Chris Pennycook
Office 204-989-5000 | chrispennycook@royallepage.ca
My Listings
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201 188 Roslyn Road in Winnipeg: Osborne Village Condominium for sale (1B) : MLS®# 202626341
201 188 Roslyn Road Winnipeg R3L 0G8 
$144,900Condominium- Status:
- Active
- MLS® Num:
- 202626341
- Bedrooms:
- 1
- Bathrooms:
- 1
- Floor Area:
- 742 sq. ft.
S/S now, offers as received. Location, location, location! Freshly updated this year with new paint & flooring, this affordable 1-bedroom condo offers comfortable living in the heart of Osborne Village. The bright, open-concept kitchen, dining & living areas create a welcoming space, with a peninsula breakfast bar providing extra seating. Patio doors open to a west-facing balcony with screens, perfect for enjoying fresh air & relaxing outdoors. A wall of hallway closets offers excellent storage, while the spacious 4-piece bath adds convenience. The bright bedroom features a built-in desk & bookcases, ideal for working from home or creating a cozy reading space. Shared laundry is conveniently located on the same floor. This pet-friendly building offers elevator access & one underground parking stall. Step outside to enjoy the vibrant Osborne Village lifestyle, with popular restaurants, cafés, boutiques & nightlife just moments away. Wellington Crescent, downtown, The Forks & scenic river pathways are also easily accessible. An excellent opportunity for first-time buyers, downsizers or investors looking for affordable living in a walkable, sought-after location! 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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115 Mountbatten Avenue in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202625838
115 Mountbatten Avenue Winnipeg R3P 0P5
$1,249,900Residential- Status:
- Active
- MLS® Num:
- 202625838
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 2,941 sq. ft.
Offers as received. Exceptional opportunity in desirable Tuxedo! This 2 storey family home sits on a gorgeous south-facing 75’ x 130’ lot. The lovely Tyndall stone exterior welcomes you into a home w/numerous updates, including refinished oak hardwoods throughout the main living areas & bedrooms. The bright LR features a wood-burning fp, while the DR overlooks the gorgeous backyard. The inviting FR boasts wall-to-wall windows & charming wainscotting. The kitchen offers abundant maple cabinetry newer high-end S/S appliances including a new Bosch dishwasher (2026), 4-burner gas cooktop & large peninsula w/breakfast bar. A convenient 2-piece bath completes the main floor. Upstairs offers 4 brs, laundry & 3 baths. The secluded primary bedroom features a wall-mounted fireplace, updated 4-piece ensuite & private den/office. 2nd br w/updated 3-piece ensuite. Renovated in 2023, the basement boasts a spacious rec room, custom wet bar, 2nd laundry, 2-piece bath & ample storage. Enjoy the private backyard oasis w/large deck, pergola, hot tub (2023), 2 sheds & mature trees. Heated & insulated AT/2, HEF & C/AIR (2016), metal roof (2013) & updated windows. Walk to Assiniboine Park! 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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361 Christie Road in Winnipeg: South St Vital Residential for sale (2M) : MLS®# 202625874
361 Christie Road Winnipeg R2N 4A5
$825,000Residential- Status:
- Active
- MLS® Num:
- 202625874
Offers presented as received. Fabulous opportunity to build your dream home on this spectacular 1.8-acre riverfront lot on Christie Road! Enjoy beautiful views of the Red River from this private, treed property located inside the floodway. The elevation offers excellent potential for a walkout basement, while the southern exposure provides wonderful natural light and scenic river views. Surrounded by mature trees and nature, this exceptional property offers privacy and a peaceful setting, all within a 25-minute drive of the city centre. A unique opportunity to create your own riverfront retreat! 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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235 Lockwood Street in Winnipeg: River Heights North Residential for sale (1C) : MLS®# 202625305
235 Lockwood Street Winnipeg R3N 1S1
$499,900Residential- Status:
- Active
- MLS® Num:
- 202625305
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 1,518 sq. ft.
Discover this North River Heights gem in a fantastic mid-block location, steps from Carpathia School & TR Hodgson Park! Blending character with modern updates, this one & a half storey home offers over 1500 sq. ft. of living space. Recent improvements include re-stained hardwood floors, fresh paint, pot lighting, newer flooring & an open-concept design. The bright L-shaped living & dining room features large windows & charming cove ceilings. The updated white kitchen offers plenty of cabinetry, a new stainless steel dishwasher (2026) & an opening to the living room, ideal for entertaining. Two main-floor bedrooms & an updated 3-piece bath complete this level. Upstairs, newer flooring compliments two additional spacious bedrooms. The basement is original but offers excellent potential with a large rec room featuring a dry bar, workshop area, laundry & 2-piece bath. Enjoy the immaculate backyard, partially fenced with a covered patio & single detached garage with parking pad. Shingles (2020), HEF (2019) & central air conditioning. A wonderful family home in a sought-after, family-friendly neighbourhood! 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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280 DODDS Road in Headingley: Headingley North Residential for sale (5W) : MLS®# 202624672
280 DODDS Road Headingley R4H 1H5
$224,900Residential- Status:
- Active
- MLS® Num:
- 202624672
Build your dream home on this beautiful 80' x 167' lot on Dodds Road in Headingley! Tree-lined property backing onto an open field, offering a peaceful country setting. Located in the growing community of Headingley, just minutes from Winnipeg’s major amenities. Enjoy low property taxes, local schools, churches, a community centre, great restaurants and plenty of recreational opportunities. Municipal water & sewer. Nearby attractions include Thunder Rapids Fun Park, Nick’s Inn, Headingley Grill, Shelmerdine Garden Centre, Gates on Roblin & Breezy Bend Country Club. The perfect opportunity to enjoy country living with the convenience of city amenities close at hand. Create the home and lifestyle you’ve always envisioned! 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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642 Oxford Street in Winnipeg: River Heights Residential for sale (1D) : MLS®# 202618824
642 Oxford Street Winnipeg R3M 3K1
$449,900Residential- Status:
- Active
- MLS® Num:
- 202618824
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 1,004 sq. ft.
OPEN HOUSE: SATURDAY OCTOBER 31, 2:00-4:00 PM. Step inside this beautifully updated 1000 sq. ft. bungalow, perfectly located just minutes from all the conveniences that make River Heights one of Winnipeg's most desirable neighborhoods. This move in ready home offers numerous upgrades & a bright, functional layout. The spacious living room features beautiful hardwood floors & a large picture window that fills the space with natural light. New bright white kitchen (2026) boasts cabinetry with convenient pull-out organizers, stone countertop plus new appliances! With 3 generously sized brs, including one currently serving as a formal DR, this versatile layout offers the flexibility to adapt to your family’s needs. A renovated 4 piece bathroom completes the main flr. The lower level includes a comfortable recreation room, laundry area & plenty of storage space. Step outside to a family-sized, fully fenced backyard with ample room for children to play, gardening or entertaining. Additional features include new shingles (2025), central air conditioning, HEF & a single detached garage. Excellent location just minutes from Grant Park Shopping Mall, numerous restaurants, schools & Pan Am Pool. 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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14 301 Country Club Boulevard in Winnipeg: Westwood Condominium for sale (5G) : MLS®# 202621358
14 301 Country Club Boulevard Winnipeg R3V 2E4
$939,900Condominium- Status:
- Active
- MLS® Num:
- 202621358
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 2,182 sq. ft.
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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31 Dumbarton Boulevard in Winnipeg: Tuxedo Residential for sale (1E) : MLS®# 202620805
31 Dumbarton Boulevard Winnipeg R3P 2C7
$1,595,000Residential- Status:
- Active
- MLS® Num:
- 202620805
- Bedrooms:
- 3
- Bathrooms:
- 4
- Floor Area:
- 3,363 sq. ft.
S/S now, offers as rec'd. Architectural excellence meets spectacular lakefront living in prestigious Tuxedo. Designed by renowned architect David Penner, this remarkable residence showcases a distinctive layout created to maximize its breathtaking water views. The main level features bedrooms w/private ensuites, while the elevated UL living spaces are surrounded by dramatic floor-to-ceiling windows. The open-concept living & family rooms enjoy panoramic lake views & garden doors opening to a large deck...an exceptional setting for entertaining. A projector & screen add to the impressive entertainment space, complimented by convenient bar-top seating. The formal DR flows into the bright eat-in kitchen featuring white cabinetry, large island, Sub-Zero fridge & expansive wall of windows overlooking the lake. The private primary retreat offers a skylight, WICC & luxurious 5-piece ensuite w/jetted tub. A versatile loft provides an ideal office or studio. The walkout LL includes a spacious rec room, laundry & storage. Additional features include 2 HEF, 2 HWTs, HRV, C/VAC & sump pump. Beautifully landscaped grounds, fenced backyard w/covered patio, AT/3 & direct lake views complete this exceptional 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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497 Brock Street in Winnipeg: River Heights Residential for sale (1C) : MLS®# 202620441
497 Brock Street Winnipeg R3N 0Z2
$589,900Residential- Status:
- Active
- MLS® Num:
- 202620441
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,410 sq. ft.
OPEN HOUSE: SAT. OCT. 31, 12:00-1:30 PM. Price improvement to $589,900! Beautifully updated & lovingly cared for 2-storey w/3 brs & 3 baths in desirable River Heights w/exceptional curb appeal! The exterior features newer siding & a welcoming covered front porch addition (2023) w/modern stacked stone accents, fresh landscaping & a custom foyer w/convenient 2-piece guest bath. Inside, original hardwood floors, character ceilings & abundant natural light add warmth & charm to the LR & DR. The updated kit offers porcelain tile floors, granite counters, soft-close cabinetry w/organizers, tile backsplash, ss appliances & lg peninsula w/breakfast bar seating. Upstairs features 3 bright brs w/hardwoods & an updated 5-piece family bath w/double vanity & tub w/tile surround. The finished bsmt provides a comfortable rec room & updated 3-piece bath. Enjoy the private, fully fenced backyard surrounded by mature trees, featuring a stone patio & firepit, perfect for cooler evenings. HEF, C/AIR & newer HWT. A 22' x 13' DT/1 (2015) provides parking & extra storage. Ideally located steps from school & park. This fabulous home is ready to move into TODAY...don't miss out! 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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53 Harvard Avenue in Winnipeg: Crescentwood Residential for sale (1C) : MLS®# 202618958
53 Harvard Avenue Winnipeg R3M 0J6
$2,975,000Residential- Status:
- Active
- MLS® Num:
- 202618958
- Bedrooms:
- 7
- Bathrooms:
- 6
- Floor Area:
- 5,226 sq. ft.
Grand in scale & rich in character, this impressive 5,000+ sq. ft. home offers 7 brs, 6 baths & exceptional space for both everyday living & entertaining. The incredible FR & expansive kit addition create the ultimate setting for celebrations & making lasting memories. A true culinary masterpiece, this spectacular chef's kit is designed to impress, anchored by an extraordinary 13-foot island with seating for eight...perfect for casual dining. Outfitted with a professional 6-burner gas cooktop & an authentic wood-fired pizza oven, it offers an exceptional cooking experience. Entertain in style with a beautifully appointed wine closet & wet bar, while premium finishes, custom craftsmanship & countless luxury features create a space that is as sophisticated as it is functional. A classic centre hall plan welcomes you with a spac LR featuring hwds & a FP, a stunning DR will comfortably seat 12 guests, den & office. The 2nd level offers 4 brs, including a spacious primary suite with a 3-pce ensuite, while 2 additional brs also enjoy the convenience of their own ensuites.The 3rd level offers a recroom, 3 brs & a 3-piece bath. Shingles 2025. AT/2 + DT/2. 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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1 393 Wellington Crescent in Winnipeg: Crescentwood Condominium for sale (1B) : MLS®# 202618922
1 393 Wellington Crescent Winnipeg R3M 0A1
$499,900Condominium- Status:
- Active
- MLS® Num:
- 202618922
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,981 sq. ft.
Experience carefree riverfront living in this beautifully appointed condominium, ideally located just steps from the scenic Wellington Crescent walking path. A grand foyer welcomes you into the elegant living & dining rooms, where rich crown moulding & a charming wood-burning fireplace create a warm & inviting atmosphere. The bright sunroom features garden doors leading to a private deck overlooking the river...perfect place to relax!. A cozy den offers the perfect space for reading, working from home or quiet relaxation. The spacious kitchen is designed for both style & function w/granite counters, pull-out organizers & adjoining FR for casual everyday living. The private primary suite is a peaceful retreat featuring custom built-ins, a 3-piece ensuite & picturesque views of Munson Park. An elevator provides convenient access to the fully finished LL, offering two more brs, a 4-piece bath, laundry room & large utility room w/abundant storage. Additional features include C/AIR, C/VAC, heated & insulated AT/2 & private storage locker. An exceptional opportunity to enjoy spacious, low-maintenance living in one of Winnipeg's most sought-after riverfront locations. 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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401 290 Waterfront Drive in Winnipeg: Exchange District Condominium for sale (9A) : MLS®# 202611856
401 290 Waterfront Drive Winnipeg R3B 0A6
$479,900Condominium- Status:
- Active
- MLS® Num:
- 202611856
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 1,424 sq. ft.
Executive condo living in the heart of Winnipeg’s vibrant Exchange District! This impressive updated corner unit offers spectacular city & river views along with a bright modern design. Featuring 2 bedrooms, a dedicated office & 2 full baths, the open-concept layout is filled w/natural light from expansive windows & soaring 9’ ceilings. The spacious dining area opens to a wraparound balcony, ideal for relaxing or entertaining. The stylish kit combines function & elegance w/maple cabinetry, granite counters & Frigidaire Professional Series stainless steel appliances. The private primary suite includes its own balcony, large WICC & luxurious 5-piece ensuite w/double sinks, soaker tub & separate shower. A 2nd br & full bath provide excellent flexibility for guests or family. Additional features include in-suite laundry w/extra storage, C/AIR & heated underground parking. Shared centre courtyard. Enjoy a true walkable lifestyle just steps from The Forks, Shaw Park, river pathways, cafés, restaurants, boutiques & Winnipeg’s top arts & entertainment venues. Offering luxury, comfort & unbeatable convenience, this move-in ready condo is the perfect blend of sophisticated urban living & carefree lifestyle. 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 October 30, 2026 at 04:35 PM (UTC)
Featured Listing
14 301 Country Club Boulevard
$939,900
Royal LePage Dynamic Real Estate
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