Middleton Real Estate | Middleton Homes for Sale

6 Beds ⋅ 202622666 MLS

A great opportunity for investors looking to add a solid income-producing property to their portfolio. This triplex features three spacious two-bedroom units, all currently rented at $1,300/month (includes heat), providing immediate rental income from day one. Each unit offers two bedrooms and comfortable living space, with two units heated by oil furnaces and one by heat pump. The property is being sold as is, offering an opportunity for the next owner to build on its existing income and long-term potential. Located right in the heart of Middleton, this property is within easy reach of local amenities, schools, shopping, restaurants, parks and more. With three occupied units and established rental income, this is an excellent opportunity for both experienced investors and those looking to get started in multi-unit ownership. Three units. $3,900/month in current rental income. Great location. Immediate possession. Don’t miss your opportunity to own an income-producing triplex in the welcoming community of Middleton!

6-10 George Street, Middleton

$399,900

3 Beds ⋅ 2 Baths ⋅ 202622418 MLS

61 Connaught Avenue, the sweetest house on the block! All of the heavy lifting is done here with an impressive upgrades list that will please the most discerning buyer. Classic Cape Cod style with so many modern touches. Beautifully situated on one of the most peaceful low traffic streets in Middleton. Within walking distance to all of the many amenities and schools, including pub, restaurants, shopping, hospital and so much more. A spacious foyer begins the main level tour with a gorgeous eye catching color palette. A 2 storey addition provides an extra family room offering sound division and play area for the busy family. 2 pc. powder room, a completely refurbished kitchen with loads of shaker style cabinetry, formal dining room, and an attractive living room for entertaining. Energy efficient heat pumps throughout the home equal low heating costs! 2nd level boasts a refurbished 4 pc. family bath, a huge primary bedroom (new addition) and 2 more good sized family/guest bedrooms. Let's not forget about the Staycation back yard oasis with a massive above ground pool, expansive decking, and privacy fencing, just the ideal spot to relax with friends and family. A meticulously landscaped lot with mature trees and shrubs just add to the charm! 1.5 hour drive to Halifax, 15 min. to 14 Wing Greenwood and 45 min to Acadia University in Wolfville. True value and comfort in this turn key property, come and check it out!

61 Connaught Avenue, Middleton

$439,900

4 Beds ⋅ 3 Baths ⋅ 202622113 MLS

First time on market! 27 Pinecrest Drive has been in the same family since it was built in 1995, and the care shows in every corner. This is the sort of community people move into and never want to leave, quiet and established, where the trees have grown up alongside the families and neighbours still wave from the driveway. Walking distance to all amenities and under 15 min to CFB Greenwood. The 2-storey layout offers 3 bedrooms above grade, a 4th bedroom on the lower level, 2 full baths plus a half bath, and a generous ensuite off the primary. The full height basement was finished in 2006 with a family room and bonus bedroom, and also offers a large storage room and mechanical room, offering plenty of space for a growing family, a home office, or extended family living. The kitchen was renovated in 2018, and fresh paint carries through two floors. Mechanically sound: roof shingles recently replaced (2018), two heat pumps (2016 and 2024, both serviced June 2026), an oil furnace on three zones (serviced in 2025), a new oil tank (2025), and Venmar air exchanger (2013), and more. Fully fenced lot featuring a paved driveway (circa 2012), single attached garage, and a hot tub (2020) that stays. Backing onto town-owned green space with stone's-throw access to trails and rec facilities. Fibre internet and a security system are already in place, appliances are included, and many chattels are negotiable. Priced to sell and 100% move-in ready!

27 Pinecrest Drive, Middleton

$299,000

4 Beds ⋅ 2 Baths ⋅ 202621286 MLS

Welcome to this charming 4 bedroom + 1 apartment century home in the heart of Middleton! The home features a bachelor apartment in the back, providing an excellent opportunity for rental income, extended family, or a mortgage helper. The front portion of the home is currently vacant and ready for immediate possession, while the back apartment is occupied by a tenant. Offering character, convenience, and potential, this property sits on a generous lot within walking distance to schools, shopping, restaurants, parks, and all the amenities the town has to offer. Recent updates and improvements include fresh paint, new flooring, a new toilet, new door, new fridge, and new smoke detectors. The electrical was rewired in 2003, the furnace has just been serviced, and the chimney has recently been cleaned, giving you added peace of mind. Outside, you'll find a large lot and single-car garage, offering plenty of space for parking, storage, gardening, or enjoying the outdoors. All of this on town water and sewer! Whether you're looking for your first home, an investment property, or a character-filled home with income potential, this Middleton property is worth a look. Vacant front portion + tenant in the back = immediate opportunity!

20 Queen Street, Middleton

$270,000

202620932 MLS

Welcome to your next investment opportunity in the heart of Middleton. Offering high exposure and high visibility, this well-located commercial property is perfectly positioned for your next business venture. Previously operated as a café/bistro, the space is well-suited for food service or a variety of other commercial possibilities. Adding even more value are 2 residential opportunities, one two bedroom unit above the main commercial space and another adjoining one bedroom unit— creating excellent potential for rental income or a live-work setup. There is an additional residential building, however the condition is unsafe and requires immediate repair. With ample on-site parking and strong street presence, this property offers convenience for both customers and tenants alike. Whether you're an investor looking to expand your portfolio or an entrepreneur ready to bring your vision to life, this property is packed with potential. Being sold as is, where is, with no warranties or guarantees. Don’t miss your chance to secure a versatile, income-generating property in a prime Middleton location.

296-300 Main Street, Middleton

$299,900

2 Beds ⋅ 1 Baths ⋅ 202620588 MLS

Cute, comfortable and surprisingly complete, this charming one-level home on Sunset Crescent in Middleton is proof that good things really can come in small packages. Inside, the 578 sq. ft. layout is bright, welcoming and thoughtfully designed, with two bedrooms, full bath and inviting living spaces that make excellent use of every inch. The beautifully landscaped yard offers plenty of space to relax or entertain with a deck, gazebo and shed, plus an adorable 10' x 10' bunkie with all kinds of possibilities — home office, hobby room, creative studio, reading retreat or a little getaway of your own. The property has also seen plenty of love and improvements over the past year, including new vinyl siding, paved driveway, painted fence, new sump pump and a new hot water tank. Located on municipal services, this little cutie offers easy living, minimal maintenance and a backyard that's anything but boring. Small footprint. Big personality. And one very cute place to call home! Come see this little gem for yourself.

130 Sunset Crescent, Middleton

$370,000

4 Beds ⋅ 2 Baths ⋅ 202620271 MLS

Welcome to 1 Mckenzie Drive in Middleton, a move-in-ready split-entry style home offering a flexible layout, drive-in garage, fenced backyard and a welcoming covered porch that adds charm to the home’s exterior. The main level features three bedrooms and a three-piece bath, along with bright, open-concept living areas that provide an easy flow for everyday living and entertaining. The kitchen offers plenty of storage with an attached pantry area that could also serve as an eat-in kitchen space. From here, walk directly out to the private and secure patio, a great spot for morning coffee, summer meals or relaxing outdoors. The lower level adds plenty of versatility with a large recreation room, kitchenette, three-piece bathroom and additional space with potential for another bedroom. A separate entrance provides direct access to the backyard, while the drive-in single garage also offers convenient access to the lower level. This flexible space could work well for extended or multi-generational family living, guests, or those exploring potential investment possibilities.Outside, a large portion of the backyard is fenced, providing a secure space for children, pets or outdoor enjoyment. A newly constructed backyard storage/workshop area adds even more appeal with dedicated space for projects, hobbies, tools and storage and recent updates including new windows and blown in insulation plus existing generator panel add even more value. Serviced by municipal water and sewer and conveniently located near Middleton’s amenities, including Soldiers Memorial Hospital, with a quick commute to CFB Greenwood, 1 Mckenzie Drive offers a great combination of space, versatility and convenience for its next owner.

1 Mckenzie Drive, Middleton

$425,000

6 Beds ⋅ 3 Baths ⋅ 202620079 MLS

Town convenience with room for everyone! This spacious 6-bedroom home offers the perfect mix of timeless character and modern efficiency, all within walking distance to shopping, restaurants, schools, parks, and everyday amenities. Inside, you'll appreciate the original charm that has been carefully preserved while major updates have modernized the home for comfortable family living. The bright, open-concept living and dining area stretches across the front of the home, with easy access to the inviting front veranda. The renovated kitchen is both stylish and functional, featuring custom countertops, abundant cabinetry, a built-in wine rack & coffee bar plus included appliances. The flexible layout offers six bedrooms, making it ideal for large families, multi-generational living, or those working from home. Upstairs, three unique bedrooms showcase original softwood floors and share a 3-piece bath. The main level features three additional bedrooms, including an impressive primary suite complete with a massive walk-in closet and a beautifully finished ensuite featuring a freestanding soaker tub and walk-in glass and tile shower. A third full bathroom includes laundry hookups, with the washer and dryer remaining, while the practical rear mudroom provides the perfect everyday entry. Designed with efficiency in mind, the home has been upgraded with a 200-amp electrical service, four ductless heat pumps, a professionally installed solar system, and a cozy propane fireplace. A full basement provides excellent storage space for seasonal items and hobbies. Situated on a large, level lot in the Residential Mixed Zone, this property offers exciting potential for a variety of home-based businesses, professional services, or retail opportunities, making it as versatile as it is spacious. Whether you're looking for a family home with room to grow or a property that combines residential comfort with business potential, this one is ready to impress!

366 Main Street, Middleton

$249,900

202619749 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

$369,900

4 Beds ⋅ 2 Baths ⋅ 202618895 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

$369,900

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

$324,900

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 Road, 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

$49,900

202613556 MLS

This lot is zoned Commercial downtown. There is a large structure on the lot that is in disrepair. Before entering the structure, all parties must sign a waiver found in the documents tab. Commercial downtown zoning allows for a variety of opportunities. Value is in the land

5 George Street, Middleton

$465,000

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

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