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17 Sleepy Hollow Lane
Rural Whitchurch-Stouffville Whitchurch-Stouffville L4A 3G7

$2,395,000
Residential Freehold beds: 4+2 baths: 4.0

Main Photo: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 1: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 2: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 3: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 4: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 5: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 6: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 7: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 8: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 9: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 10: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 11: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 12: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 13: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 14: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 15: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 16: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 17: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 18: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 19: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 20: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 21: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 22: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 23: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 24: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 25: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 26: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 27: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 28: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 29: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 30: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 31: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 32: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 33: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 34: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 35: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 36: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 37: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 38: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 39: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 40: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 41: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 42: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 43: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 44: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 45: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 46: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 47: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 48: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 49: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Photo 50: 17 Sleepy Hollow Lane in Whitchurch-Stouffville: Rural Whitchurch-Stouffville House for sale : MLS®# N14034368
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
N14034368
Bedrooms:
4+2
Bathrooms:
4
Welcome to this exceptional, newly renovated executive residence in the prestigious community of Sleepy Hollow Estates.Perfectly situated on one of the most desirable cul-de-sac lots, this remarkable home backs onto protected conservation land anda scenic golf course, offering breathtaking western exposure and unforgettable sunset views. Designed with both elegance andfunctionality in mind, this expansive home is ideal for a large or multi-generational family. The beautifully appointed kitchen features a centre island, exquisite granite countertops, and a spacious breakfast area with a walk-out to the deck-perfect formorning co?ee or entertaining guests. The oversized family room is warm and inviting, highlighted by a cozy gas fireplace andwalk-out access to a large deck overlooking the stunning, fully rebuilt Betz swimming pool-creating the ultimate privatebackyard retreat. A grand central staircase adds timeless elegance and leads to four generously sized bedrooms. The luxuriousprimary suite serves as a private retreat, complete with a sitting area, walk-in closet, and a modern five-piece spa-inspiredensuite. The fully finished walk-out basement with a separate side entrance o?ers incredible versatility. Featuring a spaciousrecreation room, bar or secondary kitchen, games area, fireplace, two additional bedrooms, and a four-piece bath, this levelpresents the perfect opportunity for an in-law suite or extended family living. Complete with a three-car driveway andbeautifully updated throughout, this stunning property offers the perfect blend of luxury, comfort, and lifestyle. A rareopportunity to own a truly special home in one of the area's most sought-after communities. **New Furnace 2026 **Recentlyrenovated throughout with quality finishes and thoughtful upgrades**
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Approx. Age:
31-50
Total Approx Floor Area:
3500-5000
Lot Depth:
268'1"
Lot Frontage:
84'10½"
Topography:
Wooded/Treed
Direction Faces:
East
Bedrooms:
4+2
Bathrooms:
4.0
Water supply:
Well
Kitchens:
2
Kitchens in Basement:
1
Bedrooms Above Grade:
4
Bedrooms Below Grade:
2
Kitchens Above Grade:
1
Rooms Above Grade:
10
Heating type:
Forced Air
Heating Fuel:
Gas
Foundation:
Concrete
Roof:
Shingles
Basement:
Finished with Walk-Out, Separate Entrance
Fireplace Features:
Family Room, Other, Rec Room
Fireplace/Stove:
Yes
Garage:
Built-In
Garage Spaces:
3.0
Parking Features:
Available, Front Yard Parking, Private Triple
Parking Spaces:
6
Total Parking Spaces:
9.0
Family Room:
Yes
Possession Details:
TBD
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$9,880.88 / 2026
Assessment:
$- / -
York
Whitchurch-Stouffville
Rural Whitchurch-Stouffville
Cul de Sac/Dead End, Fenced Yard, Golf, Greenbelt/Conservation, Public Transit, Wooded/Treed
Auto Garage Door Remote, Carpet Free, In-Law Capability, Sump Pump, Water Heater, Water Softener
Deck, Privacy, Seasonal Living
Alarm System, Smoke Detector
HWT
SubZero fridge, KitchenAid gas stove, dishwasher, stove hood, Miele side-by-side washer and dryer, all electric light fixtures, central air conditioner (not working), gas furnace, water softener, California shutters, 3 new electric garage doors, winter poolcover, pool heater and filter. All in "as is" condition.
N/A
Brick
Golf Course, Pond, Trees/Woods
Floor
Type
Size
Other
Ground
Foyer
13'1" × 11'2¼"
Hardwood Floor, Closet, Closet
Ground
Living Room
18'10" × 13'
Hardwood Floor, Pot Lights, Bay Window
Ground
Dining Room
15'1" × 12'9"
Hardwood Floor, Pot Lights, Fireplace
Ground
Kitchen
13' × 12'11⅛"
Granite Counters, Centre Island, Overlooks Backyard
Ground
Breakfast
14'11" × 12'10"
Tile Floor, W/O To Deck, French Doors
Ground
Family Room
19'11¾" × 19'11¾"
Fireplace, Hardwood Floor, W/O To Deck
Ground
Office
12'9" × 12'
Hardwood Floor, Overlooks Frontyard
Second
Primary Bedroom
30'1" × 18'3"
Walk-In Closet(s), 5 Pc Bath, Combined w/Sitting
Second
Bedroom 2
15'7" × 13'
Hardwood Floor, Walk-In Closet(s), Pot Lights
Second
Bedroom 3
14'6" × 13'1"
Hardwood Floor, Closet, Pot Lights
Second
Bedroom 4
13'1" × 12'
Hardwood Floor, Double Closet, Pot Lights
Lower
Recreation
19'1" × 18'10¾"
Fireplace, W/O To Yard, B/I Bar
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Laundry Level:
Lower Level
Date Listed:
Oct 14, 2026
Original Price:
$2,395,000
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Listed by RE/MAX REALTRON REALTY INC.
Data was last updated October 20, 2026 at 04:15 AM (UTC)
Area Statistics
Listings on market:
94
Avg list price:
$2,288,500
Min list price:
$585,000
Max list price:
$38,000,000
Avg days on market:
63
Min days on market:
1
Max days on market:
714
These statistics are generated based on the current listing's property type and located in Rural Whitchurch-Stouffville. Average values are derived using median calculations. This data is not produced by the MLS® system.
SAM  CHAIM


Why Clients Choose Sam

 

Experience You Can Trust

Decades of Toronto real estate expertise.

 

Skilled Negotiation

Helping clients protect their investment.

 

Local Market Knowledge

Neighbourhood insights beyond listing data.

 

Personalized Service

Every client receives tailored advice.
 


Frequently Asked Questions

 

What areas does Sam Chaim serve?

Sam helps buyers and sellers throughout Toronto, North York and the Greater Toronto Area.

 

How much is my Toronto home worth?

Home values depend on neighbourhood, property condition, comparable sales and current market conditions. Sam offers complimentary home evaluations.

 

Is now a good time to buy Toronto real estate?

Market conditions change throughout the year. Sam provides personalized advice based on your goals, budget and the latest Toronto market trends.

 

What makes Sam Chaim different?

Sam combines decades of experience with a relationship-first approach, providing honest guidance and strategic advice tailored to each client's needs.

 

How do I get started?

Schedule a consultation, request a home evaluation or browse current listings to begin your real estate journey.

 


RSS

The Competition is Fierce

The Canadian housing market has seen record prices over the last two years. With record-low inventories and increasing demand, prices soared from coast-to-coast. It is the perfect recipe to create a seller’s market, meaning that competition for homes is fierce. RE/MAX brokers reported multiple-offer scenarios in key Canadian housing markets such as Toronto, Ottawa, and Vancouver. This leads many to question what prompts multiple offers and how to win a bidding war.

How a Bidding War Works

In a seller’s market, there are more buyers than homes available for sale. The combination of limited inventory and high demand often puts upward pressure on prices, creating the ideal conditions for a bidding war. Homes typically sell quickly in a seller’s market, and multiple offers on a listing are more likely, giving the seller the upper hand.

When market conditions favour sellers, demand is usually up, and inventory is down, which has been the case throughout the pandemic. With few listings on the market, the seller and listing agent may choose to set an offer deadline by which interested buyers must submit their offers. In a bidding war, there are multiple offers and pressure for potential buyers to compete to raise their bids, pushing the sale price well above asking.

A bidding war typically follows these steps:

  • Buyers interested in the property submit their offers to the seller or real estate agent. The offer typically includes the proposed purchase price, conditions or contingencies, and the desired closing timeline.

  • The seller reviews all received offers and assesses their attractiveness based on the purchase price, closing timeline, contingencies, financing details, and buyer qualifications.

  • The seller may negotiate and respond to one or more buyers by issuing counteroffers. Counteroffers typically involve adjustments to the original offer’s purchase price, terms, or conditions.

  • A bidding war can emerge if multiple buyers are still interested and engaged. Buyers may be notified that they are in a competitive situation and can revise and improve their offers.

  • Buyers raise their initial offers, often exceeding the original asking price, to outbid other potential buyers and demonstrate their commitment to securing the property.

  • The seller evaluates the revised offers and determines which is most favourable based on the purchase price, conditions, financing, and the buyer’s ability to close the deal.

  • The seller accepts the winning offer, and the buyer proceeds to fulfill any remaining conditions or contingencies specified in the offer. Once all requirements are met, the sale is finalized, and the closing process begins.

In Canada, policymakers have introduced various measures to address these issues. For instance, cooling measures have been implemented to curb excessive speculation and prevent housing bubbles. These measures include foreign buyer taxes, restrictions on foreign investments, and stricter mortgage qualification rules. The objective is to ensure that the housing market remains accessible to Canadian residents and that affordability is not compromised.

The Importance of a Real Estate Agent in a Seller’s Market

Sellers can only hope to receive multiple offers on their listings. However, from the buyer’s perspective, it can be a frustrating and emotional experience. When you look at the bigger picture of a home purchase, “winning” is relative to the buyer’s goals. If the only objective is to buy a specific home, then offering the highest possible purchase price with no offer conditions is the way to go. It is the way to get the house you want.

However, most homebuyers have other goals, such as buying within a specific price point and a defined timeline for closing the deal and moving in. Then there’s the home itself. Does the buyer intend to fix and flip it? Demolish and build? Or are they seeking a move-in-ready home? Whatever that goal is, buyers should communicate it to their realtor, who can help strategize how to reach it. While you might need to make some concessions, your realtor will do what is necessary to realize as many of your goals as possible.

The real estate agent’s job is to approach the transaction objectively. This includes the process of real estate bidding and negotiating. They can bring logic to this emotional process and potentially help you avoid a massive financial risk. A professional, experienced real estate agent who knows the local market can help you keep your eyes on the prize – a home that suits you, your budget, and your long-term goals.

How to Win a Bidding War

Here are some strategies to help you make an intelligent bid and a wise purchase if all goes in your favour:

Know Your Budget – Knowing how much you can spend on a home is critical for a homebuyer. Getting a mortgage pre-approval can provide valuable insight and guarantees your mortgage interest rate for up to 120 days, which is essential as rates climb upward. When you’re ready to make an offer, despite your eagerness to win the war, so to speak, do your due diligence and consult with your lender before making a firm offer.

Consider the Worth of the House – This is especially important as housing prices soar, even in smaller communities. Your real estate agent will pull recent sales stats, giving you valuable insight into the selling price of comparable homes in the same neighbourhood and under the same market conditions. This can help you determine an offer you’re comfortable with and whether competing against other bids makes sense.

Reduce Your Offer Conditions – In a seller’s market, having fewer conditions on your offer can work in your favour. Flexibility on your desired closing date or inclusions could tip the scales in your favour. A clean offer is more likely to win in a seller’s market, especially in a bidding war. With that said, we highly recommend making the offer conditional on a satisfactory home inspection. Remember that even if you discover issues with the home in a seller’s market, you may still not have much negotiating power. However, having this information will help you decide if the house is worth what you’re expected to pay.

Consider the Location – Beyond the home itself, remember that location is a huge factor in determining a home’s value. Premium neighbourhoods come at higher prices, thanks to proximity to amenities, green space, transit routes, shopping, services, and other factors. Whatever draws people into the area is likely a factor driving up the selling price.

How to Avoid a Bidding War

Short-Term Strategy – One trick to winning a bidding war is to avoid it altogether. Make an offer before the home hits the MLS system or gains buyer attention through an open house. Your agent will best advise you on how to proceed, so prepare to drop everything to tour a new listing and make your offer before someone else does! (Note: Mortgage pre-approval in this scenario is critical.)

Long-Term Planning – The spring and summer real estate markets see the most activity under normal conditions, with buyers out in droves and bidding wars bubbling at the surface. If you’re not in a hurry to buy, minimize your competition and possibly even price by shopping in the “off” season. Winter sees a drop in inventory and demand, reducing your chance of being outbid.

Do Your Homework – You’ve determined how much you can afford, right? And you know what the home is worth based on the comparables your real estate agent pulled for you. You also know what the home is worth based on your lifestyle, budget, and future employment prospects. Make a bid that’s reflective of all these considerations. Before jumping on the bidding bandwagon, be confident you’re getting a good deal.

When asking how you win a bidding war, remember that the spoils don’t always go to the highest bidder. Know when to walk away. Even in a seller’s market, the perfect home is out there, waiting for you to find it.

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This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.