Chris Pennycook
Office 204-989-5000 | chrispennycook@royallepage.ca
My Listings
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90 Empire Street in Headingley: Headingley South Residential for sale (1W) : MLS®# 202601220
90 Empire Street Headingley R4H 1A6 
$1,199,900Residential- Status:
- Active
- MLS® Num:
- 202601220
- Bedrooms:
- 5
- Bathrooms:
- 3
- Floor Area:
- 2,050 sq. ft.
S/S Thurs. Feb.5, offers as rec'd. Located in South Headingley on a private & 1.24-acre treed lot, this custom Huntington build showcases impressive upgrades throughout & backs onto a scenic walking path & steps from the Assiniboine River...perfect for year-round outdoor enjoyment. Custom Visions cabinetry is featured throughout, along w/surround sound, structural wood basement floors & recycled leather floors in the main living areas. A wall of windows fills the LR w/natural light, complimented by custom lit built-ins & gas fp. The DR offers space for large gatherings w/floating buffet & accent lighting. The entertainer’s kit impresses w/maple cabinetry, quartz counters, ss appliances & massive island w/2-sided breakfast bar. Garden doors open to a tiered north-facing deck, while patio doors lead to an inviting 3-season sunroom. The primary retreat overlooks the serenity of nature & includes a luxurious ensuite w/WICC. 2 additional brs, full bath & laundry/mudroom connect to the o/s triple car garage. The bright LL features a rec room & games room w/barn wood accent wall & dry bar. 2 more brs/flex spaces, full bath & abundant storage. An exceptional home, lovingly maintained on an incredible property 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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307 Park Boulevard in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202601424
307 Park Boulevard Winnipeg R3P 0G8
$1,324,900Residential- Status:
- Active
- MLS® Num:
- 202601424
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 2,295 sq. ft.
S/S Thurs. Feb. 5, offers Tues. Feb. 10. Located on a desirable street in Tuxedo, this modern & inviting 2 storey family home is thoughtfully designed for comfortable living & entertaining. A bright open foyer welcomes you into the sun-filled LR featuring lovely hardwoods, oversized windows & custom feature wall w/gas fireplace & stainless surround. The spacious DR easily hosts gatherings, while the chef’s kitchen impresses w/high-end ss appliances, quartz counters, abundant custom cabinetry & family-size island w/double-sided breakfast bar. Relax or entertain in the adjacent FR. Garden doors lead to the deck & beautifully manicured backyard w/mature trees. Convenient 2-piece guest bath. A custom staircase leads to 3 brs & 2 baths. Expansive primary w/double doors & luxury 3-piece ensuite & WICC. An upper west-facing deck offers the perfect spot for morning coffee or sunset cocktails. The fully finished bsmt features a rec room w/wet bar, built-in storage & work space, striking lighted feature wall, 4th br, full bath & laundry. Exceptional curb appeal w/mature landscaping, double drive & 20' x 20' attached garage w/custom overhead door. Steps to Assiniboine Park. Close to shopping, cafés & dining. 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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20 1290 Warde Avenue in Winnipeg: Royalwood Condominium for sale (2J) : MLS®# 202529750
20 1290 Warde Avenue Winnipeg R3X 0L4
$459,900Condominium- Status:
- Active
- MLS® Num:
- 202529750
- Bedrooms:
- 2
- Bathrooms:
- 3
- Floor Area:
- 1,775 sq. ft.
S/S Sat. Feb. 7, offers presented as rec'd. Located in prestigious Royalwood Estates in south St. Vital, this townhomes offers the perfect balance of traditional single-family living with the carefree convenience of condo life. A spacious foyer welcomes you to the upper level open-concept design highlighted by beautiful maple hardwoods & luxurious upgrades. The LR features large windows w/silhouette blinds, custom built-in millwork with storage & electric linear fireplace w/elegant tile surround. The dining area offers additional custom storage & patio doors leading to north facing deck. The island kitchen is finished w/granite counters, breakfast bar seating, ss appliances & ample cabinetry. Convenient 2-piece bath. Upstairs are 2 generously sized bedrooms, each with good closet space, private ensuite baths & steps to the laundry closet. The bright lower-level flex space (ideal office or family room) has access to a covered patio & greenspace through large patio doors. Direct access to the double attached garage & plenty of storage options add to the functionality. Meticulously maintained, pet friendly & low condo fees make this a rare find. Easy access to shopping, dining & recreational activities. 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
$649,900Residential- Status:
- Active
- 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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135 Ash Street in Winnipeg: River Heights Residential for sale (1C) : MLS®# 202600366
135 Ash Street Winnipeg R3N 0P4
$1,995,000Residential- Status:
- Pending
- MLS® Num:
- 202600366
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 3,614 sq. ft.
S/S now, offers presented as received. A true architectural masterpiece by renowned builder Art Gross with architect Les Stechesen, this exceptional residence is set on beautifully landscaped grounds and showcases impeccable craftsmanship with a refined blend of luxury and sophistication. The home welcomes you with a striking sunken living room featuring a warm, inviting fireplace, while rich hardwood floors flow throughout. Elegant French doors lead to a formal dining room that comfortably seats 12 and opens to a patio—ideal for entertaining. The bright white chef’s kitchen is both stylish and functional, offering top-tier appliances, ample cabinetry, and a spacious dining area. A cozy yet refined library with its own fireplace provides the perfect retreat. Upstairs, the private upper level features a charming office, serene den, 3-piece bath, and three generous bedrooms, including a luxurious primary suite with a spa-inspired 5-piece ensuite and custom walk-in closet. The lower level impresses with a grand rec room highlighted by a dramatic stone wood-burning fireplace. Spacious double attached garage. Timeless elegance meets modern comfort in this truly extraordinary 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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34 Birkenhead Avenue in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202529379
34 Birkenhead Avenue Winnipeg R3P 0P1
$1,195,000Residential- Status:
- Active
- MLS® Num:
- 202529379
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 3,511 sq. ft.
S/S Thurs. Dec. 11, offers presented as rec'd. Spacious & bright family home in sought-after Tuxedo, set on a prime corner lot overlooking beautiful greenspace. This classic 2-storey is filled w/charm, elegance & room for the entire family. A double-door entry opens to a generous foyer, leading to a formal LR centered by a gas fireplace w/marble surround & a bay window flooding the space w/natural light. The formal DR is ideal for hosting large gatherings. A custom eat-in kitchen offers abundant cabinetry w/organizers, built-in fridge & 11' island w/slide-in range, breakfast bar & pendant lighting. Enjoy casual dining w/built-in bench seating & backyard views. The FR is perfect for entertaining, w/patio doors opening to the deck for seamless indoor-outdoor living. Main floor laundry & guest bath add everyday convenience. Upstairs features 4 large brs, including a primary w/WICC & 4-piece ensuite. 2 bedrooms share a 3-piece bath, plus there's an additional 3-piece bath...all with heated tile floors. 2 staircases lead to the bsmt that has a rec room w/wet bar & home theatre system...great for movie night. Plenty of storage & 2-piece bath. AT/2 plus carport. Updates include windows, 2 HEF, C/AIR x 2, HWT 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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303 Boreham Boulevard in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202528490
303 Boreham Boulevard Winnipeg R3P 0J7
$3,599,000Residential- Status:
- Active
- MLS® Num:
- 202528490
- Bedrooms:
- 4
- Bathrooms:
- 6
- Floor Area:
- 3,511 sq. ft.
Another extraordinary creation by DLUX Design & Company! This 3,511 sq. ft. Tuxedo showpiece blends cutting-edge design with luxurious finishes on one of the area’s most coveted streets—just steps from Assiniboine Park and The Leaf. The main floor features a gourmet kitchen with butler’s pantry, elegant dining room, striking great room with gas fireplace, spacious office & large mudroom. Upstairs offers a versatile family/flex space and three bedrooms, each with its own spa-inspired ensuite and walk-in closet, plus convenient second-floor laundry. The impressive LL is entertainment-ready with a massive rec room, games area with bar, home gym space and a fourth bedroom with ensuite and WICC. Two stylish powder rooms add ease to both the main & lower levels. Outdoors, enjoy a dining deck ideal for summer gatherings. Parking includes a triple attached garage w/tandem bay/workshop. Thoughtfully curated & truly one-of-a-kind, this DLUX home is fully turnkey & value added with high-end appliances, completed landscaping, window coverings & integrated security & sound. A newly completed home lets you save both time and money...your dream home is ready & waiting! 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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30 Aldershot Boulevard in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202527029
30 Aldershot Boulevard Winnipeg R3P 0C8
$2,274,900Residential- Status:
- Active
- MLS® Num:
- 202527029
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 2,987 sq. ft.
Fully renovated from top to bottom in 2025, this stunning home showcases high-quality finishes, exceptional craftsmanship & custom details throughout. The GR impresses w/floor-to-ceiling windows, custom built-ins, cozy fp & access to the deck. Entertain in style in the DR, complete w/wet bar & custom wine wall. The gourmet kitchen features soft-close cabinetry, high-end appliances, quartz counters, fully equipped butler's pantry & family-size island w/attached dining table. A main floor office w/built-ins, guest bath & bedroom w/4-piece ensuite add convenience. Upstairs, the primary bedroom boasts custom wall art, a dream WICC, luxurious spa 5-piece ensuite w/heated tile, soaker tub & dual sinks. 2 additional bedrooms share a 5-piece bath, perfect for the kids. UL laundry room. The finished LL includes a rec room w/dry bar, games area, large br & 3-piece bath. All new mechanical systems include 2 HEF, 2 C/A units, HRV & sump pump. The expansive backyard is ideal for entertaining or family fun...room for a pool, sun room, play structures & more. AT/2. Located close to shopping, restaurants, parks & coffee shops. This home is redesigned to impress! 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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15 101 Litchfield Boulevard in Winnipeg: Tuxedo Condominium for sale (1E) : MLS®# 202526666
15 101 Litchfield Boulevard Winnipeg R3P 2R4
$1,225,000Condominium- Status:
- Active
- MLS® Num:
- 202526666
- Bedrooms:
- 5
- Bathrooms:
- 4
- Floor Area:
- 2,390 sq. ft.
Immaculate & grand! This stunning home in the prestigious neighbourhood of Foxborough Cove offers elegance, comfort & exceptional design. An inviting foyer gleaming hardwoods & high ceilings sets the tone for this impressive condo. The formal dining room features elegant pillar accents & floor-to-ceiling windows, while the LR showcases a gas fireplace framed by expansive windows overlooking the deck. Perfect for entertaining, a dry bar with glassware storage & display compliments the space. The spacious eat-in kit boasts ample cabinetry, tiered island with breakfast bar & gas cook top. Bosch high-end stainless steel appliances. A 4-season sunroom with bi-fold glass doors extends the living area to the deck. The private primary suite offers a spa inspired 5-piece ensuite & WICC. A 2nd bedroom, 3-piece bath, laundry & mudroom complete the main level. The fully finished LL is an entertainer’s dream w/high ceilings, expansive rec area, 3 additional bedrooms...including a perfect nanny or in-law suite with ensuite, plus another full bath & storage room. Heated AT/2, C/AIR, C/VAC, sump pump. Steps to Shindleman Park & Assiniboine Forest. 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®# 202526276
501 280 Waterfront Drive Winnipeg R3B 0C2
$524,900Condominium- Status:
- Active
- MLS® Num:
- 202526276
- 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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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
Data was last updated February 7, 2026 at 10:35 AM (UTC)
Contact Me
Chris Pennycook
Office 204-989-5000
3 - 1450 Corydon Avenue
Winnipeg, MB
R3N 0J3