285 Willow Rd, Guilford, CT 06437
Property image
Property image
OFF MARKET

$952,100

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,123 sqft (on 0.92 acres)

285 Willow Rd, Guilford, CT 06437

Est. Refi. Payment $6,858/mo*
Refinance Your Home
Currently Off Market - Sold Nov 16, 2015 for $485,000

Home Value

Trulia Estimate
$952K
Since last month
Decreased$15K (-1.5%)
Since last year
Increased$11K (+1.1%)
Since last sale
Increased$469K (+96.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +95% in the last 10 years
MonthEstimated value
2026
September 2026$954K
August 2026$959K
July 2026$969K
June 2026$997K
May 2026$970K
April 2026$960K
March 2026$937K
February 2026$916K
January 2026$907K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
322 Willow Road, Guilford, CT
0.07
Single-Family Home
$980,000
07/06/26
4
2.5
4,332
200 Whitethorn Drive, Guilford, CT
0.30
Single-Family Home
$675,000
06/29/26
4
2.5
2,460
11 Timber Lane, Guilford, CT
0.42
Single-Family Home
$1,550,000
08/27/26
4
3.5
4,673
65 Ironwood Road, Guilford, CT
0.35
Single-Family Home
$1,250,000
07/17/26
4
5
5,875
795 Nut Plains Road, Guilford, CT
0.98
Single-Family Home
$800,000
10/08/25
4
2.5
3,635
7 Timber Lane, Guilford, CT
0.49
Single-Family Home
$1,550,000
07/03/26
4
3.5
5,220
45 Milano Pond Drive, Madison, CT
0.82
Single-Family Home
$795,000
07/15/26
3
2.5
1,908
51 Country Way, Madison, CT
0.84
Single-Family Home
$850,000
07/24/26
4
2.5
2,665
47 Valley Shore Drive, Guilford, CT
0.93
Single-Family Home
$589,999
07/21/26
4
2
2,388
18 Saint Francis Woods Road, Madison, CT
0.95
Single-Family Home
$550,000
07/08/26
3
2.5
1,824

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
322 Willow Road, Guilford, CT 06437
0.07
$980,000
4
2.5
4,332
Recently Sold
5 Marilyns Lane, Guilford, CT 06437
0.13
$1,205,300
4
3.5
4,472
Off Market
381 Willow Road, Guilford, CT 06437
0.19
$1,031,200
4
2.5
3,597
Off Market
Lot 1 Chestnut Grove, Guilford, CT 06437
0.26
$1,568,300
4
4.5
3,800
Off Market
95 Pepperbush Lane, Guilford, CT 06437
0.28
$1,045,900
4
3.5
3,307
Off Market
150 Whitethorn Drive, Guilford, CT 06437
0.28
$794,900
4
3
2,997
Off Market
38 Pepperbush Lane, Guilford, CT 06437
0.30
$977,600
4
2.5
3,318
Off Market
Lot 3 Chestnut Grove, Guilford, CT 06437
0.27
-
-
-
-
Off Market
53 Broad Hill Circle, Guilford, CT 06437
0.28
$770,700
3
2.5
2,779
Off Market
200 Whitethorn Drive, Guilford, CT 06437
0.30
$675,000
4
2.5
2,460
Recently Sold
459 Willow Road, Guilford, CT 06437
0.33
$1,028,300
4
2.5
3,644
Off Market
7 Chestnut Court, Guilford, CT 06437
0.30
$918,800
4
2.5
2,644
Off Market

Local Information

  • Map ViewExplore the area around 285 Willow Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1997
0.92 acre lot
3,123 sqft
$305/sqft
Garage

About this House

Welcome to one of Guilford's most attractive and established neighborhoods. This 4-bedroom, 3,123-sq-ft Colonial, situated on nearly one acre of maturely landscaped property, exemplifies many reasons why. The entranceway leads directly into the home's main living areas, with the living room to one side, the family room to the other. The breezy hallway in between, showcasing the first floor's handsome oak flooring, leads to the bright kitchen appointed with wood cabinetry, granite countertops and stainless steel appliances. Sliding doors open to a multi-level deck, in-ground pool and private backyard. A mudroom and half bath add convenience. Upstairs, the master bedroom boasts a large walk-in closet and private bath. Three additional, good-size bedrooms include a full bath. Both the third-floor bonus room is a cozy retreat and the finished, walk-out basement add to the home's friendly design.
285 Willow Rd, Guilford, CT 06437 is a 4 bedroom, 3 bathroom, 3,123 sqft single-family home built in 1997. It last sold for $485,000 on Nov 16, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $952,100, with a rent estimate of $4,494/month.

Home Details for 285 Willow Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Other
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1997Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 2

Lot Information

Lot Area: 0.92 acres

Price and Tax history

DateEventPrice
Nov 16, 2015
Source: Smart MLS #N10036173
Sold
$485,000
Sep 2, 1997
Source: N/A
Sold
$300,000

Market trends in Guilford

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$658K
$91KMoM
Sale-to-List Price
101.6%
0.8%MoM
Price per sq ft
$300
$5MoM
Available listings
69
6MoM

Around this home

What Locals Say about Guilford

At least 86 Trulia users voted on each feature.

  • 93 % Say parking is easy

  • 89 % Say car is needed

  • 89 % Say yards are well-kept

  • 88 % Say it's dog friendly

  • 81 % Say there's holiday spirit

  • 79 % Say there's wildlife

  • 78 % Say people would walk alone at night

  • 74 % Say it's quiet

  • 71 % Say neighbors are friendly

  • 71 % Say they plan to stay for at least 5 years

  • 69 % Say kids play outside

  • 54 % Say there are community events

  • 36 % Say it's walkable to restaurants

  • 35 % Say streets are well-lit

  • 27 % Say there are sidewalks

  • 19 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Djjonesey
    "Great to raise a family, schools are great, people are nice, it’s a perfect New England coastal town."
    0
    Flag
  • Micaelad
    "No sidewalks making walking difficult and ticks are a problem in CT. Electric fences are common but you have to watch for coyotes. "
    0
    Flag
  • Hrj6qvgnfj
    "Super dog friendly. People leave water and treats out along the road from the town green to the beach!"
    2
    Flag
  • Hrj6qvgnfj
    "Friendly people. Awesome town green! Best on the ct shoreline! Dog friendly. One of my neighbors has dog bowl with water for passing dognitaries!"
    1
    Flag
  • Hrj6qvgnfj
    "Guilford is like living in a New England vacation town near the beach with easy train to nyc! Best town ion the connecticut shoreline!!!! "
    1
    Flag
  • Hrj6qvgnfj
    "Amazing location. Best town green on shoreline. Trains to nyc. Steps to the Long Island sound. Great schools. Community is great. "
    1
    Flag
  • Jv4450
    "Good school system. Taxes are high especially if you are retired and have no children in the school system. "
    0
    Flag
  • Hrj6qvgnfj
    "The town green is the most beautiful on the connecticut shoreline! Concerts and community support is amazing. The minute you get off 95 it is gorgeous. It’s a tolerant community and there are trains to nyc. There is theatre all around. Long Wharf. Yale Rep. And the coastline!"
    2
    Flag
  • Ed
    "Warm and friendly and very accepting of all races and religions Great town feels small but it very sweet "
    2
    Flag
  • Sawsankibbi
    "Great school system and great teachers, choosing Guilford as a place to live was one of my best decisions."
    0
    Flag
  • Kevin.charbonneau
    "15 mins to New Haven. Easy access to buses and trains. Almost half way between New York and Boston. "
    0
    Flag
  • Cleaningangys
    "Great place for live. We live 4 year and is great. My family is happy with the area. The neighbors are friendly "
    0
    Flag
  • Sawsankibbi
    "Summer Picnic and parade, tag sale, Halloween, bonfire and much more that makes my neighborhood very special!"
    0
    Flag
  • Trulia User
    "Guilford is a safe community especially for our kids, we are lucky to live in it. The school system is very good too."
    0
    Flag
  • Charles B.
    "You need to visit to understand how great town is. Kids bike to friends houses. Out door concerts for parents."
    1
    Flag
  • Kiley H.
    "Great safe place to live! I loved growing up here. Guilford high school was tough, a lot of bullying.. but it was still a great education. The guilford green is beautiful "
    7
    Flag
  • Melissa B.
    "Excellent schools, excellent teachers, but the culture here puts a lot of pressure on kids to achieve academically and do lots of extracurriculars, which can lead to anxiety & depression. The school district is actively focusing on improving the mental health of the students, though, so hopefully that problem will dissipate. Not many real neighborhoods here, so in most areas kids can’t just go outside and find friends to play with — you have to organize play dates. A lot of conformity amongst both adults and kids. "
    2
    Flag
  • lo jor
    "Friendly neighbors, quiet roads for walking or biking. Timberlands neighborhood is a beautiful safe and friendly area, convenient to everything, town, beaches, Rt. 80 is the best main way to Yale/New Haven with no traffic (beats I-95)! Timberlands has very nice river and lakes."
    12
    Flag
  • Robinson_269@msn.com
    "The green is close by and they provide poop bags. People are friendly and understanding of others with or without dogs. "
    8
    Flag
  • Baker9493
    "Tucked away, behind lake Quonnipaug. Up in the woods, pet friendly which makes for great hikes on the trails around. Very quiet neighborhood"
    0
    Flag
  • Kprthstn
    "We have neighborhood get-togethers, we all know each other, it’s a great place to live! The kids love to play together "
    0
    Flag
  • Maximillian W.
    "I've been coming to Guilford since I was a kid to visit my grandparents and have lived here now for about two years. It's one of the best towns on the shoreline "
    1
    Flag
  • Melissa B.
    "We live about a 10-minute drive from the train station and the center of town and a 20 to 30-minute drive to New Haven, depending on traffic. "
    0
    Flag
  • Tyler P.
    "Trunk or treat and the fair and the spelling bee and talent shows and toys for tots and there’s a window painting and book sale "
    0
    Flag
  • Kelsey b. p.
    "My commute is pretty easy, the back roads are usually clear of traffic and getting to the high way or routes are easy "
    0
    Flag
  • Dennis T.
    "Woods, lakes, ocean, historical homes, and shopping. This is a great community and we couldn't be happier here."
    1
    Flag
  • Dennis T.
    "Not too far from woods, farms, the ocean, the lake, or New Haven. Really this neighborhood is the ultimate balance of quiet country life and close to the city. A walk to the town green, but not too much traffic."
    2
    Flag
  • Lisa
    "My neighborhood is on a Private road in the woods...very quiet an secluded away from noise and traffic. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 285 Willow Rd

  • What is 285 Willow Rd estimated to be worth?
    Trulia's estimated value for 285 Willow Rd in Guilford, CT is $952,100.
  • What is the price history for 285 Willow Rd?
    285 Willow Rd in Guilford, CT last sold for $485,000 in November 2015.
  • Is Guilford a buyer's or seller's market?
    Guilford is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Guilford?
    The median sale price in Guilford is $658K. That is up $91K from the prior month.
  • How big is the lot at 285 Willow Rd?
    The lot at 285 Willow Rd in Guilford, CT is about 0.92 acres (40,075 sq ft).
  • Does 285 Willow Rd have a garage?
    Yes, 285 Willow Rd in Guilford, CT has a garage.

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