Chris Pennycook

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 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 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 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 214 4314 Grant AVE in Winnipeg. See details here

S/S Thurs. Mar. 5, offers Tues. Mar. 10 after 6 pm. Rare opportunity to this 3-bedroom, top-floor unit in a desirable & quiet condo building. Bright, updated & exceptionally well maintained, this home features newer laminate flooring & fresh paint throughout. The galley-style eat-in kitchen offers an abundance of cabinetry, all appliances & a newer patio door leading to a large covered balcony overlooking peaceful treed views. A pocket door provides added privacy to the spacious LR, while the open living & dining areas create an inviting space for everyday living & entertaining. The thoughtful layout includes a private guest bedroom with adjacent 3-piece bath, while the primary suite features its own 4-piece ensuite. The versatile third bedroom is ideal as an office, den or gym. Convenient in-suite laundry w/storage. Residents enjoy excellent amenities including a large party room perfect for family gatherings, plus storage lockers located on the same floor. Outdoor parking stall #32 is included, with option to rent a second space. Condo fees cover parking & all utilities for worry-free living. Ideally located steps to the curling club & arena. Minutes to shopping, restaurants & everyday conveniences.

I have listed a new property at 746 Haney ST in Winnipeg. See details here

S/S Thurs. Oct. 23, offers presented Tues. Oct. 28 @6 pm. Immaculate, updated & rare find in Charleswood! This beautiful 2,206 sq ft cabover offers space, style & comfort for the whole family. Vaulted ceilings & abundant natural light create an airy, open feel. The inviting foyer leads up to a bright open-concept living, dining & entertaining area complete with a wet bar...perfect for gatherings. The updated kitchen (2015) features soft-close cabinetry, quartz counters, ss appliances & island w/built-in oven & waterfall quartz breakfast bar. Patio doors open to a large tiered deck overlooking the expansive backyard w/patio, firepit, veggie garden & plenty of trees. The family room w/gas fireplace is ideal for relaxing while enjoying backyard & wildlife views. 2 bedrooms, full bath & laundry complete the main level. The private primary suite upstairs offers a WICC & 4-piece ensuite w/jetted tub & walk-in shower. The fully finished LL provides flexible space with 3 more bedrooms, full bath & ample storage. Updates include roof & HWT (2024), HEF & C/AIR (2021) & flooring (2015), C/VAC & AT/2 plus storage/play shed. Fabulous family location...steps to Harte Trail, off-leash dog park & all amenities.

I have listed a new property at 19 Collett COVE in Winnipeg. See details here

S/S Thurs. Sept. 4, offers presented Tues. Sept. 9 after 6 pm. Immaculate and completely remodeled bungalow nestled on a quiet cul-de-sac in Charleswood. Featuring soaring ceilings and an open floor plan, the great room impresses w/a striking floor-to-ceiling fireplace feature & expansive windows w/automated blinds. The dining area offers wall-to-wall built-in storage & display cabinetry, while the stunning white kitchen boasts soft-close cabinetry, quartz countertops, ss appliances & a family-sized island w/attached table for casual dining. A main floor guest bedroom or office, a spacious primary suite with a luxurious remodelled 5-piece ensuite w/WICC, plus a convenient laundry room w/new washer & dryer (2025) & guest bath complete this level. The bright & spacious LL, renovated in 2019, includes a large rec area w/electric fireplace, games area, wet bar, two generous bedrooms, 3-piece bath (2022) & abundant storage. Major updates include shingles, furnace, central air & HWT (2019), along with newer windows and doors. Enjoy the fully fenced backyard w/deck & patio. Underground sprinkler. Built on piles. AT/2. Walking distance to Assiniboine Park & Forest. Close to schools, shopping & dining.

I have listed a new property at 62 Brittany DR in Winnipeg. See details here

S/S Thurs. July 17, offers presented Tues. July 22 after 6:00 pm. This charming 2-bedroom 1626 sq. ft. bungalow in south Charleswood is nestled on a fabulous treed lot with a fully fenced backyard. The Tyndall stone exterior adds to the home’s pretty curb appeal. Step inside to a welcoming foyer that opens to a bright living & dining room w/built-in cabinet alcove & rich handscraped hardwood floors. The bright white kitchen features matching hardwoods, ample cabinetry w/organizers, tile backsplash & peninsula w/breakfast bar for casual dining. A cozy sunken FR features an electric fireplace & patio doors opens to your own private paradise, featuring an inviting 19' x 15' screened sunroom & a beautiful landscaped backyard. A gas line hookup for the bbq offers added convenience. The spacious primary bedroom includes a WICC & 3-piece ensuite. A second bedroom makes a great guest room or home office. A 4-piece main bath & laundry room complete the main level. The basement is ready to develop w/your personal touch...roughed-in plumbing already there. AT/2 w/concrete driveway. Walking distance to Harte Trail & Assiniboine Forest. Don't miss this great opportunity to own this impeccably maintained home!

I have listed a new property at 46 Deerpark DR in Winnipeg. See details here

S/S Thurs. July 17, offers presented Tues. July 22 after 6:00 pm. Step into this truly exceptional family home where timeless elegance meets everyday comfort—an absolute gem that radiates pride of ownership at every turn! From the moment you enter, you will be wowed by the dramatic wood-vaulted ceiling, elegant bay windows, & immaculate hardwood floors in the spacious living & dining rooms. At the heart of the home lies the warm & inviting kitchen & family rm—perfect for casual family living or entertaining friends. The chef's kitchen features granite counters, ample cabinetry, a 5-burner gas cooktop, island, & a cozy casual dining area with a window overlooking the beautifully manicured backyard. Patio drs lead to a deck with a relaxing hot tub—perfect for entertaining. The sunken family rm offers a warm ambiance with a wood-burning fireplace, built-in display shelves, & a garden door to the deck. Enjoy the convenience of main flr laundry & a 2-piece bath. Upstairs, you will find 3 bedrooms including a stunning primary suite with vaulted ceiling, hardwood flrs, sitting area, & a luxurious 4-piece ensuite. The bsmt offers endless potential, a dedicated wine rm, & ample storage. C/vac. Shingles 2025.

I have listed a new property at 107 Bramble DR in Winnipeg. See details here

S/S Thurs, July 10-offers presented Tues, July 15 after 6:00 pm....Rarely offered! Nestled on a quiet cul-de-sac, this exceptional 2,247 sq. ft. family home is located in the highly sought-after & well-established Charleswood neighbourhood—renowned for its community charm, & unbeatable location. This lovely 2 storey features a spacious formal LR & DR complete with hardwood flrs & elegant bay windows, perfectly designed for comfortable living & entertaining. The bright eat-in kitchen boasts granite countertops, ample cabinetry with organizers, & a garden dr to a large deck. Sunken FR offers a cozy retreat with a stunning wood-burning fireplace. A convenient half bath & laundry rm complete the main level. Upstairs, you will find a versatile office space, 3 generously sized bedrooms, a full 4-piece bath, & a luxurious primary suite with a wicc & 4-piece ensuite. The LL adds even more living space with a family size rec room, games room & a 3-piece bath. Step outside to a spacious & private pie-shaped lot with a beautifully fenced & landscaped yard, complete with a generous deck ideal for entertaining & ample space for kids to run & play. Piled. A/C 2025. Located near scenic walking paths, shops & dining.