99 Highfield Rd

$50,000
Price
4,936 Sq. Ft.
$122 / Sq. Ft.
4,936
Sq. Ft.
$122
per Sq. Ft.

Description

House of Bliss~A rare Connecticut estate where luxury living meets the world's fastest-growing racquet sport. Set on two private acres, House of Bliss is a four-bedroom, five-and-a-half-bath retreat designed for extended stays, executive relocations, family escapes, and padel enthusiasts alike. Its defining feature is something almost never found at a private residence: a regulation 10m x 20m glass-walled padel court, custom-built in 2024 with premium artificial turf, tempered glass walls, and shaded...House of Bliss~A rare Connecticut estate where luxury living meets the world's fastest-growing racquet sport. Set on two private acres, House of Bliss is a four-bedroom, five-and-a-half-bath retreat designed for extended stays, executive relocations, family escapes, and padel enthusiasts alike. Its defining feature is something almost never found at a private residence: a regulation 10m x 20m glass-walled padel court, custom-built in 2024 with premium artificial turf, tempered glass walls, and shaded Adirondack seating overlooking the surrounding lawn. Beyond the court, every detail has been curated for effortless living. A heated saltwater pool anchors the outdoor experience, accompanied by a newly designed patio, expansive deck, gas grill, teak dining table, and low-smoke fire pit. The manicured grounds offer ample space for bocce, spike ball, or simply enjoying the quiet beauty of the Connecticut countryside. Inside, the home centers around a spectacular chef's kitchen featuring a grand marble island, professional-grade appliances, and walls of windows that fill the space with natural light. The kitchen flows seamlessly into a soaring great room with vaulted beamed ceilings and a dramatic stone fireplace-the perfect setting for long breakfasts, memorable dinners, and evenings spent together. Entertainment is woven throughout the home. A dedicated billiards room features a premium pool table, wet bar, stone fireplace, and quiet study area. Upstairs, a vaulted media loung

Property Details for 99 Highfield Road

Basement Description
Full
Direct Waterfront
No
Garages Number
3
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 06/05/2026 02:21 AM

Property Details for 99 Highfield Road

StatusActive
MLS #24181188
Days on Market3
Pet PolicyAllowed
Rental Incentives-
Costs & Fees-
Available Date06/23/2026
Lease Term-
Furnished-
Property TypeRental
MLS TypeResidential Rental / Single Family Rental
Year Built1995
Lot Size2.04 AC / 88,862 SF
CountyFairfield County

Location

Listing Courtesy of Klemm Real Estate Inc, Joseph Lorino
Add your commute

Building Information for 99 Highfield Road

Building/Complex99 Highfield RdFloor-Stories-Pet PolicyAllowedPet Policy DetailsYesYear Built1995Building Size-Lot Size2.04 AC / 88,862 SF

Property Information for 99 Highfield Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: gps
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.167704
  • Longitude: -73.440517
  • Pets Allowed Info: ask
  • Pets Allowed: Yes
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
Interior and Exterior Features
Exterior Features
  • Pool Description: Fiberglass, Heated, Salt Water, In Ground Pool
  • Waterfront Description: Beach Rights, Access
Interior Features
  • Appliances Included: Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Finished, Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Rooms Total: 12
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Upper
  • Room Type: Bedroom
Room 5
  • Listing Key: 5370CE04E9EEDA15E063E201100A6EA0
  • Room Entry Order: 5
  • Room Level: Upper
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Smoking Allowed: No
  • Year Built: 1995
  • Year Built Source: Public Records
  • Living Area SQFT Per Public Records: 4936
Lot Information
  • Lot Description: Professionally Landscaped, Open Lot
  • Parcel Number: 1927927
  • Sq Ft Est Heated Above Grade: 4936.0
  • Sq Ft Total: 4936.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner
Rental
Rental
  • Rental Duration: Summer Furnished, Winter Furnished, Flexible Terms Furnished, Short Term Furnished

Schools near 99 Highfield Road

This home is within Wilton School District.
Rating
School
Type
Grades
Distance
Public - PK to 2
Public - 3 to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Miller-Driscoll School
PublicPK to 2

Cider Mill School
Public3 to 5

Middlebrook School
Public6 to 8

Wilton 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.

99 Highfield Road is available for rent in Wilton, CT 06897. This property was listed on June 5, 2026 by Klemm Real Estate Inc, it's currently listed at $50,000. This listing's school district is Wilton School District. Nearby schools include Miller-Driscoll School, Cider Mill School and Middlebrook School. 99 Highfield Road is a 4-bed, 7-bath, 4,936 sqft a property built in 1995.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the owner. 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 Klemm Real Estate Inc, Joseph Lorino

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.