Skip to main content

27 Lakeside Avenue

Darien, Connecticut 06820

ACTIVE - NEW$1,649,000
Beds
3
Baths
3
SqFt
2,007
Acres
0.14
Year Built
1923
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$10,710

per 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

Similar Properties

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

Listed By

Diane Farrell

(203) 984-0644

Compass Connecticut, LLC

(203) 423-3100

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.