99 Highfield Rd
Wilton, CT 06897
Silvermine
4 Beds
6.5 Baths
4,936 sqft
Price may not include required fees and charges.
$50,000/mo
Fees may apply
$50,000/mo
Fees may apply
Price may not include required fees and charges.
- 4 Beds
- 6.5 Baths
- 4,936 sqft
Local Information
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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 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.
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.
Home Highlights
Pets
Dogs & Cats
Parking
Attached Garage
Outdoor
Pool
A/C
Heating & Cooling
Utilities
Contact Manager
Listed
6 days ago
Details for 99 Highfield Rd
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Heating & Cooling Heating: Oil, Forced Air, FireplaceAir ConditioningHeating Fuel: Oil |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
Room & Shared Space Shared space is furnished |
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Days on Market: 6 days on Trulia |
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Year Built Year Built: 1995 |
Property Type / Style Property Type: Single Family Home |
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Lease Term: Summer,Winter,Negotiable,Short Term Lease,Month To MonthCats, small dogs allowed |
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Pool Pool |
Parking & Garage Parking: Attached Covered, On Site |
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Listing Agent MLS/Source ID: 24181188 |
Price History for 99 Highfield Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 06/04/2026 | $50,000 | Listed For Rent | Smart MLS #24181188 |
| 11/01/2024 | $2,200,000 | Sold | Smart MLS #24030762 |
| 07/16/2024 | $2,349,000 | Listed For Sale | Smart MLS #24030762 |
| 04/22/2016 | $1,737,500 | Sold | Smart MLS #99128154 |
| 03/02/2016 | $1,839,000 | Pending | Agent Provided |
| 02/04/2016 | $1,839,000 | PriceChange | Agent Provided |
| 10/23/2015 | $1,879,000 | Listed For Sale | Agent Provided |
| 06/01/2012 | $1,300,000 | Sold | N/A |
| 12/05/1995 | $785,000 | Sold | N/A |
| 08/28/1995 | $261,800 | Sold | N/A |
| 06/13/1995 | $300,000 | Sold | N/A |
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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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Assigned Schools
These are the assigned schools for 99 Highfield Rd.
- Cider Mill School
- 3-5
- Public
- 770 Students
9/10GreatSchools RatingParent Rating AverageGreat experience with 2 kids so farParent Review7y ago - Middlebrook School
- 6-8
- Public
- 894 Students
10/10GreatSchools RatingParent Rating AverageThe leadership and teachers at Middlebrook are the best I've known. This is so important for this age group. They really handle the challenges of middle school years so well. My children are very different from each other and they helped both of my children find their place and succeed academically. They had great middle school friends and and some of their favorite teachers. Not many can say that about middle school!Parent Review4y ago - Miller-Driscoll School
- PK-2
- Public
- 842 Students
NAGreatSchools RatingParent Rating AverageMy family has had terrible experiences with this school. The teachers cannot be bothered to communicate with parents or care about the kids enrolled. The curriculum is boring and does nothing to challenge the many bright kids at the school. The administrators care even less about the kids than the teachers do. They use screens to babysit the kids a lot. The only bright spot is the pretty building which does not make up for everything else. I actually don’t understand how this is a good school district.Parent Review4mo ago - Wilton High School
- 9-12
- Public
- 1231 Students
10/10GreatSchools RatingParent Rating AverageWe had an amazing experience with the Wilton school system. The AP classes offered helped us to get read for college and the teachers are incredibly helpful and kind. They educate the whole child, and care about the students. In today’s world, this is rare but the educators here are amazing educators and kind people. We moved to Wilton for the school system and it was a great decision.Parent Review1y ago 
Check out schools near 99 Highfield Rd.
Neighborhood Overview
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
Local Legal Protections
LGBTQ • Source of Income
Klemm Real Estate Inc
Joseph Lorino
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.