Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,975,000 Coming Soon

  • For Sale
  • Coming Soon
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,932 Sq. Ft.
  • 2 Car Garage
  • Updated 10 hours ago
See This Home
Save This Home
See This Home
Save This Home
The best water views in Milford! Designed by award-winning, Yale-trained architect Ray Oliver, this custom coastal home offers 5 bedrooms, sweeping water views from almost every room, abundant natural light and the beauty and tranquility of this special, private setting. Upon arrival, you are welcomed by mature, low-maintenance perennial gardens and the soothing sounds of the fountain. A dramatic wall of windows frames the Long Island Sound from the main living area, while French doors open to an expansive waterfront deck-perfect for dining, entertaining or watching the boats, changing tides, sunrises and sunsets. High ceilings, a beautiful stained-glass window and three marble baths add architectural character. The thoughtfully designed layout offers multiple gathering spaces and features abundant closets and storage, a walk-in pantry and beautifully updated chef's kitchen. A serene second floor book nook and primary bedroom suite with 6-foot Jacuzzi tub and stunning views, offer peaceful retreats. 2 additional bedrooms, a full bath and laundry complete the second floor. The third floor offers 2 more bedrooms with walk-in closets plus a full bath. Launch a kayak, watch the sailboats or enjoy coastal birdlife from a wonderfully private vantage point. 2-car garage plus 4 driveway spaces! Set on a quiet one-way street with sidewalks, a nearby playground and restaurants within walking distance, this exceptional waterfront home offers privacy and a special coastal lifestyle.

Full Property Details for 109 Hillside Ave

General

  • Price: $1,975,000
  • Taxes: (July 2025-June 2026)
  • Status: Coming Soon
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24201489
  • Updated: 8/25/2026
  • Expected Market Date: 8/28/2026

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Foyer, Laundry Room
  • Interior Features: Auto Garage Door Opener, Open Floor Plan, Security System
  • Appliances: Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Primary Bathroom: Primary Bath - Doubl, 11 x 9, Upper
  • Full Bath: Built-Ins, Full Bath, Tub w/Shower, Tile Floor, 10 x 8, Upper
  • Partial Bath: Tile Floor, 7 x 6, Main

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Balcony/Deck, Bedroom Suite, Ceiling Fan, Full Bath, Walk-In Closet, Hardwood Floor, 18 x 14, Upper
  • Bedroom 1: Bedroom - Ceiling Fan, Hardwood Floor, 14 x 10, Upper
  • Bedroom 2: Bedroom - Ceiling Fan, Hardwood Floor, 14 x 13, Upper
  • Bedroom 3: Bedroom - Ceiling Fan, Walk-In Closet, Wall/Wall Carpet, On 3rd Floor, 16 x 11, Upper
  • Bedroom 4: Bedroom - Ceiling Fan, Walk-In Closet, Wall/Wall Carpet, On 3rd Floor, 16 x 13, Upper

Other Rooms

  • Living Room: Living Room - Bay/Bow Window, 9 ft+ Ceilings, Hardwood Floor, 16 x 10, Main
  • Family Room: Family Room - 9 ft+ Ceilings, Ceiling Fan, French Doors, Hardwood Floor, 18 x 15, Main
  • Eat In Kitchen: Eat-In Kitchen - 9 ft+ Ceilings, Balcony/Deck, Granite Counters, Dry Bar, Eatin, 18 x 10, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Balcony/Deck, Ceiling Fan, French Doors, Hardwood Floor, 15 x 11, Main
  • Laundry: Upper Level
  • Other Room 1: Other - Concrete Floor, 28 x 14, Lower
  • Other Room 2: Other - Pantry, 10 x 5, Main
  • Other Room 3: Other - Walk-In Closet, Hardwood Floor, 11 x 6, Upper
  • Other Room 4: Other - Book Shelves, Built-Ins, Hardwood Floor, 8 x 7, Upper
  • Other Room 5: Other - Laundry Hookup, Tile Floor, 9 x 7, Upper

Exterior

  • Exterior Features: Balcony, Sidewalk, Garden Area, Lighting, Patio
  • Color: Grey

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking: Under House Garage, Off Street Parking, Driveway

Location

  • County: New Haven
  • Neighborhood: Woodmont
  • Driving Directions: Yale Ave to Edgefield to Hillside

School Information

  • Elementary School: J. F. Kennedy
  • Middle School: East Shore
  • High School: Joseph A. Foran

Community

  • Community Name: Woodmont

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Air, Zoned, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, Upright Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Contemporary
  • Construction Status: No/Resale
  • Exterior Const.: Cedar
  • Basement Desc.: None
  • Roof: Asphalt Shingle
  • Square Feet: 2,932
  • Above Ground: 2,932 Sq. Ft.
  • Year Built: 2000

Lot Features

  • Lot Size (Acres): 0.11
  • Driveway/Sidewalk: Private
  • Zoning: R5
  • Lot Description: Level Lot, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: L. I. Sound Frontage, Water Community, View, Access

Financial Considerations

  • Annual Sewer Fee: $364
  • Assessment Amount: $729,620
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Flood Zone: Yes
  • Property ID: 1209557
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Meet the listing agent

Meet the listing agent
— 109 Hillside Ave —

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 109 Hillside Ave

School District:Milford School District
NameGradesDistance
Orchard Hills School
185 Marino Drive, Milford, CT 06460
3-50.9 mi
Live Oaks School
575 Merwin Avenue, Milford, CT 06460
K-21.4 mi
East Shore Middle School
240 Chapel Street, Milford, CT 06460
6-80.6 mi
Joseph A. Foran High School
80 Foran Road, Milford, CT 06460
9-120.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Tax History for 109 Hillside Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$21,560
1%
$729,620
—
2023
$21,261
7%
$729,620
—
2023
$19,824
2%
$729,620
—
2022
$19,444
11%
$729,620
15%
2021
$17,497
—
$632,810
—
2020
$17,516
-4%
$632,810
—
2019
$18,162
3%
$632,810
—
2018
$17,554
—
$632,810
—
2017
$17,586
8%
$632,810
8%
2016
$16,264
—
$584,210
—
2015
$16,288
2%
$584,210
—
2014
$15,902
-14%
$584,210
-17%
2011
$18,585
—
$707,180
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 109 Hillside Ave

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Similar Properties near 109 Hillside Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

41 Deerfield Ave, Milford, CT 06460 - Photo 1
$1,895,000

41 Deerfield Ave  Milford, CT 06460

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 2,388
    Sq. Ft.
Listed by Houlihan Lawrence WD
500 River Rd, Stratford, CT 06614 - Photo 1 Just Listed
$1,925,000

500 River Rd  Stratford, CT 06614

  • Single Family
  • Active
  • Updated 5 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 5,030
    Sq. Ft.
Listed by William Raveis Real Estate
445 Orange St, New Haven, CT 06511 - Photo 1
$1,999,000

445 Orange St  New Haven, CT 06511

  • Single Family
  • Active
  • 4
    Beds
  • 5
    Total Baths
  • 4,016
    Sq. Ft.
Listed by Pearce Real Estate
110 Porters Hill Rd, Trumbull, CT 06611 - Photo 1 Just Listed
$1,749,000

110 Porters Hill Rd  Trumbull, CT 06611

  • Single Family
  • Active
  • Updated 3 hours ago
  • 4
    Beds
  • 6
    Total Baths
  • 5,170
    Sq. Ft.
Listed by William Raveis Real Estate

Just Listed near 109 Hillside Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

888 Racebrook Rd, Orange, CT 06477 - Photo 1 Just Listed
$519,000
Open House

888 Racebrook Rd  Orange, CT 06477

  • Single Family
  • Active
  • Updated 16 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,358
    Sq. Ft.
Listed by Ellison Homes Real Estate
634 Aspen Ln, Orange, CT 06477 - Photo 1 Just Listed
$675,000

634 Aspen Ln  Orange, CT 06477

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,410
    Sq. Ft.
Listed by William Raveis Real Estate
138 Bison Ln, Stratford, CT 06614 - Photo 1 Just Listed
$480,000

138 Bison Ln  #B  Stratford, CT 06614

  • Single Family
  • Active
  • Updated 16 hours ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,938
    Sq. Ft.
Listed by The Lewis Team at Coldwell Banker Realty (203) 610-9670
81 Peck St, Stratford, CT 06614 - Photo 1 Just Listed
$450,000

81 Peck St  Stratford, CT 06614

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,163
    Sq. Ft.
Listed by Lauren Freedman (203) 889-8336

Price Reduced near 109 Hillside Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

80 Prayer Spring Rd, Stratford, CT 06614 - Photo 1 Price Reduced
-$15,000 (-2.01%)
$730,000

80 Prayer Spring Rd  Stratford, CT 06614

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,115
    Sq. Ft.
Listed by Gigi Fryer (203) 508-2550
95 Wildwood Dr, Stratford, CT 06615 - Photo 1 Price Reduced
-$65,000 (-7.88%)
$760,000

95 Wildwood Dr  Stratford, CT 06615

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,788
    Sq. Ft.
Listed by Matthew Boateng (203) 632-9755
1451 N Peters Ln, Stratford, CT 06614 - Photo 1 Price Reduced
-$43,000 (-4.41%)
$932,000

1451 N Peters Ln  Stratford, CT 06614

  • Single Family
  • Active
  • Updated 6 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 3,271
    Sq. Ft.
Listed by YellowBrick Real Estate LLC
15 Tavern Rock Rd, Stratford, CT 06614 - Photo 1 Price Reduced
-$8,000 (-1.19%)
$664,900

15 Tavern Rock Rd  Stratford, CT 06614

  • Single Family
  • Active
  • Updated 23 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,454
    Sq. Ft.
Listed by Silver and Oak Realty

Recent Sales near 109 Hillside Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2 Rock Rd, Milford, CT 06460 - Photo 1 Sold
$2,095,000

2 Rock Rd  Milford, CT 06460

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,688
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Raveis Real Estate
57 Pelham St, Milford, CT 06460 - Photo 1 Sold
$2,200,000

57 Pelham St  Milford, CT 06460

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,718
    Sq. Ft.
Listed by Stacy Blake Realty LLC
Sold by William Pitt Sotheby's Int'l
77 Carrington Ave, Milford, CT 06460 - Photo 1 Sold
$2,200,000

77 Carrington Ave  Milford, CT 06460

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,375
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by Holli Shanbrom and Rebecca Lavi
139 Rogers Ave, Milford, CT 06460 - Photo 1 Sold
$1,720,000

139 Rogers Ave  Milford, CT 06460

  • Single Family
  • Closed
  • Updated 7 hours ago
  • 4
    Beds
  • 6
    Total Baths
  • 6,572
    Sq. Ft.
Listed by Higgins Group Real Estate
Sold by West Shore Realty

109 Hillside Avenue, Milford, CT 06460 (MLS# 24201489) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 109 Hillside Avenue is currently listed for $1,975,000 and was received on August 25, 2026. This property is listed by Fowler Sakey Team at Coldwell Banker Realty from our Fairfield Office.Want to learn more about 109 Hillside Avenue? 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.

Tour this property