29 Pine Dr, Madison, CT 06443
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Property image
OFF MARKET

29 Pine Dr
Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 1,396 sqft (on 1 acre)

$529,200

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,737/mo*
Refinance Your Home

$529,200

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,737/mo*
Refinance Your Home
4 Beds
3 Baths
1,396 sqft
(on 1 acre)

Home Value

Trulia Estimate
$529K
Since last month
Decreased$12K (-2.3%)
Since last year
Decreased$11K (-2%)
Since last sale
Increased$246K (+87.3%)
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 +91% in the last 10 years
MonthEstimated value
2026
August 2026$528K
July 2026$530K
June 2026$540K
May 2026$531K
April 2026$524K
March 2026$504K
February 2026$493K
January 2026$498K
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
9 Monroe Lane, Madison, CT
0.29
Single-Family Home
$640,000
06/30/26
4
2.5
1,894
37 Pine Drive, Madison, CT
0.08
Single-Family Home
$730,000
12/01/25
4
2.5
2,390
21 Pierce Lane, Madison, CT
0.26
Single-Family Home
$539,000
08/07/26
3
1.5
1,666
86 Winterhill Road, Madison, CT
0.30
Single-Family Home
$703,500
09/30/25
4
2.5
2,330
96 Winterhill Road, Madison, CT
0.25
Single-Family Home
$715,000
06/04/26
4
2.5
2,950
60 Winterhill Road, Madison, CT
0.41
Single-Family Home
$620,000
11/25/25
4
2.5
1,992
677 Durham Road, Madison, CT
0.33
Single-Family Home
$730,000
12/23/25
3
2.5
2,112
21 Little Hollow Road, Madison, CT
0.38
Single-Family Home
$725,000
04/09/26
3
2.5
1,589
25 Copperstone Lane, Madison, CT
0.47
Single-Family Home
$585,000
01/30/26
3
2.5
2,542
286 Opening Hill Road, Madison, CT
0.66
Single-Family Home
$610,000
03/27/26
4
2.5
1,870

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
28 Pine Drive, Madison, CT 06443
0.09
$819,100
3
2
2,376
Off Market
31 Pine Drive, Madison, CT 06443
0.06
$904,900
4
2.5
2,804
Off Market
37 Pine Drive, Madison, CT 06443
0.08
$730,000
4
2.5
2,390
Recently Sold
469 Warpas Road, Madison, CT 06443
0.15
$617,600
3
1.5
1,864
Off Market
23 Horsebarn Lane, Madison, CT 06443
0.11
$855,000
4
3
3,972
Recently Sold
475 Warpas Road, Madison, CT 06443
0.17
$640,200
2
2
1,302
Off Market
479 Warpas Road, Madison, CT 06443
0.23
$875,400
3
2.5
2,756
Off Market
96 Winterhill Road, Madison, CT 06443
0.25
$715,000
4
2.5
2,950
Recently Sold
86 Winterhill Road, Madison, CT 06443
0.30
$726,700
4
2.5
2,330
Off Market
21 Pierce Lane, Madison, CT 06443
0.26
$539,000
3
1.5
1,666
Recently Sold
16 Dogwood Lane, Madison, CT 06443
0.33
$971,100
3
3.5
2,574
Off Market
9 Monroe Lane, Madison, CT 06443
0.29
$640,000
4
2.5
1,894
Recently Sold

Local Information

  • Map ViewExplore the area around 29 Pine Dr.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1962
Lot Size
1 acre
Living Area
1,396 sqft
Price/Sqft
$379

About this House

Academic furnished rental not far from town, beaches and schools. This 3 bedroom ranch is set on a quiet cul-de-sac street. There's an open floor plan with living/dining combination, and an eat-in kitchen with pantry. The main level has 3 bedrooms and 1 full and 1 half bath. The lower walk-out level has a half bath and finished playroom/office. The owner is having an additional portion of the lower level finished for additional recreation space. The yard is beautiful It's bordered in the front by a picturesque stone wall. The back deck overlooks a private setting. There's a large storage shed outside too. Plenty of parking for this home, but note there is no garage. The home is available through the school year of 2020. Credit check, security deposit is required. Pets are on a case by case request.
29 Pine Dr, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 1,396 sqft single-family home built in 1962. It last sold for $281,900 on Jun 28, 2019. More recently, it was listed as a rental in June 2019 with an asking price of $1,650 per month. That rental listing was removed on August 7, 2019. It is currently off market. The Trulia Estimate is $529,200, with a rent estimate of $4,186/month.

Home Details for 29 Pine Dr

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
AtticNumber of Rooms: 6
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Vinyl
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1962Year Updated: 1962
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 1 acre

Price and Tax history

DateEventPrice
Aug 7, 2019
Source: Agent Provided
ListingRemoved
$1,650
Jun 29, 2019
Source: Agent Provided
Listed For Rent
$1,650
Jun 28, 2019
Source: Smart MLS #170153520
Sold
$281,900
May 2, 2019
Source: Agent Provided
Pending
$287,900
Feb 21, 2019
Source: Agent Provided
PriceChange
$287,900
Price decreased by 4%

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM
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Around this home

What Locals Say about Madison

At least 57 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 91 % Say parking is easy

  • 90 % Say yards are well-kept

  • 89 % Say it's dog friendly

  • 88 % Say there's wildlife

  • 85 % Say there's holiday spirit

  • 78 % Say people would walk alone at night

  • 74 % Say it's quiet

  • 66 % Say neighbors are friendly

  • 63 % Say they plan to stay for at least 5 years

  • 62 % Say kids play outside

  • 39 % Say there are community events

  • 31 % Say streets are well-lit

  • 29 % Say it's walkable to grocery stores

  • 26 % Say it's walkable to restaurants

  • 12 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Nancy Bussiere
    "My commute to work is under 15mins. I love the easy access to highways. There is public transportation available but I haven’t used it as of yet"
    0
    Flag
  • Ginavan1
    "Safe,beautiful and family oriented. Beach and hiking places nearby. Great schools and town and local sport leagues for the kids."
    0
    Flag
  • Ginavan1
    "Good schools . Neighbors are nice and welcoming. Good sense of community. Clean, safe and great outdoors."
    0
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  • Jv4450
    "I’m just trying my luck with this and it doesn’t look too great for the job and the way the company looks I just have no confidence "
    0
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  • Trulia User
    "I’ve lived here for 30 years. Home prices continue to go up with the NYC families inching this way causing taxes to get out of control. "
    1
    Flag
  • Diana
    "I see people walking dogs but there is no dog park like in neighboring towns. However, there are many walking trails that you can take your leashed dog to walk in."
    4
    Flag
  • Elizabeth L.
    "Great neighborhood. Great schools. Beautiful town. Great library. Great beaches. New England vibe. Shoreline East train takes you to new Haven with direct connection to NYC. "
    2
    Flag
  • Cassidy W.
    "Great place. Been here for 23 years, wouldn’t change a thing. Very small town. Not a lot of commercial business in Madison, close by in Guilford, very local business oriented. "
    1
    Flag
  • Diana
    "People seem friendly enough but aren’t nosy neighbors. I think it would be fairly easy for young families to socially connect."
    2
    Flag
  • Jcimino5
    "Nice community with good school system and organized sports teams. Nice beach and walking trails. Can get a bit crowded in the summer."
    2
    Flag
  • Mike H.
    "A wonderful seaside community. Colonial New England meets the beach. Great Resaurant’s and small businesses. "
    0
    Flag
  • Junedday1
    "I've lived in this neighborhood for 9 years and love it. Great neighbors, quite, well-maintained and very safe."
    3
    Flag
  • Bob B
    "Great community. Families partipate in local activities. Safe town. Beautiful town beach properties. Great local shopping and restaurants. School system is top notch and lots of state parks close by. It’s really a picture perfect town. Lived in Madison for 42 years "
    0
    Flag
  • Robuess
    "Its the best town in America hands down. We love the local restaurants and can ride our bikes to the beach. Friendly locals who will stop and ask if you need help. Very fortunate to have lived here for 40 years!!"
    0
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  • Joy J.
    "great area to live. Good neighbors, good food. beautiful backyards. Good for animals and nature.?I would definitely suggest living here"
    0
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  • Pamelajbrown1234
    "Almost everyone has a dog, we take them everywhere. There is a dog park in town. People walk their dogs all over town and down at Hammonasette State Park. Dogs mostly seem very well trained and socialized"
    7
    Flag
  • Nicole L.
    "There is a real sense of community and people actually care about each other here. Schools are excellent and our beaches make it feel like you're always on vacation. "
    0
    Flag
  • Mike H.
    "I’ve lived here since 1990 and love it! There’s everything here, from great dining and great bookstore, coffee shops and terrific local cinema!"
    0
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  • David F.
    "Great for young families!"
    0
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  • Robert S.
    "We have lived in Madison for 15 years. This is a great neighborhood with only 12 houses. It is quiet and private as well as being a friendly and considerate group of folks. Mix of retierees and families with close proximity to many local amenities."
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 29 Pine Dr

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Off Market Homes Near 29 Pine Dr

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Frequently asked questions about 29 Pine Dr

  • What is 29 Pine Dr estimated to be worth?
    Trulia's estimated value for 29 Pine Dr in Madison, CT is $529,200.
  • What is the price history for 29 Pine Dr?
    29 Pine Dr in Madison, CT last sold for $281,900 in June 2019.
  • Is Madison a buyer's or seller's market?
    Madison is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $710K. That is down $53.67K from the prior month.
  • Does 29 Pine Dr have air conditioning?
    Yes, 29 Pine Dr in Madison, CT has air conditioning.
  • Does 29 Pine Dr have laundry facilities?
    Yes, 29 Pine Dr in Madison, CT has in-unit laundry.