39 Vineyard Place, Guilford, CT 06437
Property image
Property image
FOR SALE
2 ACRES

$5,950,000

  • 6 Beds
  • 5.5 Baths
  • 6,603 sqft (on 2 acres)

39 Vineyard Place, Guilford, CT 06437

Est. Mortgage $41,584/mo*
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Home Highlights

Single-Family Home
Built in 1930
2 acre lot
$901/sqft
3 Car Garage
HOA $75/mo

Local Information

  • Map ViewExplore the area around 39 Vineyard Place.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich heritage is reflected in its exquisite details, from the enduring beauty of Stony Creek Granite and warm Pecky Cypress woodwork, to the original "porthole" windows in the grand family room. In the formal dining room, a distinctive ribbed ceiling, designed to evoke the overhead of a classic ship's cabin, creates an unforgettable atmosphere for entertaining. The heart of the home features a generous galley kitchen that balances functionality with style, offering abundant cabinetry, expansive counter space, and dining area with plenty of windows making sure no view is missed. Retreat to the second floor to find six spacious bedrooms, each offering its own unique perspective of the water, while the finished third-floor "flex" space serves as an ideal game room or private sanctuary. Spread across two manicured acres, enjoy relaxed seaside living with multiple sun porches, an expansive patio for gatherings, and the rare luxury of a private boat house. Take advantage of the Vineyard Place Association amenities, all while being just a short drive from charming downtown Guilford!
Last check for updates: about 9 hours ago
Listing courtesy of Ana Russo, (203) 988-3534
William Pitt Sotheby's Int'l, (203) 988-3534
Source: Smart MLS, MLS#24155090
Also Listed on Smart MLS.

Home Details for 39 Vineyard Place

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 13Types of Rooms: Master Bedroom, Bedroom, Dining Room, Great Room, Kitchen, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6603 Square Feet
Appliances & Utilities
Utilities: Underground UtilitiesAppliances: Oven/Range, Oven, Refrigerator, Freezer, Dishwasher, Electric Water Heater, Water HeaterDishwasherLaundry: Main LevelRefrigerator
Heating & Cooling
Heating: Forced Air,Wall Unit,Zoned,ElectricHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,DuctlessHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors
View
Has a ViewView: Water
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Enclosed, Terrace, Porch, PatioExterior: Tennis Court(s), Stone Wall, Underground SprinklerFoundation: StoneNo 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
WaterfrontWaterfront: Waterfront, Beach, Walk to WaterOn Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 6603 Square Feet

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shingle Siding, StoneNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1121542

Price & Status

Price
List Price: $5,950,000Price Per Sqft: $901
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Active

Location

Direction & Address
City: GuilfordCommunity: Vineyard Place Associatio
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Agent Information

Listing Agent
Listing ID: 24155090

Building

Building Area
Building Area: 6603 Square Feet

Community

Community Features: Bocci Court, Library, Park, Playground, Public Rec Facilities, Shopping/Mall, Tennis Court(s)
Other
Playground

HOA

HOA Fee Includes: Maintenance GroundsHas an HOAHOA Fee: $900/Annually

Lot Information

Lot Area: 2 Acres

Miscellaneous

Mls Number: 24155090Attic: Heated, Storage, Partially Finished, Walk-upWater ViewWater View: WaterAttribution Contact: (203) 988-3534Above Grade Unfinished Area: 6603

Additional Information

HOA Amenities: Tennis Court(s),Lake/Beach Access

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

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

Home Value

Trulia Estimate
$5.4M
Since last month
Decreased$21K (-0.4%)
Since last year
Increased$1M (+25.7%)
Since last sale
Increased$3M (+92.5%)
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 +75% in the last 10 years
MonthEstimated value
2026
August 2026$5.39M
August 2026$5.39M
July 2026$5.41M
June 2026$5.43M
May 2026$5.47M
April 2026$5.52M
March 2026$5.69M
February 2026$4.19M
January 2026$4.01M
2025
2024
2023
2022
2021
2020

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
65 Prospect Avenue, Guilford, CT
0.33
Single-Family Home
$1,500,000
11/12/25
4
2.5
2,315
35 Bayberry Lane, Guilford, CT
0.77
Single-Family Home
$1,025,000
12/03/25
4
2.5
3,367
102 Colonial Road, Guilford, CT
0.79
Single-Family Home
$610,000
09/26/25
3
2
2,040
11 Island Bay Circle, Guilford, CT
1.66
Single-Family Home
$950,000
11/19/25
6
3.5
3,197
48 Andrews Road, Guilford, CT
1.91
Single-Family Home
$2,200,000
12/12/25
6
5
3,948
51 Highland Avenue, Guilford, CT
0.80
Single-Family Home
$625,000
07/02/26
4
1.5
1,315
194 Chaffinch Island Road, Guilford, CT
1.60
Single-Family Home
$1,330,000
01/13/26
4
3
3,150
136 Daniel Avenue, Guilford, CT
0.96
Single-Family Home
$1,720,000
08/05/26
1
2.5
2,041
Wayland Island, Branford, CT
2.38
Single-Family Home
$2,750,000
09/30/25
14
7
6,059

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
34 Prospect Avenue, Guilford, CT 06437
0.28
$2,611,800
3
2
2,495
Off Market
161 Falcon Road, Guilford, CT 06437
0.31
$7,230,600
5
6
7,671
Off Market
28 Walden Hill Road, Guilford, CT 06437
0.31
$3,750,000
5
6
5,185
For Sale
65 Prospect Avenue, Guilford, CT 06437
0.33
$1,500,000
4
2.5
2,315
Recently Sold
413 Vineyard Point Road, Guilford, CT 06437
0.33
$2,145,400
5
3.5
3,854
Off Market
473 Colonial Road, Guilford, CT 06437
0.49
$1,995,000
3
3
2,969
For Sale
620 Colonial Road, Guilford, CT 06437
0.52
$7,500,000
4
4.5
5,475
For Sale
31 Loyal Ledge Lane, Guilford, CT 06437
0.52
$4,620,200
4
4.5
4,357
Off Market
221 Vineyard Point Road, Guilford, CT 06437
0.57
$2,525,300
4
4.5
5,199
Off Market
30 Chimney Corner Circle, Guilford, CT 06437
0.58
$1,860,700
3
2.5
1,703
Off Market
47 Chimney Corner Circle, Guilford, CT 06437
0.62
$2,915,200
5
3.5
4,669
Off Market

Price and Tax history

DateEventPrice
Mar 12, 2026
Source: Smart MLS #24155090
Listed For Sale
$5,950,000
Aug 30, 2018
Source: Smart MLS #N10238974
Sold
$2,800,000
Jun 12, 2018
Source: Agent Provided
PriceChange
$3,450,000
Price decreased by 8%
Apr 13, 2018
Source: Agent Provided
PriceChange
$3,750,000
Price decreased by 4%
Jul 29, 2017
Source: Agent Provided
PriceChange
$3,900,000
Price decreased by 7%

LGBTQ Local Legal Protections

Ana Russo, William Pitt Sotheby's Int'l, (203) 988-3534
Agent Phone: (203) 988-3534
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.

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Frequently asked questions about 39 Vineyard Place

  • What is the estimated monthly payment for 39 Vineyard Place?
    Based on a $5,950,000 list price with 20% down at today's rates, the estimated monthly payment for 39 Vineyard Place in Guilford, CT is approximately $42,776 (about $32,140 principal & interest, $10,561 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 39 Vineyard Place compare to homes in Guilford?
    39 Vineyard Place in Guilford, CT is listed at $5,950,000, about 950% above the $567K median sale price in Guilford.
  • What do residents say about Guilford?
    Residents describe Guilford, CT as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See homes for sale in Guilford, CT.
  • What are the closest schools to 39 Vineyard Place?
    The closest schools to 39 Vineyard Place in Guilford, CT are A. Baldwin Middle School (Elementary, rated 8/10), A. W. Cox School (Elementary, rated 7/10), E. C. Adams Middle School (rated 8/10).
  • Does 39 Vineyard Place have air conditioning?
    Yes, 39 Vineyard Place in Guilford, CT has air conditioning.
  • Does 39 Vineyard Place have laundry facilities?
    Yes, 39 Vineyard Place in Guilford, CT has laundry facilities.
39 Vineyard Place, Guilford, CT 06437 is a 6 bedroom, 6 bathroom, 6,603 sqft single-family home built in 1930. This property is currently available for sale and was listed by Smart MLS on Mar 12, 2026. The MLS # for this home is MLS# 24155090.