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75 Halliwell Drive

Stamford, Connecticut 06902

ACTIVE - NEW$1,475,000
Beds
4
Baths
2 | 1
SqFt
2,604
Acres
0.22
Year Built
1939
Matt Caiola

Matt Caiola

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1-Car Garage1 Fireplace

About This Home

Nestled in Westover's coveted Hycliff Association, this four-bedroom, two-and-a-half-bath Colonial exudes timeless curb appeal while offering an expansive, highly versatile multi-level layout. Move in ready and full of historic soul, a warm entry foyer opens to a gracious living room anchored by a gas fireplace, classic built-ins, and a cozy sunroom. Entertaining flows seamlessly into the formal dining room with bay window and an updated kitchen complete with a Viking six-burner gas range, breakfast bar, and casual dining area. Through the sliders, access a private backyard retreat featuring a large slate patio, retaining walls, and stairs leading to a level upper yard. An expansive family room with custom built-ins, an updated powder room, and entry to the attached garage complete the main level. Upstairs, explore a vast primary suite with an expansive bedroom, an oversized walk-in closet, and a double-vanity bath, with the unique potential to incorporate the adjacent bedroom and sitting room into a grand private wing. Two additional generous bedrooms, a walk-up attic, and a hallway bath offer endless utility. The lower level includes an unfinished basement for abundant storage. Enjoy unmatched community perks with access to the Hycliff Association pool, tennis courts, basketball court, and playground. Ideally located minutes from downtown Stamford, Harbor Point, golf courses, and commuting options.

Key Facts

City/Town
Stamford
Neighborhood
Westover
Property / Style
Single Family · Colonial
Year Built
1939
Days on Market
0 days
Beds
4
Baths
2 full · 1 half
Living Area
2,604 sq ft
Lot Size
0.22 acres
Garage / Parking
1 garage
Property Taxes
$16,482 / Annually
HOA Fee
$1,200 / Annually

Market Snapshot

The Stamford Market

Single Family · trailing 12 months

View area

Median Days on Market

37

98 active listings

Median $ / Sq Ft

$411

98 active listings

Sale-to-List Ratio

104.1%

569 sales

How this home compares

List Price

$1.48M

vs $1.25M median

18.0% above median

Price / Sq Ft

$566

vs $411 median

37.7% above median

Days on Market

0 days

vs 37 days median

37 days fresher than median

Based on 98 active and 569 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of October 30, 2026.

Location

75 Halliwell Drive, Stamford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$10,008

per month

  • Principal & Interest$8,042
  • Property Taxes$1,374
  • Insurance$492
  • HOA$100

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Stamford
Neighborhood
Westover
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1939
New Construction
No/Resale
Living Area
2,604 sq ft

Schools

Elementary
Stillmeadow
High
Westhill

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Laundry Location
Basement
Appliances
Gas RangeRange HoodRefrigeratorDishwasherWasherDryer
Basement
Crawl SpacePartialUnfinished
Interior Features
Auto Garage Door OpenerCable - Pre-wiredSecurity System

Exterior & Lot

Lot Size
0.22 acres
Zoning
R10
Garage / Parking
1 garage spaceAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Shingle
Color
White
Roof
Asphalt Shingle
Foundation
Block
Lot Description
Lightly WoodedRolling

HOA / Association

Fee
$1,200 / Annually
Amenities
Tennis CourtsPlayground/Tot LotPool

Listing & Financials

Property Taxes
$16,482 / Annually
Days on Market
0
MLS #
24218154
MLS Status
Active

Similar Properties

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Listed By

Maureen Kitson

(914) 552-1063

William Pitt Sotheby's Int'l

(203) 968-1500

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 10/30/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 10/30/2026 at 8:16 PM UTC.