Greenwich CT Homes with Guest Houses

Scroll to view current single family homes with a gues house on the market in Greenwich Connecticut. Love what you see? Register with us to save your favorites and to get daily updates when similar properties are posted. Already have an account? Log in here! For more information about Greenwich, its available properties or insights into other residential properties that might be coming to market contact Edward Mortimer today
30 Field Point Drive Greenwich CT 06830

Greenwich, CT30 Field Point Drive

Price$30,000,000

Est. Mortgage: $/month

MLS Number 111224

  • Residential
  • Bedrooms 11
  • Full Bath 9
  • Square Feet 18068
  • Acreage 6.38

Remarkable Belle Haven Classic Georgian Colonial with only 2 previous owners. The estate sits on almost 6.4 acres. 2, 1 acre lots have been subdivided thus able to create a compound in addition to the guest house and cottage flanking the driveway. A brick walled inner courtyard leads to the front door. Grand center hall with fireplace and wood paneling opens to a columned terrace overlooking the beautiful property. It was built in 1900 and enlarged over the years with the largest addition in 1991, nearly doubling the home. The magnificent library features a doorway from Grosvenor House, London. Formal dining room with marble fp. Living room has raised wainscoting, marble fp. 2nd fl has grand master suite as well as 6 bedrooms. A unique property with unparalleled privacy and beauty.

Listing Courtesy of Brown Harris Stevens CT,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

435 - 429 Round Hill Road Greenwich CT 06831

Greenwich, CT435 - 429 Round Hill Road

Price$25,500,000

Est. Mortgage: $/month

MLS Number 114067

  • Residential
  • Bedrooms 16
  • Full Bath 11
  • Square Feet 20639
  • Acreage 8

One of a kind offering on 8 acres presents this iconic STONEHILL compound in the coveted Greenwich countryside. Impressive Georgian scale is woven throughout this unique and exquisite offering. The 14,000+ SF, 3-story, main estate, formerly owned by Tommy Hilfiger, is outfitted with luxurious features of architectural note. Resort-like amenities throughout the lower level include a gym, sport court and home theater. This private estate combines into a sophisticated living experience with pool, pool house, synthetic turf tennis court and mature gardens. Plenty of room for guests or extended family in the additional three homes which include an updated 4 BR guest house, a 3 BR cottage and a 2 BR cottage. 3 gated entries access the property. Main house offered for sale separately.

Listing Courtesy of Compass Connecticut,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

435 Round Hill Road Greenwich CT 06831

Greenwich, CT435 Round Hill Road

Price$19,995,000

Est. Mortgage: $/month

MLS Number 114065

  • Residential
  • Bedrooms 7
  • Full Bath 7
  • Square Feet 14798
  • Acreage 4

STONEHILL, an Iconic Greenwich compound offers an unparalleled sophisticated lifestyle. Impressive Georgian scale is woven throughout this exquisite manse, starting with the pleached linden tree-lined drive into the grand center hall, and within each of the 20 distinctly designed rooms. Every area of this 14,000+ SF home, formerly owned by Tommy Hilfiger, is endowed with unique and glamorous architectural notes. Standout features include a dining room which comfortably seats 40 guests, a signature two-story Great Room, and a luxurious master suite with fireplace, spa bath & dressing rooms. The lower level boasts a gym, massage room, sports court, wine cellar & world-class home theater. Immaculate exteriors incorporate a luxe pool, pool house, synthetic turf tennis court and mature gardens.

Listing Courtesy of Compass Connecticut,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

22 Round Hill Club Road Greenwich CT 06831

Greenwich, CT22 Round Hill Club Road

Price$19,000,000

Est. Mortgage: $/month

MLS Number 114549

  • Residential
  • Bedrooms 6
  • Full Bath 5
  • Square Feet 9552
  • Acreage 4.75

Unparalleled six-bedroom stone and shingle style home, part of a magnificent mid country compound, sits on 4.75 gated acres with pool, pool house, tennis court, two-bedroom guest house with gym, fabulous party barn and lush gardens off Round Hill Road. Completely rebuilt and expanded to perfection, the stylish interior combines original 1920's details with modern updates. Boasts double height skylit entry; vintage floors in dining room; chef's kitchen open to sitting room with fireplace; stone patios off living, dining, family and play rooms; billiards room, two main level guest suites and second floor primary suite with fireplace, dressing room and spa bath. Entertaining barn, designed by Geoffrey Hall, offers catering kitchen, great room with stone fireplace, bar and multiple game rooms.

Listing Courtesy of Houlihan Lawrence

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

32 Grahampton Lane Greenwich CT 06830

Greenwich, CT32 Grahampton Lane

Price$14,400,000

Est. Mortgage: $/month

MLS Number 112740

  • Residential
  • Bedrooms 7
  • Full Bath 8
  • Square Feet 10534
  • Acreage 2.53

This Greenwich house is under construction and will be ready for you to make it your home in late 2021. Complete with architectural innovation and stylish refinements, this 7 bedroom brick classic home will feature modernity throughout 4 floors. The estate, positioned grandly on 2.5 verdant acres in a Greenwich estate area, is surrounded by a historic stone walls, mature trees, lush lawns with a 2 bedroom guest/pool house of 1,200 SF and pool with a spa. It is approached down a gated drive to a welcoming entrance and parking court. This impeccably designed home presents a sublime aesthetic with chic and sophisticated interiors by Mari Battone of Mar.b Interiors. Socialization and ease of entertaining were top of the architect's mind in the layout of this home.

Listing Courtesy of Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

205 Round Hill Road Greenwich CT 06831

Greenwich, CT205 Round Hill Road

Price$12,995,000

Est. Mortgage: $/month

Contingent

MLS Number 108854

  • Residential
  • Bedrooms 7
  • Full Bath 7
  • Square Feet 9500
  • Acreage 5.12

Come see this 1820 architectural masterpiece on Round Hill Road! The iconic ''Israel Peck Estate'' has space for everyone...9,500 SF of beautifully appointed rooms including, 7 bedrooms, 7.5 baths, a gourmet chef's kitchen, butler's pantry, spacious breakfast room and family room with fireplace. This home has been painstakingly restored, adding every modern amenity one could imagine, while maintaining and preserving every original detail. The property sits on 5.12 acres and features a pool, pool house, tennis court, and beautiful English gardens. A guest cottage and a six car garage complete this estate. This centrally located estate is just moments from town, shops, train, and less than one hour to Manhattan. A beautiful gem waiting to be discovered!

Listing Courtesy of Douglas Elliman of Connecticut LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

21 Clapboard Ridge Road Greenwich CT 06830

Greenwich, CT21 Clapboard Ridge Road

Price$11,900,000

Est. Mortgage: $/month

MLS Number 112596

  • Residential
  • Bedrooms 6
  • Full Bath 6
  • Square Feet 8537
  • Acreage 6.13

Enjoy 6.13 parklike, private acres on Clapboard Ridge Road in the heart of Mid-Country Greenwich and the RA-2 zone. Elegant main residence, barn with REGULATION SQUASH court, lounge area and gym, one bedroom guest cottage with kitchen, pool, pool pavilion, tennis court, golf hole with sand traps, plus a detached garage/studio. Six-bedroom Main House showcases Diamond Baratta design throughout spacious living space ideal for both casual and formal entertaining. Notable features include a dramatic staircase, vaulted ceilings, oversized rooms, custom millwork, six fireplaces, expansive terraces and garaging for five cars. Incredible all-in-one turn-key estate with every sporting amenity located in a prime location minutes to town.

Listing Courtesy of Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

11 Sherwood Avenue Greenwich CT 06831

Greenwich, CT11 Sherwood Avenue

Price$9,800,000

Est. Mortgage: $/month

MLS Number 112301

  • Residential
  • Bedrooms 5
  • Full Bath 5
  • Acreage 28.44
  • Village North Parkway

Applecrest is one of Greenwich's greatest hidden treasures. Its 28 acres provide a tranquil escape for family, friends & guests who will enjoy the breathtaking scenery including acres of lush lawn along the Byram River with a magnificent waterfall and private lake. Regardless of the season, Applecrest offers countless activities and adventures for all ages. The heart of the private compound is the stylish Nantucket pool house replete with a full kitchen, 2 changing rooms, a gathering room and a covered terrace for complete relaxation poolside. Alternatively, enjoy fishing on the pristine lake, or find yourself relaxing on a hike through the protected on-site trails. There are three five-bedroom residences, plus a 2 bedroom cottage.

Listing Courtesy of Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

21 Grove Lane Greenwich CT 06831

Greenwich, CT21 Grove Lane

Price$9,800,000

Est. Mortgage: $/month

MLS Number 114490

  • Residential
  • Bedrooms 7
  • Full Bath 7
  • Square Feet 10393
  • Acreage 3.12

Stroll to town from this fully renovated Greenwich estate, majestically sited on 3.12 beautifully landscaped acres. Living and dining rooms flank grand entry hall; butler's pantry leads to enormous eat-in kitchen and family room; adjoining terrace with outside fireplace overlooks the pool, providing many months of dining al fresco. Primary suite with balcony has luxurious bath, two walk-in closets and dressing area. Gracious guest suite and three additional bedrooms, a huge sun-filled playroom/upstairs family room complete the second floor. Spacious office, massage room, bath and two bedrooms complete the third floor. Lower level has gym, movie room, wine and tasting rooms. Elevator, three-bedroom 2883 sq ft guest house, three-car garage. Rare opportunity to own a Greenwich classic

Listing Courtesy of Houlihan Lawrence

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

8 Dewart Road Greenwich CT 06830

Greenwich, CT8 Dewart Road

Price$8,495,000

Est. Mortgage: $/month

MLS Number 113970

  • Residential
  • Bedrooms 7
  • Full Bath 7
  • Square Feet 8315
  • Acreage 2.71

Exquisite gated estate sited down a long driveway on private mid-country lane with impeccably renovated 5-bedroom main house, guest house, pool pavilion and exceptional grounds. This secluded oasis is surrounded by green and highlighted by botanical gardens with staged blooms, an expansive lawn area, a stone grilling station covered by wisteria filled trellis, outdoor fireplace, play-set area and beautiful pool with pool house. Since the complete renovation work in 2016, the house and grounds have been meticulously maintained. The pristine interior of this stone and shingle-style home is flooded with natural light and the living space extends to 8,315 sq. ft. on three levels. Separate guest quarters above the detached garage structure. A truly unique home new to the market - move in ready

Listing Courtesy of Brown Harris Stevens CT,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

 

Listing data provided by Greenwich MLS

15.4.6 Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect participants and/or the MLS from liability. Displays of minimal information (e.g. “thumbnails”, text messages, “tweets”, etc., of two hundred (200) characters of less are exempt from this requirement but only when linked directly to a display that includes all required disclosures. (Amended 5/12)