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$374,500
4 Beds ⋅ 2 Baths ⋅ 202617448 MLS
4 bedroom, 1.5 bath home in Middleton, set on an oversize 2 acre lot that gives room to roam, minutes from downtown amenities, highway 101 access, and under 15 minutes to fast-growing CFB Greenwood. This well maintained property features mature landscaping and gardens throughout, with trails winding through the trees, a gazebo tucked among the perennials, apple trees, established perennials, and a pool for summer days. A detached garage and paved drive complete the grounds, offering plenty of parking and storage. Inside, hardwood floors run through the principal living spaces and the focal point is a deluxe custom kitchen with generous counter space and cabinetry. Two bedrooms are located on the main floor, including the primary, with two more bedrooms upstairs for family or guests. The heavy lifting has already been done here: central heat pump (2025), 200 amp breaker panel + 30 amp generator panel, spray foam insulation in the basement, recent roof shingles, many newer windows, and a pellet stove for added comfort on cooler nights. Appliances are included. Little to do but move in and enjoy a home and grounds that have been well cared for.

112 Main Street, Middleton
$380,000
2 Beds ⋅ 202615765 MLS
Why choose between a home and an investment when you can have both? This charming property gives you the best of both worlds, offering comfortable living with built-in income potential, all within walking distance to everything Middleton has to offer, including the hospital, pharmacy, NSCC, public transit, shops, and more. Inside you'll find two spacious 2 bedroom units, each with their own power meter, in unit laundry, and appliances included. The lower unit also features a bonus den and bright sunroom, giving you plenty of flexibility for a home office, guest room, or even a third bedroom. Fresh paint throughout gives the home a bright, move-in ready feel because who doesn't love crossing "paint" off the to do list? Step outside and you'll find a backyard that's ready to steal the show. Mature fruit trees, berry bushes, colourful gardens, and a detached garage make this outdoor space just as inviting as the inside. And don't overlook the huge attic, it's full of potential and just waiting for your Pinterest dreams (or practical plans) to come to life. This home has been lovingly maintained with major updates already taken care of, including a new furnace (2016), updated electrical (2020), oversized hot water tank (2019), and added insulation for improved efficiency. The big-ticket items? Already checked off. Whether you're growing your investment portfolio or looking for a smart way to help pay the mortgage, this property makes good financial sense without sacrificing charm. One unit is already tenant occupied, so you can start earning from day one. With municipal water and sewer, a fantastic location, and endless possibilities, this one's bringing the charm and the paycheck. Don't let it be the one that got away!

68 Connaught Avenue, Middleton
$375,000
2 Beds ⋅ 1 Baths ⋅ 202615385 MLS
Welcome to 26 Spring Garden Road in the charming Town of Middleton, nestled in the heart of Nova Scotia's beautiful Annapolis Valley. This tastefully updated home offers 2 bedrooms, 1 full bathroom, and flexible living space with potential for a third bedroom, making it an excellent option for first-time buyers, downsizers, retirees, or growing families. Step inside to discover a bright and inviting open-concept main living area designed for comfortable everyday living and entertaining. The home offers approximately 1,200 sq. ft. of living space plus a finished basement, providing additional room for a home office, den, hobby space, or guest accommodations. The upper loft retreat offers a private and versatile area ideal for a bedroom, workspace, or children's retreat. Extensively maintained and upgraded, this property provides peace of mind with new vinyl siding, new shingles, a newer oil tank (approximately 3-4 years old), updated chimney brickwork, and a beautifully renovated bathroom. Heating options include a high-efficiency dual-head heat pump serving both the main floor and loft, a CSA-certified and WETT-tested wood stove, and a backup hot-water baseboard furnace, providing comfort and flexibility throughout the seasons. The updated kitchen features a large vinyl window overlooking established vegetable gardens, creating a bright and pleasant space for cooking and gathering. Outside, the property shines with mature landscaping, colourful gardens, year-round greenery, and beautiful climbing roses that enhance the deck and garage area. The detached wired garage offers excellent versatility for vehicle storage, a workshop, hobbies, or additional storage.An 8' x 10' garden shed provides even more functional space for tools and seasonal equipment.Location is everything,and this property delivers exceptional convenience.Enjoy easy access to grocery stores, pharmacies, banks, restaurants, hardware and building supply stores,schools, Nova Scotia Community college

26 Spring Garden Rd Middleton, Ns, Middleton
$359,500
4 Beds ⋅ 1 Baths ⋅ 202615238 MLS
Conveniently located in town and within walking distance to shops, schools, and everyday amenities, this home offers comfortable living in a desirable location. A spacious entryway welcomes you inside and leads up to the main living area, featuring a bright and inviting living room, a functional kitchen with ample workspace, and a separate dining area perfect for family meals and entertaining. The home offers four bedrooms, providing plenty of space for a growing family, guests, or hobbies. One of the bedrooms could easily be converted into a home office, making it ideal for those working remotely or seeking additional flexibility. A full bath completes the layout. The basement is full and undeveloped but has good height if someone wanted to create another finished space. This home heats with forced air and a heat pump. Outside is a rear deck, garage and the half acre lot has space for a garden or whatever you have plans for. With its appealing location and versatile floor plan, this property is a great opportunity for first-time buyers, families, or those looking to enjoy in-town living.

93 School Street, Middleton
$444,900
4 Beds ⋅ 3 Baths ⋅ 202614539 MLS
Step into a piece of history with this beautifully restored Victorian residence. Rich in character and thoughtfully updated, this stunning 4-bedroom century home blends timeless charm with modern comfort, ready to welcome its next chapter. Inside, you’ll find impressive ceiling heights, large sun-filled windows, and elegant wood trim that highlight the home’s original craftsmanship, along with a stunning original staircase that serves as a true focal point. The spacious layout offers both functionality and warmth, featuring an open-concept kitchen complete with a large island and cozy eat-in nook, a formal dining room with walkout to a private back patio, a comfortable family room, and a classic formal living room. The inviting front entry showcases custom library built-ins and leads to a bright sun porch—perfect for quiet mornings or evening relaxation. Modern upgrades ensure year-round comfort, including efficient heat pumps, a wood stove, and full bathrooms on both the main and second levels, plus a private en suite off the primary bedroom. Skylights add to the airy feel, while thoughtful updates preserve the home’s authentic Victorian appeal. Set on a rare double town lot, the fully fenced backyard has been lovingly transformed into a private garden oasis, featuring mature landscaping, blooming flowers, vegetable gardens, and a workshop space—ideal for hobbyists or additional storage. Located just a short walk to amenities—schools, shops, restaurants, recreational facilities, and the hospital—this property offers both convenience and community. With Kingston and Greenwood only a short drive away, it’s perfectly positioned for families or commuters alike. This property offers commercial zoning potential, opening the door to a variety of opportunities—from a home-based business to a boutique retail venture. A truly unique and eye-catching property where history, charm, and opportunity come together.

145 Commercial Street, Middleton
$475,000
3 Beds ⋅ 3 Baths ⋅ 202612514 MLS
Welcome to 10 Connaught Ave, Middleton. A truly turnkey property where quality craftsmanship and pride of ownership are evident throughout. Situated on an incredible 3.9-acre lot, believed to be the largest residential lot in Middleton — this exceptional 3-bedroom, 3-bathroom home offers privacy, space, and convenience all within town limits.Completed to a high standard throughout, this home has seen extensive recent upgrades including: a new asphalt roof on the house, new metal roof and fascia on the detached garage, new 220 electrical panel with mast and main line to the road, new electric water heater, high-end kitchen range and dishwasher, newer refrigerator. Fresh paint in each room runs throughout the main level and a new black powder-coated chain link fencing surrounding the house to keep your pup safe are a few more of the recent upgrades. The heavy lifting is done. The main level features beautiful refinished hardwood floors throughout, a spacious primary suite with ensuite bath and stunning picture window overlooking the property, a second bedroom, and a bright living/dining area highlighted by a new propane fireplace and oversized picture window with remote awning. Down the hall from the kitchen you will find a massive butler’s pantry providing exceptional storage and prep space and an oversized linen closet.The fully finished lower level offers incredible flexibility with a third bedroom, third full bath, family room, storage closet and an additional 18x19 bonus room with hardwood floors and abundant natural light — ideal for a games room, office, gym, or future in-law suite conversion. An unfinished attic space with full walk up staircase access provides excellent future development potential.Outside, enjoy a paved driveway, detached garage with workshop, new screen room off the walkout basement, fruit trees, grape vines, walking trails, and a beautiful mix of cleared and forested land running within a stone’s throw from the Annapolis river.

10 Connaught Ave Avenue, Middleton
$380,000
3 Beds ⋅ 2 Baths ⋅ 202612145 MLS
Nostalgia! Located in one of the most historic and desirable areas in town, 26 Park Street offers a coveted central location. She is close to all amenities. Under the care of thoughtful homeowners, upgrades include a new furnace, heat pump, and a kitchen remodel. 26 Park Street has great bones and can be dressed however her new home owner desires! Corner lot with beautiful perennial beds, back patio, gazebo and shade trees along with an attached garage, round out this offering. She's a great deal.

26 Park Street, Middleton
$319,000
3 Beds ⋅ 1 Baths ⋅ 202609092 MLS
Discover the Middleton Community in the Heart of the Annapolis Valley for any stage of life, within walking distance to the hospital, school, and the Middleton shopping area, and only 15 minutes from the amenities of Kingston and CFB Greenwood. The home is nicely set back from the street with a wooded forest back lot. The Rotary Park next door is great for walking and sporting events. The front deck gives you morning sun for most of the day and the rear deck gives you shade and evening sunsets. The home is in great condition with a bright eat-in kitchen opening to the spacious living room, 3 bedrooms and a 4 pc. bath. The basement is open with exterior walls insulated and drywalled ready for future development. The detached garage is wired, insulated and ready for your vehicle and workshop. Come see if this is the home for you! Now vacant for quick possession.

1 Pinecrest Drive, Middleton
$329,900
5 Beds ⋅ 202608871 MLS
INVESTORS/ DUPLEX/ IN-LAW SUITE  /SINGLE FAMILY HOME Welcome to this versatile and centrally located 4-bedroom, 2-bathroom single-family home in the heart of Middleton, Nova Scotia. Perfectly suited for extended families or investment opportunities, this property features a fully functional lower-level in-law suite and can easily be utilized as an over/under duplex. Ideally situated within walking distance to schools, shopping, and the local hospital, with public transit nearby, this home offers both convenience and accessibility. The circular driveway provides ample parking and easy access for multiple vehicles. Inside, both units have seen numerous updates, including fully renovated kitchens and bathrooms—each with its own laundry facilities. The home features 22 new windows, newer roof shingles, some new flooring, and has been freshly painted throughout the majority of the space. Enjoy outdoor living with a brand new front veranda (25.3 x 8.6) and a spacious back patio (17 x 10), complete with wheelchair access to the lower-level entrance, enhancing accessibility and functionality. Each unit is equipped with separate power meters, while heating costs are covered by the homeowner. The lower level has been used as an in-law suite (no rental income previously collected), offering flexibility for future use. While the home would benefit from some finishing touches, it is move-in ready and presents a fantastic opportunity for families or investors alike.

15 George Street, Middleton
$329,900
4 Beds ⋅ 2 Baths ⋅ 202608868 MLS
INVESTORS/ DUPLEX/ IN-LAW SUITE  /SINGLE FAMILY HOME Welcome to this versatile and centrally located 4-bedroom, 2-bathroom single-family home in the heart of Middleton, Nova Scotia. Perfectly suited for extended families or investment opportunities, this property features a fully functional lower-level in-law suite and can easily be utilized as an over/under duplex. Ideally situated within walking distance to schools, shopping, and the local hospital, with public transit nearby, this home offers both convenience and accessibility. The circular driveway provides ample parking and easy access for multiple vehicles. Inside, both units have seen numerous updates, including fully renovated kitchens and bathrooms—each with its own laundry facilities. The home features 22 new windows, newer roof shingles, some new flooring, and has been freshly painted throughout the majority of the space. Enjoy outdoor living with a brand new front veranda (25.3 x 8.6) and a spacious back patio (17 x 10), complete with wheelchair access to the lower-level entrance, enhancing accessibility and functionality. Each unit is equipped with separate power meters, while heating costs are covered by the homeowner. The lower level has been used as an in-law suite (no rental income previously collected), offering flexibility for future use. While the home would benefit from some finishing touches, it is move-in ready and presents a fantastic opportunity for families or investors alike.

15 George Street, Middleton
$389,000
4 Beds ⋅ 2 Baths ⋅ 202607129 MLS
Charming, well-maintained bungalow on a quiet side street in the heart of Middleton, just steps from all downtown amenities and hitting the open market for the very first time after generations of loving care by the same family. The main floor impresses with bright, oversized rooms and a warm, inviting feel throughout. The large, south-facing living room is bathed in natural light and features a propane fireplace (2021), making it the perfect place to gather year-round. The XL primary bedroom offers a beautifully tiled ensuite bath with the added convenience of adjacent laundry. Hardwood and ceramic flooring flow throughout the home, complemented by recently updated vinyl casement windows in every room that keep things bright and energy efficient. The full-height basement is partially finished and offers excellent potential for additional living space, a rec room, or storage. The mechanicals are in great shape with a recent furnace (2018) and roof shingles (2014). Outside, the property is a true standout, with immaculate landscaping featuring terraced perennial beds, ornamental trees, and a large sun deck ideal for warm weather entertaining. The paved driveway leads to an impressive 34x32 double detached garage complete with a large separate workshop area, a rare find for hobbyists, contractors, or anyone needing serious storage and workspace. Garage roof shingles (2021). Municipal water and sewer. Appliances included. Full of character and available for quick occupancy.

21 Spring Garden Road, Middleton
$699,900
202606967 MLS
Can you envision yourself as a successful business owner? It’s time to make that dream a reality with this established and profitable restaurant situated in the heart of the growing Annapolis Valley! Constructed in 2012, quality craftsmanship and a unique design make for great venue for casual dining and small events, this is a popular destination for company Christmas parties, travellers and loyal locals looking for a tasty home cooked meal. Plenty of parking space and room for expansion, the zoning and eight-acre lot permits for a multitude of uses and direct access to the “rail to trail” system brings in yet another client demographic. Guests have a choice of patio dining or interior booths & tables and can enjoy a beverage being fully licensed complete with bar area. The impressive vaulted ceiling and abundance of windows pairs well with the easy-care tile flooring and cozy in floor heating. Fully equipped commercial kitchen with multiple prep and storage areas and a long list inventory and up to date equipment means you can get started and whip up your latest creation in no time! Wheelchair accessible, two large public washrooms + staff washroom, air conditioning via heat pumps and municipal water & sewer. This exclusive opportunity could be just what you’re looking for!

71 Main Street, Middleton
$349,500
4 Beds ⋅ 2 Baths ⋅ 202604716 MLS
From the lush established gardens, to the storybook exterior. This gem of a property in Middleton will make you do a double take! Known as the “Heart of the Valley”, this quaint town offers a variety of shops and services, and a new medical clinic and Soldiers Memorial Hospital are within a 2-minute walk. Plenty of paved parking space and a true double car garage are both a nice touch. Thoughtfully designed perennial gardens adorn the front and back yards, creating a whimsical environment full of blooms and fragrances for you to enjoy! Not to worry, the interior is just as inviting! Flooded with natural light from the many windows and skylights, this home is move in ready with fresh paint throughout the main floor and is also available for immediate occupancy. The large custom kitchen offers an abundance of solid oak cabinetry and a cozy dining nook overlooking the park like backyard. Arched entry’s, hardwood floors, and a couple of vintage touches gives this home personality and character. The large sunny living room opens onto the formal dining room, and two bedrooms on the second level are each a good size and have lots of storage space. A main floor bedroom and den with easy access to the full bath is followed by a finished basement. Complete with a family room, fourth bedroom, second full bath, laundry, and workshop area with walk up to the backyard. Always well maintained with plenty of updates both inside and out, and a newer quality ductless heat pump with remaining transferable warranty will keep your utility bills in line. This attractive property is full of pleasant surprises, and deserves consideration on your home hunting search!

480 Main Street, Middleton
$379,888
3 Beds ⋅ 2 Baths ⋅ 202601166 MLS
A unique home to begin the journey of home ownership. The perfect house for a single person or a couple starting a family. This 3 bedroom 1.5 bath 2 Storey is nestled into 3 acres offering an ecosystem all on it's own, several species of birds nesting on the property, white tailed deer meandering quietly through the acreage, and mature trees providing a park like environment. Within walking distance to all of Middleton’s many amenities. Located in a quiet subdivision and approved for a secondary dwelling with plenty of room to build an in-law suite. An extensive upgrades list within the last 2 years including a completely refurbished kitchen including maple butcher block countertops, shiplap feature walls, farmhouse apron sink, cabinets and flooring, a 2 pc. Powder room on main level, birch hardwood flooring, light fixtures, basement stairs, all cast iron plumbing replaced and all PEX plumbing installed, refurbished 2nd level 4pc. Bath, fresh paint, drywall on main level, side porch stairs and steps off of back deck installed, chain link fencing. There’s room to develop in the basement, 100 amp breaker panel, all vinyl windows, and a 12x16 shed with workbench. 15 min to 14 Wing Greenwood, 1.5 hr to Halifax and 1 hr to the South Shore.

3 Reagh Avenue, Middleton
$284,900
202526548 MLS
Exceptional opportunity to own a highly visible 3-unit commercial building in the heart of Middleton’s business district. This well-maintained property offers strong income potential with long-term tenants and room to expand. The ground floor features two established businesses, a popular pizza shop and a busy hair salon, both with many years of successful operation. The third main-level unit is currently owner-occupied as an office space, offering flexibility for continued use or rental income. Upstairs, the spacious upper level has been completely gutted and is ready for development, ideal for additional office suites or conversion into residential apartments. There is also two small offices upstairs and a half bath, with potential for many more spaces. A new carrying beam has already been installed, making the renovation process easier for the next owner. The building is efficiently heated and cooled with a ducted heat pump system. Ample deeded parking is available for tenants and customers, along with a convenient storage shed at the rear of the property. With excellent Main Street exposure, strong existing tenants, and untapped potential for additional income, this property presents a rare investment opportunity in a prime location.

284 Main Street, Middleton
$499,900
6 Beds ⋅ 202421333 MLS
This recently renovated Triplex is a fabulous investment opportunity! The recent renovations include all new windows,siding and insulation behind it, some new flooring,hardwood refinished, all units painted, the electrical was inspected with new light switches and plugs installed, as well as new hot water baseboards. Every unit has been inspected. The property boasts one 1-bedroom unit, one 2-bedroom unit, and one 3-bedroom unit, with the potential for a fourth unit. Fixed term leases in place. Apt 1 $2300/month til June/26 includes utilities. Apt 2 at $1600/month, fixed term til May/26, includes heat, hot water, electricity.Apt 3 $1700/ month til May/26 includes utilities. Whether you are looking for an investment property or adding to your portfolio, this is a rare opportunity that won't last long!

199 Main Street, Middleton