Winchester Real Estate for Sale

Rarely offered Kaitlin-built condo apartment in highly sought-after Brooklin! This bright and inviting 1-bedroom, 1-bath suite is the perfect place to start, ideal for professional couples or downsizers. Featuring a sun-filled open-concept layout with spacious living and dining areas, plus a sliding glass walkout to a private balcony with easterly views.The kitchen offers ample cupboard space, backsplash, pantry, ceramic flooring, breakfast bar, and stainless steel appliances. The generous bedroom includes a large window and walk-in closet. Enjoy the convenience of ensuite laundry and an owned locker in Building 54 for extra storage.Minimal condo fees include common area maintenance, plus access to the gym and party room facilities in Building 54. Located steps from downtown Brooklin shops, big box stores, the recreation centre, library, and with easy access to Highways 407 and 418 for commuters. Units like this don't come up often!

This exceptional Brooklin family home combines thoughtful design, upscale finishes, and an incredible backyard retreat. Offering 4 spacious bedrooms and 4 bathrooms, this custom-built home is perfectly suited for both everyday living and entertaining.The beautifully landscaped, maintenance-free backyard is fully fenced and designed for enjoyment, featuring premium artificial turf, a hot tub, a large entertainer's deck, and exterior pot lighting that creates the perfect evening ambiance. Inside, the welcoming foyer opens to a bright and versatile den with direct access to the garage and laundry area. The main living space showcases stylish laminate flooring, pot lights, and expansive windows overlooking the backyard. At the heart of the home is the stunning chef-inspired kitchen complete with quartz countertops, upgraded stainless steel appliances, modern backsplash, oversized center island with breakfast seating, and elegant pendant lighting. The adjoining dining area offers a seamless walk-out to the backyard, making indoor-outdoor entertaining effortless. The upper level features four generously sized bedrooms, including a luxurious primary suite with a walk-in closet and spa-like 4-piece ensuite. A second bedroom also enjoys its own private 5-piece ensuite and walk-in closet - ideal for guests, teens, or extended family.

Welcome to 33 Watford St, a spacious 4+1-bedroom, 3-bathroom executive home in sought-after Brooklin, offering approximately 3,294 sq. ft. above grade, plus a finished basement and a private backyard oasis with an inground pool. Designed for family living and entertaining, the main floor features hardwood flooring, crown moulding, a dedicated office/den with French doors, and a dramatic family room with soaring vaulted ceilings, a gas fireplace, a built-in media centre, and floor-to-ceiling windows that fill the space with natural light. The updated eat-in kitchen offers a centre island, granite and quartz counters, ceramic flooring, and a walkout to the fully fenced backyard, complete with an inground pool with liner replaced in 2023, interlock patio, and plenty of space to relax or entertain. Upstairs, you'll find four generous bedrooms with newer engineered hardwood flooring. The primary suite features a 5-piece ensuite and a walkout to one of two second-floor balconies, creating a rare and inviting outdoor retreat. The finished basement adds excellent flexibility with an additional bedroom, recreation space, and workshop. Additional features include new windows in 2025, a newer wrought iron staircase, a main floor laundry with garage access, a separate side entrance, and a double-car garage. A rare opportunity to own a large Brooklin family home with the space, pool, and lifestyle features buyers are looking for.

Lifted from the pages of a magazine, this spectacular 4-bedroom family home offers nearly 3,000 sq ft of beautifully finished living space and an exceptional main floor designed for both everyday comfort and entertaining. Featuring extensive hand-scraped heritage maple hardwood flooring, a hardwood staircase with wrought iron spindles, pot lighting, and elegant california shutters, this home is loaded with high-end upgrades.The gourmet kitchen is a showstopper, complete with quartz countertops, custom subway tile backsplash, stainless steel appliances including a gas range, apron sink, and a large centre island with breakfast bar & accented by stylish pendant lighting. A garden door walkout leads to the private backyard oasis, professionally landscaped with interlock patio (2021), relaxing hot tub, lush gardens, natural gas BBQ hookup, and access to the gas-heated double detached garage.The main floor also offers formal living and dining rooms with coffered ceiling, a cozy family room with upgraded gas fireplace with custom mantle (2026) and backyard views, a convenient home office, and a sunken laundry room. Upstairs, find four generously sized bedrooms including a luxurious primary retreat with a spa-inspired 5-piece ensuite featuring a custom granite double vanity, glass rain shower, heated floors, feature wall, and a stand-alone soaker tub with fireplace views. Dual walk-in closets include custom organizers. Additional updates include windows (2019), two-stage furnace (2020), upgraded attic insulation, and a 30-year roof (2010). The unspoiled basement offers above-grade windows, fully framed, insulated, roughed in plumbing for wet bar/bath and hookup for gas fireplace. Pride of ownership is evident throughout this exceptional home! Steps to sought after schools, parks, downtown Brooklin shops & easy hwy 407 access for commuters!

Welcome to this beautifully updated family home in the heart of Brooklin, perfectly situated on a private 145-ft deep lot with no neighbours behind. Offering stylish renovations, functional living space, and an incredible backyard retreat, this home is ideal for growing families and those who love to entertain. Step inside to an inviting open-concept main floor featuring gleaming hardwood floors, extensive pot lighting, crown moulding, and tasteful finishes throughout. The spacious family room is highlighted by a cozy double-sided fireplace, creating a warm and welcoming atmosphere. A formal dining room provides the perfect space for hosting family gatherings and special occasions. The eat-in kitchen is designed for both everyday living and entertaining, featuring quartz countertops, a stylish backsplash, ceramic flooring, ample cabinetry, and generous prep space. The bright breakfast area offers a walkout to the backyard oasis complete with an interlocking patio, refreshing pool, and plenty of green space to relax, play, and enjoy the privacy of having no rear neighbours. Convenient main-floor laundry with direct garage access adds to the home's functionality. Upstairs, you'll find three generously sized bedrooms, all with excellent closet space. The primary suite serves as a private retreat, featuring a walk-in closet and a spa-inspired 4-piece ensuite with a standalone soaker tub and glass shower accented by custom herringbone tile. The fully finished basement extends the living space with a large recreation room, play area, oversized windows, and abundant storage, offering endless possibilities for family enjoyment. Located in a family-friendly neighbourhood, this exceptional home is just steps to parks, schools, walking trails, community amenities, and the charming shops and restaurants of downtown Brooklin. Commuters will appreciate the convenient access to Hwy 407. Move in and enjoy the perfect combination of comfort, style, privacy, and location.

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 the creation of a custom dream home, this property offers outstanding potential in one of Whitby's most desirable communities. Enjoy the convenience of walking to shops, parks, and top-rated schools, the lifestyle you've been waiting for is right at your doorstep. An exceptional chance to build, invest, or grow in a highly sought-after neighborhood.

The first thing you'll notice is the impressive 9-foot ceilings, creating a bright, open feel throughout the main level. Set within a quiet, family-friendly neighbourhood, this beautifully maintained 4-bedroom, 4-bath home offers the perfect blend of comfort, space, and convenience. Featuring quality stainless steel appliances, spacious principal rooms, and a functional layout designed for modern living, this home is ideal for growing families and those who love to entertain.Step outside to a private, fully-fenced backyard-perfect for kids, pets, or relaxing summer evenings. Whether you're hosting or unwinding, the outdoor space offers both privacy and versatility.Located just minutes to Highway 407, commuting is seamless while still enjoying the peace of a well-established community. Public transit is also conveniently close, adding to the home's accessibility.Families will appreciate access to excellent schools including Winchester PS and Brooklin HS. Enjoy nearby parks, trails, and a wide range of recreational amenities, all within walking distance-perfect for an active lifestyle.With shopping, dining, and essential services just minutes away, this home delivers the complete package.A rare opportunity to own a home that truly checks all the boxes-location, lifestyle, and long-term value.

Beautifully maintained and freshly painted detached family home in the heart of highly desirable Brooklin! This spacious 4-bedroom home with a versatile multipurpose den and 5 bathrooms offers the perfect blend of luxury, comfort, and functionality. The open-concept main floor features 9-ft ceilings, an elegant separate dining area and a bright oversized family room highlighted by a stunning 3-sided gas fireplace. The modern kitchen showcases sleek finishes, a breakfast bar, and a walk-out to your private backyard oasis featuring a luxurious spa-inspired infinity swimming pool - perfect for relaxing or entertaining family and friends.The fully fenced backyard and expansive deck create an exceptional outdoor living experience. Convenient laundry with direct garage access, and thoughtfully designed living spaces throughout.This smart home is fully integrated with Google Home voice commands and includes a ceiling-mounted audio system in the living and dining rooms, along with low-level ambient lighting designed to create a relaxing evening atmosphere. All speakers and lighting systems are included, along with setup instructions for the new owners to easily connect to their internet service.The finished basement provides additional living space with 2 bedrooms and a 3-piece bathroom, ideal for extended family, guests, or a potential in-law suite. Located in a highly sought-after family-friendly neighbourhood, this home is within walking distance to top-rated schools, parks, shops, restaurants, and all amenities, with convenient access to Hwy 407 for commuters.A rare opportunity to own a stylish, spacious, and fully upgraded home in one of Brooklin's most desirable communities!

Client RemarksWelcome to 52 Wessex Dr in sought-after Brooklin. Spacious 4+1 bedroom home offering a functional layout and great potential. Features include a large primary suite with walk-in closet and 4-piece ensuite, an eat-in kitchen with a breakfast bar and walkout to the backyard, and an open-concept family room with fireplace. Combined living and dining areas provide additional space for entertaining- hardwood flooring throughout main and second levels. Finished basement with second kitchen, bedroom, and 3-piece bath offers flexibility for extended family or future use. Excellent opportunity to enter the Brooklin market and add value.Close to top-rated schools, parks, shopping, Hwy 407, and all amenities.

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 today's most sought-after design trends throughout.Situated on an impressive 68 x 166 ft lot with a grand circular driveway, this home offers unforgettable curb appeal and a bright open-concept layout filled with natural light. Inside, you'll find oversized principal rooms, smooth ceilings, custom millwork, upscale lighting, and carefully curated finishes that perfectly balance character and contemporary style.The stunning custom kitchen is designed for both everyday living and effortless entertaining. The sun-filled living and dining area, framed by a charming bay window, creates a warm and inviting atmosphere. A stylish barn door leads to the versatile main floor bedroom retreat complete with its own updated 3-piece bath - ideal as a guest suite, private primary bedroom, or multi-generational living space.The cozy family room features a gorgeous gas fireplace and oversized windows overlooking the private fenced backyard. Step outside to enjoy the incredible 300 sq ft four-season cabin with loft space - perfect as a home office, studio, gym, or guest retreat.Upstairs, the luxurious primary suite offers a walk-in closet and spa-inspired 5-piece ensuite. A dedicated dual home office near the side entrance and garage adds even more flexibility for today's lifestyle.Located steps to downtown Brooklin shops, restaurants, parks, and schools, this exceptional turnkey property offers a rare opportunity to own a beautifully restored piece of Brooklin history.

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 countertops, a breakfast bar, and flows seamlessly into the dining area with a walkout to a spacious deck overlooking the private backyard oasis. With two main-floor kitchens, a wet bar in the basement, and two in-law suite potentials, this home is ideal for " Multigenerational" living whether its parents, in-laws, or adult children, everyone can enjoy their own space while still being under one roof. Additional highlights include a newly updated 5pc semi-ensuite (2023), laminate flooring throughout, a large 227 deep lot with an above-ground pool, hydro-equipped garden shed, and hot tub hookup. The inviting living room with French doors and wood-burning fireplace adds warmth and charm, while the converted garage offers flexible living space that can easily be reverted if desired. Outside, the abundant and private backyard is perfect for entertaining or quiet relaxation. All this, just minutes from downtown Whitby, golf courses, conservation areas, restaurants, shopping, and with GO/Transit right at your doorstep!

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 gleaming hardwood floors, including stairs with wrought iron spindles. The open-concept design continues into the updated (2024) kitchen, featuring a stylish custom backsplash, abundant counter and cabinet space, ceramic floors, and a generous breakfast area with walk-out to the fully fenced backyard-complete with lush gardens and a handy storage shed.The fully finished basement provides plenty of room to grow, showcasing large above-grade windows, pot lighting, a cozy gas fireplace, a 2-pc bath, games room with recently re-covered pool table, playroom, office with French doors, and ample storage space.Upstairs, the spacious primary retreat offers a spa-like 4-pc ensuite with soaker tub and his-and-hers closets. The updated main bath includes heated floors for added comfort. Pride of ownership is evident throughout! Ideally located steps from top-rated schools, parks, downtown Brooklin shops, and offering quick 407/412 access for easy commuting!

Great Investment Opportunity!!Legal All-Brick Duplex in Prime Brooklin Location. Well-maintained, purpose-built duplex offering two self-contained units with excellent layout and privacy. Main floor unit features open-concept kitchen with island, combined living and eating area, bedroom with ensuite, additional powder room, and two second-floor bedrooms with full bath. Includes exclusive use of1-car garage. Lower unit with discreet side entrance, open concept living w/ two bedrooms, full bathroom plus powder room, and private in-suite laundry. Private Driveway accommodates 3 to 4 vehicles. Separate entrances and separately metered. Desirable Downtown Brooklin neighbourhood close to schools, amenities, and transit. Tenants to be Assumed. Not subject to rent control.

Welcome To This Beautifully Maintained, Move-In Ready Home In Sought-After Brooklin, Nestled On A Quiet Crescent. Offering 2,882 Sq. Ft. (As Per MPAC) Plus A Finished Basement With Wet Bar, Media Area & Games Space - Perfect For Entertaining.Functional Main Floor Layout Featuring Spacious Living & Dining Areas, Hardwood Floors Throughout And A Cozy 3-Sided Gas Fireplace. Family Room With A Bay Window Offering Abundant Natural Light. Kitchen With Granite Counters, Custom Cabinetry, Breakfast Bar & Wine Rack.Oak Staircase Leads To The Second Floor Featuring Four Generous Bedrooms, Including Two With Ensuites. Large Primary Bedroom With 5-Pc Ensuite & His/Hers Walk-In Closets. Second Floor Office Provides An Ideal Work-From-Home Space.Enjoy A Custom Composite Deck With Beautiful Summer Blooms And Outdoor Space Perfect For Entertaining. Rough-In Bath In Basement.Updates: Roof (2019), Front Yard Interlock (2022), Furnace (2025), A/C (2024), Second Floor Flooring (2025), Upgraded Bathrooms & Paint (2026), Attic Insulation (2024).All Of This Within Walking Distance To Top-Rated Schools & Moments From Downtown Brooklin, Golf Courses, The 407, Shops, Dining & More.

Beautiful bungalow offering excellent potential for first-time home buyers, investors, or those looking for multi-generational living. The main floor features 2 spacious bedrooms, a bright and functional layout, and comfortable living space throughout. The separate entrance basement includes 1 bedroom, a living room, and a 3-piece bathroom, providing great in-law suite or convert into rental potential. Live in one space and rent the other to help offset your mortgage, or add this property to your investment portfolio and hold for future growth and development potential. A fantastic opportunity in a growing and desirable area of Brooklin.

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.The main home features 4 bedrooms and 2 bathrooms, while the bungalow, added in 1999, is handicap accessible and ideal for in-laws or extended family.The large lot provides plenty of outdoor space - even room for a pool! Live together, but with your own space - or rent out one side for extra income. Truly, two homes for the price of one! This home must be viewed in person to fully appreciate

Corner Detached Property located on Simcoe Street & Winchester. Home is located across the street from Luther Vipond Brooklin Memorial Arena and Brooklin Memorial Park. Potential Development Opportunity. Property is zoned Medium density residential within Brooklin's Secondary plan. Buyers to Verify zoning and development potential with City & Region. Must be purchased together with 88 Winchester Road E. Both Properties combined is approximately 1/2 an acre. Pictures of lot is including neighboring lot.

Detached 3 Bedroom 1 Bath Property located on beautiful lot on Winchester Road E. Home is located across the street from Luther Vipond Brooklin Memorial Arena and Brooklin Memorial Park. You can make this place your new homeor Purchase together with 86 Winchester for Potential Development Opportunity. Property is zoned Medium density residential within Brooklin's Secondary plan. Buyers to Verify zoning and development potential with City & Region. Both Properties combined is approximately 1/2 an acre

Some lots just make sense. This one makes a statement. Measuring 82 x 145 feet and flanked by custom-built homes on one of Brooklin's most sought-after streets, this is the kind of property serious buyers quietly wait for. Builder can provide a custom built home or do your own thing. A mature, established neighbourhood. A generous, fully fenced lot. And a location that checks every box before you've even drawn up plans. The existing bungalow - 1,107 sq. ft., 3 bedrooms, 1 bathroom, metal roof, detached garage - is a solid starting point for a thoughtful renovation, or simply a placeholder while you design something extraordinary from the ground up. Either way, the lot does the heavy lifting. Top-rated schools, parks, dining, and seamless access to Highways 407 and 412 put everything within easy reach - without sacrificing the quiet, community feel that makes Brooklin such a compelling place to plant roots. Lots of this calibre, on streets of this reputation, don't surface often. When they do, they don't wait.

Welcome to 5 Iberville! A rare find in the highly desirable Brooklin neighbourhood. Meticulously maintained by the original owners, this all-brick, two-storey detached home showcases true pride of ownership and thoughtful upgrades throughout. Tucked away in a quiet family pocket, this 4-bedroom home features a private, fully-fenced backyard oasis with a heated inground pool for your own personal escape. The heart of the home is a bright and functional eat-in kitchen, fully upgraded with select cabinetry, quartz countertops, a stylish backsplash, and quality stainless steel appliances. The breakfast area, illuminated by a designer light fixture, features sliding doors that lead directly to the patio. For cozy evenings, the large family room boasts an electric fireplace, while the combined living and dining rooms offer a bright, versatile space for formal entertaining. Fully upgraded bathrooms, boasting durable quartz counters, ceramic tile, and glass-door showers.The second floor features a convenient laundry room and four spacious bedrooms. The primary retreat offers wall-to-wall closets with a 4-piece ensuite. The three additional bedrooms are bright and comfortable, each featuring upgraded windows and closets. The backyard is truly one-of-a-kind, featuring a heated inground pool surrounded by landscaped garden beds, a built-in fire pit enclosure, and a gazebo. For those looking to expand, the basement remains a blank canvas, perfect for a home office or recreation room, with ample storage under the stairs.Perfectly situated in a family-friendly community close to schools, parks, amenities, and walking trails. Commuting is a breeze with quick access to Hwy 407 and 412.

Welcome to this stunning 3+1 bedroom end-unit townhouse, perfectly situated in one of WHitby's most desirable communities. This bright and spacious home offers an abundance of natural light thanks to its large windows and end-unit layout, creating a warm and inviting atmosphere throughout. The main level features an open concept living and dining area, ideal for entertaining or enjoying cozy family nights. Upstairs, you'll find three generously sized bedrooms, including a serene primary retreat. The fully finished basement adds incredible versatility with a room that can be used as a bedroom, home office, gym, or media room tailored to suit your lifestyle. Enjoy the convenience of being just minutes away from top rated schools, grocery stores, parks, shops, and all essential amenities, Whether you're a growing family, a first time buyer, or someone looking to downsize without compromise, this property checks all the boxes.

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, Adjacent To Hwy 412, 407. Whitby's Brooklin neighborhood is five minutes away. This charming home offers a blend of historical elegance, modern comfort and featuring ceilings that are about 9 feet high. Enjoy The Luxurious 5-Piece Bathroom With A Deep Soak Tub And Generous Shower Upstairs. Add appeal to the home with a hardwood floor. Enjoy the tranquil surroundings by stepping outside onto the spacious second-floor terrace. Custom maple cabinets, premium stainless steel appliances, and sophisticated granite countertops make the kitchen a chef's dream come true. Enjoy The Coziness Of The Kitchen's And Bathroom's Heated Flooring. This property is truly a slice of paradise, offering excellent potential for future development and being close to all amenities.

Stunning Queensgate Home In The Most Desired Area, G/F 9' Ceilings, Over 2000 Sqft, Great Layout, Open Concept, Lots Of Windows, Bright & Spacious, Family Room Gas Fireplace, Master Br C/W W/I Closet, Stand-Up Shower & Soaker Tub, Large Laundry Room Has Door To Double Garage, Close To Transits, Malls, Schools, Parks, Golf Courses, Nature Trails, Etc.

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 vanities include quartz countertops from the builder's premium selections, along with stylish trim and thoughtful details. Enjoy the convenience of main-floor laundry and a functional layout ideal for everyday living and entertaining. The finished basement adds valuable extra living space, complete with a large recreation area perfect for family gatherings, a home office, gym, or guest space. Located in an established neighbourhood close to schools, transit, amenities, and Hwy 407. Includes premium upgrade packages throughout. Quality. Comfort. Delta-Rae Craftsmanship.

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 center island, pot drawers, a stylish backsplash, and under-cabinet lighting. The primary bedroom includes a 4-piece ensuite and walk-in closet, plus a spacious second bedroom. Enjoy the convenience of main-floor laundry and a basement with large windows, a finished landing, higher ceilings, and 200-amp service. The garage is fully drywalled for a polished finish. Located steps from top schools, parks, and amenities, with quick access to public transit and highways 407, 412, and 401. Kindly note certain rooms have been virtually staged to show scale of rooms and provide inspiration. We have provided exact photos of each room as they are before each staged photo. The options with these homes in terms of furniture placement and design are absolutely endless!

Spacious 1,900 sq ft beautifully finished home with 3 Bdrms, 4 Baths, sun-filled open concept floor plan. Eat-in Kitchen with Island and Breakfast Bar, with Two Walkouts to a Large Deck Perfect for Outdoor Entertaining. Balcony off the Master Bdrm provides additional outdoor living space. Other highlights of this home include a private driveway, a built-in garage, and ample parking and storage options. Located near parks, shopping, downtown Brooklin, schools and easy highway access for commuters and much, much more! Must Be Seen, Book a Showing Now!!! VTB 1st or 2nd mtg. Min. 15% Dp. regardless of income or credit!!