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 52 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 52 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
20 DENBURY COURT Welcome to one of Brooklin's most exclusive family enclaves - prestigious Denbury Court. Rarely do homes become available on one of the few true courts in the community, especially one that offers this level of luxury, space, and modern updates. Designed for growing families who refuse to compromise Whitby (Brooklin), ON Living Area: Sqft.	6 Beds, 5 Baths	$1,349,000
7 WOODINGTON COURT Rarely offered in the prestigious Chateaus of Woodington, this exceptional custom-built "Royale" model is perfectly positioned on one of the area's most sought-after family-friendly courts, just steps from protected treed space and walking paths for an unmatched sense of privacy and tranquility. Set Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 5 Baths	$2,450,000
274 MONTGOMERY AVENUE Welcome to this exceptional Turnberry model offering over 2, 800 sq. ft. of beautifully upgraded living space in one of Brooklin's most sought-after family-friendly neighborhoods. Situated onan extended premium lot in Northwest Brooklin, this impressive 4-bedroom, 4-bathroom home combines style, com Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,189,900
61 VANGUARD DRIVE Welcome to 61 Vanguard Drive in one of Whitby's most desirable family-friendly communities. This beautifully updated 4-bedroom, 3-bathroom home offers the perfect blend of modern finishes, functional living space, and impressive curb appeal. Step inside to discover a completely renovated interior fe Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 3 Baths	$799,999
25 MONTANA CRESCENT Welcome to this exceptional Tribute Homes "Somerset Platinum Edition" executive bungalow on a premium 175-ft deep lot with a resort-style backyard oasis! Offering 3+1 bedrooms, 4 bathrooms, and a triple-car garage, this all-brick home combines luxury, comfort, and functionality. Impressive curb appe Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,998,888
33 NORTH STREET Welcome To 6, 000+ Sq Ft Of Elegantly Finished Living Space. On A Premium 97 x 150ft Lot In One Of Brooklin's Most Sought-After Pockets. Custom Built By "Delta-Rae" In July 2020, This 4+2 Bedroom, 5 Bath Home Has Been Enhanced With Nearly Half A Million Dollars In Post-Build Upgrades - Every Dollar Whitby (Brooklin), ON Living Area: Sqft.	6 Beds, 5 Baths	$2,679,900
74 DARIUS HARNS DRIVE ~ Stunning All-Brick Detached 4-Bedroom Family Home In The Highly Sought-After Brooklin Community Featuring An Incredible Resort-Style Backyard Oasis With Inground Pool, And Beautifully Landscaped Privacy Setting - Perfect For Entertaining All Summer Long.~ This Spacious Home Offers Exceptional Curb Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,299,000
15 JORDAN COURT Step into a lifestyle of effortless luxury and poolside relaxation in this impeccably maintained 4-bedroom family home, situated on a premium 55' x 121' lot on a coveted court in the highly sought-after community of Brooklin. Perfectly positioned just steps from parks, top-rated schools, trails, cha Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 5 Baths	$1,499,000
93 HOLSTED ROAD Welcome to this beautifully reimagined home offering over 3, 000 sq ft of thoughtfully updated living space. This property has undergone extensive renovations, delivering a modern, turnkey experience from top to bottom. Featuring 4 spacious bedrooms and 4.5 fully updated bathrooms, including a newly Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 5 Baths	$1,349,000
41 LEITHRIDGE CRESCENT This is the one people drive by and wonder about. Now you can live in it.This gorgeous 2+2 bedroom bungalow in the heart of Brooklin is designed to impress - and it delivers at every turn. A private backyard oasis with inground saltwater pool, an open concept main floor with soaring vaulted ceilings Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 3 Baths	$1,299,000
77 JOSHUA BOULEVARD Step into a home that truly impresses - where soaring cathedral ceilings, expansive principal rooms, and abundant natural light create an immediate sense of scale, elegance, and warmth. This beautifully upgraded 4+1 bedroom, 5 bathroom residence offers over 3, 500 sq ft of refined living space, desi Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 5 Baths	$1,399,900
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, cafs, and restaurant Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 2 Baths	$1,274,900
83 CASSELS ROAD E Welcome to this stunning, fully reimagined century home in the heart of downtown Brooklin, where historic charm meets modern luxury. With over $250, 000 invested in premium renovations over the last year, this one-of-a-kind 3-bedroom home showcases exceptional craftsmanship, designer finishes, and t Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 2 Baths	$1,299,000
5090 BALDWIN STREET S Welcome to this one-of-a-kind custom home, perfectly set on a large, mature treed lot in a sought-after Whitby location. Offering 3+1 bedrooms, 3 bathrooms, and a fully finished basement, this property blends style, comfort, and versatility. The beautifully renovated kitchen (2023) features quartz c Whitby (Taunton North), ON Living Area: Sqft.	4 Beds, 3 Baths	$929,000
LOT 73L BRADY STREET Welcome to this stunning, 30' Single Model offering 1, 856 sq. ft. of beautifully finished spaces. Boasting 3 spacious bedrooms and 3 washrooms. This home is designed with comfort and style in mind. The main floor welcomes you with a spacious family room, gleaming hardwood flooring, perfect for gath Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 3 Baths	$876,982
LOT 84R MICHAEL KLEIN STREET Welcome to this stunning, Semi-Detached Model offering 1, 658 sq. ft. of beautifully finished spaces. Boasting 3 spacious bedrooms and 3 washrooms. This home is designed with comfort and style in mind.The main floor welcomes you with a spacious Great Room with Gleaming Hardwood Flooring and walkout Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 3 Baths	$791,142
16 CODY AVENUE Welcome to this 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 Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 3 Baths	$1,049,900
45 HATCH STREET E Welcome to 45 Hatch Street, an elegant and thoughtfully designed home nestled in one of Whitby's most prestigious and family-friendly neighbourhoods. Set within the heart of Durham Region, this residence offers the perfect blend of luxurious comfort, natural beauty, and seamless urban connectivity i Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 3 Baths	$899,900
20 DENBURY COURT Welcome to one of Brooklin's most exclusive family enclaves - prestigious Denbury Court. Rarely do homes become available on one of the few true courts in the community, especially one that offers this level of luxury, space, and modern updates. Designed for growing families who refuse to compromise Whitby (Brooklin), ON Living Area: Sqft.	6 Beds, 5 Baths	$1,399,999
LOT 82R MICHAEL KLEIN STREET Welcome to this stunning, Semi-Detached, Myles Elevation "A" Model offering 1, 658 sq. ft. of beautifully finished spaces. Boasting 3 spacious bedrooms and 3 washrooms. The Elegant hardwood floors on the main complemented by the stained oak veneer stairs add warmth and character leading to 2nd Floor Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 3 Baths	$764,593
LOT 75L BRADY STREET Welcome to this stunning, 30' Single, Bond Elevation "A" Model offering 1, 856 sq. ft. of beautifully finished spaces. Boasting 3 spacious bedrooms and 3 washrooms. This home is designed with comfort and style in mind.The 9' Main and 2nd Floors feature smooth ceilings. The Elegant hardwood floors on Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 3 Baths	$859,283
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
93 HOLSTED ROAD Welcome to this beautifully reimagined home offering over 3, 000 sq ft of thoughtfully updated living space. This property has undergone extensive renovations, delivering a modern, turnkey experience from top to bottom. Featuring 4 spacious bedrooms and 4.5 fully updated bathrooms, including a newly Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 5 Baths	$1,425,000
77 JOSHUA BOULEVARD Space, style, and a stunning renovation in fabulous Brooklin. This is the home you've been waiting for! Offering over 3, 500 sq ft of beautifully upgraded living space plus a fully finished basement, this stunning 4+1 bedroom, 5 bathroom home was extensively renovated in 2023 with wide plank hardwoo Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 5 Baths	$1,449,900
11 DURHAM STREET Perfect for Large or Multigenerational Families! This unique property offers two homes in one - a spacious One and a half-storey house plus a bungalow addition, each with its own entrance, kitchen, and living areas. Both spaces are fully self-sufficient, yet connected for easy access between the two Whitby (Brooklin), ON Living Area: Sqft.	6 Beds, 4 Baths	$1,149,000
14 NAPIER COURT Nestled on a quiet cul-de-sac, this beautiful and recently updated home is in a community friendly neighbourhood and backing to green space. This well maintained all brick spacious bungaloft is just minutes from the 407, schools, parks, shopping & all activities/amenities that vibrant Brooklin has t Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 2 Baths	$919,900
33 NORTH STREET Refined Elegance Defined By Curated Craftsmanship Encompassing Over 5000 Square Feet Finished On 95' Footage Corner Lot In Brooklin's Most Desirable Enclave - 4 Plus 2 Bed, 5 Bath Fully Custom Masterpiece Completed By Renowned "Delta-Rae" In 2020 Features Wide Plank Hardwood, Main Floor Office, Gour Whitby (Brooklin), ON Living Area: Sqft.	6 Beds, 5 Baths	$2,976,000
37 DUGGAN AVENUE Experience a warm, inviting ambiance the moment you step through the front door of this beautiful Brooklin home. Picture your family gathered in the spacious family room, where hardwood floors and a cozy gas fireplace create the perfect setting for quiet evenings or lively conversations. A beautiful Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 3 Baths	$925,000
140 VIPOND ROAD Welcome to this beautifully upgraded Melody-built 4-bedroom family home with backyard oasis and inground pool! The extensively landscaped exterior features large covered porch overlooking the front gardens, backyard with stamped concrete patio, lush gardens, mature trees for privacy, and gated acces Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,119,900
9 ELDER CRESCENT Welcome to this stunning 'Coronation' model in the heart of Brooklin! This beautifully upgraded 4+1 bedroom home checks every box , thoughtfully designed for growing families and effortless entertaining alike. From the moment you step inside, the quality is undeniable. A custom staircase with design Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 4 Baths	$1,274,900
33 NORTH STREET Refined Elegance Defined By Curated Craftsmanship Encompassing Over 5000 Square Feet Finished On 95' Footage Corner Lot In Brooklin's Most Desirable Enclave - 4 Plus 2 Bed, 5 Bath Fully Custom Masterpiece Completed By Renowned "Delta-Rae" In 2020 Features Wide Plank Hardwood, Main Floor Office, Gour Whitby (Brooklin), ON Living Area: Sqft.	6 Beds, 5 Baths	$3,280,000
21 CORVINELLI DRIVE WOW! STYLISH AND METICULOUS, THREE+1 BEDROOM BUNGALOW * CAR LOVERS DREAM THREE CAR GARAGE * FULLY FINISHED BASEMENT WITH SEPARATE ENTRACE TO GARAGE * EXTRA DEEP FULLY LANDSCAPED LOT WITH POOL * AND WALKING DISTANCE TO EVERYTHING BROOKLIN HAS TO OFFER! This exceptional property offers an unparalleled Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,649,900
114 STRANDMORE CIRCLE Welcome to the Ashbury model, a rare layout on a quiet circle in sought after Brooklin, where kids still play outside. This all-brick home offers over 2, 500 sq ft of thoughtfully designed living space. A double-door entry opens to a spacious foyer, flowing into an expansive main floor with an open- Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 3 Baths	$1,095,000
139 TREMOUNT STREET Tucked away on a premium ravine lot in one of Brooklin's most sought-after pockets, this all-brick 4+1 bedroom home offers the kind of privacy and setting that rarely comes to market. Imagine no rear neighbors-just mature trees, quiet mornings on the deck, and a backyard that feels like your own pri Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 4 Baths	$949,000
93 COLSTON AVENUE Welcome to one of Brooklin's most impressive addresses! This home stands as a masterclass in executive luxury, offering over 4, 000 square feet of meticulously curated living space designed for the most discerning homeowner. From the moment you walk in, the 10-foot ceilings and custom mouldings crea Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 5 Baths	$2,249,000
5 CENTRE STREET W Stunning custom-built executive bungalow offering 2+2 bedrooms, 4 bathrooms, 4250 sq ft of luxury living space and a beautifully finished in-law suite! This open-concept home features premium upgrades throughout, including extensive hardwood flooring, hardwood staircase with wrought iron spindles, p Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 4 Baths	$1,849,900
55 GARSIDE AVENUE Highly sought after Meadowcrest neighbourhood in Old Brooklin! Excellent location! Walking distance to charming downtown Brooklin shops, restaurants, schools, parks, transit, library & with exceptional community centre & super quick access to hwy 407! First time offered in almost 40 years! Very char Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 2 Baths	$849,800
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	$3,250,000
35 BELLHOUSE PLACE Stunning Tribute built "Roxton" model situated on a premium 46 ft frontage in one of Brooklin's most desirable family neighborhood's. This beautifully upgraded home offers a bright open-concept layout with 9 ft ceilings and hardwood flooring throughout the main level. The oversized kitchen features Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 4 Baths	$1,174,900
51 NATHAN AVENUE Located in one of Brooklin's most sought-after family neighbourhoods, this impressive brick and stone bungalow offers over 2, 057 sq ft above grade plus a beautifully finished basement with a 2nd kitchen and a separate entrance designed for flexibility and comfort. Set on a large landscaped corner l Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 4 Baths	$1,449,000
67 AULT CRESCENT Welcome to 67 Ault Crescent. Nestled in the highly desirable community of Brooklin, this charming 3 bedroom + 2 bath home combines small-town charm with modern conveniences. With access to top rated schools, parks, shopping, restaurants, amenities and Highway 407, this is an exceptional opportunity Whitby (Brooklin), ON Living Area: Sqft.	3 Beds, 2 Baths	$829,000
57 KIMBERLY DRIVE This Beautiful Bungalow in Brooklin is Over 3300 sq.ft. of Finished Living Space on a Oversized 60 X 115 ft Lot. Recently Renovated Kitchen with New Quartz Counters, Backsplash and Stainless Sink & Faucet. Open Concept Kitchen, Breakfast and Family Rooms. Gorgeous Oak Hardwood Floors in the Living R Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 3 Baths	$998,900
33 NORTH STREET Refined Elegance Defined By Curated Craftsmanship Encompassing Over 5000 Square Feet Finished On 95' Footage Corner Lot In Brooklin's Most Desirable Enclave - 4 Plus 2 Bed, 5 Bath Fully Custom Masterpiece Completed By Renowned "Delta-Rae" In 2020 Features Wide Plank Hardwood, Main Floor Office, Gour Whitby (Brooklin), ON Living Area: Sqft.	6 Beds, 5 Baths	$3,280,000
55 GARSIDE AVENUE Highly sought after Meadowcrest neighbourhood in Old Brooklin! Steps to the downtown shops & restaurants, schools, parks, transit, library, rec centre & hwy 407! First time offered in almost 40 years! Very charming, sparkling clean, 3+2 bedroom, 1040 sq ft, 2 bath, brick bungalow with huge double wi Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 2 Baths	$859,900
1 CENTRE STREET W Custom built 4+1 bedroom family home with a separate legal basement apartment offers outstanding quality, design, and versatility. Built with 2x6 construction, foam insulation in all walls and attic, and upgraded soundproof windows, no detail has been overlooked. The main level features 9-ft ceiling Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 5 Baths	$1,399,000
59 QUEEN STREET Custom-built Corvinelli bungalow featuring over 4400+ sqft of finished living space blending comfort, thoughtful design and unmatched quality.Nestled on a generous lot with mature trees this home offers a private retreat with modern luxuries. Exquisite craftsmanship is evident with high-quality upgr Whitby (Brooklin), ON Living Area: Sqft.	5 Beds, 4 Baths	$2,045,000
82 VIPOND ROAD Welcome to 82 Vipond Road, a beautifully maintained family home in the heart of Brooklin where thoughtful updates meet everyday comfort. Recent 2026 renovations bring a fresh, modern feel throughout, including newly refreshed and professionally painted kitchen cabinetry, a full interior repaint, ref Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 3 Baths	$1,069,000
16 CODY AVENUE Welcome to this stunning 3+1 bedroom Meadowcrest Model by Melody Homes! This all-brick family home offers a bright and inviting foyer with soaring 11-ft ceilings leading to the sun-filled formal living and dining rooms, both finished with gleaming hardwood floors including stairs with wrought iron s Whitby (Brooklin), ON Living Area: Sqft.	4 Beds, 3 Baths	$1,129,900
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
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