30 Overlook Drive
Madison, CT 06443
Madison Center
4 Beds
2.5 Baths
2,855 sqft (on 0.92 acres)
4 Beds
2.5 Baths
2,855 sqft
(on 0.92 acres)
Local Information
- Map ViewExplore the area around 30 Overlook Drive.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1963
Lot Size
0.92 acres
Living Area
2,855 sqft
Price/Sqft
$436
Parking
2 Car Garage
HOA
$108/Monthly
About this House
Location! Location! Location! Enjoy breathtaking views overlooking the Madison Golf Course & panoramic views of Long Island Sound not available from any other home in Madison. This amazing house has a Midcentury Modern flair with 2,855 total sf. Offering desirable 1-level living on the main floor consisting of: 3 BRs, an office, 2.5 Bths, Sunroom, Eat-in Kitchen & Dining Rm. Additionally, below, there is a partially finished walk-out lower level. Upon entering the inviting Living Rm has floor to ceiling windows with views & a gas fireplace w/marble surround. The Dining Rm also has spectacular water/golf views & sliders that open up to a spacious wood deck where you can enjoy dining al fresco or sunset cocktails. The Primary BR Ste has sliders to the spacious wood deck, where you can wake up w/your morning coffee or soak up the afternoon sun. The other BRs feature vaulted ceilings & carpeting, providing a sense of spaciousness. The stunning Sunroom features vaulted wood ceilings & skylights, creating a warm & cozy atmosphere, as well as a set of sliders providing access to the deck-perfect for enjoying the warmer weather. This property is conveniently located mile from downtown Madison- offering easy access to numerous restaurants, cafes, shops & a cinema for your enjoyment. The Surf Club is just a stone's throw away - and has a life-guarded beach w/various amenities such as a grill & seafood outdoor restaurant, bocce ball courts, barbecue & picnic spots, & athletic field If you are a golfer, the Madison Country Club is just a stroll away to play your game. No need to get in your car & drive over! Don't wait to schedule your private tour of this incredible house! Start creating memories in your beautiful home today!
30 Overlook Drive, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 2,855 sqft single-family home in Madison Center, built in 1963. It last sold for $1,050,000 on Aug 9, 2024 (13% below the $1,200,000 asking price). It is currently off market. The Trulia Estimate is $1,244,500, with a rent estimate of $4,872/month.
Home Details for 30 Overlook Drive
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Interior Details Basement: Partial,Heated,Interior Entry,Partially Finished,Liveable SpaceNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room, Media Room, Sun Room |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2855 Square Feet |
Appliances & Utilities Appliances: Electric Cooktop, Oven, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Electric Water Heater, Water HeaterDishwasherDryerLaundry: Lower LevelMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
Windows, Doors, Floors & Walls Door: Storm Door(s) |
View Has a ViewView: Golf Course, Water |
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Exterior Home Features Roof: AsphaltPatio / Porch: DeckExterior: Breezeway, Rain Gutters, Lighting, 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,Garage Door Opener |
Frontage Waterfront: Walk to WaterNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 2423 Square FeetFinished Area (below surface): 432 Square Feet |
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Year Built Year Built: 1963 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary,Ranch |
Building Construction Materials: Vertical Siding, Brick, CedarNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 1154696 |
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Price List Price: $1,200,000 |
Status Change & Dates Off Market Date: Sat Jul 27 2024Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: Madison |
School Information Elementary School: JM JeffreyJr High / Middle School: Per Board of EdHigh School: Daniel Hand |
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Buyer Agent Buyer Company Name: Lisa Rollins Team |
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Building Area Building Area: 2855 Square Feet |
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Community Features: Basketball Court, Bocci Court, Golf, Library, Park, Playground, Private School(s), Shopping/Mall |
Other Playground |
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HOA Fee Includes: Snow Removal, Road MaintenanceHas an HOAHOA Fee: $1,300/Annually |
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Lot Area: 0.92 acres |
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Energy Efficiency Features: Thermostat, Doors |
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BasementMls Number: 24005475Attic: Access Via HatchWater ViewWater View: WaterAbove Grade Unfinished Area: 2423 |
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Basketball CourtBocci CourtGolfLibraryParkPlaygroundPrivate School(s)Shopping/Mall |
Last check for updates: about 19 hours ago
Listed by Lisa P. Rollins, (203) 671-0295
Compass Connecticut, LLC, (203) 245-1593
Co-Listing Agent: Anne Marie Straka, (203) 464-3890
Compass Connecticut, LLC, (203) 245-1593
Bought with: Lisa P. Rollins, (203) 671-0295, Compass Connecticut, LLC, (203) 245-1593
Source: Smart MLS, MLS#24005475
Price History for 30 Overlook Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 08/09/2024 | $1,050,000 | Sold | Smart MLS #24005475 |
| 07/27/2024 | $1,200,000 | Pending | Smart MLS #24005475 |
| 06/19/2024 | $1,200,000 | PriceChange | Smart MLS #24005475 |
| 05/10/2024 | $1,295,000 | PriceChange | Smart MLS #24005475 |
| 04/05/2024 | $1,385,000 | Listed For Sale | Smart MLS #24005475 |
| 07/08/2022 | $800,000 | Sold | Smart MLS #170471483 |
| 05/21/2022 | $895,000 | Contingent | Smart MLS #170471483 |
| 03/21/2022 | $895,000 | Pending | William Raveis Real Estate, Mortgage & Insurance #170471483 |
| 03/10/2022 | $895,000 | Listed For Sale | Smart MLS #170471483 |
Market trends in Madison
Last updated June 2026
Avg. sale price
$763K
Sale-to-List Price
100.7%
Price per sq ft
$327
Available listings
71
2MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $13,794 |
| Assessment | $615,000 |
Home facts updated by county records
Comparable Sales for 30 Overlook Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.33 | Single-Family Home | $895,000 | 02/02/26 | 4 | 2.5 | 2,691 | |
0.30 | Single-Family Home | $1,100,000 | 12/18/25 | 4 | 2.5 | 3,031 | |
0.22 | Single-Family Home | $1,400,000 | 05/01/26 | 4 | 5 | 3,779 | |
0.36 | Single-Family Home | $941,000 | 10/01/25 | 3 | 3 | 2,393 | |
0.66 | Single-Family Home | $1,400,000 | 07/17/26 | 4 | 3 | 3,046 | |
0.25 | Single-Family Home | $1,186,900 | 05/08/26 | 3 | 2.5 | 1,712 | |
0.24 | Single-Family Home | $1,453,000 | 08/29/25 | 5 | 3.5 | 2,647 | |
0.43 | Single-Family Home | $503,000 | 01/30/26 | 3 | 1.5 | 1,346 | |
0.45 | Single-Family Home | $2,001,250 | 01/28/26 | 4 | 3.5 | 3,400 | |
0.46 | Single-Family Home | $799,000 | 11/25/25 | 3 | 1 | 1,382 |
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Assigned Schools
These are the assigned schools for 30 Overlook Drive.
- J. Milton Jeffrey Elementary School
- K-3
- Public
- 407 Students
10/10GreatSchools RatingParent Rating AverageExcellent. Jeffrey school IS the place to be!Parent Review8y ago - Daniel Hand High School
- 9-12
- Public
- 751 Students
10/10GreatSchools RatingParent Rating AverageI feel very unsafe when in the presence of many school administrators. I wouldn’t wish the experience I’ve had here on my worst enemy. I feel constantly harassed by some teachers but more namely the school administrators, including the Vice principal. Every day I try to come in with a positive attitude about this place, but someone has to ruin it. There are however some teachers that do a great job teaching and making everyone feel safe, but the negatives outweigh this way too much.Student Review1y ago - Dr. Robert H. Brown Middle School
- 4-5
- Public
- 361 Students
9/10GreatSchools RatingParent Rating AverageThe school is great. The teachers help you as much as they can and they want you to have as much fun as possible. At the end of every trimester some related arts classes let parents come to the school to watch there kid (in Xylorythems, Theater arts, Music and Art.) There is some bullying but you can quicky report if someone is bullying you and they will quickly handle it.Student Review3y ago - Walter C. Polson Upper Middle School
- 6-8
- Public
- 541 Students
9/10GreatSchools RatingParent Rating AverageMy kids are currently attending Polson MS and are receiving an excellent education that is preparing them for high school and beyond. The course work is challenging and homework is not lacking, however, the teachers are readily available to the students for extra help before and after school. But even with all the hard work the school has great spirit and the kids have fun either in sports, theater, music or what ever their area of interest is. The schools drew us to Madison and the location has kept us! GREAT TOWN! I believe the parent involvement in the school system is a primary driver for why the school system is so successful.Parent Review14y ago 
Check out schools near 30 Overlook Drive.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Madison Center
At least 1 Trulia users voted on each feature.
100 % Say it's walkable to grocery stores
100 % Say it's walkable to restaurants
100 % Say it's dog friendly
100 % Say there's wildlife
100 % Say neighbors are friendly
50 % Say there are community events
50 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 30 Overlook Drive
- NEWOPEN SUN, 11-1PMCOMING SOON 8/20.83 ACRESDan Combs Real Estate
NEW CONSTRUCTION0.46 ACRESWilliam Raveis Real Estate
1.6 ACRESColdwell Banker Realty
0.7 ACRESBerkshire Hathaway NE Prop.
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Off Market Homes Near 30 Overlook Drive
SOLDJUL 27, 2026Berkshire Hathaway NE Prop.
SOLDJUL 27, 2026Coldwell Banker Realty
SOLDJUL 24, 2026William Raveis Real Estate
SOLDJUL 22, 2026William Pitt Sotheby's Int'l
SOLDJUL 19, 2026William Raveis Real Estate
SOLDJUL 17, 2026William Raveis Real Estate
SOLDJUL 17, 2026William Pitt Sotheby's Int'l
SOLDJUL 17, 2026Coldwell Banker Realty
SOLDJUL 10, 2026William Pitt Sotheby's Int'l- See more homes for sale inMadison
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