Chris Pennycook

Office 204-989-5000 | chrispennycook@royallepage.ca

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I have sold a property at 5 738 Dorchester AVE in Winnipeg

I have sold a property at 5 738 Dorchester AVE in Winnipeg on Jun 5, 2026. See details here

This spacious 2-bedroom condo beautifully blends timeless character with modern updates throughout. The inviting living room showcases newer flooring & an original ornamental fireplace with elegant bronze plate detailing, creating a warm & distinctive focal point. It flows effortlessly into a stunning four-season sunroom, where exposed brick & expansive windows bathe the space in natural light—an ideal retreat for morning coffee or evening relaxation year-round. A generous formal dining room features a classic built-in buffet, adding both charm & practical storage, making it perfect for hosting gatherings. The renovated kitchen is as stylish as it is functional, offering an abundance of cabinetry, butcher block countertops, stainless steel appliances & a convenient pantry to keep everything organized. With two separate entranceways providing flexibility & privacy, plus easy access to a dedicated outdoor parking spot. Excellent location just steps from Wellington Crescent’s scenic walking path, as well as numerous restaurants, shopping & everyday amenities.

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I have sold a property at 74 Bethune WAY in Winnipeg

I have sold a property at 74 Bethune WAY in Winnipeg on Jun 4, 2026. See details here

S/S Thurs. May 28, offers Tues. Jun 2 after 6 pm. Sun-filled bungalow showcasing soaring vaulted ceilings & stylish luxury vinyl plank floors throughout the main living area. A stunning 2023 kitchen renovation by Gateway Kitchen & Bath offers soft-close cabinetry w/multiple organizers, quartz counters, walnut floating shelves, tile backsplash & ss appliances including a gas cooktop w/striking custom hood fan & tile. The breakfast island includes an undermount sink & added storage, while the built-in banquette w/more storage comfortably seats 6. The LR opens to the deck & beautifully landscaped backyard. A spacious primary suite includes a WICC & 4-piece ensuite w/heated tile flooring. 2 additional bedrooms, full bath & convenient laundry complete the main level. The fully finished basement offers a huge rec room & games area w/gas fireplace, wet bar & bonus office or hobby space, plus a guest bedroom & updated 3-piece bath. You will love the very pretty south-facing fenced backyard w/deck, BBQ gas hookup, fire pit patio, mature trees & low-maintenance landscaping. The front deck is perfect for your morning coffee. C/AIR, C/VAC, AT/2. Ideally located minutes from St. Vital Park & everyday amenities.

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I have sold a property at 356 Willow Creek RD in Winnipeg

I have sold a property at 356 Willow Creek RD in Winnipeg on Jun 4, 2026. See details here

S/S Thurs. May 28, offers presented Tues. June 2 after 6 pm. Spectacular bungalow offering over 4,000 sq. ft. of incredible living space with exceptional upgrades throughout. Every detail and finish has been meticulously designed, featuring an open-concept layout, soaring ceilings, rich hardwood floors & a stunning walnut feature wall with fireplace. Expansive floor-to-ceiling windows showcase breathtaking lake views & fill the home with natural light. The chef-inspired island kitchen boasts custom walnut cabinetry, high-end JennAir appliances & a convenient butler’s pantry. Sunken DR features patio doors leading to a spacious deck overlooking the beautifully landscaped yard & lake. The private primary retreat offers a wall of windows, direct deck access & a luxurious spa-inspired ensuite with heated tile flrs. Two additional main flr brs share a well-appointed bathroom, while the main level also includes a mudroom & laundry area. The fabulous lower level is designed for entertaining & relaxation, complete with a large rec room, games area, wet bar, one-of-a-kind gym with shower, an additional bedroom, and a 4-piece bath. Completing this exceptional property is a spacious screened-in summer sanctuary.

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I have sold a property at 1001 Jessie AVE in Winnipeg

I have sold a property at 1001 Jessie AVE in Winnipeg on May 26, 2026. See details here

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.

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I have sold a property at 128 McCrindle BAY in Winnipeg

I have sold a property at 128 McCrindle BAY in Winnipeg on May 25, 2026. See details here

Fabulous custom-built 2-storey home in Ridgewood South offers bright, spacious living with a modern open-concept design & a stunning backyard oasis with an amazing surprise! Built in 2023, the main floor features wide plank flooring, expansive windows, built-in great room storage & patio doors leading to a large deck w/glass panels. The chef’s kitchen boasts ss appliances, quartz counters, soft-close cabinetry & an updated island w/breakfast bar & double sink. A convenient pantry w/pass-through to the custom mudroom adds style & function. Upstairs offers a loft, great for a reading nook or office. 3 bedrooms in total, family bath & laundry. The private primary suite includes a walk-in clothes closet and 4-piece ensuite. The finished basement features a spacious rec room, 4-piece bath & guest bedroom, currently used as a gym. The stunning backyard was designed by Gellers & highlights include a 20' x 12' inground fiberglass pool w/resort entry, insulated pool shed, covered outdoor kitchen w/bar seating, dining patio, garden beds & maintenance-free landscaping...ready for summer! HEF, C/AIR, HRV, sump pump & o/s AT/2. Minutes to shopping & the perimeter.

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New property listed in The Oaks, 5W

I have listed a new property at 55 70 Oak Forest CRES in Winnipeg. See details here

S/S Thurs. June 4, offers presented Tues. June 9 after 6 pm. Experience refined living in this immaculate 1,290 sq. ft. bungalow, thoughtfully designed with modern elegance and exceptional attention to detail. Offering 3 bedrooms and 3 baths, this beautifull home showcases custom silhouette blinds, expansive windows, designer lighting & a bright open-concept layout ideal for both everyday living & entertaining. The inviting GR flows seamlessly into the dining area w/direct access to the professionally landscaped backyard & deck...perfect for summer gatherings. The stunning kit is a true centerpiece, featuring crisp white cabinetry, ss appliances & waterfall island w/breakfast bar seating. The private primary retreat boasts a WICC & luxurious 3-piece ensuite. A second bedroom or home office, full bath & convenient main floor laundry complete the main level. The fully finished LL offers a spacious rec room, guest bedroom, 3-piece bath & option to create a fourth br if desired. Built on piles & complimented by a double attached garage, this exceptional home combines style, comfort & quality in every detail. Located in Country Estates in The Oaks, minutes from amenities & easy access to walking trails.

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New property listed in River Heights North, 1C

I have listed a new property at 1324 Wellington CRES in Winnipeg. See details here

S/S Thurs, June 4-offers presented Tues, June 9 after 6:00 p.m. Ideally located on prestigious Wellington Crescent & just steps from the beautiful tree-lined walking path, this exceptional residence offers a prime setting in one of the city's most sought-after locations. Stunning architectural design & impeccable craftsmanship are showcased throughout, creating a refined blend of luxury & sophistication. The elegant LR is highlighted by a dramatic floor-to-ceiling bay window, custom art niches & a charming wood-burning FP. Inviting DR with patio drs opens seamlessly to the fabulous fenced backyard with tiered deck, creating the perfect setting for relaxing & entertaining. The well-appointed kitchen features a Bosch cooktop, 4-burner gas oven, pull-out organizers & an abundance of cabinetry designed for both style & functionality. Upstairs, a mezzanine office/reading nook provides a casual retreat. The spacious primary bedroom features a cozy gas fireplace, dual closets & direct access to a luxurious 5-piece bath, offering a peaceful haven for rest and relaxation. Bright fully finished lower level includes a generous recroom with gas FP, an additional guest br, 3-piece bath & convenient laundry closet.

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New property listed in River Heights North, 1C

I have listed a new property at 243 Niagara ST in Winnipeg. See details here

S/S Thurs. June 4, offers presented Tues. June 9 after 6 :00 pm. Charming bungalow in the heart of North River Heights offering 964 sq ft of comfortable living space with excellent basement development potential featuring high ceilings & large windows. Original hardwood floors flow throughout, complemented by a welcoming living room with wood-burning fireplace & spacious formal dining room. Bright white kitchen showcases soft-close cabinetry plus newer oven & refrigerator (2022). Both bedrooms overlook the expansive backyard, while the freshly painted interior (2026) adds a fresh modern touch. Outstanding curb appeal with mature trees, tiered deck with new railing (2021), newer chain link fence (2025) & large concrete patio create the perfect outdoor retreat. Additional upgrades include a new boiler/water heater (2020), new eavestroughs (2021), replaced shingles south & west (2021) offering added value & peace of mind. Ideally located within walking distance to Academy Road’s shops, cafes & restaurants

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New property listed in Tuxedo, 1E

I have listed a new property at 27 Stanford BAY in Winnipeg. See details here

S/S Thurs, June 4-offers presented Tues, June 9 after 6:00 p.m. Immaculate two-storey family home in the heart of the distinguished Tuxedo neighbourhood. A lovely foyer welcomes you with a striking stone feature wall, leading into an elegant living room with a double-sided wood-burning fireplace & stunning tile flooring. The dining room features a built-in buffet with accent lighting & a bay window overlooking the beautifully landscaped backyard. The eat-in kitchen offers cabinets with pullouts, a central island with granite countertops & a casual dining area. A sunken family room with a wood-burning fireplace, along with a bright sunroom featuring heated flooring & garden doors, provides access to an entertainer’s dream backyard complete with an amazing in-ground pool & gazebo. Main floor also includes a convenient laundry room & 2-piece bath. Upstairs offers four bedrooms (one currently used as an office) & a 4-piece bath, while the spacious primary suite features a 4-piece ensuite with heated floors & ample closet space. The fully finished lower level includes a rec room, additional bedroom & 3-piece bath. Additional highlights include shingles (2025), central vacuum & an attached double garage.

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I have sold a property at 182 Lindsay ST in Winnipeg

I have sold a property at 182 Lindsay ST in Winnipeg on May 26, 2026. See details here

Brand new executive custom build in sought-after North River Heights, offering exceptional design, premium finishes & striking curb appeal with acrylic stucco, contemporary masonry & o/s stacked windows. Constructed on a piled foundation, this home features commercial-grade LVP flooring, expansive windows & impressive 9 & 10-foot ceilings across the main & upper levels. A spacious foyer leads into an elegant dining area & a show-stopping kitchen w/illuminated waterfall island, quartz counters, soft-close push cabinetry & LG appliances. The sunken LR provides a warm gathering space w/access to the east-facing deck, while a convenient guest bath completes the main floor. Upstairs, you’ll find 3 brs including a stunning primary retreat w/vaulted cathedral ceiling, spa-inspired 5-piece ensuite w/heated flrs, wet room & a custom WICC. UL laundry & a private office offer added flexibility. The lower level is designed w/potential for a secondary suite, featuring a separate entrance, wet bar, custom millwork, bedroom, laundry & independent mechanical systems. Smart home integration & heated double garage pre-wired for EV charger complete this stunning property.

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New property listed in Exchange District, 9A

I have listed a new property at 401 290 Waterfront DR in Winnipeg. See details here

S/S Sat. May 30, offers presented as rec'd. 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 brs, 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 ss 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. 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.

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New property listed in Bridgwater Trails, 1R

I have listed a new property at 356 Willow Creek RD in Winnipeg. See details here

S/S Thurs. May 28, offers presented Tues. June 2 after 6 pm. Spectacular bungalow offering over 4,000 sq. ft. of incredible living space with exceptional upgrades throughout. Every detail and finish has been meticulously designed, featuring an open-concept layout, soaring ceilings, rich hardwood floors & a stunning walnut feature wall with fireplace. Expansive floor-to-ceiling windows showcase breathtaking lake views & fill the home with natural light. The chef-inspired island kitchen boasts custom walnut cabinetry, high-end JennAir appliances & a convenient butler’s pantry. Sunken DR features patio doors leading to a spacious deck overlooking the beautifully landscaped yard & lake. The private primary retreat offers a wall of windows, direct deck access & a luxurious spa-inspired ensuite with heated tile flrs. Two additional main flr brs share a well-appointed bathroom, while the main level also includes a mudroom & laundry area. The fabulous lower level is designed for entertaining & relaxation, complete with a large rec room, games area, wet bar, one-of-a-kind gym with shower, an additional bedroom, and a 4-piece bath. Completing this exceptional property is a spacious screened-in summer sanctuary.

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New property listed in East Elmwood, 3B

I have listed a new property at 1056 McCalman AVE in Winnipeg. See details here

S/S Thurs. May 28, offers Tues. June 2 after 6:00 pm. Great starter, investment or retirement home on a quiet bay in East Elmwood. Freshly painted with updated flooring, this move-in-ready bungalow offers a bright eat-in kitchen with stainless appliances and three well-sized bedrooms on the main level, each with carpeting and abundant natural light. A large hallway storage area with a barn door adds charm & functionality. The partially finished basement is ready for your finishing touches & includes a rec room, workshop, office/gym space & a convenient combination 4-piece bath with laundry & storage. The fenced backyard provides plenty of room to relax with your morning coffee or evening cocktail plus easy entertaining for family & friends on the spacious deck. Parking for 2+ vehicles. Central air conditioning ensures year-round comfort. Set in a great location overlooking greenspace & within walking distance to public transit, parks & schools. Minutes to shopping, restaurants & recreation. You don't want to miss this fantastic opportunity...book your showing today!

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New property listed in St Vital, 2C

I have listed a new property at 74 Bethune WAY in Winnipeg. See details here

S/S Thurs. May 28, offers Tues. Jun 2 after 6 pm. Sun-filled bungalow showcasing soaring vaulted ceilings & stylish luxury vinyl plank floors throughout the main living area. A stunning 2023 kitchen renovation by Gateway Kitchen & Bath offers soft-close cabinetry w/multiple organizers, quartz counters, walnut floating shelves, tile backsplash & ss appliances including a gas cooktop w/striking custom hood fan & tile. The breakfast island includes an undermount sink & added storage, while the built-in banquette w/more storage comfortably seats 6. The LR opens to the deck & beautifully landscaped backyard. A spacious primary suite includes a WICC & 4-piece ensuite w/heated tile flooring. 2 additional bedrooms, full bath & convenient laundry complete the main level. The fully finished basement offers a huge rec room & games area w/gas fireplace, wet bar & bonus office or hobby space, plus a guest bedroom & updated 3-piece bath. You will love the very pretty south-facing fenced backyard w/deck, BBQ gas hookup, fire pit patio, mature trees & low-maintenance landscaping. The front deck is perfect for your morning coffee. C/AIR, C/VAC, AT/2. Ideally located minutes from St. Vital Park & everyday amenities.

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New property listed in East Kildonan, 3E

I have listed a new property at 31 Werrell WAY in Winnipeg. See details here

S/S Thurs. May 28, offers presented Tues. June 2 after 6 pm. Immaculate & exceptionally maintained bungalow that has been fully updated and is completely move-in ready. Bright open-concept living & dining areas feature a newer o/s picture window that fills the home w/natural light. The expansive kitchen offers white soft-close cabinetry, ss appliances, pantry storage & peninsula w/breakfast bar seating perfect for casual dining & entertaining. The spacious primary bedroom includes a convenient 2-piece ensuite, while two additional bedrooms & a full bath complete the main floor. The fully finished lower level continues the bright & inviting feel with a large rec room, guest bedroom/gym, updated 3-piece bath & laundry/storage area. Enjoy the large partially fenced backyard with plenty of room to relax or entertain. An o/s DT/1 & extra-long front driveway provide excellent parking & storage options. Numerous upgrades throughout include windows, lighting, 200-amp electrical panel, C/AIR (2025), HEF & HWT (2018) & shingles (2015). Walking distance to Siddall/Werrell Park and close to all amenities, this beautifully updated home offers outstanding value with nothing left to do but move in and enjoy.

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Open House. Open House on Sunday, May 24, 2026 1:00PM - 3:00PM
Crescentwood Gem!
Updated 3-bedroom-3 bath, 1504 sf home on quiet street near Corydon. Hardwoods, stylish island kit, finished basement, fenced yard & newer garage. Heated sunroom. Move-in

Please visit our Open House at 1001 Jessie AVE in Winnipeg. See details here

Open House on Sunday, May 24, 2026 1:00PM - 3:00PM Crescentwood Gem! Updated 3-bedroom-3 bath, 1504 sf home on quiet street near Corydon. Hardwoods, stylish island kit, finished basement, fenced yard & newer garage. Heated sunroom. Move-in ready close to parks, schools & dining. Anna 204-781-4156

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.

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New property listed in St Charles, 5G

I have listed a new property at 14 301 Country Club BLVD in Winnipeg. See details here

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.

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I have sold a property at 1018 Corydon AVE in Winnipeg

I have sold a property at 1018 Corydon AVE in Winnipeg on May 21, 2026. See details here

Rarely available, this exceptionally well-maintained duplex offers a standout opportunity to own in the heart of the vibrant & highly sought-after Corydon neighbourhood. Thoughtfully cared for & full of charm, both suites showcase bright, spacious living & dining areas, complemented by 2 generously sized bedrooms, while the upper unit also features a versatile office—perfect for working from home. Each suite includes a full 4-piece bath & a welcoming eat-in kitchen complete with appliances, ideal for comfortable everyday living. Tenants will appreciate the convenience of private access to the shared bsmt laundry rm, outfitted with a washer, dryer along with the added bonus of a gym plus storage lockers. Outdoors, enjoy a beautifully maintained patio space with a covered gazebo—perfect for relaxing or entertaining—plus the practicality of a dble garage & an expansive additional parking pad. Set in an unbeatable location just steps from trendy shops, popular restaurants & convenient transit routes, this property blends lifestyle & investment appeal seamlessly, making it an exceptional choice for both investors & owner-occupiers alike.

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New property listed in Crescentwood, 1Bw

I have listed a new property at 1001 Jessie AVE in Winnipeg. See details here

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.

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New property listed in Grace Hospital, 5F

I have listed a new property at 394 Thompson DR in Winnipeg. See details here

S/S Thurs. May 21, offers Tues. May 26 after 6 pm. This beautifully updated bungalow offers an incredible addition. 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.

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