak Bay

Courtesy of The Agency

$1,699,900

4 Beds ⋅ 4 Baths ⋅ 1041992 MLS

NEW PRICE! Prime Oak Bay living in an unbeatable location. Situated in the heart of Oak Bay, just steps to Estevan Village, Uplands Park, and Willows Beach, this beautifully updated 4 bed, 4 bath home offers the perfect blend of lifestyle, convenience, and coastal charm. Featuring elegant inlaid hardwood flooring, two fireplaces, updated thermopane windows, and abundant natural light throughout. The thoughtfully designed kitchen includes oversized drawers, pull-out pantry shelving, and opens seamlessly to the bright family room. Step outside to a quiet west-facing private backyard retreat filled with sunshine and serenity. Added value with a 2-bedroom mortgage helper and fully serviced detached garage. A rare opportunity in one of Victoria’s most sought-after neighbourhoods.

2758 Dunlevy St, Oak Bay

Courtesy of RE/MAX Camosun

$3,590,000

5 Beds ⋅ 6 Baths ⋅ 1041918 MLS

EXCEPTIONAL OAK BAY FAMILY HOME situated in the one of the most desirable neighbourhoods of Victoria! An easy walk to Uplands Park, Willows Beach and Estevan Village. Custom designed throughout with outstanding finishing and superior attention to detail boasting 10ft ceilings on main and upper levels, chef’s kitchen with beautiful appliances, 5 bedrooms, an office and 6 baths elegantly assembled over 4779 SQFT. The light oak flooring weaves its way throughout the home. The Butler’s pantry has a second dishwasher and connects the dining room and the kitchen. Upper level has 3 bedrooms, each with ensuite & heated marble tile floors, master is magnificent with the ultimate in relaxation deep soaker tub and walk in marble shower. The lower level has 9ft ceilings with an entertainment room complete with wet bar and built in sound, two bedrooms and two 5 piece baths. Sunny back yard is fully fenced. 2 heat-pumps ensure all season comfort. August occupancy! Call today to arrange your tour!!

2777 Dewdney Ave, Oak Bay

Courtesy of Sutton Group West Coast Realty

$1,625,000

3 Beds ⋅ 2 Baths ⋅ 1041572 MLS

Located in one of South Oak Bay's most sought-after locations, on a quiet country-lane road of peaceful properties, this mid-century modern, solid, family home offers many lifestyle options. Set well back at a pleasing elevation, the home offers generously proportioned, bright, light filled rooms. The blissfully private, 1/4 acre plus, mostly rock garden is west facing and provides a perfect oasis of serenity with interesting elevations and plantings. Deserving your attention and ideas, this is a perfect opportunity to fulfill your dream in this prestige location close to Victoria's finest private and public schools, parks, beaches, Victoria Golf Club and all amenities.

930 Runnymede Pl, Oak Bay

Courtesy of Royal LePage Coast Capital - Oak Bay

$2,499,900

4 Beds ⋅ 2 Baths ⋅ 1039721 MLS

European-inspired elegance meets modern living in this exceptional South Oak Bay residence. Situated on a quiet side street just steps from Oak Bay village, parks, schools, transit, & the waterfront, this beautifully updated home seamlessly blends timeless character with contemporary comfort. The stunning open-concept kitchen addition in 2023 by Villamar features premium Miele & KitchenAid appliances, custom cabinetry, coffered ceilings, & Hunter Douglas blinds throughout. Major upgrades include electrical, kitchen area infloor heated windows, Boiler for Heating, updated perimeter drains, & new basement flooring. The detached garden suite with a 4-piece bath offers outstanding flexibility as a guest retreat, home office, studio, or space for extended family. Outside, enjoy a professionally redesigned garden by Demitasse Landscapers featuring a pond, fountain, irrigation, & night lighting. move-in-ready home in one of Victoria's most coveted neighbourhoods.

2366 Zela St, Oak Bay

Courtesy of RE/MAX Camosun

$4,850,000

3 Beds ⋅ 3 Baths ⋅ 1040157 MLS

Set on one of South Oak Bay’s most coveted streets, this beautifully maintained residence offers over 3,200 sq ft of living space and timeless architectural appeal. Rich in character, the home features soaring ceilings, graceful archways, leaded glass accents, detailed woodwork, and hardwood floors throughout. The main level is designed for both everyday living and entertaining, offering gracious living and dining rooms, a spacious kitchen w/eating area, family room, office, and seamless access to multiple patios and beautifully landscaped gardens. Upstairs, the primary retreat enjoys views toward Victoria Golf Club and the ocean, complete w/a sitting area, walk-in closet, and ensuite. Two additional bedrooms, a full bathroom, and a dedicated laundry complete the upper level. An unfinished lower level provides excellent storage space. Perfectly positioned moments from Victoria Golf Club, Oak Bay Village, parks, beaches, and the waterfront.

318 Newport Ave, Oak Bay

Courtesy of The Agency

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