Map location of Winchester Rd. / Ashburn Rd

Winchester Rd. / Ashburn Rd, Whitby, ON, Canada

Winchester Rd. / Ashburn Rd - Nearby Homes for Sale

Name: Winchester Rd. / Ashburn Rd
Address: Whitby, Ontario, Canada

Whitby, Ontario, Canada

Living Near Winchester Rd. / Ashburn Rd

Buyers searching for homes near Winchester Rd. / Ashburn Rd usually want two things: access and context. This page is built to make that comparison easier by combining available listings, street-level location details, and nearby amenities in one place. Instead of jumping between different tools, you can review homes and local points of interest side by side, then decide which streets or neighborhoods match your priorities. For Whitby, ON, that means you can quickly compare options around a known destination before spending time on private tours.

Right now, this page shows 18 nearby homes and 20 surrounding points of interest. You can use the listing table to compare address, bed and bath counts, and list price, then use the categories section to understand what types of amenities are clustered around the area. Top nearby category signals include Transport. This structure helps you compare convenience, neighborhood activity, and market options without leaving the page.

If you are relocating or narrowing your search, start with the homes shown here, then expand your review to nearby categories and additional location details. This workflow gives a more complete picture than price alone and helps avoid shortlisting homes that do not fit your day-to-day needs. Availability and pricing can change quickly, so checking this page regularly is useful when you are actively searching near Winchester Rd. / Ashburn Rd. Once a property looks promising, contact an agent to confirm the latest status and schedule a showing.

Frequently Asked Questions

How many homes are currently listed near Winchester Rd. / Ashburn Rd?

There are currently 18 active or coming-soon homes displayed near Winchester Rd. / Ashburn Rd on this page.

What information does this page include for homes near Winchester Rd. / Ashburn Rd?

This page includes nearby home listings, home prices, bedroom and bathroom counts, and nearby points of interest around Winchester Rd. / Ashburn Rd in Whitby.

How can I compare neighborhoods around Winchester Rd. / Ashburn Rd?

Use the nearby homes table and points-of-interest sections to compare listing prices, surrounding amenities, and local access points before scheduling a tour.

Homes for sale near Winchester Rd. / Ashburn Rd, Whitby, ON, Canada

Address	Bed / Bath	Listing Price
76 VIPOND ROAD Welcome to this beautifully upgraded Brooklin family home, where luxury finishes, functional living spaces, and exceptional entertaining areas come together perfectly! This stunning 3-bedroom, 4-bath detached home offers impressive curb appeal with professionally landscaped front and back gardens, p Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,099,900
133 TREMOUNT STREET Welcome to this well maintained 3+1 bedroom, 4 Wash room all-brick detached family home is nestled in a quite, family friendly desirable Brooklin, Whitby; Offering an exceptional value, this two-storey home features a double-car garage; highlighted by an extended-height living room with a cozy gas f Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 4 Baths	$879,900
38 ROBMAR STREET E Absolutely Stunning 5+2 Bedroom Custom Executive Home in Sought-After Brooklin! Thisone-of-a-kind estate showcases luxury living with high-end finishes and exceptional attentionto detail throughout. Featuring a grand entrance, formal dining room, and a custom gourmeteat-in kitchen with top-of-the-li Whitby (Brooklin), ON Living Area: Sqft.	7 Beds, 6 Baths	$1,799,000
144 UNDERWOOD DRIVE Exceptional Custom-Built Brooklin Family Home! This beautifully appointed 4-bedroom, 4-bathroom home offers the perfect combination of luxury, comfort, and functionality. Step outside to your maintenance-free backyard oasis featuring premium artificial turf, a relaxing hot tub, an expansive entertai Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,199,000
8 ST AUGUSTINE DRIVE Discover this stunning new 2-bedroom bungalow by DeNoble Homes, perfectly situated across from Winchester Park! Thoughtfully designed with premium upgrades, the home boasts 10-ft smooth ceilings and a bright, open layout. The kitchen impresses with high-end cabinetry, a pantry, quartz counters, a ce Whitby (Brooklin), ON Living Area: Sqft.	2 Beds, 2 Baths	$1,269,990
12 LONETTO STREET Luxury isn't defined by square footage-it's defined by craftsmanship, thoughtful design, and enduring quality. The Mozart A embodies this philosophy, offering an elegant bungalow that blends timeless architecture with the exceptional attention to detail for which DeNoble Homes is renowned. Built by Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 3 Baths	$1,419,990
59 BAGOT STREET This exceptional century home is a must see, offering a blend of classic charm with a designer's touch, set on a quiet, oversized corner lot along one of Brooklin's most historic and desirable streets. Just steps from top-rated schools, the public library, and the vibrant shops, cafes, and restauran Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 2 Baths	$1,208,889
31 LONETTO STREET LIST PRICE IS NET OF THE APPLICABLE HST HOUSING REBATE, SUBJECT TO PURCHASER ELIGIBILITY. Built by award-winning Delta-Rae Homes, this beautifully designed bungalow features 10' smooth ceilings on the main floor, an open-concept layout, and quality finishes throughout. The kitchen and bathroom vanit Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 3 Baths	$1,529,990
16 CODY AVENUE Stunning 3+1 bedroom Meadowcrest Model by Melody Homes, offering approximately 2, 800+ sqft of total living space! This all-brick family home features a bright and inviting foyer with soaring 11-ft ceilings leading to the sun-filled formal living and dining rooms, both finished with gleaming hardwoo Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 3 Baths	$999,900
1 QUEEN STREET Investors, builders, first-time homebuyers, and developers: this is an opportunity not to be missed. Secure a prime detached property in the heart of Brooklin in Whitby set on a rare and expansive 70 ft x 90 ft lot, just off Highway 7 (Winchester Road East). Ideal for renovation, redevelopment, or t Whitby (Brooklin), ON Living Area: Sqft.	2 Beds, 1 Bath	$949,000
LOT 44 JOYCE MARSHALL DRIVE Welcome to this stunning, 32' Detached Columbus Elevation "A" Model offering 1, 923 sq. ft. of beautifully finished spaces. Boasting 3 spacious bedrooms and 3 washrooms. The 9' Main and 2nd Floors feature smooth ceilings. The Elegant hardwood floors on the main complemented by the stained oak veneer Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$949,549
LOT 93 FEDERICA STREET Welcome to this stunning, 32' Detached Corridale Elevation "A" Model offering 2, 410 sq. ft. of beautifully finished spaces and Double Car Garage. Boasting 4 spacious bedrooms and 4 washrooms. The Elegant hardwood floors on the main complemented by the stained oak veneer stairs add warmth and charac Whitby, ON Living Area: Sqft.	4 Beds, 4 Baths	$1,043,990
LOT 89 FEDERICA STREET Welcome to this stunning, 38' detached Colston Elevation "A" model offering 2559 sqft of beautifully finished spaces and double car garage. Boasting 4 spacious washrooms. Smooth Ceilings Throughout. The main floor welcomes you with a spacious family room, perfect for gatherings. The gourmet kitchen Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,153,990
680 WINCHESTER ROAD W Location/Location/Location. At the crossroads of Country Lane and Highway 7, this stunning 11.82 acre farm offers a ready-to-move-in house or the perfect place to build your dream home or Home-based businesses or secondary suites (Buyer to do own due diligence). In Whitby's Calm Countryside, Adjacen Whitby, ON Living Area: Sqft.	4 Beds, 3 Baths	$2,950,000
29 QUEEN STREET Welcome to 29 Queen Street! Rarely offered & seldom found on this demand street in Old Brooklin nestled on a private 96.29 x 88.50 ft mature lot with amazing detached garage, steps to parks, schools, transits & downtown shops. This all brick bungalow has been beautifully updated throughout including Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 2 Baths	$1,119,900
44 STRANDMORE CIRCLE Welcome to this executive 4 bedroom home plus 2 home offices....perfect for those who love to work from home! Set in beautiful Brooklin this home features hardwood floors throughout you'll love the formal and cozy living room perfect to receive your guests. With ample room in the bright and airy din Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 5 Baths	$1,370,000
106 MONTGOMERY AVENUE Executive 4+3 bedroom Tribute 'Imperial' Model with Legal Basement Apartment! Situated on a corner lot with large porch to enjoy the pond & treed views. Inviting entry with hardwood flooring throughout, formal living & dining rooms make this home perfect for entertaining. Gourmet kitchen boasting gr Whitby, ON Living Area: 0 Sqft.	7 Beds, 5 Baths	$1,549,900
142 VIPOND RD Beautiful 4 bedroom family home located in desirable Brooklin on a premium lot featuring great open concept design with soaring 9ft ceilings, hardwood floors on living room, dining and family room, bright eat in kitchen with pantry and breakfast bar, breakfast area with walk-out to patio and family Whitby, ON Living Area: 0 Sqft.	4 Beds, 3 Baths	$1,075,000