Recently Listed Open House 8/29 12pm - 2pm
3505 Middle Cheshire Road
Canandaigua, NY, 14424 $ 499,900
Bedrooms5 Baths3.0 Sq 2,781 Monthly Estimate*
$ 3,156
for $499,900 with 5 bedrooms and 3 full baths. This 2,781 square foot home was built in 1962 on a lot size of 1.
SPECTACULAR SPRAWLING COLONIAL offering exceptional size, space and versatility with over 2,700 sq. ft., five bedrooms and three full bathrooms—all situated on a beautiful one-acre lot with mature trees, scenic country views and incredible privacy! This timeless home offers room to spread out inside and out, beginning with an estate-like setting, expansive curved driveway and additional parking area leading to a charming foyer with a sidelight. The spacious interior features a stunning White & Bright eat-in kitchen with gorgeous cabinetry, breakfast bar and hardwood floors. An entertainment-sized living room is filled with natural light and highlighted by a beautiful fireplace with a custom mantel and dentil molding. The charming formal dining room features custom built-ins, chair rail and hardwood floors, while the expansive family room showcases rich wood-paneled walls and additional built-ins. An extremely rare first-floor bedroom wing offers incredible flexibility with a separate foyer, spacious bedroom with hardwood floors, huge walk-in closet and an updated full bathroom featuring a walk-in shower, heated floors and double vanity—an exceptional opportunity for an in-law suite, guest quarters or private first-floor retreat! A must-have enclosed porch with tongue-and-groove wood walls and ceilings overlooks the peaceful country setting. Upstairs, the exceptional space continues with four spacious bedrooms, all with hardwood floors, plus another full bathroom. An expansive walk-out basement provides even more space and possibilities! Outside, the oversized one-acre lot is truly special, with mature trees, a charming split-rail fence, storage shed, sweeping lawn and plenty of room for outdoor living, entertaining, recreation and privacy. All of this just minutes from Canandaigua Lake and the City of Canandaigua, with fantastic restaurants, shopping and recreation nearby. Additional highlights include low-maintenance vinyl siding and windows plus a permanent whole-house generator! Over 2,700 sq. ft. + 5 bedrooms + 3 full baths + flexible first-floor living + an incredible one-acre setting—a rare combination of space, versatility and location!
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Open House
8/29/2026 12:00 PM - 2:00 PM
3505 Middle Cheshire Road Canandaigua, NY
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesInteriorInterior Amenities EntranceFoyer EatInKitchen SeparateFormalLivingRoom Pantry PullDownAtticStairs SeeRemarks WindowTreatments ConvertibleBedroom InLawFloorplan BathInPrimaryBedroom MainLevelPrimary PrimarySuite
Basement Full WalkOutAccess SumpPump
Flooring Carpet Hardwood Tile Varies
Total Fireplaces 1
Total Stories 2
Basement (Y/N) Yes
Air Conditioning Y/N Yes
Heating Y/N Yes
Window Features Drapes ThermalWindows
Fireplace Y/N Yes
Half Baths 0
Laundry Features InBasement
Total Bedrooms 5
Main Level Bedrooms 1
Main Level Bathrooms 2
Total Baths 3
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GeneralSewer SepticTank
Heating Gas Zoned HotWater
Cooling Zoned CentralAir
Utilities CableAvailable HighSpeedInternetAvailable WaterConnected
Possession CloseOfEscrow
Roof Asphalt
Appliances Dishwasher ElectricOven ElectricRange Disposal GasWaterHeater Refrigerator TanklessWaterHeater
Garage Spaces 2.0
Patio/Porch Features Patio
Architectural Style Colonial
Construction Materials VinylSiding CopperPlumbing
School District Canandaigua
Year Built 1962
Electric CircuitBreakers
Stories Count 2
Township Not Applicable
Levels Two
Property Subtype SingleFamilyResidence
County Ontario
Property Type Residential
Attached Garage Yes
Garage Y/N Yes
Other Structures Sheds Storage
Total Rooms 9
Full Baths 3
Status Active
City Canandaigua Town
Senior Community Y/N No
High School District Canandaigua
Number Of Units Total 0
MLS Area Canandaigua Town-322400
Lot Size Units Acres
Lot Size Square Feet 43560.0
Year Built Details Existing
Tax Annual Amount 6074.0
Property Condition Resale
Standard Status Active
Middle/Junior School District Canandaigua
Elementary School District Canandaigua
Tax Assessed Value 265400
TaxOtherAnnualAssessmentAmount 0.0
Tax Lot 17
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ExteriorExterior Amenities BlacktopDriveway EnclosedPorch Porch Patio PrivateYard SeeRemarks
Parking Features Attached Underground Garage CircularDriveway Driveway
Lot Features Rectangular RectangularLot Wooded
Water Source Connected Public
Lot Size Area 1.0
Foundation Details Block
Building Area Total 2781.0
Lot Dimensions 184X238
Lot Size Acres 1.0
Waterfront Y/N No
Other Equipment Generator
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* Excluded FeaturesAffordability Calculator
- Monthly Principal & Interest
- $3,156
- Monthly Property Taxes
- $506
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Canandaigua, NY
Average List Price $595,479
Percent of Sale Price 19%
About Canandaigua, NY 27,659 Population
10% Since 2002
$ 56,048 Median Income
45.63 Median Age
25% Households with Children
Trends Information provided by ATTOM Data Solutions.
3037994 Elementary School
3038002 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 8/28/2026 | $499,900 | | Listed Price |