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86 Rolling Wood Drive

Stamford, Connecticut 06905

COMING SOON - NEW$899,000
Beds
3
Baths
2 | 1
SqFt
2,094
Acres
0.17
Year Built
1958
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Welcome to 86 Rolling Wood, a home where contemporary comfort meets effortless style. Close to town/train, yet tucked away in a quiet neighborhood, this home represents the best of suburban living. From the moment you pull up the freshly resealed horseshoe driveway, it's clear this property has been maintained with an eye for detail and a commitment to quality. Step inside to discover a bright, inviting interior highlighted by a kitchen that truly shines. With a suite of recent upgrades, including gas range, refrigerator, dishwasher, and refinished floors, this space is as functional as it is beautiful. The thoughtful improvements continue throughout the home, including the convenience of a brand-new washer and dryer. Peace of mind comes standard here, thanks to significant mechanical updates. With a newly installed furnace and a new central A/C system, you can enjoy crisp cooling all summer and cozy warmth all winter. The newly floored basement adds additional flex space for office or recreation. The exterior is equally impressive, with flat yard featuring newly installed rear fencing that adds a clean, polished look to the outdoor space. This is a rare opportunity to move into a home where the heavy lifting has already been done for you. This desirable location between 95 and 15 make for seamless commuting as well as proximity to every amenity you can think of. 86 Rolling Wood is ready for its next chapter-come see how easy life can be when every detail is already in pla

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
2,094 sq ft
Lot Size
0.17 acres
Garage / Parking
2 garage
Property Taxes
$10,240 / Annually

Market Snapshot

The Stamford Market

Single Family · trailing 12 months

View area

Median Days on Market

40

87 active listings

Median $ / Sq Ft

$419

87 active listings

Sale-to-List Ratio

104.1%

573 sales

How this home compares

List Price

$899,000

vs $1.09M median

17.9% below median

Price / Sq Ft

$429

vs $419 median

In line with median

Days on Market

0 days

vs 40 days median

40 days fresher than median

Based on 87 active and 573 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of October 20, 2026.

Location

86 Rolling Wood Drive, Stamford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,133

per month

  • Principal & Interest$4,980
  • Property Taxes$853
  • 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
2,094 sq ft

Schools

Elementary
Davenport Ridge
High
Stamford

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
Full

Exterior & Lot

Lot Size
0.17 acres
Zoning
R10
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Access
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Aluminum
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Level Lot

Listing & Financials

Property Taxes
$10,240 / Annually
Days on Market
0
MLS #
24215573
MLS Status
Coming Soon

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

AJ Letterman

(203) 218-0604

Compass Connecticut, LLC

(203) 343-0141

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/20/2026. 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 10/20/2026 at 6:15 AM UTC.