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4039 & 4041 Sissiboo Road
Digby County South Range B0W 1H0

$1,299,900
Multi-Family built: 2010

Main Photo: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 1: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 2: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 3: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 4: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 5: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 6: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 7: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 8: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 9: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 10: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 11: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 12: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 13: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 14: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 15: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 16: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 17: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 18: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 19: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 20: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 21: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 22: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 23: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 24: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 25: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 26: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 27: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 28: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 29: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 30: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 31: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 32: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 33: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 34: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 35: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 36: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 37: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 38: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 39: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 40: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 41: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 42: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 43: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 44: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 45: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 46: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 47: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 48: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Photo 49: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
Status:
Active
Prop. Type:
Multi-Family
MLS® Num:
202627685
Year Built:
2010
This exceptional 8.8 acre waterfront property blends relaxed bespoke lifestyle vibes alongside outstanding income potential. Tucked away from the road and surrounded by extensive landscaping, this private estate features a custom chalet style home, a fully self-contained in-law suite, and a separate waterfront cabin offering incredible possibilities for multi-generational living, short-term rentals, or supplemental income. The striking main home is designed to embrace its waterfront setting, with vaulted ceilings, exposed beams, expansive windows, and inviting living spaces that make the most of the spectacular west facing views. The self-contained suite above the garage provides comfortable independent space with a separate entrance, while the charming waterfront cabin with private covered deck is the perfect retreat for guests or a highly desirable vacation rental. Whether you're looking to offset your expenses, create a family compound, or invest in a property with unlimited potential, this unique offering delivers flexibility without compromising privacy or lifestyle. Spend your days enjoying the water, entertaining, or simply relaxing in the peaceful surroundings all just a short drive from the amenities of charming Digby.
Contact Listing Agent
Listing Sub-Area:
Digby County
Property Type:
Multi-Family
Multi-Family Type:
Triplex
Title To Land:
Freehold
Building Dimenions:
Irregular
Lot Size:
8.8 acre(s)
Prop Size:
3 to 9.99 Acres
Commercial / Retail Space:
No
# of Rental Units / Occupied:
0
Year built:
2010 (Age: 16)
Age:
16
Exterior Finish:
Wood Shingles, Stone
Foundation:
Concrete, Slab
Basement:
Partial, Partially Developed
Floor Finish:
Laminate, Slate, Softwood, Tile
Roof:
Metal
Heating:
Baseboard, In Floor, Stove
Fuel:
Electric, Pellet, Wood
Garage Description:
Double Attached, Heated, Wired
Driveway:
Circular, Gravel
Water Supply:
Pond/Lake
Water Type:
Fresh Water
Sewer:
Septic
Num Units:
3
Num 1 Bed Units:
1
Num 2 Bed Units:
1
Num 3 Bed Units:
1
Rental Income:
Yes
Balcony, Ensuite Bath, Family Room, Main Flr Fam Rm, Power, Secondary Suite, See Remarks, Wood Stove(s)
Appliances, Some Furnishings
Recreation Center, School Bus Service, Marina, Place of Worship, Beach
Stove - Gas, Dishwasher, Dryer, Freezer - Stand Up, Microwave, Refrigerator, Wine Fridge, Water Purifier, Water Softener
Propane Tank
Deck, Patio, Dock, Shed, Wharf, Boathouse
Lake
Yes
475'
Access: Lake, View: Lake, View: Other
Zoning:
GD
Possession Info:
Negotiable
Elementary School:
Digby Elementary School
French Imm Elementary School:
Digby Elementary School (Early)
French Imm High School:
Digby Regional High School (Late)
High School:
Digby Regional High School
Middle School:
Digby Regional High School
Listed Date:
Nov 09, 2026
Days on Mkt:
0
  • Photo 1: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 2: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    8.8 acres waterfront
  • Photo 3: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 4: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 5: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 6: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 7: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Living Area
  • Photo 8: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Waterview Kitchen - Main House
  • Photo 9: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 11: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Cathedral Ceilings
  • Photo 12: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 13: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Primary Suite
  • Photo 14: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 15: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Ensuite
  • Photo 16: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Repurposed Historic Timbers
  • Photo 17: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Upstairs Landing
  • Photo 18: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Bedroom 2
  • Photo 19: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Bedroom 3
  • Photo 20: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House (Bedroom 4)
  • Photo 21: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Full Bath 2
  • Photo 22: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Games Room
  • Photo 23: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 24: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Games Room Bar
  • Photo 25: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Wine Cellar
  • Photo 26: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Main House Powder Room
  • Photo 27: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Entrance to In Law Suite
  • Photo 28: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Entry to In Law Suite
  • Photo 29: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    In Law Suite Living Area
  • Photo 30: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    In Law Suite Waterview
  • Photo 31: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    In Law Suite
  • Photo 32: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    In Law Suite Bedroom 5
  • Photo 33: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    In Law Suite Bedroom 6
  • Photo 34: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    In Law Suite Full Bath
  • Photo 35: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Double Attached Garage
  • Photo 36: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Waterfront Cabin Outdoor Living
  • Photo 37: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 38: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Waterfront Cabin Main Living Area
  • Photo 39: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Waterfront Cabin
  • Photo 40: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Waterfront Cabin Full Bath
  • Photo 41: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Waterfront Cabin (Bedroom 7)
  • Photo 42: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Waterfront Cabin Kitchen Area
  • Photo 43: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Boathouse
  • Photo 44: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Covered Gazebo
  • Photo 45: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 46: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Fenced Dog Run
  • Photo 47: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
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  • Photo 48: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    West Facing Sunset Views
  • Photo 49: 4039 & 4041 Sissiboo Road in South Range: Digby County Multi-Family for sale (Annapolis Valley)  : MLS®# 202627685
    Photo 49 of 49
Data was last updated November 9, 2026 at 09:20 PM (UTC)
Area Statistics
Listings on market:
11
Avg list price:
$374,000
Min list price:
$149,000
Max list price:
$1,650,000
Avg days on market:
103
Min days on market:
5
Max days on market:
374
These statistics are generated based on the current listing's property type and located in Digby County. Average values are derived using median calculations. This data is not produced by the MLS® system.
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