535 Highfield Dr, Orange, CT 06477
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Property image
OFF MARKET

535 Highfield Dr
Orange, CT 06477

  • 6 Beds
  • 4 Baths
  • 6,774 sqft (on 1.10 acres)

$968,700

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $6,800/mo*
Refinance Your Home

$968,700

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $6,800/mo*
Refinance Your Home
6 Beds
4 Baths
6,774 sqft
(on 1.10 acres)

Local Information

  • Map ViewExplore the area around 535 Highfield Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1977
Lot Size
1.1 acres
Living Area
6,774 sqft
Price/Sqft
$143
Parking
Garage

About this House

Custom designed contemporary with almost 7,000 sq ft of high end living space! Based on a new septic design this home boasts 6 bedrooms! Totally updated it has an over sized chef's kitchen complete with granite, stainless appliances, cabinets galore and an eat in kitchen for large family dinners ~ There are 5 bedrooms, (3 with walk in closets) and 3 updated full baths on the main floor and 1 bedroom on the second floor ~ The master suite overlooks the yard and is complete with a 2 person sunken in spa like jacuzzi, over sized lime stone shower and a deck! The lower level opens to a huge walk out party room and onto a level, manicured yard with grounds including a koi pond, circular drive, 3 car garage, underground utilities and all set on a quiet cul de sac. A lower level in law apartment featuring a kitchenette, family room, bedroom, full bath, lots of closet space and sliders providing an abundance of natural light ~ Located minutes to Rte 1 and all major highways ~ Enjoy endless hot water with the 100 gallon hydro air super store tank ~ City water ~ Central air ~ Burglar/ fire alarm system and a new roof! This 14 room home is one of a kind!
535 Highfield Dr, Orange, CT 06477 is a 6 bedroom, 4 bathroom, 6,774 sqft multi-family built in 1977. It last sold for $750,000 on Oct 18, 2022. More recently, it was listed as a rental in December 2018 with an asking price of $3,400 per month. That rental listing was removed on January 4, 2019. It is currently off market. The Trulia Estimate is $968,700, with a rent estimate of $3,047/month.

Home Details for 535 Highfield Dr

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 17Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Office, Recreation Room, Workshop, Sun Room
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Stone, WoodLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 9Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1977Year Updated: 2014
Property Type / Style
Property Type: Multi FamilyArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 1.10 acres

Mobile R/V

RV Parking
Rv Parking

Additional Information

Intercom

Price History for 535 Highfield Dr

DatePriceEventSource
10/18/2022$750,000Sold
Smart MLS #170518976
08/30/2022$769,900ContingentSmart MLS #170518976
08/24/2022$769,900Listed For SaleSmart MLS #170518976
12/03/2019$549,900ListingRemovedAgent Provided
11/02/2019$549,900PendingAgent Provided
08/08/2019$549,900PriceChange
Agent Provided
05/29/2019$575,000Listed For SaleAgent Provided
01/04/2019$3,400ListingRemovedN/A
12/28/2018$579,000ListingRemovedAgent Provided
12/13/2018$3,400Listed For RentN/A
12/06/2018$579,000PriceChange
Agent Provided
10/23/2018$599,000PriceChange
Agent Provided
10/09/2018$630,000PriceChange
Agent Provided
08/21/2018$670,000PriceChange
Agent Provided
07/13/2018$690,000Listed For SaleAgent Provided
06/29/1989$290,000Sold
N/A

Market trends in Orange

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
5MoM
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Property Tax and Assessment

Year2025
Tax$15,074
Assessment$518,000
Home facts updated by county records

Comparable Sales for 535 Highfield Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
57 Dalton Street, West Haven, CT
1.06
Multi-Family Home
$470,000
03/03/26
6
2
2,100
42 Canton Street, West Haven, CT
1.06
Multi-Family Home
$450,000
09/18/25
5
2
2,016
26 Ashford Street, West Haven, CT
1.21
Multi-Family Home
$420,000
09/12/25
5
2
1,728
26-30 Ashford Street, West Haven, CT
1.21
Multi-Family Home
$420,000
09/12/25
5
2
1,728
3 Vernon Street, West Haven, CT
1.46
Multi-Family Home
$500,000
04/21/26
6
3
2,457
21 Dix St, West Haven, CT
1.18
Multi-Family Home
$187,500
01/15/26
5
2
1,956
36 Norfolk Street, West Haven, CT
1.26
Multi-Family Home
$460,000
05/11/26
4
2
1,498
699 Forest Road, West Haven, CT
2.10
Multi-Family Home
$660,000
02/02/26
8
5
3,411
61 Hillside Street, West Haven, CT
1.78
Multi-Family Home
$470,000
06/24/26
5
2.5
2,396
16 Hillside Street, West Haven, CT
1.85
Multi-Family Home
$300,000
07/31/25
4
2
2,327

Nearby homes

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Assigned Schools

These are the assigned schools for 535 Highfield Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Orange

At least 111 Trulia users voted on each feature.

  • 88 % Say parking is easy

  • 81 % Say yards are well-kept

  • 79 % Say car is needed

  • 77 % Say it's dog friendly

  • 71 % Say kids play outside

  • 71 % Say it's quiet

  • 71 % Say there's holiday spirit

  • 67 % Say there's wildlife

  • 64 % Say they plan to stay for at least 5 years

  • 58 % Say people would walk alone at night

  • 49 % Say neighbors are friendly

  • 40 % Say streets are well-lit

  • 35 % Say it's walkable to restaurants

  • 31 % Say there are community events

  • 29 % Say there are sidewalks

  • 26 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Ahanafy1979
    "I commute long distances to my work almost every day to Norwalk; there is no public transportation that can easily get me to my work on time."
    0
    Flag
  • Patty Gambardella
    "Carnival in the summer, lots of community spirit. Local sports are well supported and well attended. "
    0
    Flag
  • Pat G.
    "I work from home, no commuting needed, but I am on a public bus line and live very close to major highways, so commuting is not a problem."
    0
    Flag
  • Dhruvesh
    "great schools,nice neighborhood, quite, convenient to high ways, grocery stores and restaurants. nice trails and parks, community facilities such as pool, Gym"
    0
    Flag
  • Pat G.
    "Pets are allowed, but there is a limited area for walking or exercising dogs. I see many of my neighbors bringing their dogs to other locations to walk them and give them exercise. "
    0
    Flag
  • Pat G.
    "Great school system with high expectations and high achievement for its students. Excellent opportunity for community involvement. "
    2
    Flag
  • Estheraggrey26
    "It’s quiet is beautiful it’s peaceful School is very great I feel safe with children a safe and I’m happy it’s just that the taxes is so high but other than that I love my community I love the school I love my neighbors"
    0
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  • Trulia User
    "A great town to raise a family. We have a convenient and safe community center with ball fields, town pool, and family events. We also have the convenience of route 1 shopping with the privacy and more rural residential neighborhoods. Award winning school system."
    0
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  • Kvarekova
    "I see people walking, jogging, walking with strollers or dogs all the time. I do it myself all the time too. Take the kids for scooter or bike ride. It is very nice, friendly neighborhood during a daylight. At night the streets are missing street lights so it gets quite dark. "
    0
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  • lc0425
    "There are dog walkers all the time. There are no sidewalks though makes it difficult. Everyone has big yards so easy to let them outside."
    0
    Flag
  • Kvarekova
    "Big lots, a lot of trees, safe area, great schools, wonderful YMCA, 5 min drive to all important stores."
    1
    Flag
  • deecat236
    "Easy access to to RT 15 for commuting, but private site with ample room for children to play. The legal in-law unit is a big plus."
    0
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  • Jarnett81
    "My home for over 23 years, Orange is the perfect community to raise a family. This quiet township boast some of the finest schools in CT, while being fiscally well run. Orange is a very safe community with friendly, concerned, and active citizens."
    1
    Flag

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Off Market Homes Near 535 Highfield Dr

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