5 Chestnut Grove, Guilford, CT 06437
OFF MARKET

$1,238,700

Trulia Estimate
  • 5 Beds
  • 6.5 Baths
  • 6,058 sqft (on 2.02 acres)

5 Chestnut Grove, Guilford, CT 06437

Est. Refi. Payment $8,920/mo*
Refinance Your Home
Currently Off Market - Sold Jul 24, 2024 for $1,075,000

Home Value

Trulia Estimate
$1.24M
Since last month
Decreased$37K (-2.9%)
Since last year
Increased$87K (+7.6%)
Since last sale
Increased$163K (+15.2%)
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 +67% in the last 10 years
MonthEstimated value
2026
September 2026$1.24M
August 2026$1.25M
July 2026$1.28M
June 2026$1.29M
May 2026$1.28M
April 2026$1.26M
March 2026$1.23M
February 2026$1.19M
January 2026$1.17M
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
43 Chestnut Grove, Guilford, CT
0.07
Single-Family Home
$1,150,000
08/24/26
5
5
6,610
604 West Lake Avenue, Guilford, CT
0.47
Single-Family Home
$1,050,000
11/24/25
4
5.5
5,630
19 Kimberly Drive, Guilford, CT
0.36
Single-Family Home
$655,000
10/24/25
4
2.5
2,518
4 Overlook Drive, North Branford, CT
0.66
Single-Family Home
$510,000
11/26/25
4
2.5
2,324
602 West Lake Avenue, Guilford, CT
0.47
Single-Family Home
$1,050,000
11/25/25
3
2
2,132
98 Island Avenue, Madison, CT
0.82
Single-Family Home
$3,400,000
05/15/26
4
4
4,505
191 Saddle Hill Drive, Guilford, CT
0.66
Single-Family Home
$675,000
06/12/26
3
2.5
2,238
57 Notch Hill Road, North Branford, CT
1.31
Single-Family Home
$635,000
08/28/26
5
3
4,373
134 Janeway Drive, Guilford, CT
0.68
Single-Family Home
$458,000
03/12/26
3
3
2,278

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
9 Chestnut Grove, Guilford, CT 06437
0.03
-
-
-
-
Off Market
43 Chestnut Grove, Guilford, CT 06437
0.07
$1,150,000
5
5
6,610
Recently Sold
1000 West Lake Avenue, Guilford, CT 06437
0.13
$594,700
4
2.5
2,112
Off Market
1018 West Lake Avenue, Guilford, CT 06437
0.16
$554,900
3
2
1,505
Off Market
101 Lynn Drive, Guilford, CT 06437
0.20
$1,225,100
5
4.5
4,308
Off Market
1 Laurel Hollow Road, Guilford, CT 06437
0.22
$981,100
3
2.5
3,361
Off Market
140 Chestnut Grove, Guilford, CT 06437
0.24
$1,205,000
5
3.5
4,357
Off Market
4 Oakwood Drive, Guilford, CT 06437
0.26
$783,600
4
3.5
3,064
Off Market
1 Sleepy Hollow Lane, Guilford, CT 06437
0.29
$1,104,000
4
3.5
3,948
Off Market
12 Laurel Hollow Road, Guilford, CT 06437
0.35
$1,121,400
4
3.5
2,771
Off Market
19 Kimberly Drive, Guilford, CT 06437
0.36
$689,600
4
2.5
2,518
Off Market

Local Information

  • Map ViewExplore the area around 5 Chestnut Grove.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2005
2.02 acre lot
6,058 sqft
$204/sqft
3 Car Garage

About this House

Tucked away in a desirable cul-de-sac neighborhood, this expansive residence provides ample space to meet all your needs across its 4 levels of finished living space. Step into luxury as you enter the main floor, designed for effortless entertaining and comfortable living. The open floor plan seamlessly connects the living room (or office), dining room, and a chef's kitchen featuring a center island with granite countertops, wet bar with large walk-in pantry. Gather with loved ones in the cozy family room, complete with a gas fireplace, while overlooking the expansive Trex deck adorned with a charming wooden pergola-the perfect spot for al fresco dining. Featuring 5 generously sized bedrooms, with 4 of them boasting their own private bathrooms, this home ensures that everyone can enjoy their own space and privacy. Need even more versatility? Discover the spacious bonus room, accessible via its dedicated staircase, ideal for guests or in-home business. Ascend to the finished 3rd floor, offering yet another full bathroom, providing endless possibilities for customization. Unwind in the finished lower level, featuring a full bathroom & walkout access to a serene patio area. Rest easy knowing that this home is not only spacious but well maintained, with a new furnace recently installed and the septic system upgraded to accommodate five bedrooms in 2016. Convenient to all of Guilford's amenities while providing a peaceful sanctuary to call your own.
5 Chestnut Grove, Guilford, CT 06437 is a 5 bedroom, 7 bathroom, 6,058 sqft single-family home built in 2005. It last sold for $1,075,000 on Jul 24, 2024 (10% below the $1,200,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,238,700.
Last check for updates: about 6 hours ago
Listed by Linda Toscano, (203) 520-7899
Compass Connecticut, LLC, (203) 453-6511
Bought with: Kate Jasko, (860) 304-9034, Coldwell Banker Realty, (203) 245-4700
Source: Smart MLS, MLS#24026269

Home Details for 5 Chestnut Grove

Interior Features

Interior Details
Basement: Full,Finished,Garage Access,Interior Entry,Liveable SpaceNumber of Rooms: 15Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6058 Square Feet
Appliances & Utilities
Utilities: Underground Utilities, Cable AvailableAppliances: Gas Range, Range Hood, Refrigerator, Dishwasher, Wine Cooler, Water HeaterDishwasherLaundry: Lower Level,Upper LevelRefrigerator
Heating & Cooling
Heating: Forced Air,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: DeckExterior: Rain Gutters, Stone WallFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 5086 Square FeetFinished Area (below surface): 972 Square Feet

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 2489725

Price & Status

Price
List Price: $1,200,000
Status Change & Dates
Off Market Date: Tue Jul 09 2024Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: Guilford
School Information
Elementary School: A. W. CoxJr High / Middle School: Adams, BaldwinHigh School: Guilford

Agent Information

Buyer Agent
Buyer Company Name: Cathy Lynch & Team

Building

Building Area
Building Area: 6058 Square Feet

Community

Community Features: Golf, Health Club, Lake, Library, Medical Facilities, Paddle Tennis, Park, Shopping/Mall

HOA

No HOA

Lot Information

Lot Area: 2.02 Acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24026269Attic: Heated, Finished, Walk-upAbove Grade Unfinished Area: 5086

Additional Information

GolfHealth ClubLakeLibraryMedical FacilitiesPaddle TennisParkShopping/Mall

Price and Tax history

DateEventPrice
Jul 24, 2024
Source: Smart MLS #24026269
Sold
$1,075,000
Jul 20, 2024
Source: Smart MLS #24026269
Pending
$1,200,000
Jun 19, 2024
Source: Smart MLS #24026269
Listed For Sale
$1,200,000
Jun 18, 2024
Source: Smart MLS #24016451
ListingRemoved
May 11, 2024
Source: Smart MLS #24016451
Listed For Sale
$1,250,000

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
    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

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 5 Chestnut Grove

  • What is 5 Chestnut Grove estimated to be worth?
    Trulia's estimated value for 5 Chestnut Grove in Guilford, CT is $1,238,700.
  • What is the price history for 5 Chestnut Grove?
    5 Chestnut Grove in Guilford, CT last sold for $1,075,000 in July 2024.
  • 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.
  • Does 5 Chestnut Grove have air conditioning?
    Yes, 5 Chestnut Grove in Guilford, CT has air conditioning.
  • Does 5 Chestnut Grove have laundry facilities?
    Yes, 5 Chestnut Grove in Guilford, CT has laundry facilities.

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