50 Shepherd Street, Bowral, NSW 2576
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Price Guide: $1,795,000- $1,974,500
50 Shepherd Street, Bowral, NSW 2576
4
2
759m²
138m²
•
house - house: one storey / lowset
Property Description
Listed on 27 Nov 2025
Perfectly positioned in one of Old Bowral's most tightly held pockets & set on a generous 759m2, established block, this enchanting character cottage blends timeless appeal with modern comfort. Just steps to picturesque 'Cherry Tree Walk' & a short stroll to Bowral's boutique cafés, restaurants & all the conveniences of town, this is a rare opportunity to secure a quintessential Highlands home with bonus self-contained accommodation. Warm, inviting & lovingly maintained, the property offers flexible living options for families, downsizers, investors, or those seeking a charming retreat with additional income. Behind its classic façade, the cottage reveals all the hallmarks of a traditional Bowral home. High ceilings, timber features & a cosy ambience, enhanced by thoughtful updates for effortless living. The three bedrooms include one with built-in robes, while the central lounge room is anchored by a beautiful open fireplace, perfect for winter evenings. Comfort is assured year-round with ducted gas heating & gas hot water. The country-style modern kitchen features a gas cooktop, dishwasher & an adjoining dining area overlooking the established gardens. A spacious & functional laundry with an additional shower & toilet is ideal for families or visiting guests. The home is surrounded by mature gardens, a thriving veggie patch & plenty of space for children, pets & outdoor entertaining. The property also offers: - Workshop/shed area - Garden shed - Off-street parking - Private, tree-lined boundaries - Deck to rear perfect for outdoor entertaining - Established vegetable gardens - A rare offering in an elite 'Old Bowral' location Privately tucked at the rear of the property is an additional studio, perfect for extended family, a home office, creative workspace, or guest accommodation. Currently tenanted & providing consistent income, this well-appointed retreat includes: - Kitchenette with electric cooking - Split-system air conditioning - Master bedroom with built-ins - Ensuite bathroom Homes in this tightly held neighborhood are rarely offered to the market, especially those just footsteps from Cherry Tree Walk & an easy walk to the heart of Bowral. With charm, flexibility & income potential, this is a standout opportunity not to be missed. For further information or to arrange your inspection contact Matthew Anstee 0400 555 088 or Kristy Tuddenham 0448 555 054
Property history
A breakdown of how regularly this property entered and exited the market for sale or lease.
$455 WEEKLY
$185,000
Median house price trends
Comparing the price trend of houses in Bowral against the state of New South Wales over the last 4 years. Source: CoreLogic
Market activity
A snapshot of how quickly properties are selling in the area and how many are currently available.
93 Days
House median days on market
77 Days
Unit median days on market
317 Properties
Sold in last 12 months
144 Properties
Available in the last month
Bowral residents
Key characteristics of the residents in the area, view the full breakdown of the suburb here.
60+
Is the most common age range
Outright Owners
Most common occupant type
Couples
Most common household profile
Professionals
Most common occupation
Detached Houses
Most common property type
Nearby education
Schooling and educational options in the area, for all ages.
Aurora Southern Highlands Steiner School
K - Yr 12
Independent
Bowral Public School
K - Yr 6
Government
Southern Highlands Christian School
K - Yr 12
Independent
St Thomas Aquinas Catholic Primary School
K - Yr 6
Catholic
Get a wider view
Widen your research to learn about the suburb, council or state that this property belongs to.
Bowral
View the suburb data
Wingecarribee
View the council data
New South Wales
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Explore surrounding suburbs
Learn about neighbouring suburbs to see if they are better suited to your budget or lifestyle.
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Frequently asked questions
The property at 50 Shepherd Street includes 4 bedrooms, 2 bathrooms and no assigned parking spaces.
50 Shepherd Street in Bowral has a land size of approximately 759 square metres and an internal floor area of around 138 square metres.
50 Shepherd Street in Bowral, New South Wales, is close to local schools such as Aurora Southern Highlands Steiner School, Bowral Public School, Southern Highlands Christian School, St Thomas Aquinas Catholic Primary School, Aurora Southern Highlands Steiner School, Bowral High School and Southern Highlands Christian School
As of 3/1/2024, the property at 50 Shepherd Street is currently rented out.
