91 Rolling Wood Drive
Stamford, Connecticut 06905
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 1,884
- Acres
- 0.28
- Year Built
- 1958
- Neighborhood
- Newfield
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Welcome to this beautifully maintained 3-bedroom, 2.5-bath split-level home on a quiet street in desirable Pepper Ridge, centrally located in Stamford. Hardwood floors and an inviting open layout create a warm, welcoming feel, while the beautifully updated kitchen flows seamlessly into the dining and living areas, featuring a fireplace and vaulted ceilings. The upper level offers a spacious primary bedroom with a full bath and walk-in closet, along with two additional bedrooms and a second full bath. The entry level features a welcoming foyer, a comfortable family room, a half bath, and a versatile bonus space ideal for a home office, gym, or hobby room. The fully finished, walkout lower level provides additional living space, complete with a dedicated laundry room. Outside, enjoy the large deck overlooking a private, level, fully fenced backyard-perfect for entertaining, relaxing, or enjoying time outdoors. An attached garage adds everyday convenience. Ideally situated close to downtown Stamford, shopping, grocery stores, restaurants, schools, parks, and everyday amenities, this inviting home combines comfortable living with a convenient location in a sought-after neighborhood.
Key Facts
Market Snapshot
The Stamford Market
Single Family · trailing 12 months
Active Listings
96
99 under contract
Median List Price
$1.10M
96 active listings
Median Closed Price
$975,000
573 sales
Median Days on Market
37
96 active listings
Median $ / Sq Ft
$418
96 active listings
Sale-to-List Ratio
104.1%
573 sales
How this home compares
List Price
$899,000
vs $1.10M median
18.2% below median
Price / Sq Ft
$477
vs $418 median
14.1% above median
Days on Market
0 days
vs 37 days median
37 days fresher than median
Based on 96 active and 573 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of October 29, 2026.
Location
91 Rolling Wood Drive, Stamford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$4,901
- Property Taxes$897
- Insurance$300
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
Residence
- Property Type
- Single Family
- Style
- Split Level
- Year Built
- 1958
- New Construction
- No/Resale
- Living Area
- 1,884 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Gas RangeMicrowaveRefrigeratorDishwasher
- Basement
- FullFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor Plan
Exterior & Lot
- Lot Size
- 0.28 acres
- Zoning
- R10
- Garage / Parking
- 1 garage space5 total parking spacesAttached GaragePavedDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl SidingBrick
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- PorchDeckGutters
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $10,766 / Annually
- Days on Market
- 0
- MLS #
- 24217059
- MLS Status
- Active
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Co-Listed By
Joshua Caldwell
Keller Williams Prestige Prop.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/29/2026. 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 10/29/2026 at 8:50 PM UTC.