Downtown Whitby Homes for Sale

Downtown Whitby Homes for Sale

Welcome to Downtown Whitby, a vibrant and charming neighborhood that perfectly blends historical charm with modern conveniences. Nestled in the heart of Whitby, Ontario, this area is known for its rich heritage, tree-lined streets, and a welcoming community atmosphere. With an array of shops, cafes, and restaurants, Downtown Whitby offers residents a vibrant lifestyle filled with local flavor and unique experiences.

One of the standout features of this neighborhood is its accessibility. With easy access to major highways and public transit options, commuting to Toronto or other neighboring cities is a breeze. Families will appreciate the proximity to excellent schools, parks, and recreational facilities, making it an ideal place to raise children.

The real estate market in Downtown Whitby is thriving, with a diverse selection of homes for sale that cater to various lifestyles and budgets. From charming century-old houses that exude character to modern townhomes and condominiums offering contemporary living, there’s something for everyone. Many of these homes boast beautiful gardens, spacious layouts, and modern amenities, ensuring comfort and style.

As you explore the streets of Downtown Whitby, you’ll discover a strong sense of community, with regular events and activities that bring neighbors together. Whether you’re looking for a bustling urban lifestyle or a peaceful retreat, Downtown Whitby has it all. Don’t miss your chance to find your dream home in this delightful neighborhood, where history meets modern living and community spirit thrives. Your new adventure awaits in Downtown Whitby!

Newest Downtown Whitby Homes for Sale

$500,000
3 Beds ⋅ 1 Baths ⋅ E13666876 MLS
Detached 1.5 story house in fabulous area of Whitby on a great lot including a detached double car garage. This home features a cozy kitchen with laminate flooring, a window and a built in dishwasher. Living room with hardwood flooring, picture window and is a formal room. Dining room with hardwood flooring, window and is a formal room. Primary bedroom with hardwood flooring, closet and a window. Second bedroom with hardwood flooring, closet and a window. Lower level recreation room with broadloom, bar and a window. Third bedroom in the lower level with broadloom, closet and a window. Lots of parking. Covered porch at the back of the house. Large back deck perfect for entertaining. Close to all amenities: schools, shopping and transit.

1106 Green Street, Whitby
$999,900
5 Beds ⋅ 3 Baths ⋅ E13652246 MLS
Exceptional Ravine Retreat with Incredible Multi-Generational & Investment Potential! Nestled on a premium ravine lot in the heart of Whitby, this unique hillside bungalow offers 2485sqft of living space over three finished levels of versatile living space designed to adapt to your family's needs. Featuring 5 spacious bedrooms, 3 bathrooms, multiple living areas, with each level having it's own separate entrance, this home presents an outstanding opportunity for multi-generational families, investors, or those seeking future income potential. The main level offers an inviting open-concept layout with a family-sized eat-in kitchen complete with Stainless Steel Appliances, Lots of Cupboards & Granite Countertops. Spacious living & dining areas, and a walk-out to a spectacular multi-level deck with gas hook-up overlooking the tranquil ravine, the perfect relaxing or entertaining spot. The primary bedroom features its own ensuite, while two additional bedrooms and a full bathroom complete the main level. The bright walk-out lower level includes two additional bedrooms, a full bathroom, an expansive family room with fireplace, and direct access to the multi-level deck. The finished basement offers a large recreation room with walk-out to a private patio, creating additional flexible space for extended family, home office, recreation, or future living quarters. Built into a natural slope, each of the home's three levels enjoys its own exterior entrance, making this an exceptional candidate for extended families, in-law living, or future income-generating. Enjoy the privacy of a ravine, mature trees, and peaceful outdoor living from every level while remaining just minutes from Downtown Whitby, GO Transit, Highway 401, schools, parks, restaurants, shopping, and every major convenience. A rare opportunity offering lifestyle, flexibility, and long-term investment potential in one of Whitby's most desirable established neighborhoods.

81 Garden Street, Whitby
$905,000
6 Beds ⋅ 3 Baths ⋅ E13641874 MLS
Nestled on a quiet, tree-lined street in one of Downtown Whitby's most established and desirable neighbourhoods, this beautifully maintained 4-bedroom home offers the perfect blend of character, comfort, and modern updates. Surrounded by mature trees and spacious lots, you're just steps to Trafalgar Castle School, parks, trails, and the shops, cafes, and restaurants of vibrant Downtown Whitby, with convenient access to Highways 401, 412, and the Whitby GO Station. Inside, thoughtfully updated living spaces are designed for today's lifestyle. The bright, functional kitchen showcases quartz countertops, stainless steel appliances, and overlooks the private backyard oasis completed with a heated salt water pool, making it easy to stay connected whether you're preparing meals or entertaining guests. The spacious primary suite is a true retreat, featuring a walk-in closet and a beautifully renovated ensuite. The basement includes two large bedrooms and a small unfinished space awaiting your touches. This is an exceptional opportunity to own a move-in-ready home in one of Whitby's most sought-after neighbourhoods. Windows. A/C, Furnace all less than 5 years old! Move in ready home!

523 Reynolds Street, Whitby
$639,900
3 Beds ⋅ 1 Baths ⋅ E13638502 MLS
Updated 3 bedroom, 1 bathroom home in a prime location, directly across from Rotary Centennial Park. This move-in ready property is a fantastic opportunity for first-time buyers or downsizers seeking the convenience of one-level living, with primary bedroom, bathroom, and laundry all located on the main floor. Recent updates include a new furnace (2024), roof (2024), hot water tank (2022), 100-amp electrical service, windows (2014), and A/C (2013). Brand new patio doors (2026) lead to a spacious back deck overlooking the fully fenced backyard, complete with beautiful gardens, the perfect setting for relaxing or entertaining. Inside, the bright and functional layout features a modern kitchen, and clean, well-maintained interior. Upstairs offers two additional bedrooms, ideal for family, guests, or a home office. The clean basement provides excellent storage space. Conveniently located with easy access to Highway 401 and a 5-minute drive to the GO Station. Pre-list home inspection available.

810 Byron Street S, Whitby
$749,999
4 Beds ⋅ 2 Baths ⋅ E13634798 MLS
Welcome to this beautiful Bungalow corner lot with a lot of sunlight which 61 x 146 size lot adds value in a quite and beautiful neighbourhood. It features a 3+1 bedroom and 2 bathrooms, an attached garage with mezzanine, inground pool, an incredible private backyard w/ 2 deck areas. Kitchen consists of granite countertop, Stainless Steel range hood and open to living room area. Gas fireplace in the living room provide cozy evenings. Separate entrance and through house gives access to a partly finished basement that consists of 3-pcs bathroom, bedroom, entertainment/family/rec room and laundry room. A/C installed in June 2023, brand new owned hot water tank was replaced in July 2026.

505 Colborne Street E, Whitby
$899,900
4 Beds ⋅ 2 Baths ⋅ E13601138 MLS
Fully Renovated All-Brick Home With High Quality Modern Finishes! Hardwood On Main Floor With Tons Of Natural Light Throughout Home. All-White Renovated Kitchen Combined With Dining Room & Double-Door Walkout To Yard. Very Private And Lush Backyard Oasis, Featuring Two Decks And A Cement Floor Shed/Gazebo Bar. Fully Finished Basement With Pot Lights And Gorgeous Bathroom. This Home Has Great Flow And Smart Use Of Space. Walking Distance To Downtown Whitby And All The Town Has To Offer!

514 Ash Street, Whitby
$625,000
5 Beds ⋅ 2 Baths ⋅ E13598134 MLS
Welcome to 1014 Dunlop Street East! Ideally located in South Whitby with quick access to Hwy 401, Whitby GO Station, shopping, parks, schools, and everyday amenities, this versatile home offers exceptional value for investors, first-time buyers, downsizers, or multigenerational families. This 3+2 bedroom, 2 bathroom home features a functional layout, parking for 2 vehicles, a generous backyard, and an in-law suite with a separate entrance - offering income potential or flexible living arrangements. The bright main floor features an open-concept living and dining area, an updated kitchen, and three well-sized bedrooms, each with a closet. One bedroom offers a walkout to the backyard, creating the perfect space to enjoy your morning coffee or unwind in the evening. The finished lower level includes a separate entrance, above-grade windows, bright kitchen/living/dining areas, two spacious bedrooms, a 4-piece bathroom, and abundant storage, making it ideal for extended family, guests, or potential rental income. Step outside to a fully fenced backyard featuring a large deck and plenty of green space for children and pets to play. Whether you're entertaining friends, relaxing with family, or looking for a home with built-in income potential, this property offers outstanding flexibility in a convenient, commuter-friendly location. Shingles (2025), eavestroughs (2019), windows (2016). *Most interior photos have been virtually staged.

1014 Dunlop Street E, Whitby
$568,900
2 Beds ⋅ 2 Baths ⋅ E13585722 MLS
Location - Location - Location!! Perfect for First time Home buyers, Renovators, Builders or Empty Nesters. Homes do not become available too often in this desirable area. This lovely detached bungalow in an ideal location is close to amenities, GO Station, walking distance to schools, parks, recreation, downtown. This Home features two bedrooms upstairs with and open concept dining/family room, the living & dining rooms that are both enhanced by large windows offering plenty of natural light & a warm, inviting feel along with a walkout to a massive Private Backyard with Mature Trees, Perfect FOR ENTERTAINING!! Separate side entrance leads to the basement. Roof and furnace is newer and in great condition. YOU ARE JUST MINUTES TO THE POPULAR PEEL PARK , THIS HOME has a TON of potential ! Opportunities like this are rare. So please do not miss out!!!!

917 Green Street, Whitby
$549,900
5 Beds ⋅ 2 Baths ⋅ E13578022 MLS
Welcome to 322 Rosedale Drive, Whitby! Nestled in a mature, family-friendly neighbourhood, this 3-bedroom, 2-bathroom semi-detached bungalow offers an exceptional opportunity for first-time buyers, investors, or anyone looking to add their own personal touch. With approximately 1,040 sqft above grade, plus a partly finished basement, this home features a functional layout with endless potential. The bright, open-concept living and dining area showcases hardwood floors and a charming bay window overlooking the front garden. The updated kitchen is equipped with quartz countertops, a breakfast bar, stylish backsplash, large pantry, and ample cabinetry, making it both functional and inviting. The partly finished basement expands the living space with a spacious rec room featuring a large above-grade window, an additional room ideal for a home office, gym, or hobby room, and a separate side entrance offering excellent in-law suite or income potential. Ideally located just minutes from highly rated schools, parks, shopping, transit, and everyday amenities, this home combines a desirable location with solid bones and outstanding potential. Whether you're looking to renovate, customize, or invest, this is a fantastic opportunity to build equity in one of Whitby's established communities.

322 Rosedale Drive, Whitby
$649,900
4 Beds ⋅ 2 Baths ⋅ E13570064 MLS
Welcome to 341 Rosedale Drive in Whitby! Situated in a desirable family-friendly neighborhood, this 3+1 bedroom, 2 bathroom bungalow offers an excellent opportunity for first-time buyers, investors, or those looking to add their own personal touches. Featuring approximately 1,012 sq. ft. above grade (plus a partly finished basement), the home offers a functional layout with plenty of potential. Roof 2013.Enjoy the privacy of having no neighbor's behind while being just minutes from highly rated schools, parks, shopping, and everyday amenities. The basement features a spacious rec room with a cozy gas fireplace, a 3-piece bathroom, an additional room ideal as a fourth bedroom, home office or hobby room, and a separate side entrance offering excellent in-law or income potential (subject to any required approvals).With solid bones, a sought-after location, and endless possibilities, this is a fantastic opportunity to renovate, customize, and build equity in one of Whitby's established neighborhood.

341 Rosedale Drive, Whitby
$924,900
3 Beds ⋅ 3 Baths ⋅ E13534102 MLS
22 Ladies College Drive is a showpiece of timeless elegance, nestled beneath a canopy of mature trees in one of Downtown Whitby's most prestigious and sought-after neighbourhoods. From the moment you arrive, the exceptional curb appeal and meticulously landscaped grounds set the stage for what awaits inside. Beautifully finished from top to bottom, this impressive 3-bedroom home (easily converted back to 4 bedrooms) showcases quality craftsmanship and thoughtful upgrades throughout. The heart of the home is the stunning gourmet kitchen, featuring quartz countertops, a centre island with breakfast bar, custom cabinetry with built-in pantry, and an open-concept design that flows effortlessly into the spacious dining area-perfect for everyday living and entertaining. The inviting living room with gleaming hardwood floors offers an elegant space to gather, while the cozy family room with gas fireplace and garden door walk-out leads to your own private backyard retreat. Designed to impress, the award-worthy landscaping surrounds a heated inground pool with a brand-new liner and brand new rubberized pool decking (2026), newly resurfaced deck boards (2026), louvered pergola (2026), and multiple areas to relax, entertain, and enjoy summer days in complete privacy. The primary suite offers a walk-in closet and beautifully appointed 3-piece ensuite, creating the perfect place to unwind. The professionally finished lower level extends the living space with a generous recreation room featuring a stylish wet bar with built-in cabinetry, dedicated games area, recessed illuminated poster displays, built-in desk ideal for working from home, and abundant storage. Ideally located just minutes from Trafalgar Castle School, parks, walking trails, the charming boutiques and restaurants of vibrant Downtown Whitby, Highway 401, and the Whitby GO Station, this exceptional home perfectly combines luxury, comfort, and convenience.

22 Ladies College Drive, Whitby
$899,900
3 Beds ⋅ 2 Baths ⋅ E13513388 MLS
Located In The Heart Of Historic Downtown Whitby, This Exceptional Century Home Offers The Perfect Blend Of Timeless Character And Modern Comfort. Stroll To Local Cafés, Restaurants, Boutique Shopping, Parks And Community Events, With The Whitby GO Station Just Minutes Away For An Easy Commute. Set On A Private Corner Lot, The Beautifully Landscaped Grounds Feature A Stunning Inground Pool (New Liner 2023), Covered Gazebo, Entertaining Deck And Multiple Outdoor Spaces Designed For Relaxing And Gathering. The Original Century Cottage Showcases 10-Foot Ceilings, Oversized Windows And The Warmth And Craftsmanship Only A Home Of This Era Can Offer. 3 Generous Bedrooms Are Complemented By An Oversized Bathroom Featuring A Classic Clawfoot Tub And Walk-In Glass Shower. The Heart Of The Home Is A Beautifully Designed Vintage-Inspired Kitchen With Granite Countertops And Quality Stainless Steel Appliances, Opening To Inviting Living And Dining Spaces. A Thoughtfully Designed Addition, Completed In 2002, Creates An Entirely New Experience. Here You'll Find Main Floor Laundry, A Powder Room, Mudroom With Direct Access To The Pool, And An Extraordinary Second-Storey Family Room With Vaulted Ceilings, A Gas Fireplace And Walls Of Large Windows Overlooking The Treetops. Bathed In Natural Light, It Offers Beautiful Views Over The Pool And Private Courtyard Below, Creating A Space Unlike Anything Else On The Market. Bonus Finished Basement With Extra Tall Ceilings & Large Windows. Practicality Meets Charm With A Side Driveway, Detached Garage And Parking For 3 Vehicles. While The Home's Century Character Has Been Beautifully Preserved, Extensive Mechanical And Electrical Updates Provide The Confidence And Convenience Of Modern Ownership. Rich In History, Full Of Personality And Impossible To Replicate, This Is A Rare Opportunity To Own One Of Downtown Whitby's Truly Special Homes While Embracing One Of Durham Region's Most Sought-After Walkable Lifestyles!

400 Byron Street S, Whitby
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