Off Market Jun 2025 for $4.2M

$4,456,499

Est. refi paymentEst. refi $14,431/mo

•

8,835

sq ft

5 High Point Rd, Westport, CT 06880

About this home

Set on a pristine, level acre on one of Westport's most popular cul-de-sacs, this exquisite stone & shingle home combines timeless craftsmanship with modern luxury. Featuring 9' & 10' ceilings, extensive millwork, and five fireplaces with custom mantles, the home is built for elegant living and entertaining throughout nearly 9000sqft. The main level offers a chef's kitchen that flows into a warm family room with a stone fireplace and French doors to the patio, a cherry-paneled study, formal living room with marble fireplace, and a dining room that easily seats 20. Upstairs are five spacious bedrooms and four full baths, including a luxurious primary suite with 12ft ceilings, a fireplace and an oversized double shower with steam. A large playroom offers a potential in-law/au pair suite with its own bedroom and full bathroom. The finished walkout lower level includes a media room with large screen, gym, games room, a second family room with a fireplace, and full bath. The walk-up attic offers approx. 1500 sq ft for future expansion. Outside, enjoy a private backyard oasis with a heated 20x50 Gunite pool and spa (2018), new stone walls and planting beds, patio with wood-burning fireplace, and professionally landscaped evergreens and ornamentals for privacy. High Point Road is a mile-long cul-de-sac that feels like its own neighborhood, uniquely within walking distance to all three schools: award-winning Staples HS, Bedford Middle, and Long Lots Elem. Book your showing today!

Single-familyProperty Type

2007Year Built

1.06 acresLot Size

$504Est. Price/Sq.Ft.

3 car garageParking

Listed by Amy Swanson • William Raveis Real Estate

Bought with Lori Elkins Ferber • William Raveis Real Estate

Source:Smart MLS #24081110

Redfin Estimate

$4,456,499

$206K since sold in June 2025$70K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 7.4% higher than the average sale price ($4.15M) of 6 comparable homes.

SOLD JUN 30, 2026
$4,199,000
A
5 beds5.5 baths5,182 sq ft
1 Greystone Farm Ln, Westport, CT 06880
SOLD AUG 14, 2026
$4,400,000
B
6 beds5.5 baths6,775 sq ft
48 Bayberry Ln, Westport, CT 06880
SOLD JUL 20, 2026
$3,000,000
C
5 beds7 baths4,911 sq ft
22 Sturges Cmns, Westport, CT 06880
SOLD NOV 6, 2025
$3,100,000
D
5 beds6 baths8,110 sq ft
4 Jennings Ct, Westport, CT 06880
SOLD JUL 5, 2026
$4,500,000
E
5 beds7 baths8,364 sq ft
4 Peach Lot Pl Lot PL, Westport, CT 06880
SOLD AUG 7, 2026
$5,700,000
F
6 beds6 baths8,717 sq ft
6 Twin Circle Dr, Westport, CT 06880

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Earn from this home

Sell

$864,611

Est. take-home

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Refinance

Est. cash available

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Rent

$4,578/mo

Redfin rental estimate

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Market trends in 06880, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

103.6%

+1.3% MoM

Median sale price

$2.3M

$79K MoM

Avg. days on market

39d

10 days MoM

Recently sold homes

19 MoM

New listings for sale

NEW 11 HRS AGO
$5,349,000
5 beds7 baths6,503 sq ft
31 Stonybrook Rd, Westport, CT 06880
OPEN SUN, 1PM TO 3PM
$905,000
3 beds2 baths1,512 sq ft
15 Hyatt Ln, Westport, CT 06880
OPEN SUN, 1PM TO 4PM
$1,399,000
4 beds2 baths1,834 sq ft
4 Half Mile Cmn, Westport, CT 06880
OPEN SAT, 11AM TO 1PM
$2,000,000
3 beds3 baths3,810 sq ft
2 Charcoal Ln, Westport, CT 06880
OPEN SAT, 12PM TO 3PM
$4,250,000
5 beds5.5 baths7,652 sq ft
16 Rockyfield Rd, Westport, CT 06880
$2,250,000
4 beds2.5 baths2,900 sq ft
25 Bauer Pl Ext, Westport, CT 06880
$1,695,000
4 beds3.5 baths4,572 sq ft
40 Pequot Trl, Westport, CT 06880
OPEN SAT, 1AM TO 4PM
$1,850,000
6 beds3 baths3,240 sq ft
5 Aspetuck Ln, Westport, CT 06880
$875,000
3 beds2 baths1,591 sq ft
383 Main St, Westport, CT 06880
See all

Provided by Redfin

Sale history for 5 High Point Rd

Date

Event

Price

SMARTMLS #24108445

Jul 15, 2025

Rental Removed

$18,200

$2/sq ft

Jul 3, 2025

Listed for Rent

$18,200

$2/sq ft

Smart MLS #24081110

Jun 30, 2025

Sold

$4,250,000

$481/sq ft

May 2, 2025

Pending

—

May 1, 2025

Listed

$3,950,000

$447/sq ft

Apr 24, 2025

Coming Soon

$3,950,000

$447/sq ft

Public Records

Dec 4, 2017

Sold

$2,250,000

$255/sq ft

Smart MLS #99189519

Dec 4, 2017

Listing Removed

—

Dec 4, 2017

Sold

$2,250,000

$255/sq ft

Jun 21, 2017

Listed

$2,399,000

$272/sq ft

Finally the house, location, land, neighborhood & privacy (yet convenience) ALL in one neat package. 21st century luxury on a level acre on one of Westport's most desired neighborhood streets. Convenient to schools, trains and all shopping & dining destinations. Enjoy the beach and award winning schools, with design details that include Home Theatre, Study, Gym, luxurious Master Suite and stunning chef's Kitchen. Great flow and natural light. 5 Bedrooms 5 Full & 2 half baths. 3-car garage, & Room for Pool.

Smart MLS #99132009

Jun 9, 2016

Listing Removed

—

Jan 28, 2016

Listed

$2,775,000

$314/sq ft

Smart MLS #99116790

Jan 28, 2016

Listing Removed

—

Aug 20, 2015

Listed

$3,350,000

$379/sq ft

Smart MLS #99005725

Jun 28, 2013

Sold

$2,749,000

$311/sq ft

Sep 26, 2012

Listed

$2,749,000

$311/sq ft

Smart MLS #98525540

Jul 31, 2012

Listing Removed

—

Jan 19, 2012

Listed

$3,299,000

$373/sq ft

Smart MLS #98519501

Jan 2, 2012

Listing Removed

—

Nov 2, 2011

Listed

$3,299,000

$373/sq ft

Smart MLS #98324191

Mar 20, 2007

Listed

$3,195,900

$362/sq ft

Smart MLS #98318540

Feb 5, 2007

Listed

$1,150,000

$130/sq ft

Public Records

May 24, 1996

Sold

$535,000

$61/sq ft

Smart MLS #96001095

Jan 14, 1996

Listed

$549,000

$62/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$30,378 (+1.5%)

$441,800 + $1,213,700

$1,655,500

2022

$29,915

$441,800 + $1,213,700

$1,655,500

2021

$29,915 (−4.7%)

$441,800 + $1,213,700

$1,655,500

2020

$31,381 (+1.5%)

$452,600 + $1,425,400

$1,878,000

2019

$30,906

$452,600 + $1,380,500

$1,833,100

2018

$30,906

$452,600 + $1,380,500

$1,833,100

2017

$30,906

$452,600 + $1,380,500

$1,833,100

2016

$30,906 (−18.2%)

$452,600 + $1,380,500

$1,833,100

2014

$37,787

$397,400 + $1,708,900

$2,106,300

Tax history for 5 High Point Rd

Year

Property tax

Land + Additions

Assessment*

2023

$30,378 (+1.5%)

$441,800 + $1,213,700

$1,655,500

2022

$29,915

$441,800 + $1,213,700

$1,655,500

2021

$29,915 (−4.7%)

$441,800 + $1,213,700

$1,655,500

2020

$31,381 (+1.5%)

$452,600 + $1,425,400

$1,878,000

2019

$30,906

$452,600 + $1,380,500

$1,833,100

2018

$30,906

$452,600 + $1,380,500

$1,833,100

2017

$30,906

$452,600 + $1,380,500

$1,833,100

2016

$30,906 (−18.2%)

$452,600 + $1,380,500

$1,833,100

2014

$37,787

$397,400 + $1,708,900

$2,106,300

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1.06 Acres

Year renovated

—

Sq. Ft.

6,969

Year built

2007

Style

Single Family Residential

County

Fairfield County

APN

419269

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

Feb 25, 2020 • Final

Residential plumbing

Relocate the kitchen sink and dishwasher. Install a new bar sink and related plumbing fixtures.

Kitchen

Plumbing

Feb 25, 2020 • Final

Residential plumbing

Plumbing

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 3

Interior

Interior Information
Total Rooms: 15
Laundry Room Info: Upper Level
Interior Features: Audio System, Auto Garage Door Opener, Central Vacuum, Open Floor Plan, Security System
In-Law Apartment: Possible
In-Law Access: Over Garage
Fireplaces Total: 5
Cooling System: Central Air, Zoned
Appliances Included: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 2

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Foyer, Gym, Laundry Room, Mud Room
Basement Description: Full, Heated, Sump Pump, Fully Finished, Interior Access, Walk-out, Full With Walk-Out
Has Attic
Attic Description: Storage Space, Floored, Walk-up

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Shingle, Stone, Wood
Exterior Features: Underground Utilities, Gutters, Lighting, Hot Tub, Stone Wall, French Doors, Underground Sprinkler, Patio

Lot Information
Lot Description: Fence - Full, Dry, On Cul-De-Sac, Professionally Landscaped

Pool Information
Swimming Pool
Pool Description: Gunite, Heated, Auto Cleaner, Spa, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: Natural

Property Information
Waterfront Description: Beach Rights, Water Community
Radon Mitigation Air
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 6969

Financial

Assessments Information
Assessed Value: $1,655,500

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Domestic
Heat Type: Hot Air
Heat Fuel Type: Natural Gas
Energy Features: Generator, Programmable Thermostat

Location

School Information
Middle Jr High School: Bedford
High School: Staples
Elementary School: Long Lots

Location Information
State: Connecticut
Nearby Amenities: Basketball Court, Library, Medical Facilities, Playground/Tot Lot, Public Pool, Public Transportation, Shopping/Mall, Tennis Courts
Directions: Long Lots Road to High Point, 3rd house on the left
County: Fairfield

Public facts

Beds: 5
Baths: 6.0
Sq. Ft.: 6,969
Stories: 3.0
Lot Size: 1.06 acres
Style: Single Family Residential
Year Built: 2007
Year Renovated: —
County: Fairfield County
APN: 419269

Home facts updated by county records on Jul 12, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Long Lots School

Public K-5 • Assigned • 0.4mi

9/10

Bedford Middle School

Public 6-8 • Assigned • 0.8mi

9/10

Staples High School

Public 9-12 • Assigned • 0.6mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

67% chance of strong winds in next 30 years

8/10 Air Factor

13 unhealthy days expected this year, 18 days in 30 years

Provided by First Street

Historical weather

Westport, CT • 06880

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.23M – $5.13M

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Home values near 5 High Point Rd

Data from public records.

Address	Redfin Estimate
8 High Point Road, Westport, CT 5 Beds \| 5 Baths \| 5716 Sq. Ft.	$2,348,979
7 High Point Road, Westport, CT 3 Beds \| 4 Baths \| 2910 Sq. Ft.	$2,237,645

Address	Redfin Estimate
9 High Point Road, Westport, CT 6 Beds \| 8.5 Baths \| 10000 Sq. Ft.	$5,717,319
2 High Point Road, Westport, CT 6 Beds \| 6 Baths \| 6832 Sq. Ft.	$3,557,660

Address	Redfin Estimate
14 High Point Road, Westport, CT 5 Beds \| 5.5 Baths \| 4694 Sq. Ft.	$3,572,433
3 High Point Road, Westport, CT 4 Beds \| 4.5 Baths \| 3554 Sq. Ft.	$2,882,351

Property information provided by Smart MLS when last listed in 2025. This data may not match . Learn more.

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