Downtown Whitby Homes for Sale

Downtown Whitby Homes for Sale

Welcome to Downtown Whitby, a charming and vibrant neighborhood that beautifully blends the historic with the contemporary. Nestled in the heart of Whitby, Ontario, this area is characterized by its picturesque streets, rich heritage, and a strong sense of community. As you stroll through Downtown Whitby, you’ll discover an array of locally-owned shops, cozy cafés, and delightful restaurants, making it a perfect spot for both relaxation and socializing.

Families will appreciate the excellent educational institutions and parks that are easily accessible, fostering a welcoming environment for children and parents alike. The neighborhood is also well-connected, with easy access to public transit and major highways, making commuting a breeze for those who work in nearby cities.

For homebuyers, Downtown Whitby offers an impressive selection of homes for sale that cater to various lifestyles and budgets. From classic Victorian-style houses that echo the charm of yesteryears to modern townhomes and condominiums equipped with contemporary amenities, there’s something for everyone. The real estate market in this area is thriving, with properties that not only promise comfort but also the potential for investment growth.

Whether you are a first-time buyer, a growing family, or looking to downsize, Downtown Whitby presents an ideal place to call home. With its unique blend of urban convenience and suburban tranquility, this neighborhood is truly a gem in the heart of Ontario. Explore the possibilities today and discover why so many choose to make Downtown Whitby their home!

Newest Downtown Whitby Homes for Sale

$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
$699,900
3 Beds ⋅ 2 Baths ⋅ E13586798 MLS
Welcome to 560 Reynolds St. This warm & inviting home that has been lovingly cared for by the same family for over 40 years. Set in a wonderful, established family neighbourhood, this is a home filled with decades of happy memories & ready to welcome its next chapter. The comfortable layout offers 3 bedrooms, a bright living room, a sep dining room & an inviting eat-in kitchen. Updated flooring & carpeting throughout the main & upper levels bring a fresh feel to the home, while the finished basement provides valuable additional space for family activities, a home office or cozy retreat. Step outside to a private, pool-sized backyard with no neighbours behind, an increasingly rare find & a wonderful setting for children, pets, gardening or summer entertaining. The composite deck, redone in 2023, complete with built-in benches, offers the perfect place to relax, gather with friends or enjoy a quiet morning coffee.Thoughtful improvements include a heat pump in 2023, new front walkway in 2024, paved driveway in 2025, along with updated shingles (2025) and eavestroughs,(2025). The location is equally appealing. Peel Park is nearby, offering a splash pad, playgrounds, sports fields, tennis courts, baseball diamonds; activities for children of all ages. Iroquois Park Sports Centre, with arenas, pools, athletic facilities & year-round programming, is just a short drive away. In less than 10 minutes, you can be at Port Whitby Marina, enjoying one of Lake Ontario's finest natural harbours or walk & cycle along the scenic Waterfront Trail. Charming Downtown Whitby is also close at hand, with its historic architecture, locally owned shops, restaurants, theatre, library, museum & seasonal farmers' market. With excellent schools, shopping, churches & public transit nearby, as well as convenient access to Whitby GO Station and Highway 401, this well loved home offers a wonderful combination of comfort, community & convenience. Pre-listing home inspection available! Welcome home!

560 Reynolds Street, 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
$580,500
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
$799,000
3 Beds ⋅ 3 Baths ⋅ E13561592 MLS
Welcome to this beautifully maintained 3 bedroom, 3 bathroom detached two-storey home in one of Whitby's most established and sought after neighbourhoods. Rarely offered on this desirable street, this home backs directly onto Peel Park, providing no rear neighbours and immediate access to an incredible green space featuring baseball diamonds, tennis courts, soccer field, an outdoor rink, and more. Inside, you'll find a spacious and functional layout with generous principal rooms, hardwood flooring throughout the main floor, and fresh paint throughout, creating a bright, move-in ready home. The expansive main floor offers multiple living spaces, perfect for both everyday family living and entertaining. Upstairs features three well sized bedrooms, including a primary bedroom with an ensuite bathroom and laundry. The finished basement provides valuable additional living space ideal for a recreation room, gym or many other exciting opportunities. A portion of the garage has been thoughtfully converted into additional interior living space, offering added flexibility while retaining valuable garage storage. Combining an unbeatable location, a family-friendly layout, and a picturesque park setting, this is a rare opportunity to own a home on one of Whitby's most coveted streets. Don't miss your chance, homes like this don't come along often.

518 Reynolds Street, 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
$929,900
6 Beds ⋅ 3 Baths ⋅ E13532048 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, cafés, 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
$2,299,900
5 Beds ⋅ 4 Baths ⋅ E13519274 MLS
Amazing location! This exceptional custom home with over 5,000 sq ft of total living space features 4+1 bedrooms, 4 bathrooms, a finished in-law suite, and a detached 2-storey carriage house offering incredible flexibility. The natural stone exterior, cedar shake siding and roof, professionally landscaped grounds, stone walls, and gated entrance create outstanding curb appeal. Enjoy a private backyard oasis complete with irrigation, landscape lighting, a tranquil fountain, and a wood-burning outdoor fireplace. Inside, soaring and tray ceilings, crown moulding, custom wood paneling, solid wood doors, wood-framed windows, designer lighting, hardwood flooring, and a striking herringbone-tiled foyer showcase exceptional craftsmanship. The chef's kitchen features premium Sub-Zero, Wolf, and Cove appliances, marble countertops and backsplash, custom solid wood cabinetry with illuminated glass display cabinets, a large centre island, and a butler's pantry. French doors from the breakfast area open to the beautifully landscaped backyard. The living room features a wood-burning fireplace, while the dining room is perfect for entertaining. The luxurious primary suite offers designer lighting, a spa-inspired ensuite and large walk-in closet. An upper-level fitness room with a built-in sauna creates a private wellness retreat. The lower level includes an in-law suite with a bathroom, kitchenette, laundry, slate flooring and a wood-burning fireplace. The heated and air-conditioned carriage house features vaulted ceilings, a wood-burning fireplace, Saltillo tile, hardwood flooring, and custom wood staircases. Additional highlights include hardwired security with cameras, a full-home generator, multiple laundry areas, a cold room, and countless luxury upgrades. Located in a coveted historic downtown neighbourhood with mature, tree-lined streets, this home offers easy walking to restaurants, shops, and cafés. Ideal for commuters close to the GO Train and Highway 401.

505 King Street, 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
$924,900
2 Beds ⋅ 2 Baths ⋅ E13487684 MLS
Welcome to This Mid Century Modern Rancher In The Heart Of Desirable Historic Downtown Whitby. A Quiet Picturesque Neigborhood Full Of Mature Trees, Walk To GO Station, Downtown Shopping , Library, Parks And More. Quick 401 Access, Ideal For Commuters. Lovingly Maintained 2 Bedroom Bungalow On Oversized Rare 81' x 136 ' Lot Landscaped With Perennials, Shrubs And Shade Trees. Long Brick Walkway Leads You To The Large Entryway Of This Sunny Home. Open Concept Floor Plan Includes Spacious Main Living Room With Hardwood Floors, Original Wood Burning Fireplace And HUGE Windows, Open To Large Formal Dining Room For Family Dinners. Kitchen Boasts Gas Stove, Stainless Steel Appliances And Breakfast Room With Built-In Banquette Seating And Double Garden Doors To Expansive Backyard. Huge Primary Bedroom Is An Incredible Sanctuary With Sunken Sitting Area, Electric Fireplace And Double Doors With Views To The Gorgeous Gardens. 2nd Bedroom Is Nicely Sized With Full Length Wardrobe And Large Window. Recently Updated Main Bath Features Porcelean Tile, A Custom Walk In Shower, Built-In Bench And Rain Head. Substantially sized Recreation Room On The Lower Level With Gas Fireplace, Premium Lanmiate Floors And 3 Piece Bathroom. Breath Taking Private, Fully Fenced Park Like Backyard With Beautiful Perennial Gardens, Composite Deck, Interlock Brick Patio, Water Feature & Garden Shed. Great For BBQ'ing, Entertaining Or Just Enjoy The Birds & Wild Life On Your Own. You Need To View It To Appreciate It!

801 King Street, Whitby
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