25 Waterside Drive, Guilford, CT 06437
OFF MARKET

$1,526,600

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 1,766 sqft

25 Waterside Drive, Guilford, CT 06437

Est. Refi. Payment $10,812/mo*
Refinance Your Home
Currently Off Market - Sold Oct 26, 2023 for $901,500

Home Value

Trulia Estimate
$1.53M
Since last month
Increased$7K (+0.4%)
Since last year
Increased$115K (+8%)
Since last sale
Increased$639K (+70.9%)
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 +95% in the last 10 years
MonthEstimated value
2026
September 2026$1.54M
August 2026$1.53M
July 2026$1.52M
June 2026$1.57M
May 2026$1.52M
April 2026$1.46M
March 2026$1.43M
February 2026$1.42M
January 2026$1.39M
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
35 Bayberry Lane, Guilford, CT
0.11
Single-Family Home
$1,025,000
12/03/25
4
2.5
3,367
51 Highland Avenue, Guilford, CT
0.81
Single-Family Home
$625,000
07/02/26
4
1.5
1,315
65 Prospect Avenue, Guilford, CT
0.72
Single-Family Home
$1,500,000
11/12/25
4
2.5
2,315
102 Colonial Road, Guilford, CT
0.38
Single-Family Home
$610,000
09/26/25
3
2
2,040
55 Harbor View Road, Guilford, CT
1.01
Single-Family Home
$625,000
02/04/26
3
2.5
1,772
136 Daniel Avenue, Guilford, CT
0.92
Single-Family Home
$1,720,000
08/05/26
1
2.5
2,041
59 Cedar Grove Road, Guilford, CT
1.12
Single-Family Home
$1,067,500
06/12/26
3
1.5
1,409
11 Island Bay Circle, Guilford, CT
1.00
Single-Family Home
$950,000
11/19/25
6
3.5
3,197

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
13 Waterside Drive, Guilford, CT 06437
0.02
$1,543,400
2
3
1,740
Off Market
10 Hillside Drive, Guilford, CT 06437
0.04
$824,200
2
1
944
Off Market
184 Old Sachems Head Road, Guilford, CT 06437
0.12
$1,099,500
3
3
2,182
Off Market
35 Bayberry Lane, Guilford, CT 06437
0.11
$1,025,000
4
2.5
3,367
Recently Sold
26 Arrowhead Drive, Guilford, CT 06437
0.16
$1,028,100
4
2.5
2,080
Off Market
281 Old Sachems Head Road, Guilford, CT 06437
0.20
$4,545,400
6
5.5
7,655
Off Market
17 Bentons Knoll #17, Guilford, CT 06437
0.22
$1,373,800
2
2.5
2,600
Off Market
65 Old Sachems Head Road, Guilford, CT 06437
0.24
$993,800
4
3.5
3,648
Off Market
7 Benton's Knoll #11, Guilford, CT 06437
0.29
$1,106,300
3
2.5
2,000
Off Market
3 Bentons Knoll, Guilford, CT 06437
0.30
$1,101,200
3
2.5
2,275
Off Market
4 Bentons Knoll #2, Guilford, CT 06437
0.31
$1,550,000
4
3.5
2,877
Recently Sold

Local Information

  • Map ViewExplore the area around 25 Waterside Drive.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1968
1,766 sqft
$864/sqft
2 Car Garage

About this House

What's unique:Lawn area
Direct ocean front! Enjoy some of the most beautiful sunsets with direct ocean views Sachems Head and Joshua Cove have to offer. The back yard has both a lawn area and direct access to the ocean. This cedar shake fully dormered cape cod needs your design ideas and tool belt. House is on septic and city water, legal bedroom count unknown although field card states 5 bedrooms, 5 baths. This information is not verified to be legal. Subject is in a coastal flood zone and may trigger the 50% rule requiring the house to be elevated above the flood plain prior to renovations. Agents do your due diligence. Sold AS-IS where is. Property is subject to a 3-5 day first look period for all offers. ***Multiple offers received, highest and best due 12pm 10/10***
25 Waterside Drive, Guilford, CT 06437 is a 5 bedroom, 5 bathroom, 1,766 sqft single-family home built in 1968. It last sold for $901,500 on Oct 26, 2023 (42% above the $635,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,526,600, with a rent estimate of $4,562/month.
Last check for updates: about 17 hours ago
Listed by Michael Delgreco, (203) 631-0832
New England Realty Assoc LLC, (203) 774-4800
Bought with: Douglas E. St. John, (203) 374-0379, New England Realty Assoc LLC, (203) 774-4800
Source: Smart MLS, MLS#170602002

Home Details for 25 Waterside Drive

Interior Features

Interior Details
Basement: FullNumber of Rooms: 9Types of Rooms: Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 1766 Square Feet
Appliances & Utilities
Appliances: None, Water Heater
Heating & Cooling
Heating: Baseboard,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: WoodFoundation: MasonryNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Attached,Asphalt
Frontage
WaterfrontWaterfront: Waterfront, Ocean FrontOn Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1766 Square Feet

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Cedar, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1114837

Price & Status

Price
List Price: $635,000
Status Change & Dates
Off Market Date: Wed Oct 11 2023Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Guilford
School Information
Elementary School: Per Board of EdHigh School: Guilford

Building

Building Area
Building Area: 1766 Square Feet

HOA

No HOA

Lot Information

Lot Area: 8712 sqft

Listing Info

Special Conditions: Real Estate Owned

Miscellaneous

BasementMls Number: 170602002Attic: Pull Down StairsWater ViewWater View: WaterAbove Grade Unfinished Area: 1766

Price and Tax history

DateEventPrice
Oct 26, 2023
Source: Smart MLS #170602002
Sold
$901,500
May 23, 2022
Source: Smart MLS #170443944
ListingRemoved
Apr 29, 2022
Source: Smart MLS #170443944
Contingent
$999,000
Oct 22, 2021
Source: Smart MLS #170443944
PriceChange
$999,000
Price decreased by 17%
Oct 8, 2021
Source: Smart MLS #170443944
Listed For Sale
$1,200,000

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

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 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
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  • 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

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 25 Waterside Drive

  • What is 25 Waterside Drive estimated to be worth?
    Trulia's estimated value for 25 Waterside Drive in Guilford, CT is $1,526,600.
  • What is the price history for 25 Waterside Drive?
    25 Waterside Drive in Guilford, CT last sold for $901,500 in October 2023.
  • 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 25 Waterside Drive?
    The lot at 25 Waterside Drive in Guilford, CT is about 0.20 acres (8,712 sq ft).
  • Does 25 Waterside Drive have a garage?
    Yes, 25 Waterside Drive in Guilford, CT has an attached garage.

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