Date
Details
Price
Change
Source
6/04/2026
Listed
$50,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$50,000
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Property 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
Full Property Details
Full Property Details for 99 Highfield Rd
General
- Rent: $50,000
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24181188
- Updated: 6/5/2026
- Added to Site: 65 day(s) ago
Rental Information
- Rental Type: Summer Furnished, Winter Furnished, Flexible Terms F
- Lease Terms: Per Month
- Short Term: Yes
Interior
- Number of Rooms: 12
- Fireplace: Yes
- Number of Fireplaces: 3
- Appliances: Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
Rooms
Bathrooms
- Total Bathrooms: 7
- Full Bathrooms: 6
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Primary Bedroom, Upper
- Bedroom 1: Bedroom, Upper
- Bedroom 2: Bedroom, Upper
- Bedroom 3: Bedroom, Upper
Other Rooms
- Living Room: Living Room, Main
- Dining Room: Dining Room, Main
Additional Information
- Pool: Yes
- Pool Description: Fiberglass, Heated, Salt Water, In Ground Pool
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Parking: Attached Garage
Location
- County: Fairfield
- Driving Directions: gps
School Information
- Elementary School: Per Board of Ed
- High School: Per Board of Ed
Community
- Pets Allowed: Yes
- Pet Restrictions: ask
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Domestic
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Colonial
- Construction Status: No/Resale
- Basement Desc.: Full
- Attic: Yes
- Square Feet: 4,936
- Above Ground: 4,936 Sq. Ft.
- Year Built: 1995
Lot Features
- Lot Size (Acres): 2.04
- Zoning: R-2
- Lot Description: Professionally Landscaped, Open Lot
Water Features
- Water Front Desc.: Beach Rights, Access
Financial Considerations
- Tenant Pays: All Utilities, Grounds Maintenance
Disclosures and Reports
- Property ID: 1927927
Listed by Klemm Real Estate Inc, Joseph Lorino
Schools
Schools serving 99 Highfield Rd
School District:Wilton School District
| Name | Grades | Distance |
|---|---|---|
Miller-Driscoll School 217 Wolfpit Road, Wilton, CT 06897 | PK-2 | 0.6 mi |
Cider Mill School 240 School Road, Wilton, CT 06897 | 3-5 | 2.5 mi |
Middlebrook School, Wilton, CT 131 School Road, Wilton, CT 06897 | 6-8 | 2.4 mi |
Wilton High School 395 Danbury Road, Wilton, CT 06897 | 9-12 | 3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 99 Highfield Rd
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- Single Family
- Active
- Updated 18 hours ago
- 2Beds
- 2Total Baths
- 1,464Sq. Ft.
- Apartment
- Active
- Updated 2 days ago
- 2Beds
- 1Total Bath
- 850Sq. Ft.
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- Single Family
- Active
- Updated 4 days ago
- 2Beds
- 1Total Bath
- 1,000Sq. Ft.
- Single Family
- Active
- Updated 5 days ago
- 4Beds
- 3Total Baths
- 2,516Sq. Ft.
Listed by Mary Valenton (203) 957-1108
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- Single Family
- Closed
- 5Beds
- 7Total Baths
- 7,808Sq. Ft.
Listed by Linda Skolnick
Sold by Emily Gordon
Sold by Emily Gordon
- Single Family
- Closed
- 4Beds
- 6Total Baths
- 3,627Sq. Ft.
Listed by William Raveis Real Estate
Sold by Tanya Sprague
Sold by Tanya Sprague
- Single Family
- Closed
- 4Beds
- 4Total Baths
- 1,692Sq. Ft.
Listed by Robin Singer
Sold by Higgins Group Bedford Square
Sold by Higgins Group Bedford Square
99 Highfield Road, Wilton, CT 06897 (MLS# 24181188) is a Single Family property with 4 bedrooms, 6 full bathrooms and 1 partial bathroom. 99 Highfield Road is currently listed for rent at $50,000 and was received on June 04, 2026. Want to learn more about 99 Highfield Road? Do you have questions about finding other real estate for sale or rent in Wilton? You can browse all Wilton rentals or contact a Coldwell Banker agent to request more information.