99 Hillspoint Road

Closed 8/7/25
Closed 8/7/25
Gallery Image 1
Sold
Last Sold Price
$3,300,000
5 beds6,027 sqft$548/sqft
99 Hillspoint Rd, Westport, CT 06880
Single FamilyProperty Type
1.28 acresLot Size
2022Year Built
$548/sq ftPrice per sq ft
2 carsParking Spaces

Description

This better than new modern farmhouse nestled on 1.28 acres is a masterpiece of architectural design and sophistication and just steps from the beach, train, and shopping. Every detail of this 6,000 SF 5 Bedroom home has been meticulously curated, from the high-end materials to the advanced technology offering a modern, refined aesthetic to deliver unparalleled comfort. The double-height entry leads to open, light filled interiors, featuring expansive glass walls that seamlessly blend indoor & outdoor...This better than new modern farmhouse nestled on 1.28 acres is a masterpiece of architectural design and sophistication and just steps from the beach, train, and shopping. Every detail of this 6,000 SF 5 Bedroom home has been meticulously curated, from the high-end materials to the advanced technology offering a modern, refined aesthetic to deliver unparalleled comfort. The double-height entry leads to open, light filled interiors, featuring expansive glass walls that seamlessly blend indoor & outdoor living. Stunning spaces on the main floor exceed every expectation, especially the Great Room with its cathedral ceiling and walls of glass that infuse the space with a sense of calm. The Kitchen is a sleek and modern central space with an oversized show-stopping marble island. An adjoining Butler's Pantry is equally well-equipped. A chic Dining Room, two stylish Bedrooms and Laundry complete the floor. A Zen-like Primary Suite anchors upstairs with a spa-like Bath, custom walk-in closets, additional ensuite Bedroom, Den, flexible Rec space and half Bath. A Lounge area and Bedroom/Home Office above has expansive views. Downstairs includes a Bedroom, Playroom, Gym, and Mudroom. Complementing the exceptionally chic and ethereal vibe within, the professionally landscaped exterior features a hot tub, outdoor loggia, and entertainment areas, perfect for enjoying the serene surroundings. Mature trees, manicured lawns, and stunning views complete this idyllic property.
  • Listed by: Susan Lieberman 203.858.9411 suelieberman@yahoo.com • The Riverside Realty Group
  • Listed by: Justine Fink 203.226.8300 justinebfink@gmail.com • The Riverside Realty Group
Listing closed: 08/07/2025 12:00 AM • Source: SMARTMLS, MLS#: 24091976

Recent comparable sales

Median sold price

$3,150,000

Avg days on market

32

Sale-to-list ratio

99.9%

Westport, CT

9 comparable properties found

$2,700,000 | 2 Ledgemoor Lane, Westport, CT 06880
1

$2,700,000

Sold 08/21/26

5
Bedrooms
5,739
Square Feet
1.16
Acres

2 Ledgemoor Lane, Westport, CT 06880

$3,150,000 | 55 Center Street, Westport, CT 06880
2

$3,150,000

Sold 08/21/26

5
Bedrooms
4,922
Square Feet
1
Acres

55 Center Street, Westport, CT 06880

$2,815,000 | 4 Reimer Road, Westport, CT 06880
3

$2,815,000

Sold 09/09/25

5
Bedrooms
5,311
Square Feet
1
Acres

4 Reimer Road, Westport, CT 06880

$3,200,000 | 19 Horseshoe Lane, Westport, CT 06880
4

$3,200,000

Sold 07/15/26

5
Bedrooms
5,476
Square Feet
0.26
Acres

19 Horseshoe Lane, Westport, CT 06880

$2,995,000 | 221 Greens Farms Road, Westport, CT 06880
5

$2,995,000

Sold 08/05/26

5
Bedrooms
5,789
Square Feet
2.33
Acres

221 Greens Farms Road, Westport, CT 06880

a front view of a house with a yard
6

$2,465,000

Sold 03/25/25

5
Bedrooms
4,942
Square Feet
0.28
Acres

7 West Parish Road, Westport, CT 06880

$3,450,000 | 5 Elwil Drive, Westport, CT 06880
7

$3,450,000

Sold 07/30/25

5
Bedrooms
5,887
Square Feet
1.08
Acres

5 Elwil Drive, Westport, CT 06880

$3,700,000 | 5 Timber Lane, Westport, CT 06880
8

$3,700,000

Sold 04/15/25

5
Bedrooms
5,273
Square Feet
1.68
Acres

5 Timber Lane, Westport, CT 06880

$3,327,000 | 147 Cross Highway, Westport, CT 06880
9

$3,327,000

Sold 03/31/25

5
Bedrooms
6,190
Square Feet
1.01
Acres

147 Cross Highway, Westport, CT 06880

Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of The Riverside Realty Group, Susan Lieberman; The Riverside Realty Group, Justine Fink

Sold By Houlihan Lawrence, Amanda Spatola

Add your commute

Payment Calculator

Get preapproved with Rocket Mortgage1

$19,274 per month

30 year fixed, 6.55% Interest

Principal and Interest

$16,774

Property Taxes

$2,500

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 99 Hillspoint Road

Property Details
  • Taxes: $30,002 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Full, Garage Access, Partially Finished, Walk-out, Liveable Space
  • Direct Waterfront: No
  • Garages Number: 2
  • Neighborhood: Hillspoint
  • Style: Farm House, Modern
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
Building Information
  • Year Built: 2022
  • Lot Size: 1.28 AC / 55,756 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Greens Farms Road to Hillspoint
  • Elementary School: Greens Farms
  • High School: Staples
  • Latitude: 41.126137
  • Longitude: -73.34393
  • Middle Jr High School: Bedford
  • Neighborhood Amenities: Basketball Court, Golf Course, Health Club, Library, Medical Facilities, Public Pool, Public Rec Facilities
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $30,002
Virtual Tour
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Underground Utilities, Deck, Gutters, Lighting, Underground Sprinkler
  • Waterfront Description: Walk to Water, Beach Rights, Water Community
Interior Features
  • Appliances Included: Oven/Range, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Heated, Partially Finished, Walk-up
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air, Radiant, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Home Automation: Lighting, Security System
  • Interior Features: Security System
  • Laundry Room Info: Main Level
  • Rooms Additional: Foyer, Gym, Laundry Room, Mud Room
  • Rooms Total: 12
Room 1
  • Room Entry Order: 1
  • Room Features: 2 Story Window(s),Cathedral Ceiling,Fireplace
  • Room Level: Main
  • Room Type: Great Room
Room 2
  • Room Entry Order: 10
  • Room Features: Tile Floor
  • Room Level: Lower
  • Room Type: Rec/Play Room
Room 3
  • Room Entry Order: 11
  • Room Features: Full Bath,Hardwood Floor
  • Room Level: Lower
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 12
  • Room Features: Composite Floor
  • Room Level: Lower
  • Room Type: Other
Room 5
  • Listing Key: 33F16FAAF8230E60E0631401100A8804
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Balcony/Deck,Dining Area,Island,Pantry
  • Room Level: Main
  • Room Type: Kitchen
Room 6
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings
  • Room Level: Main
  • Room Type: Dining Room
Room 7
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings,Jack & Jill Bath
  • Room Level: Main
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Jack & Jill Bath
  • Room Level: Main
  • Room Type: Bedroom
Room 9
  • Listing Key: 33F16FAAF8230E60E0631401100A8804
  • Room Entry Order: 6
  • Room Features: 9 ft+ Ceilings,Vaulted Ceiling,Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 10
  • Room Entry Order: 7
  • Room Features: Full Bath,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 11
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Rec/Play Room
Room 12
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Office
Property
Property and Assessments
  • Color: Grey
  • Construction Description: Frame
  • Exclusions: fireplace items, wall mounted tv's, sound system
  • Exterior Siding: Hardie Board, Vertical Siding, Cedar
  • Foundation Type: Concrete
  • Fuel Tank Location: In Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle, Metal
  • Year Built: 2022
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Sq Ft Description: Per Owner
  • Sq Ft Est Heated Below Grade: 1009
  • Living Area SQFT Per Public Records: 4527
Lot Information
  • Lot Description: Fence - Stone, Fence - Full, Dry, Cleared
  • Parcel Number: 415906
  • Sq Ft Est Heated Above Grade: 5018.0
  • Sq Ft Total: 6027.0
  • Zoning: AA
Utilities
  • Heat Fuel Type: Propane
  • Hot Water Description: Tankless Hotwater
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 99 Hillspoint Road

DateEvent & SourcePriceAppreciation
Aug 4, 2025

Closed (Public Record)

Public Record #1909388193

$3,300,000

+5.4% / yr

Jun 15, 2022

Closed (Public Record)

Public Record #1492680256

$2,800,000

+165.2% / yr

Dec 15, 2020

Closed (Public Record)

Public Record #687457361

$650,000

+2.2% / yr

DateEvent & SourcePrice
08/04/2025

Closed (Public Record)

Public Record #1909388193

$3,300,000

+5.4% / yr

06/15/2022

Closed (Public Record)

Public Record #1492680256

$2,800,000

+165.2% / yr

12/15/2020

Closed (Public Record)

Public Record #687457361

$650,000

+2.2% / yr

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

Public Records for 99 Hillspoint Road

Taxable ValueLand$508,700Additions$1,082,100Total$1,590,800
Tax Record2025$30,002 ($2,500 / month)
Home Facts
Beds5Baths5Total Finished SqFt4,527 SqFtAbove Grade Finished SqFt4,527 SqFtUnfinished Basement SqFt312 SqFtStories3Lot Size55,757 SqFtStyleSingle Family ResidenceYear Built2021Year Renovated2021ZoningAACountyWESTERN CONNECTICUTAPNWPRT M:E07 L:060-000

Schools near 99 Hillspoint Road

This home is within Westport School District.
Rating
School
Type
Grades
Distance
Green's Farms School
Public - K to 5
Bedford Middle School
Public - 6 to 8
Staples High School
Public - 9 to 12
Rating
School
Distance
Green's Farms School
PublicK to 5

Bedford 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.

Similar Homes

New listings in 06880

$9,860,000 | 9 Over Rock Lane, Westport, CT 06880
1/17
New

$9,860,000

6
Bedrooms
9,200
Square Feet
2.1
Acres

9 Over Rock Lane, Westport, CT 06880

$1,325,000 | 124 Harvest Cmns, Unit 124, Westport, CT 06880
1/40
New

$1,325,000

2
Bedrooms
2,141
Square Feet

124 Harvest Cmns, Unit 124, Westport, CT 06880

$2,690,000 | 1074 Sturges Highway, Fairfield, CT 06880
1/40
Compass Coming Soon

$2,690,000

4
Bedrooms
4,540
Square Feet
2
Acres

1074 Sturges Highway, Fairfield, CT 06880

$5,495,000 | 3 Stony Point West, Westport, CT 06880
1/39
Listed By Coldwell Banker RealtyOpen: 9/10 12:00PM - 02:00PM

$5,495,000

6
Bedrooms
6,561
Square Feet
1.38
Acres

3 Stony Point West, Westport, CT 06880

$1,649,000 | 104 Old Road, Westport, CT 06880
1/40
Listed By CompassOpen: 9/12 12:00PM - 02:00PM

$1,649,000

4
Bedrooms
2,807
Square Feet
0.51
Acres

104 Old Road, Westport, CT 06880

$675,000 | 12 Strathmore Lane, Unit 12, Westport, CT 06880
1/15

$675,000

2
Bedrooms
1,519
Square Feet

12 Strathmore Lane, Unit 12, Westport, CT 06880

$3,400,000 | 27 Woody Lane, Westport, CT 06880
1/40
Listed By CompassOpen: 9/12 01:00PM - 02:00PM

$3,400,000

5
Bedrooms
6,166
Square Feet
2.55
Acres

27 Woody Lane, Westport, CT 06880

$4,600,000 | 2 Windy Hill Road, Westport, CT 06880
1/39

$4,600,000

6
Bedrooms
8,185
Square Feet
1
Acres

2 Windy Hill Road, Westport, CT 06880

$899,000 | 1 Maplewood Avenue, Westport, CT 06880
1/30

$899,000

2
Bedrooms
1,262
Square Feet
0.25
Acres

1 Maplewood Avenue, Westport, CT 06880

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 99 Hillspoint Road, Westport, CT 06880
$3,300,000
5
6,027
55,756
102 Hillspoint Road, Westport, CT 06880
$647,500
4
2,400
48,787
97 Hillspoint Road, Westport, CT 06880
$1,200,000
3
2,706
45,738
103 Hillspoint Road, Westport, CT 06880
$1,835,000
5
5,546
43,560
100 Hillspoint Road, Westport, CT 06880
$440,000
2
1,690
17,424
104 Hillspoint Road, Westport, CT 06880
$3,950,000
5
9,002
47,480

Explore Nearby Homes

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 The Riverside Realty Group, Susan Lieberman; The Riverside Realty Group, Justine Fink

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.