27 Lakeside Avenue
Darien, Connecticut 06820
- Beds
- 3
- Baths
- 3
- SqFt
- 2,007
- Acres
- 0.14
- Year Built
- 1923
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
A rare opportunity to live on Tilley Pond Park - with stunning park and water views, on a coveted street that offers a lifestyle like no other. This storybook blend of scenic beauty and coastal charm offers an idyllic walk to all, with newly expanded shopping and restaurants of downtown Darien and the train just steps away. Have it all with beautiful nearby beaches and award-winning schools. Take in one of Darien's most picturesque locations every day, from the ultimate place to curl up with a book or a morning coffee - your enchanting, heated front porch with wrap-around windows. Or choose a cozy spot in front of your beautiful living room fireplace. Everyday living and entertaining are a breeze with a bright and spacious open first floor that also includes a family room with built-ins and dining room with bay window. The newer kitchen with vaulted ceiling, Wolf range and breakfast bar has Carrera marble counters, heated floors and sliders to a generous bluestone patio, perfect for outdoor dining. The level fenced-in yard offers privacy, professionally maintained mature plantings and handy garden shed. A convenient first floor bedroom and full bath complete the first level. Find two more bedrooms on the second floor of this romantic cottage-style home, including a large sunny primary bedroom with skylight, walk-in closet and full bath. The finished lower level provides even more living space with another full bath, a recreation room with built-ins, laundry & generous storage
Key Facts
- City/Town
- Darien
- Neighborhood
- N/A
- Property / Style
- Single Family · Cottage
- Year Built
- 1923
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 3 full
- Living Area
- 2,007 sq ft
- Lot Size
- 0.14 acres
- Garage / Parking
- 4 total
- Property Taxes
- $12,309 / Annually
Market Snapshot
The Darien Market
Single Family · trailing 12 months
Active Listings
27
25 under contract
Median List Price
$3.85M
27 active listings
Median Closed Price
$2.87M
213 sales
Median Days on Market
50
27 active listings
Median $ / Sq Ft
$773
27 active listings
Sale-to-List Ratio
106.3%
213 sales
How this home compares
List Price
$1.65M
vs $3.85M median
57.2% below median
Price / Sq Ft
$822
vs $773 median
6.3% above median
Days on Market
0 days
vs 50 days median
50 days fresher than median
Based on 27 active and 213 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of October 9, 2026.
Location
27 Lakeside Avenue, Darien, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$9,134
- Property Taxes$1,026
- Insurance$550
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Darien
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Cottage
- Year Built
- 1923
- New Construction
- No/Resale
- Living Area
- 2,007 sq ft
- Below Grade
- 450 sq ft
Schools
- Elementary
- Royle
- High
- Darien
Interior
- Heating
- Hot WaterRadiantRadiatorZoned
- Heat Fuel
- ElectricOil
- Cooling
- Ceiling FansSplit SystemWall Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Gas RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullSump PumpStorageInterior AccessPartially FinishedLiveable Space
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 0.14 acres
- Zoning
- R13
- Garage / Parking
- 4 total parking spacesPavedDrivewayPrivatePavedAsphalt
- Waterfront Details
- Walk to WaterView
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Shingle
- Color
- Light Gray
- Roof
- Asphalt Shingle
- Foundation
- MasonryStone
- Exterior Features
- Porch-HeatedPorch-EnclosedShedPorchLightingUnderground SprinklerPatio
- Lot Description
- Level LotProfessionally LandscapedWater View
Listing & Financials
- Property Taxes
- $12,309 / Annually
- Days on Market
- 0
- MLS #
- 24211645
- MLS Status
- Active
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Co-Listed By
Maureen DeBoisbriand
Compass Connecticut, LLC
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/9/2026. 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 10/9/2026 at 10:30 PM UTC.