Date
Details
Price
Change
Source
6/11/2026
Listed
$799,999
—
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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- Open House: 12:00 PM - 2:00 PM
Sunday 6/14 12:00 PM - 2:00 PM
99 Cheryl Ann Drive,Milford, CT 0646099 Cheryl Ann DriveMilfordCT06460
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Property Description
Welcome home to this beautifully updated Colonial, tucked on a picturesque tree-lined street and set on a private, level 1.38-acre lot with exceptional landscaping and curb appeal. Blending open-concept living with warm, inviting spaces, this 4-bedroom, 2.5-bath home is designed for both everyday comfort and effortless entertaining. Refinished hardwood floors flow throughout the home, complemented by updated kitchens and baths. The main level offers three separate living areas, including a spacious living room, cozy family room with fireplace and built-ins, and a bright sunroom. The renovated eat-in kitchen features quartz countertops, gray cabinetry, newer appliances, and a charming brick backsplash with open shelving. A slider leads to the backyard oasis complete with a patio, pergola, fire pit, and playscape. Upstairs, the primary suite features a walk-in closet and updated bath with dual vanity. Three additional generously sized bedrooms, a full bath, and ample hallway storage complete the second floor. The unfinished lower level offers excellent storage and endless potential for future finished living space. Recent improvements include a newer driveway, fresh interior paint, power washing, yard enhancements, a 10-year-old roof, and a 6-year-old hot water heater. Conveniently located near the Post Road, YMCA, Eisenhower Park, Orchards Golf Course, shopping, dining, and Milford's beautiful coastline, including Silver Sands State Park and MANY public beaches!
Full Property Details
Full Property Details for 99 Cheryl Ann Dr
General
- Price: $799,999
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24181787
- Updated: 6/11/2026
- Added to Site: 5 day(s) ago
Interior
- Number of Rooms: 8
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- 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
- Family Room: Family Room, Main
- Kitchen: Kitchen, Main
- Dining Room: Dining Room, Main
- Laundry: Main Level
Exterior
- Exterior Features: Shed, Gutters, Lighting, Patio
- Color: Gray
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Total Spaces: 8
- Parking: Attached Garage, Paved, Driveway
Location
- County: New Haven
- Driving Directions: Cheryl Ann Drive
School Information
- Elementary School: Orange Avenue
- Middle School: Harborside
- High School: Joseph A. Foran
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Natural Gas
- Heating Fuel: Natural Gas
- Water Heater: Upright Tank
Utilities
- Sewer: Public Sewer Connected
- Water: Public Water Connected
Structural Information
- Architectural Style: Colonial
- Construction Status: No/Resale
- Exterior Const.: Vinyl Siding
- Basement Desc.: Full, Unfinished
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 2,212
- Above Ground: 2,212 Sq. Ft.
- Year Built: 1964
Lot Features
- Lot Size (Acres): 1.38
- Driveway/Sidewalk: Private, Paved
- Zoning: RA
- Lot Description: Lightly Wooded, Level Lot, Cleared
Water Features
- Water Front Desc.: Beach Rights
Financial Considerations
- Assessment Amount: $325,850
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 1218639
Listed by Compass Connecticut, LLC, Forte Team At Compass, Andrea Viscuso
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Listing agent
— 99 Cheryl Ann Dr —
Andrea Viscuso
Compass Connecticut, LLC
Agent Contact: (203) 627-7767 Office Contact: (203) 489-6499
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 99 Cheryl Ann Dr
School District:Milford School District
| Name | Grades | Distance |
|---|---|---|
Orange Avenue School 260 Orange Ave., Milford, CT 06460 | PK-2 | 1.1 mi |
Calf Pen Meadow School 395 Welchs Point Road, Milford, CT 06460 | 3-5 | 2.8 mi |
Harborside Middle School 175 High Street, Milford, CT 06460 | 6-8 | 2.2 mi |
Joseph A. Foran High School 80 Foran Road, Milford, CT 06460 | 9-12 | 2.7 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 99 Cheryl Ann Dr
Estimate the Cost
Estimate the Cost for 99 Cheryl Ann Dr
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- Single Family
- Active
- Updated 4 days ago
- 3Beds
- 2Total Baths
- 1,613Sq. Ft.
- Single Family
- Active
- Updated 12 days ago
- 4Beds
- 3Total Baths
- 3,085Sq. Ft.
- Single Family
- Active
- Updated 22 hours ago
- 4Beds
- 2Total Baths
- 1,834Sq. Ft.
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- Single Family
- Active
- Updated 13 hours ago
- 3Beds
- 2Total Baths
- 1,106Sq. Ft.
Listed by Wayne Hugendubel (203) 795-2427
- Single Family
- Active
- Updated 13 hours ago
- 3Beds
- 2Total Baths
- 2,042Sq. Ft.
- Single Family
- Active
- Updated 13 hours ago
- 4Beds
- 3Total Baths
- 3,518Sq. Ft.
- Condo
- Active
- Updated 7 hours ago
- 1Bed
- 3Total Baths
- 1,426Sq. Ft.
Listed by The Lewis Team at Coldwell Banker Realty (203) 610-9670
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- Single Family
- Active
- Updated 3 days ago
- 6Beds
- 4Total Baths
- 4,514Sq. Ft.
Listed by Marilyn Heffers (203) 984-1068
- Single Family
- Active
- Updated 5 days ago
- 2Beds
- 1Total Bath
- 1,046Sq. Ft.
Listed by Gerard Sullivan (860) 967-4607
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 1Total Bath
- 1,257Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 3Total Baths
- 2,759Sq. Ft.
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- Single Family
- Closed
- 4Beds
- 3Total Baths
- 2,992Sq. Ft.
Listed and Sold by Nick Mastrangelo
- Single Family
- Closed
- 4Beds
- 3Total Baths
- 2,739Sq. Ft.
Listed by Victoria Stillings
Sold by William Raveis Real Estate
Sold by William Raveis Real Estate
- Single Family
- Closed
- Updated 12 days ago
- 3Beds
- 2Total Baths
- 1,719Sq. Ft.
99 Cheryl Ann Drive, Milford, CT 06460 (MLS# 24181787) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 99 Cheryl Ann Drive is currently listed for $799,999 and was received on June 07, 2026. Want to learn more about 99 Cheryl Ann Drive? Do you have questions about finding other Single Family real estate for sale in Milford? You can browse all Milford real estate or contact a Coldwell Banker agent to request more information.