Headwaters Lodge, Caledon, ON, Canada

Headwaters Lodge - Nearby Homes for Sale

Name: Headwaters Lodge
Address: Caledon, Ontario, Canada
Telephone: +1-519-942-4440

Caledon, Ontario, Canada

Living Near Headwaters Lodge

Buyers searching for homes near Headwaters Lodge usually want two things: access and context. This page is built to make that comparison easier by combining available listings, street-level location details, and nearby amenities in one place. Instead of jumping between different tools, you can review homes and local points of interest side by side, then decide which streets or neighborhoods match your priorities. For Caledon, ON, that means you can quickly compare options around a known destination before spending time on private tours.

Right now, this page shows 57 nearby homes and 20 surrounding points of interest. You can use the listing table to compare address, bed and bath counts, and list price, then use the categories section to understand what types of amenities are clustered around the area. Top nearby category signals include Accommodation. This structure helps you compare convenience, neighborhood activity, and market options without leaving the page.

If you are relocating or narrowing your search, start with the homes shown here, then expand your review to nearby categories and additional location details. This workflow gives a more complete picture than price alone and helps avoid shortlisting homes that do not fit your day-to-day needs. Availability and pricing can change quickly, so checking this page regularly is useful when you are actively searching near Headwaters Lodge. Once a property looks promising, contact an agent to confirm the latest status and schedule a showing.

Frequently Asked Questions

How many homes are currently listed near Headwaters Lodge?

There are currently 57 active or coming-soon homes displayed near Headwaters Lodge on this page.

What information does this page include for homes near Headwaters Lodge?

This page includes nearby home listings, home prices, bedroom and bathroom counts, and nearby points of interest around Headwaters Lodge in Caledon.

How can I compare neighborhoods around Headwaters Lodge?

Use the nearby homes table and points-of-interest sections to compare listing prices, surrounding amenities, and local access points before scheduling a tour.

Homes for sale near Headwaters Lodge, Caledon, ON, Canada

Address	Bed / Bath	Listing Price
24 MURRAY COURT WOW! Welcome to this exceptional Sunvale-built detached home offering approx. 3, 191 sq. ft. of beautifully upgraded living space on a rare pie-shaped lot, tucked away in a quiet Orangeville cul-de-sac! Featuring a grand 17-ft foyer, this carpet-free gem showcases a bright open-concept layout, desig Orangeville, ON Living Area: Sqft.	5 Beds, 4 Baths	$979,000
61 MILL STREET If your dream life includes biking downtown for coffee, gardening in the backyard, and knowing everyone on the street by name... welcome to Mill Street. A beautifully restored 1890 century home tucked into one of the most beloved pockets of town where vibrant century homes are being thoughtfully bro Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$775,500
2 - 73 TOWN LINE An exciting new opportunity by Sheldon Creek Homes, a trusted local builder known throughout Dufferin County for quality craftsmanship and thoughtfully designed homes. This pre-construction semi-detached home is anticipated for occupancy in January 2027, and offers the rare chance to personalize you Orangeville, ON Living Area: Sqft.	3 Beds, 3 Baths	$819,000
73 DUFFERIN STREET Welcome to this charming, detached home nestled on a quiet street in desirable Orangeville, offering exceptional value and comfort for first-time buyers, downsizers, or anyone seeking a cozy, well-maintained space to call home. Situated on a private, fully fenced lot, this property features a spacio Orangeville, ON Living Area: Sqft.	2 Beds, 2 Baths	$649,900
72A TOWN LINE Welcome to 72A Townline, a raised bungalow located on the south side of Orangeville, offering a great opportunity for buyers looking to enter the market and add their own vision over time. The main level features an open concept living and dining area with a large picture window that brings in natur Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$535,000
22 EWING WAY Your eyes do not deceive you-luxury so grand at this price point presents exceptional value! Prepare to be captivated by this exquisitely designed home on an approx 1-acre premium estate lot! Nestled in a prestigious, ultra-private, quiet enclave just 10 mins to Orangeville w/ a seamless 35-min driv Amaranth, ON Living Area: Sqft.	5 Beds, 6 Baths	$2,189,000
340 PERRY ROAD Location Location and Location, Welcome to this beautifully updated family home, perfectly situated in one of Orangeville's most sought-after neighborhoods! Enjoy the convenience of being just minutes from top-rated schools, shopping, dining, the hospital, and multiple parks all while also benefitin Orangeville, ON Living Area: Sqft.	4 Beds, 3 Baths	$599,999
5 BEECHNUT STREET Welcome to 5 Beechnut St, lovingly named "The Maple", nestled on one of the most sought after streets in the area where homes rarely come available. Set on a breathtaking 0.65 acre lot, this thoughtfully designed 4 bedroom, 4 bathroom home with original owners has been planned from the ground up wit Mono, ON Living Area: Sqft.	4 Beds, 4 Baths	$1,329,900
75 JOHN STREET Must see charming bungalow with tons of character and curb appeal. Soaring 10 ft. ceilings with original baseboards throughout this amazing home. Cozy dining room & living room with hardwood floors & wood stove. Family addition offers plenty of space for gatherings with walk out to new large deck ar Orangeville, ON Living Area: Sqft.	3 Beds, 1 Bath	$699,000
91 FRENCH DRIVE In a neighbourhood filled with executive homes, this stately red brick Victorian stands entirely on its own. Full of character, individuality, and timeless craftsmanship, it offers something increasingly rare: the charm and soul of a true century home paired with the comfort and setting of one of Mo Mono, ON Living Area: Sqft.	4 Beds, 2 Baths	$999,999
112 JORDAN DRIVE Motivated Seller! This Four Bedroom Fully Detached All Brick Stoneybrook Model That Offers 1933 Square Feet Plus The Basement. Main Floor Features A Large Bright Eat-In Kitchen With Walk-Out To A Treed & Fully Fenced Backyard. Family Room Features A Large Window & a Gas Fireplace & Is Open To The Ki Orangeville, ON Living Area: Sqft.	4 Beds, 3 Baths	$769,900
45 CALEDONIA ROAD Welcome to 45 Caledonia Rd, a beautifully updated 3-level backsplit located on a quiet, family-friendly street in Orangeville. This bright and inviting home offers an open-concept kitchen with stainless steel appliances, large windows for plenty of natural light, 3 spacious bedrooms, an updated 4-pi Orangeville, ON Living Area: Sqft.	4 Beds, 2 Baths	$849,000
55 MCMASTER ROAD Gorgeous turn-key family home On the Hill in Orangeville. This well-maintained 3 bedroom, 3 bathroom home shows true pride of ownership throughout, featuring hardwood flooring on the main level, living room with soaring ceilings, a bright upgraded kitchen with stainless steel appliances, and a walko Orangeville, ON Living Area: Sqft.	3 Beds, 3 Baths	$799,900
1 STEVEN STREET Get into the market with this charming detached home tucked away on a quiet cul-de-sac. From the moment you arrive, the curb appeal stands out. A newer driveway and carport lead to a covered front porch-an ideal spot to unwind. Out back, you'll find a fully fenced yard with mature trees, offering pr Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$699,900
18A MARGARET STREET Sun-filled and full of charm, this beautifully maintained 1.5-storey detached home sits proudly on a bright corner lot in one of Orangeville's most established, tree-lined neighbourhoods. A fantastic opportunity to step into detached home ownership at an accessible price point, ideal for first-time Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$599,900
240 HOWARD CRESCENT Exceptional 4-bedroom, two-storey detached home, ideally situated in one of Orangeville's most desirable family-friendly neighbourhoods. Backing onto the Rebecca Hills Playground with Splashpad with no neighbours behind, this property offers the perfect combination of privacy, space, and scenic view Orangeville, ON Living Area: Sqft.	5 Beds, 4 Baths	$1,189,000
24 MURRAY COURT Welcome to this stunning Sunvale-built detached home offering approx. 3, 191 sq. ft. of total living space on a rare pie-shaped lot, nestled in a quiet, family-friendly cul-de-sac in Orangeville. Just a short walk to Headwaters Hospital and minutes from Island Lake Conservation Area, this beautifull Orangeville, ON Living Area: Sqft.	5 Beds, 4 Baths	$999,000
53 ANDERSON AVENUE Welcome to this exceptional residence offering over 5, 000 sq. ft. of beautifully finished living space, thoughtfully designed for both elegance and comfort. Perfectly situated just minutes from Highways 9 and 10 this home is conveniently located in a well established and sought after estate subdivi Mono, ON Living Area: Sqft.	5 Beds, 5 Baths	$1,579,900
91 FRENCH DRIVE Set within Mono's sought-after Fieldstone neighbourhood, this stately 2.5-storey red brick Victorian offers a rare blend of character, space, and everyday livability on a beautifully treed, just-under-half-acre lot. Surrounded by executive homes yet only minutes from town, the setting feels both est Mono, ON Living Area: Sqft.	4 Beds, 2 Baths	$1,044,900
234 HOWARD CRESCENT Welcome to this spacious all-brick family home offering incredible versatility for today's lifestyle-whether you're looking to move right in or take advantage of its excellent income potential. Ideally situated in a sought-after, family-friendly neighbourhood in Orangeville, this property features 4 Orangeville, ON Living Area: Sqft.	5 Beds, 4 Baths	$929,900
9 WELLINGTON STREET Historic Elegance Meets Modern Luxury at 9 Wellington St. Experience the perfect blend of century-old charm and high-end functionality in this grand 1926 home located on one of Orangeville's most prestigious streets. Spanning an impressive 4201 sq ft, this residence features 2 kitchens with a self-c Orangeville, ON Living Area: Sqft.	6 Beds, 5 Baths	$1,499,900
334 PERRY ROAD Stunning & Immaculately Maintained 4 Bedroom & 2.5 Bath Brick Detached Home With Many Updates! Beautiful Kitchen With Quarts Counters, Backsplash, SS Appliances, Soft Close Cabinets & Pot Lights, Opens Up To Large Breakfasts Area & Family Room. Family Room Features Updated Gas Fireplace With Stunnin Orangeville, ON Living Area: Sqft.	4 Beds, 3 Baths	$849,900
125 DUFFERIN STREET !!Like Brand New !! FULLY RENOVATED!!LEGAL BASEMENT APARTMENT with SEPRATE ENTRANCE!! Semi Detached Bungalow on the Corner. All the Comforts of A New Home w/ New Windows, Doors, Lighting, Plumbing, Electrical, Appliances, Flooring & Paint. New Soffits, Facia, Concrete Pad & Side Fence. Tiled Entry w Orangeville, ON Living Area: Sqft.	6 Beds, 3 Baths	$778,000
48 TOWNLINE Welcome to 48 Townline, a truly charming Century Home built in 1890, where timeless character meets everyday comfort. From the moment you step inside, you'll appreciate the warmth and craftsmanship of a bygone era, showcased through soaring 9-foot ceilings, original pine plank floors, oversized base Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$624,900
47 BUENA VISTA DRIVE OPEN HOUSE SUNDAY APRIL 12, 12-2PM ******Experience the perfect blend of modern living and timeless comfort in this beautifully updated 5-bedroom (4+1), 4-bathroom home, ideally located in a highly sought-after neighbourhood close to top-rated schools and hospitals.From the moment you step insid Orangeville, ON Living Area: Sqft.	5 Beds, 4 Baths	$1,240,000
24 MURRAY COURT Welcome to this stunning Sunvale-built detached home offering approx. 3, 191 sq. ft. of total living space on a rare pie-shaped lot, nestled in a quiet, family-friendly cul-de-sac in Orangeville. Just a short walk to Headwaters Hospital and minutes from Island Lake Conservation Area, this beautifull Orangeville, ON Living Area: Sqft.	5 Beds, 4 Baths	$899,000
327 PERRY ROAD Welcome to this beautifully updated family home, perfectly situated in one of Orangeville's most sought-after neighborhoods! Enjoy the convenience of being just minutes from top-rated schools, shopping, dining, the hospital and multiple parks - all while having effortless access to Highway 10 and Hi Orangeville, ON Living Area: Sqft.	3 Beds, 3 Baths	$799,900
118 OAK RIDGE DRIVE Some homes are built for everyday living. Others are built for when people come over. This one does both. Inside, the home reveals itself through thoughtful updates and a layout that balances everyday living with entertaining. The kitchen anchors the main floor with a massive island, tasteful finish Orangeville, ON Living Area: Sqft.	4 Beds, 4 Baths	$1,240,000
35 KETCHUM STREET There's a certain ease to life in Fieldstone where mornings begin with sunlight pouring through, coffee shared around the oversized kitchen island and moments tucked into spaces designed for both connection and calm. From the moment you step into the grand foyer, this home feels elevated yet effortl Mono, ON Living Area: Sqft.	4 Beds, 4 Baths	$1,599,900
38 WELLINGTON STREET Don't miss this incredible opportunity to own a fully detached home in charming Orangeville, Ontario, featuring a fully self-contained secondary dwelling - a rare two-for-one property offering exceptional flexibility for investors, multi-generational families, or buyers looking to offset their mortg Orangeville, ON Living Area: Sqft.	4 Beds, 2 Baths	$699,000
20 ANDERSON AVENUE Refined Living Meets Everyday Comfort at 20 Anderson Avenue. Set on a quiet street in Mono, this beautifully appointed residence offers over-the-top space, thoughtful layout, and exceptional entertaining potential. With a total of six bedrooms and five bathrooms, every detail has been designed to ac Mono, ON Living Area: Sqft.	6 Beds, 5 Baths	$1,649,900
11 LYNDA AVENUE Welcome to this exceptional two-storey brick home in the sought-after Purple Hill community, perfectly positioned just minutes from Island Lake Conservation Area, Purple Hill park and Island lake public school, an ideal setting for families. Set on a beautifully landscaped and private 0.57-acre lot Mono, ON Living Area: Sqft.	5 Beds, 4 Baths	$1,298,900
184 HOWARD CRESCENT Watch Virtual Tour Nestled in one of Orangeville's most desirable family neighbourhoods, this beautifully upgraded 4-bedroom, 4-bath detached home backs onto a serene park - offering privacy and tranquility with no rear neighbours. Just steps to Island Lake School and the hospital, and moments f Orangeville, ON Living Area: Sqft.	4 Beds, 4 Baths	$899,888
43 PRINCESS STREET 43 Princess Street, Orangeville presents a solid opportunity to enter an established neighbourhood on the south end of town. Known for its mature setting and convenient access to everyday amenities, this location supports practical day to day living with proximity to schools, parks, and main routes Orangeville, ON Living Area: Sqft.	4 Beds, 2 Baths	$610,000
110 JORDAN DRIVE Rare 5+2 bed, 5 bath home in Orangeville with legal 2-bed apartment. Features chef's kitchen, hardwood throughout, skylights, 2 primary suites w/ heated floors & rain shower, plus walkout patio (id:58753) Orangeville, ON Living Area: Sqft.	7 Beds, 5 Baths	$1,249,999
325 MARSHALL CRESCENT Rare 4 plus 3 bedroom home offering 7 rooms total with separate entrance, income potential, and like-new roof, perfect for multi-generational living or Airbnb and long-term rentals. With approximately 3, 000 square feet of finished living space, the main floor features a living room and a cozy famil Orangeville, ON Living Area: Sqft.	7 Beds, 4 Baths	$879,000
65 BUENA VISTA DRIVE Wake up slowly as the morning light filters through the windows of your private primary retreat, tucked quietly on its own side of the home. It's peaceful here. No footsteps overhead, no hallway traffic and just your own space to start the day, w/views stretching out over your backyard oasis. Ready Orangeville, ON Living Area: Sqft.	4 Beds, 3 Baths	$1,199,900
18 AMANDA STREET Welcome to 18 Amanda Street, where opportunity awaits! Nestled on a mature, tree-lined street, this property boasts a generous corner lot with the kind of space and privacy that's becoming increasingly rare. The large yard provides ample room for gardening, pets, and outdoor entertainment. It's loca Orangeville, ON Living Area: Sqft.	3 Beds, 1 Bath	$599,000
2 PRINCESS STREET Rare find! This beautifully designed linked raised bungalow is attached only at the garage, offering the privacy of a detached home. The perfectly situated on an end lot, it's just a short walk to schools, shopping, and restaurants. Step inside to discover a bright, open living and dining area with Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$672,000
25A MARGARET STREET A Double Garden Door Walk Out Basement PLUS A Side Entrance Offers In-Law Capability! This Brick Raised Bungalow Has Garage, 3+1 Bedrooms, 2 Updated Baths, L-Shaped Living/Dining & Sky Light In Kitchen. A Partially Finished Basement w Large Rec Room Gives Opportunity For Multi Functional Areas Of Yo Orangeville, ON Living Area: Sqft.	4 Beds, 2 Baths	$674,900
75 JOHN STREET Must see charming bungalow with tons of character and curb appeal. Soaring 10 ft. ceilings with original baseboards throughout this amazing home. Cozy dining room & living room with hardwood floors & wood stove. Family addition offers plenty of space for gatherings with walk out to new large deck ar Orangeville, ON Living Area: Sqft.	3 Beds, 1 Bath	$715,000
7 IRONWOOD COURT The neighbourhood of your dreams & the home you'll never want to leave. If you ask anyone in the Orangeville area what their dream street is, chances are they'll say Ironwood Court - and homes here rarely come up for sale. Tucked away on an exclusive cul-de-sac and backing onto protected Mono/Island Mono, ON Living Area: Sqft.	3 Beds, 4 Baths	$1,899,000
18 QUARRY DRIVE Move-in ready semi-detached home with a practical layout and plenty of space. The main floor features a bright living and dining area with updated laminate flooring, a large primary bedroom, and an eat-in kitchen with a walkout to the deck. The lower level adds two additional bedrooms, a generous fa Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$499,900
327 PERRY ROAD Welcome to this beautifully updated family home, perfectly situated in one of Orangeville's most sought-after neighborhoods! Enjoy the convenience of being just minutes from top-rated schools, shopping, dining, the hospital and multiple parks - all while having effortless access to Highway 10 and Hi Orangeville, ON Living Area: Sqft.	3 Beds, 3 Baths	$819,900
53 ANDERSON AVENUE Welcome to this exceptional residence offering over 5, 000 sq. ft. of beautifully finished living space, thoughtfully designed for both elegance and comfort. Perfectly situated just minutes from Highways 9 and 10 this home is conveniently located in a well-established and sought-after estate subdivi Mono, ON Living Area: Sqft.	5 Beds, 5 Baths	$1,599,900
184 HOWARD CRESCENT Watch Virtual Tour Nestled in one of Orangeville's most desirable family neighbourhoods, this beautifully upgraded 4-bedroom, 4-bath detached home backs onto a serene park - offering privacy and tranquility with no rear neighbours. Just steps to Island Lake School and the hospital, and moments f Orangeville, ON Living Area: Sqft.	4 Beds, 4 Baths	$939,900
33 QUARRY DRIVE Welcome to 33 Quarry Drive-a versatile raised bungalow ideal for families, extended family, or investors. Bright upper level with open-concept living and dining, hardwood flooring, large picture window, and a primary bedroom with renovated 4-pc ensuite. Finished lower level offers two bedrooms, a fu Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$639,000
325 MARSHALL CRESCENT This is your chance to own one of the most valuable and rare layouts currently available in Orangeville, offering approximately 3, 000 sqft of finished living space, including four full bedrooms above grade plus a fully finished three-bedroom lower level for exceptional space, flexibility, and incom Orangeville, ON Living Area: Sqft.	7 Beds, 4 Baths	$899,999
48 TOWNLINE Welcome to 48 Townline, a truly charming Century Home built in 1890, where timeless character meets everyday comfort. From the moment you step inside, you'll appreciate the warmth and craftsmanship of a bygone era, showcased through soaring 9-foot ceilings, original pine plank floors, oversized base Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$649,000
91 FRENCH DRIVE This 2.5-storey red brick Victorian is a true standout in Mono's Fieldstone neighbourhood. Set on a sprawling, just-under-half-acre lot among other executive homes, it beautifully combines historic charm with fresh updates. You get the perfect mix of character and modern comfort, all while staying o Mono, ON Living Area: Sqft.	4 Beds, 2 Baths	$1,050,000
20 ANDERSON AVENUE Refined Living Meets Everyday Comfort at 20 Anderson Avenue. Set on a quiet street in Mono, this beautifully appointed residence offers over-the-top space, thoughtful layout, and exceptional entertaining potential. With a total of six bedrooms and five bathrooms, every detail has been designed to ac Mono, ON Living Area: Sqft.	6 Beds, 5 Baths	$1,699,900
366 MARSHALL CRESCENT Upgraded 4 + 2 bedrooms, 4 bathrooms house located in a highly sought-after location in Orangeville. Stone walkway leading to the covered porch. Main floor features formal Living, Dining and Family rooms and a renovated eat-in kitchen with granite counter-top, stainless steel appliances, backsplash Orangeville, ON Living Area: Sqft.	6 Beds, 4 Baths	$999,000
35 KETCHUM STREET This stunning home, located in the sought-after Fieldstone neighbourhood, feels like its been lifted from the pages of a magazine! As you step into the grand foyer with soaring ceilings, you're welcomed by a striking staircase, an elegant dining room, and a versatile den/office/study perfect for wor Mono, ON Living Area: Sqft.	4 Beds, 4 Baths	$1,699,800
322 PERRY ROAD Stunning Upgraded 3+1 Bedroom 3.5 Bath Detached Home Is Located In Most Desirable Area Of Orangeville, Conveniently Located Near Hwy 10 & Hwy9. The Upper Level contains 3 Generous size Bedrooms with Custom Closets. Brand New Vinyl Flooring All Over(2025) and ceramic tiles in Washroom, Freshly Painte Orangeville, ON Living Area: Sqft.	4 Beds, 4 Baths	$875,000
33 QUARRY DRIVE Welcome to 33 Quarry Drive, This beautiful semi-detached home is uniquely designed to offer great options for home ownership or an investment property. The layout works for several options: single family with adult children or extended family, live upstairs and rent the lower level for additional in Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$669,000
58 MCMASTER ROAD Welcome to this delightful family home! This charming 3-bedroom, 3-bathroom residence is nestled in a family-friendly neighborhood, just steps away from schools, conservation areas, trails, and a hospital. With approximately 1, 616 square feet of living space plus an additional 800 square feet in th Orangeville, ON Living Area: Sqft.	4 Beds, 3 Baths	$959,000
18 TOWNLINE Welcome to 18 Townline - located in beautiful Orangeville! This stunning 4 level sidesplit boasts tasteful finishes throughout and has space for the entire family. The main floor features a bright open concept family room, eat in kitchen with a walkout to the backyard deck as well as a cozy dining r Orangeville, ON Living Area: Sqft.	3 Beds, 2 Baths	$769,900