view of front facade with brick siding and a front lawn Features: lawn

More Photos More Photos

view of front of home with brick siding, a front lawn, and roof with shingles Features: lawn, porch

view of front of home with a front yard and brick siding Features: lawn

office space with light wood finished floors and baseboards Features: built in desk, hardwood floor

living room featuring light wood finished floors, a baseboard heating unit, and wooden walls Features: natural light, hardwood floor, baseboard radiator, wood wall

additional living space with baseboard heating, vaulted ceiling, and light wood-type flooring Features: natural light, vaulted ceiling, hardwood floor, baseboard radiator, wood wall

bonus room featuring baseboard heating and wood finished floors Features: baseboard radiator, vaulted ceiling, hardwood floor

bonus room with vaulted ceiling, wood finished floors, and wooden walls Features: vaulted ceiling, hardwood floor, wood wall

bonus room with wood finished floors, lofted ceiling, and wooden walls Features: hardwood floor, vaulted ceiling, wood wall

view of unfurnished sunroom Features: french doors, natural light

spare room featuring baseboards and light wood-style flooring Features: natural light, hardwood floor

unfurnished sunroom featuring wood finished floors and baseboards Features: hardwood floor, natural light, vent, crown molding

corridor featuring light wood finished floors and ornamental molding Features: vent, french doors, hardwood floor, crown molding, natural light, smoke carbon monoxide detector

empty room featuring crown molding and light wood-type flooring Features: crown molding, vent, hardwood floor

spare room featuring light wood-style flooring, crown molding, and heating unit Features: crown molding, space heater, vent, hardwood floor

unfurnished room featuring crown molding and light wood-style floors Features: hardwood floor, crown molding, natural light

empty room featuring ornamental molding, light wood-style flooring, and heating unit Features: crown molding, natural light, hardwood floor, space heater

spare room featuring ornamental molding and light wood finished floors Features: hardwood floor, crown molding, natural light

unfurnished living room featuring crown molding and light wood-style floors Features: sink, vent, hardwood floor, crown molding

spare room featuring light wood-type flooring and crown molding Features: hardwood floor, crown molding, natural light

bonus room featuring light wood-type flooring and baseboards Features: natural light, hardwood floor

spare room with ornamental molding and light wood-style flooring Features: natural light, crown molding, vent, hardwood floor

full bathroom with shower combination and dark wood-style floors Features: sink, toilet, mirror, vent, combined bath shower, hardwood floor

empty room featuring light wood-style flooring and ornamental molding Features: crown molding, natural light, hardwood floor

unfurnished bedroom with light wood-style flooring and ornamental molding Features: hardwood floor, natural light, crown molding, closet

kitchen featuring freestanding refrigerator, light tile patterned flooring, and dark countertops Features: tile floor, natural light, shaker cabinets, countertops, refrigerator

kitchen featuring tasteful backsplash, freestanding refrigerator, light tile patterned flooring, and dark countertops Features: shaker cabinets, refrigerator, natural light, countertops, backsplash, sink, medium brown cabinets, tile floor

kitchen featuring stainless steel electric stove, decorative backsplash, light tile patterned floors, brown cabinetry, and dark stone countertops Features: stone countertops, sink, medium brown cabinets, backsplash, shaker cabinets, range oven, tile floor

kitchen with tasteful backsplash, freestanding refrigerator, light tile patterned floors, dark countertops, and black / electric stove Features: countertops, shaker cabinets, light brown cabinets, backsplash, tile floor, refrigerator, natural light, range oven, sink

kitchen with electric range, tasteful backsplash, dark countertops, light tile patterned floors, and brown cabinets Features: countertops, backsplash, tile floor, sink, shaker cabinets, range oven, medium brown cabinets

laundry room featuring unfinished concrete floors and washer and clothes dryer Features: water heater, laundry, concrete floor, sink, natural light, separate washer dryer, low ceiling

unfinished basement with stairs, washing machine and clothes dryer, water heater, and heating unit Features: furnace, laundry, water heater, separate washer dryer, sink

unfinished basement with washer and dryer and electric panel Features: sink, laundry, separate washer dryer, electric panel

view of sunroom / solarium Features: natural light

rec room featuring wood finished floors and arched walkways Features: tv, arched walkways, hardwood floor, natural light

bedroom featuring light wood finished floors Features: hardwood floor

bedroom with light wood-type flooring Features: hardwood floor

bathroom featuring shower / bath combo, vanity, and tile patterned flooring Features: sink, vanity, mirror, tile floor, toilet, combined bath shower

living room with arched walkways, a ceiling fan, crown molding, and wood finished floors Features: hardwood floor, crown molding, ceiling fan, arched walkways, tv

kitchen featuring wooden walls, fridge with ice dispenser, light countertops, hanging light fixtures, and white cabinets Features: medium brown cabinets, tile floor, range oven, white cabinets, open shelves, sink, pendant lighting, refrigerator, wood wall, countertops

kitchen with electric stove, paneled fridge, white cabinets, wood walls, and light countertops Features: open shelves, refrigerator, tile floor, countertops, wood wall, medium brown cabinets, sink, range oven, white cabinets

back of house featuring a wooden deck, stairway, and brick siding Features: fence, central ac, balcony, deck

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For Sale - 106-108 SHEPHERD Street, Windsor, Ontario

106-108 Shepherd Street

Windsor , Ontario

$399,990

Est payment $1,921/mo

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Time on Jump 19 day

AI Summary *

Spacious duplex with two self-contained units and private entrances.
Bright living areas with generous bedrooms and updated finishes.
Low property taxes and great rental income potential.
Convenient access to schools, parks, shopping, and public transit.
Well-maintained with newer mechanicals and ample on-site parking.

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$ 19,999 ( 5% )

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Welcome to this exceptional duplex located in the heart of windsor, offering timeless character, modern comfort, and outstanding investment potential. This well-maintained property at 106–108 shepherd street east features two spacious, self-contained units, each with private entrances, full kitchens, and in-suite laundry. The main level showcases bright living areas with generous bedrooms and updated finishes, while the upper unit offers a warm and inviting layout ideal for families or professionals. With newer mechanicals, efficient gas heating, and ample on-site parking, this home is both practical and appealing. Nestled in a desirable, family-friendly neighbourhood, residents enjoy close proximity to excellent schools including queen victoria public school, hon. W. C. Kennedy collegiate institute, and james l. Dunn public school. Nearby green spaces such as jackson park, mitchell park, and gignac park provide abundant opportunities for outdoor recreation, while the property’s central location offers convenient access to shopping, dining, and essential services. Public transit is right at your doorstep, and commuters benefit from easy access to major routes and cross-border connections via the tunnel or bridge. Safety and convenience are key highlights, with windsor regional hospital, a fire station, and police headquarters all nearby. With strong rental appeal, low property taxes, and excellent income potential, this duplex is a versatile choice for investors or those looking to offset living costs. A rare opportunity in one of windsor’s most accessible and sought-after areas, this property combines comfort, functionality, and lasting value.

Listing ID26020762

Address106-108 SHEPHERD Street

CityWindsor, Ontario

Price$399,990

ConstructionBrick

FlooringCeramic or Porcelain, Hardwood or Engine…

Land Size30.12 FT BY 106.41 FT

TypeMulti-Family

StatusFor Sale

Extras

Subtype DuplexInclusions 2 REFRIGERATOR, 2 STOVES, WASHER, DRYEROwnership FreeholdFoundation BlockHeating / Cooling Central Air Conditioning, Forced Air, FurnaceHeating Fuel Natural GasHot Water Tank GasUtility Water Municipal WaterSewer Sanitary

Market Info

Date Listed Aug 25, 2026Days on Market 20

Listing Agency:
REMAX CARE REALTY

Co-Listing Agency:
REMAX CARE REALTY

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Listing Agency:
REMAX CARE REALTY

Co-Listing Agency:
REMAX CARE REALTY

* Data is provided courtesy of WECAR. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. The information is deemed reliable but is not guaranteed accurate by WECAR.

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For Sale - 106-108 SHEPHERD Street, Windsor, Ontario

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Market Info

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