Sold
Last Sold Price
4 beds2,219 sqft$241/sqft
39 Highland Rd, Westport, CT 06880
Single FamilyProperty Type
1.19 acresLot Size
1952Year Built
$241/sq ftPrice per sq ft
2 carsParking Spaces

Description

Spacious, Cozy & Warm Best Describes This 4 Bedroom Home On Over An Acre At End Of Cul-De-Sac. Recently Renovated, This Home Has A Large Living Room W/Fireplace, Screened Porch Off Formal Living Room, Eat-In Kitchen And Family RoomSpacious, Cozy & Warm Best Describes This 4 Bedroom Home On Over An Acre At End Of Cul-De-Sac. Recently Renovated, This Home Has A Large Living Room W/Fireplace, Screened Porch Off Formal Living Room, Eat-In Kitchen And Family Room
  • Listed by: Bernice Grey 203.858.1798 bernice.grey@raveis.com • Higgins Group Bedford Square
Listing closed: 07/14/2000 12:00 AM • Source: SMARTMLS, MLS#: 98068964

Recent comparable sales

Median sold price

$1,475,000

Avg days on market

28

Sale-to-list ratio

101.8%

Westport, CT

9 comparable properties found

$1,751,000 | 7 Morningside Lane, Westport, CT 06880
1

$1,751,000

Sold 12/12/25

4
Bedrooms
2,190
Square Feet
0.56
Acres
$1,492,500 | 4 Turtleback Lane, Westport, CT 06880
2

$1,492,500

Sold 06/26/25

4
Bedrooms
2,134
Square Feet
0.5
Acres
3

$1,475,000

Sold 07/06/26

4
Bedrooms
2,556
Square Feet
2.07
Acres
$969,000 | 20 Woods Grove Road, Westport, CT 06880
4

$969,000

Sold 08/07/26

4
Bedrooms
1,941
Square Feet
0.3
Acres
$1,020,000 | 15 West Parish Road, Westport, CT 06880
5

$1,020,000

Sold 10/01/25

4
Bedrooms
1,930
Square Feet
0.4
Acres
$637,500 | 10 Crescent Park Road, Westport, CT 06880
6

$637,500

Sold 10/31/25

4
Bedrooms
1,152
Square Feet
0.12
Acres
$1,300,000 | 9 Loren Lane, Westport, CT 06880
7

$1,300,000

Sold 12/16/24

4
Bedrooms
2,241
Square Feet
0.29
Acres
$1,550,000 | 17 Loren Lane, Westport, CT 06880
8

$1,550,000

Sold 06/26/26

4
Bedrooms
2,000
Square Feet
0.34
Acres
$1,560,000 | 157 North Avenue, Westport, CT 06880
9

$1,560,000

Sold 07/21/25

4
Bedrooms
2,641
Square Feet
1.21
Acres

Location

Listing Courtesy of Higgins Group Bedford Square, Bernice Grey
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Payment Calculator

$3,053 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,719

Property Taxes

$333

HOA Dues

$0

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Property Information for 39 Highland Road

Property Details
  • Taxes: $3,998 / year
  • MLS Type: Residential
  • Basement Description: Full, Garage Access, Partially Finished, Storage, Sump Pump
  • Direct Waterfront: No
  • Garages Number: 2
  • Style: Split Level
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
Building Information
  • Year Built: 1952
  • Lot Size: 1.19 AC / 51,836 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Bayberry Ln To Highland (At End Of Cul-De-Sac)
  • Elementary School: COLEYTOWN
  • High School: STAPLES
  • Latitude: 41.174522
  • Longitude: -73.32877
  • Middle Jr High School: COLEYTOWN
  • State: Connecticut
HOA and Fees
  • HOA Fee Amount: 0
  • Home Owner's Assocation: No
  • Tax Year: July 1998-June 1999
  • Property Tax: $3,998
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Dishwasher, Dryer, Oven/Range, Refrigerator, Wall Oven, Washer
  • Cooling System: Attic Fan, Window Unit
  • Heat Type: Baseboard, Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Laundry Room Location: Ll
  • Room Count: 8
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Hardwood Floor
  • Room Length: 10.11
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.0
Room 2
  • Room Entry Order: 10
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 14.7
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 11.0
Room 3
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.2
Room 4
  • Room Entry Order: 3
  • Room Features: Hardwood Floor
  • Room Length: 20.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.11
Room 5
  • Listing Key: DD63D0E83419676FE053D501100A75F5
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Length: 10.8
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 14.0
Room 6
  • Room Entry Order: 7
  • Room Features: Wall/Wall Carpet
  • Room Length: 18.0
  • Room Level: Lower
  • Room Type: Family Room
  • Room Width: 15.0
Room 7
  • Room Entry Order: 8
  • Room Features: Eating Space,Hardwood Floor,Tile Floor
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 11.0
Room 8
  • Room Entry Order: 9
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 19.9
Property
Property and Assessments
  • Color: TAUPE
  • Exterior Siding: Cedar, Shake
  • Foundation Type: Block
  • Gross SQFT Per Public Records: 5518
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Sq Ft Source: Approximate
  • Year Built: 1952
  • Year Built Source: Public Records
  • Living Area SQFT Per Public Records: 2947
Lot Information
  • Documents Available: Property Disclosure
  • Lot Description: On Cul-De-Sac, Level Lot, Treed, Fence - Partial, Fence - Stone
  • Parcel Number: 410243
  • Sq Ft Est Heated Above Grade: 2219.0
  • Sq Ft Total: 2219.0
  • Zoning: AAA
Utilities
  • Energy Features: Storm Doors, Storm Windows
  • Heat Fuel Type: Oil
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Total Unit Count: 0

Property History for 39 Highland Road

DateEvent & SourcePriceAppreciation
Jul 14, 2000

Closed (Public Record)

Public Record #91300055

$535,000

+21.8% / yr

Jan 22, 1999

Closed (Public Record)

Public Record #91302168

$400,000
DateEvent & SourcePrice
07/14/2000

Closed (Public Record)

Public Record #91300055

$535,000

+21.8% / yr

01/22/1999

Closed (Public Record)

Public Record #91302168

$400,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 39 Highland Road

Taxable ValueLand$456,500Additions$274,200Total$730,700
Tax Record2025$13,781 ($1,148 / month)
Home Facts
Beds4Baths3Total Finished SqFt2,947 SqFtAbove Grade Finished SqFt2,947 SqFtUnfinished Basement SqFt506 SqFtStories2Lot Size51,836 SqFtStyleSingle Family ResidenceYear Built1952Year Renovated1952ZoningAAACountyWESTERN CONNECTICUTAPNWPRT M:F15 L:048-000

Schools near 39 Highland Road

This home is within Westport School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Coleytown Elementary School
PublicK to 5

Coleytown Middle School
Public6 to 8

Staples 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.

Westport
Westport
A magnificent, scenic coastal town. Westport was formerly known as ‘Green’s Farm’ due to the farming families that settled there. By the 19th century, the town turned into a bustling shipping center and transformed by the 20th century into a destination for artists, musicians and writers. Residents...

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 39 Highland Road, Westport, CT 06880
$535,000
4
2,219
51,836
$2,425,000
5
6,600
46,173
$2,350,000
5
6,000
43,560
$2,500,000
5
6,000
43,560
4
3.5
2,480
43,560
$3,100,000
6
7,520
46,609

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 Higgins Group Bedford Square, Bernice Grey

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.