75 Halliwell Drive
Stamford, Connecticut 06902
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,604
- Acres
- 0.22
- Year Built
- 1939
- Neighborhood
- Westover
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Market Snapshot
The Stamford Market
Single Family · trailing 12 months
Active Listings
98
97 under contract
Median List Price
$1.25M
98 active listings
Median Closed Price
$975,000
569 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per 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
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
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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.