39 Brookside Dr, Guilford, CT 06437
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Property image
OFF MARKET

39 Brookside Dr
Guilford, CT 06437

  • 3 Beds
  • 2 Baths
  • 1,640 sqft (on 0.25 acres)

$480,300

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $3,385/mo*
Refinance Your Home

$480,300

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $3,385/mo*
Refinance Your Home
3 Beds
2 Baths
1,640 sqft
(on 0.25 acres)

Home Value

Trulia Estimate
$480K
Since last month
Increased$500 (+0.1%)
Since last year
Increased$15K (+3.3%)
Since last sale
Increased$214K (+80.9%)
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 +96% in the last 10 years
MonthEstimated value
2026
August 2026$479K
July 2026$479K
June 2026$485K
May 2026$482K
April 2026$474K
March 2026$463K
February 2026$453K
January 2026$446K
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
90 Cedar Hill Road, Guilford, CT
0.13
Single-Family Home
$449,000
02/02/26
3
1.5
1,296
79 Fall Road, Guilford, CT
0.19
Single-Family Home
$425,000
12/30/25
3
2
2,150
24 Echo Point Road, Guilford, CT
0.26
Single-Family Home
$434,000
04/17/26
3
2.5
1,825
14 Hazel Road, Guilford, CT
0.53
Single-Family Home
$440,000
11/14/25
2
1
1,334
296 Valley Shores Drive, Guilford, CT
0.79
Single-Family Home
$525,000
04/01/26
3
2
1,732
296 Valley Shore Dr, Guilford, CT
0.78
Single-Family Home
$525,000
04/02/26
3
2
1,332
529 North Madison Road, Guilford, CT
0.22
Single-Family Home
$430,000
09/15/25
2
1
1,580
91 Russo Drive, Guilford, CT
0.77
Single-Family Home
$565,000
05/15/26
3
2
2,438
200 Whitethorn Drive, Guilford, CT
0.48
Single-Family Home
$675,000
06/29/26
4
2.5
2,460
87 White Birch Drive, Guilford, CT
0.45
Single-Family Home
$487,500
04/03/26
1
1
936

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
5 Laurel Road, Guilford, CT 06437
0.10
$398,400
2
1.5
1,254
Off Market
52 Milford Road, Guilford, CT 06437
0.08
$511,800
3
2.5
1,804
Off Market
115 Middle Road, Guilford, CT 06437
0.10
$427,200
2
2
1,353
Off Market
70 Cedar Hill Road, Guilford, CT 06437
0.12
$425,500
4
2
1,814
Off Market
90 Cedar Hill Road, Guilford, CT 06437
0.13
$449,000
3
1.5
1,296
Recently Sold
145 Middle Road, Guilford, CT 06437
0.13
$509,600
3
1
1,533
Off Market
97 Cedar Hill Road, Guilford, CT 06437
0.17
$553,100
3
2
1,768
Off Market
560 North Madison Road, Guilford, CT 06437
0.16
$429,600
3
1.5
1,192
Off Market
79 Fall Road, Guilford, CT 06437
0.19
$425,000
3
2
2,150
Recently Sold
529 North Madison Road, Guilford, CT 06437
0.22
$445,000
2
1
1,580
Off Market
35 Whitethorn Drive, Guilford, CT 06437
0.25
$742,100
5
3.5
3,010
Off Market
513 North Madison Road, Guilford, CT 06437
0.25
$569,900
3
2
1,775
Off Market

Local Information

  • Map ViewExplore the area around 39 Brookside Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1950
Lot Size
0.25 acres
Living Area
1,640 sqft
Price/Sqft
$293
Parking
Garage

About this House

"The Little House" as the owner refers to this sweet Cape, that sits on a sunny knoll is at the center of "Guilford Lakes" region of Guilford. Great starter home or weekend getaway. Association beach at the Lower Lake and boat rack on Middle Lake. A babbling brook across the street from the house is a welcome sound! Beautiful public golf course and the Guilford Lakes Intermediate School are both a short distance away. The house offers 3 bedrooms, and 2 full baths....(please note 1 full bath on main floor and second full bath on lower finished basement level) Large LR with working fireplace. Eat-in kitchen w/sldrs to deck. Very nice wood flooring on the first floor and a terrazzo floor in the large finished basement. Nice front porch and side deck. Stone wall terracing in the back of house offers great appeal and gardening possibilities. Small view of brook from front porch. All measurements approx.
39 Brookside Dr, Guilford, CT 06437 is a 3 bedroom, 2 bathroom, 1,640 sqft single-family home built in 1950. It last sold for $265,000 on Jul 11, 2018. More recently, it was listed as a rental in February 2015 with an asking price of $1,850 per month. That rental listing was removed on March 25, 2015. It is currently off market. The Trulia Estimate is $480,300, with a rent estimate of $3,856/month.

Home Details for 39 Brookside Dr

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: BaseboardHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Other
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1950Year Updated: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 10890 sqft

Price and Tax history

DateEventPrice
Jul 11, 2018
Source: Smart MLS #170050974
Sold
$265,000
Apr 26, 2018
Source: Agent Provided
Pending
$295,000
Feb 27, 2018
Source: Agent Provided
PriceChange
$295,000
Price decreased by 6%
Feb 20, 2018
Source: Agent Provided
Listed For Sale
$315,000
Mar 25, 2015
Source: Agent Provided
ListingRemoved
$1,850

Market trends in Guilford

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$567K
$44.83KMoM
Sale-to-List Price
102.4%
1.1%MoM
Price per sq ft
$305
$8MoM
Available listings
75
5MoM

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 39 Brookside Dr

  • What is 39 Brookside Dr estimated to be worth?
    Trulia's estimated value for 39 Brookside Dr in Guilford, CT is $480,300.
  • What is the price history for 39 Brookside Dr?
    39 Brookside Dr in Guilford, CT last sold for $265,000 in July 2018.
  • Is Guilford a buyer's or seller's market?
    Guilford is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Guilford?
    The median sale price in Guilford is $567K. That is up $44.83K from the prior month.
  • Does 39 Brookside Dr have laundry facilities?
    Yes, 39 Brookside Dr in Guilford, CT has in-unit laundry.
  • How big is the lot at 39 Brookside Dr?
    The lot at 39 Brookside Dr in Guilford, CT is about 0.25 acres (10,890 sq ft).

Explore by feature - Pet Friendly

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Explore by feature - Washer/dryer

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