Chris Pennycook
Office 204-989-5000 | chrispennycook@royallepage.ca
Office Listings
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152 Sun Valley Drive in Winnipeg: All Season Estates Residential for sale (3H) : MLS®# 202621537
152 Sun Valley Drive Winnipeg R2G 2W5 
$289,900Residential- Status:
- Active
- MLS® Num:
- 202621537
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 880 sq. ft.
Open House Sunday 12-1:30pm. Offers welcomed Tuesday Sept 1st. Welcome to an incredible opportunity to get into a neighbourhood you may have thought was out of reach! Priced at $289,900, this 3 bedroom, 1 bathroom attached home offers an affordable way to put down roots in a sought after area. The main floor features a bright and spacious living room with large windows, a functional kitchen and dining area, and plenty of natural light throughout. You’ll also find three bedrooms and the full bathroom, while downstairs the basement adds even more usable space with a rec room and plenty of storage. There’s room here to move in, make updates over time and truly make the home your own. Outside you have a fenced private yard and a large parking pad. The location is the real win, directly across from Ecole Sun Valley school and surrounded by the parks, amenities and established streets that make this neighbourhood so sought after. If location has been at the top of your wish list, this could be your way in! More detailsListed by Ally Gray-Beauchesne of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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14 Raden Drive in Headingley: Headingley South Residential for sale (1W) : MLS®# 202621509
14 Raden Drive Headingley R4J 1B3
$349,900Residential- Status:
- Active
- MLS® Num:
- 202621509
Offers presented September 2 evening 2026. South Headingley 100 x 234 foot lot with approx 60 feet frontage on Raden Drive. Cleared building site with partial shelterbelt. Services are installed and prepaid. Hard top lane approach to the property. Perfect opportunity to purchase a lot and choose your own builder! Quiet Location in the Hamlet! Come check this out! More detailsListed by Tyson Sonnichsen of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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270 Doran Bay in Winnipeg: Crestview Residential for sale (5H) : MLS®# 202621433
270 Doran Bay Winnipeg R2Y 1H5
$379,900Residential- Status:
- Active
- MLS® Num:
- 202621433
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,051 sq. ft.
Showings start August 27th, offers September 1st. Welcome to this charming 3-bedroom, 1.5-bathroom home tucked away on a quiet bay in Crestview. Filled with character, the home showcases many of its original mid-century finishes, complemented by beautiful hardwood floors and an abundance of natural light throughout. The main floor offers a comfortable and inviting layout with plenty of opportunity to appreciate, restore, or thoughtfully blend the home's original details with your own style. Downstairs, the finished basement provides a 2 piece bathroom and lots of additional living space, perfect for a family room, recreation area, home office, or hobby space. Outside, the beautifully landscaped backyard creates a peaceful retreat with established gardens, mature greenery, and a charming pond that adds to the character of the property. The home also features a covered deck with privacy fencing through the patio doors in the kitchen. Set on a bay with limited through traffic, this home offers a great combination of location, character, indoor living space, and a truly special backyard. A wonderful opportunity for anyone who appreciates mid-century charm. More detailsListed by Brendan Cade of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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53 Harmon Avenue in Winnipeg: Silver Heights Residential for sale (5F) : MLS®# 202621280
53 Harmon Avenue Winnipeg R3J 2P9
$379,900Residential- Status:
- Active
- MLS® Num:
- 202621280
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 1,239 sq. ft.
Showings start now, Offers reviewed September 2nd. A Great opportunity to make this house into a home and build equity, all at an affordable price. This 1 1/2 storey Silver Heights home is straight & solid with many upgrades. Located on a quiet bay this home features: hardwood floors throughout the main floor, spacious Living Room, Eat-in Kitchen, 2 Bedrooms and updated Bathroom on the main floor. The 2nd floor offers 2 bedrooms including the primary. The lower level is finished with a large Family Room w/built-ins, Laundry/Utility Room & 2nd full Bathroom. HE furnace, central air, updated windows. The fenced yard offers a deck with covered gazebo. Oversized single car Garage (18' x 22') with 12' door w/opener. Property being sold as is. Call your Realtor today to book your showing! More detailsListed by Dave Kramer of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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934 Byng Place in Winnipeg: East Fort Garry Residential for sale (1J) : MLS®# 202621279
934 Byng Place Winnipeg R3T 0Y5
$439,900Residential- Status:
- Active
- MLS® Num:
- 202621279
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 1,334 sq. ft.
Showings start August 27th, Offers reviewed September 1st eve. Welcome to a rare gem of a home in the heart of East Fort Garry! This fully updated Bungalow offers an open plan Living Room with gorgeous hardwoods throughout, & spacious Dining Room with built-in cabinets. Large & modern Kitchen complete with Cherrywood cabinets, stainless steel appliances & pantry. Primary Bedroom w/2 closets, plus 2 more generous sized Bedrooms. The updated 5 piece Bathroom has upgraded plumbing. Generous sized storage & Laundry Room with built-ins. Upgrades include: Shingles (26), Central Air (26), HWT (24), front exterior doors, windows, & more. Front driveway access to a covered Carport, plus an oversized Double Garage (24' x 26') that is fully insulated, heated, & has 9' ceiling! Fully fenced Backyard with mature landscaping, unistone Patio, and a great 12' x 16' Screen Room. All this on a 60' lot! Ideally located midblock on a tranquil street, steps from Riverside Drive, playground, BDI, Wildwood Golf, public transit, & shopping. Truly a great place to call home, book your showing today! More detailsListed by Dave Kramer of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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38 Baytree Court in Winnipeg: Linden Woods Residential for sale (1M) : MLS®# 202621330
38 Baytree Court Winnipeg R3P 2L2
$749,000Residential- Status:
- Active
- MLS® Num:
- 202621330
- Bedrooms:
- 4
- Bathrooms:
- 3
- Floor Area:
- 2,115 sq. ft.
S/S Friday August 28th with offers reviewed Thursday September 3rd at 6:00 P.M.// Quiet cul de sac location for this spacious cab over with great room layout featuring cathedral ceilings. Subzero refrigerator, double Decor ovens, and gas Jenn Air cook top in the large eat in kitchen. Gas fireplace and built in bookshelves in the family room. Maple hardwood floors throughout. Two bedrooms with built ins and a full bath finish the main floor. There is a five piece ensuite and W/I closet in the primary bedroom. The lower level boasts a recroom, games area, gym, and bed/den, a third full bath, and storage. Heated floors in the main entry and the ensuite. Stamped concrete patio area surrounds the inground pool. For those who like to garden there are raised garden beds in the back yard. Shingles in 2023. Pool pump and filters in 2025. 60+ lights converted to led in 2024. Some windows in 2019. Walking distance to schools and Community Club. More detailsListed by Claude Davis and Geoffrey Davis of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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508 Montague Avenue in Winnipeg: Riverview Residential for sale (1A) : MLS®# 202620164
508 Montague Avenue Winnipeg R3L 1T7
$449,900Residential- Status:
- Active
- MLS® Num:
- 202620164
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,201 sq. ft.
SS Aug 26/26. OH Sat 2-4. OTP Sept 1/26. Riverview charmer alert! This 1.5-story cutie packs a serious punch with 3 beds, 2 full baths and a fully finished basement that says “yes” to movie nights, home offices, or whatever your heart desires. Sip your coffee (or wine) in the three-season sunroom, then head out to the deck for some fresh-air fun. The fully fenced yard is ready for pups, kiddos, or your next garden project, no judgment either way. Tucked on a quiet mid-block lot with a single garage for easy in-and-out, this one checks all the boxes without breaking the bank on space or style. And the location? Chef’s kiss. Walk to BDI for that classic Winnipeg ice cream fix, or wander over to the Riverwalk on Churchill Dr. or to South Osborne for its beloved mix of shops, restaurants, and everyday amenities. Whether it’s patio season or soft-serve season, everything you need is just steps away. Cute, functional, and full of possibilities. Riverview living just got a whole lot better. More detailsListed by Tara Suffield of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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103 Lake Village Road in Winnipeg: Waverley Heights Residential for sale (1L) : MLS®# 202621277
103 Lake Village Road Winnipeg R3T 4M7
$344,900Residential- Status:
- Active
- MLS® Num:
- 202621277
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 920 sq. ft.
Open House Saturday, August 29th 1-3pm. Offers presented as received. Welcome to this 920 sq ft bungalow in desirable Waverley Heights. Offering 3 bedrooms, a 4-piece bath, and a functional layout, this home is ideal for first-time buyers, young families, students, or investors. The combined living and dining room features hardwood floors, large windows, and a cozy wood-burning fireplace with brick surround. The kitchen offers ample oak cabinetry, a peninsula island, and stainless steel fridge and stove. Three generously sized bedrooms complete the main floor. The lower level adds valuable living space with a spacious rec room, office area, laundry, and plenty of storage. Updated PVC windows, high-efficiency furnace (2021), hot water tank (2022), and central air complete the package. Outside, the fully fenced backyard features a patio, garden boxes, storage shed, and room for your own finishing touches. Conveniently located near the University of Manitoba, schools, parks, public transit, shopping, and restaurants. A great opportunity in a fantastic location. Book your showing today! More detailsListed by Tyson Sonnichsen of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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783 Borebank Street in Winnipeg: River Heights South Residential for sale (1D) : MLS®# 202621404
783 Borebank Street Winnipeg R3N 1G3
$419,900Residential- Status:
- Active
- MLS® Num:
- 202621404
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 923 sq. ft.
Showings start Thursday August 27, Offers on Monday August 31st. Welcome Home! This incredibly well maintained and upgraded River Heights bungalow features original hardwood floors, huge windows at the front and back that allow plenty of natural light. Renovated kitchen has quartz counters, stainless steel appliances, tile backsplash as well plenty of cabinets and drawers. Down the hall to 2 spacious bedrooms and a modern bathroom. The finished basement offers more space for relaxing, tons of storage and a second updated full bathroom. The 50' x 120' lot is fenced, large double garage as well as plenty of other space for kids or pets to play and a stone patio, great spot for a outdoor fireplace. Long list of upgrades, including windows, high efficiency furnace, central AC (2023), basement re-insulated (2024), back water valve + Sump pit (2025) and designer paint and lighting. This one is move-in ready! More detailsListed by Dan O'Brien of 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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965 McMillan Avenue in Winnipeg: Crescentwood Residential for sale (1Bw) : MLS®# 202620978
965 McMillan Avenue Winnipeg R3M 0T4
$349,900Residential- Status:
- Active
- MLS® Num:
- 202620978
- Bedrooms:
- 6
- Bathrooms:
- 2
- Floor Area:
- 1,856 sq. ft.
SS NOW! Offers as received. Calling All Investors, Flippers & Handymen — Crescentwood Opportunity! A true character home with endless upside and 1,856 sq. ft. of living space ready for transformation. Featuring a great layout, and rare upgrades already in place. This two-storey offers a traditional floor plan with large principal rooms, a formal dining area, and a spacious living room. Upstairs you’ll find three bedrooms, a 4-piece bath with original penny tile, and original hardwood floors under the carpet!The basement delivers excellent ceiling height and 3 additional rooms currently used as bedrooms (buyers to verify egress/code), plus another full bathroom. Perfect for future suite potential or expanded living space. A major bonus: the home features central air conditioning — a rare and highly desirable upgrade in character homes in this area — adding comfort and long-term value. Located steps from Corydon and Osborne Village, surrounded by restaurants, shops, schools, transit, and all the amenities that make Crescentwood one of Winnipeg’s most sought-after neighbourhoods. Whether you’re flipping, investing, or looking for a rewarding project, this property offers exceptional potential! Call now! More detailsListed by Carolina Facioli and Paula Facioli of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
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321 Guildford Street in Winnipeg: Deer Lodge Residential for sale (5E) : MLS®# 202621154
321 Guildford Street Winnipeg R3J 2J6
$379,900Residential- Status:
- Active
- MLS® Num:
- 202621154
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 1,520 sq. ft.
Showings start August 25th, Offers reviewed August 31st eve. Welcome home to this fantastic Family home in the heart of Deer Lodge! A well maintained 1 1/2 storey home featuring: 4 Bedrooms & 2 Bathrooms, centre hall plan with a spacious & bright Living Room, Dining Rooms with large window. Hardwoods throughout most of the main floor. Eat-in Kitchen with plenty of cabinets & all appliances included! Convenient Main floor Bathroom & a spacious Bedroom w/corner windows. The upper level offers a large Primary Bedroom complete w/walk-in closet, plus 2 more good sized Bedrooms & 2nd Bathroom. The lower level is mostly finished with a large Rec. Room space, storage area, cold room/pantry & a laundry area with washer & dryer included. Upgrades include: HE Furnace, central air-conditioning, HWT, shingles/eaves, & sump pump. Fully fenced Backyard complete with mature landscaping, patio, turf & storage shed. Detached Garage with opener plus a concrete pad providing extra parking. Perfect location on a great block, within walking distance to park, public transit, Assiniboine golf course, St. James Civic Centre & Assiniboine Park. Don't miss your opportunity to get into this neighbourhood at an affordable price! More detailsListed by Dave Kramer of Royal LePage Dynamic Real Estate- CHRIS PENNYCOOK
- ROYAL LEPAGE DYNAMIC REAL ESTATE
- 1 (204) 941-0573
- Contact by Email
Data was last updated August 27, 2026 at 06:35 PM (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