Chris Pennycook

Office 204-989-5000 | chrispennycook@royallepage.ca

My Listings

1-12/463

  • 100 Waterloo Street in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202617156

    100 Waterloo Street River Heights North Winnipeg R3N 0S2
    Main Photo: 100 Waterloo Street in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202617156

    100 Waterloo Street Winnipeg R3N 0S2 River Heights North

    $1,595,000
    Residential
    Status:
    Active
    MLS® Num:
    202617156
    Bedrooms:
    5
    Bathrooms:
    4
    Floor Area:
    3,381 sq. ft.
    S/S Thur. Aug.6, offers Tues. Aug.11 after 6 pm. Loaded with character & timeless charm, this beautifully maintained North River Heights home is located steps from Wellington Crescent on a picturesque, tree-lined street. Rich wood trim, original doors, wainscoting, hardwood flrs, crown moulding, arched alcoves, French doors preserve its classic appeal. The formal LR & DR are perfect for entertaining, while the stunning DLUX island eat-in kitchen offers granite countertops, high-end ss appliances, gas cooktop, prep sink, soft-close cabinetry & abundant storage. Garden doors lead to the deck & beautifully landscaped, park-like backyard, while the spacious 3-season sunroom provides the perfect place to unwind. A main floor den overlooks the tree lined street. Upstairs offers a/c, 4 bedrooms & 3 baths, including a bright primary suite w/Juliette balcony, custom WICC & ensuite w/soaker tub & o/s walk-in shower. The partially finished bsmt features a tavern-inspired rec room w/rich wood finishes, built-ins, dry bar & wood-burning fireplace. Shingles approx. 5 years old, AT/2 & exceptional curb appeal with front drive complete this truly special home where original character meets thoughtful modern updates. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 46 Stan Bailie Drive in Winnipeg: South Pointe Residential for sale (1R) : MLS®# 202618856

    46 Stan Bailie Drive South Pointe Winnipeg R3Y 0L4
    Main Photo: 46 Stan Bailie Drive in Winnipeg: South Pointe Residential for sale (1R) : MLS®# 202618856

    46 Stan Bailie Drive Winnipeg R3Y 0L4 South Pointe

    $999,900
    Residential
    Status:
    Active
    MLS® Num:
    202618856
    Bedrooms:
    5
    Bathrooms:
    3
    Floor Area:
    1,978 sq. ft.
    S/S Thurs. Aug. 6, offers Tues. Aug. 11 after 6 pm. Exceptional lakefront family home in desirable South Pointe! This beautifully designed home features stunning lake views, gleaming hardwoods, high ceilings, expansive windows & custom silhouette blinds. The open-concept GR showcases a two-sided gas fp & custom floating media cabinet. The bright dining area flows into a dream kitchen offering soft-close cabinetry, quartz counters, ss appliances, walk-in pantry, island & peninsula w/abundant prep & entertainment space. Garden doors lead to a deck w/glass railing overlooking the lake & backyard. The main level offers 3 generous bedrooms, including a primary suite w/WICC & 4-piece ensuite featuring 2 sinks & o/s walk-in shower. 2nd 4-piece bath & laundry add convenience. The fully finished LL is perfect for entertaining w/a spacious rec room/games area & plenty of room for a pool table. Napoleon fireplace & wet bar fully equipped w/dishwasher & full-size fridge. 2 additional brs w/WICC, 3-piece bath & excellent storage/flex options. Built in 2013 w/HEF, HRV, sump pump & 2 electrical panels. Landscaped, fenced backyard w/covered patio, mature trees & AT/2. Close to walking paths, shopping & all amenities. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 30 Wingate Court in Winnipeg: Linden Woods Residential for sale (1M) : MLS®# 202618854

    30 Wingate Court Linden Woods Winnipeg R3P 2L5
    Main Photo: 30 Wingate Court in Winnipeg: Linden Woods Residential for sale (1M) : MLS®# 202618854

    30 Wingate Court Winnipeg R3P 2L5 Linden Woods

    $779,900
    Residential
    Status:
    Active
    MLS® Num:
    202618854
    Bedrooms:
    4
    Bathrooms:
    3
    Floor Area:
    1,868 sq. ft.
    S/S Thurs. Aug. 6, offers presented Tues. Aug.11 after 6:00 pm. Numerous updates throughout this fantastic 1,800 sq. ft. bungalow with cab-over in sought-after Linden Woods! This home is situated on a beautifully landscaped lot with an incredible backyard designed for entertaining. The spacious LR & DR feature hwds & a vaulted ceiling, creating a bright, inviting space for family gatherings. The updated kit boasts granite countertops, a lg island w/built-in table, cabinetry with pull-outs & patio drs leading to a tiered deck with pergola. The kit overlooks the cozy FR with a FP, providing an ideal open-concept layout. The private primary suite features a wicc & a 3 pce ensuite. 2 additional bedrooms, a convenient main flr laundry rm & a 4 pce bath complete the main level. The updated lower level (2022) offers high ceilings, a spacious rec rm, games rm, 4th br & an additional 4 pce bath, perfect for family living or guests. Step outside to the spectacular backyard featuring a patio with fire pit, plenty of green space for kids to play & multiple areas to relax or entertain. Additional features include a HEF 2022, A/c 2019, HWT 2026 & an attached AT/2. An exceptional family home just move in and enjoy! More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 14 Duluth Bay in Winnipeg: Windsor Park Residential for sale (2G) : MLS®# 202618761

    14 Duluth Bay Windsor Park Winnipeg R2J 1W5
    Main Photo: 14 Duluth Bay in Winnipeg: Windsor Park Residential for sale (2G) : MLS®# 202618761

    14 Duluth Bay Winnipeg R2J 1W5 Windsor Park

    $429,900
    Residential
    Status:
    Active
    MLS® Num:
    202618761
    Bedrooms:
    4
    Bathrooms:
    2
    Floor Area:
    1,083 sq. ft.
    S/S Wed. Aug. 5, offers presented Mon. Aug.10. Beautifully updated bungalow tucked away on a quiet bay in Windsor Park! This move-in ready family home offers a bright open-concept layout with newer flooring, expansive windows & crown moulding in the living & dining rooms. The renovated kitchen features white soft-close cabinetry w/under-cabinet lighting, organizers, large island w/breakfast bar seating & ample workspace. A barn door in the dining room adds character while concealing a convenient storage closet. Three spacious bedrooms & an updated 4-piece bath complete the main level. The fully finished basement expands your living space with an entertainment-sized rec room, guest bedroom area, plus potential for a fifth bedroom, home office or gym. Updated 4-piece bath & laundry room. Enjoy the private, fully fenced east facing backyard w/patio, perfect for relaxing or entertaining. An oversized single detached garage & extra-long driveway provide excellent parking. Additional updates include a HEF/AC (2023), roof, windows & hot water tank, C/VAC, sump pump. Ideally located just steps to schools, parks, outdoor pool, transit & shopping. Look no further...this is the perfect place to call home! More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 6975 ROBLIN Boulevard in Headingley: Headingley South Residential for sale (1W) : MLS®# 202618758

    6975 ROBLIN Boulevard Headingley South Headingley R4H 1A2
    Main Photo: 6975 ROBLIN Boulevard in Headingley: Headingley South Residential for sale (1W) : MLS®# 202618758

    6975 ROBLIN Boulevard Headingley R4H 1A2 Headingley South

    $1,250,000
    Residential
    Status:
    Active
    MLS® Num:
    202618758
    Bedrooms:
    4
    Bathrooms:
    4
    Floor Area:
    2,064 sq. ft.
    S/S Wed. Aug.5, offers Wed. Aug.12. Drive down a winding private lane to this beautiful walkout bungalow, nestled on the riverfront & surrounded by picturesque green space. Designed with an open-concept layout, the spacious GR & DR feature maple hwds, a dramatic wall of windows, cozy gas FP & garden drs leading to a spacious covered deck. The well-appointed kit features abundant cabinetry, a lg granite-topped island that provides generous prep & workspace & included appliances, making it perfect for everyday living & effortless entertaining. A flexible main-flr office can easily serve as a 3rd br if desired. The main level includes 2 brs highlighted by the luxurious primary suite w/5 pce ensuite & WICC. You will also find a convenient laundry rm, a 2 pce powder rm, a 4 pce bath & a mud rm with direct access to the O/S triple attached garage. Fully finished lower level features newer hwds, a spacious recreation rm, a games rm with a wet bar & garden drs opening to the beautifully treed backyard, a theatre rm, gym, 2 additional brs & a 4 pce bath. This exceptional property combines privacy, spectacular natural surroundings & thoughtfully designed living spaces, making it the perfect place to call home. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 1324 Wellington Crescent in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202618959

    1324 Wellington Crescent River Heights North Winnipeg R3N 0B1
    Main Photo: 1324 Wellington Crescent in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202618959

    1324 Wellington Crescent Winnipeg R3N 0B1 River Heights North

    $997,500
    Residential
    Status:
    Active
    MLS® Num:
    202618959
    Bedrooms:
    3
    Bathrooms:
    2
    Floor Area:
    1,560 sq. ft.
    S/S now, offers presented as rec'd. Prestigious Wellington Crescent living just steps from the scenic tree-lined walking path! This architecturally designed residence showcases exceptional craftsmanship, timeless elegance & sophisticated finishes throughout. The inviting LR features a dramatic floor-to-ceiling bay window, custom art niches & a charming wood-burning fireplace. Patio doors from the DR open to a beautifully landscaped, fully fenced backyard w/ tiered deck, creating the perfect space for outdoor entertaining & relaxing. The thoughtfully designed kitchen offers Bosch gas cooktop & wall oven, pull-out organizers & abundant cabinetry for exceptional storage & functionality. A mezzanine office or reading nook provides a bright & versatile retreat. Upstairs, the spacious primary suite features a cozy gas fireplace, dual closets & direct access to a luxurious 5-piece bath. The fully finished LL expands the living space w/a generous rec room featuring a gas fireplace, guest bedroom, 3-piece bath & convenient laundry area. Ideally located in one of Winnipeg's most coveted neighbourhoods, this exceptional home offers the perfect blend of style, comfort & an unbeatable Wellington Crescent address. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 1 393 Wellington Crescent in Winnipeg: Crescentwood Condominium for sale (1B) : MLS®# 202618922

    1 393 Wellington Crescent Crescentwood Winnipeg R3M 0A1
    Main Photo: 1 393 Wellington Crescent in Winnipeg: Crescentwood Condominium for sale (1B) : MLS®# 202618922

    1 393 Wellington Crescent Winnipeg R3M 0A1 Crescentwood

    $499,900
    Condominium
    Status:
    Active
    MLS® Num:
    202618922
    Bedrooms:
    3
    Bathrooms:
    3
    Floor Area:
    1,981 sq. ft.
    S/S now, offers presented as rec'd. Experience carefree riverfront living in this beautifully appointed condominium, ideally located just steps from the scenic Wellington Crescent walking path. A grand foyer welcomes you into the elegant living & dining rooms, where rich crown moulding & a charming wood-burning fireplace create a warm & inviting atmosphere. The bright sunroom features garden doors leading to a private deck overlooking the river...perfect place to relax!. A cozy den offers the perfect space for reading, working from home or quiet relaxation. The spacious kitchen is designed for both style & function w/granite counters, pull-out organizers & adjoining FR for casual everyday living. The private primary suite is a peaceful retreat featuring custom built-ins, a 3-piece ensuite & picturesque views of Munson Park. An elevator provides convenient access to the fully finished LL, offering two more brs, a 4-piece bath, laundry room & large utility room w/abundant storage. Additional features include C/AIR, C/VAC, heated & insulated AT/2 & private storage locker. An exceptional opportunity to enjoy spacious, low-maintenance living in one of Winnipeg's most sought-after riverfront locations. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 19 GOLDEN OAK Cove in Cartier Rm: RM of Cartier Residential for sale (R10) : MLS®# 202615285

    19 GOLDEN OAK Cove RM of Cartier Cartier Rm R4K 1B3
    Main Photo: 19 GOLDEN OAK Cove in Cartier Rm: RM of Cartier Residential for sale (R10) : MLS®# 202615285

    19 GOLDEN OAK Cove Cartier Rm R4K 1B3 RM of Cartier

    $799,900
    Residential
    Status:
    Active
    MLS® Num:
    202615285
    Bedrooms:
    3
    Bathrooms:
    3
    Floor Area:
    2,366 sq. ft.
    S/S Sat. July 25, offers presented as rec'd. Gorgeous Tudor-style 2-storey nestled among mature trees on a quiet no-through road on a 3.06 acre lot. Lovingly maintained by its long-time owners, this exceptional home showcases timeless charm with gleaming hardwood floors, solid oak doors & trim & quality craftsmanship throughout. Formal LR & DR feature crown moulding & large windows framing picturesque views. The updated kit offers granite counters, stainless appliances, under-cabinet lighting, appliance garage, VacuSweep vent & island w/seating. A sunken family room w/wood-burning brick fireplace opens through French doors to a bright 4-season sunroom overlooking the deck & natural landscape. Main floor laundry & bath. Upstairs offers 3 bedrooms, including a spacious primary w/WICC & 4-piece ensuite. Family 4-piece bath. Full basement with RIP for a 4th bath awaits your finishing touches. Heated AT/2 plus DT/3 36' x 26' heated garage/workshop is ideal for hobbyists or a home business Piled foundation, updated Thermopane windows, C/AIR (2022), house shingles (2017), supplemental wood-burning furnace, C/VAC, sump pump. Less than 20 minutes to Winnipeg & minutes to St. François Xavier amenities. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 8667 ROBLIN Boulevard in Headingley: Headingley South Residential for sale (1W) : MLS®# 202617374

    8667 ROBLIN Boulevard Headingley South Headingley R4J 1B7
    Main Photo: 8667 ROBLIN Boulevard in Headingley: Headingley South Residential for sale (1W) : MLS®# 202617374

    8667 ROBLIN Boulevard Headingley R4J 1B7 Headingley South

    $524,900
    Residential
    Status:
    Active
    MLS® Num:
    202617374
    Bedrooms:
    3
    Bathrooms:
    1
    Floor Area:
    1,200 sq. ft.
    S/S immediately, offers presented as received. Fabulous opportunity to build your dream home in South Headingley! Boasting 275' of Assiniboine River frontage, this exceptional property offers a spectacular setting to build your dream home. Nestled among mature trees in a peaceful location, you'll enjoy stunning river views and the tranquility of nature while remaining close to city conveniences. The existing home is being sold as-is and is best suited for redevelopment, presenting an incredible opportunity to create a custom residence on one of the area's most desirable riverfront properties. A truly rare chance to secure an expansive Assiniboine River lot with endless possibilities. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 646 Wellington Crescent in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202616703

    646 Wellington Crescent River Heights North Winnipeg R3M 0C2
    Main Photo: 646 Wellington Crescent in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202616703

    646 Wellington Crescent Winnipeg R3M 0C2 River Heights North

    $1,500,000
    Residential
    Status:
    Active
    MLS® Num:
    202616703
    Bedrooms:
    6
    Bathrooms:
    5
    Floor Area:
    3,141 sq. ft.
    Exceptional modern design by renowned architect Lloyd Secter, this stunning residence on prestigious Wellington Crescent offers over 3000 sq. ft. of thoughtfully designed living space. Showcasing sophisticated finishes & an exceptional layout, this remarkable home blends style, comfort & functionality in one of the city's most coveted locations. The spacious living & dining room showcases a stunning floor-to-ceiling window that floods the space with natural light, complemented by a FP & designer cabinetry. Top-of-the-line chef's kitchen features custom cabinets, premium appliances & an expansive island overlooking the inviting FR, creating the perfect space for everyday living & effortless entertaining. The upper level features a spacious primary retreat w/private balcony & luxurious 6-piece ensuite, along w/3 additional generously sized brs, office & a 4-piece bath. Newly carpeted LL offers a bright recreation rm with lg windows, a wet bar plus additional br & a 4-piece bath. Covered deck overlooking the expansive, fully fenced backyard—an ideal setting for outdoor entertaining. Built on piles with a structural concrete basement floor. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • 201 188 Roslyn Road in Winnipeg: Osborne Village Condominium for sale (1B) : MLS®# 202615281

    201 188 Roslyn Road Osborne Village Winnipeg R3L 0G8
    Main Photo: 201 188 Roslyn Road in Winnipeg: Osborne Village Condominium for sale (1B) : MLS®# 202615281

    201 188 Roslyn Road Winnipeg R3L 0G8 Osborne Village

    $158,900
    Condominium
    Status:
    Active
    MLS® Num:
    202615281
    Bedrooms:
    1
    Bathrooms:
    1
    Floor Area:
    742 sq. ft.
    Location, location, location! Freshly updated with new paint and flooring, this affordable 1-bedroom condo is perfectly situated in the heart of Osborne Village. The bright open-concept kitchen, dining and living areas create a comfortable space for everyday living and entertaining, while the breakfast bar peninsula offers additional seating. Patio doors lead to a west-facing balcony complete with screens, allowing you to enjoy fresh air, morning coffee, or evening cocktails in comfort. A wall of hallway closets provides excellent storage and the spacious 4-piece bath adds convenience. The bright bedroom features a built-in desk and bookcases, making it ideal for working from home or creating a cozy reading nook. Shared laundry is conveniently located on the same floor. This pet-friendly building offers elevator access and one underground parking stall. Enjoy an unbeatable walkable lifestyle just steps from Osborne Village's vibrant restaurants, cafés, boutiques, and nightlife, with easy access to Wellington Crescent, downtown, The Forks, and scenic river pathways. A fantastic opportunity for first-time buyers, downsizing, or investors! More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK

  • B 711 Niagara Street in Winnipeg: River Heights Condominium for sale (1D) : MLS®# 202613146

    B 711 Niagara Street River Heights Winnipeg R3N 0W2
    Main Photo: B 711 Niagara Street in Winnipeg: River Heights Condominium for sale (1D) : MLS®# 202613146

    B 711 Niagara Street Winnipeg R3N 0W2 River Heights

    $369,900
    Condominium
    Status:
    Active
    MLS® Num:
    202613146
    Bedrooms:
    2
    Bathrooms:
    2
    Floor Area:
    1,645 sq. ft.
    Rarely available 1645 sf two-storey condo in a distinctive building offering bright, spacious living with a unique layout. The main floor features a generous foyer that could easily double as a sunroom or home office, a bedroom & a bright living area highlighted by a wall of windows w/direct access to the shared outdoor space. Upstairs, vaulted ceilings & skylights create an airy atmosphere throughout the open-concept living & dining areas. The island kit offers abundant cabinetry, ss appliances & breakfast bar seating, making it ideal for everyday living & entertaining. The spacious primary bedroom features soaring vaulted ceilings, skylight, wall of windows, WICC & private 4-piece ensuite. The LL has additional storage & access to your own private laundry room. Outdoor amenities include a beautifully maintained south-facing shared courtyard w/large patio, firepit area & greenspace...perfect for relaxing or socializing. Each unit also has its own storage shed. 2 outdoor parking stalls. Located in the heart of River Heights, this exceptional condo is within walking distance to shops, restaurants & everyday amenities. Minutes from Assiniboine Park. More details
    Listed by Royal LePage Dynamic Real Estate
    LISTING DETAILS
    CHRIS PENNYCOOK
1-12/463
 <  123...39  > 
Data was last updated August 5, 2026 at 02:35 PM (UTC)
The enclosed information while deemed to be correct, is not guaranteed.

Buying a Property?

Selling a Property?

Chris Pennycook

I make myself available at all times. When you are ready to see a listing in person, or just have a simple question, please don't hesitate to contact me!

 

READ MORE

Contact Me

Chris Pennycook

Office 204-989-5000

chrispennycook@royallepage.ca

 

3 - 1450 Corydon Avenue

Winnipeg, MB

R3N 0J3

Send Me A Message

Powered by myRealPage.com