253 Middlesex Road
Description
- Listed by: Taylor I. Tait • HOULIHAN LAWRENCE NCA
Recent comparable sales
Median sold price
$4,250,000
Avg days on market
21
Sale-to-list ratio
105.6%
Darien, CT
9 comparable properties found
$4,425,000
Sold 12/18/25
- 5
- Bedrooms
- 6
- Bathrooms
- 8,938
- Square Feet
- 1.06
- Acres
$4,350,000
Sold 12/15/25
- 5
- Bedrooms
- 6
- Bathrooms
- 6,135
- Square Feet
- 0.94
- Acres
$3,525,000
Sold 07/08/25
- 5
- Bedrooms
- 6
- Bathrooms
- 7,446
- Square Feet
- 0.52
- Acres
$5,625,000
Sold 07/24/26
- 5
- Bedrooms
- 7
- Bathrooms
- 9,039
- Square Feet
- 2
- Acres
$3,550,000
Sold 12/17/25
- 5
- Bedrooms
- 6
- Bathrooms
- 5,356
- Square Feet
- 0.35
- Acres
$4,400,000
Sold 07/01/25
- 5
- Bedrooms
- 6
- Bathrooms
- 5,328
- Square Feet
- 1.18
- Acres
Location
Payment Calculator
$26,155 per month
30 year fixed, 6.55% Interest
$22,355
$3,801
$0
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1Property Information for 253 Middlesex Road
- Taxes: $45,610 / year
- MLS Type: Residential
- County: Fairfield County
- Town: Darien
- Style: Colonial
- Basement: Full
- Garage #: 5
- Garage Description: Attached
- Pool: Yes
- Pool Description: In Ground - Heated
- Stories: 2
- Year Built: 2007
- Lot Size: 1.05 AC / 45,738 SF
- Directions: Middlesex Road to Libby Lane. 253 Middlesex is the first home on the right on Libby Lane.
- Elementary School: Ox Ridge
- Middle School: Middlesex
- High School: Darien
- Equipment Included: Dishwasher, Washer, Standard Oven, Security System, Refrigerator, Range, Microwave, Central Vac, Cable TV Conn, Dryer
- Mechanical Features: Auto Garage Door Opener, Security System, Sprinkler System, Generator, Central Vac
- House Color: Beige
- Mill Rate: $18
- Possession: Negotiable
- Property Also for Rent: No
- Garage: Attached
- Lot Description: Corner, Level
- Parcel Number: 09060
- Waterfront: No
- Zoning: R-1
- Assessed Value: $3,010,910
- Assessment - Building: $2,238,250
- Assessment - Land: $772,660
- Amenities: Heated Pool, Generator, Wet Bar, Terrace, Wine Cellar, Rear Stairs, Pool Spa, Lawn Sprinkler
- SqFt Source: Town
- Water: Public Connected
- Cooling: Central Air
- Air Conditioning: Central
- Heat Zone: 6+
- Heating: Baseboard, Radiant, Hot Air, Other, FHA
- Water Heater: Boiler
- Fuel: Oil, Propane
- Sewer: Public Connected
- Cable: Yes
- Exterior: Shingle, Wood, Stone
- Exterior Features: Balcony, Outbuilding, Guest
- Porch: Open
- Swimming Pool: Heated, In-Ground
- Exclusions: Please see addendum
- Inclusions: Please see addendum
- Rooms: 10
- Living Room: Fireplace, Formal
- Living Room: Dimensions: 24x18
- Bedroom 2: Built-Ins, Upper, Full Bath
- Bedroom 2: Dimensions: 16x14
- Bedroom 3: Built-Ins, Upper, Full Bath
- Bedroom 3: Dimensions: 16x14
- Bedroom 4: Built-Ins, Upper, Walk-In, Full Bath
- Bedroom 4: Dimensions: 18x14
- Bedroom 5: Full Bath, Walk-In, Upper
- Dining Room: Bay, Formal
- Dining Room: Dimensions: 20x18
- Family Room: Fireplace, First Level
- Family Room: Dimensions: 25x18
- Kitchen: Breakfast Bar, Pantry, Island, Eat-In, Cathedral Ceiling
- Kitchen: Dimensions: 20x14
- Laundry Location: First, Upper
- Additional Rooms: Breakfast Room, Playroom, Office, Mudroom, Library, Great Room, Game Room, Exercise Room
- Additional Rooms: Mudroom Dimensions: 11x14
- Additional Rooms: Office Dimensions: 22x23
- Additional Rooms: Playroom Dimensions: 32x18
- Flooring: Hardwood, Ceramic Tile
- Interior Features: Balcony, Wet Bar, French Doors, Foyer
- Roof: Wood
- Walls: Dry Wall
- Windows: Thermal
- Additional SqFt: 1100.0
- Addl Exterior Feats: Patio, Terrace, Porch
- Appliances Included: Dishwasher, Wall Oven, Washer, Refrigerator, Microwave, Oven/Range, Freezer, Dryer
- Attic: Unfinished, Walkup
- Basement Finish: Full Finished
- Room Type: Living Room
- Room Level: Main
- Level: 1
- Room Type: Dining Room
- Room Level: Upper
- Level: 1
- Room Type: Family Room
- Room Level: Upper
- Level: 1
- Room Type: Kitchen
- Room Level: Lower
- Level: 1
- Room Type: Library
- Room Level: Main
- Level: 1
- Room Type: Primary Bedroom
- Room Level: Main
- Level: 2
- Room Type: Bedroom 2
- Room Level: Main
- Level: 2
- Room Type: Bedroom 3
- Room Level: Main
- Level: 2
- Room Type: Bedroom 4
- Room Level: Upper
- Level: 2
- Room Type: Bedroom 5
- Room Level: Upper
- Level: 2
- Room Type: Great Room
- Room Level: Upper
- Level: 2
- Room Type: Rec Rm
- Room Level: Upper
- Level: L
- Oil Tank: Basement
Property History for 253 Middlesex Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Aug 12, 2024 | Closed (Public Record) Public Record #1538933464 | $4,398,000 | +7.7% / yr |
| Mar 5, 2007 | Closed (Public Record) Public Record #216363774 | $1,200,000 | +9.8% / yr |
| Jul 30, 1992 | Closed (Public Record) Public Record #90945729 | $305,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 08/12/2024 | Closed (Public Record) Public Record #1538933464 | $4,398,000 +7.7% / yr |
| 03/05/2007 | Closed (Public Record) Public Record #216363774 | $1,200,000 +9.8% / yr |
| 07/30/1992 | Closed (Public Record) Public Record #90945729 | $305,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 253 Middlesex Road
Schools near 253 Middlesex Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
Royle Elementary School PublicPK to 5 | ||
Middlesex Middle School Public6 to 8 | ||
Darien High School Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
Neighborhood Map and Transit
Similar Homes
New listings in 06820
Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 253 Middlesex Road, Darien, CT 06820 | $4,398,000 | 5 | 6 | 9,033 | 45,738 |
$6,100,000 | 6 | 9 | 8,552 | 46,173 | |
$1,360,000 | – | – | – | 46,173 | |
$2,601,000 | 5 | 5 | 4,809 | 53,143 | |
$3,200,000 | 5 | 6 | 6,647 | 51,836 | |
$430,000 | 4 | 4.5 | 4,699 | 43,560 | |
$440,000 | 5 | 6 | 9,411 | 154,638 | |
– | 3 | 1.5 | 1,995 | 45,302 | |
$995,000 | – | – | – | 45,302 | |
$725,000 | 4 | 1.5 | 2,475 | 47,916 | |
– | – | – | – | 53,143 | |
$2,700,000 | 6 | 8 | 6,679 | 18,730 | |
$3,325,000 | 5 | 7 | 6,392 | 43,560 | |
$1,800,000 | 5 | 4 | 4,252 | 14,374 | |
$1,604,500 | 4 | 3 | 3,360 | 43,560 |
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Listing Courtesy of HOULIHAN LAWRENCE NCA, Taylor I. Tait
Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.