Chris Pennycook
Office 204-989-5000 | chrispennycook@royallepage.ca
Office Listings
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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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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 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), and 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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in Rosser: RM of Rosser Residential for sale (R11) : MLS®# 202611108
Rosser R0H 1H0
$500,000Residential- Status:
- Active
- MLS® Num:
- 202611108
Own 10 Acres (+/-) for the price of 1 acre in RM of Rosser,near centerport.330 feet frontage on service rd facing perimeter hwy 101 between Inkster Blvd and Rd 63.Property is $50,000.00 per acre,close by centerport.Best investment property as the manitoba government has initiated a study to develop a functonal design for PTH 101. More detailsListed by Jacky Maan of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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12 Public Road in Headingley: Headingley North Residential for sale (5W) : MLS®# 202611301
12 Public Road Headingley R4M 1G9
$26,900Residential- Status:
- Active
- MLS® Num:
- 202611301
Investment Opportunity in Headingley! Located on Farm Road just North of Saskatchewan Ave close to Lyons Street. Zoning is Rural General. Lot size is 107 x 376. No services, Speculation Property. Dirt road access to property ( not an all weather road ). Purchaser may be responsible for GST if applicable. Buy and Hold property. More detailsListed by Tyson Sonnichsen of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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504 Queenston Street in Winnipeg: River Heights Residential for sale (1D) : MLS®# 202610488
504 Queenston Street Winnipeg R3N 0X3
$499,900Residential- Status:
- Active
- MLS® Num:
- 202610488
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 1,014 sq. ft.
SS May 20 @ 5pm. OTP May 25th @ 5pm. Beyond charming & fully remodelled, this River Heights bungalow is all style, substance & serious “move-in-and-do-absolutely-nothing” quality. This 2+ bed, 2 full bath beauty blends character w/ modern updates, creating a home that feels equal parts sophisticated & cozy. Sunlight pours in highlighting hardwood floors, spacious layout & seamless flow made for entertaining, playdates & holiday hosting. The stunning kitchen features quartz counters, S/S appls & thoughtful finishes. Turnkey from top to bottom- HWT '25, AC '21, radon mitigation sys '21, W/D '21, exterior paint '21, custom blinds '23, upgraded electrical panel '21. The fully fin bsmt adds exceptional flexibility w/ a spacious rec rm perfect for movie nights & yoga practices as reprieve-from-the-world. Dedicated laundry rm w/sink, a tucked-away office, & 3-pc bath, extra storage rm, cold storage rm, utility rm with work space completes the bsmt. Outside, the beautifully fenced '21 oasis is hardscaped w/ custom sidewalk & patio stones '21 keeping maintenance low & enjoyment high. The dbl detached gar '21 w/ 220 wiring ready for your own EV charger is the cherry on top of this polished River Heights gem. More detailsListed by Tara Suffield of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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477 Hethrington Avenue in Winnipeg: Lord Roberts Residential for sale (1Aw) : MLS®# 202610471
477 Hethrington Avenue Winnipeg R3L 0V5
$234,500Residential- Status:
- Active
- MLS® Num:
- 202610471
- Bedrooms:
- 1
- Bathrooms:
- 2
- Floor Area:
- 644 sq. ft.
Showings start Wed May 20th, with offers on May 26th. This cozy charmer is located in the trendy, sought after area of South Osborne. This is a perfect home for the first time buyer or use for a cute air B & B. Walking up, you have a covered front porch that leads you into the home. The living room is nice & bright with the newer picture window (2021). The oak kitchen makes good use of the space with a small breakfast nook connecting to the living area. Off to the side is a space that can be used as a small office area, or look at bringing laundry up to the main floor. The back foyer has a 2 pc powder room and access to low maintenance back yard. Upstairs is your loft style bedroom with 4 pce ensuite with claw foot tub. The part basement houses the utilities, washer & dryer and offers some storage. The newer 16 x 22 garage(2010) keeps the car dry from the elements, will provide extra storage or maybe a small workshop space. Updates include: AC 2009, Shingles 2012, front doors 2021, kitchen floor 2025 & exterior paint 2024. This location can't be beat; conveniently placed within walking distance to public transit, shopping, restaurants, cafes & more. Why rent when you can own this adorable home! 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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in Rosser: RM of Rosser Residential for sale (R11) : MLS®# 202611110
Rosser R0H 1H0
$500,000Residential- Status:
- Active
- MLS® Num:
- 202611110
Own 10 Acres (+/-) for the price of 1 acre in RMof Rosser,near centerport,330 feet frontage on service rd facing perimeter hwy 101 between Inkster Blvd and Rd 63.Property is $50,000.00 per acre,close by centerport.Best investment property as the manitoba government has initiated a study to develop a functonal design for OTH 101. More detailsListed by Jacky Maan of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
Data was last updated May 21, 2026 at 06:35 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