Chris Pennycook
Office 204-989-5000 | chrispennycook@royallepage.ca
Office Listings
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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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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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2 Golden Gate Bay in Winnipeg: Silver Heights Residential for sale (5F) : MLS®# 202610448
2 Golden Gate Bay Winnipeg R3J 2Z1
$399,900Residential- Status:
- Active
- MLS® Num:
- 202610448
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,020 sq. ft.
S/S Thurs May 21. OTP May 26 eve. Open house Sun May 24 2:00-3:30. Welcome to this well maintained and beautifully updated home located in the family-friendly neighbourhood of Silver Heights! Owned for the past 9 years, this property has seen many tasteful improvements while maintaining a classic and functional layout. The bright main floor is filled with natural light and features hardwood flooring, warm décor, and a spacious living area perfect for everyday living. Enjoy a formal dining space ideal for hosting family dinners, along with three generous bedrooms and a full 4-piece bathroom on the main level. The fully finished basement offers excellent additional living space, complete with a renovated 4-piece bathroom, a large storage room, and two bonus rooms that could be used as additional bedrooms, home offices, or hobby spaces (windows do not meet current egress code). Outside you’ll love the fully fenced yard, newer deck for summer entertaining, and the convenience of a single detached garage with front drive access. Located close to schools, parks, shopping, and transit—this is a fantastic opportunity to settle into one of Winnipeg’s most desirable neighbourhoods. Book your showing today! More detailsListed by Chad Leigh of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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31 Dumbarton Boulevard in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202610153
31 Dumbarton Boulevard Winnipeg R3P 2C7
$1,700,000Residential- Status:
- Active
- MLS® Num:
- 202610153
- Bedrooms:
- 3
- Bathrooms:
- 4
- Floor Area:
- 3,363 sq. ft.
S/S Thurs. May 21, offers Tues. May 26 after 6 pm. Stunning architectural masterpiece designed by renowned architect David Penner, offering breathtaking lake views & a truly distinctive layout in prestigious Tuxedo. Thoughtfully designed w/main floor bedrooms featuring private ensuites & an elevated UL living space that maximizes the spectacular setting. The open-concept living & family rooms are surrounded by dramatic floor-to-ceiling windows & offer access to a west-facing deck overlooking the lake. A projector & screen create the ultimate entertainment experience, while bar-top seating makes hosting effortless. The formal dining area flows into the bright eat-in island kit featuring white cabinetry, Sub-Zero fridge & a wall of windows capturing stunning water views. A private primary retreat offers a skylight, expansive WICC & 5-piece ensuite w/jetted tub. A loft provides ideal flex space for an office or studio. The walkout LL includes a rec room, laundry & ample storage. Additional features include 2 HEF, 2 HWT, HRV, C/VAC & sump pump. Beautifully landscaped grounds, fenced backyard w/covered patio, AT/3 & direct lake views complete this exceptional property! Steps from 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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170 Dennis Street in Emerson: R17 Residential for sale : MLS®# 202611151
170 Dennis Street Emerson R0A 0L0
$249,900Residential- Status:
- Active
- MLS® Num:
- 202611151
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,761 sq. ft.
Step inside this beautifully renovated & maintained 3 bed +, 2 bath, 1,761 sq. ft. of bright, comfortable living space on a double lot. Designed w/both style & accessibility in mind, including widened doorways, accessible shower in main floor bathroom & a convenient accessibility ramp from the back entry right into the cozy living room. Enjoy the comfort of a modern open layout w/updates throughout! From flooring & fixtures to mechanical systems. Relax & unwind in the living room hot tub w/ ozonator, perfect for year-round enjoyment! Outside, you’ll love the screened porch (20'6" x 8'11"), a double detached garage (22' x 24'), garden shed (12'2" x 12'2") backing onto private treed greenspace. Plenty of space for hobbies, storage & outdoor projects. Practical updates include high-efficiency electric furnace and A/C, hot water tank & sump pump w/ backwater valve for peace of mind. Elementary School, playground, grocery, public pool, Golf course & other amenities nearby. Located in the quiet community of Emerson just minutes from the U.S. border just an hour from WPG. Move-in ready combining modern updates, thoughtful design & small-town charm! Pride of long term ownership! Book Now & Just turn the key! More detailsListed by Cheryl Demarcke and Jessica Hancock of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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372 Waverley Street in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202610687
372 Waverley Street Winnipeg R3M 3L3
$539,900Residential- Status:
- Active
- MLS® Num:
- 202610687
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,665 sq. ft.
Showings start May 20; Offers reviewed May 27. Welcome to this timeless character home in one of Winnipeg’s most sought-after neighbourhoods known for its tree-lined streets & strong sense of community. Lovingly maintained by the same family for over 30 years, this home blends original charm with thoughtful updates. Classic features like hardwood floors, arched openings, & brick fireplace create warmth & character, while the updated kitchen offers modern functionality. The main living spaces flanked by large windows are bright, inviting, & designed for both everyday living & entertaining, with a sunroom that quickly becomes a favourite place to unwind. Upstairs features three bedrooms, including a spacious primary with two walk-in closets. The recently updated four-piece bathroom adds a fresh, modern touch. A finished basement with an additional bathroom provides flexible living space for growing families, guests, or home office. Step outside to a fully fenced backyard complete with a deck & patio, perfect for summer evenings filled with entertaining & letting kids play freely. Complete with a newer built double car garage, this home offers all of today's modern conveniences while embracing its charm. More detailsListed by Monica Manaigre of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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446 Yale Avenue W in Winnipeg: West Transcona Residential for sale (3L) : MLS®# 202610452
446 Yale Avenue W Winnipeg R2C 1V3
$399,900Residential- Status:
- Active
- MLS® Num:
- 202610452
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 963 sq. ft.
S/S May 20. OTP May 25 eve. Open house Sunday May 24 2:00-3:30. Welcome to this beautifully renovated and meticulously maintained home in the heart of Transcona—perfect for growing families! Step inside and enjoy a bright, contemporary layout featuring a stunning new kitchen with updated finishes and plenty of cabinet space, ideal for everyday living and entertaining. The main level offers three comfortable bedrooms and a fully renovated bathroom, providing a fresh and stylish feel throughout. Downstairs, the fully finished basement expands your living space with a spacious rec room, perfect for movie nights or a kids’ play area, along with a separate laundry room, storage room, and additional space to keep everything organized. Outside, you’ll love the fully fenced yard—great for kids, pets, and summer gatherings—plus the convenience of a single detached garage. This move-in ready home offers excellent value in a family-friendly neighbourhood close to schools, parks, shopping, and all amenities. Don’t miss your chance to own this updated Transcona gem—book your showing today! More detailsListed by Chad Leigh of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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394 Thompson Drive in Winnipeg: Grace Hospital Residential for sale (5F) : MLS®# 202610427
394 Thompson Drive Winnipeg R3J 3E6
$524,900Residential- Status:
- Active
- MLS® Num:
- 202610427
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 2,472 sq. ft.
S/S Thurs. May 21, offers Tues. May 26 after 6 pm. This beautifully updated bungalow features a 2 story addition (1985). The bright & inviting living & dining room combination showcases warm hwds & creates the perfect setting for both everyday living & entertaining. The spacious eat-in kit is designed for convenience, featuring an abundance of cabinetry with plenty of pull-outs, an attached table for casual dining. The main floor offers 2 comfortable brs a convenient 2-pce & 3-pce bathroom, a functional mudroom with access to the attached single garage. A truly spectacular FR addition serves as the heart of the home, highlighted by a stunning floor-to-ceiling Tyndall stone wood-burning fireplace, a cozy office nook, a wet bar, and patio doors leading to a fabulous sunroom filled with natural light. The UL is dedicated to a private primary bedroom retreat featuring a vaulted ceiling, WICC & a spacious 4-piece ensuite. The basement expands the living space even further with a large rec room complete with a wet bar, an additional bedroom ideal for guests, space for a home office. Outside, the partially fenced yard offers built-in seating & a patio area, creating the perfect outdoor space for relaxing. 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 21, 2026 at 02:35 AM (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