Explore a collection of historic estates that seamlessly blend classic architecture with modern amenities. From the 1660 estate in Guilford, CT, one of the oldest homes with contemporary upgrades, to the renovated 1900 estate in Old Greenwich with a pool and over 3 acres, each property offers unique character and luxury. The 1815 estate features a barn, pool, and pond, while the 1740 colonial provides residential and commercial potential with a barn and cottage on 2.23 acres. For those seeking privacy, the 1910 Dutch Colonial estate sits on 51.2 acres and includes a carriage house, barn, and scenic trails. Each of these homes offers a rare opportunity to own a piece of history in some of Connecticut’s most desirable locations.
1. Relocated 1660 Pitkin Mansion
Priced at $2,295,000, the Pitkin Mansion is a 5,414 sq. ft. historic estate originally built in 1660 and relocated to Guilford in 1955. Set on nearly 4 acres, the property includes 5 bedrooms, 9 baths, and architectural details such as a broad gambrel roof and handmade English brick chimneys. Modern upgrades feature a geothermal system, central A/C, a pool with a pool house, a tennis court, a detached garage with a bonus room, and a barn with a full apartment.
Where is Guilford?
Guilford, Connecticut, is a coastal town in New Haven County, located on Long Island Sound, about 15 miles east of New Haven and 90 miles northeast of New York City. Known for its historic town green, colonial-era homes, and scenic waterfront, Guilford offers a mix of small-town charm and modern amenities. With beaches, marinas, hiking trails, and easy access to Interstate 95, it is a desirable location for both year-round residents and seasonal visitors.
Sunroom
Green textured walls and brick flooring is decorated with white wicker furniture and floral-patterned cushions. Large arched windows and French doors allow natural light to enter, while a skylight provides an additional view of the sky. Indoor plants and decorative elements add to the garden-like atmosphere of the space.
Dining Room
Red ceiling and floral-patterned blue wallpaper is furnished with a polished wooden table and upholstered chairs. A gold chandelier with red candles hangs above the table, complementing the room’s vibrant tones. A lit fireplace, built-in shelves, and antique-style furniture add to the room’s classic ambiance.
Kitchen
Floral wallpaper extends from the ceiling to the walls, complemented by a skylight allowing natural light. White cabinetry and a long island with a granite countertop provide ample storage and workspace. Large windows with decorative valances overlook a garden, creating a bright and inviting atmosphere.
Bedroom
Four-poster canopy bed covered in floral-patterned bedding and matching pillows. Blue-painted trim, wainscoting, and doors contrast with the wallpapered walls. A patterned area rug, antique wooden furniture, and a brick floor section add texture to the space.
Pool
A well-maintained swimming pool surrounded by dense greenery and mature trees. Large windows and a unique octagonal section with a cupola allow natural light into the interior. Stone patio area provides seating and shade with umbrellas near the pool.
Source: Coldwell Banker
2. Renovated 1900 Estate
Priced at $4,295,000, this 9,312 sq. ft. home in the Hillcrest Park Association sits on 3.23 acres and offers 5 bedrooms, 6 baths, and multiple living and entertainment spaces. Originally built in 1900 and newly renovated, the home features hardwood floors, exposed beamed ceilings, an open-plan porcelain-clad kitchen, a billiard room, an office, a gym, a theater/playroom, and a large recreation room. Outdoor amenities include a pool, screened-in porch, and fire pit, providing space for relaxation and entertainment. Conveniently located near schools, parks, train stations, and town, this property offers luxury and privacy in one of Old Greenwich’s most desirable neighborhoods.
Where is Greenwich?
Greenwich, Connecticut, is a coastal town in Fairfield County, located about 35 miles northeast of New York City along Long Island Sound. Known for its historic estates, waterfront properties, and strong financial sector ties, Greenwich offers a mix of suburban living with easy access to Interstate 95 and the Metro-North Railroad, making it a prime location for commuters. The town features top-rated schools, high-end shopping, golf courses, marinas, and cultural institutions, making it one of the most desirable places to live in the New York metropolitan area.
Living Room
Spacious living room with hardwood floors, neutral gray walls, and exposed ceiling beams. Large sectional sofa provides seating around a modern fireplace with a mounted television. Open-concept design connects to a staircase, hallway, and additional living areas.
Kitchen
White cabinetry, stainless steel appliances, and a large navy blue island with seating for four. Marble countertops and contemporary lighting fixtures add a sleek and clean aesthetic. Open layout connects to adjacent living spaces with hardwood flooring throughout.
Bathroom
Neutral-toned bathroom with a sleek vanity, modern fixtures, and a frameless glass shower enclosure. White tiled flooring and soft beige walls create a clean and simple aesthetic. Exterior door with a pet door provides access to an outdoor area.
Pool
Large backyard with a rectangular in-ground swimming pool surrounded by a well-manicured lawn. Dark blue house with white trim features multiple windows, dormers, and a covered patio area. Mature trees and landscaping provide privacy and a natural setting.
Source: Coldwell Banker
3. Renovated 1815 Estate
Priced at $2,245,000, this 2,640 sq. ft. home, built in 1815, sits on flat, usable land featuring a bank barn, gunite pool, mature trees, and a pond. The 4-bedroom, 3-bathroom home retains its historic charm with antique floors, hand-hewn beams, and multiple fireplaces, including a revived cooking fireplace and propane inserts in two smaller fireplaces. The primary suite with a walk-in closet is on the main level, while the upstairs is designed as two bedroom suites with walk-in closets or offices, offering flexible living space. Recent upgrades include a generator, new heating system, new interior and exterior paint, wood shingle roof, and built-in features, with the option to restore or repurpose the remains of a former tennis court.
Where is Roxbury?
Roxbury, Connecticut, is a small, historic town in Litchfield County, located about 85 miles northeast of New York City and 30 miles west of Hartford. Known for its rolling hills, preserved farmland, and colonial-era homes, Roxbury offers a quiet, rural lifestyle with easy access to nature trails, historic sites, and cultural attractions. The town is a sought-after retreat for those looking for privacy and scenic beauty while remaining close to larger towns like Washington and Southbury.
Library
Room with floor-to-ceiling green built-in bookshelves filled with books, decorative items, and a television. Large window provides natural light, complementing the warm wood flooring and colorful furnishings. Mid-century modern seating, an orange sectional sofa, and a statement glass chandelier create a vibrant yet inviting space.
Dining Room
Dining room with wooden furniture, woven-seat chairs, and dark trim framing large windows. Striped area rug and antique-style chandelier add contrast to the space. Exposed wooden beams and a stone accent wall contribute to a warm and traditional atmosphere.
Kitchen
Kitchen with exposed wooden ceiling beams, light blue cabinetry, and butcher block countertops. Stainless steel appliances, a built-in gas cooktop, and a farmhouse-style sink blend modern convenience with traditional elements. Large windows and a glass-paneled door provide natural light and outdoor access.
Bedroom
Bedroom with vaulted ceilings, exposed wooden beams, and large windows providing natural light. Wooden furniture, colorful bedding, and red window treatments add warmth and character. A mix of modern and vintage elements creates a comfortable and inviting space.
Source: Coldwell Banker
4. 1740 Colonial Gem on 2+ Acres
Priced at $1,000,000, this 3,418 sq. ft. antique colonial, built in 1740, sits on 2.23 acres and offers both residential and commercial zoning, making it ideal for a bed & breakfast, restaurant, bakery, or other business opportunities. The home features 4 bedrooms, 2 baths, original exposed beams, 5 fireplaces, wide walnut floorboards, and a custom-designed bee hive oven, preserving its period charm. Additional space includes a 1,500 sq. ft. walk-up attic with original heavy timbers, a full-length basement with a 9-foot ceiling, and a massive stone foundation with new cement flooring and supports. The property also includes a modernized post-and-beam barn, a cottage, and a scenic pond, offering a rare blend of historic character and versatile potential.
Where is Bethlehem?
Bethlehem, Connecticut, is a small, rural town in Litchfield County, located about 30 miles west of Hartford and 90 miles northeast of New York City. Known for its historic charm, scenic farmland, and peaceful atmosphere, Bethlehem offers a mix of countryside living with easy access to nearby towns like Woodbury and Litchfield. The town is also famous for its annual Christmas Festival, reflecting its festive name, and provides a quiet retreat with outdoor recreation, local farms, and historic sites.
Living Room
Living room with patterned wallpaper, burgundy window valances, and a white mantel fireplace. Plush sofas with classic upholstery, a wooden coffee table, and a chandelier create a warm and inviting space. Hardwood floors and multiple windows provide a balance of historic charm and natural light.
Dining Room
Dining room with wooden floors, a simple farmhouse table, and ladder-back chairs with woven seats. Blue and white checkered wallpaper, a wooden hutch displaying dishware, and a wrought-iron chandelier add a rustic charm. Large windows with sheer curtains provide natural light and a view of the outdoors.
Kitchen
Exposed wooden beams, painted cabinetry, and a large open hearth. A mix of vintage and modern elements includes a black countertop island, a farmhouse sink, and built-in storage. A walk-in pantry with open shelving provides additional storage space.
Bedroom
Floral wallpaper, wide plank wood flooring, and a dark wood four-poster bed. Large dresser with a mid-century design sits against one wall with a mirror above it. Two doors lead to other areas of the home, and a small bedside table provides additional storage.
Source: Coldwell Banker
5. 1910 Dutch Colonial Estate on 51 Acres
Priced at $1,200,000, this 3,307 sq. ft. Dutch Colonial estate, built in 1910, sits on 51.2 private acres with a carriage house, barn, gardens, and stone outbuilding. The 5-bedroom, 3-bathroom home features hardwood floors, two fireplaces, French doors, and intricate woodwork, preserving its historic charm while incorporating modern updates. The kitchen includes a Wolf gas stove and butler’s pantry, while the living room, formal dining room, and library enjoy abundant natural light. Located in Litchfield County, the estate offers walking and riding trails and is close to skiing, hiking, restaurants, and parks in Norfolk and Barkhamsted, as well as the Farmington River.
Where is Colebrook?
Colebrook, Connecticut, is a small, rural town in Litchfield County, located about 30 miles northwest of Hartford and 120 miles northeast of New York City. Known for its scenic landscapes, forests, and outdoor recreation, Colebrook is home to parts of Peoples State Forest and Algonquin State Forest, offering hiking, fishing, and wildlife viewing. With a quiet, country atmosphere and proximity to Norfolk, Barkhamsted, and the Farmington River, Colebrook is a peaceful retreat for nature lovers and those seeking a slower pace of life.
Porch
Spacious porch with a wood floor, exposed ceiling beams, and white round columns. Dark wood shingle siding and a white-framed door with glass panels create a traditional exterior. Outdoor seating, decorative urns, and warm wall lanterns add to the inviting atmosphere.
Dining Room
Dining room with a long wooden table, metal chairs, and a classic chandelier. A built-in bench seat, wooden door, and dark trim add warmth and character. French doors open to an adjacent space, creating a connected layout.
Kitchen
Large windows, wood-paneled walls, and natural-finish cabinetry. A stainless steel gas stove, farmhouse-style sink, and simple countertops provide functionality. A small dining table and rustic flooring contribute to a cozy, traditional atmosphere.
Bedroom
A brick fireplace, neutral walls, and a dark wooden four-poster bed. Large windows with sheer curtains provide natural light and views of the outdoors. A full-length mirror, antique chairs, and a patterned area rug add traditional charm.
Source: Coldwell Banker
