Middleton
Middleton homes for sale, nearby amenities, rural acreage, close to highway access
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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. Recent fixed term leases in place. Apt 1 $2100/month til April30/25 includes utilities. Apt 2 at $1600/month, fixed term til March 2025, includes heat, hot water, electricity.Apt 3 $1700/ month til March 31/25 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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366 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202523855
366 Main Street Middleton B0S 1P0
$465,000Residential- Status:
- Active
- MLS® Num:
- 202523855
- Bedrooms:
- 5
- Bathrooms:
- 3
- Floor Area:
- 2,225 sq. ft.
Find the lifestyle you have been looking for on Main Street in Middleton. 5 bedroom pls den 3 bath renovated period infused character home on municipal services, enjoying numerous updates while maintaining the features and feel of the early 1900s. Welcoming 45’ front verandah brings you in and the main living area is open, 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 fanciful windows are serviced by a full bath. Situated on almost a half acre in the center of Middleton enjoy that walkable lifestyle you have been dreaming about with amenities from dining, shopping, groceries, schools and more mere minutes or less away. Don’t think hustle and bustle think charming and quaint. Solar to be paid out, appliances all 2 years old, windows and entry doors are new, basement spray foamed. Close to the NSCC campus or under 15 to CFB Greenwood. You can live your best life in the beating heart of the Annapolis Valley. More detailsListed by Engel & Volkers- ANDREA JONES
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145 Commercial Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202510747
145 Commercial Street Middleton B0P 1S0
$424,900Residential- Status:
- Active
- MLS® Num:
- 202510747
- Bedrooms:
- 4
- Bathrooms:
- 3
- Floor Area:
- 3,192 sq. ft.
Step into this beautifully renovated century home, perfectly situated in the heart of the Annapolis Valley. The main level boasts a stylish open-concept layout with spacious dining and living areas with a cozy new wood stove, ideal for gathering with family and friends. Comfy sitting room and a bright sun porch offer peaceful spaces to relax and unwind. A full bath with a luxurious soaker tub completes the main floor. Upstairs, you’ll find four sunny and generously sized bedrooms, including a primary suite with its own en suite bath. An additional full bathroom serves the remaining bedrooms, along with a spacious laundry area complete with built-in storage for added convenience. Charming original staircases, authentic trim, and custom details add timeless character throughout the home. The upper loft provides a versatile space perfect for a home office, guest area, or a cozy retreat. Step outside to a tranquil, fully fenced backyard featuring a large deck, beautifully landscaped gardens, and a separate workshop—an ideal setting for both relaxation and creativity. With its rare commercial zoning, this property offers unique investment potential, making it perfect for a home-based business or dual-purpose living and the numerous list of home improvements make this home movein ready. Don’t miss this opportunity to own a true gem in the Annapolis Valley! More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
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3 Reagh Avenue in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202511270
3 Reagh Avenue Middleton B0S 1P0
$399,000Residential- Status:
- Active
- MLS® Num:
- 202511270
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,200 sq. ft.
3 ACRES IN TOWN!!! Welcome home to 3 Reagh Avenue! Approval for a secondary dwelling is an option. Located in an established peaceful subdivision this 3 bedroom abode is situated on a private park-like acreage with mature trees, shrubs and perennials. This home has been extensively renovated with upgrades including a brand new kitchen with gorgeous maple butcher block countertops and shelving, shiplap accent wall, farmhouse apron sink, and breakfast bar island, new 2pc. bath. Main level has new drywall, freshly painted, new flooring in kitchen, gleaming birch hardwood throughout, and all new window treatments. Entire house re-plumbed including replacing original cast iron plumbing. New breaker panel, new front steps/deck, new steps on back deck. Refurbished 4pc. bathroom with new flooring, toilet replaced, vessel sink and new maple vanity top. 1800 sq ft of living space in total with room to develop in the basement. All vinyl windows, new basement stairs, new light fixtures, new chain link fence ideal for pets and kids! Walk to NSCC campus, and all amenities including elementary, middle and high schools, hospital, shopping, restaurants, pub, and coffee shops. Municipal services and a 12 x 16 shed with workbench. 15 min to 14 Wing Greenwood, 45 min. to Wolfville, and 1.5 hr to Halifax. An ideal location for family life!!! More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
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480 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202516089
480 Main Street Middleton B0S 1P0
$364,900Residential- Status:
- Active
- MLS® Num:
- 202516089
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 2,214 sq. ft.
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! More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
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419 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202523707
419 Main Street Middleton B0S 1M0
$350,000Residential- Status:
- Active
- MLS® Num:
- 202523707
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,344 sq. ft.
Welcome Home! You won't want to miss out on this charming 3 bedroom, 1 and a half bath home, sitting centrally in the heart of Middleton on an oversized lot. Move in and relax, there's nothing for you to do in this home, except add your own personal touches, of course! Walk into a large mud/laundry room and then into the kitchen. The kitchen leads you to a spacious dining room, which opens into the living room with beautiful French doors and gleaming hardwood floors! Upstairs, you'll find three large bedrooms and a full bath. Walk outside to the well-manicured yard, paved drive and parking spaces, and a large outbuilding for your tools, cars, and toys. More space follows to the back and is a blank canvas for you to develop as you wish by clearing and/or adding more gardens to create a quiet retreat to relax after work, or an extended space for your children and/or pets to run and play. Some recent updates include, but are not limited to: the roof was re-shingled in 2022, the oil tank was replaced in 2020, and the hot water heater was replaced in 2020. This home is full of character and charm and has RMU zoning. It is conveniently located moments from all the amenities Middleton has to offer, including shopping, the hospital, schools, parks, walking trails, the public outdoor pool, and much more! Or jump in your car for a quick trip into Kingston or CFB Greenwood. Don't delay on this one. More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
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1 Pinecrest Drive in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202520110
1 Pinecrest Drive Middleton B0S 1P0
$329,900Residential- Status:
- Active
- MLS® Num:
- 202520110
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 1,080 sq. ft.
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. More detailsListed by RE/MAX Banner Real Estate- ANDREA JONES
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437 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202519351
437 Main Street Middleton B0P 1M0
$309,900Residential- Status:
- Active
- MLS® Num:
- 202519351
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 1,350 sq. ft.
Curb appeal galore in this attractive centrally located bungalow on pretty treed lot. Lovely front verandah and spacious back deck are great for entertaining family and friends. Complete renovation about 15 years ago included siding, windows, doors, shingles, beautiful kitchen and renovated bath. Open concept dining/living room. Lower level is insulated plus drywalled exterior walls. There is an outside entrance for added convenience. Lots of room for you to add a family room and 4th bedroom. Let your imagination be your guide. Fridge, stove, washer, dryer and two sheds are included. The home is in a great location, walking distance to Soldiers Memorial Hospital and Middleton amenities. Come check it out and make this your new Valley home! More detailsListed by RE/MAX Banner Real Estate- ANDREA JONES
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188 Main Street in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202522073
188 Main Street Middleton B0S 1P0
$299,900Residential- Status:
- Active
- MLS® Num:
- 202522073
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 2,349 sq. ft.
Step into timeless charm with this sweet century home, perfectly located in the heart of Middleton. With all the town’s amenities just a short walk away, convenience meets character in this one-of-a-kind property. Inside, you’ll find 4 bedrooms, 2 bathrooms, and a thoughtful blend of original features with modern upgrades. A unique highlight is the second kitchen upstairs with a separate entrance—offering excellent rental potential or a flexible in-law suite option. The main dining room boasts a distinctive built-in bar, perfect for entertaining, and not something you see everyday! Recent upgrades include 4 efficient heat pumps, an electrical upgrade to a 200 AMP (2022), new wall heaters and smoke detectors , new roof (2022), and a cozy woodstove (2024), ensuring comfort and peace of mind. Outside, enjoy a back deck, small fenced area for pets, and a handy storage shed. With its character, updates, and income potential, this home truly has it all! Come take a look! * Motivated Sellers* More detailsListed by Royal LePage Atlantic (Greenwood)- ANDREA JONES
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284 Main Street in Middleton: Annapolis County Commercial for sale (Annapolis Valley) : MLS®# 202526548
284 Main Street Middleton B0S 1P0
$299,900Commercial- Status:
- Active
- MLS® Num:
- 202526548
- Major Bus.:
- Other
- Floor Area:
- 5,982 sq. ft.
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. More detailsListed by RE/MAX Banner Real Estate- ANDREA JONES
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202 Main Street in Middleton: Annapolis County Commercial for sale (Annapolis Valley) : MLS®# 202516130
202 Main Street Middleton B0S 1P0
$299,000Commercial- Status:
- Active
- MLS® Num:
- 202516130
- Major Bus.:
- Other
- Floor Area:
- 6,494 sq. ft.
St. John's United Church is on the market for the first time ever and offers an expansive 6500+/- square foot two level structure with huge potential for a variety of future uses. The building is currently zoned Institutional and buyers are advised to verify zoning suitability for any intended purpose with the Town. This unique property could lend itself well to a wide range of possibilities including conversion to housing units, commercial ventures like a restaurant or retail space, or continued institutional use as a church, performance venue or community hall. The main level features an enormous vaulted sanctuary with balcony seating while the lower level offers a large reception hall with two kitchens plus multiple bathrooms and additional rooms and office areas for flexible use. Municipal water and sewer services are in place. Property is being sold as is where is with no warranties or representations from the seller. Many chattels are negotiable and can be discussed as part of any offer. This is a rare opportunity to purchase a large and versatile structure with a long local history and endless future potential. More detailsListed by RE/MAX Banner Real Estate- ANDREA JONES
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3 20 Connaught Avenue in Middleton: Annapolis County Residential for sale (Annapolis Valley) : MLS®# 202521319
3 20 Connaught Avenue Middleton B0S 1P0
$289,000Residential- Status:
- Active
- MLS® Num:
- 202521319
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 2,052 sq. ft.
Offering a wonderful opportunity to own a spacious condo townhouse in the heart of Middleton, situated on a quiet street. With 3bedrooms, 2.5 baths, and laundry facilities conveniently located on the upper or the lower level, this condo offers both comfort and practicality. The lower level features a generous family room which provides direct walk-out access to grade & a decent size storage room. The unit is complete with a balcony, a cozy fireplace and 2 heat pumps, making it ready for you to move in and start enjoying the comfortable lifestyle it offers. Meticulously maintained, this property is priced to sell ensuring exceptional value for prospective buyers. As a resident, you will also have shared access to the beautiful grounds which have frontage on the scenic Annapolis River, providing a lovely setting for outdoor activities and relaxation. Furthermore, the affordable monthly condo fee of only $450 covers exterior maintenance, snow removal, grounds keeping, and municipal water, granting you peace of mind and a worry-free living experience. More detailsListed by ViewPoint Realty Services Inc.(Greenwood)- ANDREA JONES
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Data was last updated November 7, 2025 at 01:20 AM (UTC)
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