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91 Rolling Wood Drive

Stamford, Connecticut 06905

ACTIVE - NEW$899,000
Beds
3
Baths
2 | 1
SqFt
1,884
Acres
0.28
Year Built
1958
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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1-Car Garage1 Fireplace

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

City/Town
Stamford
Neighborhood
Newfield
Property / Style
Single Family · Split Level
Year Built
1958
Days on Market
0 days
Beds
3
Baths
2 full · 1 half
Living Area
1,884 sq ft
Lot Size
0.28 acres
Garage / Parking
1 garage · 5 total
Property Taxes
$10,766 / Annually

Market Snapshot

The Stamford Market

Single Family · trailing 12 months

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,098

per 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

City/Town
Stamford
Neighborhood
Newfield
County
Fairfield

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

Similar Properties

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Listed By

Todd Auslander

(203) 918-8174

Keller Williams Prestige Prop.

(203) 327-6700

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.