Chris Pennycook
Office 204-989-5000 | chrispennycook@royallepage.ca
My Listings
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53 Bremner Drive in Headingley: Taylor Farm Residential for sale (5W) : MLS®# 202604069
53 Bremner Drive Headingley R4H 0C8 
$1,175,000Residential- Status:
- Active
- MLS® Num:
- 202604069
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 2,001 sq. ft.
Custom bungalow currently under construction with no expense spared & exceptional attention to detail throughout. Designed with timeless style, the home features stunning archways, warm hardwoods & elegant porcelain tile complemented by black fixtures & soft neutral tones. Custom millwork & soft-close cabinetry highlight the craftsmanship found in every space. The dining space showcases a striking arched bar w/smoked glass mirror backsplash, perfect for entertaining. The thoughtfully designed kit features stone countertops & backsplash, a custom pantry & a beautiful lime wash plaster range hood creating a true focal point. The primary retreat offers custom built-in millwork & a luxurious 5-piece ensuite w/double vanity & relaxing steam shower. In total the home offers 3 bedrooms along w/convenient main floor laundry. Modern mechanicals include a dual-zone HEF, C/AIR & HRV system. New home warranty. Insulated bsmt. Enjoy outdoor living w/a welcoming covered front porch & spacious 16' x 14' covered rear deck ideal for relaxing or entertaining. AT/3. Located in the desirable community of Taylor Farm, this home offers the perfect balance of peaceful country surroundings w/city conveniences minutes away. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
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1278 Wellington Crescent in Winnipeg: River Heights North Rental for rent (1C) : MLS®# 202604438
1278 Wellington Crescent Winnipeg R3M 3P8
$3,850Rental- Status:
- For Rent
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 4,088 sq. ft.
AVAILBLE IMMEDIATELY! $3850.00 per month plus utilities on this 4,000 sq. ft. two-and-a-half storey nestled on a sprawling lot along iconic Wellington Crescent. Just steps from scenic riverside walking paths leading to Assiniboine Park and a short stroll to the boutiques and eateries of Academy Road. Rich with character, the home features a spacious family room addition with a cozy fireplace, perfect for relaxing or entertaining. The kitchen offers ample cabinetry and space for casual dining. The second floor features three generous bedrooms, including a primary with its own ensuite, and an updated 4-piece family bath. The third floor provides flexible living with a private office and a large bedroom complete with its own ensuite—ideal for guests or a growing family. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
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175 Ridgedale Crescent in Winnipeg: Charleswood Residential for sale (1F) : MLS®# 202603088
175 Ridgedale Crescent Winnipeg R3R 0B4
$2,600,000Residential- Status:
- Active
- MLS® Num:
- 202603088
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 3,093 sq. ft.
S/S Sat. Mar. 14, offers as rec'd. Stunning 1.4-acre riverfront estate in prestigious neighbourhood, offering panoramic views of the Assiniboine River & manicured grounds from every room. This custom two-storey is impeccably maintained & richly appointed w/endless luxuries. The main floor showcases a refined LR w/custom millwork, gas fireplace & double doors to a spectacular outdoor space featuring floor-to-ceiling drop screens & gas BBQ hookup. The dining room is wrapped in windows w/automated blinds & serene front yard views. A private office w/glass sliding doors, custom mudroom w/laundry hookups & elegant 2-piece bath add function. The gourmet eat-in kit boasts a expansive island w/butcher block & quartz, Sub-Zero fridge, WOLF wall ovens & gas cooktop, stone slab backsplash, pot filler, pantry wall & wet bar. Upstairs offers 3 bedrooms, laundry & breathtaking primary retreat w/custom WICC, spa-inspired ensuite w/large shower plus river-facing deck w/covered hot tub. The walkout LL includes a rec room, gym, br & full bath. Control4 automation, hide-a-hose vacuum, steel beam construction, o/s DT/3, pool, 2 hot tubs, tiered deck & beautiful landscaped grounds complete this extraordinary property! More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
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82 Hopwood Drive in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202603867
82 Hopwood Drive Winnipeg R3P 0Z5
$1,999,000Residential- Status:
- Pending
- MLS® Num:
- 202603867
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 2,750 sq. ft.
S/S Sat. Mar. 7, offers as rec'd. Complete renovation by DLUX Design in 2021 transformed this exceptional home into a light-filled showpiece. A grand foyer w/soaring 16-foot ceiling & dramatic floor-to-ceiling wood moulding accent wall sets the tone. The formal DR features a custom ceiling, statement pendant lighting & space for large gatherings. Wide plank oak hardwood floors flow throughout the main & upper levels. A private office w/double glass doors offers built-in bookcases w/desk & crown moulding. The gourmet kit impresses w/soft-close cabinetry, quartz counters & backsplash, Wolf 6-burner gas cooktop w/custom hood, integrated fridge & dishwasher plus an oak island w/breakfast bar. A butler’s pantry, mudroom & laundry add function. The bright FR overlooks the backyard oasis & features a gas fireplace flanked by built-ins. Upstairs offers 3 bedrooms, including a luxurious primary w/spa-like ensuite & custom WICC. The 2 other bedrooms share an ensuite. The LL is ideal for entertaining w/rec space, wet bar, gym, 4th br & heated tile bath. The spectacular outdoor space boasts one of the largest lots on the street & features an inground pool, hot tub, outdoor kitchen & covered lounge area. AT/2. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
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30 Aldershot Boulevard in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202604046
30 Aldershot Boulevard Winnipeg R3P 0C8
$2,249,900Residential- Status:
- Active
- MLS® Num:
- 202604046
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 2,987 sq. ft.
S/S now, offers as rec'd. Fully renovated top to bottom in 2025, this stunning home offers exceptional craftsmanship, quality finishes & thoughtful custom details throughout. The impressive GR features soaring floor-to-ceiling windows, custom built-ins, cozy fp & access to the deck, creating a bright & inviting space. The elegant DR is perfect for entertaining w/a stylish wet bar & custom wine display. The gourmet kit boasts soft-close cabinetry, high-end appliances, quartz counters, fully equipped butler’s pantry & a family-size island w/attached dining table. A main floor office w/built-ins, guest bath & bedroom w/private 4-piece ensuite provide excellent flexibility. Upstairs, the primary suite features custom wall detailing, a dream WICC & a luxurious spa-inspired 5-piece ensuite w/heated floors, soaker tub & dual sinks. Two additional brs share a spacious 5-piece bath. Convenient UL laundry. The finished LL includes a rec room w/dry bar, games area, br & 3-piece bath. All mechanical systems are new including 2 HEF, 2 C/AIR, HRV & sump pump. The expansive outdoor space offers plenty of space for a pool, sunroom & more. AT/2. Ideally located close to shopping, parks, restaurants & coffee shops. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
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214 4314 Grant Avenue in Winnipeg: Charleswood Condominium for sale (1G) : MLS®# 202603089
214 4314 Grant Avenue Winnipeg R3R 3V2
$339,900Condominium- Status:
- Active
- MLS® Num:
- 202603089
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,319 sq. ft.
Rare opportunity to this 3-bedroom, top-floor unit in a desirable & quiet condo building. Bright, updated & exceptionally well maintained, this home features newer laminate flooring & fresh paint throughout. The galley-style eat-in kitchen offers an abundance of cabinetry, all appliances & a newer patio door leading to a large covered balcony overlooking peaceful treed views. A pocket door provides added privacy to the spacious LR, while the open living & dining areas create an inviting space for everyday living & entertaining. The thoughtful layout includes a private guest bedroom with adjacent 3-piece bath, while the primary suite features its own 4-piece ensuite. The versatile third bedroom is ideal as an office, den or gym. Convenient in-suite laundry w/storage. Residents enjoy excellent amenities including a large party room perfect for family gatherings, plus storage lockers located on the same floor. Outdoor parking stall #32 is included, with option to rent a second space. Condo fees cover parking & all utilities for worry-free living. Ideally located steps to the curling club & arena. Minutes to shopping, restaurants & everyday conveniences. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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184 Lindsay Street in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202603502
184 Lindsay Street Winnipeg R3N 1H1
$924,900Residential- Status:
- Active
- MLS® Num:
- 202603502
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 1,668 sq. ft.
OPEN HOUSE SATURDAY MARCH 14 & SUNDAY MARCH 15, 12:00-2:00 PM. . Brand new executive custom build in desirable North River Heights showcasing exceptional design, premium finishes & striking curb appeal w/acrylic stucco, contemporary masonry & o/s stacked windows w/black trim. Built on a piled foundation, this home features commercial-grade luxury vinyl plank flooring, expansive windows & impressive 9 & 10-foot ceilings throughout the main & upper levels. The spacious foyer opens to an elegant dining area & stunning culinary kit w/illuminated waterfall island, Dekton counters, soft-close push cabinetry & high end LG appliances. A convenient main floor guest bath & sunken LR w/access to the east-facing deck complete the level. Upstairs offers three bedrooms, including a luxurious primary retreat w/vaulted cathedral ceiling, spa-inspired 5-piece ensuite w/heated floors, wet room & custom WICC. UL laundry & private office add flexibility. The LL offers potential for a secondary suite w/separate entry, wet bar, custom illuminated millwork, bedroom, laundry hookups & independent mechanical systems. Smart Home features & heated DT/2 wired for EV complete this stunning home. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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501 280 Waterfront Drive in Winnipeg: Exchange District Condominium for sale (9A) : MLS®# 202602655
501 280 Waterfront Drive Winnipeg R3B 0C2
$514,900Condominium- Status:
- Active
- MLS® Num:
- 202602655
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 1,424 sq. ft.
Experience the best of urban living in this bright & immaculate condo located in the heart of the Exchange District, offering amazing panoramic views of the city and Red River. This bright and spacious 2-bedroom plus den corner unit features gleaming hardwood floors throughout the main living area and den. The open-concept design showcases expansive windows with amazing views from every room. Welcoming living room w/gas fireplace, adjoining dining area w/patio doors to the wraparound balcony & a modern island kitchen w/granite counters, tile backsplash, stainless appliances & ample cabinetry. A breakfast bar provides a perfect spot for casual dining. The primary bedroom includes a Juliette balcony, WICC & relaxing 4-piece ensuite w/air tub. Additional highlights include a spacious foyer, in-suite laundry w/storage & a heated underground parking (stall #8), across from elevator. Pet friendly building & professionally managed. Enjoy the shared courtyard with 290 Waterfront & the unbeatable location...just steps to the riverwalk, parks, dining, entertainment & Winnipeg’s top attractions. Nothing to do but move in & enjoy carefree condo living at its finest! More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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66 Cummings Crescent in Winnipeg: River Park South Residential for sale (2F) : MLS®# 202601135
66 Cummings Crescent Winnipeg R2N 3P4
$629,900Residential- Status:
- Pending
- MLS® Num:
- 202601135
- Bedrooms:
- 3
- Bathrooms:
- 4
- Floor Area:
- 1,862 sq. ft.
This excellent family home is located on a prime lot in River Park South. Beautiful hardwoods highlight the entertainment-sized living & dining rooms. The sunken family room features a vaulted ceiling w/skylight, cozy wood-burning fireplace & remote pop-up TV. A wall of windows in the DR overlooks the low-maintenance backyard, while a garden door leads to the inviting sunroom. The family-sized kitchen offers ample cabinetry, ss appliances & island w/granite countertop & breakfast bar. A convenient 2-piece guest bath completes the main floor. Upstairs you will find 3 spacious bedrooms, including the primary featuring a modern updated 4-piece ensuite w/double vanity & soaker tub. Updated 3-piece family bath. Designed for entertaining & family fun, the fully finished bsmt includes a theatre area, games area, office & updated 3-piece bath. The south-facing backyard boasts a tiered deck with hot tub, paver stone patio, pergola w/privacy screens & mature perennials. Updates include C/AIR (2023), windows & shingles (2016). Sump pump, C/VAC & AT/2. Close to schools & shopping. Meticulously maintained & cared for with pride of ownership throughout. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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808 255 Wellington Crescent in Winnipeg: Crescentwood Condominium for sale (1B) : MLS®# 202600738
808 255 Wellington Crescent Winnipeg R3M 3V4
$399,900Condominium- Status:
- Active
- MLS® Num:
- 202600738
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 1,214 sq. ft.
Pride of ownership shines throughout this beautifully maintained 2-bedroom, 1.5-bath residence in a sought-after building on iconic Wellington Crescent. Bright and open, the layout features gleaming hardwood floors & ample lighting, all complimented by a southwest-facing balcony with lovely views. The kitchen offers an abundance of white cabinetry, granite countertops, a double oven & tiered island with breakfast bar seating...perfect for casual meals. Both bedrooms feature large windows and share the same sunny southwest exposure, while the primary includes a walk-in closet and a 4-piece ensuite. Enjoy the ease of in-suite laundry and the added convenience of extra storage located on the same floor. Two heated underground parking stalls with storage (51 & 52) are included. Outstanding building amenities include a party room, fitness centre, kitchenette & outdoor patio. Pet friendly and ideally located within walking distance to Osborne Village and scenic river pathways. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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39 Nanton Boulevard in Winnipeg: Tuxedo Rental for rent (1E) : MLS®# 202516669
39 Nanton Boulevard Winnipeg R3P 0N1
$8,500Rental- Status:
- For Rent
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 3,668 sq. ft.
S/S immediately. AVAILABLE TO RENT NOW! Extensively renovated over the years, this home offers a stunning family room addition showcasing vaulted beamed ceilings, a dramatic chateau-style fireplace, and five sets of French doors leading to the beautifully landscaped yard—perfect for entertaining inside and out. The gourmet eat-in kitchen is a chef’s dream, equipped with premium appliances, while the elegant formal dining room, complete with fireplace, sets the tone for memorable gatherings. Upstairs you’ll find five spacious bedrooms, three with their own ensuite baths, including a generous primary suite. The finished lower level includes a cozy family room with fireplace and bar, a 2-piece bath, laundry area, and ample storage. Rich in history, charm, and function, this is a truly exceptional home in one of the city’s most desirable neighborhoods. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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403 Churchill Drive in Winnipeg: Riverview Rental for rent (1A) : MLS®# 202603456
403 Churchill Drive Winnipeg R3L 1W2
$3,850Rental- Status:
- Rented
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,400 sq. ft.
S/S immediately. AVAILABLE TO RENT NOW! Completely renovated Riverview bungalow. 2 bedrooms & 2 baths on the main floor. Lower level family room with 3rd bedroom, office/gym & full bathroom. Newer windows & mechanicals. Laundry in basement. Fenced backyard with deck & sauna. Double detached garage. Great location, steps from walking paths & parks. Minutes to downtown, shopping & dining. Dogs allowed but no cats. More detailsListed by Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
Data was last updated March 12, 2026 at 08:35 PM (UTC)
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!
Contact Me
Chris Pennycook
Office 204-989-5000
3 - 1450 Corydon Avenue
Winnipeg, MB
R3N 0J3