Chris Pennycook

I have listed a new property at 266 ANTONIO AVE in St Francois Xavier. See details here

S/S Wed. Oct. 7, offers as rec'd. Experience exceptional country living in this luxurious property offering 5,000+ sq ft of beautifully finished living space & 6 bedrooms! Designed for both grand-scale entertaining & everyday comfort, the dramatic GR features a 23' vaulted beam ceiling, designer lighting, southern exposure, floor-to-ceiling custom striking Napoleon wood-burning fireplace w/copper, wood & slate accents. Gorgeous bamboo engineered hardwoods & custom teak cabinetry flow throughout. The gourmet kitchen boasts a large waterfall quartz island & Bosch appliances, while the elegant DR features a built-in dry bar, custom accent wall & floor-to-ceiling south-facing windows. A spectacular 4-season sunroom offers wall-to-wall windows, hot tub & garden door to the deck. Custom main-floor mudroom/laundry. Primary retreat w/acoustic feature wall, ethanol fireplace & private screened sunroom. 5-pce spa ensuite w/cast-iron soaker tub, steam shower & double vanity. Upper loft, 2 additional bedrooms & bath. Entertainer’s LL includes rec room/wet bar, theatre, gym, 3 brs & bath. 4-zone sound, o/s AT/3 roughed-in for in-floor heat, 400-amp service, 2 furnaces, 2 HWTs, HRV & C/VAC. Built on timber piles.

I have listed a new property at 517 Weedon ST in Winnipeg. See details here

S/S Mon. Oct. 5, offers presented as rec'd. Great opportunity to bring your vision to this solid 3+ bedroom bungalow on a nice street in East Kildonan! Bright and spacious, this home offers good bones, a functional layout & plenty of potential to create a wonderful family home. The main floor features an L-shaped living & dining room with a wood-burning fireplace, plus an eat-in kitchen with stainless steel appliances. Three bedrooms & a full bath complete the main level, including the primary bedroom with 2-piece ensuite & a bedroom with patio doors leading to the 3-season sunroom. The finished basement offers excellent potential for additional living space, featuring a rec room with wood-burning fireplace, wet bar, 3-piece bath, sauna & possible 4th bedroom. Outside, enjoy a fenced backyard with patio & storage shed, plus a double detached garage. Ideally located close to schools, shopping, parks & transit. A fantastic opportunity for buyers looking for a home they can personalize & make their own!

I have listed a new property at 280 DODDS RD in Headingley. See details here

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!

I have listed a new property at 58 151 Greenway CRES E in Winnipeg. See details here

S/S Friday Sept. 25, offers Thurs. Oct. 1 afternoon. Plenty of potential to modernize & make this spacious townhouse your own! Tucked away on a quiet Crescent, this pet-friendly home is steps from shopping, transit & everyday amenities, while enjoying a peaceful setting away from traffic noise. The inviting sunken living room features a charming vaulted wood ceiling & gas fireplace, creating a warm focal point. The dining room overlooks the living room...perfect for entertaining. The kitchen offers newer appliances & opens to a generous sized family room/den. Patio doors lead to the deck overlooking green space & picturesque Sturgeon Creek. A convenient 2-piece bath completes the main level. Upstairs offers 3 bedrooms & a full bath with dual access. Two bedrooms enjoy lovely creek views, while the spacious primary features a walk-in closet. The full basement provides excellent storage & laundry space, with plenty of opportunity to develop additional multipurpose living areas. Outdoor parking right in front of the unit. A great opportunity to add your personal style & create a home that truly suits your lifestyle!

I have listed a new property at 347 Oak ST in Winnipeg. See details here

S/S Wed. Sept.23, offers Tues. Sept.29 evening. Absolutely stunning 2022 renovation blends timeless River Heights character w/sophisticated modern design. Superior craftsmanship & thoughtful details are showcased throughout...wide-plank white oak hdwds & custom cabinetry by Two30Nine. The bright LR/DR combo features a cove ceiling, ornamental fp & built-in banquet seating. The gourmet kit is beautifully appointed w/quartz counters, soft-close cabinets w/organizers, ss appliances, farm sink, herb wall & an impressive 9' island w/seating & 2nd dishwasher. A custom mudroom keeps family life organized, while the sun-filled FR offers wall-to-wall wdws & pocket doors to a private office/homework space. UL has 4 brs, including a primary retreat w/custom built-ins & spa-like ensuite w/heated flrs, skylight & wet room w/soaker tub. The 5-piece family bath features double vanity, water closet & laundry hookups. Finished bsmt offers a great kids' hangout, 5th br, 3-piece bath & storage/laundry. HEF, C/AIR, sump pump & updated windows. Outside, modern stucco compliments the character exterior, while a clover front yard, maintenance-free fenced backyard w/turf & side patio create easy outdoor living. Heated DT/2.

I have listed a new property at 193 Robindale RD in Winnipeg. See details here

S/S Thurs. Sept. 24, offers presented Wed. Sept.30 after 1 pm. Rare opportunity to own a true mid-century Charleswood original! Architecturally designed by its original owner, this distinctive 1978 split-level is beautifully positioned on an expansive pie-shaped lot, nestled among mature trees w/a private, park-like setting. Built on piles, the property offers an incredible combination of land, space & timeless mid-century character. Inside, vaulted wood ceilings, o/s windows & a sunken LR showcase the home’s original architectural design. The formal DR overlooks the spectacular backyard, while the eat-in kit features patio doors to a deck. The UL offers 4 bedrooms, including a spacious primary w/WICC & 3-piece ensuite. Designed w/entertaining in mind, the LL features rich wood accents, stone-facing wood-burning fp, guest bedroom, 2-piece bath & an extra large laundry room w/wall-to-wall storage & cedar closet. 2 furnaces, 2 C/AIR units & humidifier. Inviting stone exterior w/wood accents, long paver stone driveway & AT/2. Steps to Roblin Park Community Centre. A truly special property w/incredible potential to restore, renovate & make your own! Some interior photos have been AI enhanced.

I have listed a new property at 259 Scotia ST in Winnipeg. See details here

S/S Wed. Sept.23, offers Mon. Sept. 28 evening. Rare Red River setting! Tucked away on a beautiful river lot, this 1½-storey home offers a unique cottage-like feel w/mature trees, privacy & direct access to the river. The main floor features hardwood flrs throughout the formal living & dining rooms. The LR offers a cove ceiling, electric fp & a large window overlooking the inviting 4-season sunroom, highlighted by a vaulted ceiling & wall-to-wall windows w/river views & access to the yard. The formal DR has double French doors & flows seamlessly into the kit...perfect for entertaining. Updated in 2018, the kitchen features granite counters, soft-close cabinetry w/organizers & ss appliances. Upstairs are 3 bright bedrooms & an updated 4-piece bath. The bsmt offers a rec room w/newer carpeting & wall-to-wall display/storage cabinetry, plus a 3-piece bath, laundry & ample storage. Outside, enjoy the private, maturely treed yard, river access, newer durable rubber paving & a double detached heated/insulated garage w/220-amp panel. Shingles & HEF replaced in approx. 2020. Newer sump pump. Quiet, desirable neighbourhood close to schools. Minutes to Kildonan Park. A truly special riverfront opportunity!

I have listed a new property at 6 Oakdale DR in Winnipeg. See details here

S/S Thurs. Sept. 24, offers Wed. Sept. 30 evening. Absolutely stunning custom 2-storey tucked away on a quiet street! Impressive curb appeal w/extensive exterior updates (2025/26), including flat roof replacement, cedar shake exterior & updated upper deck w/sleek black railing. Grand foyer w/direct views of the backyard. Spectacular LR boasts 16’ ceilings, wall-to-wall wdws & floor-to-ceiling Tyndall stone gas fp. Dedicated gym (2024). Elegant DR seats 8–10. FR features heated flrs, shiplap feature wall & wood-burning fp. Expansive gourmet eat-in kit offers heated flrs, soft-close cabinets, quartz counters, high-end S/S appliances, breakfast bar, large island & access to the deck. The 2025 sunroom addition has a tray ceiling, wall-to-wall windows & garden door to the deck. Private office w/custom built-ins. UL offers 4 brs. Primary retreat w/garden door to west-facing deck, WICC, laundry & 4-piece ensuite w/heated flrs. 2 brs offer upper deck access. Updated 4-piece bath (2026). Finished LL includes freshly painted rec room, guest/teen br & 3-piece bath. West-facing fenced backyard oasis w/mature trees, deck & paver patio. Circular paver drive, heated AT/2. HEF, HRV & C/AIR. Exceptional luxury living!

I have listed a new property at 282 Cathcart ST in Winnipeg. See details here

S/S Thurs. Sept. 17, offers Tues. Sept. 22 after 6 pm. Updated Charleswood bungalow offering great curb appeal, a spacious yard & a prime location! The bright main floor features expansive windows that fills the spaces w/natural light. The fully renovated kitchen (2024) offers stainless steel appliances, soft-close cabinetry, quartz countertops & a peninsula for added prep space. The dining area includes a portable island, ideal for small appliances & extra storage. A 2nd entry provides convenient access to the fenced dog run. The primary bedroom, 2nd bedroom & nicely updated 4-piece bath (2025) complete the main level. The partially finished basement is wired & drywalled, offering a large rec room & laundry room ready for your finishing touches. Outside, enjoy a west facing backyard w/mature trees, new fencing (2023), patio & large storage shed for tools & lawn care maintenance. The inviting exterior features cedar shakes, wood siding accents & a vaulted-roof carport. Triple-pane main-floor windows (2022). C/AIR. Steps from Assiniboine Park & Forest, close to schools, shopping & restaurants. A fantastic starter, investment or retirement opportunity!

I have listed a new property at 642 Oxford ST in Winnipeg. See details here

SS Sept 9th. Offers Sept 15th after 6pm. 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 bedrooms, including one currently serving as a formal dining room, 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.

I have listed a new property at 547 Renfrew ST in Winnipeg. See details here

S/S Thurs. Sept. 10, offers Tues. Sept. 15 after 6 pm. Beautifully updated and modern bungalow in desirable River Heights! The bright main floor features hardwood floors, cove ceilings and large windows for natural light. The updated kitchen overlooks the LR & offers soft-close cabinetry, granite counters, newer stove & panel dishwasher, plus generous counter space. Two main-floor bedrooms feature hardwood floors & excellent closet space, including a large wall-to-wall wardrobe. An updated 4-piece bath completes the main level. The finished basement offers a spacious rec room, two potential bedrooms & an updated 3-piece split bath. A generous laundry/utility room provides ample storage & cedar closet. Step outside to a beautifully landscaped, low-maintenance park like backyard designed for relaxation, featuring a deck, pergola, boardwalk, firepit patio w/wood storage & perennial gardens. The o/s DT/2 includes a heated 16' x 8' workshop/craft room (2020). Numerous updates include windows (2021), C/AIR (2020), HEF (2021) & roof shingles (2016). Fantastic curb appeal & ideally located steps from schools, parks & everyday conveniences. A wonderful starter, family or retirement home!

I have listed a new property at 2427 Assiniboine CRES in Winnipeg. See details here

S/S Thurs. Sept. 10, offers Tues. Sept. 15 at 6 pm. Meticulously maintained 1493 sq ft bungalow with fabulous living space. The spacious LR is filled with natural light from numerous windows, including a lovely corner window & features an impressive floor-to-ceiling brick-front gas FP that creates a warm, welcoming focal point. The DR offers beautiful hwds & flows seamlessly into the updated kit. The kit is stylish & functional, featuring abundant cabinetry w/pull-outs, quartz counters & appliances. The PB offers dble closets w/organizers, while the 2nd br features access to the lovely side patio. This charming outdoor space, finished with interlocking brick, is a relaxing spot to enjoy your morning coffee. The bsmt provides an incredible extension of the home’s living space, with an amazing graffiti-art feature wall highlighting the way down to a huge rec room complete with gas FP & wet bar—perfect for entertaining. The bsmt also offers ample storage, 3 pce bath & a flexible br/office w/closet space. 2 staircases provide convenient access to the bsmt. Laundry rm w/appliances. Step outside to enjoy the beautiful backyard featuring a deck w/pergola & plenty of space to entertain. HEF, C/air & Dt/2.

I have listed a new property at 367 RIVER TRAIL DR in West St Paul. See details here

S/S Sept. 9, Offers Reviewed following the Open House. OH SUN. SEPT. 13, 1-3 PM. Welcome home to this beautifully maintained custom-built two-storey w/stylish modern design. Built in 2019 & located in a quiet, family-friendly West St. Paul community. This home offers wonderful curb appeal w/concrete front drive & lovely landscaping. Inside, the bright open-concept layout is filled w/natural light from expansive windows. The welcoming GR features a stacked stone fireplace wall...perfect for cozy family evenings. The dining area opens through patio doors to the deck & sunny west-facing backyard, creating an ideal space for summer barbecues & entertaining. The kit features quartz counters, ss appliances, a walk-in corner pantry & island w/breakfast bar. Upstairs, enjoy a versatile loft for movie nights or a kids' play area, plus 3 spacious brs. The primary retreat offers backyard views, a WICC & 4-piece ensuite. UL laundry adds everyday convenience. The finished bsmt provides even more room for family & guests w/a large rec room, bedroom & full bath. Outside, the fully fenced yard includes a gazebo, shed & play structure. HEF, HRV, sump pump, O/S AT/2. Close proximity to schools, shopping & restaurants.

I have listed a new property at 796 Elmhurst RD in Winnipeg. See details here

S/S Sept.10, offers Wed. Sept.16. OH SAT. SEPT. 12 & SUN. SEPT. 13, 1-3 PM. Completely renovated from top to bottom in 2026, this STUNNING Charleswood two-storey offers exceptional style, warmth & modern family living! A grand double-door entry welcomes you inside, where beautiful vaulted ceilings & expansive windows create a bright, inviting atmosphere. The gorgeous galley-style kit features a waterfall quartz counter, ss appliances, soft-close cabinetry w/organizers & walnut shelving. The sunken GR boasts a garden door to the large deck & sunny west-facing backyard, while the adjacent DR is surrounded by wall-to-wall windows overlooking the yard. Main floor laundry & custom mudroom add everyday convenience. The upper FR or optional fourth bedroom offers wood slat & shiplap feature walls, electric fp, wall of windows & access to a private balcony. The primary suite includes a custom built-in wardrobe & 2-piece ensuite. 2 additional bright spacious brs & family bath. The finished LL features a rec room w/wet bar, bar-top seating & full bath. Double o/s attached garage, paver stone landscaping, mature trees & fire pit patio. Steps from Assiniboine Forest & the Harte Trail...brand new & move-in ready!

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

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.

I have listed a new property at 6 Mayfield CRES in Winnipeg. See details here

S/S Thurs. Aug. 20, offers Tues. Aug. 25 after 6 pm. Rarely available! Enjoy carefree living in this beautifully maintained bungalow condominium, ideally situated on a quiet cul-de-sac in an excellent neighbourhood. The open-concept layout features a warm & inviting GR with a cozy corner FP. The adjoining dining area showcases hardwood flooring with an elegant inlay & an attractive alcove, adding character & charm. Spacious kitchen offers an abundance of cabinetry & counter space, along w/a lg island that's perfect for meal preparation or casual dining. A versatile den w/French doors provides the ideal space for a home office. The bright & comfortable sunroom features a vaulted ceiling, French drs & a garden dr leading to a generously sized deck—an ideal spot to relax and enjoy the outdoors. The main floor includes 2 brs, highlighted by a spacious primary suite w/private 3 pce ensuite. A 4-pce bath & convenient laundry rm complete the main level. The fully finished LL offers even more living space w/a large family-sized recreation room, an additional br & a 3 pce bath perfect for guests or teenagers. A generous storage room provides plenty of space for seasonal items and hobbies. C/air, HEF & an AT/2.

I have listed a new property at 31 Dumbarton BLVD in Winnipeg. See details here

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.

I have listed a new property at 71 Macalester BAY in Winnipeg. See details here

S/S Thurs. Aug. 20, offers Tues. Aug. 25 after 6 pm. Welcome to this beautifully updated bungalow featuring an open-concept design that's perfect for modern living. The freshly painted main floor offers a bright and inviting living and dining room combination with newer laminate flooring (2026), seamlessly flowing into the spacious kitchen. The kitchen is designed for both everyday living and entertaining, complete with granite countertops, an abundance of cabinetry, a centre island with breakfast bar, and a wraparound bar-top with additional seating. The main floor offers three comfortable bedrooms, including a primary bedroom with a convenient 2-piece ensuite. An updated 4-piece bathroom completes the main level. The fully finished lower level has been refreshed with newer carpeting (2026) and features a welcoming recreation room with a wet bar, two additional bedrooms, a 3-piece bathroom, and a laundry room complete with washer and dryer. New laundry room flooring was installed in 2026. Step outside to enjoy the fully fenced backyard, featuring a fire pit and a storage shed. High-efficiency furnace. Located on a quiet bay with close proximity to University of Manitoba.

I have listed a new property at 53 Harvard AVE in Winnipeg. See details here

S/S Thurs, Aug 20-offers Tues, Aug 25 after 1:00 p.m. 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.

I have listed a new property at 497 Brock ST in Winnipeg. See details here

S/S Wed. Aug. 19, offers Tues. Aug. 25 after 6 pm. Beautifully updated 2-storey in desirable River Heights with exceptional curb appeal! The exterior features newer siding & a welcoming covered front porch addition (2023) with modern stacked stone accents, fresh landscaping and a custom foyer w/convenient 2-piece guest bath. Inside, original hardwood floors, character ceilings & abundant natural light add warmth & charm to the living & dining rooms. The updated kit offers porcelain tile floors, granite counters, soft-close cabinetry w/organizers, tile backsplash, ss appliances & a large peninsula w/breakfast bar seating. Upstairs features 3 bright bedrooms w/hardwood floors & 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 those cooler evenings. Additional features include a HEF, C/AIR & newer HWT. A 22' x 13' detached garage (2015) provides parking & extra storage. Ideally located steps from Brock Corydon School & Cordova Park. This fabulous home is truly move in ready...don't miss out!