Midland Real Estate | Midland 5 Bedroom Properties for Sale

Located in the highly desirable West End, this all-brick bungalow offers the perfect blend of comfort, space, and outdoor living. Featuring 3+2 bedrooms and 3 bathrooms, the home boasts a large main floor primary suite complete with a private ensuite, along with spacious principal rooms including a bright kitchen, living room, and a cozy family room with a gas fireplace. Engineered hardwood flooring runs throughout the main level, adding warmth and style. The fully finished basement extends your living space with a generous rec room (complete with pool table), plus an additional office or craft room. Step outside to your private backyard oasis featuring a 16x32 inground pool with a new liner (2024), a 6-person hot tub with new cover, screened gazebo, cedar planters, and an irrigation system-all fully fenced for privacy. Additional highlights include new gutter guards, central vac, and a Generlink for added peace of mind.

933 Playfair Road, Midland

$1,149,000

5 Beds ⋅ 2 Baths ⋅ S13741086 MLS

Welcome to the highly sought-after Midland Point community. This just under half acre lot has backyard access to the waterfront trail and Georgian Bay (Gawley Park), where you can enjoy the sandy beach and all your favourite water activities. This beautifully updated 5-bedroom, 2-bathroom home offers exceptional space, modern finishes, and a warm lakeside-inspired feel. Recent updates include new flooring throughout, a beautifully remodeled upper bathroom, new front and rear decks, new driveway and hot tub (2024), and numerous additional improvements, creating a move-in-ready home. The spacious layout provides room for growing families, guests, or those working from home. Outside, enjoy an attached double-car garage, a newly paved driveway with ample parking, and an impressive 24' x 24' heated and insulated detached workshop-perfect for hobbyists, storage, or a home business. This property combines stylish updates, versatile living space, and an exceptional lifestyle close to parks, trails, marinas, downhill and cross-country skiing and all the amenities Midland has to offer.

469 Parkview Court, Midland

$644,900

5 Beds ⋅ 3 Baths ⋅ S13731656 MLS

***Legal Duplex with Vacant Possession or the Perfect Multigenerational Set Up!*** Opportunities like this in Midland's sought-after west end are incredibly rare! This spacious and versatile LEGAL duplex offers the perfect setup for multi-generational living, owner-occupied investing, or adding a strong income property to your portfolio. The main floor features over 1,300 square feet of living space with a massive living and dining area, 3 generous bedrooms, and 2 bathrooms, including a spacious primary bedroom complete with its own 2-piece ensuite and incredible closet space. The lower level has been transformed into a new and fully legal secondary suite with its own separate entrance, separate 2 car driveway, in-suite laundry, 2 bedrooms, a full bathroom, and an impressive living space that truly feels like its own home. Step outside and the value continues with a fully fenced backyard designed for entertaining and relaxation. Enjoy the large inground pool, pool house for additional storage, and the covered deck with hot tub area that creates the ultimate outdoor retreat. Whether you're looking for a vacant investment property, mortgage helper, or a home that comfortably accommodates extended family, this property checks all the boxes while being located close to schools, parks, shopping, GBGH, and all of Midland's amenities. BUYER NOTES: Brand New Furnace June 2026 | Belanger Roof: Lifetime Warranty | Central A/C 2022 | 225 Amp Breaker Panel (no separate service) | Irrigation System | PERMITS ARE CLOSED: Legal Basement Apartment is a New Build Out (Kitchen, Flooring, Drywall, Lighting, Paint, Trim, Bathroom, Plumbing, Duct Work | Dishwasher 2025 | Washer and Dryer 2024 | Pool Liner 2024

958 Montreal Street, Midland

$649,900

5 Beds ⋅ 3 Baths ⋅ S13702204 MLS

Step into the timeless charm of this beautifully maintained century home, offering the perfect blend of character, comfort, and versatility. Lovingly cared for and in excellent condition, this inviting property showcases thoughtful updates throughout, including updated windows, electrical, roof, and bathrooms, providing peace of mind while preserving its historic appeal.The spacious and functional layout features three bedrooms on the second level, along with a dedicated home office ideal for remote work, study, or creative pursuits. The finished third floor adds exceptional flexibility with two additional rooms that can serve as extra bedrooms, guest accommodations, hobby spaces, a playroom, fitness area, or whatever suits your lifestyle.Outside, you'll find a beautifully landscaped and private in-town lot, creating a serene setting for relaxation and entertaining. Mature plantings and attractive outdoor spaces enhance the property's curb appeal while offering a rare sense of privacy within walking distance of local amenities.A wonderful opportunity to own a character-filled home with modern updates, flexible living space, and an exceptional in-town location.

238 Sixth Street, Midland

$1,999,000

5 Beds ⋅ 3 Baths ⋅ S13678340 MLS

A rare offering on Georgian Bay in Midland, just 90 minutes from the GTA: a private, deep-water lot with your own dock and full shoreline ownership rights - the kind of setting that doesn't come up often. Inside, the ceiling does the talking: 15 feet of vaulted shiplap and timber overhead, glass walls and the Bay filling the view from nearly any room. Slide the doors open and the composite deck becomes an extension of the living space, built for entertaining as much as for taking in the water.The main-floor primary suite is its own retreat - a walk-in closet, heated floors, a freestanding soaking tub, and a glass-enclosed shower, a beautifully designed spa-like escape. Downstairs runs warm on radiant in-floor heat, lit by floor-to-ceiling glass, and walks straight out to a landscaped, fenced yard that ends at the water's edge. This 2 + 3 bedroom home was built 8 years ago in an already established neighbourhood. A 608 sq ft garage adds generous storage and workspace beyond the everyday, and a Generac backup generator keeps the home fully powered year-round and brings peace-of-mind in our changing climate. Minutes to Midland's marinas and trail system - four-season waterfront living, done at the highest level with no well or septic to worry about, this home is on full municipal services. A simply beautiful property and a must see if you are looking for waterfront on Georgian Bay!

625 Aberdeen Boulevard, Midland

$684,000

5 Beds ⋅ 2 Baths ⋅ S13661712 MLS

Work, live, and thrive in one location! Walk-out bungalow with Highway Commercial zoning (residential permitted) offers endless possibilities for your new or existing business - or simply your great new home on a huge lot, with parking & room for all your toys. Massive 200 ft of frontage on a high-visibility road, parking for 20+ vehicles, oversized 2-car detached garage, this property is built for visibility and convenience. The upper-level 3-bedroom suite with a private deck that brings a touch of country living, while the lower-level is currently being used as a 2-bedroom retreat, complete with a private hot tub room. With HC zoning allowing a wide range of permitted uses, this is your chance to combine home, work, and investment in one incredible property. Don't miss it!

9467 County 93 Road, Midland

$609,900

5 Beds ⋅ 3 Baths ⋅ S13584838 MLS

Welcome to this beautifully maintained Colonial-style home, where timeless charm meets everyday comfort. Nestled in a desirable Midland neighbourhood, this spacious family home is within walking distance of both elementary and secondary schools, vibrant downtown Midland, and the beautiful shores of Georgian Bay. Offering four generously sized bedrooms on the upper level, it's ideal for growing families or those seeking dedicated home office space. The bright and inviting main floor features a functional open-concept layout, a formal dining room perfect for entertaining, and a well appointed kitchen with solid oak cabinetry. The quality oak cabinetry and vanities throughout the home add warmth, character, and lasting appeal. Enjoy your morning coffee on the front covered porch or unwind on the rear covered porch, extending your outdoor living space. The finished basement adds exceptional versatility with a large recreation room, a fifth bedroom, and a three-piece bathroom, making it ideal for guests, teenagers, or extended family. Additional highlights include ample private parking, shingles replaced approximately three years ago, and no rental items. Offering the perfect combination of space, functionality, classic style, and an unbeatable walkable location, this exceptional home is ready to welcome its next family.

255 Hanly Street, Midland

$575,000

5 Beds ⋅ 2 Baths ⋅ S13582610 MLS

Welcome to 645 Bayview Drive in the heart of Midland! This spacious and well-appointed 3+2 bedroom, 2 full bathroom home offers exceptional flexibility for families, multi-generational living, or savvy investors. The bright walkout basement features oversized windows, high ceilings, and excellent in-law suite potential, creating the ideal setup for extended family or future income possibilities. Enjoy a functional floor plan with generous principal rooms, plenty of natural light, and seamless access to outdoor living spaces. Conveniently located close to schools, shopping, restaurants, parks, beaches, marinas, and everyday amenities. Experience the best of Georgian Bay living with nearby waterfront trails, parks, and year-round recreation just minutes away. An incredible opportunity to enjoy comfort, lifestyle, and versatility in one of Simcoe County's sought-after waterfront communities.

645 Bayview Drive, Midland

$444,900

5 Beds ⋅ 3 Baths ⋅ S13532098 MLS

Attention Investors or First Time Home Buyers. Amazing Opportunity. Side by Side Duplex. Live in One Side and Rent Out the Other One. Or Rent Out Both. Legal Duplex! Municipal Address 642/644 Bay Street is a 50 x 150 Foot Lot with A Full Semi-Detached Structure Being Sold. 3 Kitchens, 3 Bathrooms, 5 Bedrooms. Parking on Both Sides of the Houses. Garage Converted to Storage with Man Door with Bonus Space Above. The Price is Well Worth the Drive to Midland! Huge Yard.

642-644 Bay Street, Midland

$699,900

5 Beds ⋅ 2 Baths ⋅ S13521206 MLS

Welcome To This Meticulously Maintained Home, Under The Same Ownership Since It Was Built. Nestled In A Highly Desirable, Family-Friendly Community, This Turnkey Property Offers The Perfect Blend Of Comfort, Pride Of Ownership & Convenient Living. Featuring 3+2 Bedrooms & 2 Full Bathrooms, The Home Showcases A Bright, Functional Layout With Spacious Living Areas, High Ceilings, & Plenty Of Natural Light Throughout. Thoughtfully Updated Over The Years, This Home Has Been Carefully Cared For Inside & Out, Allowing You To Simply Move In And Enjoy. Step Outside To A Large Backyard & Expansive Deck Perfect For Gatherings, Entertaining, Or Relaxing Outdoors. The Beautiful Brick Exterior Adds Timeless Curb Appeal & Lasting Value. Located Just Minutes From Georgian Bay, Parks, Schools, Trails, And Everyday Amenities, This Location Is Ideal For Those Seeking Both Lifestyle & Convenience, Along With Everything This Wonderful Community Has To Offer. A Rare Opportunity To Own A Well-Kept Home In An Excellent Area.

444 William Street, Midland

$1,250,000

5 Beds ⋅ 4 Baths ⋅ S13485884 MLS

Overlooking Georgian Bay, this spacious home offers beautiful water views from many rooms and comfortable family living in one of the area's most desirable communities. Featuring 4+1 bedrooms and 3+1 bathrooms, the home includes a primary suite with a walk-in closet and a 3-piece ensuite with a barrier-free shower. The main living area is anchored by a peninsula-style fireplace and framed by a floor-to-ceiling window topped with arched panes, filling the space with natural light and showcasing beautiful bay views. Step out from the dining area to a large, elevated deck featuring glass panel railings that provide uninterrupted views of the bay, an ideal space for entertaining or simply enjoying the remarkable Georgian Bay setting. The finished walkout lower level adds valuable living space with a rec room, additional bedroom, and bathroom, making it ideal for family and guests. Recent updates provide peace of mind, including new windows (2024/2025), new shingles (2025), a new furnace and A/C with heat pump (2023), a new water softener (2026) and a 220V EV charging outlet in the double attached garage. Hardwood flooring, granite countertops, and a spacious layout further enhance the home's appeal. Step outside and enjoy direct access to the Trans Canada Trail right behind the property, offering endless opportunities for walking, cycling, and exploring the area's natural beauty. Located just minutes from both Penetanguishene and Midland and approximately 90 minutes from the GTA, this property also provides convenient access to nearby parks, beaches, shopping, marinas, golf courses, live theatre, living history attractions, and everyday services. Whether you're seeking a year-round residence or a retreat in one of the region's most sought-after waterfront settings, this home offers an excellent opportunity to enjoy the Georgian Bay lifestyle.

14 Riverwalk Place, Midland

$749,900

5 Beds ⋅ 3 Baths ⋅ S13478830 MLS

Eliminate your commute, grow your business, and build equity-all from one address.Welcome to 390 King Street, a rare opportunity to live and work under one roof in the heart of Midland. Ideal for entrepreneurs, professionals, and small business owners, this unique property offers the flexibility to operate your business while enjoying the comfort of home.Character-filled and spacious, the property has been thoughtfully improved with a newer roof, upgraded electrical, added insulation, fresh paint, and updated lighting. Outside, enjoy a private backyard retreat featuring an in-ground pool with a new liner being installed soon and a patio perfect for relaxing or entertaining.Conveniently located close to downtown, shopping, restaurants, and marinas, this is a unique opportunity to invest in a property that supports both your lifestyle and your business.

390 King Street, Midland

$569,000

5 Beds ⋅ 2 Baths ⋅ S13469038 MLS

Welcome to 19 Ludlow St in Midland - a stunning, fully renovated home taken right down to the studs with quality craftsmanship and modern finishes throughout. This spacious bungalow offers 3 bedrooms on the main level plus an additional 2 bedrooms in the fully finished lower level, making it ideal for large families, multi-generational living, or investment potential. Featuring 2 beautifully updated bathrooms, a separate entrance to the basement, and convenient inside access from the garage to the home, this property offers both functionality and flexibility. Enjoy a bright open concept layout with brand new appliances, brand new windows, updated flooring, modern kitchens and bathrooms, and stylish finishes from top to bottom. Updated plumbing and all new wiring/panel. Every detail has been thoughtfully updated, offering true turnkey living and peace of mind. Located in a family-friendly neighbourhood close to schools, parks, shopping, and Georgian Bay amenities. A rare opportunity to own a beautifully rebuilt home with incredible space and versatility!

19 Ludlow Street, Midland

$399,990

5 Beds ⋅ 2 Baths ⋅ S13436614 MLS

Perfect investment live in and run your business from this property, many of the commercial elements done, perfect for any type of office, Insurance, Accountant, Real Estate Office, has front and rear entrances and is full Of Old Charm & Located In A High Traffic Area Downtown Midland, You'll Have No Issue With Visual Exposure Here On Midland Avenue! Currently Set Up As A Live In Residence, This Commercial Building Offers 1,570 Sq Ft, Wheel Chair Accessibility & Rear Parking. Ideal For Office Use, But Suitable For Retail As Well.

354 Midland Avenue, Midland

$645,000

5 Beds ⋅ 2 Baths ⋅ S13421928 MLS

Attention investors! Here is a rare, low-stress addition to your portfolio. Located in a desirable, high-demand neighborhood on Midland's west side, this exceptionally well-maintained duplex is completely optimized for independent tenant living. The property features two spacious units (a 3-bedroom upper unit and a 2-bedroom lower unit), each completely self-contained to minimize your landlord overhead.The smartest feature of this build? Absolutely everything is separate. Both units boast their own private driveways, separate hydro meters, independent gas furnaces, individual A/C units, dedicated hot water heaters, separate electrical panels, and in-suite laundry facilities.The grade-level entry lower unit is a bright, accessible space currently generating $1,400/month plus utilities. The expansive main-floor upper unit is currently vacant. With all appliances included and a structure built for minimal maintenance, you can sit back and collect immediate cash flow from day one!

679 Montreal Street, Midland

$525,000

5 Beds ⋅ 2 Baths ⋅ S13061040 MLS

Well-maintained Midland duplex , easy to rent and positive cash flow. Long-standing tenants who take evident care and upkeep of the property.Each unit offers a spacious and functional layout with a full kitchen, comfortable living area and in-suite laundry. Both units are currently rented on a month-to-month basis, providing flexibility for future adjustments.Current rental income:Upper unit: 3 bedrooms, $1,835.13/month. Lower unit: 2 bedroom, $1,635.86/month. Both inclusive. Total utility costs for 2025: Hydro $2,941.27; Gas $860.90; Water/Sewer $1,403.44; Hot Water Heater $369.68. An excellent opportunity for investors seeking a stable, income-generating property in a sought-after location. No internal photos for tenant privacy.

579 Wayne Crescent, Midland

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