99 Highfield Rd, Wilton, CT 06897
Property image
Property image
FOR RENT
PET FRIENDLY
FURNISHED

$50,000/mo

Fees may apply
  • 4 Beds
  • 6.5 Baths
  • 4,936 sqft

99 Highfield Rd, Wilton, CT 06897

Silvermine
Cost and fees breakdown
Price may not include required fees and charges.

Home Highlights

Single-Family Home
Attached Garage
Dogs & Cats Allowed
Dishwasher
Forced Air, Central & Central Air
Washer, Dryer

Local Information

  • Map ViewExplore the area around 99 Highfield Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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 creates the ideal backdrop for cozy movie nights. Downstairs, a fully equipped game lounge includes ping pong, Tornado foosball, Dynamo air hockey, darts, and a full-size retro arcade cabinet. For wellness and relaxation, a private fitness area includes a Pilates reformer, Arc Trainer, weight rack, and yoga equipment. Alexa-enabled speakers throughout the home provide seamless sound from room to room, while an in-garage Tesla charger adds convenience for electric vehicle owners. The primary suite is a retreat unto itself, featuring vaulted ceilings, a gas fireplace, and a spa-inspired marble bath with soaking tub and arched window. Three additional guest bedrooms comfortably accommodate up to eight guests in refined comfort. House of Bliss offers something increasingly difficult to find: a true luxury country retreat with a private padel court, resort-style amenities, and space to slow down without sacrificing comfort. House of Bliss - a destination as much as a home.

Details for 99 Highfield Rd

Interior Features

Heating & Cooling
Heating: Central, Forced Air, OilAir ConditioningHeating Fuel: Central
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Summer,Winter,Negotiable,Short Term Lease,Month To MonthCats, small dogs allowed

Exterior Features

Pool
Pool
Parking & Garage
GarageParking: Attached Garage, On Site

Agent Information

Listing Agent
MLS/Source ID: 24181188
Report this Listing

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Costs and Fees

Required monthly rent & fees (based on 12-month lease)
  • Base rent
    $50,000/mo
Required one-time fees
  • Security deposit
    Contact for details
  • Application fee
    Contact for details
  • Administrative fee
    Contact for details
Pricing is subject to change. All calculations are estimates and provided for informational purposes only. Actual amounts may include additional mandatory or optional fees. Please consult the community manager for a complete breakdown of all rental costs.
See more

Rental Market Trends in Silvermine

Last updated Jul 2026
Average rent
$50K
Available listings
1
View rental market trends in Wilton, CT

Around this home

Neighborhood Overview

Silvermine
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Silvermine

At least 1 Trulia users voted on each feature.

  • 100 % Say people would walk alone at night

  • 100 % Say car is needed

  • 100 % Say there's holiday spirit

  • 100 % Say yards are well-kept

  • 100 % Say it's quiet

  • 83 % Say neighbors are friendly

  • 50 % Say it's dog friendly

  • 50 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Local Legal Protections

LGBTQ • Source of Income

Price and Tax history

DateEventPrice
Jun 4, 2026
Source: Smart MLS #24181188
Listed For Rent
$50,000
Nov 1, 2024
Source: Smart MLS #24030762
Sold
$2,200,000
Jul 16, 2024
Source: Smart MLS #24030762
Listed For Sale
$2,349,000
Apr 22, 2016
Source: Smart MLS #99128154
Sold
$1,737,500
Mar 2, 2016
Source: Agent Provided
Pending
$1,839,000
Klemm Real Estate Inc
Joseph Lorino

Frequently asked questions about 99 Highfield Rd

  • What is the pet policy at 99 Highfield Rd?
    99 Highfield Rd in Wilton, CT allows cats and small dogs.
  • How does the rent for 99 Highfield Rd compare to similar 4+ bedroom houses in Silvermine?
    99 Highfield Rd in Wilton, CT rents about 667% above the area average for 4+ bedroom houses in Silvermine ($6,522/mo).
  • What are the closest schools to 99 Highfield Rd?
    The closest schools to 99 Highfield Rd in Wilton, CT are Cider Mill School (Elementary, rated 9/10), Middlebrook School (Middle, rated 10/10), Miller-Driscoll School (Pre-K/Elementary).
  • Does 99 Highfield Rd have a pool?
    Yes, 99 Highfield Rd in Wilton, CT has a pool.
  • Does 99 Highfield Rd have laundry facilities?
    Yes, 99 Highfield Rd in Wilton, CT has in-unit laundry.
  • Does 99 Highfield Rd have a garage?
    Yes, 99 Highfield Rd in Wilton, CT has an attached garage.

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
$1,800,000 PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.

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99 Highfield Rd, Wilton, CT is a 4 bedroom, 7 bathroom, 4,936 sqft single-family home built in 1995. 99 Highfield Rd is located in Silvermine, Wilton. 99 Highfield Rd was listed for rent for $50,000/month on Jun 4, 2026. This property is pet friendly.