Middleton
Middleton homes for sale, nearby amenities, rural acreage, close to highway access
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71 Main Street in Middleton: Annapolis County Commercial for sale (Annapolis Valley) : MLS®# 202606967
71 Main Street Middleton B0S 1P0 
$650,000Commercial- Status:
- Active
- MLS® Num:
- 202606967
- Major Bus.:
- Restaurant
- Floor Area:
- 3,800 sq. ft.
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! More detailsListed by RE/MAX Banner Real Estate(Greenwood)- ANDREA JONES
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199 Main Street in Middleton: Annapolis County Multi-Family for sale (Annapolis Valley) : MLS®# 202421333
199 Main Street Middleton B0S 1P0
$499,900Multi-Family- Status:
- Active
- MLS® Num:
- 202421333
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 $2200/month til March31st/27 includes utilities. Apt 2 at $1600/month, fixed term til Feb.28/27, includes heat, hot water, electricity.Apt 3 $1700/ month til April 30/27 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! More detailsListed by RE/MAX Advantage- ANDREA JONES
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383 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202625284
383 Main Street Middleton B0S 0B2
$475,000Residential- Status:
- Active
- MLS® Num:
- 202625284
- Bedrooms:
- 5
- Bathrooms:
- 2
- Floor Area:
- 2,905 sq. ft.
Step back in time and appreciate the craftsmanship of a well-maintained century home. Have you been looking for a spacious home in Middleton with loads of flexibility, high ceilings, a kitchen for anyone who loves to cook, and a garage with a built-in workshop? Then you're in luck! Welcome to 383 Main St., Middleton - a 1905 home built by the Rogers family, once the workplace of a local doctor, and later home to the owner of the local creamery and Middleton's Mayor McKenzie, whose distinctive "M" is still carved into the window shutters today. Whether you're admiring the fine woodworking on the banisters, the hardwood floors, the cosy woodstove in the living room that has kept families warm for decades, or the attic space that's ready to be finished, this home offers both move-in-ready living and the potential to add your own creative touches. This five-bedroom, 1.5-bathroom home will not disappoint. The main floor offers plenty of living space; a large kitchen with breakfast nook, formal dining room, living room, den, half bath, and sunroom. Upstairs you'll find three generous bedrooms at the front of the home, a full 4-piece bathroom with double sink, two additional bedrooms, and a second staircase. The home is heated by wood and oil. The garage offers room for vehicles and storage, plus a permanent workshop with built-in workbenches along the entire back half of one side. Outside, enjoy a covered porch, ample parking, and a partially fenced yard with the opportunity to fence in more. Close to all of Middleton's amenities! Reach out to your agent of choice to see this piece of Middleton history. More detailsListed by Exit Realty Town & Country- ANDREA JONES
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10 Connaught Ave Avenue in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202612514
10 Connaught Ave Avenue Middleton B0S 1P0
$449,900Residential- Status:
- Active
- MLS® Num:
- 202612514
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 3,013 sq. ft.
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. More detailsListed by Royal LePage Atlantic (New Minas)- ANDREA JONES
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397 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202623756
397 Main Street Middleton B0S 1P0
$449,000Residential- Status:
- Active
- MLS® Num:
- 202623756
- Bedrooms:
- 2
- Bathrooms:
- 1
- Floor Area:
- 1,120 sq. ft.
Welcome to this beautifully designed new construction home, offering modern comfort and easy living all on one level. This charming 2-bedroom, 1-bathroom home features an inviting open-concept layout with impressive cathedral ceilings that create a bright and spacious feel a very generous kitchen , mudd room with laundry The home offers low-maintenance living 3 heat pumps an attached garage for added convenience. Step outside to enjoy your covered front veranda, perfect for your morning coffee, or head to the back deck for relaxing evenings and summer entertaining. With quality new construction, thoughtful design, and plenty of outdoor space to enjoy, this home is an excellent opportunity for first-time buyers and downsizes. With town water and sewer and walking distance to shopping and hospital this is the perfect package . Just picture that 12 foot christmas tree with those cathedral ceilings ..New Home warranty included More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
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145 Commercial Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202614539
145 Commercial Street Middleton B0P 1S0
$444,900Residential- Status:
- Active
- MLS® Num:
- 202614539
- Bedrooms:
- 4
- Bathrooms:
- 3
- Floor Area:
- 3,192 sq. ft.
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. More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
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366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202620079
366 Main Street Middleton B0S 1P0
$425,000Residential- Status:
- Active
- MLS® Num:
- 202620079
- Bedrooms:
- 6
- Bathrooms:
- 3
- Floor Area:
- 2,672 sq. ft.
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! More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
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27 Pinecrest Drive in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202622113
27 Pinecrest Drive Middleton B0S 1P0
$425,000Residential- Status:
- Active
- MLS® Num:
- 202622113
- Bedrooms:
- 4
- Bathrooms:
- 3
- Floor Area:
- 2,104 sq. ft.
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! More detailsListed by RE/MAX Banner Real Estate(Greenwood)- ANDREA JONES
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61 Connaught Avenue in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202622418
61 Connaught Avenue Middleton B0S 1P0
$399,900Residential- Status:
- Active
- MLS® Num:
- 202622418
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 2,200 sq. ft.
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! More detailsListed by RE/MAX Banner Real Estate(Greenwood)- ANDREA JONES
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6982645
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68 Connaught Avenue in Middleton: Annapolis County Multi-Family for sale (Annapolis Valley) : MLS®# 202615765
68 Connaught Avenue Middleton B0S 1P0
$369,900Multi-Family- Status:
- Active
- MLS® Num:
- 202615765
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. Upstairs unit is now vacant and has been thoughtfully refreshed with new floorings and painted throughout. 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. 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! More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6982645
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-
68 Connaught Avenue in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202618895
68 Connaught Avenue Middleton B0S 1P0
$369,900Residential- Status:
- Active
- MLS® Num:
- 202618895
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 2,200 sq. ft.
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. Upstairs unit is now vacant and has been thoughtfully refreshed with new floorings and painted throughout. 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. 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! More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6982645
- Contact by Email
-
3 Reagh Avenue in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202601166
3 Reagh Avenue Middleton B0S 1P0
$359,000Residential- Status:
- Active
- MLS® Num:
- 202601166
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,085 sq. ft.
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. More detailsListed by RE/MAX Banner Real Estate(Greenwood)- ANDREA JONES
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6982645
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Data was last updated October 15, 2026 at 09:20 AM (UTC)
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