86 Rolling Wood Drive
Stamford, Connecticut 06905
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,094
- Acres
- 0.17
- 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 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
Market Snapshot
The Stamford Market
Single Family · trailing 12 months
Active Listings
87
100 under contract
Median List Price
$1.09M
87 active listings
Median Closed Price
$975,000
573 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per 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
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
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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 10/20/2026. 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.