155 Chestnut Street
Wolseley Winnipeg R3G 1R5

$647,900
Multi-family beds: 5 baths: 4.0 2,428 sq. ft. built: 1909

Welcome to an investment property you'll be proud to own!
Photo 1: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 2: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 3: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 4: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 5: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 6: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 7: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 8: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 9: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 10: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 11: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 12: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 13: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 14: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 15: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 16: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 17: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 18: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 19: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 20: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 21: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 22: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 23: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 24: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 25: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 26: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 27: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 28: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 29: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 30: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 31: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 32: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 33: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 34: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 35: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 36: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 37: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 38: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 39: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 40: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 41: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 42: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 43: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 44: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 45: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 46: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 47: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 48: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 49: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Photo 50: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
Status:
Active
Prop. Type:
Multi-family
MLS® Num:
202619863
Bedrooms:
5
Bathrooms:
4
Year Built:
1909
5B//Winnipeg/24 hrs notice. HOUSE HACK OPTION - GET YOUR MORTGAGE PAID!! Rare opportunity to own a beautifully maintained triplex in Wolseley. This Triplex has been cared for by long-term owners who invested thoughtfully in both the building's infrastructure & quality of its suites while preserving the character & craftsmanship. Fully renovated and converted to a legal triplex in 2006 w/ permits, offers an exceptional blend of modern mechanics, stability & income potential. The spacious main flr suite is now vacant (possible rent $1950/mth+), creating an ideal opportunity for an owner-occupier unit. This bright & inviting 2bdrm, 2bthrm unit features lovely character details, generous living spaces & a single grg. Upper suites have been extensively updated in '18 w/ maple flrs, quartz counters & attract quality long-term tenants (current leases 2nd flr $1630, 3rd flr $920) Located w/in walking distance of shops, transit, parks, U of W, HSC & all the amenities that make Wolseley so desirable. Major upgrds incl copper wiring, PVC windws, reno kitchens, baths, flrs, HWT ('21), HE furnace & central A/C ('22), & ext paint ('25), weeping tile, waterprfing, sump. A truly turnkey investment in an exceptional location! (id:2493)
Property Type:
Multi-family
Common Interest:
Freehold
Property Attached:
Yes
Total Living Area:
2,428 sq. ft.
Taxes:
$4,481 / 2026
Community:
Wolseley
Security Features:
Smoke Detectors
Structure Type:
Triplex
Appliances Included:
Washer, Dishwasher, Dryer, Microwave, Alarm System, Blinds, Storage Shed, Two stoves, Garage door opener, Garage door opener remote(s), Two Refrigerators
Bedrooms:
5
Bathrooms:
4.0
Half Bathrooms:
0
Cooling:
Central air conditioning
Fireplace:
Yes
Fireplaces:
1
Fireplace Type:
Insert, Electric
Floor finish:
Tile, Laminate, Wood, Wall-to-wall carpet
Heating:
Baseboard heaters, Forced air, Electric, High-Efficiency Furnace, Natural gas
# Storeys:
2.5
Water:
Municipal water
Sewer:
Municipal sewage system
Lot Frontage:
33'
Lot Details:
33 x 93
Lot Features:
Flat site, Paved lane, Balcony, No Smoking Home, No Pet Home, Sump Pump
Parking:
Detached Garage, Rear
Total Parking Spaces:
3
Road Surface:
Paved road
Floor
Type
Size
Other
Main level
Living room
14'6" × 10'2"
-
Main level
Primary Bedroom
12'6" × 12'2"
-
Main level
Kitchen
17'9" × 7'7"
-
Main level
Laundry room
6'8" × 4'6"
-
Main level
Foyer
13'4" × 8'9"
-
Upper Level
Bedroom
11'8" × 11'7"
-
Upper Level
Primary Bedroom
12'2" × 11'1"
-
Upper Level
Living room/Dining room
11'7" × 11'2"
-
Upper Level
Family room
12'2" × 11'1"
-
Upper Level
Kitchen
11' × 10'
-
Third level
Great room
18'1" × 14'6"
-
Third level
Eat in kitchen
13'3" × 10'9"
-
Third level
Bedroom
10'1" × 8'8"
-
Basement
Bedroom
11'3" × 9'1"
-
Basement
Recreation room
11'2" × 9'9"
-
Basement
Den
12'1" × 10'4"
-
Basement
Utility room
7'8" × 6'8"
-
  • Photo 1: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Welcome to an investment property you'll be proud to own!
  • Photo 2: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Wolseley charm, location, and curb appeal in one package.
  • Photo 3: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Fully licensed with annual fire inspections completed.
  • Photo 4: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Welcome to the main floor unit! Potential rent $1985 (or higher). Such a gorgeaous space!
  • Photo 5: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Wonderfully maintained by the tenants, it offers charm, brightness, character, and nice detailing..
  • Photo 6: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Fully renovated in 2006 to create this space. With vacancy on possession, this could be your owner occupied unit.
  • Photo 7: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Photo 7 of 50
  • Photo 8: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Beautiful light, flooring, and open to the main area makes this space feel connected to it all.**photo has been digitally enhanced**
  • Photo 9: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    **photo has been digitally enhanced**
  • Photo 10: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    A super impressive space with character details preserved and modern updates enhancing it all **photo has been enhanced**
  • Photo 11: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Includes: 3 fridges, 3 stoves, and 3 dishwashers between all the units. **photo has been digitally enhanced**
  • Photo 12: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    So much millwork and counter space to utilize in this updated kitchen.
  • Photo 13: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Back entrance closet and mudroom space, dining area as an option too!
  • Photo 14: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Spacious primary bedroom on the main floor.
  • Photo 15: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Photo 15 of 50
  • Photo 16: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Eye-catching 3 pce en-suite off the main floor primary bedroom.
  • Photo 17: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Full basement is part of the main floor units space - room for a rec room, play area, gym, office, etc! **photo has been digitally enhanced**
  • Photo 18: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    This space has been spray foamed, and the basement has been full water proofing, new weeping tilesm sump pump, and exterior rigid insulation. **photo has been enhanced**
  • Photo 19: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    This is an investment property that has seen the last two owners take pride in it and make it like their own home. With tenants who care as well, it shows from top to bottom!
  • Photo 20: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Another part of the basesment ot utilize.**photo has been enhanced**
  • Photo 21: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Potential 2nd bedroom in the basement - window may not meet egress. **photo has been digitally enhanced**
  • Photo 22: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Second full bath off the potential bedroom.
  • Photo 23: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Updated mechanics as well with a HE furnace 2022, HWT 2021, sump pump, AC.
  • Photo 24: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Laundry is on the main floor and is shared by all the tenants.
  • Photo 25: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Second floor unit - bright and open as well. Another neat and tidy space with great tenants.
  • Photo 26: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    This unit rents for $1630 and is renewed until July 31, 2027. Tenants have been here 2 years and love it!
  • Photo 27: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Photo 27 of 50
  • Photo 28: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Updated kitchen, baths, and flooring 2018.
  • Photo 29: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Maple hardwoods, quartz counters, appliances.
  • Photo 30: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Such a nice, modern, updated space.
  • Photo 31: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Second living space or den, could be a cozy and homey dining area as well.
  • Photo 32: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Cozy and homey.
  • Photo 33: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Photo 33 of 50
  • Photo 34: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Second bedroom.
  • Photo 35: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Photo 35 of 50
  • Photo 36: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    The unit offers 2 bedrooms, 1 bath, 2 living spaces.
  • Photo 37: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Photo 37 of 50
  • Photo 38: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Second bathroom.
  • Photo 39: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Third floor unit. This tenant has been here 3 years. $920 per month with lease expiry Aug 2027.
  • Photo 40: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Everything well taken care of. Updated in 2018 as well.
  • Photo 41: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    **photo has been digitally enhanced**
  • Photo 42: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    **photo has been digitally enhanced**
  • Photo 43: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    **photo has been digitally enhanced**
  • Photo 44: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Kitchen with qusrtz counters, black millwork, tiled wall, maple floors.
  • Photo 45: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    And the perfect dining nook.
  • Photo 46: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    The desirable location of this building makes vacancies almost never heard of. Close to U of W, HSC, transit, and parks.
  • Photo 47: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Cute and cozy.
  • Photo 48: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Beautiful tile detail.
  • Photo 49: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Third bathroom.
  • Photo 50: 155 Chestnut Street in Winnipeg: Multi-family for sale : MLS®# 202619863
    Main floor tenant has use of the garage, and one outdoor parking stalls for the other two units included with their lease.
Listed by RE/MAX EXECUTIVES REALTY
Data was last updated August 13, 2026 at 06:15 PM (UTC)
RYAN AUXTERO PERSONAL REAL ESTATE CORPORATION
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