366 Main Street
Annapolis County Middleton B0S 1P0

$465,000
Residential beds: 5 baths: 3.0 2,225 sq. ft. built: 1914

You could be here...
Photo 1: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 2: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 3: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 4: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 5: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 6: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 7: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 8: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 9: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 10: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 11: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 12: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 13: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 14: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 15: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 16: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 17: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 18: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 19: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 20: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 21: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 22: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 23: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 24: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 25: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 26: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 27: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 28: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 29: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 30: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 31: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 32: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 33: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 34: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 35: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 36: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 37: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 38: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 39: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 40: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 41: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 42: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 43: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 44: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 45: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 46: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 47: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 48: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 49: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Photo 50: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
Status:
Active
Prop. Type:
Residential
MLS® Num:
202600409
Bedrooms:
5
Bathrooms:
3
Year Built:
1914
The charm and lifestyle you have been looking for waits at 366 Main Street in Middleton. 5 bedroom pls den 3 bath renovated period infused character home on municipal services has enjoyed numerous updates while maintaining the features and feel of the early 1900s. Welcoming 45 foot front verandah open concept living area benefiting from period trim high ceilings wood floors a new kitchen period fireplaces one of them for show the other fitted with propane for use both gorgeous. A new primary suite in the back a further bedroom or two if you include the den a full bath laundry combo and a yet to be tricked out mudroom define the main floor. Upstairs 3 charming bedrooms with functional fanciful windows are serviced by a full bath. Situated on almost a half acre in the center of town enjoy that walkable lifestyle you have been dreaming about with amenities from dining shopping groceries schools and more mere minutes or less away. Dont think hustle and bustle think charming and quaint. Solar to be paid out appliances just over 2 years old windows and entry doors are new basement spray foamed for efficiency and comfort. Close to the NSCC campus or under 15 minutes to Greenwood. You can live your best life in the beating heart of the Annapolis Valley.
Main Street in Middleton - the true heart of the Annapolis Valley
Listing Sub-Area:
Annapolis County
Property Type:
Residential
Residential Type:
Single Family
Residential Style:
Detached
Title To Land:
Freehold
Home Style:
1.5 Storey
Exterior Finish:
Wood Shingles
Year built:
1914 (Age: 112)
Age:
112
Bedrooms:
5
Bedrooms Above Grade:
5
Bedrooms Below Grade:
0
Full Bathrooms:
3
Half Bathrooms:
0
Main Living Area:
2,225 sq. ft.
Floor Area:
2,225 sq. ft.
Building Dimenions:
45' x 30' - jog
Prop Size:
Under 0.5 Acres
Lot Size:
20,473 sq. ft.
Zoning:
residential
Water Supply:
Municipal
Sewer:
Municipal
Foundation:
Other, Stone
Floor Finish:
Carpet, Ceramic, Hardwood, Laminate
Roof:
Asphalt Shingle
New Constr.:
No
Basement:
Full
Heating:
Baseboard, Fireplace, Heat Pump -Ductless
Fuel:
Electric, Propane, Solar
Utilities:
Cable, Electricity, High Speed Internet, Telephone
Garage:
None
Garage Description:
none
Parking Description:
driveway off Maple Ave with paved parking for a number of vehicles
Driveway:
Double, Paved
Floor
Type
Size
Other
Main Floor
Living Room
18' × 16'
Main Floor
Dining Room
13' × 9'
Main Floor
Kitchen
14'6" × 8'6"
Main Floor
Primary Bedroom
13' × 9'
Main Floor
OTHER
12' × 6'6"
Main Floor
Laundry/Bath
9' × 6'6"
Main Floor
Den/Office
16' × 9'
- jog
Main Floor
Bedroom
15' × 9'
- jog
Main Floor
Mud Room
9'6" × 6'
6"
2nd Level
Bedroom
15' × 10'6"
2nd Level
Bedroom
15' × 10'
2nd Level
Bedroom
10'6" × 10'6"
Floor
Ensuite
Pieces
Other
Main Floor
Yes
-
13' x 7'6"
2nd Level
No
-
10' x 6'
Ensuite Bath, Propane Fireplace, Wood Fireplace, See Remarks
fridge, range, vented microwave, dishwasher, washer, dryer (all 2 years old), mirrors including the walk in, TV in LIV
Propane Tank, Other
Golf Course, Park, Playground, Shopping, Place of Worship
Landscaped, Level
No
Possession Info:
As agreed. A quicker close can be negotiated
Elementary School:
Annapolis East Elementary School
Middle School:
Middleton Regional High School
High School:
Middleton Regional High School
Listed Date:
Days on Mkt:
  • Photo 1: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    You could be here...
  • Photo 2: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Welcome to 366 Main Street
  • Photo 3: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    45' verandah to watch the world go by
  • Photo 4: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Come on in...
  • Photo 5: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    open concept
  • Photo 6: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Light and bright living area
  • Photo 7: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Generous size with beautiful floors
  • Photo 8: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    looking towards kitchen and dining
  • Photo 9: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    this fireplace is currently for show only
  • Photo 10: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    TV included
  • Photo 11: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Love the wood work
  • Photo 12: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    the heart of the home
  • Photo 13: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Fireplace benefits from propane
  • Photo 14: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Unique with personality
  • Photo 15: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    All the modern comforts
  • Photo 16: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Again nice and bright
  • Photo 17: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Lots of storage
  • Photo 18: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Loads of functional counter space
  • Photo 19: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Always love a window over the sink
  • Photo 20: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Adorable
  • Photo 21: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Photo 21 of 50
  • Photo 22: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Main floor Primary
  • Photo 23: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Enjoys walk in and ensuite
  • Photo 24: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Generous walk in
  • Photo 25: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    mirror is included
  • Photo 26: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Photo 26 of 50
  • Photo 27: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    tub to be installed prior to close
  • Photo 28: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Photo 28 of 50
  • Photo 29: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Photo 29 of 50
  • Photo 30: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Large for an ensuite
  • Photo 31: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Main floor laundry - hurray!
  • Photo 32: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Tucked in behind the door
  • Photo 33: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Nice and bright
  • Photo 34: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Nice tile in shower
  • Photo 35: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    main floor bedroom
  • Photo 36: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    main floor bedroom or den
  • Photo 37: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Upstairs bath
  • Photo 38: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    a good size with great storage
  • Photo 39: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    and a funky shower
  • Photo 40: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Bedroom 1 of 3 upstairs
  • Photo 41: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Photo 41 of 50
  • Photo 42: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Bedroom 2 of 3 upstairs
  • Photo 43: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Photo 43 of 50
  • Photo 44: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Bedroom 3 of 3 upstairs
  • Photo 45: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Photo 45 of 50
  • Photo 46: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Side exterior
  • Photo 47: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Nice long driveway off Maple
  • Photo 48: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Great level backyard
  • Photo 49: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    From the back of the house
  • Photo 50: 366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley)  : MLS®# 202600409
    Check out the recent solar install

Add'l Virt Tour 1 URL

Virtual Tour

Listed by Engel & Volkers
Data was last updated January 13, 2026 at 03:20 PM (UTC)
Area Statistics
Listings on market:
126
Avg list price:
$347,000
Min list price:
$60,000
Max list price:
$1,700,000
Avg days on market:
103
Min days on market:
1
Max days on market:
733
Avg price per sq.ft.:
$253.3
These statistics are generated based on the current listing's property type and located in Annapolis County. Average values are derived using median calculations. This data is not produced by the MLS® system.
KAREN DOOKS
PETE DOOKS