9 Bailey Drive, Guilford, CT 06437
OFF MARKET

$1,283,200

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 3,567 sqft (on 1.60 acres)

9 Bailey Drive, Guilford, CT 06437

Refinance Your Home
Currently Off Market - Sold Jul 29, 2025 for $1,230,000

Home Value

Trulia Estimate
$1.28M
Since last month
Increased$10K (+0.8%)
Since last year
Increased$45K (+3.6%)
Since last sale
Increased$52K (+4.3%)
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 +158% in the last 10 years
MonthEstimated value
2026
August 2026$1.28M
August 2026$1.28M
July 2026$1.27M
June 2026$1.27M
May 2026$1.26M
April 2026$1.25M
March 2026$1.26M
February 2026$1.26M
January 2026$1.27M
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
425 Schoolside Lane, Guilford, CT
0.23
Single-Family Home
$801,000
07/29/26
4
3
2,383
2111 Jennifers Drive, Guilford, CT
0.73
Single-Family Home
$1,100,000
03/20/26
4
3
3,532
15 Briarwood Drive, Guilford, CT
0.76
Single-Family Home
$850,000
01/07/26
4
3
3,887
53 Orchard View Road, Guilford, CT
0.54
Single-Family Home
$625,000
08/13/26
4
3
2,329
54 Coachlamp Lane, Guilford, CT
0.84
Single-Family Home
$595,000
01/16/26
4
2.5
2,533
148 Highwoods Drive, Guilford, CT
0.79
Single-Family Home
$625,000
06/26/26
4
2
2,236
14 Fox Ridge, Guilford, CT
0.75
Single-Family Home
$1,500,000
07/07/26
4
3.5
4,880
33 Woodside Road, Guilford, CT
0.53
Single-Family Home
$620,000
09/30/25
3
2
1,788
472 Saw Mill Road, Guilford, CT
0.71
Single-Family Home
$625,000
10/21/25
3
3
2,784

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
67 Bailey Drive, North Branford, CT 06437
0.03
$589,900
4
1.5
2,396
For Sale
2205 Boston Post Road #TRLR 9, Guilford, CT 06437
0.11
-
1
1
400
Off Market
83 Long Hill #83, Guilford, CT 06437
0.14
$939,600
3
4.5
2,493
Off Market
83 Long Hill Farm #83, Guilford, CT 06437
0.14
$770,000
3
2.5
2,493
Recently Sold
74 Long Hill Farm #74, Guilford, CT 06437
0.16
$555,500
2
2
1,760
Off Market
65 Long Hill Farm #', Guilford, CT 06437
0.19
$457,700
2
2
1,479
Off Market
61 Long Hill Farm, Guilford, CT 06437
0.19
$282,000
1
1
876
Off Market
68 Long Hill Farms #68, Guilford, CT 06437
0.19
$475,900
2
2
1,479
Off Market
58 Long Hill Farms #58, Guilford, CT 06437
0.19
$283,600
1
1
876
Off Market
59 Long Hill Farms #59, Guilford, CT 06437
0.19
$425,200
2
2
1,314
Off Market
65 Long Hill Farm Unit 65, Guilford, CT 06437
0.19
$395,000
2
2
1,479
For Sale

Local Information

  • Map ViewExplore the area around 9 Bailey Drive.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1996
1.6 acre lot
3,567 sqft
$360/sqft
2 Car Garage

About this House

Sitting elegantly at the end of a private cul-de-sac and overlooking Enders Pond (Strawberry Hollow) you'll find this one-of-a-kind property! This bright and beautiful 4-bedroom, 2.5-bath Colonial offers 3,000+ sq ft of thoughtfully designed living space, with incredible views from nearly every window. This very special home exudes character and charm while incorporating modern updates and amenities. The open-concept layout fills the home with natural light, highlighting its distinctive design elements and inviting atmosphere. The 1st floor is highlighted by the open concept kitchen and family room, elegant dining room, bright and sunny family room, charming laundry room and access to the porch, patio and more! Upstairs you'll find 4 well sized bedrooms including the primary suite rounded out with a modernized bath and sauna. The standout lower level is a showstopper-fully updated with a home gym area, theater space, wine cellar and even a hidden office, perfect for working or as a secret hide-away. Whether you're enjoying peaceful mornings on the deck overlooking the water, listening the birds chirp, or entertaining inside and out at this stunning property, this home delivers a lifestyle that's both elevated and comfortable. A rare find in a sought-after location and in the popular picturesque town of Guilford-don't miss this truly special property!
9 Bailey Drive, Guilford, CT 06437 is a 4 bedroom, 3 bathroom, 3,567 sqft single-family home built in 1996. It last sold for $1,230,000 on Jul 29, 2025 (24% above the $995,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,283,200, with a rent estimate of $5,536/month.
Last check for updates: about 14 hours ago
Listed by Phoebe V. Finch, (617) 645-3907
William Pitt Sotheby's Int'l, (203) 245-6700
Bought with: Elizabeth Daly-Standish, (860) 471-5070, William Raveis Real Estate, (860) 521-4311
Source: Smart MLS, MLS#24101427

Home Details for 9 Bailey Drive

Interior Features

Interior Details
Basement: Full,Heated,Storage Space,FinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3567 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Oven, Refrigerator, Freezer, Dishwasher, Wine Cooler, Water HeaterDishwasherLaundry: Main LevelRefrigerator
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Terrace, Wrap Around, DeckOther Structures: Shed(s)Exterior: Awning(s), Stone WallFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Frontage
WaterfrontWaterfront: Waterfront, Walk to WaterOn Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2667 Square FeetFinished Area (below surface): 900 Square Feet

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1120404

Price & Status

Price
List Price: $995,000
Status Change & Dates
Off Market Date: Mon Jun 09 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Guilford
School Information
Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Per Board of Ed

Agent Information

Buyer Agent
Buyer Company Name: Marshall + OstopTeam at William Raveis Real Estate

Building

Building Area
Building Area: 3567 Square Feet

HOA

No HOA

Lot Information

Lot Area: 1.6 Acres

Miscellaneous

BasementMls Number: 24101427Attic: Access Via HatchWater ViewWater View: WaterAbove Grade Unfinished Area: 2667

Price and Tax history

DateEventPrice
Jul 29, 2025
Source: Smart MLS #24101427
Sold
$1,230,000
Jul 17, 2025
Source: Smart MLS #24101427
Pending
$995,000
Jun 5, 2025
Source: Smart MLS #24101427
Listed For Sale
$995,000
Nov 16, 2017
Source: N/A
Sold
$600,000
Jul 18, 2013
Source: Smart MLS #M9139728
Sold
$575,000

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

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 9 Bailey Drive

  • What is 9 Bailey Drive estimated to be worth?
    Trulia's estimated value for 9 Bailey Drive in Guilford, CT is $1,283,200.
  • What is the price history for 9 Bailey Drive?
    9 Bailey Drive in Guilford, CT last sold for $1,230,000 in July 2025.
  • 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 9 Bailey Drive have air conditioning?
    Yes, 9 Bailey Drive in Guilford, CT has air conditioning.
  • Does 9 Bailey Drive have laundry facilities?
    Yes, 9 Bailey Drive in Guilford, CT has laundry facilities.

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Off Market Homes Near 9 Bailey Drive

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