9 Timeless Homes on the Market in Connecticut, Maine, Vermont & New Hampshire

Embark on a journey through the rich history of New England with a curated selection of nine timeless homes currently on the market in Connecticut, Maine, Vermont, and New Hampshire. From historic estates to charming residences, this collection invites discerning buyers to explore the enduring allure of these homes across the picturesque landscapes of these states.

Historic American Colonial | $21,950,000

2 Old Stone Post Road, Lyme, CT
Listing agent: Sydney Anderson & Allyson Cotton

The Loomis Tavern, a 1776 classic American colonial, was reconstructed in its present location by noted housewright Skip Broom in the 1990s. Its idyllic waterfront setting on the serene Falls Brook tidal inlet is the ideal place to go kayaking with access to nearby Hamburg Cove. The house is beautifully sited on its 3.6 acres with stone walls and a sweeping lawn leading up to the home.


Size: 4,695 sf


Price: $21,950,000


Listing details: Once inside, marvel at the many special details, including plaster walls, exquisite molding, wood beams, beautiful vintage wood floors, and custom cabinetry. The home combines old world charm with new world convenience. The 51⁄2 baths throughout have been updated, as has the kitchen with elegant marble counters and high-end appliances, including Wolf, Miele, and Sub-Zero. French doors open onto the covered deck and the large stone patio – the perfect place for entertaining and for enjoying a sunset, the abundant bird life, and the beautiful gardens.


Contact: Sydney Anderson & Allyson Cotton, Sotheby’s International Realty , +1 860.510.3449, 860.227.6016

Beautiful Cape Styled Home | $499,900

15 Laydon Ave, North Haven, CT
Listing agent: Edward Perez

Completely beautifully redone Cape styled home with first floor Primary Suite with beautiful brand new bath and an attached den/ nursery. Completely new expansive Kitchen with new everything!, New 1/2 bath and laundry added on main floor.


Size: 1,822 sf


Price: $499,900


Listing details: Must see this lovely home located very close to the town center. Very open floor plan which integrates the kitchen, living area and dining room into a beautiful working flow. Close -by are the 1/2 bath and laundry room. 2nd floor features two large bedrooms with full bath and a unique playroom/ storage room. Lovely rear yard with privacy and large shed attached to garage. Also comes with a double driveway which enables over 6 cars to park. MUST SEE!


Contact: Edward Perez, William Raveis Real Estate, +1 203-526-7548

430 Milton Rd | $3,150,000

430 Milton Rd, Goshen, CT
Listing agent: Carolyn Klemm & Peter Klemm

Discover the epitome of charm and elegance in this magnificent 1930s Colonial. 13 total rooms including 7 bedrooms with 7 full & 2 1/2 baths. Nestled on 12 acres, the property offers tranquility and privacy. Boasting 100 feet of Woodridge Lake frontage, enjoy water activities and picturesque views right at your doorstep.


Size: 5,193 sf


Price: $3,150,000


Listing details: Be immersed in a private outdoor oasis featuring an exquisite Gunite pool & spa with a mesmerizing 6’ infinity waterfall. Enjoy cozy evenings by the outdoor fireplace. Bordering both Mohawk State Forest (4,000+/- Acres) and Wyantenock State Forest (4,000+/- Acres), the property seamlessly merges with the beauty of nature, providing unparalleled serenity. A large barn with paddocks, once home to five horses, adds a touch of rustic charm to the property. Ideal for horse enthusiasts.


Contact: Carolyn Klemm & Peter Klemm, Klemm Real Estate, +1 860.488.6721, 917.864.4940

307 Route 41 | $535,000

307 Route 41, Winthrop, ME
Listing agent: John Blouin

Like new! A 1784 colonial home with 6 bedrooms and 3 full baths on a 18.92 acres in desirable Winthrop with privacy galore in a home that has been remodeled professionally. This home has been lovingly cared for and includes over 3700 square feet on three floors of living. The first floor offer s sunroom with cathedral ceilings. and windows overlooking the expansive rear lawn and fields and a propane stove for toasty living. The kitchen with custom Oak cabinets, quartz countertops, tile and includes a center island.


Size: 3,704 sf


Price: $535,000


Listing details: A brick hearth and a restored wood cookstove from back in the day. The open concept kitchen flows to the breakfast are that has custom paneled wainscoting and built ins. and wood ceilings. There are two living rooms and one has a brick hearth and propane stove. The formal dining room is adjacent and perfect for gatherings This floor has wood beamed ceilings and wood ceilings that have traditional charm and beauty. A first floor primary bedroom has custom wide wood board walls ,bookcases and a full contemporary bathroom. There is over 2000 square feet of living on the first floor. The home is bathed in natural light and the sunrises are spectacular beaming over the rear lawns and fields that are expansive. The second floor offers 3 bedrooms and two full baths.


Contact: John Blouin, Vallee Harwood & Blouin Real Estate, +1 207-446-7708

Listing agent: David Brown

Beautiful 18th century solid post & beam cape on nearly 260 acres has many original features including fireplaces, wood flooring and exposed beams. Large rooms and windows provide a wonderful place for gatherings. Recently updated roof and furnace.


Size: 2,741 sf


Price: $1,500,000


Listing details: Property is a mixture of woodlots and beautiful open fields with trails going past streams, waterfalls and stone walls. Outbuildings include a barn, chicken coop, 2-car garage and a newer 40 x 60 metal barn for equipment & storage. Plus a one-bedroom guest house with a private deck & pool that could also be an Airbnb; ski resorts are only 20 minutes away. Land has frontage on three roads making it ideal for a private compound. This peaceful retreat has been in the same family for three generations and off.


Contact: David Brown, Berkley & Veller Greenwood Country Realtors, +1 802.579.9966

Historic Farmhouse | $1,995,000

2193 Hollister Hill Rd, Marshfield, VT
Listing agent: Sue Aldrich

Historic 1825 brick farmhouse, meticulously restored, blending timeless charm with modern updates. A working farm with well-maintained barns, pastures, orchards, and diverse livestock, including Angus beef cattle, sheep, pigs, chickens, donkeys, and barn cats.


Size: 4,600 sf


Price: $1,995,000


Listing details: The country kitchen offers the joy of cooking with homegrown produce, and the wraparound porch provides the perfect setting for enjoying sunsets. This property is not just a home; it’s an idyllic retreat for large families or a charming bed and breakfast, offering the tranquility of Vermont’s countryside with the potential for farm rental income.


Contact: Sue Aldrich, Coldwell Banker Realty, +1 802.839.0213

Timeless Elegant Farmhouse. | $1,250,000

44 Randall Road, Moultonborough, NH 03254
Listing agent: Dakota Coburn

Timeless Elegance Meets Rural Serenity: Historic 1778 Farmhouse on 18 Acres. This property boasts over 18 acres of sprawling pastures, a horse stable, a large barn, a private pond, and an additional 2-bedroom, 1-bath cottage (summer home). Nestled in the heart of the Lakes Region, you’ll find this gorgeous farmhouse.


Size: 3,824  sf


Price: $1,250,000


Listing details:  It consists of 2 spacious bedrooms with ensuite bathrooms in the main house, along with 2 bedrooms and a 3/4 bathroom over the garage. The kitchen features a vaulted ceiling with exposed beams, and a stunning formal living room overlooks the private pond and expansive backyard. Calling all horse lovers! The barn comes with two horse stalls and ample space for your tractors and hay. Alternatively, you can consider converting the garage into your toy shed, with plenty of room for your large boat, snowmobiles, or any other items you desire. If you’re looking for a place to host friends or family, look no further.


Contact: Dakota Coburn, Realty One Group Next Level , +1 603.707.6510

Historic Farmhouse| $2,100,000

12 Pendexter Rd, Madbury, NH
Listing agent: Jamieson Duston

Welcome to Pendexter Farm – a quintessential double chimney colonial farmhouse built in 1785. The home has been fully modernized, yet it retains its original/historic charm! Prominently situated on nearly 11-acres, the property is bordered by Beard’s Creek, historic stone walls, 60 acres of conservation land and lovely walking trails! Enjoy manicured grounds and gardens, a skating pond, creek-side firepit, and even an outdoor shower! It also features one of the most iconic barns in the Seacoast – a 3-story, 96×45 structure that was painstakingly restored to include a large workshop, garage, recreation, horse stall and nearly unlimited options for storage/expansion!


Size: 3,925 sf


Price: $2,100,000


Listing details: The home offers 3,925SF with 5Beds/3.5Baths (which includes a 1 bed apartment/in-law suite), original wide pine floors, 6 working fireplaces, period-correct/ custom-made cabinets from “Kennebec Company”, slate counters, the original slate sink, and built-in Indian shutters. The kitchen, dining room, and three season porch overlook the private backyard, pond and creek! The master is ensuite and features a double vanity, walk-in shower, jacuzzi tub, and a private dressing room! Radiant heat, central AC, new windows, new state of the art gas furnace, first floor office, home gym and more! Located in a quiet country setting, yet an ideal commuting location tucked just off Rte 4. Approx. 2 minutes to downtown Durham/UNH, Moharimet elementary, Oyster River middle and high schools, and approx. 10 minutes to Portsmouth!


Contact: Jamieson Duston, Duston Leddy Real Estate, +1 603.365.5848

WELCOME HOME - (53 NEW BOSTON RD) | $465,000

53 New Boston Rd, Bedford, NH
Listing agent: Gina Rowe

Don’t miss this opportunity to own this beautiful designer curated 3 bedroom/two bath home that has everything you’ve been looking for! This single family in quaint Bedford with garage is just minutes to all routes and shopping… all for under 500k, with a 1.5 acres of land! Nothing left to do besides move in.


Size: 1,260 sf


Price: $465,000


Listing details: Brand new roof with limited lifetime warranty, new windows, and updated electrical panel. Designer curated features such as lighting fixtures, granite composite sink in the kitchen, modern quartz countertops throughout, and so much more! Come visit us at the Open House or schedule your showing today!


Contact: Gina Rowe, Realty One Group Next Level , +1 603-995-0099

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