9 Bailey Drive
Guilford, CT 06437
- 4 Beds
- 2.5 Baths
- 3,567 sqft (on 1.60 acres)
4 Beds
2.5 Baths
3,567 sqft
(on 1.60 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1996
Lot Size
1.6 acres
Living Area
3,567 sqft
Price/Sqft
$357
Parking
2 Car Garage
Description
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). It is currently off market. The Trulia Estimate is $1,272,300, with a rent estimate of $5,511/month.
Home Details for 9 Bailey Drive
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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 |
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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 |
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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 |
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Price List Price: $995,000 |
Status Change & Dates Off Market Date: Mon Jun 09 2025Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: Guilford |
School Information Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Per Board of Ed |
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Buyer Agent Buyer Company Name: Marshall + OstopTeam at William Raveis Real Estate |
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Building Area Building Area: 3567 Square Feet |
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No HOA |
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Lot Area: 1.6 Acres |
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BasementMls Number: 24101427Attic: Access Via HatchWater ViewWater View: WaterAbove Grade Unfinished Area: 2667 |
Last check for updates: 1 day 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

Price History for 9 Bailey Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 07/29/2025 | $1,230,000 | Sold | Smart MLS #24101427 |
| 07/17/2025 | $995,000 | Pending | Smart MLS #24101427 |
| 06/05/2025 | $995,000 | Listed For Sale | Smart MLS #24101427 |
| 11/16/2017 | $600,000 | Sold | N/A |
| 07/18/2013 | $575,000 | Sold | Smart MLS #M9139728 |
| 06/10/1993 | $85,000 | Sold | N/A |
Market trends in Guilford
Last updated June 2026
Avg. sale price
$527K
$36.67KMoM
Sale-to-List Price
—
Price per sq ft
$296
$18MoM
Available listings
70
10MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $12,010 |
| Assessment | $434,350 |
Home facts updated by county records
Comparable Sales for 9 Bailey Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.73 | Single-Family Home | $1,100,000 | 03/20/26 | 4 | 3 | 3,532 | |
0.76 | Single-Family Home | $850,000 | 01/07/26 | 4 | 3 | 3,887 | |
0.84 | Single-Family Home | $595,000 | 01/16/26 | 4 | 2.5 | 2,533 | |
0.79 | Single-Family Home | $625,000 | 06/26/26 | 4 | 2 | 2,236 | |
0.75 | Single-Family Home | $1,500,000 | 07/07/26 | 4 | 3.5 | 4,880 | |
0.53 | Single-Family Home | $620,000 | 09/30/25 | 3 | 2 | 1,788 | |
0.71 | Single-Family Home | $625,000 | 10/21/25 | 3 | 3 | 2,784 | |
0.90 | Single-Family Home | $890,000 | 12/22/25 | 4 | 3.5 | 4,346 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 9 Bailey Drive.
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.
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