269 Academy Road - Cheshire, CT

$699,500

Beds

3.00

Baths

3,070

SqFt

0.96

Acres

Pricing Insight: Originally listed for $789,900, the price was last adjusted to $699,500 on July 21, 2026, a –$90,400 (11.4%) change, approximately 0 days ago. This property has been on the market for approximately 106 days. MLS reports 37 Days on Market (DOM) before it went under contract.

269 Academy Road, Cheshire, CT is a 4-bed, 3-bath, 3,070 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: $699,500

Residence Type: Single Family

Architectural Style: Cape Cod

Living Area: 3,070 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: $228

Estimated Tax: $10,576

Days on Market: 37

$1,299,000

4 Beds · 4 Baths · 4,016 Sq Ft

3 Melrose Drive, Cheshire

$1,395,000

4 Beds · 4 Baths · 3,423 Sq Ft

5 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

$1,300,000

4 Beds · 5 Baths · 4,379 Sq Ft

15 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: $228 / 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: 3,070 Sq. Ft.

Lot Size: 0.96 Acres

Fuel: Oil

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AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

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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: 46

Average Price: $480,599

Average DOM: 37 days

Complimentary CMAs, no obligation

Discover this beautifully expanded Cape, perched high above the street on a private, nearly one-acre lot - minutes from the heart of Cheshire. Offering 2,755 sq ft, this home boasts hardwood floors throughout and a flexible open floor plan for one-level living while providing three finished levels to suit your lifestyle. The sun-filled living room with a wood-burning fireplace flows into a stylish gourmet kitchen featuring stainless steel appliances, granite countertops and a center island. The kitchen opens into 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 315 sq ft of living space, a 2nd wood-burning fireplace and plenty of room to relax or entertain. Upstairs, you'll find two expansive bedrooms, both featuring their own full bath and walk-in closet. The tranquil backyard features a two-level deck ideal for unwinding, a fire pit and a fully fenced yard for added privacy & security. Abundant storage throughout including a 2-car attached garage, 1,317 sq ft of basement space, and generous closets. Among the many upgrades are a new driveway(2023), 30-yr architectural roof(2021), paver front walkway(2022), 5-zone boiler and dual central air systems(2018) & generator-ready since 2024. Schedule your 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.

46

Homes For Sale

$480,599

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"

Steve Simos

Real Estate Advisor

Cheshire • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(800) 555-0003

george@appzentric.com

Good afternoon Steve, I'm interested in
269 Academy Road, Cheshire, Connecticut

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