Chris Pennycook
Office 204-989-5000 | chrispennycook@royallepage.ca
Office Listings
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509 Shaftesbury Boulevard in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202611242
509 Shaftesbury Boulevard Winnipeg R3P 0M3 
$1,100,000Residential- Status:
- Active
- MLS® Num:
- 202611242
- Bedrooms:
- 4
- Bathrooms:
- 3
- Floor Area:
- 2,480 sq. ft.
Showings begin May 28. Offers June 2. Exceptional 2500 SF contemporary 4-bedroom home on an incredible 75 x 200 foot property — a true backyard paradise. Beautifully maintained, this architecturally distinctive home features dramatic spaces, exciting design & stunning floor-to-ceiling windows that flood the interior with natural light. Designed for both entertaining & comfortable family living, the main floor offers a warm, inviting living room with a striking fireplace, while the dining area stretches along the back of the home with beautiful views of the yard. The kitchen features a large eating area, pantry & opens to the spacious family room. A huge screened sunroom brings the outdoors in — the perfect place to enjoy a bug-free summer evening. Upstairs are 3 bedrooms plus the spacious primary suite, complete with a large ensuite bath, walk-in closet & private balcony overlooking the spectacular backyard. The lower level includes a rec room, laundry area, & large storage space. Outside, the enormous yard features a large deck, sport court & sculptural fountain — your private retreat. Located close to schools, Assiniboine Park, and the Tuxedo Golf Club. More detailsListed by Lainey Danzker and Nessa Werier of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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9 1815 Corydon Avenue in Winnipeg: River Heights North Condominium for sale (1C) : MLS®# 202611054
9 1815 Corydon Avenue Winnipeg R3N 0P2
$439,000Condominium- Status:
- Active
- MLS® Num:
- 202611054
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,080 sq. ft.
Showings Start Now with offers reviewed Thursday, May 27th // Rarely available North River Heights bungalow condominium. Enter through the private front porch to a bright open floor plan with Living/Dining Room and Kitchen. The main floor also features two Bedrooms including Primary with walk-through closet and full en-suite, second full Bathroom, and main floor Laundry. Developed basement with large Rec Room, third Bedroom, and full Bathroom. Attached single garage with access off of the back entry, plus a second outdoor parking spot just steps along the lane. More detailsListed by Claude Davis and Geoffrey Davis of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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1493 Wellington Crescent in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202611266
1493 Wellington Crescent Winnipeg R3N 0B6
$899,900Residential- Status:
- Active
- MLS® Num:
- 202611266
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 2,050 sq. ft.
Showings begin May 24. Outstanding example of Arts and Crafts style in a vibrant, walkable North River Heights location. More than a home, it is a lifestyle.Incredible character, rich woodwork & stunning stained glass define this truly unique home. Setting the tone is the welcoming front porch.Step inside the dramatic double-height foyer featuring a handsome staircase crafted from local elms. Gracious living room offers warmth & intimacy around the fireplace,& the dining area is a natural gathering place w/seamless connection to the well-equipped island kitchen.Beautiful sunroom overlooks the backyard retreat. 2 bedrooms & a full bath complete the main floor. Fabulous 2nd-floor loft dedicated to the primary suite, w/walk-in closet, ensuite bath & private balcony nestled among the trees. Lower level w rec room w/ gas fireplace,bar, 2-piece bath,office & laundry. Outstanding front & back gardens deserve special mention.Professionally landscaped w/natural prairie plantings,they are designed for beauty w/minimal maintenance.Serene Koi-inspired pond creates a magical, peaceful setting. Built in 1927,the home underwent extensive renos in 2012, incl electrical,plumbing,windows, HEF, central air & roof. More detailsListed by Lainey Danzker and Nessa Werier of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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401 1460 Portage Avenue in Winnipeg: Polo Park Condominium for sale (5C) : MLS®# 202611180
401 1460 Portage Avenue Winnipeg R3G 3M9
$144,900Condominium- Status:
- Active
- MLS® Num:
- 202611180
- Bedrooms:
- 2
- Bathrooms:
- 1
- Floor Area:
- 1,037 sq. ft.
Welcome to easy, carefree living in this well-maintained 55+ life lease community ideally located across from CF Polo Park and close to shopping, restaurants, public transportation, and all amenities. This quiet corner suite on the 4th floor offers desirable south & east exposure, filling the space with natural light while providing a peaceful setting within a quiet concrete building. The functional layout features an eat-in kitchen open to the living and dining area, creating a bright and comfortable space for everyday living. Both bedrooms offer double closets, and the suite includes a spacious 4-piece bathroom along with a convenient in-suite laundry/storage room. Step outside to the spacious east-facing balcony—the perfect place to enjoy your morning coffee and sunrise views. Residents appreciate the secure entrance, visitor parking, and excellent amenities including a fitness facility, large 2nd-floor balcony, party hall, library, and more. Condo fees include parking, water, and added conveniences, making for truly low-maintenance living. More detailsListed by Alix McIntyre of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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116 Foster Street in Winnipeg: East Elmwood Residential for sale (3B) : MLS®# 202611137
116 Foster Street Winnipeg R2L 1V9
$299,900Residential- Status:
- Active
- MLS® Num:
- 202611137
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 756 sq. ft.
SS now. Offers reviewed May 27/29. OPEN HOUSE SAT & SUN MAY 23/24 FROM 2-4PM. Looking for a solid starter home, rental or home to down size to? This may be it. Conveniently located in a quiet neighborhood is this hidden gem. This 4 bedroom 2 full bath house is ready for you to call it home. Complete with a fenced yard in the front and back, this offers you comfort and security. In the back yard is a beautiful insulated & heated double garage, with parking beside it and a fantastic area to entertain. Now when you walk in, you will see hardwood flooring and big bright windows in the living room area. Next we have 2 decent bedrooms and a bathroom as well as the kitchen area. Downstairs is finished with 2 more bedrooms (windows may not meet egress), a full bathroom, rec room with wet bar, mechanical room and laundry area. The house does have a new AC and HWT, fence, and some flooring. With a few more upgrades this home can shine! Did I mention there are schools and playgrounds very close as well?! Come and check out what could be your new home! **Room sizes are not currently accurate and will be corrected shortly. More detailsListed by Terry Hunter of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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14 301 Country Club Boulevard in Winnipeg: St Charles Condominium for sale (5G) : MLS®# 202610160
14 301 Country Club Boulevard Winnipeg R3V 2E4
$949,900Condominium- Status:
- Active
- MLS® Num:
- 202610160
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 2,182 sq. ft.
S/S SATURDAY, May 23-offers as received. Rarely available & impeccably renovated, this exceptional residence tucked away along Country Club Boulevard offers the ultimate in luxury condominium living. Showcasing exquisite craftsmanship, premium finishes & quality construction throughout, this stunning home is perfectly designed for both everyday comfort & grand-scale entertaining. Elegant arched doorways, beautiful hwds & sophisticated architectural details enhance the refined interior. The spacious LR features a cozy gas FP & an abundance of space for relaxing & entertaining in comfort & style. The elegant DR is accented with lovely crown moulding, while the fabulous white eat-in kitchen is a chef’s dream, complete with quartz countertops, an island cooktop, pantry pull-outs & access to an oversized private balcony overlooking the beautifully manicured St. Charles Golf Course.The private primary suite offers a lg wicc & a luxurious spa-inspired 4-piece ensuite with a relaxing soaker tub. A generous 2nd bedroom with a double closet, a stylish 3-piece bath with a walk-in shower, an impressive entranceway, convenient in-suite laundry rm & 2 heated underground parking stalls complete this incredible 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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420 Shelley Street in Winnipeg: Westwood Residential for sale (5G) : MLS®# 202611112
420 Shelley Street Winnipeg R3K 1G3
$550,000Residential- Status:
- Active
- MLS® Num:
- 202611112
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,533 sq. ft.
SS May 21/OTP May 26. Have you been looking for a newer (2004) build in wonderful Westwood with steel beam construction, welcoming front porch, double attached garage, and low-maintenance exterior? You FOUND it! Long-time owners have taken great care of this home and completed updates over the years, making it a worry-free option for the next family. Updates include furnace & A/C (’19), kitchen appliances (’23), shingles (’25), central vac unit (‘25), washer & dryer (’26). The inviting front porch creates the perfect first impression, while the attached garage with direct access adds everyday convenience. Inside offers a spacious foyer, comfortable living room, bright, functional, eat-in kitchen with corner pantry, main floor laundry, plenty of storage, and the convenient 2-piece bath. Upstairs features two similarly sized secondary bedrooms with ample storage as well as the full bathroom. The generous primary bedroom has a 3-piece en suite and walk-in closet. The insulated basement offers roughed-in plumbing and awaits your personal touch. Located close to parks, schools, and amenities, this family-friendly home offers the perfect blend of comfort, function, and location! Book your showing TODAY!! More detailsListed by Jennifer Sangster of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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1001 Jessie Avenue in Winnipeg: Crescentwood Residential for sale (1Bw) : MLS®# 202610464
1001 Jessie Avenue Winnipeg R3M 1A1
$499,900Residential- Status:
- Active
- MLS® Num:
- 202610464
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,504 sq. ft.
S/S Thurs. May 21, offers Sun. May 24 evening. OH SUN. MAY 24, 1-3 PM. Crescentwood gem tucked away on a quiet street just off Corydon Avenue. An inviting front heated sunroom offers the perfect spot for morning coffee or relaxing with a book. Lovely hardwoods flow throughout the living & dining areas, highlighted by a character fireplace w/electric insert & stacked stone surround. The DR overlooks the backyard & connects seamlessly to the updated kitchen featuring ample cabinetry, ss appliances, tile backsplash & walk-in pantry w/automated light. A family-sized tiered island w/built-in dishwasher, double sink, breakfast bar & pendant lighting makes entertaining effortless. Upstairs offers 3 brs & 2 updated baths, including a spacious primary retreat w/WICC & private 4-piece ensuite. The bsmt was professionally developed in 2024 & includes a cozy rec room w/office or play nook, 3-piece bath & laundry room. Numerous upgrades include C/AIR (2022), HRV, HEF, HWT (2014), plumbing, windows, electrical panel, siding & sump pump. The fenced backyard features a tiered deck, garden beds & newer fencing. DT/1 (2014) w/French drain completes this move-in ready home. Ideally located close to all essentials. 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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59 Kilroy Street in Winnipeg: Prairie Pointe Residential for sale (1R) : MLS®# 202611043
59 Kilroy Street Winnipeg R3Y 0Z3
$599,900Residential- Status:
- Active
- MLS® Num:
- 202611043
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,504 sq. ft.
OTP May 27 6pm. OH Sat & Sun 1-3pm. Measurements +/- jogs. Welcome to 59 Kilroy St., a stunning two-storey home in the desirable area of Prairie Pointe offering 1,504 SqFt of beautifully designed living space built in 2019. The main floor features impressive 9-ft ceilings and a huge living room highlighted by a massive 96" x 84" window that fills the space with incredible natural light, a beautiful dining area, and a spacious open-concept kitchen complete with taller kitchen cabinets, soft-close doors, and quartz countertops throughout the entire home, along with a convenient half bathroom. The upper level features elegant glass railings for the stairs, a huge primary bedroom with a walk-in closet and full ensuite bathroom, two additional good-sized bedrooms with plenty of windows, and another full bathroom. The insulated basement offers endless opportunities to finish to your own style and already includes 10 added electrical receptacles around the walls for extra convenience. Outside, enjoy the huge fenced backyard with a deck, a spacious 22' x 22.8' double attached garage, and a 20-foot wide driveway providing plenty of parking space. Close to all amenities! So book your showings today. More detailsListed by Raj Ghataura of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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525 Rosedale Avenue in Winnipeg: Lord Roberts Residential for sale (1Aw) : MLS®# 202610961
525 Rosedale Avenue Winnipeg R3L 1M4
$429,900Residential- Status:
- Active
- MLS® Num:
- 202610961
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,450 sq. ft.
Showings start Friday May 22 with offers reviewed Wednesday May 27 on this extensively remodelled 1,450 sq ft home offering the perfect balance of charm and modern comfort. Featuring 3 bedrooms and 2 bathrooms, this outstanding property is packed with upgrades inside and out. The beautifully refinished hardwood floors flow through the main living spaces, while the amazing mud room with custom benches adds practical everyday convenience. Enjoy cooking in your well appointed kitchen and entertain in the living/dining room combination. The primary bedroom retreat is absolutely spectacular, showcasing a full ensuite, walk-in closet and dressing area rarely found at this price point. Additional upgrades include electrical service, HRV system, high-efficiency furnace, all PVC windows, central air conditioning, shingles - new on the main house just this past long weekend! The fenced yard, composite deck, and 2 car parking complete the exterior. There's so much more to offer but not enough room to describe here. Situated near schools and parks, this property combines comfort, convenience, and quality craftsmanship in one incredible package. A home you truly need to experience in person! More detailsListed by Kristen Bilodeau of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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449 Lyndale Drive in Winnipeg: Norwood Flats Residential for sale (2B) : MLS®# 202607957
449 Lyndale Drive Winnipeg R2H 1M8
$999,900Residential- Status:
- Active
- MLS® Num:
- 202607957
- Bedrooms:
- 3
- Bathrooms:
- 4
- Floor Area:
- 2,539 sq. ft.
S/S Thurs, May 21-offers presented Tues, May 26 after 6:00 pm. Welcome to this beautifully appointed home offering outstanding curb appeal & fantastic river views. Enjoy your morning coffee on the inviting front deck while taking in the peaceful water views & serene surroundings. Designed for entertaining, host guests in the elegant formal living & dining rms featuring a stylish dry bar, hwds & charming cove ceilings. Remodelled kit complete with built-in oven, spacious island with breakfast bar & an abundance of cabinetry. The bright 4-season sunroom features heated flooring & garden drs leading to a private deck—perfect for year-round enjoyment. Inviting sunken FR offers a warm & inviting retreat with a gas FP. The main flr br currently used as a gym features cork flooring adding both comfort & versatility. Upstairs, you will find a den/office with its own gas FP & fabulous view, along with a luxurious primary suite offering a 5-piece ensuite. A 2nd br & full 4-piece bath complete the upper level. The fully finished lower level includes a theatre rm & 3-piece bath, ideal for movie nights. Additional highlights include an attached oversized heated garage & exceptional outdoor space for entertaining. 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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32 Whidden Gate in Winnipeg: Linden Woods Residential for sale (1M) : MLS®# 202608666
32 Whidden Gate Winnipeg R3P 1X9
$887,500Residential- Status:
- Active
- MLS® Num:
- 202608666
- Bedrooms:
- 6
- Bathrooms:
- 4
- Floor Area:
- 2,108 sq. ft.
S/S Thurs, May 21-offers presented Tues, May 26 after 6:00. Completely renovated from top to bottom, this stunning 6 bedroom open-concept residence blends modern luxury with thoughtful design & exceptional functionality. The impressive LR features soaring vaulted ceilings & a sun-filled bay window, creating a bright & inviting atmosphere. The elegant DR is enhanced with a stylish built-in dry bar & floating shelves, while the beautifully updated eat-in kit showcases a lg island breakfast bar, quartz countertops & patio drs that open to an expansive deck—perfect for entertaining. The sunken FR offers a warm & inviting retreat with a cozy gas FP. A main flr br, full 3-piece bath & a well-organized mudroom with custom cabinetry adding everyday convenience & versatility. Upstairs, you’ll find a convenient laundry closet w/washer & dryer, a modern 4-piece bath & a serene primary suite complete with a 3-piece ensuite & a wicc. The fully finished lower level extends the living space with a generous family-sized rec rm, 2 additional brs & a 3-piece bath. Additional highlights include a newer HEF, central A/C, hot water tank, shingles, fascia & soffits—all adding to the appeal of this exceptional turnkey home. 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 May 22, 2026 at 10:35 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