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Good evening. Welcome to 269 Academy Road, Cheshire, CT

$789,900
4
Beds
3.00
Baths
3,020
SqFt
0.96
Acres

Pricing Insight: Originally listed for $789,900, the price has remained unchanged for approximately 10 days. This property has been on the market for approximately 10 days.

269 Academy Road, Cheshire, CT is a 4-bed, 3-bath, 3,020 square foot home built in 1968 , featuring cape cod architecture.

This home is within the Cheshire school district. Local, with nearby schools including Highland.

MLS #: 24164730

Offered Price: $789,900

Residence Type: Single Family

Architectural Style: Cape Cod

Living Area: 3,020 Sq. Ft.

Lot Size: 0.96 Acres

Neighborhood: N/A

County: New Haven

Year Built: 1968

Design & Construction: Frame

Heating: Hot Water

Cooling: Central Air

Garage Spaces: 2

Price per Sq Ft as listed: $262

Estimated Tax: $10,576

Days on Market: 6

$1,299,000
4 Beds · 4 Baths · 4,016 Sq Ft
3 Melrose Drive, Cheshire
$1,120,000
4 Beds · 3 Baths · 2,731 Sq Ft
6 Melrose Drive, Cheshire
$1,455,100
5 Beds · 4 Baths · 4,785 Sq Ft
8 Melrose Drive, Cheshire
$1,299,000
4 Beds · 5 Baths · 4,011 Sq Ft
17 Melrose Drive, Cheshire
$1,600,000
4 Beds · 4 Baths · 5,159 Sq Ft
9 Melrose Drive, Cheshire

Home Automation: Not specified

Energy Features: Generator Ready, Programmable Thermostat

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Hot Water

Fuel Tank Location: In Basement

Cooling System: Central Air

Hot Water System: Other

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $262 / Sq. Ft.

Tax assessed value: $355,600

Estimated Tax: $10,576

Architectural Style: Cape Cod

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1968

Living Area: 3,020 Sq. Ft.

Lot Size: 0.96 Acres

Fuel: Oil

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AUTOMATED VALUATION ESTIMATE

Powered by Realtors Property Resource® (RPR)

Note: Computer-generated estimate, not an appraisal.

Understanding This Valuation

The RPR AVM considers:

  • Recent sales of comparable properties
  • Property characteristics and location
  • Market trends in Cheshire
  • Statistical modeling algorithms
Local Market Context
Active Listings: 42
Average Price: $362,050
Average DOM: 6 days

Complimentary CMAs, no obligation

Welcome to this exquisite expanded 4-bedroom, 3-bath Cape nestled on almost an acre and a short drive from the heart of Cheshire. Inside, you'll find 2,755 sq ft of open living space with hardwood floors throughout. The light-filled living room offers a wood-burning fireplace and flows into a stylish gourmet kitchen featuring stainless steel appliances, granite countertops and a center island. Flowing from the kitchen, the dining area leads to a stunning family room with a vaulted ceiling and wood beams, creating a warm, inviting space for hosting and everyday living. The main level also offers a library/home office, a convenient laundry/mudroom, two bedrooms and a full bathroom. A gorgeous sliding door opens to the lower level featuring an additional 265 sq ft of living space, a second wood-burning fireplace, and plenty of space to relax and entertain. The upper level offers two oversized bedrooms, each with en-suite baths and walk-in closets creating calming retreats. The tranquil backyard features a two-level deck ideal for dining & unwinding, a fire pit, and a fully fenced yard for added privacy & safety. Abundant storage throughout including a 2-car attached garage, 1,317 sq ft of basement space, and generous closets. Among the many noteworthy upgrades are a new driveway (2023), a 30-year architectural roof (2021), paver front walkway (2022), a five-zone boiler and dual central air systems (2018) and generator-ready since 2024. Schedule your private tour today!

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Flood Risk Assessment

Location Analysis:
Inland Cheshire location
Water Proximity:
No direct water access
Topography:
Standard terrain • 1.0 acres
Recommendations:
  • Consult FEMA Flood Maps for accurate zone info
  • Consider flood insurance based on professional assessment
  • Evaluate property drainage during inspection
  • Review local flood history with town officials
Risk Level: Low

Minimal flood risk indicators. Verify with FEMA flood maps.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

  • Dining & Café Access: Low to Moderate
  • Daily Services: Limited
  • Recreational Space: Limited Nearby
How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

  • Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
  • Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

42

Homes For Sale

$362,050

Average List Price

Mechanicals & Utilities: Hot Water • Oil • Central Air • Private Well water • 2 fireplaces

Exterior Features

Exterior Construction: Vinyl Siding

Roof Type: Asphalt Shingle

Foundation: Concrete

Garage: Attached Garage (2 car)

Patio/Deck: Deck

Utilities: Water: Private Well

Only motif connects you to a certified
"Local Market Expert"

Agent Photo
George Antonopoulos
Real Estate Advisor
Cheshire • Connecticut Shoreline
Licensed Real Estate Agent – Connecticut
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 Verified Motif Advisor
Good evening George, I'm interested in
269 Academy Road, Cheshire, Connecticut
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Agent Photo
George Antonopoulos
george@appzentric.com
800-555-0001
Presented by motif • Source: MLS • Listed by: Frank Santino • MidState Realty, LLC • MLS# 24164730